From the Trenches

Real founder stories from 18 years running a bootstrapped physical product brand — what worked, what didn't, and what I'd do differently.
08
Jul
Margins and Meltdowns Jennifer McKinley standing at the top of Harney Peak Outlook in the Black Hills, South Dakota

Three Things a Mountain Reminded Me (That I Already Knew)

Three reminders from a hike up Harney Peak — the highest point east of the Rockies. None of them were new ideas. That was rather the point.
5 min read
10
Jun
I've Already Lived Through My Version of an Economic Apocalypse

I've Already Lived Through My Version of an Economic Apocalypse

Two crises. Twelve years apart. Same founder. Same product. Completely different outcomes. Here's what changed.
4 min read
02
Jun
While Everyone's Worried About AI Taking Their Job, I'm Thinking About Yours Differently

While Everyone's Worried About AI Taking Their Job, I'm Thinking About Yours Differently

AI may disrupt white-collar work, but product founders could be in a stronger position than most realise. A counterintuitive take from an 18-year founder.
3 min read
16
Apr
You May Be Owed a Tariff Refund — Here's What to Do

You May Be Owed a Tariff Refund — Here's What to Do

If you imported goods from certain countries and paid IEEPA tariffs, you may be owed a refund. Here's how the CBP CAPE portal works and what to do with the money when it arrives.
2 min read
07
Apr
Dear Bootstrapped Founder: That Tax Bill Means You Won

Dear Bootstrapped Founder: That Tax Bill Means You Won

A tax bill means your business made money this year. Here's why that's worth celebrating — and how Profit First makes tax season almost boring for product founders.
4 min read
08
Oct
When Did We All Become "Founders"?

When Did We All Become "Founders"?

A woman at a comedy show said \"Founder\" and the room paused. It got me thinking about why we all adopted the word — and what we might be losing by running from \"small.\"
2 min read