Hey Reader,

You don't grow out of selling. You grow through it.

Sales is just concentrated empathy plus action. You’ve already got both. I hope.

Sales is about deeply understanding someone else's problem (empathy) and caring enough to do something about it (action). That’s not “selling" - that’s serving with conviction. To not sell it, would be selfish :)

But selling evolves. Early customers buy you. The chaos. The charm. The promise. That's where you thrive.

Later customers? Expect some clarity. Consistency. Confidence. Your messy brilliance won’t scale unless it's wrapped in a process. But process cannot exist without deep founder signal.

Even after customer 1, you think your sales role changes, and it kinda does, yes. But your proximity to the sale can't ever disappear.

It just shifts very slightly.

I've hammered the importance of sales in past newsletters.​
​Founder Sales. Share Of Mic. Partners. xxx-Led Growth.
Yes, I'm about to do it again.

There's a difference between redundancy and repetition....

Redundancy is noise. The same thing over and over.
Repetition is how we learn. Driving home what matters until it sticks.

Everything has changed in 2025, one truth now matters more than ever:

Investors aren’t throwing money at top-line growth anymore. They want.

Stickiness. Retention. Expansion.

They’re funding customer obsession over customer acquisition.

The playbook is being rewritten in real time, this is not a “sell more” newsletter. (But also sell more) It’s about reframing your relationship with sales as your mind, your investors, your team, try and push you out of it.

So.. Just for a second. Stop with the engineering.

Sell.​
Before building.
While building.
After building.
​Sell.

Get in traffic. If you’re early, figure out what you can sell based on the problem you’re solving. Solve that.

Scale is great, we all dream of it, sure, we want more than eight people to care. But if eight people care deeply, there’s probably an arena behind them.

Make those 8 happy. Do it again. That’s the secret to scale. That’s it.

And if you’re already live, already doing revenue, already pushing real product and thinking this is a message isn't for you? Still no.

You’re likely blind to how people drop off. No funnel observability. No clarity on what users do or don’t do. I imagine, you likely cannot answer some very simple questions about your users…

If churn is on the dashboard, retention is part of sales too.

But most importantly. You don’t get to delegate your way out of sales. You don’t get to rebrand as the “product” founder and hide in design systems. You’re not done selling.

“I’m not a natural salesperson” / “I’m an introvert” / “I’m an engineer/product person at heart”

I don’t care.

Sales isn’t about being smooth or extroverted. It’s about caring enough about your solution to have the hard conversations. It’s about being obsessed enough with the problem to listen for the answers.

The best founders I know are awful at sales, but they care so f'n much, customers get pulled in anyway. The number of meetings I have listened to where the founder fumbles the pitch, misses the point, goes way over time, shows "one more feature" and ignores any form of next steps...

But their obsession is contagious. People buy where the founder is heading.

So stop hiding behind a self-imposed label (or excuse).
​
​REMINDER: Sales is just concentrated empathy plus action.

All the way up to a few million in ARR— You know the problem better than anyone. You feel the objections before they’re spoken. You know the pitch that’s off by 1% before anyone else notices.

So you know the moment you step out of traffic, you start losing signal.

And without signal, your strategy is now storytelling. Your deck gets prettier. But it stops getting truer.

And signal is what gets you past where you are now:

• Your adjacent SKU
• Your next module
• Your segmentation unlock
• Your upsell pathway

I have a billionaire client. Yup.
Why would a billionaire founder have me as a coach?
Because coaching isn’t about teaching. It’s about pressure.

Perspective. Pattern recognition. It’s about having someone who’s not inside the machine but still knows how it runs. Someone who’s built. Sold. Shipped. Who can call bullshit without posturing. Who gets it.

That’s something that took me a long time to learn, to stop chasing answers and start valuing perspective.

They don’t need me to tell them how to build. They need someone who can help them see. He doesn’t do 99.8% of the work. But he is as close to the sale as anyone on the team.

In his words: "the comma is in the signals, not the dashboard" - should have him write the newsletter.

The data might tell you what happened but the sale will tell you why.

Founders who stop selling lose the loop that drives the learning, the urgency, the velocity, and perhpas even the conviction.

Selling isn’t just about demos and deals. It’s about you staying as close as possible to whats real.

Another founder I work with is running top-of-funnel. Strong campaigns. Smart targeting. But hadn’t called a single user who signed up and bailed.

Thirty minutes on Zoom. Three real (rather obvious in hindsight) reasons. One change to onboarding. Results changed. That simple.

It’s not magic. > Sales is all the way through to retention. > Retention is sales. Expansion is sales. > Sales is the entire lifecycle of customer success.

Sell to get. Sell to retain. Sell to expand. Sell to survive.

Let's frame this for the right now we are all living.

AI is stripping the value out of anything generic, replaceable, or easy to build. Capital efficiency is the new growth. Retention is the new god metric.

I’m watching founders doing $100K+ in MRR struggle to raise.
Not because the top-line isn’t working. Because the signal isn’t.

Not enough stickiness. Not enough usage depth. Not enough retention clarity. A narrative built on momentum and exciting new features doth not lead to moat building.

Investors now want to see customers who aren’t just buying but they’re staying, expanding, advocating.

Exactly how I opened this email: VCs aren’t funding customer acquisition anymore. They’re funding customer obsession.

That’s sales. In the trenches. Retention-obsessed. Never-ending sales.

Yes, it’s hard. Yes, you want to step back. Yes, the team wants you to scale.

But I’ve seen too many startups stall because the founder tries to “mature” too early. Too quietly. Too comfortably.

And no, selling doesn’t always mean money.

It’s time. It’s attention. It’s commitment. It’s effort. It’s a user showing up to do a thing that matters. Again. And again.

That’s value exchange. That’s signal gained. That’s selling. That’s how you test your assumptions in public.

That’s it. That’s the big secret.

Unless you know. Like actually know. Then ignore me. Kinda.

Guessing doesn’t scale. Conversations can.

As always, if I can be of service, feel free to grab time.

LFG.

-- James

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