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How Not to be a Founder

How Not to be a Founder

By: Tom Sherwood
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About this listen

🎙 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.

© 2025 How Not to be a Founder
Economics Leadership Management & Leadership
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Episodes
  • From Ballroom to Bootstrapped — Sydney de Arenas & Audrina on Risk, Rejection & THAT Investor Horror | Ep 03 – How NOT to Be a Founder
    May 12 2025

    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.

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    56 mins
  • Luke Davis: Bootstrapped, Bias-Proof & the $20k Dot-Com Mistake | Ep 02 – How NOT to Be a Founder
    May 5 2025

    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.

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    50 mins
  • Ep 01 - Ben Read
    Apr 28 2025

    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.

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    42 mins

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