Shows / $100M Exits with Jason Kirby
$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…
Episodes
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP122: 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEp 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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 Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 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…
$100M Exits with Jason KirbyEP 97: From Startup Burnout to $100M Raise: Ron Reiter’s Redemption
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…
$100M Exits with Jason KirbyEP 96: Inside the War Room: How to Manage a Company Crisis w/ David Meadvin
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…
$100M Exits with Jason KirbyEP 95: How to Sell Your Startup: The Founder’s M&A Playbook
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…
$100M Exits with Jason KirbyEP 94: I Bet My Entire Net Worth on Life360 — It Paid $8B Later
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…
$100M Exits with Jason KirbyEP 93: Building Europe’s Palantir: How Max Buchan Raised $20M to Launch Valarian
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…
$100M Exits with Jason KirbyEP 92: Why I Left My $500M Startup to Start Again — Shay Levi (Unframe AI)
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…
$100M Exits with Jason KirbyEP 91: How She Bought Back Her Company From Investors
Melinda Nicca shares her story of raising capital, building a cash flow machine and buying it back from her investors to give herself independence again. In…
$100M Exits with Jason KirbyEP 90: Search Funds Demystified: How Jon Staenberg (Agate Hound Fund) Nets 35% Annual Returns
This week, I chat with Jon Staenberg founding partner of Agate Hound Fund, to unpack the real mechanics behind venture capital and search funds. From his early…
$100M Exits with Jason KirbyEP 89: From Uber to Snap to AI: Ben Chiang on Raising Millions Then vs Now
In this episode of Fundraising Demystified, I sit down with Ben Chiang, the former head of Uber China and founder of Forma (acquired by Snap- yes, from…
$100M Exits with Jason KirbyEP 88: How a Broken Leave Policy Led to a $30M HR Tech Startup w/ Jenniffer Henderson (Tilt)
60 pitches in 90 days. A Series B term sheet that collapsed. A $15M valuation hit, and she still came out on top. In this episode, Jennifer Henderson, founder…
$100M Exits with Jason KirbyEP 87: Customer Retention Over Acquisition? Travis Steffen, Who’s Done $200M in Deals, Says Yes
This week, I talk to Travis Steffen, who has built and sold eight companies. He’s raised over $100M and driven more than $200M in exits. In this episode, we…
$100M Exits with Jason KirbyEP 86: What Founders Get Wrong About Exits (and How John Rood Got It Right)
Most founders dream of a life-changing exit. But few actually prepare for it, until it’s too late. In this episode of Fundraising Demystified, I sit down with…
$100M Exits with Jason KirbyEP 85: From Burnout to Breakout: How Jennifer Tsai Bootstrapped Shoott.com to $10M After Raising $2.7M
What happens when you raise $2.7M... then realize you never want to raise again? Jennifer Tsai, founder and CEO of Shoott.com, built a profitable photography…
$100M Exits with Jason KirbyEP 84: David Connors Used The Swarm to Raise Millions | Deal Flow, M&A, and Warm Intros
This week on Fundraising Demystified, I sat down with David Connors, founder of The Swarm, a Go-To-Network platform transforming how founders and investors…
$100M Exits with Jason KirbyEP 83: Jess Loren on Digital Twins & Unconventional Strategies of Raising Capital as Female Founder
In this episode, Jess Loren, founder and CEO of Global Objects, shares her journey on raising capital as a female founder, including turning down a $20M offer…
$100M Exits with Jason KirbyEP 82: How to Build a Startup Advisors | Barry Stamos of Supernova on Scaling & Managing Advisors
Startup Advisors can make or break your growth. In this episode, Barry Stamos of Supernova shares how to build a world-class startup advisory board, manage…
$100M Exits with Jason KirbyEP 81: IPO Market Trends 2025: Best Time to Go Public w/ Peter Goldstein | IPO Valuation & Readiness
This week, I host IPO market expert Peter Goldstein, who talks about the best time to IPO, how to position for strong IPO performance, what true IPO readiness…
$100M Exits with Jason KirbyEP 80: JC Glancy’s Unicorn Startup ZenBusiness From Credit Card Debt, Gave Up CEO, Hit $1B Valuation
JC Glancy, co-founder of ZenBusiness, shares his remarkable unicorn startup journey, from nearly drowning in credit card debt to building a billion-dollar…
$100M Exits with Jason KirbyEP 79: How to Attract Influencers to Promote Your Startup: Celebrity Marketing & Influencer Deals Explained
In this episode, Gil Eyal of Stardust Ventures shares expert insights on celebrity marketing and influencer deals for startups. Learn how to pitch your startup…
$100M Exits with Jason KirbyEP 78: How to Make a Startup Successful, Founder Mindset & Startup Operations with Adam Spector of Chore
In this episode, I sit down with Adam Spector, CEO of Chore, to break down founder mindset, startup operations, and how to make a startup successful. Adam…
$100M Exits with Jason KirbyEP 77: How To Spot Massive Early-Stage Startup Trends With Katelyn Donnelly Of Avalanche VC
How do you identify and capitalize on the biggest upcoming trends? Katelyn Donnelly, GP of Avalanche Ventures, unveils her unique investment strategy focusing…
$100M Exits with Jason KirbyEP 76: What VC Look For in Early Stage Startups with Dave Lambert Right Side Capital Management
Wondering what VCs look for in early-stage startups? In this episode, Dave Lambert, Managing Partner at Right Side Capital Management, shares insights on how…
$100M Exits with Jason KirbyEP 75: Raising Capital & Selling a Startup for Millions – Jeremy Parker’s Swag.com Story
Jeremy Parker, co-founder of Swag.com discusses his incredible journey of building a successful swag business from scratch and ultimately selling it to Custom…
$100M Exits with Jason KirbyEP 74: Jon Tucker of HelpFlow on AI for business efficiency and Evaluating AI Performance
AI for Business Efficiency is reshaping how companies operate, and in this episode, Jon Tucker, founder of HelpFlow, shares how AI is transforming customer…
$100M Exits with Jason KirbyEP 73: Fundraising Quadrants Explained: Where Does Your Startup Fit?
Not all startups should chase VC money. Some should bootstrap, others should take on debt, and a few are primed for private equity. So how do you know which…
$100M Exits with Jason KirbyEP 72: Bootstrapping, Exiting, and Alternative Fundraising with Laurits Just
Would you rather grind for years bootstrapping, take VC money with strings attached, or sell and move on? That’s the exact crossroads Laurits Just faced as the…
$100M Exits with Jason KirbyEP 71: How Rebel Energy Scaled £1.5M to £100M with Penelope Hope
Penelope Hope, founder of Rebel Energy, shares her journey of building a renewable energy company from scratch with just £1.5 million raised, scaling it to…
$100M Exits with Jason KirbyEP 70: From Founder to Philanthropist: $1.3B Deployed by David Goldberg
After achieving financial success as a founder, David Goldberg shifted his focus to making a global impact. As the founder of Founders Pledge, David has…
$100M Exits with Jason KirbyEP 69: Scaling and Selling to Eight-Figure Exits with Carrie Kerpen
From founding one of the earliest social media agencies to crafting an intentional path to a major eight-figure exit, Carrie Kerpen has redefined what it means…
$100M Exits with Jason KirbyEP 68: From Bootstrapping to an Eight-Figure Exit with Conor Tomkies
From dog genetics to bootstrapping to an eight-figure exit , Conor Tomkies has done it all. As the founder of Support Ninja, Conor scaled a bootstrapped…
$100M Exits with Jason KirbyEP 67: From Bootstrapping to $175M Exits with David Hauser
Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders Get the latest fundraising insights, news…
$100M Exits with Jason KirbyEP 66: How Patrick Butler Built 3 Wildly Different Businesses
Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders Get the latest fundraising insights, news…
$100M Exits with Jason KirbyEP 65: Navigating Debt Financing for Startups with Kyle Rector of Boundless
Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders Get the latest fundraising insights, news…