23mile Podcast | Founder Exits, Scaling & All the Hard Bits
Kayode Odeleye
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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…
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.…
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…
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…
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,…
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…
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…
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…
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,…
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…
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…
From Wall Street to 2x Exited Founders: How these Siblings Built and Sold the Same Startup Twice
What happens when your startup gets shut down right after a life-changing exit? You buy it back and sell it again.Former Wall Street analyst Ziyaad Ahmed shares the wild story of building Spotii—the…
Gaming the System: An M&A Banker's Playbook for Engineering the Perfect Exit | Mike Bank
Mike Bank once quit his high-paying M&A job at Citibank. When his boss asked why he was leaving, his answer was an epic: "I have no idea." That leap into the unknown was the start of a career…
Edwina Sharrock: The Midwife Who Delivered Her Own Life-Changing Startup Exit
Edwina Sharrock’s founder journey is a powerful lesson in trusting your gut and taking control. After appearing on Shark Tank Australia and securing a deal, she made a bold move. She rejected it. She…
From DJ Decks to Seven Figure Exit: Scaling a Tech Startup With the Help of a Six-Pack
After his dream restaurant was crushed by a corporate giant, Dhilon Solanki hit rock bottom. His response? A six-month fitness journey that forged a level of discipline so powerful, it convinced a…
From Teenage Founder to Scaling a $250M Business: Dan Schiffman on Building, Exits, and Pivots
Dan Schiffman founded his first tech startup at 15, almost 25 years ago. Since then, he has built a playbook that covers every stage of the founder journey: bootstrapping an e-commerce startup to a…
Scaling to 8 Figures after Rejecting VC: Maarij Rehman on How to Win by Nailing Enterprise Sales
What happens when you raise $250,000 and get into Techstars... only to realize the venture path is a trap? Maarij Rehman, Co-founder & CEO of Envoi, shares the unfiltered story of how he rejected…
Yasen Dimtrov | From Slow-Starter to $100 million Fortune 500 Exit
What does it take to turn a startup into a $100 million exit? For Yasen Dimitrov, the Co-founder of IntelligenceNODE, the answer is one word: patience.In this episode, Yasen shares the unvarnished…
From Opera to Owner: Frances Simowitz on Buying an Accelerator and Guiding Global Startups into the US
In this kickoff episode, we're joined by Frances Simowitz, a CEO whose path to success was anything but linear. From aspiring opera singer to teacher, nanny, and airport retail associate, Frances…
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23mile Podcast | Founder Exits, Scaling & All the Hard Bits has published 19 episodes since June 2025, covering topics in Business, Entrepreneurship.
23mile Podcast | Founder Exits, Scaling & All the Hard Bits is currently highly active with new episodes monthly. Average episode length is 51m.
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