🎙 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.
From Meta to Rollshare: Seed Wins, Shutdown Truths & What’s Next | Ep 08 – How NOT to be a Founder
Sophie Adelman recounts her journey building Rollshare, from initial inspiration to navigating startup challenges and securing funding, in an interview about entrepreneurship.
16 Jun 2025
£80k Week & 40 Unused Standing Desks: Paddy McCubbin on Startup Reality | Ep 07 – How NOT to be a Founder
Paddy McCubbin recounts the early challenges of co-founding WeDo Group, including revenue spikes, VAT complications, and resource misallocation, in an interview about startup realities.
9 Jun 2025
From Recruiter to DEI Fixer: Jo Major on Free Pilots & Saying No | Ep 06 – How NOT To Be A Founder
Jo Major shares her journey from recruitment to creating a diversity and inclusion course, highlighting the challenges of adapting when initial success plateaus in this interview.
26 May 2025
From Deloitte to 721 Coffees: Keith Langbo on Bootstrapping & Hiring | Ep 05 – How NOT to be a Founder
Keith Langbo shares his journey from Deloitte to founding Kellica, discussing bootstrapping strategies and the importance of networking to fund early hires in this interview.
19 May 2025
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 firm that now supports VC-backed start-ups across Europe. In this episode, we cover: Why burnout + “nothing to lose” can be the best launchpadThe two founder traits, Claudia says, predict low attrition and high outputAgency-recruitment war stories (holes...
12 May 2025
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 almost wiped her out.Audrina went from pro Latin-ballroom dancer to VP at a performance-marketing startup—then a shock lay-off pushed her straight into Summit Chasers and, eventually, co-founding Hive with Sydney. Together they unpack: The myth of the “glamorous” founder life—and w...
5 May 2025
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...
28 Apr 2025
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 bold thinking and operational discipline. Ben reflects on the early risks, personal sacrifices, and what founders often get wrong when they try to go it alone. If you’ve ever tried to build while flying blind, this one’s for you.
25 Apr 2025
What How NOT to Be a Founder Is Really About | Episode 00
🎙️ Episode 00 – What How NOT to Be a Founder Is All About Before 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. This podcast isn’t about the highlight reel. It’s about the real journey — the screwups, the pressure, the near-misses — and what actually shapes founders. Because sometimes the best lessons aren’t in the wins. They’re in the stuff that almost broke you. New episodes every ...
Who has been a guest on How Not to be a Founder
Names identified in recent episode analyses. Showing up to five guests.
Sophie Adelman
Paddy McCubbin
Jo Major
Keith Langbo
Reach and audience
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YouTube views
3,019
Score snapshot 15 Sept 2025
Podcast Authority Score: 29 / 100
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Quality
31
Social presence
0
YouTube
65
Engagement
0
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Guest appearances
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