$100M Exits with Jason Kirby
In this podcast, we uncover the untold stories of founders who have weathered the highs and lows of raising capital. We go beyond the headlines and Techcrunch funding news articles to explore the uncharted territories of the fundraising landscape. In each episode, we'll sit down with founders from various industries who have raised venture capital to bring their visions to life. They'll open up about their personal journeys, fundraising tactics & more. If you're a founder, this podcast offers a ton of value & insights you can apply to your fundraising journey. Don't forget to hit subscribe!
Episodes
From building startups to backing the future of warfare, this episode covers what founders need to know about capital, defense tech, and AI.
Brad Harrison, Founder and Managing Partner of Scout Ventures, shares how fast defense technology is evolving—and why selling into this space is harder than most expect.
He explains how AI, drones, and autonomous systems are reshaping warfare, and why success requires more than a strong product—...
From building and exiting companies to deploying capital at a $1.8B investment firm, George Alifragis has seen both sides—as an operator and now a private credit investor at Metropolitan.
In this episode, he breaks down the transition from operator to investor, lessons from scaling a global tech company, and how that shapes how he evaluates businesses today.
He shares what really drives EBITDA growth, what makes a company att...
Jess Mah has built, scaled, and backed companies across multiple waves of Silicon Valley—but what she’s seeing now is different.
In this episode of $100M Exits, she explains why even unicorn founders are under pressure in the AI era, where success is no longer about headcount, hype, or old playbooks. AI is compressing execution timelines, raising the bar for traction, and making many traditional founder skills feel outdated.
...
Chris Wichert raised roughly $20M to build a modern luxury sneaker brand, pitching Koio as the “Louis Vuitton for millennials.” After business school, he moved to New York and secured investors, including the Winklevoss twins, Founders Fund, and the founder of Aldo, scaling through press, retail experiments, and premium positioning.
Then COVID hit. Retail revenue disappeared. Demand for dress sneakers collapsed. By early 2023, K...
From near bankruptcy… to a $700M strategic exit. Here’s how it actually happened.
Brian Ree built DailyLook into a premium AI-powered personal styling brand, nearly lost it in 2014, rebuilt it around ruthless unit economics and LTV, merged with Adore Me, and ultimately exited to Victoria’s Secret in a $700 million transaction.
In this episode, Brian breaks down the real story behind the pivot that almost killed the company, t...
From raising $100M from SoftBank to shifting from “growth at all costs” to building a durable business, Kris shares the real story behind scaling Sendoso to over $100M in revenue.
In this episode of $100M Exits, Kris walks through what it was actually like pitching Masayoshi Son over Zoom, deploying nine figures into aggressive hiring, then quickly pivoting when the zero-interest-rate era ended. He breaks down the hard decisions aro...
From building a booming business overseas to being forced to start over, this is the founder journey most people never talk about.
James Rose built and scaled an online furniture company during a massive property boom in Eastern Europe—only to see it nearly collapse during the global financial crisis. After years as an entrepreneur, he was forced to swallow his pride, re-enter the job market, and rebuild through sales and leadership...
Most founders fail for psychological reasons—not tactical ones.
In this episode of $100M Exits, Jason Kirby sits down with Aram Attar, founder of The VC Factory, to unpack the hidden psychology shaping fundraising outcomes, VC decisions, and why smart founders keep repeating the same mistakes.
With 15+ years advising founders, sitting on boards, and training venture capitalists, Aram shares a clear conclusion: most failures aren’...
From building a $100M software business to watching it fall apart—here’s what really happened.He built a software company from the ground up and scaled it past $100M in sales.
Matthew Whyatt started his first tech business at 22—and learned the hard way what happens when growth, partners, and focus drift off course.In this episode, Matthew breaks down the real story behind scaling fast, losing focus, and the lessons that reshaped ho...
From VC intern to $76M raised, here’s how it really happened.
He raised $76M in two years—without ever working in defense tech.
Nelson Mills, co-founder and CEO of a fast-growing underwater defense startup. Shares how he went from a VC intern to leading a company building autonomous undersea vehicles and why the maritime defense space became the perfect opportunity.
He breaks down how he validated the market, assembled a world-class ...
Andrew D’Souza, ex-co-founder of Clearco and now Boardy.ai, explains how he went from building a billion-dollar FinTech company to creating an AI “super-connector” that changes how founders meet investors.
Andrew breaks down why warm intros no longer work, how Boardy.ai sparked investor interest before he was even fundraising, and why real-time AI conversations may become the future of dealmaking.
He also shares ideas on founder psy...
After 20 years of steady, bootstrapped growth, Eric Friedman sold his company, eSkill, an online skills testing platform used by employers worldwide.
In this episode, Eric breaks down how he built a profitable SaaS business with no outside funding, ran three separate sales processes, and closed a deal with private equity in 2024. He shares what founders should know about earnouts, how to choose the right investment bank, and the red...
In this episode, we break down how founders and early employees can get liquidity before an IPO—without selling shares, triggering taxes, or relying on a shaky secondary market.
Our guest is Greg Brogger, founder of SharesPost (sold to Forge Global for $160M, later taken public and acquired) and now CEO of Collective Liquidity.Greg is one of the earliest architects of the private stock market, with over $10B+ in transactions.
He co...
What really happens when a founder crosses the table to become an investor?
In this episode, Andrew Ackerman, former Managing Director at DreamIt Ventures and author of The Entrepreneur’s Odyssey, joins Jason to discuss what he has learned backing more than 70 startups across ed-tech, prop-tech, and beyond.
Andrew shares how he went from writing angel checks that disappeared to running one of the top accelerators in the U.S. ...
He sold his Adtech company to Oracle after burning out, took it easy, then raised $100M+ for his next venture.
Most founders dream of a big exit but few talk about what happens after.
Subscribe & get our free investor/buyer list at thunder.vc.
Key Takeaways:The emotional and mental cost behind selling Crosswise to Oracle.How burnout nearly ended Ron’s startup journey—and what pulled him back.
The surprising truth about lif...
What do you do when your company is on fire, literally or figuratively?What do you do when the deal is days away from closing — and your company’s reputation explodes overnight?In this episode, David Meadvin, CEO of One Strategy Group, breaks down what really happens in the “war room” when crisis hits and how to protect your credibility, investors, and valuation when everything’s on fire.Subscribe & get our free investor/buyer ...
Most founders sell the wrong way. Here’s how to do it right.
📣 Subscribe & get our free investor/buyer list at https://web.thunder.vc/vc-investor-list
What you’ll learn in this episode:
Forget the unicorn dream. This is how real founders achieve life-changing exits. Jason Kirby and Oliver Low — partners at Thunder — break down how to navigate the M&A process from both sides of the table: when to sell, how to structure a d...
When Itamar Novick joined Life360, it wasn’t the family safety app we know today.
The team was small. The product was rough. The future? Uncertain.
Then came the moment that would define everything:
👉 The company was out of cash.
👉 Investors were skeptical.
👉 Itamar had a choice — walk away or double down.
He chose to bet his entire net worth on the company.
That all-in moment eventually led to one of the most unique IPO jou...
Europe’s next defense-tech giant is being built in London. Subscribe & get our free investor/buyer list at thunder.vc
How Max Buchan helped take CoinShares from $0 to $50M revenue to $1.5B IPO —without VC money.
The insider story behind founding Valarian, the UK’s answer to Palantir.
Raising $20M in seed funding to build dual-use infrastructure for governments and enterprises.
The shift from crypto to defense...
He sold for $500M—then started all over again. Get our free investor/buyer list at thunder.vc
Why Shay Levi left NoName Security after its $500M sale to Akamai
How he built Unframe AI and raised millions at a massive valuation
The mindset shift from cybersecurity to AI innovation
What founders get wrong about timing their exits
Lessons on capital efficiency and founder evolution after a big win
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