23mile Podcast

Kayode Odeleye
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Building an enduring company is the true proof of success 23mile Podcast brings you candid conversations with leaders who have gone the distance, sharing unfiltered lessons on scaling their companies, conquering setbacks, and engineering their exits.

  1. 10H AGO

    From Failed YC Fundraise to Life-Changing Exit | Matt Williamson

    Matt Williamson and his co-founder James targeted $1.5M for their seed round during YC Demo Day. They walked away with just $750K. At the time, it felt like failure. A year later, Matt realised it was the best thing that happened to them. With under $1M raised, zero marketing spend, and a 4-person team, they scaled Vizzly to a life-changing exit to WPP's Gain Theory in under 3 years. In this episode, Matt breaks down the 100% customer churn that forced a pivot six weeks before Demo Day, why Tom Blomfield told them to stop fundraising and focus on revenue, and how a small preference stack turned a modest exit into a major outcome. If you've ever wondered whether raising less might actually be more, this one's for you.

    54 min

  2. FEB 3

    Want to Raise VC? Here's What LPs Actually Look For | Sion Evans

    Most founders don't understand how venture capital actually works. Sion Evans does. He sits at the top of the capital stack, picking the VCs who pick the founders. Sion is Managing Director at VenCap, a fund-of-funds that's been in the game for almost 40 years. $2 billion deployed. 500+ fund commitments. Exposure to Google, Airbnb, Stripe, SpaceX, OpenAI, Anthropic. In this episode, Sion breaks down the venture maths that most founders never see: why top funds lose money on 60% of their deals and still outperform, what a "fund returner" actually means for your startup, and why the top 1% of exits generate over half of all venture returns. If you're raising capital or thinking about it, this is the episode.

    1 hr

  3. JAN 20

    No Pretty F*cking PowerPoints: How Rachel Sold for £13.3m in 1,000 Days

    "Give me 50% of the shares and we'll get this thing sold for eight figures within five years." That was Rachel Murphy's pitch when she joined a small recruitment firm in 2017. Most people would call it delusional. She called it a plan. 1,000 days later, she sold Difrent for £13.3 million. Her team had built the NHS Jobs platform and delivered the UK's COVID home-testing service in just 8 days. Then came the part she hadn't planned for: the exit left her empty. Her identity was gone. She went to war zones, did plant medicine, and eventually built The Grafter to help other founders avoid the same blindspot. This is the complete story of building to sell – the hard graft, the highs and surviving what comes after.

    1h 3m

  4. JAN 6

    I'm Retiring at 40: How Lloyed Lobo Turned Community Into a Life-Changing Exit

    For 10 years, Lloyd Lobo told his wife the same thing: "I'm retiring at 40." She thought he was delusional. He'd already burned through $6M on failed ventures. But Lloyd understood something about neuroscience: when you repeat something in present tense obsessively, your brain rewires to spot the opportunities that make it real. In 2020, the wire hit his account. Week of his 40th birthday. Exactly as predicted. He'd built Boast AI to $10M ARR with $0 spent on ads. Community replaced his entire marketing budget. Then 2 weeks later, he was in the ICU unable to breathe. In this episode, Lloyd shares the unfiltered story of building, exiting, and nearly dying: The manifestation neuroscience that actually worked (not vision boards)How pizza nights scaled to $10M ARR with zero ad spendThe Wizard of Oz MVP strategy that beat KPMGWhy their first conference literally caught fireThe brutal health cost of success nobody warns you aboutHow his wife rebuilt him from ICU to Ironman fitnessI'd love to say this is a highlight reel but it's not. Lloyd talks about being absent at all 3 of his kids' births, the minority shareholder trap after selling majority control, and the moment in ICU when he realised his kids didn't know him. From refugee to life-changing exit to nearly dying to transformation. Real stories about exits, scaling, and the messy stuff that doesn't make it into press releases.

    59 min

  5. 12/04/2025

    Zombie Startups: How Losing a $1B Fintech Platform Inspired a Contrarian Bet on VC Failures

    Krista Morgan built a fintech company that processed $1 billion in transactions and scaled to $10M in revenue. Then it collapsed in 90 days due to fraud. Instead of walking away, she turned that painful experience into a contrarian investment thesis: buying the "venture orphans" that VCs leave behind. As CEO of Edited Capital, Krista has completed 13 acquisitions of B2B SaaS companies stuck between can't raise and won't die. Her firm buys at 1x revenue multiples and transforms unprofitable venture-backed startups into sustainable, profitable businesses. In this episode: How Krista raised $18M equity + $120M debt for P2B InvestorThe fraud that took her company from solvent to insolvent overnightExecuting a 90-day restructuring and saleWhy 75% of VC-backed startups fail (and how to rescue them)The 100-day playbook: Salesforce for 11 opportunities vs. Google SheetsWhat founders must understand before taking venture capitalWorking with VCs during distressed situationsHow to win over founders who are stuck between optimism and realityKey Takeaways:"I realized when I sold my company that there was so much value capture that was just lost. That is the core of our thesis." (Krista Morgan) Connect with Krista:LinkedIn: linkedin.com/in/kristamorganCompany: editedcapital.com 23mile brings you candid conversations with leaders who've gone the distance. Real stories about scaling, exits, and the messy stuff that doesn't make it into press releases. Hosted by Kayode Odeleye: https://www.linkedin.com/in/kayodeodeleye/ Subscribe to 23mile for regular episodes with founders who've actually gone the distance. Hit follow so you don't miss the next story.

    51 min

  6. 11/13/2025

    From £1,000 to Over £1Million: How Sally Wynter Bootstrapped MUHU to an Exit in 5 Months

    Sally Wynter achieved what most founders only dream of. Remarkably, she did it without connections, capital, or a single penny spent on advertising. Growing up on free school meals in North London, Sally had to Google "what is an entrepreneur?" before launching MUHU, the UK's first CBD-infused gin, from her bedroom. Using her journalism background as her secret weapon, she bootstrapped her way to two acquisition offers and sold to Next Frontier Brands at age 25. In this episode, Sally shares the tactical playbook: how she staged product photos with a house plant and sparkling water to unlock pre-orders, convinced distilleries to work for free, and leveraged earned media to drive growth. But she doesn't sugarcoat it—she also opens up about the mental health toll, the bittersweet reality of losing control post-acquisition, and how burnout nearly broke her this year. Now building Hunch, an AI-powered platform democratizing career opportunities for Gen Z, Sally proves that resourcefulness beats resources every time. What you'll learn: How to bootstrap a product business on £1,000PR strategies that replace advertising spend entirelyThe unfiltered truth about M&A as a first-time founderTurning disadvantages into competitive advantagesBuilding multiple ventures post-exitGuest: Sally Wynter | Founder, Hunch & MUHU Spirits (exited) Connect: Visit gethunch.com | Follow Sally on LinkedIn and TikTok

    44 min

  7. 10/28/2025

    How Eric Peck Piloted Swoop to a $100m Offer, Crashed, and Took Off Again

    He raised $30M. He got a $100M acquisition offer... and turned it down. When a second M&A deal that could have saved his company was rejected by the board, it crashed. But like a true pilot, Eric managed a "soft landing." He restructured and split the company, finding new owners specifically to save his team's jobs, before walking away. This is the story of a founder who turned a dream into incredible achievements including the very first company in the world to deliver life-saving vaccines by drones. Eric endured the "pressure sandwich" of being a CEO and battling burnout but he's found the strength to "take off again" as co-founder of an AI startup Vissibl.

    1 hr

  8. 10/21/2025

    Building a Company That Gets a Buyer Excited: The Private Equity Playbook

    What does it mean to build a startup that "can sell, but doesn't have to"? This week, we sit across the table from David Czarny, a private equity buyer who's closed 10 software acquisitions. Unlike VCs hunting moonshots, David needs every deal to work—and he reveals exactly what that means for founders. You'll learn what makes a software company irresistible to buyers, why gross retention matters more than net retention, the red flags that torpedo deals, and his contrarian take on M&A advisors: "As a buyer, I prefer no bankers. As a seller, I'd always hire one."

    48 min
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About

Building an enduring company is the true proof of success 23mile Podcast brings you candid conversations with leaders who have gone the distance, sharing unfiltered lessons on scaling their companies, conquering setbacks, and engineering their exits.

Information

  • Creator
    Kayode Odeleye
  • Years Active
    2025 - 2026
  • Episodes
    16
  • Rating
    Clean
  • Copyright
    © Kayode Odeleye
  • Show Website
    23mile Podcast