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Currently bootstrapping a $100M portfolio, 100% in public at bootstrappercapital.com

Issue #368: The 7-year lesson

May 30, 2026

Issue #368: The 7-year lesson

What venture capital actually costs you...

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Issue #367: From $100 to an Intuit acquisition

May 23, 2026

Issue #367: From $100 to an Intuit acquisition

The hard lessons behind 25 years of bootstrapping

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Issue #366: Fired in 2016.

May 16, 2026

Issue #366: Fired in 2016.

Exited in 2025. (Operational lessons from a 7-year build)

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Issue #365: Good businesses sell cheap

May 9, 2026

Issue #365: Good businesses sell cheap

Here is why...

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Issue #364: He turned down 70 VCs

May 2, 2026

Issue #364: He turned down 70 VCs

and still exited...

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What a week...

Apr 25, 2026

What a week...

Thank you.

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Are you actually AI ready?

Apr 24, 2026

Are you actually AI ready?

Most owners aren't.

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Your OWNABLE Score is waiting for you.

Apr 23, 2026

Your OWNABLE Score is waiting for you.

See exactly where your business stands today.

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The owners who win don't do it alone.

Apr 22, 2026

The owners who win don't do it alone.

Something new today and a seat is waiting for you.

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I'm not done yet.

Apr 21, 2026

I'm not done yet.

Yesterday blew me away. So here's another one.

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A thank you.

Apr 20, 2026

A thank you.

And something I've never done before.

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Issue #363: Simple Profits is now Bootstrapper.

Apr 18, 2026

Issue #363: Simple Profits is now Bootstrapper.

Here is what changed.

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You asked for more.

Apr 17, 2026

You asked for more.

Here's what we built.

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Issue #362: If your pipeline resets every month

Apr 11, 2026

Issue #362: If your pipeline resets every month

Then it is not a talent problem. It is a design problem. And it is fixable.

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Issue #361: Why mixed revenue kills deals

Apr 4, 2026

Issue #361: Why mixed revenue kills deals

It is simply a design problem...

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OWNABLE just dropped

Apr 1, 2026

OWNABLE just dropped

If you run a real business, read this.

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Issue #360: Selling too early

Mar 28, 2026

Issue #360: Selling too early

when to know you are not ready.

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Issue #359: Your day job is a funding round

Mar 21, 2026

Issue #359: Your day job is a funding round

Here is why.

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Friday Retrospective #4

Mar 18, 2026

Friday Retrospective #4

Part 2 is here... and now we add AI

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Issue #358: What buyers actually look for

Mar 14, 2026

Issue #358: What buyers actually look for

It starts from day one.

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Friday Retrospective #3

Mar 12, 2026

Friday Retrospective #3

The #1 reason leads go cold (and how to fix it this friday)

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Issue #357: If Your business stops when you do

Mar 7, 2026

Issue #357: If Your business stops when you do

It's an expensive problem.

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Friday Retrospective 2.0 (#2)

Mar 4, 2026

Friday Retrospective 2.0 (#2)

Take your first step into the AI Economy this Friday

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Issue #356: How Bootstrapped Operators Exit

Feb 28, 2026

Issue #356: How Bootstrapped Operators Exit

The exit starts before you decide to sell

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Friday Retrospective 2.0

Feb 25, 2026

Friday Retrospective 2.0

Run your business in <1 hour per week.

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