Currently bootstrapping a $100M portfolio, 100% in public at bootstrappercapital.com
Jul 25, 2026
A bootstrapped founder on deal blinders, sunk cost, and starting over
Jul 18, 2026
The business that started in a hospital bed.
Jul 11, 2026
How a bootstrapped agency survived cash flow gaps on the way to a clean exit.
Jul 7, 2026
50th Episode Retrospective
Jul 4, 2026
Something BIG is coming on Tuesday!
Jul 3, 2026
This is going to make you rethink everything....
Jun 27, 2026
One pivot. And one exit. Here is what he learned.
Jun 20, 2026
How one knockout changed everything...
Jun 13, 2026
And what it actually costs you.....
Jun 6, 2026
This is what holds when the edge disappears overnight
May 30, 2026
What venture capital actually costs you...
May 23, 2026
The hard lessons behind 25 years of bootstrapping
May 16, 2026
Exited in 2025. (Operational lessons from a 7-year build)
May 9, 2026
Here is why...
May 2, 2026
and still exited...
Apr 25, 2026
Thank you.
Apr 24, 2026
Most owners aren't.
Apr 23, 2026
See exactly where your business stands today.
Apr 22, 2026
Something new today and a seat is waiting for you.
Apr 21, 2026
Yesterday blew me away. So here's another one.
Apr 20, 2026
And something I've never done before.
Apr 18, 2026
Here is what changed.
Apr 17, 2026
Here's what we built.
Apr 11, 2026
Then it is not a talent problem. It is a design problem. And it is fixable.
Apr 4, 2026
It is simply a design problem...
