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Bulletproof Entrepreneur

Alan Smith
Bulletproof Entrepreneur
Latest episode

89 episodes

  • Bulletproof Entrepreneur

    #87 He arrived in the UK with £500 and sold his company to one of word's biggest banks - Anton Padmasiri

    01/05/2026 | 1h 7 mins.
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    Anton arrived in the UK with £500 in his pocket. Years later, he founded WealthOS. He recently sold it to one of the world's largest banks.
    In this episode, Alan sits down with the founder of WealthOS to talk through what the journey from arrival to acquisition actually looked like.
    We hear about the door-knocking days in suburban Surrey, and the decision to leave a senior corporate role with two children in private school and a mortgage to cover. He shares the framework he used to pick a co-founder, and why the person who scored highest was not who anyone expected.
    We get into the angel rounds, the strategic investment from Barclays, and the Liz Truss-era fundraising window that nearly ended the company.
    There is the November when the bank account was down to four figures and payroll was three weeks away. The conversation he had with his wife about pulling the kids out of school. And the call from JP Morgan that came when an exit was not on his mind.
    He also shares the principle his former chair gave him about how good businesses get acquired, and his answer to what wealth actually means after you have built and sold one.
    Links:
    Wealth OS: https://www.wealthos.cloud/
    Anton's LinkedIn: https://www.linkedin.com/in/antonpadmasiri/

    Books:
    "Dreams From My Father" by Barack Obama - https://amzn.eu/d/074kFId1
    "Range" by David Epstein - https://amzn.eu/d/0iBX3kyj
    "Build" by Tony Fadell - https://amzn.eu/d/06ueeONi

    Podcasts:
    "Invest Like The Best" by Patrick O'Shaughnessy - https://pod.link/1154105909

    This podcast is produced by Tribunista
    Sponsored by Capital Asset Management
  • Bulletproof Entrepreneur

    #86 Darya Simanovich — I Arrived in London with £300 and Built 15 Businesses. Here’s What Actually Worked.

    16/04/2026 | 1h 10 mins.
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    Darya Simanovich arrived in London 20 years ago with £300, no contacts, and barely any English. Today she runs two businesses, holds a full-time role supporting small business owners across London, mentors 400 founders a year, and has just published her first book.
    In this episode, Daria breaks down what 15 businesses across completely different industries actually taught her about failure, timing, and the kind of resilience nobody calls resilience to your face. She also shares the frameworks she gives every founder she meets, including one with a 72-hour deadline that she says determines whether anything actually gets done.
    If you have ever wondered whether the entrepreneurship path is for you, or you are already on it and wondering what separates the ones who make it, this is the conversation.
    Darya's book: https://amzn.eu/d/0j0KvWsr
    Links to other recommended resources: 
    The Artist's Way: A Spiritual Path to Higher Creativity
    Atomic Habits
    The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life
    The Psychology of Money: Timeless lessons on wealth, greed, and happiness

    This podcast is produced by Tribunista
    Sponsored by Capital Asset Management
  • Bulletproof Entrepreneur

    #85 The Music Entrepreneur Who Sold Out To Stay In - Ian Grenfell of Quietus

    02/04/2026 | 1h 12 mins.
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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
  • Bulletproof Entrepreneur

    #84 He was told his business was worth nothing. Five years later he sold it for millions - on his own terms.

    19/03/2026 | 1h 16 mins.
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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
  • Bulletproof Entrepreneur

    #83 From Bomb Survivor to 32x EBITDA Exit - Andrew Scott’s Extraordinary Entrepreneurial Journey

    05/03/2026 | 1h 16 mins.
    Send us Fan Mail
    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

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About Bulletproof Entrepreneur

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.
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