Welcome back fellow investopreneurs!

This past week we celebrated a few moments - quick thank you if you are one of the over 200+ of you who raised your hand to get involved!

If you don’t know what Im talking about… you can read it here.

Before we jump into today’s issue…

If you have a B2B service business…

Bookkeeper…

Exit Planner…Business Brokers…

Coach… Consultant… Advisor…

Then we want to give you

Most founders think product...market fit feels like a lightning strike.

It doesn’t.

According to the co...founders of HighLevel, it feels more like confusion... churn... awkward conversations... and slowly realizing that customers are telling you something important...if you’re willing to listen.

In this week’s Bootstrapping to Billions, I sat down with HighLevel co...founders Shaun Clark, Varun Vairavan, and Robin Alex for a true boots...on...the...ground conversation about how the business really scaled.

Here are the lessons that matter.

Product...Market Fit Is a Signal You Can Measure (Not a Feeling You Guess)

Most founders think product...market fit feels like confidence.

It doesn’t.

It feels like data that keeps showing up even when you’re skeptical.

When the HighLevel founders realized they were nearing 1,000 paying customers in late 2019, they didn’t celebrate. They audited Stripe. They checked ProfitWell. They assumed something was wrong.

That’s the tell.

Real product...market fit shows up as behavior you don’t have to talk yourself into believing.

Apply this:

Ask yourself:

• Are customers paying consistently?

• Are they renewing without persuasion?

• Are they using the product without you pushing them?

If you have to explain why it’s working...it probably isn’t yet.

Churn Isn’t the Enemy...It’s the Diagnostic

HighLevel’s early customers loved the product.

Then they churned.

Not because the software failed...but because implementation took too long.

That distinction matters.

Most founders treat churn as a feature gap.
It’s usually a time...to...value gap.

Customers don’t quit because your product is bad.
They quit because the payoff is too far away.

Apply this:

Look at your last 10 churned customers and ask:

• Did they reach a first win?

• How long did it take?

• What had to happen before value appeared?

If value requires motivation, education, and discipline...you don’t have a product problem. You have an activation problem.

Stop Helping Customers...Start Helping the People Who Help Them

SMBs don’t want software.

They want outcomes.

HighLevel stopped trying to convince small business owners to “figure it out” and instead supported agencies that already had:

• Time to implement

• Context to decide

• Incentive to make it work

That single shift turned:

• Distribution into a system

• Adoption into a feature

• Support into a moat

Apply this:

Ask:

• Who already influences my customer’s decisions?

• Who benefits when my product works?

• Who has leverage I don’t?

You don’t always need more customers.
Sometimes you need better intermediaries.

Time...to...Value Is the Actual Product

Every product really sells one thing:

Speed to a meaningful outcome.

The gap between $0 and $1 matters more than $1 to $10,000.

That first win creates belief.
Belief creates patience.
Patience creates retention.

Apply this:

Define your product’s first win:

• What must happen for the customer to say “this works”?

• How fast can you get them there?

• What can you remove to make it faster?

If your onboarding requires discipline, motivation, or tutorials...you’re leaking value.

If You Can’t Afford Feedback, You Can’t Afford to Build

HighLevel paid users for feedback...often under $200 total.

They asked for money before building.

That’s not hustle.
That’s respect for reality.

People vote with dollars.
Everything else is opinion.

Apply this:

Before building your next feature:

• Ask for a small paid commitment

• Offer a refund if it never ships

• See who actually commits

If no one pays even a little...you just saved months of work.

Niche First Is a Survival Strategy

HighLevel didn’t try to win a massive market.

They started as an agency operating system.

That wasn’t positioning.
It was defense.

Big markets attract capital.
Niches protect bootstrappers.

They expanded only by following customers outward, never by forecasting.

Apply this:

Ask:

• Who would be hurt most if my product disappeared?

• Who would notice immediately?

• Who already depends on this?

That’s your real ICP...not the one in your deck.

There Was No Master Plan...Only Daily Execution

From the outside, HighLevel looks strategic.

From the inside, it was:

• Listen

• React

• Ship

• Repeat

Strategy showed up after consistent execution.

Apply this:

If you feel stuck, ask:

• What is the clearest customer problem today?

• What can I ship in 7 days to reduce it?

• What feedback will that create?

Momentum beats clarity.
Clarity follows momentum.

Software Scales Instantly...People Do Not

The hardest part of growth wasn’t product.

It was the team.

You can’t scale humans like code.
You grow:
1 → 2 → 4 → 8

Every hire needs context, empathy, and alignment.

Apply this:

If growth feels chaotic:

• You probably hired too fast

• Or without shared context

• Or without clear ownership

Teams scale by trust, not org charts.

AI Value Isn’t Hype...It’s Labor Removal

Customers didn’t want AI content tools.

They wanted:

• Assistants

• Agents

• Automation that removes work

HighLevel waited for usage signals instead of chasing trends.

Apply this:

When evaluating AI:

• What task disappears?

• What decision gets faster?

• What work stops happening?

If AI adds steps, it’s not leverage.

Don’t Chase the Exit...Chase the Day

HighLevel wasn’t built to sell.

It was built to be worth showing up to every day.

Exits happen when:

• Customers win

• Teams stay

• Momentum compounds

Apply this:

Ask:

• Would I still build this if it never sold?

• Do customers genuinely depend on it?

• Does today’s work make tomorrow easier?

Durable businesses feel boring from the inside.

The Builder’s Diagnostic

If you take nothing else, ask yourself this week:

• What is my customer actually stuck on?

• How fast do they get their first win?

• Who already has the time and incentive to help them succeed?

Solve those three...
and everything else gets simpler.