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

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.

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.

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: 1. Why the wealthiest founders he knows never took VC money 2. The maths VCs won't show you: why your exit needs to be £500m+ 3. Why some accelerators are giving founders bad advice 4. Hard work is only a ticket to play, not a guarantee of success 5. How to start your next thing without quitting your job cold turkey 6. Why the warm intro beats the cold pitch deck every time 7. Building a career through relationships and steady steps, not grand leaps 8. Why the UK should stop comparing itself to the US and measure its own progress If you're thinking about raising venture capital, you absolutely have to listen to this episode

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: 1. Failure requires a mourning period. James describes the end of a startup as a grieving process that requires time before starting again. 2. Traction is behavioral. Real traction exists when a customer pays for a product more than once. 3. 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 [https://www.google.com/search?q=https://linkedin.com/in/jamesgreen1] Subscribe to 23mile: 23mile.com [https://23mile.com/]

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.