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How Not to be a Founder

How Not to be a Founder

著者: Tom Sherwood
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🎙 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
マネジメント・リーダーシップ リーダーシップ 経済学
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  • Claudia Green: Rock-Bottom to Resilient—Hiring Truths & Founder Mistakes | Ep 04 – How NOT to Be a Founder
    2025/05/19

    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 launchpad
    • The two founder traits, Claudia says, predict low attrition and high output
    • Agency-recruitment war stories (holes-in-shoes firings, anyone?)
    • Her biggest founder mistake: kindness that crippled the team
    • How to be both a decent human and an authoritarian leader—no, it’s not easy


    Raw talk on resilience, people problems and paying maternity out of your pocket.

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    46 分
  • From Ballroom to Bootstrapped — Sydney de Arenas & Audrina on Risk, Rejection & THAT Investor Horror | Ep 03 – How NOT to Be a Founder
    2025/05/12

    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 分
  • Luke Davis: Bootstrapped, Bias-Proof & the $20k Dot-Com Mistake | Ep 02 – How NOT to Be a Founder
    2025/05/05

    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 分

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