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Bulletproof Entrepreneur

Bulletproof Entrepreneur

By: Alan Smith
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A podcast for entrepreneurs – reverse engineering the formula for successful scale, sale and exit. Inspired conversations with world-class entrepreneurs and the specialists who support them.© 2023 Bulletproof Entrepreneur Economics Leadership Management & Leadership Personal Finance
Episodes
  • #85 The Music Manager Who Sold His Business, Paid Zero Tax, and Never Lost Control - Ian Grenfell
    Apr 2 2026

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    Ian has spent 45 years in the music industry, managing Simply Red, Simple Minds, The Pretenders, and Suede. He started at 17 with a boot full of vinyl and a two-litre Cortina, driving 1,200 miles a week as a sales rep.

    He went on to oversee the biggest self-released album in history - Simply Red's Home, which outsold most Taylor Swift records and still holds the record today!

    But Ian's story isn't just about music.

    It's about what happens when a founder tries to exit a business built entirely on relationships, trust, and instinct. After a bruising experience selling 50% to Live Nation and rejecting a buyout offer before his plane left the runway at Heathrow, Ian found a route almost nobody in his world had heard of - and it changed everything.

    This is a conversation about sliding doors moments, creative courage, knowing when enough is enough, and an exit strategy that let him cash out, stay involved, and reward every person who helped him build it.




    This podcast is produced by Tribunista

    Sponsored by Capital Asset Management

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    1 hr and 12 mins
  • #84 He was told his business was worth nothing. Five years later he sold it for millions - on his own terms.
    Mar 19 2026

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    Neil Osmond never set out to be an entrepreneur. He was a pharma executive with a steady job, a young family, and no savings when a friend showed him something on a computer that he couldn't stop thinking about.

    What followed was a 15-year journey - mapping the London Olympics, pivoting into healthcare, nearly running a glorified lifestyle business, and eventually selling Earthware to a global medical communications group after more than ten first-stage offers.

    In this episode, Neil walks through all of it: the brutal feedback that changed his direction, how he used Vivid Vision, EOS, and 8 Agencynomics benchmarks to transform the business, why knowing your number before you sell is non-negotiable - and what true wealth looks like when the chapter is finally closed.

    Books mentioned:

    Maverick – Ricardo Semler | Business Model Generation – Osterwalder & Pigneur | Agencynomics – Spencer Gallagher & Peter Hoole

    Connect with Neil on LinkedIn: https://www.linkedin.com/in/neilmeosmond/

    Subscribe to the Bulletproof Entrepreneur newsletter: https://alan-smith-bulletproofentrepreneur.kit.com/newsletter

    Follow Alan on LinkedIn: https://www.linkedin.com/in/alancapital/


    This podcast is produced by Tribunista

    Sponsored by Capital Asset Management

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    1 hr and 17 mins
  • #83 From Bomb Survivor to 32x EBITDA Exit - Andrew Scott’s Extraordinary Entrepreneurial Journey
    Mar 5 2026

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    He survived a bomb at four years old. Lost everything in his thirties. Then built a group of companies employing nearly 100 people and sold his media business for 32 x EBITDA.

    I sat down with Belfast-born entrepreneur Andrew Scott for one of the most honest conversations about failure, resilience, and reinvention you’ll hear anywhere.

    Andrew shares the full story - from growing up during the Troubles, to arriving in London at 18 with nothing, to the moment he sat in a clapped-out BMW on a beach and thought it was all over. And what happened next.

    Topics covered: surviving childhood trauma, the power of work ethic, building and losing businesses, the Purpose Plan Execute framework, creative deal-making, company culture, AI in business, and achieving a 32x EBITDA exit.

    Links

    🔗 Connect with Andrew: https://www.andrewscott.bio/

    🔗 Subscribe to the Bulletproof Entrepreneur newsletter: https://alan-smith-bulletproofentrepreneur.kit.com/newsletter

    🔗 Follow Alan on LinkedIn: CLICK HERE


    This podcast is produced by Tribunista

    Sponsored by Capital Asset Management

    Show More Show Less
    1 hr and 17 mins
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