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How Not to be a Founder
🎙 How Not to Be a Founder – The Darkly Funny Podcast About Startup Failure 🎙
đź’€ Startups are hard. Failing is harder. But at least we can laugh about it. đź’€
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.
Episodes
7 episodes
From Recruiter to DEI Fixer: Jo Major on Free Pilots & Saying No | Ep 06 – How NOT To Be A Founder
After 25 years at a recruitment desk, Jo Major never planned to start until the 2020 social justice wave, which exposed a training gap no one was filling.She left a trade-body role, ran six free beta programmes, and launched a...
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Season 1
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Episode 6
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43:14
From Deloitte to 721 Coffees: Keith Langbo on Bootstrapping & Hiring | Ep 05 – How NOT to be a Founder
Keith Langbo never planned to be a founder.He grew up watching his dad spend 50 years in one company, started his own career at Deloitte, then became employee #5 (and eventually president) of a high-growth recruitment start...
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Season 1
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Episode 5
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55:57
Claudia Green: Rock-Bottom to Resilient—Hiring Truths & Founder Mistakes | Ep 04 – How NOT to Be a Founder
Claudia Green went from agoraphobic teen to boiler-room recruiter, then hit absolute rock bottom in 2019—job gone, relationship over, family illness.Lying beside her sick grandma, she registered “Scaling Up,” a fractional talent & HR...
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Season 1
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Episode 4
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46:04
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From Ballroom to Bootstrapped — Sydney de Arenas & Audrina on Risk, Rejection & THAT Investor Horror | Ep 03 – How NOT to Be a Founder
Two totally different routes, one very real destination: founder reality.Sydney de Arenas grew up around family businesses, quit a soul-crushing sales job at 23 and never looked back—until a bad hire in Paris almos...
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Season 1
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Episode 2
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56:21
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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:Boots...
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Season 1
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Episode 2
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50:23
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Ep 01 - Ben Read
Ben Read joins Tom to explore the dynamic between visionary founders and the integrators who keep them grounded. From 10-ideas-a-week chaos to the reality of execution, this episode dives into what happens when startups lack the balance between...
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Season 1
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Episode 1
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42:02
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What How NOT to Be a Founder Is Really About | Episode 00
🎙️ Episode 00 – What How NOT to Be a Founder Is All AboutBefore we dive into the real stories, the mistakes, and the moments nobody posts on LinkedIn, I wanted to quickly share why I started How NOT to Be a Founder<...
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Season 1
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Episode 1
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1:38
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