23mile Podcast

Kayode Odeleye
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Building an enduring company is the true proof of success 23mile Podcast brings you candid conversations with leaders who have gone the distance, sharing unfiltered lessons on scaling their companies, conquering setbacks, and engineering their exits.

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  1. 10월 28일

    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 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 dream into incredible achievements including the very first company in the world to deliver life-saving vaccines by drones. Eric endured the "pressure sandwich" of being a CEO and battling burnout but he's found the strength to "take off again" as co-founder of an AI startup Vissibl.

    1시간

  2. 10월 21일

    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 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 more than net retention, the red flags that torpedo deals, and his contrarian take on M&A advisors: "As a buyer, I prefer no bankers. As a seller, I'd always hire one."

    48분

  3. 9월 9일

    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 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 it again just 3 months later. From bootstrapping in a pandemic to landing Amazon as a client, from Citadel hedge fund to Silicon Valley to Dubai entrepreneur—this is a masterclass in grit, enterprise sales, and why the best founders think like investors. Key insights: The 3-factor framework VCs actually use to evaluate startupsHis #1 rule for winning enterprise deals (never lose control)Why "grit beats intelligence" in entrepreneurshipBuilding a company with your sibling (and why it works)Perfect for: Founders, sales professionals, anyone curious about the reality behind startup "success stories" Ziyaad now runs Qanooni, an AI platform for lawyers, and believes artificial intelligence is the next tectonic shift after the internet and mobile. Hear why he's betting his future on it.

    44분

  4. 9월 2일

    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 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 table. In this episode, he shares his unfiltered take on the realities of venture capital, the hard lessons from his own startup failures, and his M&A banker's playbook for what it really takes to engineer a successful exit. This is a must-listen on the unwritten rules of startups and finance

    48분
  5. Edwina Sharrock: The Midwife Who Delivered Her Own Life-Changing Startup Exit

    8월 19일

    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 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-tech platform by saying "yes" and figuring it out later. In this episode, she shares her playbook for funding a business on your own terms, using grants and profitability to grow without diluting her vision. You'll also hear how she engineered a life-changing exit that prioritized securing her company's mission for years to come over the highest possible price.

    56분

  6. 8월 12일

    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 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 led to a seven-figure tech exit. In this episode, Dhilon shares his powerful story of resilience, the hard lessons learned from failure, and how a personal family tragedy inspired his current mission with Story Locker, a company dedicated to preserving our most precious memories.

    49분

  7. 8월 5일

    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 $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. In this episode, Dan breaks down the lessons from his unique career. He shares the strategic differences between bootstrapping and raising venture capital, his counter-intuitive rules for building a company that’s destined for a major exit, and his definition of the one word that matters most in entrepreneurship: "Hustle." Follow 23mile on LinkedIn or X and email us at podcast@23mile.com

    43분

  8. 7월 15일

    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 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 landing Walmart as a client, but getting them to agree to Net 15 payment terms. From dropping out of university to leveraging a contract loophole to buy out his VCs, Maarij’s journey is a masterclass in patience, resilience, and winning enterprise sales on your own terms.

    47분

  9. 7월 7일

    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 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 with a former colleague, living in a one-bedroom Mumbai apartment with the grand vision of being the "Bloomberg for Retail," only to face a market that wasn't ready. Yasen gets candid about being a self-described "slow-starter," the grueling pivots from India to the Middle East and Europe before finally cracking the US market, and the continuous 12-year fundraising struggle. He then walks us through the entire M&A process, from the strategic decision to hire an advisor—which turned one potential deal into ten options and five firm offers—to closing the acquisition with Fortune 500 company, IPG. This is a masterclass in resilience, strategic pivoting, and the art of engineering a successful exit.

    41분

  10. 6월 30일

    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 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 the arts and the psychology of sales can translate into business leadership.The inside story of her management buyout of NUMA's US operations, a deal she navigated without a formal finance background.How QUAY Acceleration now guides hundreds of international startups into the competitive US market.Frances's candid advice on dealing with founder stress and the importance of being open to feedback to truly succeed

    44분
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소개

Building an enduring company is the true proof of success 23mile Podcast brings you candid conversations with leaders who have gone the distance, sharing unfiltered lessons on scaling their companies, conquering setbacks, and engineering their exits.

정보

  • 제작진
    Kayode Odeleye
  • 방송 연도
    2025년
  • 에피소드
    10
  • 등급
    전체 연령 사용가
  • 저작권
    © Kayode Odeleye
  • 웹사이트 보기
    23mile Podcast