23mile Podcast
23mile Podcast
Podcast Description
Your startup has survived the early, unpredictable days and you're now wondering: what's next?
23mile is your guide to the massive opportunities and complex challenges founders face when scaling up. We focus on the game-changing moves that define a company's legacy: mastering growth, navigating mergers and acquisitions, and overcoming the obstacles that stand between you and the next level.
Each week, hear the hard-won wisdom from the founders, investors, and deal-makers who have built, bought, and sold companies for a living.
Podcast Insights
Content Themes
The podcast focuses on significant startup growth topics, including mastering exit strategies, navigating mergers and acquisitions, and facing scaling challenges, with episodes like Yasen Dimitrov's journey to a $100 million exit and Frances Simowitz's management buyout adventure.
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
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.
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