Hosted by Kayode Odeleye · 🇺🇸 US · EN · 21 episodes
Established thought leaders with verified media credentials.
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
Kayode Odeleye hosts 23mile Podcast | Founder Exits, Scaling & All the Hard Bits, a business show with 21 episodes published.
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 16
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
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 mis
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 co
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 Net
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
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 tha
"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 ca
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
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
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 "w
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.
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,
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 Middle East's pionee
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 built on a powerful philosop
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 later bought out her
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 board on the other side
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 $1 million exit, co-fo
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 his investors, returned
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 story of his 12-year j
Amber Vodegel
CEO · 28X
1 appearance on this show
James Green
co-founder and General Partner at DQventures · Brown University
1 appearance on this show
James
US Army Veteran and Historian · Wilderness Brewery
1 appearance on this show
Matt Williamson
senior front end engineer · YouTube’s Pop Goes the 60s
1 appearance on this show
Rachel Murphy
Strategy Analyst · The Grafter
1 appearance on this show
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23mile Podcast | Founder Exits, Scaling & All the Hard Bits is hosted by Kayode Odeleye. The show is categorised under business (entrepreneurship) and has published 21 episodes.
23mile Podcast | Founder Exits, Scaling & All the Hard Bits has published 21 episodes.
23mile Podcast | Founder Exits, Scaling & All the Hard Bits regularly covers business, entrepreneurship. It sits in the business category, with a entrepreneurship focus.
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Episodes of 23mile Podcast | Founder Exits, Scaling & All the Hard Bits average 53 minutes. a focused format where a clear narrative arc and tight preparation matter most.
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