Chapters

1. 00:00 - Headlines: 80 cents of your dollar

2. 00:42 - Why this show exists, and what this episode covers

3. 01:44 - Ogilvy on writing well, and why boring is a sin

4. 03:40 - His last will and testament: study the product, promise a benefit

5. 04:22 - Do the homework: become the best-informed person on the account

6. 06:38 - Give the facts

7. 08:31 - Details matter, and the 35-pound figure

8. 09:55 - How to write potent copy

9. 10:15 - The ten headline guides

10. 14:04 - Clear versus clever

11. 15:11 - Body copy: write to one person, be specific

12. 15:55 - Long copy: Schlitz and the Rolls-Royce ads

13. 16:45 - Every ad is a complete sales pitch

14. 17:03 - Testimonials

15. 17:54 - Helpful advice

16. 18:23 - Why the multi-step ad funnel falls short

17. 19:34 - Good content, and why giving value builds reciprocity

18. 20:43 - Captions

19. 21:38 - Formatting long copy

20. 22:57 - "Broetry" and timeless principles

21. 23:44 - Plain writing: jargon and acronyms

22. 24:44 - Presentations, rehearsal and AI slides

23. 26:15 - Be brief, be brilliant, be gone

24. 28:00 - The unconscious, and a closing example of clear writing

25. 29:41 - Close, guide and book

What's inside the playbook

• A ten-check headline scorecard, with space to write sixteen headlines

• A copy and clarity checklist for body copy, long copy and everyday communication

Get the free playbook:
https://www.derevaco.com/marketing-meditations/how-to-write-headlines-and-copy-playbook/

Read along:
Confessions of an Advertising Man by David Ogilvy: https://link.amazon/B00Gp1lUC

Link to podcast episode page:
https://www.derevaco.com/marketing-meditations/how-to-write-headlines-and-copy/

Episodes you might like:
001: Why Marketers Ignore What Works and Repeat What Doesn't

Chapters

1. 00:00 - The pig and the truffles: knowledge over ignorance

2. 00:27 - Why this show exists, and why Ogilvy is the hub

3. 02:19 - "Allergic to rules": rules, frameworks, playbooks and skills

4. 03:41 - 49 ads in reverse type, years after the research

5. 05:23 - Why marketing teaches no underlying principles

6. 05:46 - Ogilvy's lessons: the 19-to-1 gap and promising a benefit

7. 07:11 - The Magic Lantern: do rules make work dull?

8. 09:09 - Price-off deals and the short-term trap

9. 11:06 - The 15% and the 85%

10. 12:47 - The trap of more

11. 15:10 - Approval layers, flat fees and incentives

12. 18:09 - A moving parade, not a standing army

13. 19:47 - Test everything

14. 21:17 - Sell the outcome, then choose the promise

15. 24:06 - Give the facts

16. 26:56 - Brand image, and research as a lamppost

17. 28:43 - The brand as a coefficient

18. 29:45 - The ice-box policy

19. 31:27 - Testimonials and the question "Are you for me?"

20. 33:02 - Why award-winning ads prove little

21. 34:32 - Curiosity, photographs and faces

22. 39:08 - Match the medium

23. 41:35 - Problem, remedy, proof

24. 42:46 - Why specialists win

25. 44:58 - Close, playbook and book

What's inside the playbook

• Nine principles from the episode, each with Ogilvy's evidence and a question to ask of your own work

• The Audit: a worksheet for grading your last five assets

• A decision rule for what to treat as settled and what to test

Get the playbook:
https://www.derevaco.com/marketing-meditations/ignore-what-works-playbook/

Read along:
Confessions of an Advertising Man by David Ogilvy: https://link.amazon/B00Gp1lUC

Link to podcast episode page:
https://www.derevaco.com/marketing-meditations/ignore-what-works/

CEO: “When is the new campaign launching? It’s been a month since the last one went live.”

CMO: “We’ve been running that case study ad for a couple months now, can we refresh it?”

VP of Demand: “Remember that ad set we ran back in Q1 with the before/after visuals? Looking back on demo request volume from the past year, it seems like they peaked around the same time + started to dip after we replaced them with the next ad set.”

Or even more pointed at myself, I know there have been times this past year where I’ve been thinking we were overdue for an ad refresh + started the process to kick off the next round.

Butttt have we ever stopped to wonder what logic was driving the need to launch the new ones? Most of the time, it seems like it’s just a function of time.

Campaigns are given an arbitrary set of days to run
A content calendar has pre-determined dates for ads to be running
Or, as David Ogilvy put it in Confessions of an Advertising Man (and what really made me stop + think about this):

Scores of good advertisements have been discarded before they lost their potency, largely because their sponsors got sick of seeing them.

You aren't advertising to a standing army; you are advertising to a moving parade. Three million consumers get married every year. The advertisement which sold a refrigerator to those who got married last year will probably be just as successful with those who get married next year.

Subscribe now

Sponsor: Primer

Outbound is broken + LinkedIn somehow keeps getting more expensive. Now what?

Every B2B marketer is paying premium prices for the same shrinking pool of attention on the same two channels (LinkedIn + Google).

Meanwhile, channels like Meta, YouTube, + display cost a fraction of LinkedIn…but most B2B teams can’t use them. Standard account lists match at 15%, AKA audiences are too small to learn + too noisy to convert.

Primer fixes the match rate problem. They turn your ICP, target accounts, and net-new prospects into 45-85% matched audiences across every major ad platform. Now the efficient channels we couldn’t use before due to low match rates are suddenly usable.

Get started with a free account + 30-day trial of paid plans today!

Fun fact: Rippling credits them for their $145M Series B success.

Try Primer today

And the timeline is only speeding up

With all of the recent AI mandates or AI shaming (“What do you mean you aren’t using AI as part of your demand gen workflow?"), the overarching message is that the solution lies inside of the “magic” formula: volume x speed.

We used to be limited by creative production, but AI can create more for us now, so why ship 10 ads when we can ship 100?

We used to run 1 campaign every quarter, but AI can move faster for us now, so why not run 1 campaign every month?

Do more. Go faster. Get more at bats. Hit more audiences.

But there are three things that have me going hmm when I see/hear this advice:

1. Where’s the feedback loop? Except for a handful of people I see using AI from a systems perspective vs solely as execution, for the one thing that all of those additional at bats are giving you (data), almost no one is taking those insights out + incorporating that feedback loop back into what’s created next.

2. Our attention spans are shorter than ever + we’re taking that out on our audience. Just because we see the ads daily when we’re inside the ad platforms doesn’t mean our audience has. We’ll have seen the ads hundreds of times from brainstorm to edits to campaign build in the platform before our audience even sees it once. Then compound the fact that our now 100+ ads in rotation means budget is spread really thin (because let’s be real, few are being given more budget right now), so we’d be lucky if the ad frequency for our market is ≥ 1 for most of those ads.

3. We’re iterating on the winner(s) at best, not continuing them. This was a big one for me this year. We’d have a handful of ads that just crushedddd it. Then the next campaign came around, we’d turn off all the ads in the old campaign, take the learnings from what did/didn’t work, and apply that to future ads. But after that Ogilvy quote had me facepalming myself, I thought to myself “why am I pulling something that’s still working and hoping that maybe a few ads in the next campaign can match this?”

What I’m doing about it

Shrugging it off + hoping for the best.

Kidding.

The data side of me is checking the numbers inside platforms for datapoints other than how many days it’s been since launch:

• Frequency at the ad level

• CTR/view rates within the same audience

• Performance decay rate relative to other ads launched at the same time

But then since we do have to keep up with leadership’s expectations of shipping more/faster, I changed the account structure we used for which ads were running at any point in time + how much budget to give them.

Old way we ran:

• New campaign gets the heavy majority of the budget (would often be a mish-mash of product/feature ads, case study ads, etc.)

• Old campaign is retired

Rinse + repeat the above until exhaustion or mental breakdown occurs first.

New way I recommend:

• New campaign (20% of budget)

  • This is usually oriented around time-based relevance: a new product/feature release, a seasonal offer, what’s popular with the market right now (aka our adaptive POV), etc.

• Case studies/customer proof (20% of budget)

• Thought leader ads (20% of budget)

• Use case content (20% of budget)

• Then last + most importantly - top performers (20% of budget)

  • Instead of ending all the ads in the “old” campaign cold turkey, I’d take the handful that I deemed as top performing and/or still performing, and roll them into an evergreen “Top Performers” campaign. This extends the life span of them for as long as I want, I can toggle various ones on/off if I know some are more seasonal in nature, and/or when a proper system is in place to iterate off what’s worked, we have a beautiful library ready to be used as inputs.

I really like this new setup for two main reasons.

First is the balance it brings. No more big swings in top of funnel performance if a campaign hits (or flops).

Instead of taking 80%+ of the budget and hoping for the best, it’s now roughly a fifth of the budget. If it takes off, great, push more budget to it. If it flops, great, pull back some budget from it. There’s built in containment here.

Second is the compounding performance it brings. We’re stashing top performers as time goes on, so our library of “what works” keeps growing and we can push harder on that campaign budget at any time if needed.

We also get to learn from that pool + can either manually or via AI systems build a feedback loop from that campaign so that everything new we creates has more data available to inform what’ll increase the likelihood that those ads are also successes.

Charlie Munger may not have been a marketer, but I’m pretty sure he’d agree with this principle.

See you next week,
Sam

When letting me know about this Q4 goal, the first thing they asked me was, “please come up with a media plan to help us achieve this. We need to present it to leadership later this week.”

Scaling paid media is my specialty, so this type of request isn’t an uncommon one (I strangely love this kind of stuff - it’s a puzzle to solve for how to hit new growth targets efficiently 🤓).

But here’s the curveball you probably weren’t expecting: the plan I presented to them 2 days later had ZERO increase in paid media spend AND was set to not only help them drive 3x more meetings booked, but actually 4-5x it.

Crazy talk, right???? I would’ve thought so as well had I not been stopped in my tracks after doing a quick audit of their funnel before telling them how much to spend.

Subscribe now

Sponsor: Primer

Outbound is broken + LinkedIn somehow keeps getting more expensive. Now what?

Every B2B marketer is paying premium prices for the same shrinking pool of attention on the same two channels (LinkedIn + Google).

Meanwhile, channels like Meta, YouTube, + display cost a fraction of LinkedIn…but most B2B teams can’t use them. Standard account lists match at 15%, AKA audiences are too small to learn + too noisy to convert.

Primer fixes the match rate problem. They turn your ICP, target accounts, and net-new prospects into 45-85% matched audiences across every major ad platform. Now the efficient channels we couldn’t use before due to low match rates are suddenly usable.

Get started with a free account + 30-day trial of paid plans today!

Fun fact: Rippling credits them for their $145M Series B success.

Try Primer today

First things first

Before jumping into making any blanket recommendations, I dig into the data to see what’s going on. Every company is a unique snowflake after all…

So with this client (series B, ~$50-100M tech company), I assumed there were certain systems, processes, + best practices in place, but because we all know what they say about assuming (and how often this has come back to bite me in the butt), I first principled the top of their funnel.

• GA4 to get data on their web traffic

• Reviewed the ad platforms they were already spending in + the results

• Mapped out the various funnel entrance points

• And filled out the demo request form

Things were pretty standard when looking at all the above. A few notes here + there on some optimizations that would help, but one thing that surprised me was that after filling out the demo request form, the confirmation page was a simple “Thanks. A member of our team will be in touch within 24-48 hours.” Huh, haven’t seen a company still doing this manually in a while, that’s surprising.

I took all of the above top of funnel data + then moved on to their CRM to get the middle + bottom of funnel data to get a view of the full funnel. Meetings booked + attended, SQOs, late stage opps, closed won, etc.

Then I plugged it all into the tool I built to gauge funnel health (www.affect.so) + my eyes about jumped out of my head when I saw this:

Demo > meeting booked was 4x LOWER than benchmark

This one boggles my mind that some companies still don’t leverage calendar scheduling tools as part of the demo request submission process. They’re inexpensive + pretty much guarantee instant results.

There’s also an insane amount of leverage here:

• If you sell multiple products, serve multiple verticals, etc., this can be applied universally + benefit every one of these funnels

• With it being near the top of the sales funnel, that means it impacts every stage of the funnel that follows. e.g. if 2x more people book a meeting from demo request, assuming conversion rates downfunnel remain the same, that’s 2x more closed won deals without changing anything else.

So when I came back to them with my recommendation, this was the first slide I presented:

As I said earlier - wild, right???

So aside from telling them I don’t recommend spending more in order to hit this goal, that we needed to solve the submission > meeting booked problem first, I then hit them with a second counter-intuitive recommendation.

I initially thought it’s probably going to take a month or so to get this purchased + implemented, so let’s increase paid media spend during that time to keep the funnel filled. Then I ran the numbers and I realized we needed to do the opposite.

At their current rate, they were paying ~$3,300 per meeting booked. Once the scheduler was live, that same spend would buy a meeting for ~$775. AKA, spending during the month it took to implement meant paying 4x more for the exact same outcome.

So I recommended we don’t push media dollars until the scheduler was live so we could pool every media dollar to go 4x further the last 2 months of the quarter. We’d deploy the same total budget, just holding it until the scheduler was live vs. spending it evenly across the quarter.

Yes, this type of recommendation to wait to spend always gives me anxiety since it’s compressing the time window to drive results, but I’ve seen the impact this singular lever has enough times to have confidence that they’d easily get to the industry benchmark conversion rate of 65%.

TBH, with every company I’ve worked at or had as a client that implemented this, 65% was lower than what we saw as we were usually in the 75-90% range, so if anything the projected meetings scheduled I forecasted was conservative.

Now it simply became a matter of committing to the plan + treating this as the priority it was.

The takeaway

When we’re given bigger growth goals, most of us almost always default to something like “ok, how much more do we need to spend to achieve that?”. It’s the easiest + quickest lever to pull, and leadership/finance usually understand that an investment needs to be made to drive more demand.

BUT, unless we’re aware of the bigger picture + funnel health, doing “more” or spending “more” is only going to give us “more” of whatever problems we have, like more leads slipping through the cracks.

With this client, we could have spent more to hit the goal, but knowing goals would only be increasing come 2027 + across their other markets, fixing this now was a no brainer to me. Getting a scheduler in place would set us up for future success, help us hit the Q4 goal, and hopefully gain a few brownie points with their finance team as being (what I assumed) the only demand gen partner who recommended not spending more on paid media to achieve their goal.

Before the next “we need more” conversation, pull your conversion rates at each stage + compare it to benchmarks for your industry. The best place to put the next dollar of investment just might not be into paid media, but somewhere else.

See you next week,
Sam

What I’m about to share has made me 10x more productive, but is FAR from anything new or something I came up with. It was mostly one of those “no duh/facepalm” moments after struggling for months with the ability to focus.

So what’s the big secret that I’m now swearing by?

Subscribe now

Sponsor: Primer

Outbound is broken + LinkedIn somehow keeps getting more expensive. Now what?

Every B2B marketer is paying premium prices for the same shrinking pool of attention on the same two channels (LinkedIn + Google).

Meanwhile, channels like Meta, YouTube, + display cost a fraction of LinkedIn…but most B2B teams can’t use them. Standard account lists match at 15%, AKA audiences are too small to learn + too noisy to convert.

Primer fixes the match rate problem. They turn your ICP, target accounts, and net-new prospects into 45-85% matched audiences across every major ad platform. Now the efficient channels we couldn’t use before due to low match rates are suddenly usable.

Get started with a free account + 30-day trial of paid plans today!

Fun fact: Rippling credits them for their $145M Series B success.

Try Primer today

When do I focus best?

That was the question I asked myself as I was struggling one afternoon to sit down + get into a task I knew I needed to get done.

I noticed it was starting to snowball on me as I kept deferring it for a few days + it mentally became a much bigger “thing” than it really was as a result. So like the overthinker + overanalyzer that I am, I worked backward from the outcome (me twiddling my thumbs because I couldn’t bring myself to focus) to the inputs that led to this not-ideal outcome.

My schedule at the time looked like this:

• 8:30-9a = map out plan for the day, catch up on slack/email

• 9a-noon = 1:1s, meetings, etc.

• noon-1p = lunch

• 1-2p = “catch up” slack/email time, work through my to-do list

• 2-3:30p = meetings, working sessions, etc.

• 3:30-5:30p = where my calendar was most often “open” + time I could actually do work

Lovely day, isn’t it?

Yeah definitely not. Everything I did was reactive from the time I started my day until 3:30p. Then being realistic, that 3:30-5:30p time often had what I planned to do replaced by something that was “super urgent” + needed to be done yesterday.

On top of that, I’m notorious for having the post-lunch food coma, so that 1-2p time often meant task-snacking on items from my to-do list that felt good to check off, but weren’t really impactful in the big picture.

Back to the question posed at the top of this section, “when do I focus best?” this was the one that had me 🤦‍♂️’ing myself the most. For years I’ve been most productive in the mornings. That’s when my focus is highest + the day’s decision fatigue hasn’t set in yet.

But the way I structured my calendar completely ignored that.

So as I’ve started on this next stage of my career working with clients again, I decided to make this a non-negotiable + built it into my calendar from day 1.

My days now

By seeing these blocks already on my calendar, I treat them as if they’re a meeting already booked that can’t be moved. It also prevents others from scheduling time during those hours via a calendar booking link since those hours won’t show as available.

Note: yes, I know there’s 1 meeting smack in the middle of my Monday deep work time that productivity experts would cringe at, but it’s our weekly DemandLoops team sync that was scheduled long before I became part of the crew. Sharing because you’ll probably have a few other similar scenarios to this + it’s ok. This isn’t a binary exercise where it’s all or nothing, sometimes we have to be a little flexible.

I still use my ~8-9a time to plan out the day ahead + catch up on pressing slack/emails, but as soon as I’m done with those, I jump right in.

On my to-do list each day, I have 1-2 “most important work” items that sit above everything else. These are the items that get worked on during the morning focus time. That way I know that should nothing else in the day go to plan after my focus time, I’ll still be able to consider the day a success knowing I made significant progress on the most important work at the time.

As of recent weeks, some days that’s looked like any of the following:

• Hubspot audit + analysis

• Custom project scoping for potential clients

• Google Ads review + scale plan

• Lead management/process audit

• Auditing 3 current markets a prospect was going after + running the numbers to make a recommendation for where to apply their focus vs. spreading thin trying to hit them all

• ABM readiness audit + the plan to be able to move to this

• Scale plan to 3x the number of meetings booked a client needs to hit their Q4 goal (without saying “just put it all into paid media!”)

Meaty projects + made harder when task-switching is involved, so I simply removed that variable.

Now I’m finding myself setting timelines for clients or myself that I’m delivering on multiple days in advance because I’m able to flow through the work so much faster than before by having clear focus on what I need to be doing AND only doing that during the time carved out for it.

That’s it - that’s the big secret

Figure out your most productive hours, block them off, + protect them as unmovable.

Definitely not sexy, and as I said, definitely not anything new or novel being shared here.

Just one of those things you hear people say enough times, finally decide to try for yourself, and then shake your head at yourself for not doing it sooner.

See you next week,
Sam

Now that I’m back from the in-house life to working with multiple clients, it’s been interesting to see what’s changed over the last 3.5 years.

TBH, a lot of things haven’t changed - the issues that have been issues for years are still running rampant inside most companies. The opportunities that have been opportunities for years are still there for the taking, just a matter of actually executing them.

When I was on my own in-house island, I was always wondering if what we were experiencing was unique to us or a larger trend occurring across the market.

So today’s newsletter is going to be a little bit different than normal. I’m going to share what I’ve been seeing + hearing over the past month as I’ve entered back into the fractional/client-facing world. Some of this will probably feel validating to you + give you that “I thought I was going crazy seeing this” feeling knowing you aren’t alone. Some might have you realizing you’re farther ahead than you thought you were. And some might have you thinking “uh oh, we’re a little behind.”

Subscribe now

Sponsor: Primer

Outbound is broken + LinkedIn somehow keeps getting more expensive. Now what?

Every B2B marketer is paying premium prices for the same shrinking pool of attention on the same two channels (LinkedIn + Google).

Meanwhile, channels like Meta, YouTube, + display cost a fraction of LinkedIn…but most B2B teams can’t use them. Standard account lists match at 15%, AKA audiences are too small to learn + too noisy to convert.

Primer fixes the match rate problem. They turn your ICP, target accounts, and net-new prospects into 45-85% matched audiences across every major ad platform. Now the efficient channels we couldn’t use before due to low match rates are suddenly usable.

Get started with a free account + 30-day trial of paid plans today!

Fun fact: Rippling credits them for their $145M Series B success.

Try Primer today

What hasn’t changed

This is the part that probably surprised me the most. Many of the things that we marketers have been struggling with for years, well, we’re still struggling with them 🤷‍♂️ Similarly, some of the things that have worked well for years are still going strong.

With that, here’s what I’m seeing hasn’t changed all that much:

(Lack of) data hygiene

Inside the first week of being fractional, I saw/spoke with multiple companies who had MAJOR duplicate issues inside their CRM. I’m not talking a couple accounts here + there that led to awkward conversations for BDRs/AEs when they realized they were calling a customer, I’m talking 25-50% of their CRM having duplicate accounts, leads, and/or contacts.

The part that had me lol was that these companies all knew they had a big issue because their duplicate rules were firing telling them “hey, this might be a duplicate” inside their CRM, but they didn’t have someone owning/executing the actual merging/deletion of any of these, so they just…sat there 🤦‍♂️

And the reason for this ultimately leads us to the next thing that hasn’t changed…

Execution

The strategies are there + the documentation for various processes, frameworks, etc. are all created, but when it comes to someone owning the execution and/or doing the execution at all…

Not sure if there’s a fear of being held to a specific outcome or responsible for the health of a system, but it’s like a paralysis has settled in. Ideas + plans are being shared galore, but then everything just kind of sits there when it comes time to do something.

• The person/team who’s allowed to hit the “merge records” button

• The demand gen marketer who takes the campaign brief + gets the campaign live

• The SEO/AEO marketer who takes the list of keyword opportunities + creates webpages that aren’t complete AI slopdust, but have a real POV + voice behind them

Fast ROI expectations

“Hey how’s that new campaign going that we launched Monday? Any new opps yet?”

Some things never seem to change + this is one of them.

A new AE is hired + finance builds in their “ramp” period until they know they’ll be producing pipeline and then closing deals.

Meanwhile, finance is like “yooo marketing, we just gave you a couple thousand dollars 2 days ago, where’s the return on it? BTW if we don’t have a report on what every single ad dollar did, we’re pulling the budget and putting it into BDRs.”

Managing internal stakeholders + setting appropriate expectations is something that I doubt will ever go away for us marketers. This is something I have to constantly remind myself of + why I wrote a 3-part series on how to get leadership buy-in.

After helping them understand how buyers buy in today’s world + shown them the data supporting the shift in strategy + execution you’re going to make, the next two questions they’re going to ask you are:

1. What will it look like to make this shift?

2. When should we expect to see these new + improved results?

And that’s when I usually pull out some flavor of this handy dandy visual:

What has changed

Cold outreach

Holyyyyy cow has this one gotten worse. Yes, people are answering cold calls/emails at lower rates than ever before, but the effort going into > 95% of those cold calls/emails is just about as minimal as it gets.

I see tons of super templated, generic emails going out OR super AI slop that reads as AI slop. Then there’s the higher volume of cold calls that technology has enabled, BUT those cold calls aren’t even being utilized in a way that’ll help them compound over time.

^^ that’s a section of my missed calls from a few weeks ago. Whenever a call comes through from a number I don’t recognize, I screen it to voicemail. Otherwise I’d never get anything done in my work day.

But here’s the thing - of the last thousand cold calls I’ve probably had come through this past year, I can count on ONE HAND the number of those who left a voicemail.

“But Sam, leaving a voicemail is sooooo much work”

Wahhh.

If someone doesn’t know who’s calling, they’re probably not going to answer. And if you don’t tell them who it is that’s calling, you know what’s probably going to happen the next time you call from that same number they don’t recognize (or heaven forbid it’s one of those fake “I’m calling from your area code!” numbers) - they probably won’t answer that time either!

I started my career as a BDR so I have full sympathy for those in that role - it’s one of the hardest I’ve ever had. But the “best practices” that have been used over the previous handful of years make me think the definition of “best practices” has shifted from “best” in driving results to “most convenient” for the person doing the cold calling.

SEO/AEO/GEO

I don’t think this one’s going to surprise many of you here, but SEO and general search/answer engine optimization has been shaken up with the rise of LLMs in recent years.

As much as I wish it still worked, the days of keyword-pumping articles + shipping hundreds of blog posts per month in order to rank on Google are long behind us.

Then add to that things like AI overviews being shown at the top of the search engine results page, answers being given directly in tools like ChatGPT + Claude, and all of a sudden we have fewer clicks + visitors by the hundreds or thousands.

So is SEO not working anymore? How do we know if what we’re creating is being picked up + showing us in a good light in LLMs?

Well, remember the whole “dark social” thing marketers recognized in the early 2020s + defined the shift from lead gen —> demand gen? SEO is going through that now with “dark SEO” as users are researching + gathering information much differently now than they were just a few years ago.

With this shift in behavior, it’s made me rethink the metrics, KPIs, and goals relative to SEO/AEO.

What I’m putting less weight behind:

• CTR as a primary success metric (or at least, unbranded CTR)

• Click traffic directly from SEO

• Click-to-conversion attribution models

What I’m putting more weight behind:

• AI visibility + citations

• Brand search volume trends

• Brand lift measurement over time

• Self-reported attribution citing things like “web research” or “ChatGPT”

I’ll be honest - putting less weight behind clicks feels weird/wrong. It goes against decades of SEO muscle memory. The new truth I’ve come to realize is that our VERY best SEO work might never generate a click. And that’s ok.

Just like on social, we’re optimizing for memorability - being the name people remember when they have a need. And when that need comes to a head, they come straight to us.

Webinars

Webinars work.

Webinars work really well.

I know. You probably expected me to say they aren’t working like they used to.

And that’s because they weren’t…for years. We had the COVID boom of webinars where everything was a webinar + since we were confined to our houses, it was our only way to interface with others. So after a few years of that we were burnedddd out on webinars.

But fast forward to this past year + I’ve been shocked by registration AND attendance rates of the webinars I’ve hosted or attended.

I’m not saying every webinar is a hit (plenty still flop, trust me), but the ones that have been driving a ton of registrations + having those people actually attend/watch the recording after have all been doing one similar thing:

Positioning the webinar around a very specific use case/JTBD and having the webinar go beyond theory into “and here’s how you can do this too” territory.

Part of this is probably everyone's current fear of falling behind due to the crazy pace of innovation happening right now, but I think the other part is that the webinars are actually giving value now. They used to pretty much just be boring sales pitches that were filled with promises + generic overviews, so this switch to specificity + “how to” is what people actually care about.

Let the learning continue

As you can tell, I’m back in my happy place. Lots of exposure to the market to see what’s going on + how we marketers can stay ahead/use it to our advantage.

If you feel like you’re stuck on something or unsure if it’s a “your company” problem vs. a broader “market” problem, I have space for 1 more client until I’m booked up through Q1 of 2027. Reply back here, send me a DM on LinkedIn, or feel free to drop me an email at sam@derevaco.com.

See you next week,
Sam

You may have thought you were going crazy + that despite scaling your ad spend on LinkedIn because “it’s working,” performance was staying relatively flat…well, this may be a big reason why.

I was chatting with Keith Putnam-Delaney (Co-Founder + CEO of Primer) the other week + he dropped that stat on me. I knew costs had been trending up for awhile, but I never zoomed out over that kind of time horizon to see just how much costs had inflated there.

Well, turns out he was right, AND that 200% may even be a conservative number (below are the CPMs we had in my last role when looking from 2024-2026 - a 255% increase despite my neurotic oversight on optimization + efficiency 😅).

Even with these rising costs, 94% of B2B still advertises on LinkedIn because…well, most audiences spend at least some time on there or it’s the only way we can have a reasonable level of confidence that we’re targeting the right people.

So we have rising CPMs (cost per 1000 impressions), ever-increasing CPLs (cost per lead), more competition entering the ad auctions, an ungodly amount of slopdusting all over the feed, + one more thing - their attribution is getting worse too 🙃.

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Sponsor: Primer

Outbound is broken + LinkedIn somehow keeps getting more expensive. Now what?

Every B2B marketer is paying premium prices for the same shrinking pool of attention on the same two channels (LinkedIn + Google).

Meanwhile, channels like Meta, YouTube, + display cost a fraction of LinkedIn…but most B2B teams can’t use them. Standard account lists match at 15%, AKA audiences are too small to learn + too noisy to convert.

Primer fixes the match rate problem. They turn your ICP, target accounts, and net-new prospects into 45-85% matched audiences across every major ad platform. Now the efficient channels we couldn’t use before due to low match rates are suddenly usable.

Get started with a free account + 30-day trial of paid plans today!

Fun fact: Rippling credits them for their $145M Series B success.

Try Primer today

Wait, how do we know where to invest then?

I promise I didn’t set out for this to be a newsletter that bashes on LinkedIn, but this initial context is important to understand why we’re seeing the budget + channel shifts that we are.

Across all of the customers Primer is hooked into, Keith stumbled onto something really interesting:

"What's really interesting is the LinkedIn click identifier data is actually getting getting worse.

So for whatever reason, across most of our customers, we're seeing that your ability to attribute conversions to LinkedIn is actually degrading, whereas it's sort of staying flat for Google and Meta, which is weird."

More specifically, this is the underlying analytics metadata that the data is degrading. Ad platforms always over-report their impact (hence why we’ll see 3-5x more “conversions” in ad platform reporting than we do in something like Google Analytics or Dreamdata). So whether it’s LinkedIn becoming less effective at converting users, an increase in cookie + script blockers, fewer purchases being made in today’s economy, or any combination of the above, the ROI here has been steadily rising for a few years + companies are finally being forced to think about where they should invest their ad dollars to get the most bang for their buck.

So where’s the budget moving to?

Meta (AKA, Facebook + Instagram).

"We're seeing budget move into Meta for the first time. More in the last nine months than the previous period.

So B2B is starting to make its way to Meta and we've seen about a 5-10 percent, depending upon the cohort, rise in investment in Meta."

Interestingggggg…

But also not. When channels start to lose their efficacy, we demand gen marketers are always on the hot seat thinking “oh shit, here we go again. I just figured out our channel mix that works + now a new wrench has been tossed in.”

Hey, that’s why we love what we do right? Never experience the same day twice + always new problems to be solved.

So based on the initial insight of the newsletter that LinkedIn costs are absolutely taking off, I assumed that the budget that’s migrating over to Meta was either 1) being repurposed from LinkedIn or 2) additive ad budget.

Wrong.

Enter curveball number 2 from Keith:

"Actually some of it's being pulled from Google, not just LinkedIn. We've seen about a 4 point drop in budget towards Google.

Which kind of makes sense, right? AI overviews are making it harder to make Google paid search work, I would say.”

We have LinkedIn costs rising 200% + Google’s AI overviews cannibalizing their paid search results, sooooo where is it exactly that we’re supposed to go to reach our market and be able to prove some type of ROI at this point?

Well, sometimes what’s old becomes new again…

Hello Moto Meta

(sorry for the bad throwback Motorola ad reference there)

Take me back to 2020, give me $25k, + I could drop all of that into Facebook Ads AND be able to tell you exactly what every penny drove. Lots of attention was being spent there, they had solid targeting options, and their conversion tracking was MONEY.

Over the following couple of years, first their targeting options were slowly pulled back, then Apple rolled out a new iOS that led to the majority of users opting out of app-tracking capabilities (AKA how Facebook was able to connect the dots between ad dollars + conversions), and that 1-2 punch was enough to drive a lot of B2B ad dollars over to a then-affordable LinkedIn Ads platform.

Alright now that that history lesson’s out in the open, let’s talk why we’re bullish on Meta now.

Audience matching capabilities

In B2B we have lotssss of data. Work phone numbers, work email addresses, work physical addresses, work IP addresses, basically Rihanna wrote a song all about the type of data we have on our buyers (I’m so sorry about the terrible references/dad jokes today - but hey, it’s how you know these aren’t AI-written? 😅).

ANYWAYYYY - long story short, we have TONS of work-specific data, but guess who signs into Facebook, Google, YouTube, Reddit, etc. with their work email?

NO ONE.

And that explains why contact list uploads to the above platforms are usually around 10-20% max - there’s no data to match to since no one registers their work email to those platforms.

But if there’s one big thing I learned during my time at Loxo it was that personal contact info (email, phone, etc.) is out there + accessible, historically it’s just been more expensive + harder to validate, but for a recruiter to be successful in getting someone to leave their current job, they’ve found it’s often not ideal to try and poach them via their current employer’s work email.

So as data has gotten better + more accessible, that’s where B2B data platforms are starting to catch up + is something Keith geeked out a bit on when he said:

"When we sync an audience into Meta, right, we use work email to start, and then we also use the personal emails we're able to find on the individual.

Then we use the mobile phone number. And the individual's zip code, not the company location, but the individual location, as well as things like gender, date of birth, as these are all things that help contribute to an improved match rate, especially on platforms like Meta.”

More simply put - multiple datapoints > 1 low match rate datapoint.

The algorithm (Andromeda)

Ever scroll through Instagram Reels + within 30 seconds are already finding that the videos coming up next are only the ones you’re interested in?

That’s Andromeda at work.

Countless variables + metadata are assigned to every video loaded in + as you watch certain videos (and scroll past others), those datapoints are quietly being (jk, just making sure you’re still paying attention) stored on the back end to help form a picture of you.

What topics you’re interested in
What job function/role you’re likely in
What hobbies you have
etc.

And those are just what it shows you in terms of the “big buckets” (if you’re curious about yours, head to “Settings and activity” > “Content preferences”), not all of the minute details that it also looks at (AKA your location, etc.)

All of this leads to a very tailored algorithm that can let you operate with a bit of a “Jesus take the wheel” approach regarding your audience targeting.

Real talk - earlier this year, I tested this out + was blown away. I ran two campaigns where the only difference was the audience targeting.

Audience 1 = contact list upload of individuals I knew were in our ICP + I had personal email addresses for, so we had a ~65% match rate

Audience 2 = only criteria was that they were located in the US and were > 22 years old

Within a week, to my complete astonishment, audience 2 was beating audience 1 across the normal platform KPIs:

• CPMs were lower

• Engagement rate was higher

• More conversions

• CPL was lower

Wild, right?

One thing I will say is that the conversions were slightly lower quality (algorithm isn’t perfect after all), but even after accounting for those, the performance was still better than the “old way” of targeting on Meta.

Or as Keith put it, “people are looking for cheaper inventory, and they’re willing to accept a little less quality.”

What this means for you

If you’ve been “doing things the way we always have” (or at least the same way the past 3-4 years), run some experiments.

Be open to trying out Meta again. Try out open targeting + leveraging Andromeda to find the right people. If you have the budget, acquire personal contact info for your ICP + upload that list directly.

When buyers fled to LinkedIn, that left a lot of inventory on Meta + drove their costs down from their peak in the early 2020s. While this isn’t a silver bullet to your demand gen plans, after playing around with it for a little bit + optimizing, your ad dollars will be able to go a lot farther here than on LinkedIn or Google.

See you next week,
Sam

When Keith Putnam-Delaney (Co-Founder + CEO of Primer) reached out about working together + one of the first things he said was, “Ideally we're interested in something that adds value to your followers and feels organic, less like a promotion,” I knew the match for us was there. So this week Keith + I recorded a ~1 hr convo that hit on everything from rising LinkedIn Ads costs + attribution degradation, why B2B measurement is perpetually behind B2C, audience matching as a moat, budget shifts we’re seeing across channels, brand differentiation in 2026+, and even some “human” bits 100% unrelated to marketing but things we’ve all struggled with.

Sharing all of that because:

1) Today’s newsletter expands on one specific part of our conversation (audience + brand moats)
2) I’ll have the full convo edited + ready to share hopefully next week (#one-person-team-probz 🤷‍♂️)
3) We’re working on a longer-term collab where I’ll be able to start using Primer myself so I can share real findings + tips as time goes on

Alrightyyyyyy then - onto today’s topic: the 2 best moats in B2B today…

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Sponsor: Primer

Bet you didn’t see that coming after that intro 😉

Outbound is broken + LinkedIn somehow keeps getting more expensive. Now what?

Every B2B marketer is paying premium prices for the same shrinking pool of attention on the same two channels (LinkedIn + Google).

Meanwhile, channels like Meta, YouTube, + display cost a fraction of LinkedIn…but most B2B teams can’t use them. Standard account lists match at 15%, AKA audiences are too small to learn + too noisy to convert.

Primer fixes the match rate problem. They turn your ICP, target accounts, and net-new prospects into 45-85% matched audiences across every major ad platform. Now the efficient channels we couldn’t use before due to low match rates are suddenly usable.

Get started with a free account + 30-day trial of paid plans today!

Fun fact: Rippling credits them for their $145M Series B success.

Try Primer today

“The only moat your competitors can’t copy is targeting”

This was one of Keith’s main points in a conversation he had a few months ago with Sophie Buonassisi on The GTMnow Podcast. So when I dug into that more with him, here was what he had to say:

“You can see the ads your competitors run. You can look at their website and you can see their messaging...

What you can't do is figure out what did they input into their ad platform, what lists are they working off of.

You could see that they're running Google search ads, but you can't know if they're using a massive suppression audience to weed out the chaff...that's what I mean by it can be a really big differentiator."

We geeked out on this for a bit + when I asked him what some of the top 1% marketers were doing here, he shared a few examples:

• Using contact-matched audiences on LinkedIn because LinkedIn doesn't 100% respect job title filters natively (IYKYK) - they almost always expand your audience or don’t have clean ways of bucketing titles so you get random people pulled in.

• Some marketers use matched audiences as a signal in a PMAX (Google Ads) + then having a massive suppression audience as well. So they’re effectively saying, “hey, algorithm, work your magic, find people like this, but whatever you do, don't serve ads over here."

• A handful of marketers are going after their target accounts via household IP addresses + trying to upload those into CTV platforms so they can run ads to them through the big screens

  • A friend of mine worked at a company that even had matching technology where once it knew IP addresses or a single device ID from tracking, they’d run their systems overnight at those locations to see all of the device IDs sharing that same IP address or location to then hit them on every device they could map to.

And while I loved riffing through these with Keith, it ultimately led me to asking him a larger question I’ve been thinking about lately…

How do we leverage brand as a moat?

This is one of those questions where on the surface, we’re like, “oh it’s easy, just have a POV, show personality, make your market want to associate with you, etc.,” but when we think about getting that into practice, we realize it’s one of those “much easier said than done” things.

B2C does an incredible job here but B2B…not so much.

We struggle to say + show what our brand stands for. Startups usually do a much better job of this than larger/established companies because that's ultimately how they differentiate. But as companies grow, as they go public, take on investment, get more customers, etc., everything gets watered down.

So I asked Keith about this. I mean, he is leading a startup as we speak, so I’d say a good subject to run this hypothesis by. Here’s what he had to say:

“I do think there are [other moats beyond targeting]. And I think brand can definitely be one of them. It can be a huge differentiator and create this cult like following.

I think it's actually harder than ever and more important than ever to do this because of the AI slop that exists. There's so much content, and then it’s how do you stand out in that sea of content?

I don't know if we've done a great job of it, personally...it is something I've been thinking about more lately, which is how do we create standout content that kind of breaks through the noise?

Here’s my theory:

1. Like Keith said, the rise of AI slop flooding our feeds + inboxes has us tuning things out more quickly (or slopdusting, as I’ve more recently termed the act of dumping a pile of unreviewed AI slop/lazy AI content on someone + walking away, leaving them to figure out what it even means)

2. The fear of pissing off 0.01% of the market + having your brand put on blast by a very tiny, but very loud, minority as a result

3. The rate of change in today’s market is so fast that there’s always a new technological advance you have to jump on (AKA every “AI-native” company right now…) or trend you want to speak to in order to capture the attention companies so desperately need

4. …while also balancing the fact that repetition is one of the most persuasive things you can do as a marketer, so if you’re constantly changing your positioning, value prop, taglines, etc., you’re actively making it harder for your audience to remember you

So how do we reconcile all of this?

Dual POVs: the durable POV + the adaptive POV

This is something I was struggling with for a while + it finally clicked for me a few weeks ago. How do we stay relevant as a company with market expectations (the “are you AI-native?”) while not losing our true roots + what makes us unique.

As every company jumps to say they’re AI-native, while that checks one box for the market of, “I need the software to be AI,” all that’s really been done is that the prospect has added another checkbox to their criteria list that 9/10 companies check. So you’re left there in what’s still a large pool of competitors + competing on features, price, etc. AKA, the commodity rat race.

But when I think about the brands I’m loyal to (and this list is almost entirely B2C), it goes to brands like Apple, Free Fly, Nike, YETI, etc. because I know exactly what I’m going to get from them AND what their message/brand says about me via association is what leads me to buying/staying with them.

Name a B2B company that has a strong point of view, truly unique values, and a position they willingly stand behind despite knowing it means a good chunk of their precious “TAM” will never buy from them. I’ll wait…….

Stumped? Me too.

Anyway - where this led me was thinking about how this looks from a long-term state. Talking 5-10 years here (and yes, that even accounts for today’s pace of change mentioned earlier).

BUT, while thinking about a 5-10 year window, how do we also make sure we’re staying relevant today or have the agility to act quickly when needed?

A lot of B2B companies are all of a sudden AI this, AI that, AI-powered, AI-native, etc. + that over-indexing is completely overriding a lot of their historical POV and value prop.

Where I’ve come to reconcile this is where I call the long-term POV the durable point of view. This is the POV/belief that everything is anchored on. It's memorable, it's short, it's easy to repeat, + it can survive marketplace changes well - hence, durable.

Then you have what I call the adaptive point of view, which is how you’re able to tie in what's relevant right now, so with the continued AI example, how we’re able to marry that in with our positioning.

Cool theory Sam, but what the heck does this look like in practice?

Durable POV:

Think about Nike + their infamous “Just do it” tagline. This is the belief Nike positions everything on. No matter what’s going on at the world stage, whether it’s the World Cup, Olympics, NBA Finals, etc., you’ll see this tagline being explicitly used or feel the emotion the tagline carries as part of the language used + story told.

Why this works as a durable POV:

1. The message is built for scale. It’s short, but the meaning is clear + visceral, especially after being repeated a number of times with various scenes taking place alongside it.

2. The message doesn’t hinge on any trending words or items so it can withstand the test of time

Adaptive POV:

For the 2026 World Cup, Nike ran their “Rip the Script” campaign. While “Just do it” wasn’t mentioned in the video, you can still feel the ethos of it in the content that came from the campaign.

Further, in true “adaptive POV” form, they tied in what’s trending now through the use of the most popular soccer players today (Mbappe, Haaland, Vini Jr., etc.) + cameos from individuals in culture today like LeBron James, Travis Scott, Kim Kardashian, Ted Lasso, Channing Tatum, etc.

When I was at Loxo, one of the adaptive POVs I was playing around with came from an ad set I pushed that said, “AI can never get a coffee with a candidate,” because our market’s fear was that AI was going to replace recruiters.

So how do you take this trending market concern + marry it with our more durable POV of empowering recruiters to make the very best hires possible for both the hiring company + candidate was the bridge I wanted to make there.

Why B2B struggles with this

I’ll cut right to it - lack of founder involvement.

The companies that truly nail the durable + adaptive POV balance share the singular trait of the founder being personally + non-negotiably involved in the brand.

Steve Jobs had a weekly meeting with Lee Clow (Chiat/Day) every week until he passed away. He was incredibly involved in all of their advertising.

Similarly, Phil Knight (Nike) worked closely with Dan Wieden (Wieden+Kennedy) on all of their marketing + brand efforts.

It’s a zero percent surprise to me that both of these companies have as strong + enduring brands as they do. And it’s no surprise because it started with the founder. This is the person who has the most conviction inside of a company. Often, the company is a physical manifestation of their personal beliefs + values. Whether you agree or disagree, love them or hate them, they’re going to share + carry themselves in the way that is most aligned to those.

These founders (and resultingly, brands), had very distinct POVs that they were also ruthlessly consistent with.

This is the hardest part for founders + companies today. The POVs get softened over time and/or they lose consistency by accidentally confusing their Durable POV with their Adaptive POV.

Write these down

What’s your company’s Durable POV?

What’s your company’s Adaptive POV right now?

If you don’t know these OR if they’re the same thing, that’s why growth may be struggling right now.

Figure these two out + everything cascades from there:

• Who your POV will resonate best with

• How to tie in what’s relevant today

• How to stand out despite all of the noise

• etc.

Stay tuned next week as I’ll pull out what we covered around budget shifts across channels we’re seeing in B2B and thoughts on how to set up an experiment to see what’s working 👀

See you next week,
Sam

I’m just about at capacity already (I cap things at 4 clients), which was the thing I was most nervous about in transitioning from employee > employer, but I’m incredibly bullish about what Affect will be able to provide at scale in helping marketers identify their growth constraints, enabling them with the knowledge to break past them, + then providing the “proof” that their decisions were right in the form of showing the outcome you drove (impact on the variable + resulting revenue over time).

All that to say, I’m back in my happy place of working directly with marketers every day, so expect LOTS of more geeking out on all things in that world + drop me a line if there’s ever anything you want to chat through! Can reply back here (these come to my inbox) or shoot me a note at sam@derevaco.com.

Now with that mini-update out of the way, let’s pick things up where I left off a few weeks ago when I shared part 1 of 4 mental models to position any brand, in any category that focused on the “need to haves” and today I bring you part 2 that focuses on the “nice to haves.”

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Sponsor: Primer

Outbound is broken. LinkedIn is expensive. Now what?

Reply rates keep falling. LinkedIn CPMs are up double digits YoY. Every B2B team is paying premium prices for the same shrinking pool of attention on the same two channels.

Meanwhile, Meta, YouTube, and display cost a fraction of LinkedIn — and most B2B teams can’t use them. Standard account lists match at 15%. Audiences are too small to learn, too noisy to convert.

Primer fixes the match rate problem. We turn your ICP, target accounts, and net-new prospects into 45-85% matched audiences across every major ad platform. Suddenly the efficient channels are usable.

Rippling credits us for their $145M Series B success.

Get a free account and free 30 day trial of paid plans today!

Try Primer today

Nice to have x known brand

Alright, so your market knows who you are, but they don’t necessarily need to use you in order to operate.

For those in the tech world, examples of this combination would be something like a revenue attribution tool (e.g. Dreamdata) or direct mail/gifting tool (e.g. Sendoso). A company can fully operate without either of these, but when you have the data or capabilities of something like these, they can drive increased growth.

Now for the 4 mental models…

Main business outcome

Whereas a need to have is often a high-competition/crowded category player, nice to haves typically have fewer options in the space since economic cycles hit nice to haves harder than need to haves. That said, since that means you’re ultimately a “bigger risk, bigger reward” option, the outcome you’ll want to speak to is NOT resource savings, but increasing profits/making more money.

Since the market doesn’t technically need you, your outcome has to be one that basically says “hey, you may not need me, but if you do, you’ll make even more money” (or insert the major business outcome your market seeks). You’re additive to their tech/service stack, so in order to get approved by their finance + leadership team, you need to show the incremental impact you’ll make to their business outcome that makes it a no brainer.

Marketing angle

Similar to being a need to have, this is where we play into being a known brand more. While the market may not technically need your software/services, communicating that you’re a well-known brand + that others like them go with you when they do “splurge” on this nice to have is a card you’ll want to play.

Multiple companies trust you as shown by all of the logos you’ve worked with. You’ve helped so many customers at this point that you have a seemingly never-ending repository of case studies highlighting the results you’ve helped customers achieve. And for winning over the IT + Finance teams, you probably have a very secure + stable infrastructure so they won’t need to worry about downtimes or not meeting compliance.

This one isn’t sexy, but it doesn’t need to be. Very few companies are truly well-known or carry a strong reputation, so don’t be shy about pointing to your track record.

Brand positioning

I think this is the most underrated AND biggest opportunity place to be.

You aren’t needed, BUT you can drive disproportionate outcomes for those who choose to use you. This is the perfect formula for positioning yourself as a luxury brand.

No one needs a watch in today’s day and age, but Rolex absolutely dominates their category.
No one needs a luxury car when a regular car can get you from point A to B, but Rolls-Royce is the only option because of the quality + signal they give.

So when it comes to being a nice to have + you’re a well-known brand, make DAMN sure you’re providing as high-quality of a product/service as you can + orient everything around that. That becomes your moat. Anyone can enter the category if they want, but they’ll have to find a way to overcome your reputation + service level to dethrone you (aka gooooood luck with that).

Pricing

Building off the luxury positioning, I think you already know what I’m going to recommend here. You aren’t a necessity + you’re viewed as a luxury, so price accordingly. You should be aiming for the high end of the market (e.g. top 5-10% minimum).

The market is buying your reputation as they know they’ll be getting a white-glove experience/premium results. Instead of me trying to give a bad example of pricing psychology, I’ll let this passage from Claude Hopkins provide you with how + why this works:

We learned that people judge largely by price. They are not experts. In the British National Gallery is a painting which is announced in the catalog to have cost $750,000. Most people at first pass it by at a glance. Then later, they learn what the painting cost. They return and surround it. A department store advertised $100 hat, and the floor could not hold the women who came to see it. We often employ this factor. Perhaps we are advertising a valuable formula. To merely say that would not be impressive. So we state as a fact that we paid $100,000 for that formula. That statement, when tried, has won a wealth of respect.

Nice to have x unknown brand

And now we’re on the other side of the known/unknown spectrum inside of the nice to have space. The market doesn’t need you AND they don’t know you. (Wait, why are we doing this again???) Kidding, but you can see that our work is cut out for us in this quadrant.

Keeping the examples going from earlier for those in the tech world, examples of this combination might be something like a company that sends “handwritten” letters on your behalf to prospects/customers (e.g. lettrlabs).

Now for the 4 mental models…

Main business outcome

Like the known brand in a nice to have space, you’re still a “bigger risk, bigger reward” option, so the outcome you’ll want to speak to is NOT resource savings, but increasing profits/making more money.

The market still doesn’t need you, nor do they even know you, so your promised outcome has to be an even more emphatic “hey, you may not need me, but if you do, you’ll make even more money” (or insert the major business outcome your market seeks). You’re additive to their tech/service stack, so in order to get approved by their finance + leadership team, you need to show the incremental impact you’ll make to their business outcome that makes it a no brainer.

Marketing angle

This is a tricky line to navigate, but what I’ve found is that if you want to be successful in this quadrant, you need to lean toward the extreme ends of the spectrum as you’re getting things started.

While the known brands are relying on their reputation + time in the space, the upstarts here have a window in time where they can come in with “fresh eyes” or a unique + strong POV.

The “old way/new way” angle that works for need to haves doesn’t quite hit the same as a nice to have since they aren’t forced to use the tool/service + risk being left behind if they don’t. So this is where I usually go with one of two options:

1. Cost of inaction - what is the prospect leaving on the table if they don’t use you. Showing how much more money could be made + how that compounds over time can be quite compelling…

2. Get an edge on your competitors - you’re new + you’re a nice to have. That means 99.9% of companies aren’t using you…yet. Get a little cocky here + demonstrate confidence that you know you’ll be a major player as the years go on, so now is the time for a prospect to get a leg up on their competitors by getting started with you today.

Brand positioning

Similar to in the need to have space, you should still have fun with this one + one that can be done any number of ways. There’s no one best way to do this, but one that I’ve seen consistently work well is positioning yourself as an innovator/disruptor to the space. It works well with both the cost of inaction angle, the edge on your competitors angle AND the technology adoption lifecycle curve by attracting the innovators + early adopters. Like I noted in part 1 for the need to haves, while this group may only make up 16% of the total market, they’re the ones who help build some serious momentum + positive word of mouth, so the faster you can attract them + allow them to be more successful than they were with their previous vendor, the faster your acquisition flywheel will go.

As a bonus, when you choose to position yourself as innovative + disruptive, that allows for you to be more aggressive with your branding + have a strong POV to communicate to the market. But instead of going too against the grain + divisive, knowing the long-term goal is to be a well known brand in a nice to have space, you’ll want to have an end goal of being positioned as a luxury brand, so that’s what you’ll want to really lean into with early positioning.

Pricing

So we’re in a nice to have space that may not be too crowded, but doesn’t have a ton of buyers all the time either. We’re going after the innovators + early adopters who are willing to take more risk in order to capture an increased reward on the backside of it.

In order to capture marketshare in a reasonable time + convert the business-oriented decision makers signing the contract, one thing that almost always makes it more palatable for them is if the cost is one that won’t cause any major issues should things not pan out. You don’t want to go crazy and severely undercut the competition as you’ll be viewed as a discount product/service, but being able to say to a prospect that they’ll save 10-25% from what they’re currently paying for the same/better outcomes can be compelling. Or, if they aren’t using anything yet, by showing how quickly they’ll 1) breakeven and then 2) become profitable after getting started with you, is a good way to dispel any potential concerns they have.

Note: make sure you run the numbers on your overhead + acquisition costs so you aren’t looking at a CAC payback period that’ll have you upside down for 3+ years. Technology + knowledge is advancing faster + faster, so whereas many companies used to be changing key providers maybe once every 5-8 years, this has moved to a 2-4 year window now, so if you aren’t profitable within that time, your business won’t be around for too long…

Bonus: how to identify + leverage your unique force multiplier (aka your brand coefficient)

Whether you already are a known brand OR are a relatively unknown brand, what you’re known for + the reputation you carry can quickly erode (for known brands) or be built (for unknown brands).

While few products/services ever move from truly nice to have to a need to have, one thing that is VERY much in a company’s control is their movement from an unknown brand to a known brand.

Why this is important is because of what I call the brand coefficient.

Quick: you need to make a recommendation for a sales CRM for your company RIGHT now, who are you recommending?

That’s brand at play.

I’ve spent years optimizing funnels and improving all of the demand levers available to us.

Cost per demo? Tighten the targeting to true ICP + watch wonders happen.
Demo - SQO rate? Let the prospect schedule the date/time of the demo when filling out the form.

The list goes on + on. But when you zoom out + look at larger datasets, there’s also a more binary variable that I can apply to quickly assess how strong a company’s funnel is:

Their brand coefficient.

If no one knows who you are or they don’t trust you, you can have all of the right demand optimizations built into your funnel, but it’ll still be a weak funnel.

Then on the flip side, if you have a strong brand + people trust you, you can have just some of the right demand optimizations built into your funnel and/or mediocre demand gen tactics in play, and it’ll be a stronger funnel than the one above.

This is the X-factor that takes a prospect from “I know what you do + I know why I should choose you”
to
“I know what you do + I know why I should choose you + I want to choose you.”

This is the force multiplier (aka coefficient) of having a strong brand.

There’s no one right way to build your brand coefficient - it’s unique for every company.

Some companies do it through high-touch, high-quality service (think: Four Seasons)
Some companies do it through a very unique personality (think: Duolingo)
Some companies do it through an emphasis on expert knowledge (think: Refine Labs)

Once you recognize what yours is (or could be), start rolling that snowball. It’ll take time to build up, but that single factor will be what gradually widens your funnel, improves your conversion rates, makes sales conversations easier, and turns raving customers into your biggest acquisition channel as they tell peers about you.

Quick question before we wrap:

See you next week,
Sam

Feels weird to write that out after spending the last 3.5+ years there. In some ways, it feels like just yesterday that I joined the team to build out the marketing program. In other ways, it feels like 35+ years there with all that the team experienced + accomplished during that time.

Early in my career (and to this day, TBH), I’ve always been curious about why people move on from companies. Were they actively looking? Was something going on behind the scenes? What factors did they weigh in deciding what to do? How + why did they ultimately make the decision?

So thinking about this + recognizing that these essays are ultimately for myself to “write” out loud + to come back to months/years later, now seems a pretty good time to reflect on those same questions for myself. And hopefully in going through this, it’s helpful to some of you reading this, now or in the future. Whether it’s to be used as sound advice or a cautionary tale in what not to do, that’s for you to decide :)

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Sponsor: Affect

Affect is the framework for how I think about marketing accountability. The playbooks I’ve built from 15 years of seeing what works + what doesn’t and recognizing that the purpose of marketing isn’t to hit vanity metrics like MQLs, but to move the business.

Affect is for the marketers who have sat in a room where marketing celebrated surpassing its MQL targets while the business missed revenue. It’s for the marketers who want to be held accountable because they’re confident enough in their work to let the math speak for itself. It’s for the marketers who understand that clarity is earned, conviction is a choice, + being a force on the business is the only version of this job worth doing.

August is the last month to grab the founding member rate at $99/mo, locked in for life. A ton of enhancements are coming out in Aug, Sept, and beyond, so be sure to grab this before pricing goes up to $399/mo. Or, as one of the first users said:

“It’s $99 and cancelable after 30 days, it’s pretty risk-free. I pay more for an Uber to the airport.”

Claim founding rate - $99/mo

Why now?

I was going to start this off with some notes of appreciation, but putting myself in the shoes of anyone reading this + myself when I see/hear of others moving on, I figured we’d start off by addressing the elephant in the room:

Why are you leaving? And what led to that decision?

The simple answer: it was time.

To be clear, I'm not walking into the unknown here - I know what's next + everything’s lined up at this point. But one thing I’ve noticed over my career is that there’s this little thought/feeling that slowly starts to creep in daily at work. That something’s missing, or that I’m “slowing” down in terms of what I’m learning + executing.

There’s a Steve Jobs quote from a commencement address he gave at Stanford where he said "For the past 33 years, I have looked in the mirror every morning and asked myself: 'If today were the last day of my life, would I want to do what I am about to do today?' And whenever the answer has been no for too many days in a row, I know I need to change something."

That quote is about the closest thing I can point to that describes what this felt like. It wasn’t one specific thing/issue that set it off, just a slow accumulation of mornings where the honest answer to that question was no.

I also want to be clear on one thing - this was entirely my call. Nobody pushed me out + nothing went off the rails internally. We just had our biggest product rollout in history + are continuing to grow. This decision was me choosing to move on to what’s next.

The slightly longer answer: months’ worth of reflection, questions, discussions, and the longest pros/cons list I’ve ever made.

To keep using the Steve Jobs quote, I’d been reflecting on the “mirror test” for a number of months. A career decision shouldn’t ever be made in a rush or in a “peak” season of any specific emotion. Nor is it ever a binary decision where 1 criteria decides if I should stay/leave. So every day, I’d be running through countless questions + thoughts in my head like:

Do I stay + hope things get better on their own? Just wait it out?
Do I stay, but proactively try to make things better myself?
Do I say enough is enough + leave without a plan, trying to figure it out after?
Do I stay until I have a plan, no matter how long that takes, despite the answer to the Steve Jobs mirror question being “no”?

Each of those questions carries a different type of weight. Risk, patience, trust, happiness, etc., and every week, the values/answers for each would change.

So me being me, I did what I always do when I don’t have a good answer for something or there are too many unknowns to make a decision - I created a framework to help me work through it.

One thing I’ve learned about myself is that I genuinely love + enjoy the “0-10” work (note: when I say 0, 10, 100, etc. in here, I don’t literally mean $10M, $100M, etc., using this more metaphorically). Getting a lay of the land, understanding the goals/outcomes we’re after, and putting a plan in place to work toward it. Then, and most importantly, doing the actual work to drive said outcomes.

I’ve always been very hands on in what I do. Living in just the strategy world sounds good in theory, but is very boring in practice AND since you aren’t executing anything, you never truly learn + understand if the strategy works. Nor can you iterate on things via the “fingertip feel” you can only develop via years of experience, failures, + first principles.

As things start to near the “10” mark, that’s often when teams start to get bigger, more cooks enter the kitchen, + the maturity of the company dictates that certain things need to change (as they should). And it’s then from the “11-100” type work that I find, while I can do it, it’s just not as much fun for me.

“Sam, please tell me you’re not about to say that when work isn’t as much fun as it used to be, that becomes the tipping point for when you start thinking about what’s next…”

🤷‍♂️

That’s exactly what I’m saying.

At least at this point in my career.

Naval Ravikant put this so eloquently + concisely that I’m just going to leave this 48 second video here so you can watch/hear it for yourself (I promise it’s worth it):

TL;DR = “find what feels like play to you, but looks like work to others”

In the early days of my career, I’ve always said eating shit is simply part of the path. There will be jobs I don’t love, tasks that are far from enjoyable that need to be done, people I won’t like working with, + so on.

BUT, that doesn’t mean all of those things aren’t valuable. They’re experiences that helped me orient around what I do like to do and would use as waypoints as my career progressed to gradually put me in places + positions I did enjoy and would succeed in.

So I think this segues well into the second part of the question…

How’d I make this decision?

It’d be easy to say there’s always 1 silver bullet that makes the decision for you. That you’ll get paid more, or that the hours are better, or that it’s working with a company/leader on your “dream” list.

But even when I’ve been offered a salary that’s 2-4x your current rate, or at a company with an incredible leader, I’ve found that those still don’t make the decision for me. That the timing isn’t quite right because I haven’t learned what I need to in this role, or that the team you’re already a part of is truly special and greater than that one individual leader/company.

So in reflecting back on how I made this decision to move on to what’s next after Loxo, I thought I’d share the incredibly over-thought, over-analyzed, over-everythinged things that passed through my mind, were written down in list after list, + anything/everything on top of that.

While at first, most of us would go to drafting a list of what we do want in a future role, I’ve found it’s actually helpful to first start off with what I don’t want in a future role. And back to a few paragraphs ago, this list is often fueled by all the experiences I’d had to date + noting what I didn’t enjoy so I could make sure I avoided that in the future.

And this is what led me to my first list of “absolutely-nots” for deciding what’s next:

• No publicly-traded companies (too much short-term decisionmaking due to quarterly earnings reports)

• No VC-backed companies (similar to the above, lots of decisionmaking to grow/scale at any cost + seeing some where ethical behavior is viewed as optional)

• Not serving a market where the ICP/buyers are unprofessional (rough mental model for this is “did the individual I sell to go to school to get into their profession?”). This one might ruffle some feathers + is 100% opinion on my side after experiencing selling to those who did/didn’t do this.

• No role where the expectation was simply to be a “channel executor” vs. someone who looks at the entire growth ecosystem to understand the best way to acquire new customers. This one pairs nicely with the common adage of “don’t work for a CEO who doesn’t get marketing”

• No role where I wouldn’t be paid more than what I’m currently making (because inflation + supporting a family 🤷‍♂️)

• No huge teams. As I noted above, I like the “figuring it out” stage of things vs. “scale what’s working + don’t question what’s working because it’s what we’ve always done” environment

Only 6 items, but they whittle the list down a LOT. And in reading between the lines on all of these, that showed me what I was ultimately looking for were:

• Ownership + autonomy. Ownership meaning having some type of stake in the company + the results. Autonomy branching off of that meaning having the trust + authority to make decisions that I believe would drive the type of results that would benefit me as someone with an ownership stake.

• An environment where the “old way” is recognized as no longer effective + that improving upon this is not just what’s needed, but actively looked for to be solved by the role (and ideally, this is for both the market being served and the company’s view on marketing/GTM)

These two “lists” quickly gave me shortlists for what I thought would be the best environments for me to be in next. So once I worked through them + sifted various companies through them, I was able to then run them through the final grinder to help me see which opportunities truly were great, which were ok, and which ones may have sounded good (aka great pay), but when including all of the other factors, I could quickly see that that one benefit was far outweighed by other factors that I knew I wouldn’t enjoy.

So with that all in mind, here’s what “the grinder” looked like using the various criteria I wanted factored in to helping me make this decision:

Must haves

• Remote-based work (no mandatory days in office/relocation required)

• Total comp ≥ current comp

• Company has already established product/market fit

• No “90-day pipeline/revenue miracle” expected

• ≤ 1 layoff in the company’s history

• Love the actual day-to-day work itself

• Professional ICP

Strong preferences

• Direct leader is someone I respect

• Real autonomy in the role

• Internal transparency (decisionmaking, financials, etc.)

• Leadership trusts my strategy/philosophy

• Marketing is respected within the organization

• Strong category tailwinds

• Founding team created the company from their own conviction in the product/service (not simply seeing where the most market $$ is available)

• Customers truly love the product/service + actively praise it to peers

• Product/service I have enthusiasm about/happily geek out learning

• Upward comp trajectory

• Some type of equity (ownership, shares, etc.)

• High quality team (skills AND as human beings)

• Long-term founder commitment (not looking to cash out ASAP)

Nice to haves (I had 20+ here, so just sharing a few as examples)

• Personal brand compatibility (day-to-day fuels what I learn + share via these newsletters, on LinkedIn, etc.)

• Continuous learning opportunity

• Internal culture of heavy peer collaboration/knowledge sharing

• Sell to a single ICP (not multiple)

• Company has a strong reputation in the market

The hardest part

This is the part I skipped above. The “shoutout to my incredible team” paragraph/appreciation bit is what’s expected because it’s the politically correct thing to do. List off the company leadership, how much you grew during your time, yadda yadda…basically something safe + forgettable.

The honest to god hard part for me are the team members I won’t get to talk to every day. One thing that was unique + special for me in this role is that in growing the team from myself as a solo-marketer to a team of 10, I recruited/hired every single member. No one was “inherited” or mandated as part of my team, so in being the final decisionmaker for hiring here, they were all people I knew I would want on the team + enjoy working with every day.

And call me crazy, but I actually care about my team. An easy 25-50% of our weekly 1:1s were NOT about work. I wanted to learn what they cared about outside of the 9-5 here - what their hobbies were, hearing the fun family dynamics most have with spouses and/or kids, what personal goals they had set for the year, etc.

One team member is currently on a trip in Italy + we already have a call scheduled when they’re back so I can hear all about it. Another team member is due to have their first child within a few weeks + most all of our conversations over the past month have been about that (and Chick-fil-A’s newest menu releases - IYKYK). Another member of the team actively tries to work themselves to the bone, so we had a bet going where if they didn’t get an agreed upon number of hours of sleep per night, they’d send me $20.

These are the conversations + dynamics I’m going to miss. They’re real relationships + like a friend who moves out of town, just because the proximity may have changed, the actual decision to continue/end the relationships with each person is simply a matter of effort + maintaining them after the “work” 1:1s are no longer scheduled.

So why am I sharing this section? As you can tell, it’s not for them as I’m not sharing any names here. I’m sharing it because the team was what kept me in the role far longer than I would have had those incredible relationships not been in place. This is always the hardest part of voluntarily leaving any company + is one I’ll always say not to underestimate. I know I shared the whole “list” above for how I looked at each potential company, but one thing that is missing from that is the “stay” column for Loxo + the weight that the single row of “team” carried was far greater than any + all of the other rows combined.

What’s next?

A week of digital detox.

Going to stash the laptop in a cabinet + spend lots of time with family, putting a dent in a stack of books I’ve been wanting to read, + some good old fashioned manual labor/work around the house. It may be weird, but as someone who lives in a very digital world, there’s something cathartic to seeing an improvement between the before/after of something tangible.

That said, no newsletter next weekend + stay tuned the following week as I’ll share where all of the above thinking + analyzing led me to 🤗

See you next week,
Sam

P.S. know a marketer who’d enjoy these newsletters as well? Reply back to this email (so I get it) + cc them on it. As a small thank you, I’d be happy to help answer any questions you have or hop on a call sometime for a fun marketing session :)

1. How to market a “nice” to have vs a “need” to have

2. How to market a known brand vs an unknown brand

Both spectrums have their pros + cons. Some are more vulnerable to economic cycles, some to advances in technology, etc. Over the years I’d find myself thinking something like “If only I could be working for a “need” to have instead of a “nice” to have, we’d be seeing much better results,”…only to find that when finally given the opportunity to be on the other side of that spectrum, the grass wasn’t as green as I thought + I had entirely different problems to solve.

But as I’m zooming out + looking at this intersection of nice/need to have x being a known/unknown brand, there are a few principles + mental models I’ve learned over the years that, while certainly not perfect, are often pretty good starting points to use after charting where your company is on the chart. The mental models for each of these that I’ll break down are: identifying the main business outcome to market, the angle you take, the overarching positioning for the brand, and how to think about pricing.

Two notes before we dive in:

1. A ton of people reading this will disagree with what I share - GOOD. No frameworks or playbooks should be viewed as dogma or set in stone. These are simply some good starting points that I’ve learned over the years to determine if said framework/playbook/mental model is the right path to continue on OR if we should look at it + say “nope, that definitely ain’t it.”

2. While using this matrix, also remember that your company is evolving as time goes on as well. You’re probably going to move along one or both of the spectrums as time goes on and/or work for different companies over the years that occupy differents spaces on the axes

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Sponsor: Affect

Affect is the framework for how I think about marketing accountability. The playbooks I’ve built from 15 years of seeing what works + what doesn’t and recognizing that the purpose of marketing isn’t to hit vanity metrics like MQLs, but to move the business.

Affect is for the marketers who have sat in a room where marketing celebrated surpassing its MQL targets while the business missed revenue. It’s for the marketers who want to be held accountable because they’re confident enough in their work to let the math speak for itself. It’s for the marketers who understand that clarity is earned, conviction is a choice, + being a force on the business is the only version of this job worth doing.

August is the last month to grab the founding member rate at $99/mo, locked in for life. A ton of enhancements are coming out in Aug, Sept, and beyond, so be sure to grab this before pricing goes up to $399/mo. Or, as one of the first users said:

“It’s $99 and cancelable after 30 days, it’s pretty risk-free. I pay more for an Uber to the airport.”

Claim founding rate - $99/mo

Need to have x known brand

In a scenario like this, you’re selling something that your market requires in order to operate, and those in the market have most likely heard of your brand before.

For those in the tech world, examples of this combination would be something like a sales CRM (i.e. Salesforce) or accounting/finance software (i.e. Quickbooks). While a company doesn’t technically need these in order to operate, they’re pretty much foundational infrastructure (unless you’re a masochist + enjoy doing everything manually in spreadsheets).

Now for the 4 mental models…

Main business outcome

You’re selling something that the market knows they need, so more likely than not, you’re playing in an existing category with other options. As a need to have, unless you’ve found some crazy technological advantage, you probably aren’t going to help the prospect to make more money, so of the 3 main reasons that anyone buys software/services (save time, save money, make money), that rules that outcome out as something to lean on. That leaves us with save time/save money, which we’ll merge into one for simplicity - save resources.

So whether that’s understanding that your sales CRM has a better UI + allows the user to accomplish their tasks faster, or that the accounting software is able to consolidate what used to be done across 2-5 systems into 1, this is where you’ll figure out your “bottom line” orientation that’ll go into the prospect’s business case that requires some form of ROI number in order to be approved.

Marketing angle

This is where we play into being a known brand more. You’re in a crowded category + the market needs your software/services, so one of the strongest things you can communicate here is that you’re a well-known brand. Multiple companies trust you as shown by all of the logos you’ve acquired. You’ve helped so many customers at this point that you have a seemingly never-ending repository of case studies highlighting the results you’ve helped customers achieve. And for winning over the IT + Finance teams, you probably have a very secure + stable infrastructure so they won’t need to worry about downtimes or not meeting compliance.

This one isn’t sexy, but you don’t need to be. Very few companies are able to live at this intersection of being a nice to have AND being well-known, so don’t be shy about pointing to your track record. There’s a reason the saying “no one ever got fired for buying Microsoft” continues to this day…

Brand positioning

So you’re a need to have and the market knows you. By being known in the industry, you’ve overcome one of the hardest challenges which is simply making it to the “recall” list for anyone in the market you serve so you have a near guarantee on making the shortlist for purchase. Play into that here.

Find a way to give off “premium” vibes if you can. Not just a “we’re here to rest on our laurels”-type vibe, but demonstrate that not everyone can use your software/services. That being a customer of yours gives off a signal to the customers’ market that they’re real business operators if they’re partnering with you. A good example of this right now is Vanta. Far from sexy category, well-known brand, and by slapping their credentials on your website, your prospects immediately know you take security + compliance seriously.

Pricing

Alright, rounding third + heading toward home. You’re a need to have, your brand carries weight, and you’ve demonstrated that there’s a bar to entry in order to use your software/service. That last part is what we’re going to leverage when it comes to pricing.

If you’re too expensive, the market will flock to more affordable options because you’ve priced yourself out of too many budgets. If you’re too cheap, it can leave the sense that the quality may not be there when they start using your software/service. So we need to meet (a little) past the middle here. When running market comps, you’ll want to sit somewhere between the middle + high end of the market. For example, if the average comp in your market is $1000 per month, it might be worth pricing somewhere between $1200-1500 per month. Remember: your market is buying your reputation - make sure you price that in + don’t sell yourself short.

Need to have x unknown brand

Now we’re on the flipside of the known/unknown spectrum when competing in a “need to have” category. The market still needs what you’re selling in order to operate, BUT you aren’t familiar to most of them yet. You may be a newer entrant or expanding into an adjacent market that you hadn’t previously served.

Continuing the example from earlier for those in the tech world, examples of this combination would be something like a sales CRM (i.e. Attio) or accounting/finance software (i.e. Mercury). While a company doesn’t technically need these in order to operate, they’re pretty much foundational infrastructure (unless you’re a masochist + enjoy doing everything manually in spreadsheets).

Now for the 4 mental models…

Main business outcome

Still playing in the “need to have” space means it’s unlikely that you have a unique differentiator or value prop that finds a way to help your market make significantly more money than the alternatives, so you’ll most likely continue playing on the resource savings (time/money) outcome here.

Pretty similar rundown to what was shared above when you’re a known brand, so what was shared in there will transfer near equally to an unknown brand.

Example: Attio in the sales CRM space. Crowded category, big name incumbents, they’re newer + leaning hard into time savings + a more efficient workflow.

Marketing angle

Now is where we get to start having some more fun. Being a more unknown brand in a need to have category most likely means you’re a newer entrant to the space or have innovated your way in from an adjacent space. While the known brands are relying on their reputation + time in the space, the upstarts here have a window in time where they can come in with “fresh eyes” and help paint that picture for the industry.

This often comes in the form of “old way/new way” messaging where you point out the way things “have always been done” as the old way, and then present a new way - often one that is faster, more efficient, and/or more cost-effective than the old way. I’ve used this one a few times over the years by using a simple table that contains a few use cases/jobs-to-be-done for the market and has the old way of doing it on the left hand side + the associated cost (time/spend), then on the right hand side the new way of doing it + the associated cost (which will always be an improvement on the old way if you’re showing it in this table.)

Pro tip: the old way/new way table is great, but an even better move is when you can present this in the form of the “cost of inaction,” i.e. what is the prospect leaving on the table if they don’t make a change. Showing how much time/money that could’ve been saved + how that compounds over time can be quite compelling…

Brand positioning

This is a fun one + one that I’ve seen taken any number of ways over the years by various brands. There’s no one best way to do this, but one that I’ve seen consistently work well is positioning yourself as an innovator/disruptor to the space. It plays hand in hand with the old way/new way angle you’d be using AND also plays well into the technology adoption lifecycle curve by attracting the innovators + early adopters. While this group may only make up 16% of the total market, they’re the ones who help build some serious momentum + positive word of mouth, so the faster you can attract them + allow them to be more successful than they were with their previous vendor, the faster your acquisition flywheel will go.

As a bonus, when you choose to position yourself as innovative + disruptive, that allows for you to be more aggressive with your branding + have a strong POV to communicate to the market. Innovators + disruptors rarely have logos + websites with the typical lethargic SaaS blue or watered down messaging. But as time goes on + you go upmarket, companies are often forced to “mature,” so now is the time to put a stake in the ground for what your brand is, and equally what it isn’t.

Pricing

Alright so we’re in a crowded category with legacy players who own most of the marketshare. We’re going after the innovators + early adopters who are willing to take more risk in order to capture an increased reward on the backside of it. And since this is a need to have, it’s probably going to overlap for some time with the incumbent or be scrutinized by finance to get to positive ROI quickly.

In order to capture marketshare in a reasonable time + convert the business-oriented decision makers signing the contract, one thing that almost always makes it more palatable for them is if the contract costs less than their existing one for the same product/service. You don’t want to go crazy and severely undercut the competition as you’ll be viewed as a discount product/service, but being able to say to a prospect that they’ll save 10-25% from what they’re currently paying for the same/better outcomes can be compelling.

Note: make sure you run the numbers on your overhead + acquisition costs so you aren’t looking at a CAC payback period that’ll have you upside down for 3+ years. Technology + knowledge is advancing faster + faster, so whereas many companies used to be changing key providers maybe once every 5-8 years, this has moved to a 2-4 year window now, so if you aren’t profitable within that time, your business won’t be around for too long…

What about the “nice to have” companies?

Stay tuned for part 2/2 of this series next week that’ll breakdown the “nice to have” elements of the equation + how to identify and leverage your unique force multiplier (or what I call the brand coefficient)…

See you next week,
Sam

95% of the meeting was filled with talking from individuals who didn’t seem to have any real point to make, but felt the need to speak frequently so their voice was heard.

And then there was 5% of the meeting where, when 1 or 2 specific people spoke, everyone shut up and hyperfocused on what they had to say.

I learned three lessons when that realization finally hit me:

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Sponsor: ALVA Studio

Picture this—a founder who just closed a $2M seed round. The product works, the team's sharp, the investors are in. Then a prospect pulls up the website and it looks like every other "AI platform for modern teams" that crossed their screen that week.

The team's heads-down on the roadmap, sales is chasing pipeline, and no one catches that the brand is making every conversation start from a half-step behind.

That's the thing about brand—it's never the fire you're putting out today. Until it's the reason a deal, a round, or a candidate went to the company that simply looked more real.

ALVA Studio built the fix for exactly this: a 4-week Brand Sprint that takes a funded B2B SaaS or AI company from interchangeable to inevitable. Senior team, direct line to the people doing the work, no six-month agency runway. Companies like Loxo, Accord and AceLab all saw jumps in conversion, brand credibility and analyst recognition post-launch. This is the natural next move once the product has outgrown the story around it.

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Lesson 1: Don’t be one of the 95% that speaks just to speak

I’m sure you immediately had a flashback to a previous job, a recent meeting, or even a few specific individuals when you read this. The person who needed to get to the point already. The person who seemed to take the classic improv advice of “yes, and…” too literally and was chiming in after every point someone else made. The person who, when starting to speak, you could see eyes in the room starting to roll.

The interesting dynamic at play is that, unless you’re in a small, discussion-oriented meeting, there’s often an inverse relationship between the amount someone speaks and how engaged the room is when they speak. Individuals in the 95% are the ones on the far right of this graph - lots of talking, few engaged listeners.

People subconsciously categorize others into buckets around this. There’s a reason those eyes start rolling after just two words. That person could finally be about to say something profound, but they’ve trained people that when they do speak, they usually don’t say anything profound or valuable.

And for those getting started in their careers, or those who are finally getting a seat at “the table,” speaking more runs the risk of saying something foolish that has others wondering why you’re in the room to begin with.

Lesson 2: When you speak less, more listen

Let’s have your memory flashback again to a previous job or recent meeting you’ve been in. Now think about the opposite of the above. Was there an individual in the room that, when they said something, you found yourself nodding along or thinking, “Wow, that’s a really [great point/interesting insight/good idea]!”

That type of commentary often comes from someone who’s been sitting back, absorbing the overall conversation, reading the room to see who is (and isn’t) in there, and is able to wade through everything so that when they have something to share, it’s highly relevant to the conversation.

This is the flipside of what the others do. And that is why these people are on the left side of the graph below - less time talking, but when they do they have everyone engaged with what they’re saying.

For those getting started in their careers, or those who are finally getting a seat at “the table,” saying fewer, but highly relevant, things solidifies anyone who doubts why you were hired or why you’re now at the table. The person who brought you on saw something in you that they now see. It also lends more weight to the items you share, so when people leave the room, they aren’t thinking about the 100 irrelevant things that one team member said, but are thinking about that 1 incredible point/idea you shared.

Lesson 3: This concept applies equally to your content strategy

There is a LOT of content out there. And to be honest, a lot of it is just noise.

It’s not a new idea.
It’s the same thing everyone else is saying.
It’s the thing that brought a spotlight on you/your company years ago, but is no longer relevant or novel.
It looks (content medium) exactly like everything else out there.
It doesn’t spur any further thinking from the recipient.
It’s consumed and the end user thinks, “Well, that’s 3 minutes of my life I’ll never get back.”

It’s the content equivalent of the person earlier who would speak just to hear their own voice.

I was re-introduced to Jay Acunzo’s content lately and I’m so glad I was as it helped me solidify this lesson. He has a strong POV on content, more specifically, a strong dislike of commodity content. He was able to map out a brilliant simplification for what this looks like in the B2B space.

Sam, what’s your point?

I saw a post on LinkedIn from an individual with a very large following. They were sharing advice about if they were to start over on LinkedIn, how they would do it. And then they shared this step, to which I nearly wanted to pick up my computer and smash it on the ground:

This is the antithesis of everything I’ve said so far in this newsletter. This is exactly what would have you living in the commodity cage that Jay outlined above. And unfortunately, this is what the majority of people are probably going to be doing over the coming years.

Using AI as the subject matter expert, not yourself
Using AI to write the content for you, sounding nothing like you
And then pumping out these content pieces daily, if not multiple times per day

This is the definition of how to become a false thought leader. This is exactly how to get people NOT to listen to you. This is the social version of the person who speaks just to hear their own voice.

Little expertise in the space you’re creating content about.
And not even writing in your own words or using the lessons you’ve learned in the content you’re producing.

Whether you’re creating content for your personal brand or for your company, this perfectly translates to both cases.

You can be the signal, or you can be part of the noise. You get to decide.

See you next Saturday,
Sam

P.S. know a marketer who’d enjoy these newsletters as well? Reply back to this email (so I get it) + cc them on it. As a small thank you, I’d be happy to help answer any questions you have or hop on a call some time for a fun marketing session :)

Well, let’s just say this one clearly resonated + drove some discussion around 2 things marketers should never forget:

1. Exactly what Ogilvy said - we get sick of our work well before the market does (most of them won’t have even seen it yet)

2. The best performing ads can still work just as well 1+ years later

So with this in mind, I decided to think back on ads/campaigns that have been successful precisely because of this - because they let the work marinate instead of iterating on it after 30 days.

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Sponsor: Affect

Affect is the framework for how I think about marketing accountability. The playbooks I’ve built from 15 years of seeing what works + what doesn’t and recognizing that the purpose of marketing isn’t to hit vanity metrics like MQLs, but to move the business.

Affect is for the marketers who have sat in a room where marketing celebrated surpassing its MQL targets while the business missed revenue. It’s for the marketers who want to be held accountable because they’re confident enough in their work to let the math speak for itself. It’s for the marketers who understand that clarity is earned, conviction is a choice, + being a force on the business is the only version of this job worth doing.

August is the last month to grab the founding member rate at $99/mo, locked in for life. A ton of enhancements are coming out in Aug, Sept, and beyond, so be sure to grab this before pricing goes up to $399/mo. Or, as one of the first users said:

“It’s $99 and cancelable after 30 days, it’s pretty risk-free. I pay more for an Uber to the airport.”

Claim founding rate - $99/mo

Geico’s gecko (27 years going strong)

Doesn’t matter whether it’s just a billboard or on a tv commercial, when you see this guy, you know it’s Geico.

Fun fact: Geico’s gecko first debuted on Aug 29, 1999 (27 years ago!) because of a screen actors guild commercial strike that prevented companies from using human actors. Talk about making lemonade when life hands you lemons…

Anyway - when you think of a commodity market, insurance is 100000% in that space. Ultimate race to the bottom + you can go to any number of providers to ultimately get the same exact product.

So how do you win in this kind of market? By being at the top of the mental shortlist when someone goes to shop. Whether because they’re mad at their current provider, are purchasing a vehicle for the first time, etc., most consumers already have a few providers in mind when the need arises.

Geico owns this spot with most of their market. They don’t out-feature their competitors or have any crazy cut-throat pricing discounts, they’ve just been maniacally consistent with this one character for 27 years + never stopped.

The gecko became Geico sheerly from repetition.

Amp’d Mobile’s 1 perfect ad

The first time I saw this commercial, I thought it was funny.

The second time I saw this commercial, I was waiting for the E-40 lines to be dropped.

The third time I saw this commercial, I was searching for it on YouTube because I wanted to see it.

Amp'd Mobile existed for a whopping 1.5 years. But in that time, they created one commercial that outlived the entire company.

Yes, it definitely only spoke to a certain demographic, but it was the exact one they were trying to attract. So to Adam’s comment in the beginning of this newsletter, put this one on repeat + it’ll continue to be one of the top performing ads no matter how many others you create after.

The mistake they made was that they tried to iterate off this commercial, so they made more funny commercials. Unfortunately, none of them landed like this first one.

This first one was the novel, but everything after it felt like a copy of a copy. Their second mistake was that they should have kept running this OG one instead of copies that never quite landed the same way.

Ultimately, this is the parade principle in action - most of their market hadn’t seen this “best” commercial before they were sick of it + iterating into worse versions of it.

What ads live rent-free in your head?

I’ve been going down an ad rabbithole lately + would love to hear/unpack some of these. Which one(s) are they + why you think they do? Reply back + let me know (Believe it or not, I read every single email that comes through.)

See you next Saturday,
Sam

P.S. know a marketer who’d enjoy these newsletters as well? Reply back to this email (so I get it) + cc them on it. As a small thank you, I’d be happy to help answer any questions you have or hop on a call some time for a fun marketing session :)

As part of this rabbithole tour, I’ve been going through the classics: Claude Hopkins, David Ogilvy, Gary Halbert, John Caples, etc. and have been filling up my notebook faster than ever before. Principles validated that we’ve been doing, foundational things I’ve found we’re drifting away from + need to come back to, and tactics that we hadn’t been using at all + put into our mix as soon as I finished reading the section.

After re-reading my highlights, I wanted to create some form of a lesson/takeaway that I could come back to as time goes on from each of these books. So today we have the second of these as I unpack my learnings + interpretations from “Confessions of an Advertising Man” by David Ogilvy.

Subscribe now

Sponsor: Affect

Affect is the framework for how I think about marketing accountability. The playbooks I’ve built from 15 years of seeing what works + what doesn’t and recognizing that the purpose of marketing isn’t to hit vanity metrics like MQLs, but to move the business.

Affect is for the marketers who have sat in a room where marketing celebrated surpassing its MQL targets while the business missed revenue. It’s for the marketers who want to be held accountable because they’re confident enough in their work to let the math speak for itself. It’s for the marketers who understand that clarity is earned, conviction is a choice, + being a force on the business is the only version of this job worth doing.

August is the last month to grab the founding member rate at $99/mo, locked in for life. A ton of enhancements are coming out in Aug, Sept, and beyond, so be sure to grab this before pricing goes up to $399/mo. Or, as one of the first users said:

“It’s $99 and cancelable after 30 days, it’s pretty risk-free. I pay more for an Uber to the airport.”

Claim founding rate - $99/mo

Culture

Real talk: it’s crazy to see how much things have changed in the 63 years since this was published.

How many companies actually help their employees when they’re sick or have health issues?
Have actual internal training programs to level up team members, not just a “learning stipend” to buy books or attend a conference once per year?
Operate with integrity in the sense of making recommendations that are what’s best for the client/customer, not necessarily for the company?

There are some out there that do exist, just one of those moments of reflection where seeing this on paper has you mentally going through the checklist of your current/former employers.

Clients/Customers

A couple of interesting points made in here by Ogilvy + speak to the conviction he held when it came to their clients.

I’m sure most everyone reading this has at some point had a client or customer they couldn’t stand working with, but would justify the stress of them because of the income they provided.

The 1 huge client that paid so much they effectively controlled the product roadmap…
The 1 huge client that paid the same amount 2 clients combined did…but was actually the work of 3 to manage…

These are the things we need to evaluate when it comes to clients/customers. It’s not always a function of dollars to determine if they’re worth engaging/keeping, but how that also expands out to the mental bandwidth they occupy, the second-order decisions made because they overweigh business discussions, etc.

Then as a cherry on top, I loved that last part of the quote about resigning accounts when confidence is lost in the product. Goes back to integrity here + not being willing to market something you actively wouldn’t use or recommend to others.

Consumers

Most of you have probably read/heard the first sentence of this quote somewhere before as it’s one of Ogilvy’s most famous. But it’s the second sentence that I think is the most important here as it’s something that still runs rampant today.

So many companies + brands lean on slogans and generalities and superlatives like “#1 in [category]” without ever providing any context or justification for those statements. It’s lazy marketing to do those + is why so many companies become commodities competing in a race to the bottom.

Consistency

If there’s one thing you remember from today’s newsletter, have it be this section. (and I say this because it’s what I need to continuously remind myself of)

Yes, frequency + ad fatigue are real, but I think we overindex on what the ad platforms recommend as “best practice” to the detriment of what’s actually working. For example, say you’ve got an ad that is absolutely KILLING it. I’ve seen marketers stop running it because it’s hit their frequency number that triggers a new ad/campaign to start running instead.

The unfortunate part of this is that the next ad/campaign are often for an entirely different product/feature, or is a different message/offer, so every bit of momentum gained from what was running WELL before is stripped out from underneath it.

And that’s why I love the simplicity + visual Ogilvy gives in the second part of the quote when he said, “You aren’t advertising to a standing army; you are advertising to a moving parade.” That mental model is one that once I read it, have told myself I will come back to every month so I never forget it.

Congruence

Since my Refine Labs days, I’ve always said the message NEEDS to match the medium it’s being placed on.

This is often the cause of so many “[channel] doesn’t work for us” claims we’d hear. Then when looking into why that channel wasn’t working, I’d see it was because they were taking something that was clearly formatted for a channel like LinkedIn and would take that exact same ad/content + push it over to a place like Reddit or YouTube.

Those channels operate ENTIRELY differently from one another in terms of how users consume + engage content, so it’s zero percent surprising that the “channel” didn’t work for them, when the reality was they were using the wrong medium/format within the channel.

Conclusion

Like I said last week, these principles work because they’re built on understanding human nature, not chasing the newest/shiniest trend. Ogilvy wrote this in 1963 (63 years ago!) and they’re still relevant. The mediums since then have changed (i.e. social ads vs. print), but the underlying fundamentals haven’t.

So that’s why I think going back to the classics matters. A lot of marketers are chasing silver bullets + trends that’ll only last for a few weeks/months, then it’s back to the drawing board to find the next one. There’s no consistency being built in how they’ll attract their market. The fundamentals in these classics prove there are other ways. If something’s been working for 63+ years, I’d be willing to bet it’ll probably continue to work for a few more years 😉

See you next Saturday,
Sam

P.S. cool new feature in Substack that detects AI writing in publications. Here’s what this newsletter scored on the “AI slop” scale 😜

Anyway, as part of this rabbithole tour, I’ve been going through the classics: Claude Hopkins, David Ogilvy, Gary Halbert, John Caples, etc. and have been filling up my notebook faster than ever before. Principles validated that we’ve been doing, foundational things I’ve found we’re drifting away from + need to come back to, and tactics that we hadn’t been using at all + put into our mix as soon as I finished reading the section.

After re-reading my highlights, I wanted to create some form of a lesson/takeaway that I could come back to as time goes on from each of these books. So today we have the first of these as I unpack my learnings + interpretations from “My Life in Advertising & Scientific Advertising” by Claude Hopkins.

Subscribe now

Sponsor: Affect

Affect is the framework for how I think about marketing accountability. The playbooks I’ve built from 15 years of seeing what works + what doesn’t and recognizing that the purpose of marketing isn’t to hit vanity metrics like MQLs, but to move the business.

Affect is for the marketers who have sat in a room where marketing celebrated surpassing its MQL targets while the business missed revenue. It’s for the marketers who want to be held accountable because they’re confident enough in their work to let the math speak for itself. It’s for the marketers who understand that clarity is earned, conviction is a choice, + being a force on the business is the only version of this job worth doing.

Founding member rate is still available - 41 left at $99/mo, locked in for life. Or, as one of the first users said:

“It’s $99 and cancelable after 30 days, it’s pretty risk-free. I pay more for an Uber to the airport.”

Claim founding rate - $99/mo

How to think about marketing

This is one that I realized I wasn’t doing a good job of.

I assumed the prospect reading the ad or hitting our landing page would be naturally curious enough to go to all the other relevant pages to learn all about our entire platform + the problems we could help them solve.

Nope.

This passage was the realization that many would only read what was put right in front of them + if that wasn’t compelling/insightful/helpful enough for them to go on reading, they’d leave. And while future ads would help bolster recall, they probably wouldn’t click/read anything since they already formed an opinion about us/our platform.

So after making sure the headline grabbed their attention + pulled them in, I drafted the supporting copy to round out the story AND then go on to speak to all the other outcomes that they desire.

Fun fact: CTR on this ad is 1.46% (avg LinkedIn ad CTR is 0.3%) + dwell time is 11.48 sec (avg LinkedIn ad has a 3.6 sec dwell time), so I think Hopkins was right on this one 😉

The power of show, don’t tell

This was something I noticed early on for us. We were creating a new category, so no one really knew (or cared) what a “Talent Intelligence Platform” was.

But as soon as I started dropping in 30-90 sec use case videos showing the different jobs-to-be-done our ICP encounters every day + how easily our platform handled those, that was when the lightbulb went off for our prospects + we spurred a ton of inbound demos.

Saying things like “recruit faster!” or “get better candidates!” aren’t unique + don’t mean anything to a recruiter who gets bombarded daily with those types of promises. But showing them how that could be done + in a manner different from what they were used to - that was where the magic happened.

Storytelling + specificity

Building off of show, don’t tell, when you do need to tell, do so with specificity. That is what lends credibility + weight to what’s being said.

It’s super easy to say things like “trusted by thousands of recruiters!”, but an entirely different thing to say “used by 10,200 recruitment firms across 23 countries.”

But one thing I’m still working on doing for us is taking Hopkins’ storytelling approach above to walk a prospect through that specificity. Helping them see the knowledge, thought process, etc. that fuels the product they’d be using. Understanding what insights + data were found that illustrate how we aren’t just another piece of recruitment software, but how it was built + curated uniquely for them.

That’s where a believer is made.

What NOT to do

This is one I felt in my bones with the rise of AI slop + oversaturated feeds recently. It’s harder than ever to stand out + gain attention, so the “easy” solution to this is to put on a monkey costume + dance.

Yes, that’ll work - you’ll get eyes, but not all eyes are good eyes.

This can be taken literally in the sense that you could be capturing the attention of individuals who aren’t in your ICP, so that attention doesn’t ever turn into any business.

But it can also be eyes watching this type of marketing similar to how one watches a car crash happening in real-time - you want to look away, but you can’t…

And this then turns into a negative association with your brand/product. An impression/view occurred, but if all it did was turn off the prospect + even burn them from ever wanting to buy in the future, is that the type of attention/impression you really want to make?

Why it works

There’s something about subtle confidence that just works well.

More specifically, when it’s future-oriented. Like how the second man in this story said “Try the horse for a week. Come and pay me then.” as he knew that the individual would be happy + buy it.

So I tested something similar. Presented an offer where there’s zero downside for the prospect. They send us the role they’re trying to recruit for + we come to the demo with that already loaded into the system, qualified candidates + their contact info + an outreach sequence ready to be turned on to pull them into the candidate pipeline.

Whether the prospect goes on to continue the conversation + buy or not, all of the info is theirs to keep after, no strings attached.

From our data, we know the rate at which prospects convert when they get to see the platform in action + with relevant examples to them, so this is why we’re able to lead with that type of subtle confidence here + why the time put into this ahead of time will always net out positively for us as this scales.

Wrapping up

These principles work because they’re built on understanding human nature, not chasing the newest/shiniest trend. Hopkins wrote this in 1923 (103 years ago!) and they’re still relevant. The mediums since then have changed (i.e. social ads vs. print), but the underlying fundamentals haven’t.

So that’s why I think going back to the classics matters. A lot of marketers are chasing silver bullets + trends that’ll only last for a few weeks/months, then it’s back to the drawing board to find the next one. There’s no consistency being built in how they’ll attract their market. The fundamentals in these classics prove there are other ways. If something’s been working for 103+ years, I’d be willing to bet it’ll probably continue to work for a few more years 😉

See you next Saturday,
Sam

P.S. cool new feature in Substack that detects AI writing in publications. Here’s what this newsletter scored on the “AI slop” scale 😜

I was getting good sleep, had a consistent training program, + followed a generally healthy nutrition/dietary intake. But I was still tired at the end of the day.

The long story short of it ended up being a pretty “simple” answer: my autonomic nervous system was running almost perpetually in its sympathetic (read: fight or flight) state vs a more balanced mix of sympathetic + parasympathetic (read: rest and digest) state.

So in typical nerd fashion as I wanted to truly understand what was going on AND what I could do to turn things around, I got a bloodwork test, reviewed all my WHOOP data, and had a good old fashioned self-reflection to see if I could sort through what was going on.

A bit of a departure from my normal marketing/GTM articles, but I’m sharing this as it’s a trend I’m seeing/hearing from a number of friends + peers in the space - they’re burning out faster than ever + not sure what to do about it.

Subscribe now

Sponsor: Affect

Affect is the framework for how I think about marketing accountability. The playbooks I’ve built from 15 years of seeing what works + what doesn’t and recognizing that the purpose of marketing isn’t to hit vanity metrics like MQLs, but to move the business.

Affect is for the marketers who have sat in a room where marketing celebrated surpassing its MQL targets while the business missed revenue. It’s for the marketers who want to be held accountable because they’re confident enough in their work to let the math speak for itself. It’s for the marketers who understand that clarity is earned, conviction is a choice, + being a force on the business is the only version of this job worth doing.

Founding member rate is still available - 45 left at $99/mo, locked in for life. Or, as one of the first users said:

“It’s $99 and cancelable after 30 days, it’s pretty risk-free. I pay more for an Uber to the airport.”

Claim founding rate - $99/mo

A little context first

Lenny Rachitsky shared a report earlier this week that showed burnout is a much broader trend across the entire tech workforce than we may have realized as burnout jumped from 44.7% to 55.7% while career optimism dropped from 54.8% to 48.7% since he ran the same survey last year.

The timing of this report came at a good time for me as it was right when I was in the middle of trying to sort out the chronic fatigue I was feeling + why my HRV/health metrics were declining despite putting more effort into improving them.

It was the “aha” moment when I recognized that I needed to approach this from both a physical and mental standpoint.

So like most of us today, I went over to Claude + started a conversation on this topic to help me work through things. And it didn’t pull any punches after dropping in all of the context in order to start synthesizing what it meant for me:

THE SYNTHESIS

The story is coherent and it’s almost entirely explained by one variable: chronic psychological stress.

HRV is the canary. It’s been declining since January — which tracks with when the burnout started intensifying based on what you’ve shared. The body is showing the cost of operating at high cognitive load in a depleting environment, even while you’re doing everything right on sleep, training frequency, and alcohol. The sleep data is holding because you’ve been disciplined about protecting it. But discipline has a cost too — you’re white-knuckling good habits in a difficult season, and that effort shows up in the HRV.

The question that almost led me down the wrong path

After reading the above, I did what anyone would do + asked a simple question back: “What can I do to help turn this around? I need behaviors + habits I can start implementing to improve this.”

And this is where Claude nearly led me wrong + why I will always be a proponent of never taking things at face value + choosing to think for yourself:

Highest leverage
The incline walk protocol you’ve already committed to is the single best thing on the list — but the mechanism matters. It only drives HRV improvement if you’re genuinely in Zone 2 for sustained periods. This is the physical intervention with the most direct parasympathetic upside.

Medium-high leverage
One genuinely low-effort addition: 5 minutes of slow, controlled breathing once per day — 5 second inhale, 5 second exhale — not as a meditation practice but as a physiological intervention. Resonance frequency breathing at that cadence has the most direct evidence base for HRV improvement of anything non-exercise related.

The one thing I’d push back on adding
More intensity in training right now. Your Zone 4 time doubled this period. That’s good for VO2 max long term but it’s additional sympathetic load on a system that’s already running hot. Don’t add more hard training sessions until HRV stabilizes. The incline walks are the right tool for this season specifically.

Being someone who always comes at things from a root-cause perspective, I recognized that while the incline walk + breathing exercises Claude recommended would technically help improve my HRV, that those were bandaids to the larger problem. They wouldn’t counter my sympathetic nervous system running in overdrive.

That’s the problem I needed to solve, not come up with a workaround to improve the HRV metric for the sake of improving it (sounds a bit like some other conversations we’ve had on here re: Goodhart’s Law, doesn’t it 😉).

So I pushed back. Said the incline walk would get zone 2 time up, but not counter the sympathetic overload. And then from personal reflection, I said I disagreed with the recommendation to avoid more intensity in training - that training intensity is my stress outlet and that walking/breathing exercises don’t quite get stress out the same way a hard run or heavy lifting session do.

And this is where the conversation really got interesting + the unlocks hit me hard:

1. The incline walk is a cardio tool, not a nervous system tool. Claude conflated these 2 which was a huge error. With my sympathetic system running hot from psychological load, the solve for this is parasympathetic activation, not aerobic base building.

2. A hard run/heavy lift, while highly stressing on my body, isn’t actually adding sympathetic load - it’s how I discharge it. It’s a fundamentally different physiological effect from chronic stress.

Jumping off of #2, I looked at my WHOOP data to see what it said when running an analysis through this lens. The finding was eye-opening to say the least:

High intensity workouts produce better next-day recovery than low intensity or rest

This is the most counterintuitive finding and directly validates your instinct about running. The day after a high intensity session your HRV averages 59 and recovery hits 72% — meaningfully better than low intensity (56 HRV, 66% recovery) or pure rest days (54 HRV, 66% recovery). Your nervous system responds well to hard output. It's discharging, not accumulating. This is a fast-twitch athlete pattern and it means you should protect the intensity in your training, not moderate it.

Fascinating.

My geek mode officially entered full force after this + I went down the rabbithole. To better understand this counterintuitive insight, I needed to better understand my personal dynamic between stress, workout intensity, stress discharge, and recovery.

TLDR on a hard workout comes down to what’s called “catecholamine discharge.” Long + short of it is chronic psychological stress means your body is continuously producing fight or flight hormones and never have the opportunity to clear out. A hard workout forces an acute catecholamine spike, which then crashes. This sounds scary/bad to hear your body is dumping the stress hormones hard and fast, but it’s actually working in my favor as my parasympathetic system swings hard in the other direction to bring me back to baseline.

AKA the bigger the discharge, the bigger the rebound.

Low intensity workouts + rest days never discharge that stress build up. The chronic load just…sits there.

Slow-twitch vs fast-twitch

Fun fact: during my freshman year tryouts for the high school soccer team, I had the second worst time in the mile run. Not a great way to be viewed by your coach when trying to make the team.

But then we hopped on the field to scrimmage + my energy seemed endless. Making runs, getting into the right positions on the field as needed, etc. Endurance didn’t seem to be an issue like it had been on the track earlier in the day.

Finally, we wrapped with full field sprints. And here the inverse of the mile run happened - I was first or second to hit the endline each time.

It was years later that I’d learn there was a physiological definition of this: I fall HARD to the right toward the type-II (aka fast-twitch) muscle fiber scale compared to the type-I (aka slow-twitch) side.

Those who skew toward slow-twitch do well in heavy endurance activities (think: marathons, cycling, etc.). Those who skew toward fast-twitch do well in “explosive” activities (think: sprinting, powerlifting, etc.). There’s no good or bad when it comes to one or the other, it’s just a matter of knowing what you’re more predisposed to.

The reason I share that is because that was the key to solving + breaking my stress cycle.

First, it means my sympathetic system is wired to fire hard + recover fast. It’s designed to handle spikes, not sustained low-level activation. High intensity training plays right into this benefit.

Second, it means my parasympathetic rebound after high-intensity training is stronger than it would be in a slow-twitch individual. When I flush stress heavily through high-intensity work, I recover fully by clearing it from my system.

Pretty cool, right?

Most advice is geared toward the average

This single insight should probably have me cancelling my WHOOP membership.

When I let stress build + don’t get a hard workout in, my HRV data illustrates that by rapidly declining/being below my “normal” rate. WHOOP translates this as a “red” day and basically says “hey, you should probably take it easy today.”

But in knowing my psychological + physiological profile, as well as listening to my body to understand if I’m truly feeling “red” (AKA sore muscles, feeling sick, etc.), usually that HRV drop is from the catecholamine build up + needing to be cleared out.

So I disregard those “red” days + push myself. And my body (and mind) thank me. And my WHOOP data even shows this benefits me:

On red recovery days (recovery score ≤ 33%), my workout strain averages 16 (compared to yellow days of 12 or green days of 13). And my next-day recovery score is usually a significant improvement.

On Thursday this past week I decided to be a masochist + go for a hard run when it was 93ºF out. Absolutely brutal run + I was gassed when I finished. Normally this would show up the next day as a dropoff in HRV as a body recovers. Mine shot up 🤷‍♂️

This is a flat out inversion of WHOOP’s algorithm that’s built on population averages where red = rest. My autonomic nervous system doesn’t follow that model. I share this not to say look at how unique of a special snowflake I am, but to show why it’s so important to understand + figure out what works for YOU.

Obviously, I watch for genuine sickness + injury signals via elevated skin temp, elevated resting respiratory rate, general “how am I feeling” check + treat those days differently.

Why I’m sharing this

1. If you’re feeling even more stressed or burned out this year than before, you aren’t alone.

2. It’s easier than ever to understand your unique makeup thanks to access to health metrics (think: wearables like WHOOP + Oura, bloodwork testing via your doctor or Function Health) + AI tools that can analyze and then synthesize the huge amounts of data contained in those.

3. To share the (very imperfect) prompts I’ve used to help me get to these insights in case you want to work through any of this for yourself:

   1. “I want you to help optimize my health. First we'll baseline my general health via uploaded data from my WHOOP (csv files) as well as recent blood test results + supporting clinician notes from them. First thing - give me a breakdown of what you're seeing + be brutally honest. I want to hear what's really good, what's good, what's ok, what's bad, and what's terrible.”

      1. Note: after you go through this + get outputs from your LLM of choice, I simply did some back + forth chatting to better understand why things were/weren’t good, etc.

   2. After an appropriate amount of time has passed + you’ve taken action on insights, come back to see what has/hasn’t changed.
      “I’m currently exporting out my most recent whoop data + want to see how that’s looking compared to the prior period when you last reviewed it all.

      I want you to clearly pull out anything that’s different from that prior period (good AND bad) across all major + minor metrics. Then we can look at the behaviors + variables that we think are playing into those (can pull from the journal entries + I want you to ask me questions that wouldn’t show up in the journal but that we know influence things).

      Before I upload this, I want to see your plan of approaching this, the data you’re going to show/compare, etc.”

      1. Note: push back on responses. Like WHOOP, LLMs are based on the average of data + insights, so make sure you guide it with your unique makeup, quirks, etc. to account for those.

From there, the sky’s the limit. Since I love tracking data + trends to hold myself accountable, I had it help me get it into a visual that I can use + build off of as time goes on. Then for things like bloodwork deficiencies, I asked for different whole foods + supplements that I could incorporate into my diet to improve those.

Simple. Easy. Geeky. Call it what you want, but it’s been fun to learn more about myself AND know that by taking action on these things I’ve been able to already start to feel physically + mentally better. Win-win all around.

A few examples of the visuals:

See you next Saturday,
Sam

Today is a special edition as it’s the first official “guest post” on here + it’s one I’m incredibly proud of as it’s coming from Elie Daccache, a member of my team at Loxo. Funny enough, it was through this very newsletter a couple of years ago that Elie + I started emailing back and forth each week, him sharing his thoughts about the newsletter with me + helping to sharpen the things I was learning.

Elie has one of the most insatiable growth mindsets I’ve ever encountered, so when he asked me a few weeks ago if I’d be open to having him collab on a newsletter here, the answer was an immediate yes. What follows is something he’s recently learned from a mentor of his when it comes to finding new growth levers, even when you think you’ve tapped out what’s at your disposal.

So without further ado, I’ll let Elie take it from here…

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My mentor, the general manager of a $300m fast-moving consumer goods division at Fattal, one of the largest distributors in the Levant, spent a week sitting in the living rooms of strangers, watching women clean their houses. He didn’t need to. He had analysts, panel data and a market-research budget most chief marketing officers would envy. He chose instead to spend a week on the sofas of married, stay-at-home women across several regions of Lebanon, notebook in hand, watching them wipe floors and scrub sinks. By the end of the week he had the insight that would grow one of his brands sevenfold in two years, and it came from noticing something no dataset had thought to record: the woman in front of him already owned a product that could clean her entire house, and had bought half a dozen others to do jobs it already did.

That one observation contains the whole argument, so it’s worth seeing how he got there.

The problem nobody prepares you for

Most of us spend our careers trying to win a market. My mentor inherited the opposite problem. The portfolio handed to him was made up of brands that had already won, several sitting at around 88% market share and one higher still. At that altitude the familiar playbook stops working, because there’s little meaningful share left to take from competitors who have almost none, and no obvious way to enlarge a number that’s already pressed against its ceiling. So he faced two difficulties at once: preserving the extraordinary share he’d inherited, and still growing sales in markets everyone around him considered saturated.

If you run B2B software marketing, you know this one in your bones, even if the products couldn’t be more different. It’s the plateau. The obvious ideal-customer profile has been worked through, pipeline flattens, and sooner or later someone says the market’s been saturated and the room accepts it as a fact of nature.

That conclusion is almost always premature, and the reason is the framework my mentor built to escape it, which he called the 3 Us. His premise was that market share isn’t a single number but the product of three separate levers, and that a business convinced it has run out of room has usually exhausted one of them while leaving the other two untouched. The first is Users, meaning how many people use the product. The second is Usage, meaning how often they use it. The third is Uses, meaning how many different jobs they use it for. Each brand in his portfolio happened to be stuck on a different lever, which makes them an unusually clean way to watch all three at work, and each one translates with surprising directness into a growth motion you can run in software.

How he grew Dettol’s sales 7x in 2 years

Back to the living room. In the Middle East at the time, Dettol carried a reputation problem disguised as a strength. Everyone knew the brand, and everyone knew it for exactly one thing: it was the disinfectant you used to clean a bathroom. It also sold at roughly four times the price of the nearest detergent competitor, which made it premium, respected and thoroughly boxed in. A product understood to have a single job can only be bought for that job, and its ceiling gets set accordingly.

Rather than commission a repositioning campaign from behind his desk, my mentor borrowed the method of “Blue Ocean Strategy” and went looking for the uncontested space himself. He set up an observational study of the core audience, the married women who ran these households, and embedded with them for a week to watch how the cleaning actually happened.

And what he saw resolved the whole problem. The women used Dettol for the bathroom, and only for the bathroom, exactly as its reputation dictated. For every other surface in the house, the floors, the sinks, the fixtures and the wood, they reached for a different bottle, and had accumulated half a dozen of them under the counter. Yet the contents of those bottles were, chemically, almost identical to the Dettol already sitting in the cupboard. What separated one product from the next wasn’t the formula but the degree of dilution. The customer was buying five extra products to do jobs the one she already owned could handle, had anyone bothered to tell her the right dilution for each.

That’s the lever he called Uses, and it relocates where growth actually comes from. The additional sales weren’t waiting in a new customer or a new product but in the unused capacity of the product already on the shelf. Two questions fall out of it, and both are worth keeping. How many more ways can the same customer use the product? And what different customer might use the very same product for an entirely different job?

So Dettol got un-boxed. From the bathroom disinfectant it became a multi-surface, multi-room product suitable for floors, walls and fixtures, and even for the kind of hygiene prep appropriate to an operating room. The molecule didn’t change; the number of jobs it was sold for did. Sales grew sevenfold within two years. Der General, another brand in the portfolio run on the same logic, tripled.

Uses have a metabolism

Then he did something most brand marketers wouldn’t have bothered with, and it’s the part that turns a tidy anecdote into a forecasting method. A new use doesn’t merely add a reason to buy; it adds a rate of consumption. During the same study his team logged how often the women cleaned each part of the house, broken down by region and by age group, and how much product each job consumed. A bathroom cleaned twice a week at three bottle-caps a time accounted for six caps weekly; floors cleaned three times a week at a single cap each accounted for three more. Sum that across every use a given segment had adopted, and you could see how quickly a household would empty a bottle and therefore when it would need to buy the next one. Purchasing frequency, segment by segment, derived from what people actually did rather than guessed from a trend line.

This is the muscle B2B technology is about to need. Software has long been forecast on the basis of seats, which are convenient because a seat is a headcount that renews on a predictable annual cycle. The industry is now moving fast toward usage and consumption-based pricing, and AI products in particular tend not to bill by the seat at all but by the token, the run, the workflow or the outcome. In that world per-seat forecasting doesn’t merely lose accuracy; it stops describing the business. What replaces it is exactly what he built with a notebook on a stranger’s sofa: a bottom-up model of consumption that asks how many distinct jobs a segment runs the product for, how heavy each job is, and how often it recurs. Answer those questions and you get more than a cleaner lifetime value. You get timing, an estimate of when a given account will hit its next genuine need, which is the single most useful input a retargeting or expansion campaign can have, because it lets you show up the moment the bottle runs dry instead of broadcasting to the whole list at once. In a consumption-priced market that bottom-up plan, built from the 3 Us and plain old qualitative research, becomes the forecast itself rather than a supplement to it.

There’s a more immediate reason the Uses lever matters to a marketer, which is that every new use is a fresh universe of demand. While Dettol stayed the bathroom disinfectant it competed for a single cluster of intent, one set of keywords and queries and one position on the shelf. The moment it became a floor cleaner, a wood-surface cleaner and an operating-room prep, each of those uses brought its own keywords, its own search volume, its own audiences, its own ad sets and its own content. A new use adds a whole addressable surface to go compete for. So when paid search plateaus and the keyword list feels tapped out, the more productive question usually isn’t how to bid harder on the terms you already have but which use of the product you’ve never actually advertised.

Because each unadvertised use is untapped volume sitting in plain sight.

The Durex problem: nowhere to go but usage

Durex presented the opposite constraint. It held 88% of its market, which left essentially no room on the Users lever, since a number that high can’t absorb many new customers. Nor could the brand plausibly invent a portfolio of new Uses, there being only so many jobs a condom can be sold for. Unless you’re a little creative, of course.

Two of the three levers were, for all practical purposes, pinned in place, which left Usage: getting existing users to use the product more often.

The complication was that he was working in a devout Lebanese market where sex is taboo, hardly a subject a brand can address with a straightforward instruction to buy more. So growth took the form of education and awareness aimed largely at younger people, normalising the conversation and funding the kind of advertising that raises the frequency of the behaviour the product depends on, without ever being able to fall back on the blunt commercial message a less sensitive category would use.

The parallel in software is the lever most teams under-invest in, because raising usage is less glamorous than winning new logos. When the Users count is saturated and no new Uses are available, growth has to come from frequency: activation, feature adoption, the formation of habits and the depth of the relationship with the accounts already signed. Under consumption pricing this isn’t a soft metric but the revenue itself, since more usage of the same use by the same users flows straight into the bill. Durex could add neither users nor uses and so competed entirely on frequency; plenty of software companies could grow substantially without signing a single new customer if they did the same.

The OMO problem, solved in a supermarket aisle

The third lever produced the story where the general manager left the building most literally. In late 2019 Lebanon suffered the sharpest economic collapse in its history. The currency fell apart and government-subsidised consumer goods flooded the shelves, which for a portfolio of premium brands was close to an extinction event, as subsidies and acute price sensitivity commoditised the category and set off a race to the bottom. Among his brands the weakest position belonged to OMO, a laundry detergent owned by Unilever, hovering at around 2% market share.

The move available from the desk was to cut price, protect margin and concede the year. My mentor drove to the supermarkets instead. The general manager of a $300m division went from shop to shop across the country to see for himself what was happening at the shelf, and in every location he found the same scene: crowds gathered around the subsidised goods, each of which wore a bright red-and-yellow sticker reading مَدْعُوم, Arabic for “subsidised”. Shoppers weren’t comparing brands or reading labels; they were navigating by the sticker, which had become the most valuable piece of shelf real estate in the country. He would have never realized this had he not stood right in the aisle.

There was the play. He talked the executive team and the board into giving him a budget to subsidise OMO with Fattal’s own money, undercutting the government’s price and putting the brand in the same discount conversation, and then printed the very same red-and-yellow sticker the subsidised goods carried, adding beneath it the words “subsidised by Fattal”. He borrowed the visual cue shoppers had already been trained to trust and pointed it at his own struggling brand. The forecast tells you how little anyone expected of OMO: even assuming the experiment worked, the plan was to sell ten shipping containers of product across the entire year. They sold out in a week, roughly fifty-two times the annual forecast in seven days.

Several lessons sit inside that result, each with a direct analogue in technology. The first is to go down to the market yourself no matter how senior you are, because a $300m general manager standing in an aisle saw what no report would have surfaced; a report averages away the very detail that mattered, and the most reliable market research is still the kind you do with your own eyes at the moment of purchase. The second is that shelf space is itself a touchpoint rather than neutral inventory, working at once as an advertisement, a trust signal and a decision-making environment. Its digital equivalent is everything surrounding the moment a prospect decides: bottom-funnel search, whether an AI assistant recommends the product, on-page experience and navigation, all the surfaces a buyer touches while actively weighing a purchase, and most software teams leave them to chance while obsessing over the top of the funnel. The third is that shelf share correlates with market share, since the more effortlessly available a product is at the point of decision, the more it sells, which for software means earning presence on the surfaces that genuinely matter to your buyer rather than the ones a category report happens to list, or intuition assumes, or best practice recommends. The last is to borrow from markets that look nothing like your own: his edge came from lifting a government’s subsidy sticker and re-aiming it at a detergent, and the most defensible promotional ideas tend to come from outside your own category, in a mechanism that works somewhere else and can be adapted before anyone nearby thinks to.

Why the 3 Us resist automation

Seen together, the three stories share a quality that matters now in particular. None of the insights existed in a dataset. The Dettol breakthrough came from a week spent watching dilution habits on a sofa; the OMO play came from noticing which sticker a crowd gravitated toward; the Durex motion came from understanding a specific cultural taboo well enough to work around it. Each one needed primary observation and a creative leap, the act of going somewhere, watching something, and connecting two things that weren’t obviously related.

That’s the work a language model can’t do on your behalf. A model will happily generate a hundred variations of the keywords you already have, but it can’t spend a week in a stranger’s living room and come back understanding that the customer is buying five products to do one product’s job. The raw material for a new U is gathered in the field and assembled with imagination, which is the part that stays scarce precisely as everything downstream of it gets cheap to automate. The framework is defensible against AI because its inputs are.

For the same reason the 3 Us work as a brainstorming engine for marketing, not just for product development. When growth stalls, you can run the portfolio against three questions: which segments of Users have we never gone after, which Uses of the product have we never advertised, and how could we get existing users to higher Usage. Most teams, hitting a plateau, reach only for the first of these, chase more users, and conclude the market is tapped out when that lever gets stiff. My mentor’s career is a sustained argument that the ceiling you run into is rarely the market’s, and far more often the two levers you forgot you were holding. Nothing in the data said a premium brand known for a single job, in a market widely judged mature, had a sevenfold gain sitting inside it. It had been there the whole time, in the gap between what the customer bought the product for and what the product could actually do.

See you next Saturday,
Sam

I was sitting at my desk, staring at the screen of my laptop, waiting for a moment of insight to hit me. Waiting to uncover what would help me get our marketing out of a plateau we’d been in for a few months.

A minute passed.
5 more minutes passed.
Another 20 minutes passed.

And there I sat, no closer to getting unstuck + no flashes of brilliance anywhere in sight.

So I grabbed the pup, put his leash on, and we went for a walk.

Left the headphones at home, no podcast or music playing, just a good old fashioned walk to let my mind “air out” a bit.

A half hour later, we’re back home + I had 8 different notes saved in my phone containing ideas + insights to dig into to help break out of the plateau.

And that’s what leads to today’s newsletter. A quick reminder that going for a walk remains undefeated whenever we get stuck, and a list of ideas + plays you can steal the next time you find your funnel’s hit a plateau at a certain stage.

Here are the plays I've run/tested over the years to break through each stage of our funnel.

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Constraint #1: website visits > handraiser rate

You’re getting people to your website, but want to increase the rate at which they take action.

Play 1.1: Add more conversion points across the website

Don’t let the simplicity/obviousness of this one fool you. I’ve overindexed before on the sticky nav to do the heavy lifting of converting web visitors, assuming they’d know to go there when they were ready to take action.

Make the experience as easy as possible for your visitors. CTAs in the nav, hero, sprinkled throughout the scroll experience of the page content, + the footer are near-requirements. Then feel free to experiment with things like in-app chat popups, exit-intent banners, etc. if you really want to go nuts.

Play 1.2: Social proof

“Is this product/service built specifically for people like me, struggling with the type of problem we’re currently experiencing?”

This is the question every web visitor is asking themselves when they hit the website. And it’s SO important that this is answered as quickly as possible.

The problem is most visitors are skeptical of marketing claims like “#1 [category] software” since everyone says that. The best way to counter this is to get specific AND do so using data from the customers you have that are exactly like those visiting the site.

Logos are great for recognition + telling a visitor that companies like them use your product. But the real power comes when you can grab quotes + real results from them that answer the second question the prospect has - that they solved the problem and are now thriving.

Play 1.3: CRO experiments

The best way to break through this constraint is to simply get experiments in play + adopt a mentality of continuous iteration on them.

Every persona + market operates differently, so blanket best practices for how pages should be laid out, the type of content that should be surfaced, etc. is a watered-down average. The best websites operate using what they’ve learned from their market + buyers specifically.

Whether it’s as simple as button colors or as specific as the medium + style in which content is being presented, there’s always room for growth when it comes to this play.

Play 1.4: Interactive demo

Letting visitors experience your product before committing to a meeting removes the biggest objection they have (”I don’t know if this is worth my time”).

Visitors who complete a product tour on the website convert to handraisers at a significantly higher rate than non-product tour viewers. Bonus is that they also typically convert from handraiser to SQO at a higher rate as they go into the call with your sales team already understanding what it is that the product does.

Play 1.5: Objection handling content

“There’s no way our finance team will approve this purchase.”
”I don’t have access to the data this tool needs in order to work.”

The list of objections goes on and on. Most companies rely on the prospect getting into the conversation with sales so they can answer these questions.

The problem with that is there’s a good chunk of people who never fill out the form because they believe they already know the answer to it + that the call won’t be worth it. That’s why proactively presenting this type of content is a wildly underused tactic on the website + one I’m increasingly bullish on moving forward.

Constraint #2: not enough handraisers

Play 2.1: Use case videos

Similar to the interactive demo on the website, proactively getting use case videos out to the market is the epitome of “show, don’t tell.”

When your prospects see how easy it is to solve their problem vs. being told (and as a result, skeptical of) by a sales rep that the product/service will solve their problem is a night + day difference.

Play 2.2: Paid ads

This one’s pretty self-explanatory 🤷‍♂️

If you aren’t running anything, pushing ads out to your ICP will give you a boost. If you are running ads, making sure you’re hitting the right people (strong targeting) + are using compelling content (videos, thought leader ads, etc.) are the two buckets with the most opportunity to optimize.

Play 2.3: Give value to get value

“Register for a demo + we’ll send you a $100 Amazon gift card!”

Great way to get demo requests, terrible way to get SQOs. Most come for the gift card + very few go on to be SQOs.

The idea here is strong in that it pulls people into your funnel who may not quite be compelled enough to take action, but the execution/”carrot” being used is wrong.

Best thing to do is give the prospect value that only you uniquely can give them AND that it’s a function of the product/service you’re marketing.

Here’s an example of one I’m running right now:

• ICP is clearly called out in the creative

• Desired/impressive result is clearly called out in the creative

• The answer to how this is possible is called out in the creative

• The post copy contains more examples of desired outcomes

• The post copy CTA is value-led to the prospect that’s a no brainer - they get help on a role they’re struggling with and can see how the software works in practice (not theory)

Play 2.4: Update stale content on site

Google + LLMs are putting increased weight on the recency of content to determine what they serve up to searchers.

Most websites have countless pieces of content floating around. Go back + refresh/update the heavy hitters. Toss in new data, provide new context, etc. and make sure the page has something like “published on” or “last updated on” so that it can be indexed and considered appropriately.

Play 2.5: Referral program

People love to tell others about things they love. You probably already have a fair bit of growth due to word of mouth whether you know it or not, but the key here is putting a proper incentive behind it.

The best referral programs operate under a “you win AND they win” incentive. Think: they get a month free + you get a month free.

Constraint #3: handraiser > SQO rate

Play 3.1: remove demo scheduling friction

Another obvious one that most of you here have probably implemented over the past few years, but sharing because this should be a non-negotiable now.

Allow prospects to schedule the date + time of their demo as soon as they fill out the form. Reducing friction between the request + getting them to the discovery call converts more demos into qualified opportunities.

Play 3.2: ICP/targeting refinement

It’s nice to have a broader pool to target with ads, emails, calls, etc. But have you ever noticed how certain segments/personas seem to do better/worse at turning into SQOs? I bet you have.

Take that data + layer it into your prospecting efforts. If we know you can get a bunch of demos from a certain industry, but they rarely convert into SQOs, then we’re just on the lead gen hamster wheel + pretending we’re hitting our goals since demos are technically coming through. Tighten up industries, job titles, etc. and watch this rate increase.

Play 3.3: channel audit

Similar to the above, there are channels where we know we can get a higher volume of leads from them, but they usually convert at much lower levels than others (looking at you Facebook…).

If you aren’t to the point of diminishing returns on a channel that does convert well to SQO, this is where I typically pull back budget from the “higher” demo volume, but lower SQO volume (function of that conversion rate) + allocate that over to the channel that does convert better.

Play 3.4: lead qualification process

BANT. MEDDIC. CHAMP. SPIN. NEAT.

The list of sales qualification methodologies goes on and on. The main thing is to simply pick one that works for your organization + standardize it across the team.

A tighter qualification framework reduces inconsistency in how reps assess the fit of leads coming through + that typically results in improving this conversion rate as you iterate over time on what you find does/doesn’t convert well.

Constraint #4: SQO > win rate

Play 4.1: gifting/direct mail

This one needs to be used with common sense, but let the psychological principle of reciprocity work in your favor.

The best plays to use in this 4th constraint bucket all revolve around 1:1, relationship-based dynamics. Take the time to research the people you’re engaging with in the deal + send them something that pairs in with that finding.

The value isn’t as important as the signal this gives the prospect of you taking the time to show you value them at a 1:1 level + that this is a representation of what working with your company over the long-term will be like.

Play 4.2: executive sponsor

I don’t have hard data on this, but I can tell you that any time I’ve had the CEO or other leader of a company jump into the conversation when I’m evaluating software/services, I buy from that vendor far more than I don’t.

There’s a certain weight that the attention of executives carries with the market + the more you can leverage that inside deals, the better the outcomes typically are.

Play 4.3: get face time

Whether it’s a simple drop-in to a prospect’s office to bring them cookies from a local bakery or a more formal onsite presentation for the team you’re selling to, face time goes a longggg way in closing deals.

Better yet, get prospects outside of the office. Take them to dinner. Have them meet you for an “experience” type event. TBH anything that gets them outside of the “buttoned up” persona they feel they need to carry in the office + into an environment where they can be more like themselves.

Bonus tip: don’t limit this to executives/”buyer” personas only. Get the internal champions + power users involved here. These individuals are more impactful to your deal closing than any other factor once you hit SQO stage.

Putting this into action

If you know where in the funnel you’re constrained, get some experiments in play. Steal some from the above, or spin up an account in Affect where there are 50+ different, proven plays you can run to break through the plateau. Perk of that platform is that not only do you get access to all of the plays, but when you commit to a play, it logs the current conversion rate/volume so you can see its impact after the experiment period.

AKA no more wondering “what’s working” - you can see it with your own data.

Founding member rate is still available - 45 left at $99/mo, locked in for life. Or, as one of the first users said:

"It's $99 and cancelable after 30 days, it's pretty risk-free. I pay more for an Uber to the airport."

Claim founding rate - $99/mo

See you next Saturday,
Sam

P.S. next weekend is the 4th of July here in the US, so no newsletter as I’ll be spending time with the fam. See you on the 11th :)

noun
sy·​co·​phant

A sycophant is a servile, self-seeking flatterer who acts insincerely towards those in power in order to gain a personal advantage. Often called "yes-men," "toadies," or "brown-nosers," sycophants prioritize pleasing superiors—agreeing with everything they say and showering them with unearned praise—rather than offering honest feedback.

I’ve been thinking a lot about this word lately. More specifically, the last bit of the definition above stating “…sycophants prioritize pleasing superiors—agreeing with everything they say and showering them with unearned praise—rather than offering honest feedback.”

Now think about your most recent conversation with Claude/ChatGPT/etc. How’s that conversation look when viewing through the lens of this word? If they’re anything like mine, they probably look like a sycophant at work. That everything you say is great + everything you propose is brilliant.

But this isn’t a good thing, and here’s why…

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Affect is for the marketers who have sat in a room where marketing celebrated surpassing its MQL targets while the business missed revenue. It’s for the marketers who want to be held accountable because they’re confident enough in their work to let the math speak for itself. It’s for the marketers who understand that clarity is earned, conviction is a choice, + being a force on the business is the only version of this job worth doing.

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No one likes a “yes man”

Every organization has had these for centuries. The individuals who, as soon as they’re in a room with company leadership or a high-value client, only seem to be overly agreeable to anything presented + quick to compliment them.

They want to be seen as likeable + to be trusted by the leader, so what quicker way to do that than to be overly positive toward them, right?

Nope.

Go ask any leader what they really want + their answer will be someone who tells them the truth. Someone who tells things as they are based on the reality they’re in. They’re surrounded by sycophants already, so the individual who is willing to disagree, who is willing to share truths, no matter how uncomfortable, is actually respected more by the leader.

These are the people who create balanced organizations, who help keep the company from making mistakes because no one’s willing to speak up, to say, “You know, I see where you’re coming from, but I don’t think we’re accounting for XYZ here…”

These are the individuals who end up with a seat at “the” table, while the sycophants are all fighting over their middle-management titles + swinging their weight over their teams.

The rise of the s(AI)cophant

Now as more individuals begin to adopt AI + LLMs for their work, these tools become their sparring partner for various ideas, experiments, strategies, feedback sessions, and more.

It’s a great way to role play out scenarios + gut check theories with data that AI can sift through near instantly. BUT, there’s an inherent flaw in most LLMs as of when I’m writing this in June 2026 - that the LLMs are trained sycophants.

Everything you propose is a great idea.
Every response you push back on is met with “you’re right, [your response] is much better.”
Every output is wired to what it thinks will be best received by you, not by what’s factually correct or what’s unbiasedly best.

The end result of this is that you feel great about your work, but when executed upon is rarely what should actually be done when viewed from a logical perspective.

You’re married to a tagline you love, so the LLM weaves it into all of your marketing materials…
…meanwhile, that tagline is a bunch of business jargon that makes zero sense and carries no weight with your audience.

You want to push into a new market because one new deal came through there, so the LLM builds an entire campaign strategy to push into it…
…meanwhile, no validation has been done that the new market is worth it and the current market that has product/market fit is FAR from being close to saturated.

If we don’t have the awareness to think critically about what’s being presented, or have someone willing to push back on these proposals, there’s serious risk of going down the wrong path, fast.

So my ask of everyone reading this: don’t drink the koolaid. (koolAId? sorry, couldn’t help myself at the irony there…)

While it feels great to be told everything we think/do is genius + that there’s always some gold-paved path ahead of us + all we have to do is ask Claude/ChatGPT to lay it out for us, we need to keep a healthy level of skepticism when reviewing these outputs.

Perhaps there’s a lesson from history we can apply in a new context here.

In Roman times, upon returning from battle victorious, it is said that there would often be a servant standing in the chariot behind the general whispering memento mori, which in this context translates to, “remember that you are mortal.”

Yes, this parallel is a bit of a stretch for those of us who are clacking away on our keyboards each day, but always keeping in the back of our minds that not all of our ideas really are “the best” ideas ever, that not all of our plans are perfectly thought through on the first go + need no alterations or input from others.

So maybe it’s better to remember another famous proverb from millenia back as a counter to sycophancy, whether it be in human or AI form - “as iron sharpens iron, so one person sharpens another.”

The best ideas + the best plans often come from iteration and healthy disagreement. It would be a shame for us to lose that as more + more work is delegated to AI to handle.

See you next Saturday,
Sam

AEs sending their 7th email in a 2 week span:
“Hi Sam - Me again 🙃 Apologies for the professional persistence. Here’s a link to my calendar to grab time for us to talk.”

Marketers on email working “well” for them + want to juice it for more:
”Let’s send emails out to our market daily instead of weekly!”

BDRs on cold-calling:
“I double tap (call back to back if no answer) prospects regularly”

Meanwhile, how prospects/customers feel on the receiving side of these tactics:

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Here’s the deal

For too long, B2B companies have operated under the impression that touches are either impactful or not impactful, or more simply put, they’re either “positive” or “neutral.” Since these touches are viewed from a “new customer acquisition” lens, it’s viewed as a binary yes or no response to “Did [touchpoint] lead to better business results?” and not “Did [touchpoint] result in the prospect thinking more positively or negatively of us?”

But a CRM will never show negative pipeline created, and that’s precisely why this has been so often overlooked.

Until now.

Put yourself in their shoes

Take a step back from your marketing/sales/etc. role and be your prospect for a minute.

• You’ve just received 2 calls back to back from a number you don’t recognize after intentionally screening the first call

• A few minutes later, you receive an email that starts with “Me again 🙂 I apologize for my professional persistence, but you could really benefit from [our product/service]. Here’s a link to my calendar to grab time for a demo.”

• A handful of hours later, you receive a generic email from their marketing drip sequence inviting you to a webinar…but the persona/segment is the wrong one

All of this in just one day.

And while the above is a fictitious scenario, I can attest firsthand to having the above experience happen to me multiple times over the years (or just last week as you can see from the screenshot below…) as various companies tried to get me to buy from them.

What would you do if you were in your prospects’ shoes? Remember:

• You aren’t looking to buy anything right now (+ you certainly don’t want to deal with the internal change management as everyone’s working hard enough to keep up with the new AI mandate in their company…)

• You’ve never been to this company’s website, so you aren’t even sure what they really do

• You didn’t ask for them to reach out to you

• You’re already strapped for time trying to do the things you need to complete in your day-to-day

• You flat out don’t trust them or know how credible they are

So how would you respond in this scenario? Would you ignore them? Would you cave and take the call? Would you get furious after receiving the 9th call + email from them?

This last group is one that isn’t accounted for.

Most companies today play the volume game…

Execs after learning about the predictable revenue model:

“If our SDRs make 100 calls/emails per day, we know we’ll get 10 meetings booked and 1 opportunity, so let’s get them on the phone cranking even more out!”

The problem with this math is that while you may get 10 meetings booked and 1 opportunity, you’re not taking into account what happens with the other 90 calls/emails that have been hitting your market over the head 10+ times in the past week.

Of those 90 prospects, here’s what’s likely going to happen:

• 55 are simply going to ignore you

• 20 will finally reply and say they’re not interested

• 10 hit the unsubscribe

• 5 are completely turned off + you’ve burned the bridge for them to ever become a customer (not to mention the negative word of mouth they’ll spread when peers ask for their opinion…)

Let that sink in for a moment.

Of the 100 emails/calls you’re making, you’re making a trade-off.

10 meetings booked for 5 burned bridges.
1 opportunity today for 5 opportunities that will never come about in the future.

This is the epitome of having a short-term focus only + not thinking about how to grow your company in a sustainable way.

Trading 1 opportunity NOW for 5 opportunities that will NEVER be. But the problem with these 5 burned bridges is that the company simply sees these attempted outreaches as “did not connect” or “unengaged.”

They don’t think about how these messages are perceived by the receiver. They have no way of logging in their CRM that this account is “burned.”

So your CRM spits out campaign results of “10% success in booking meetings, 1% SQO rate,” leading you to believe the other 90% is still fully intact.

The reality of it is that the campaign results look more like “10% success in booking meetings, 1% SQO rate, 5% removed from all potential future opportunities.”

…but leading companies today play the quality game

The best BDRs I know don’t make 100 dials per day, they make 15 and do their due diligence before reaching out to the prospect. The result is much higher conversion rates with those targeted accounts over the next 1-2 quarters.

The best emails I receive from companies are weekly or monthly sends that add value to ME in my role. Instead of wondering how they can increase their open rates from 7% to 9%, they have open rates of over 40% + an audience that looks forward to receiving these.

The best ad campaigns have multiple ad variations + are constantly being iterated upon on a regular basis to stay fresh + relevant. The message and content behind them are timely + relevant to the audience who sees them.

Buyers have the power now

Use common sense with your prospecting + outreach campaigns.

Are you truly creating a relationship with your prospect?
Are you adding value to them before making any type of ask?
Did you even check to make sure your “personalized” template has the right name?

And my personal favorite question that I ask myself before we take anything to the market:

Would you respond to you?

One podcast episode I enjoyed this week

Been a minute since I’ve shared a podcast rec on here. But after hearing this one on a walk this past week, there was a section in there that was too good not to share.

TLDR of it came down to David Senra sharing what he’s learned from studying countless founders + himself when it comes to positive vs negative self talk.

Said there are founders out there like Jensen Huang who would wake up every morning, look in the mirror, and say, “why do you suck so much??” And others like Elon Musk who’ve basically said “my mind is a constant storm. I embrace chaos.”

That ultimately the best founders don’t linger on their wins - that they do something great, celebrate it for maybe a day, and then are back to it. They’ll go to dinner to celebrate, but before the dinner’s over, instead of thinking about that 1 thing that went well, they’re thinking about the 17 that aren’t going right.

Senra then rounded the conversation over to Brad Jacobs, who he said has been in + leading businesses for 45 years + that he realized that mindset wasn’t serving him. After countless conversations with him, Senra finally said to himself, “You love what you do, would you stop doing this? Your negative source of drive isn’t serving you anymore. Now that you love what you do + you think you’ve found your life’s work, your energy should be generative. It should be ‘I’m trying to make something for the world that I love to do and I’m very proud of.’”

That negative self-talk gets you to a point, but then your fuel source has to change because it can/will also destroy you. That in not wanting to do something for 5/10/15 years, but to want to do it forever, that source has to change.

See you next Saturday,
Sam