# Josh Krafchick | Follow the Money

By: Justin Abrams
Published: 2026-10-07

Where does the next dollar go? Josh Krafchick asks it of every client, and of himself.

Josh trained in actuarial science, worked inside big financial firms, then walked away to build custom money plans for real people. Today he advises tech professionals holding company stock through 369 Financial, and he runs a public strategy on Dub that anyone can copy.

The conversation also goes to the stretch where Josh sold his house near the beach and lived on twenty dollars a day.

We get into:

* What an actuary actually does, explained with a bus and a bazooka
* The one question behind every money decision
* Charlie Munger's reverse thinking: ask what would destroy your company first
* When credit card interest costs less than pulling cash out of the business
* Toll booths, subscriptions, and smoothing out boom and bust cash flow
* How raising too much money quietly shrinks a founder's payout
* Two partnerships that went sideways, and a buyback paid in $6,666.66 installments
* Wants versus needs, and why the dream list costs less than it feels
* Why Warren Buffett built most of his wealth after sixty

Connect with Josh:
LinkedIn: https://www.linkedin.com/in/joshua-krafchick-46523131/
369 Financial: https://369financial.com/

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