$100M Exits with Jason Kirby

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 inflated SaaS multiples to a brutal divide between the “haves and have-nots.” He breaks down why inves...

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, investing over $100M through his fund, and leading more than $500M in total deal flow. The conversatio...

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 over as CEO of a family-founded industrial tech company, and the mindset shift required when preserv...

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 Managing Director at Speyside Equity, has built a career around acquiring underloved, underperfor...

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 realized that making money and managing money are two completely different games. In this episode, he...

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 a loan. Even if it feels like free money, it comes with expectations. The best founders stay lean, h...

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 creators: launching a business without upfront cost or inventory risk. In this episode, he explains how...

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...

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 gro...

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 f...

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 snea...

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...

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....

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...

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 clea...

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 f...

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...

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...

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...

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, wi...

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...

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....

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. Subscr...

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 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...