$100M Exits with Jason Kirby
By Jason Kirby
Categories: Business, Entrepreneurship
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!
126 episodes indexed on podsearch.
Recent episodes
- EP 124: He Sold AI to Microsoft Before ChatGPT. Now He's Building an AI CEO
Yahoo walked away three weeks before the press release. Then Microsoft bought Sam Pasupalak's AI startup for $160M. Sam tells Jason how he ran a $50M raise alongside Microsoft's offer, and why he's now building an AI CEO at Skyfall AI. If this episode helps, follow $100M Exits and rate the show…
- EP 123: How a Family Office Invests in Defense Tech and Space Startups
In this episode of $100M Exits, Jason sits down with Richard Stroupe, founder of Cape Fear Ventures and exited founder who sold two companies for over $50M, to pull back the curtain on how a family office actually deploys capital — and what most founders get completely wrong when pitching…
- EP122: How VCs Spot Billion-Dollar Startups Before Everyone Else
In this episode of $100M Exits, Jason sits down with Dan Nguyen-Huu, Partner at Decibel Ventures, to unpack what early-stage specialist investing really looks like, from getting into Databricks at a $950M valuation to seeding Sublime Security before it raised a $150M Series C.Dan breaks down how…
- EP 121: Where Founders Should Actually Bet with Itamar Novick
In this episode of $100M Exits, Jason sits down with Itamar Novick, Founder and General Partner of Recursive Ventures, to unpack where the real value in AI will be created, why today’s AI infrastructure market looks increasingly like a bubble, and what founders need to build companies that can…
- EP 120: The Agency Rollup Playbook: 24 Acquisitions, $750M Revenue, and What Most Buyers Get Wrong
In this episode of $100M Exits, Jason sits down with Erik Huberman, Founder and CEO of Hawke Media, to unpack what it really takes to run a programmatic M&A strategy, back early-stage founders, and scale a media agency to $750M in gross revenue, all at the same time. Erik has done 24 acquisitions…
- EP 119: From Family Liquor Empire to $300M Fund
In this episode of $100M Exits, Jason sits down with Brian Rosen of InvestBev Capital to unpack what it really takes to sell a family business, build from scratch, and then deploy $300M backing the founders most investors overlook. Brian has lived every side of the deal table — operator, seller…
- Ep 118: The AI Divide Is Here: Why Most Companies Will Fall Behind
In this episode of $100M Exits, Jason sits down with Jim Ferry of Volition Capital to unpack what’s really happening inside growth equity, AI-driven dealmaking, and today’s frozen liquidity market.Managing over $1.8B in growth equity, Jim explains how the market has shifted from easy capital and…
- EP 117: The VC System Is Broken: Global IPOs Are The Alternative with Jeff Stewart
In this episode of $100M Exits, Jeff Stewart breaks down why the venture capital and IPO system has fundamentally shifted—and what founders are getting wrong about scale, liquidity, and global capital markets.Jeff shares his experience raising and transacting over $100M across his own companies…
- EP 116: How M&A, Product Innovation, and Family Legacy Built a $100M Industrial Platform
Drew Allen didn’t start Grace Technologies — he inherited it.But stepping into a family business isn’t just a continuation. It’s pressure: legacy, expectations, and the challenge of evolving something that already works without breaking it.In this episode, Drew shares what it’s really like taking…
- EP 115: How We 10X'd EBITDA in 7 Years
From buying a messy manufacturing business with 26 plants to building a $100M EBITDA powerhouse, here's how it really happened.For two decades, Eric Wiklendt has bought manufacturing businesses most PE firms avoid—and turned them into massively more valuable companies. Eric Wicklendt, Partner and…
- EP 114 | What Founders Get Wrong After Making Millions From an Exit
He built a company, sold it, and suddenly had millions in the bank. Here’s what no one tells you about what comes next. He bootstrapped a health tech SaaS company for 10 years and sold it to Agilent Technologies.Sriram Gollapalli went from grinding as a founder to managing millions overnight—and…
- EP 113: The Truth About “Free” Investor Money
Most founders waste money right after raising it.Dipak Patel breaks down one of the biggest mistakes founders make after raising capital—hiring too fast and burning cash. Instead, the focus should be on using that money wisely and creating real value.His mindset is simple: treat every dollar like…
- EP 112: How He Built and Sold a $100M Startup Twice | Dan Rosenberg
He built a $100M creator platform—and sold it twice. Here’s what actually happens after the deal closes.Daniel Rosenberg, cofounder of Represent.com, shares how he helped creators and celebrities sell products without upfront cost using on-demand production. This removed the biggest barrier for…
- EP 111: How Defense Tech Startups Get Funded | AI, Warfare, and Venture Capital with Brad Harrison @ Scout Ventures | EP 111
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…
- EP 110: From Operator to Investor: George Alifragis on Scaling With Non-Dilutive Capital
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…
- EP 109: Why Silicon Valley Founders Are Panicking About AI w/ Jessica Mah
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…
- EP 108: Luxury DTC Founder Chris Wichert: Raising $20M, Surviving DTC Collapse & Turnaround Exit
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…
- EP 107: He Pivoted to Survive—Then Sold to Victoria's Secret for ~$700M | Brian Ree
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…
- EP 106: How Sendoso Raised $100M From SoftBank w/ Kris Rudeegraap
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…
- EP 105: From CEO to Employee: The Hardest Pivot of a Founder’s Career
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…
- EP 104: The Psychology Driving Fundraising, VC Decisions, and Founder Failure w/ Aram Attar
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…
- EP 103: Built a $100M Software Business at 22 | Matthew Wyatt, Founder of TechTorque
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…
- EP 102: He Raised $76M With No Defense Tech Background | Nelson Mills Founder of VATN Systems
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…
- EP 101: Unicorn Founder Raises $8M Using AI (Andrew D’Souza, Clearco & Bordy.ai)
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…
- EP 100: The Earnout Trap: What This Founder Learned After Selling His Company
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…
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