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Showing episodes and shows of
Kayode Odeleye
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23mile Podcast
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 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 stuck between can't raise and won't die. Her firm buys at 1x revenue multiples and transforms unprofitable venture-backed startups into sustainable, profitable businesses.In this episode:How Krista raised $18M equity + $120M debt...
2025-12-04
51 min
23mile Podcast
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, 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 bootstrapped her way to two acquisition offers and sold to Next Frontier Brands at age 25.In this episode, Sally shares the tactical playbook: how she staged product photos with a house plant and sparkling water...
2025-11-13
44 min
23mile Podcast
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 "...
2025-10-28
59 min
23mile Podcast
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 al...
2025-10-21
48 min
23mile Podcast
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 master...
2025-09-09
44 min
23mile Podcast
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...
2025-09-02
48 min
23mile Podcast
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...
2025-08-19
55 min
23mile Podcast
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...
2025-08-12
48 min
23mile Podcast
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...
2025-08-05
43 min
23mile Podcast
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...
2025-07-15
46 min
23mile Podcast
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.
2025-07-08
40 min
23mile Podcast
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...
2025-06-30
43 min
The Next Big Thing
What are VCs really doing in the GCC region? | The Next Big Thing - S01 E01
The Next Big Thing is the 24six9 Community Podcast.Our goal is to foster collaboration and synergy within the startup community and empower aspiring entrepreneurs by sharing the experiences and wisdom of successful startup foundersJoining us on this episode:► Jamil Shinawi - Co-Founder and CEO of AHOYhttps://www.linkedin.com/in/jamilshinawi/► Karim Helal - Co-Founder and CEO of ProTenders Inc.https://www.linkedin.com/in/khelal/► Kevin Czok - Co-Founder of Hotel Data Cloudhttps://www.linkedin.com/in/kevinczok/► Kayode Odeleye - Co-Founder of CAENAhttp...
2023-09-12
56 min
Not My First Guess
Make the earth move: how to build a sustainable sextech business with Farah Kabir, Co-founder of HANX
Today I’m joined by Farah Kabir, Co-founder of HANX.One day, while enjoying a stable career in Asset Management at Goldman Sachs, Farah stood in line at her local Boots ready purchase a box of condoms when she realised her boss was standing behind her.Utterly mortified, Farah felt the very relatable pang of shame rise within her until… she suddenly thought “actually, why should I be embarrassed about this?” and so over a bottle (or two) of wine, she decided to jump into bed with her best friend Sarah (who also happens to be a doc...
2023-07-25
56 min
GEORGE FOX TALKS
LEADERSHIP | Celebrating Adversity and Co-Creating With God
In this episode, our host Dave Tussing meets with finance professional Kayode Odeleye to discuss relationship with God, integrity, and adversity as they relate to career building. What kind of adversity is helpful, and how does faith in God speak into the way we lead and plan our lives?Kayode is the Founder and CEO of Caena.io, a financial technology company building tools to simplify the fundraising process for startups and private investment firms. Before Caena, he worked for 14 years in financial services across retail banking, strategy and investment banking. His most significant stint was in i...
2021-10-26
45 min