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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
From Ballroom to Bootstrapped — Sydney de Arenas & Audrina on Risk, Rejection & THAT Investor Horror | Ep 03 – How NOT to Be a Founder
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Tom Sherwood
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Season 1
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Episode 2
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 why their bank balances said otherwise.
- Why early wins can be dangerous (including the car Audrina wishes she’d never bought).
- Sydney’s jaw-dropping investor meeting that turned into a personal-space assault—and how she rebuilt her fundraising strategy.
- A Guatemalan hostel “fridge scam,” tornado-dodging sales calls, and other moments you truly can’t make up.
- What not to do next: overspending, saying yes to every client, and building a company that can’t survive without you.
Raw, practical and occasionally ridiculous—exactly what this show is about.