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

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...

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% o...

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 differ...

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...

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...

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 e...

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 b...

"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 called it a plan. 1,000 days later, she sold Difrent for £13.3 million. Her team had built the NHS Jobs platform and delivered the UK's COVID home-testing servi...

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 repeat something in present tense obsessively, your brain rewires to spot the opportunities that make it real. In 2020, the wire hit his account. Week of his 40th...

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 contrarian investment thesis: buying the "venture orphans" that VCs leave behind. As CEO of Edited Capital, Krista has completed 13 acquisitions of B2B SaaS companies st...

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 "what is an entrepreneur?" before launching MUHU, the UK's first CBD-infused gin, from her bedroom. Using her journalism background as her secret weapon, she bootstrapp...

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." He restructured and split the company, finding new owners specifically to save his team's jobs, before walking away. This is the story of a founder who turned a...

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, David needs every deal to work—and he reveals exactly what that means for founders. You'll learn what makes a software company irresistible to buyers, why gross retention matters...

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 pioneering Buy Now Pay Later platform—with his sister, selling it to Australian giant Zip after 18 months, watching it get shut down, then reacquiring their own company and flipping...

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 philosophy: understanding and "gaming the system" to win. As a two-time venture-backed founder, a VC, and an M&A advisor, Mike has sat on every side of the tabl...

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 external investor to regain 100% control of the company she had built from scratch. This is the story of a midwife from a small regional town who bootstrapped a national health-te...

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 of the world to hire him as a tech CEO, even though he had zero tech or sales experience. That comeback was the catalyst for an incredible career that started behind DJ decks and...

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-founding a VC-backed trailblazer (TVision) that has raised close to $60 million, and leading the transformation of another business from $50 million to $250 million in just 18 months...

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 their capital, and bootstrapped his logistics company to an 8-figure powerhouse. In this episode, Maarij reveals why cash flow is king, and how his proudest achievement wasn't...

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 journey, which began after leaving a promising career at Boston Consulting Group with a simple mantra: "if you're not learning, just leave." He recounts starting IntelligenceNODE wi...

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 shares how she found her passion in the startup world and rose to CEO in just 18 months. This episode is a must-listen for anyone looking to forge their own path. Tune in to hear: How the discipline of th...