Where were you when I was broke?

Ever notice how people show up loudest after you’ve already won? This episode digs into why founders often get the least support when the risk is highest—and the most opinions once success is “de-risked.” Will shares early moments of having virtually no safety net (including starting with $19, dropping out, and getting doubted), contrasted with the few timely “bricks” that actually changed his trajectory—like a risky $10K loan and a friend’s family offering a place to stay for the holidays. They unpack how funding wins, press, and exits attract late-arriving fans, opportunists, and advice that can derail post-success decisions, and why founders should take inventory of who truly showed up when things looked impossible—and be that kind of support for other founders.

00:39 Elon Money Opinions

02:55 Guidance Counselor Doubt

04:13 Early Support Matters

05:44 Nineteen Dollars Start

06:53 Ten Thousand Loan

09:55 Wide Angle Victory

10:38 Doubt Chokes Founders

11:38 Young Founder Respect

14:59 I Told You So Bias

18:49 Funding Round Whiplash

20:20 Recruiters Disappear