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How Not to be a Founder
🎙 How Not to Be a Founder – The Darkly Funny Podcast About Startup Failure 🎙
💀 Startups are hard. Failing is harder. But at least we can laugh about it. 💀
The brutally honest podcast exploring the dark, funny, and painfully real side of startups.
Forget the LinkedIn flexes—this is where founders share their biggest mistakes, worst decisions, and absolute dumpster fire moments. It’s raw, vulnerable, and laced with enough dark humour to make the chaos bearable.
How Not to be a Founder
Luke Davis: Bootstrapped, Bias-Proof & the $20k Dot-Com Mistake | Ep 02 – How NOT to Be a Founder
Luke Davis went from “employee #31” at a fast-growing tech scale-up to co-founder of Diversifying.io, a job board tackling workplace diversity long before it was headline news.
In this conversation we cover:
- Bootstrapping in real life – why Luke still hasn’t taken VC money and how that forces “creative discipline.”
- Fund-raising vs. reality – the hoops a Black female-led team still has to jump through (including an invoice-financing deal that disintegrated the moment ID was requested).
- The $20,000 domain lesson – how ignoring the “.com” cost Luke’s team a chunk of runway.
- Life-threatening illness mid-startup – Luke’s colon-cancer battle, what it did to his mental health, and the power of therapy and marathon training in the aftermath.
- Why “hire another person” is not the default answer to every scaling problem.
If you’ve ever wondered what it really feels like to juggle growth, cash-flow panic and a health crisis—while the market mood swings on diversity—Luke lays it all out.