$100M Exits with Jason Kirby
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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…
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…
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…
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…
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…
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…
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…
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…
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…
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,…
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…
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…
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…
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…
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…
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…
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…
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…
EP 99: From Zero to $10B in Secondaries: Greg Brogger 's Journey to a $160M Exit
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…
EP 98: How Andrew Ackerman Scaled DreamIt Ventures & Made 70+ Startup Bets
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,…
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$100M Exits with Jason Kirby has published 119 episodes since June 2023, covering topics in Business, Entrepreneurship.
$100M Exits with Jason Kirby is currently highly active with new episodes weekly. Average episode length is 46m.
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