23mile Podcast | Founder Exits, Scaling & All the Hard Bits

Kayode Odeleye
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  • Entrepreneurship
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23mile is the podcast for founders who want to know what it actually takes to scale, exit and survive everything in between. Featuring founders who've done it, from bootstrapped operators scaling to seven figures to venture-backed teams navigating boards, preference stacks and the pressure to grow at all costs. Plus the experts on the other side of the table. Exit negotiations, cap tables, founder economics, go to market, due diligence, fundraising and all the stuff that keeps founders up at night. Hosted by Kayode Odeleye, former investment banker and tech founder turned investor

  1. Jul 30

    It is f**king fun: HOW Jess accidentally founded a startup, scaled and exited to a public company

    Jessica Christiansen-Franks calls entrepreneurship f**king fun, and she's one of the rare founders who actually made it to an exit. Only 2% of startups ever get acquired for enough to return capital to investors and be worth the trouble. This is the story of one that did. In 2025, eight years after founding, Neighbourlytics had 20 buyers interested in acquiring the company. REA Group, a global proptech giant listed on the ASX, won. It was a fitting end to a journey that started ten years earlier, when Jess met Lucinda during her masters and ended up working for her in the non-profit Lucinda ran. Their close working relationship, including Jess running the company while Lucinda was on maternity leave, led to the two of them accidentally founding a startup. They'd gone to pitch at what they thought was a grant competition. When they won $100k, they had to register a limited company to claim the award, and Neighbourlytics was born. In this episode we cover:🔹 How she accidentally founded a startup by entering the wrong competition🔹 Why she killed $1.1M of revenue to force a pivot the board was scared of🔹 How she ran the sale, and why you hire advisors even for a small deal🔹 How she timed the exit to the AI shift that tripled the valuation🔹 Why she turned down VC money that would have pushed her into advertising Guest: Jessica Christiansen-Franks, now Managing Director at the Wade Institute of Entrepreneurship. Follow 23mile so you don't miss the next one. 23mile.com/podcast

    It is f**king fun: HOW Jess accidentally founded a startup, scaled and exited to a public company

  2. Jun 9

    4-Years without a salary: How Jinesh Vohra Built Sprive into a Top UK Finance App

    Jinesh Vohra spent fourteen years at Goldman Sachs, then left to build Sprive. He raised £240,000 on a PowerPoint, didn't pay himself for four years, and built the wrong product first. Today Sprive is at £12m ARR with 160,000 homeowners on the app. He's backed by three Dragons after his Dragons' Den pitch in February, and Sprive was the most downloaded financial app in the UK that week, ahead of Revolut, Monzo and Trading 212. In this conversation he covers leaving a well-paying job, validating an idea while still in your day job, raising across many rounds, and why he thinks now is the best time to start a business.

  3. May 11

    15-Year Overnight Success How Amber Bootstrapped a Side Project to an 8-Figure Exit to Philips

    Most founders start businesses as a means to getting rich so they can retire happy. But Amber Vodegel found out at the end of a very rare, successful exit that it's not the case. In her words: "I can guarantee you money brings zero happiness." She bootstrapped Pregnancy+ to 12 million users which culminated in a sale to Philips in an 8 figure deal, with her still owning almost 100% of the company. It wasn't all smooth sailing as her first app with a friend fell apart, and she had to work Pregnancy+ as a side hustle for many years which meant she worked on it 7pm to 11pm every night while her kids slept. Instead of retiring after her stint scaling Pregnancy+ inside Philips, she's back doing what she does best, building apps that help women. 28X is a free, privacy-first women's health app where your data never leaves your phone. This conversation covers how she engineered the exit, what it actually cost her, and why she went back for more.

  4. Apr 23

    Why Your Exit Strategy is Your Best Fundraising Tactic: Charlie Fletcher, Mischon De Reya

    Charlie Fletcher advised on over 100 M&A and fundraising deals in 2025 as Partner at Mishcon de Reya. In this episode, he explains how to run exit conversations while fundraising without killing your round, the legal mistakes that destroy founder economics even when deals close, and how to model your exit waterfall at each funding round so you understand what you'll actually make at different valuations. You'll also learn why £20M+ growth rounds became harder to access after 2021, how to position dual-track strategy to boards that resist it, and why 85% of VC-backed exits happen through M&A rather than IPOs. If you're raising or thinking about an exit, this will help you prepare better.

  5. Apr 1

    How to Raise Venture Capital and NOT Destroy Your Startup: Lessons from an Ex-VC

    The wealthiest people Kiran knows never raised venture capital. They built businesses, owned 80-90% of the equity, and exited for 7-8 figures. Kiran Mehta spent four years as a VC at Mercia Ventures. He invested in 11 companies, sat on every board, and reviewed thousands of pitch decks. Then he walked away to work directly with founders through Catenae Advisory. In this episode: Why the wealthiest founders he knows never took VC moneyThe maths VCs won't show you: why your exit needs to be £500m+Why some accelerators are giving founders bad adviceHard work is only a ticket to play, not a guarantee of successHow to start your next thing without quitting your job cold turkeyWhy the warm intro beats the cold pitch deck every timeBuilding a career through relationships and steady steps, not grand leapsWhy the UK should stop comparing itself to the US and measure its own progressIf you're thinking about raising venture capital, you absolutely have to listen to this episode

  6. Mar 3

    From High-Earning Professional to Failed Tech Founder - The Gung Ho Propaganda | James Green

    James Green lost $3 million falling for the gung ho propaganda of the tech world. He describes the end of his startup as a period of grief that took 18 months to process. In this episode, James breaks down why Scaled Networks failed, highlighting a 30% worker turn-up rate, and why building software before proving behavior was his primary mistake. He now advocates for the rational startup: building for multi million dollar outcomes and autonomy rather than the venture capital treadmill. In this episode, you will learn: Gung Ho Propaganda. Why survivor bias leads professionals to ignore the 90% failure rate of startups. The 30% Trap. Why building an app before proving market behavior through manual simulation was a $3 million mistake. The Traction Ladder. How to distinguish between polite feedback and real traction where customers pay more than once. Building for Autonomy. Why mid-career founders should target multi million dollar exits instead of unicorn valuations. Three Founder Takeaways: Failure requires a mourning period. James describes the end of a startup as a grieving process that requires time before starting again. Traction is behavioral. Real traction exists when a customer pays for a product more than once. Ownership drives wealth. A rational exit for $10 million is often a better goal for experienced professionals than a high risk unicorn target. Connect with James: linkedin.com/in/jamesgreen1 Subscribe to 23mile: 23mile.com

  7. Feb 19

    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.

  8. 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.

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About

23mile is the podcast for founders who want to know what it actually takes to scale, exit and survive everything in between. Featuring founders who've done it, from bootstrapped operators scaling to seven figures to venture-backed teams navigating boards, preference stacks and the pressure to grow at all costs. Plus the experts on the other side of the table. Exit negotiations, cap tables, founder economics, go to market, due diligence, fundraising and all the stuff that keeps founders up at night. Hosted by Kayode Odeleye, former investment banker and tech founder turned investor

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