How Not to be a Founder

Tom Sherwood
  • 5.0 (1)
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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.

Episodes

  1. £80k Week & 40 Unused Standing Desks: Paddy McCubbin on Startup Reality | Ep 07 – How NOT to be a Founder

    JUN 16

    £80k Week & 40 Unused Standing Desks: Paddy McCubbin on Startup Reality | Ep 07 – How NOT to be a Founder

    £80k in week one… then the VAT bill hit. Paddy McCubbin walked away from a cushy director role to co-launch WeDo Group with two friends. Day-three revenues smashed £80,000, but a four-month wait for a VAT number froze the cash, and an impulse order of 40 adjustable desks soaked up the runway. In this episode, we unpack the un-Instagrammable side of a “rocket-ship” start-up: The Hacker–Hippie–Hustler trio – why three very different co-founders trump going solo.HMRC limbo – billing clients you can’t invoice and the domino effect on cash-flow.Buying mistakes – the stand-up-desk fiasco & other ego-driven purchases.Keeping momentum – rapid-fire idea testing (and killing) inside a recruitment scale-up.Fractional firepower – hiring a part-time CFO and CMO before you think you can afford them.Authentic brand – flip-flops in a CFO pitch, paddle-board meetings and why “fake it till you make it” kills trust. If you’ve ever wondered what happens after the champagne-spraying LinkedIn post, this is the real balance sheet. Listen in for hard numbers, hard lessons, and a reminder that the fires you fight are often the ones you lit yourself.

    44 min
  2. From Recruiter to DEI Fixer: Jo Major on Free Pilots & Saying No | Ep 06 – How NOT To Be A Founder

    JUN 9

    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 modular ED&I course that took off during the 2021 boom. Then budgets froze, partners drifted, and Jo had to reinvent everything, while ditching alcohol and hiring a mindset coach. What you’ll hear: • Why did she build the whole brand before writing a single invoice? • The 6-client, no-fee beta that generated her first paid testimonials. • Pivoting from 6-week courses to 2-hour workshops when L&D cash dried up. • Killing the “your worth = last month’s billings” habit from agency life. • Sobriety, strength-training and a coach who reframed confidence. • The partnership that cost a new Ltd, website and trademarks—then fizzled. • Final lesson: sell the idea first; build the slides only after someone buys. A candid playbook on staying relevant when the hype cycle vanishes.

    43 min
  • 2 Episodes

About

🎙 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.

Information

  • Creator
    Tom Sherwood
  • Years Active
    2K
  • Episodes
    2
  • Rating
    Explicit
  • Copyright
    © 2025 How Not to be a Founder