$100M Exits with Jason Kirby

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119

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Jun 2026

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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!

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June 4, 2026Episode 11747 min

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, investing over $100M through his fund, and leading more than $500M in total deal flow. The conversation dives deep into why the U.S. public markets have evolved into a “mega-cap only” game, why secondary markets create hidden risks, and why global listings are becoming a strategic advantage—not an alternative.The discussion also unpacks how founders should think about IPOs not as exits, but as long-term capital infrastructure. Jeff explains how public markets unlock talent, revenue, acquisition flexibility, and investor access in ways private markets increasingly cannot match.Key insights include:Why the VC model incentivizes longer private cycles—but not always founder outcomesThe rise (and risks) of secondary markets and SPV structuresWhy transparency and liquidity drive better capital allocationHow global investors are reshaping IPO strategyWhy “unit economics clarity” is the real IPO readiness testThe difference between a “funding event” and a “capital system.”This is a sharp, sometimes contrarian look at where capital markets are heading—and how founders can position themselves to win in a global IPO landscape.-------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=EP+117&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=EP+117&utm_campaign=%24100M+Exits ABOUT JEFFREY STEWARTJeffrey Stewart is an inventor, entrepreneur, investor, and author focused on technology-enabled businesses and global capital markets. He is the author of Global IPO – The Great Rewiring of Capital Markets and works with GPO Fund, where he backs growth-stage tech founders building globally scalable companies.Through the GPO Fund, Jeffrey invests in companies across emerging markets, B2B SaaS, clean-tech, education, blockchain, big data, and financial services, with a focus on improving how venture capital and global capital markets operate.You can reach out to Jeff through:LinkedIn:https://www.linkedin.com/in/stewartjeffrey Website: https://www.youtube.com ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+.You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.

May 28, 2026Episode 11654 min

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 over as CEO of a family-founded industrial tech company, and the mindset shift required when preservation meets reinvention.From international experience in Hong Kong to leading a U.S. Midwest manufacturing and safety tech business, he breaks down how Grace Technologies evolved from a traditional engineering firm into a full-stack industrial innovation platform.At the core of it all is a bigger question: How do you make a “boring business” not boring, and why does that transformation matter more than it seems?Why It Matters:This isn’t just a family business story; it’s about turning inherited structure into a system that can innovate.Drew shows that scale isn’t only driven by capital or speed, but by control of technology, clarity of vision, and building systems that evolve faster than the market.In industrial sectors — safety, manufacturing, infrastructure — most people overlook that adaptability can be the difference between downtime and danger.----------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=EP+116&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=EP+116&utm_campaign=%24100M+Exits ABOUT DREW ALLEN Drew Allen is the CEO of Grace Technologies, where he leads the development and global distribution of innovative industrial technologies. A recipient of the National Association of Manufacturers’ 2020 Next-Generation Leadership Award, Drew has built his career around business development, international sales, product innovation, and family business leadership.Beyond Grace Technologies, Drew also serves as CEO of Percev, LLC and sits on the advisory board of Atom Power, bringing a strong passion for technology, product design, and scaling impactful businesses worldwide.You can reach out to Drew through:LinkedIn: https://www.linkedin.com/in/allendrew Website: https://www.graceport.com ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.

May 21, 2026Episode 11546 min

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 Managing Director at Speyside Equity, has built a career around acquiring underloved, underperforming manufacturing businesses and transforming them into platforms worth exponentially more than what they paid.In this episode, Eric breaks down the real story behind Speyside's origin, their signature "fix and build" strategy, and the Opta deal that became a masterclass in manufacturing transformation. He shares why most PE firms rely on hope as a strategy, how free cash flow tells the truth EBITDA can hide, and what it actually takes to turn around a business with 26 manufacturing plants in 18 months.If you're a founder, operator, or investor in the manufacturing space, this episode is packed with hard-earned, battle-tested insight.What you'll learn in this episode:How Speyside turned a $300K 401(k) bet into a manufacturing PE firmWhy other PE firms avoided Opta—and why Speyside leaned inHow operational improvements alone drove a 10X EBITDA increaseWhy free cash flow reveals what adjusted EBITDA hidesWhat founders should know before choosing PE over a strategic buyerRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=EP+115&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=EP+115&utm_campaign=%24100M+Exits ABOUT ERIC WIKLENDT Eric Wiklendt is a Managing Director and Partner at Speyside Equity, where he leads the sourcing, execution, management, and exit of investments while serving on the boards of several portfolio companies. Before joining Speyside, he held senior operational and leadership roles, including President & CEO of Kelix Heat Transfer Systems, as well as leadership positions at Eaton and Hilti Corporation, overseeing M&A, manufacturing, marketing, and industrial sales operations. You can reach out to Eric through:LinkedIn:https://www.linkedin.com/in/ericwiklendt Website: https://speysideequity.com/ Email: eric.wiklendt@speysideequity.com ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.

April 30, 2026Episode 11345 min

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 realized that making money and managing money are two completely different games.In this episode, he breaks down what founders don’t expect after an exit: the pressure of sudden wealth, the trap of overthinking investments, and why so many founders freeze when cash is just sitting in the bank. He shares how choosing the right buyer goes beyond valuation, why culture fit matters more than most realize, and the biggest mistakes he sees founders make when trying to invest in their exit.If you’re a founder building toward an exit—or already have one—this is the side of the journey no one prepares you for.What you’ll learn in this episode:How Sriram bootstrapped and exited his company after 10 yearsWhy culture fit matters more than price in an acquisitionThe biggest mistake founders make when cash hits their bank accountWhy trying to time the market can cost you millionsThe difference between being a great founder and a great investorWhy many founders hesitate to spend on themselves—even after a big exitHow to think about diversification beyond just stocksWhat most founders get wrong about managing wealth after liquidityRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=EP+114&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+114&utm_campaign=%24100M+ExitsHere's what you're in for: 00:00 Welcome and Guest Intro00:40 Building iLab Bootstrapped01:15 Running the Sale Process02:12 Choosing Agilent and Deal Terms04:24 Culture Fit and RSU Earnouts08:03 Deal Lessons and Next Steps10:22 Managing Money After Exit13:29 Founder DIY vs Advisors16:42 Biggest Post-Exit Mistakes23:51 Why Long Angle Exists27:10 Inside the Community Offerings30:11 Diversification and Private Markets39:33 Founder vs Employee Behaviors43:45 Advice for Newly Liquid Founders47:37 How to Join and ClosingABOUT SRIRAM GOLLAPALLI Sriram Gollapalli is a former tech founder and investor. He co-founded iLab Solutions, a health tech SaaS company he bootstrapped for over a decade before selling to Agilent Technologies. After his exit, he shifted his focus to investing and is now the co-founder of Long Angle, a private community for high-net-worth individuals focused on wealth, investing, and life after liquidity. You can reach out to Sriram through:LinkedIn: https://www.linkedin.com/in/sriramg/Email: sriram@longangle.com ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.

April 16, 2026Episode 11348 min

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 a loan. Even if it feels like free money, it comes with expectations. The best founders stay lean, hire carefully, and focus on efficiency before scaling.Rather than rushing into expensive senior hires, Dipak shares why it’s better to bring in the right people, give them ownership, and let them help build smarter systems first.If you’re raising money or planning to, this episode is a powerful reminder that discipline,not spending,is what drives long-term success.What you’ll learn in this episode:Why most founders waste money after raising capitalHow to think about investor money the right wayWhy every dollar should be treated like a loanThe importance of staying lean early onHow to hire smart and build efficientlyHow to avoid burning cash too fast Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+113&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+113&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Guest Welcome01:17 Spending With Payback Mindset01:32 Staying Lean and Hiring Lessons01:40 Equity and Efficiency Goals02:01 Stay Lean as a Founder02:30 Why They Sold and Exit Mindset03:02 What Gato Built in PropTech03:49 Listening to CRE Pain Points04:32 Dashboards Tickets and Waste Data06:16 M&A Sale Mistakes and Advisors10:35 Founder Takeaways on Cash and Raises12:03 Life After Acquisition and Earnout Reality15:40 Post Exit Reset and New Chapter16:01 Learning Food Tech Sales at Fuda18:25 COVID Pivot and CloudKitchens Consulting19:46 Joining NAO and Choosing Equity22:39 Scaling NAO Starts With CAC23:14 Fixing Ad Spend Targeting24:03 Referral Engine That Closes25:44 Cookie Outreach Playbook29:47 From Cookies to Healthcare Pivot34:18 Where Health Tech Is Going38:33 Winners Losers and AI Risk42:31 Consolidation and Startup Survival45:46 ClosingABOUT DIPAK PATEL Dipak Patel is an LCRO and operator, and a SaaS revenue expert. He is a 2x exited founder and has helped drive over $232M+ in ARR across the companies he’s worked with.He specializes in building go-to-market strategies for VC and private equity-backed companies, helping them grow efficiently and scale revenue. Dipak is also an advisor and investor, known for his focus on capital discipline and smart growth.You can reach out to Dipak through:LinkedIn: https://www.linkedin.com/in/dipakrpatel/ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.

April 11, 2026Episode 11046 min

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 creators: launching a business without upfront cost or inventory risk.In this episode, he explains how Represent grew by working with top talent, why they focused on fewer, higher-value creators, and the risks that came with scaling fast. He also breaks down what really happens when you sell a company—from long deal processes to post-acquisition challenges.Daniel also shares how the creator economy is changing. Today, creators don’t just want sponsorships—they want ownership and equity.What you’ll learn in this episode:If you’re building a startup or thinking about exits, this episode gives you real, practical insights.How creators sell products without upfront costWhy choosing the right market mattersThe risks of scaling through big dealsWhat actually happens during an acquisitionWhy many deals fall apartHow the creator economy is shifting toward ownershipRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+112&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+112&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Meet Daniel Rosenberg 00:49 Represent Origin Story03:07 Landing Big Talent05:26 Growth Engine Explained07:49 Mayweather Cash Drop10:06 Licensing With Major IP11:01 Affiliate Versus Celebrity Focus15:05 Custom Ink Acquisition18:18 Deal Terms And Earnout19:59 Diligence Distraction Lessons21:40 Post Merger Integration25:10 Selling To Cameo29:37 Cameo Integration Reality Check33:33 Why Dan Stepped Away35:51 Ownership Shift In Creator Economy38:20 Partnering With Creators40:57 Risks And Who Should Worry43:12 Resources And ClosingABOUT DANIEL ROSENBERG Daniel “Dan” Rosenberg is a founder and entrepreneur best known for building Represent.com, a platform that helped creators and celebrities sell merchandise without upfront cost.He scaled the company to a $100M+ exit, selling it to Custom Ink, and later helped lead another sale to Cameo.Today, he focuses on the creator economy through Material Group, where he works with creators to build businesses where they have ownership—not just sponsorship deals.You can reach out to Daniel through:LinkedIn: https://www.linkedin.com/in/danielrosenberg1/ Website: https://www.materialgroup.co/ ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too much cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.

April 2, 2026Episode 11153 min

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 most expect.He explains how AI, drones, and autonomous systems are reshaping warfare, and why success requires more than a strong product—founders need the right networks, industry insight, and an understanding of government buyers.The conversation also covers how deals work in defense tech, what investors look for, and why choosing the right capital matters—especially when navigating government contracts.If you’re a founder, investor, or operator in AI, defense, or emerging tech, this episode offers a clear view on how to build and fund in this space.What you’ll learn:How operator experience shapes investment decisionsWhy defense tech innovation is acceleratingHow AI and autonomous systems are changing warfareWhy startups struggle with defense procurementWhat gets funded in defense tech todayHow to align with real government demandWhy networks and relationships matterWhat drives successful outcomes and exitsWhy understanding the end buyer is criticalHow capital strategy impacts growthRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+111&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+111&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Entrepreneur Journey01:55 Founder Support at Scout03:46 Army Futures Command Shift05:17 Ukraine Drone Autonomy Leap08:12 Why US Procurement Lags10:53 Key Defense Tech Domains12:43 GPS Denied Navigation15:17 Next Gen Wireless 6G18:44 Founder Goals and Focus20:43 Red Flags and Hard Calls23:57 What Gets Funded Now28:19 Vendor Lock Risks29:11 AI Security Threats30:31 Autonomy Changes Warfare31:50 Selling to the Pentagon32:27 RFPs, TRLs, and SBIRs35:48 Lobbying and Budgets38:28 Founder Insight Advantage41:16 Tomahawk Robotics Exit44:32 Defense Tech M&A Drivers49:39 Scout Fund Strategy51:53 Space Deterrence Vision56:32 Founder Upside and WrapABOUT BRAD HARRISON Brad Harrison is the Founder and Managing Partner of Scout Ventures, backing companies like ID.me, Voyager Space, and Tomahawk Robotics.A former U.S. Army Airborne Ranger and West Point graduate, he later studied at MIT Sloan, focusing on building new ventures.He has advised leaders at the White House and Pentagon on defense and innovation, and is now based in Austin, Texas.You can reach out to Brad through:LinkedIn:⁠ https://www.linkedin.com/in/bradharrison ⁠Website: ⁠https://www.scout.vc/⁠ ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.

March 27, 2026Episode 10854 min

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 company, and how that shapes how he evaluates businesses today.He shares what really drives EBITDA growth, what makes a company attractive to private equity, and why operators often misunderstand how investors think about risk, growth, and returns.If you’re a founder thinking about exits or capital, this is a clear inside look.What you’ll learn in this episode:What changes when you go from operator to investorHow George scaled a global tech company and drove EBITDA growthWhat makes a business attractive to private equity buyersThe key differences between big corporations and mid-sized companiesWhy growth operators thrive in different environmentsHow investors actually evaluate risk and opportunityLessons from exiting companies to TELUS and a PE-backed firmWhy understanding the capital strategy is critical for a founderRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+110&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+110&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Welcome and George Alifragis Intro00:57 Operator Exits and Track Record02:32 From Bell to Building Altima Telecom07:24 Why He Left Corporate Life10:43 Regulation That Forced an Exit13:56 Moving to Miami and a New Chapter15:17 Scaling to a Successful Exit16:53 From Operator to Investor21:43 Inside Metropolitan’s Investment Thesis25:14 The Power of an Operator Network27:01 The Operating Experts Model Explained27:52 The Fishing Holes Investment Strategy28:47 Building an Ecosystem Partner Network30:12 Activating the Network at Scale32:21 The Deal Flow Flywheel34:30 How Deals Get Done at Metropolitan37:45 Alternative Capital Explained39:22 Structuring Bespoke Hybrid Deals45:07 A Real Deal Structure Breakdown50:25 Lessons on Cost of Capital53:53 Final Thoughts and How to ConnectABOUT GEORGE ALIFRAGIS George Alifragis is a multi-time operator turned investor, currently at Metropolitan, a $1.8B private credit firm, bringing experience from scaling companies, driving EBITDA growth, and evaluating businesses through an investor lens.He previously served as CEO of a global tech company, leading growth and exiting to a private equity-backed firm, and was earlier part of a successful exit to TELUS, one of Canada’s largest telecom companies.You can reach out to George through:LinkedIn: ⁠https://www.linkedin.com/in/galifragis/⁠ ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.

March 19, 2026Episode 10959 min

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 playbooks. AI is compressing execution timelines, raising the bar for traction, and making many traditional founder skills feel outdated.Jess breaks down why relevance, speed, and adaptability now matter more than funding or past wins—and why many experienced founders are struggling to adjust. She also shares how to build lean, AI-first companies, protect your edge, use relationships as market intelligence, and why micro-teams may outperform bloated organizations.If you’re a founder navigating AI disruption, fundraising pressure, and shifting rules of company building, this conversation is a sharp reality check.What you’ll learn in this episode:• How AI is creating pressure even among unicorn founders• Why relevance and speed now matter more than money or status• What founders must unlearn to stay competitive• Why lean teams and micro-teams can outperform larger organizations• How to use side projects to rebuild your AI instincts and leadership edge• Why protecting your information edge matters more than everRaising capital?Get a list of vetted VCs for FREE here:https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+109&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+109&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Meet Jess Mah01:21 Silicon Valley Stress04:03 Money Versus Relevance06:12 AI is changing the game11:06 Founders React Poorly14:17 Lean Teams And Traction16:37 Funding Bar Keeps Rising19:33 Differentiation And Wedges22:15 Bias In Venture Funding28:43 AI As Equalizer31:30 Multi-Project Mindset33:56 Building Quietly In Public38:17 Networking As Market Radar42:19 Protecting Your Information Edge50:07 Side Hustles For Legacy Founders56:40 Micro Teams And Reorg Reality59:22 Leadership Reset And FarewellABOUT JESS MAHJessica Ma is a serial entrepreneur, investor, and venture builder known for launching and scaling multiple technology companies in Silicon Valley. She founded her first startup while still in college and scaled it to a nine-figure valuation after Y Combinator. Since then, she has founded and incubated more than 10 companies with combined valuations exceeding $1 billion. Today, she focuses on AI-driven ventures and shares insights on how AI is reshaping company building.You can reach out to Jess through:LinkedIn: https://www.linkedin.com/in/jessicamah/Website: https://www.mahway.com/ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A.He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+.You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it.For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast.Be sure to subscribe and let me know who you want me to interview next.

March 5, 2026Episode 1081 hr 1 min

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 experiments, and premium positioning.Then COVID hit. Retail revenue disappeared. Demand for dress sneakers collapsed. By early 2023, Koio faced roughly -$3M EBITDA in a market where DTC multiples had compressed and fundraising slowed dramatically.In this episode, Chris shares how they reset the business: cutting 40% of SKUs, reducing headcount by 70%, going remote-first, closing most stores, and removing $3M in costs without sacrificing revenue, returning the company to profitability.He also breaks down their exit process: running 200+ buyer conversations, navigating last-minute tariff-related deal risk, and ultimately selling to a Miami family office.If you’re a founder navigating scale, crisis, or exit timing, this episode offers a candid look at capital strategy, cost discipline, and realistic decision-making.What you’ll learn:Why early fundraising is about vision, not just numbersHow retail experiments validated a luxury DTC brandWhat happens when DTC multiples collapseHow to cut millions in costs without shrinking revenueWhy founders delay tough restructuring decisionsHow to run a disciplined, proactive M&A processRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+108&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+108&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Meet Koio Founder00:59 Why Raise Early Capital04:43 Retail Growth Playbook08:55 COVID Shock and DTC Reset15:51 Turnaround and Investor Realignment29:19 Choosing a Full Sale30:24 Building the Buyer Universe33:26 Tariffs Shake the Deal39:43 Founder Realism Shift52:43 Capital Traps and Exit AdviceABOUT CHRIS WICHERTChris Wichert is an entrepreneur and operator best known as the founder of Koio, a digitally native luxury sneaker brand built on craftsmanship and modern positioning. After raising ~$20M in venture capital, he scaled the business through retail expansion and premium brand building before navigating COVID and the broader DTC market collapse. Facing compressed multiples and a shifting capital environment, Chris led a full operational reset — cutting costs, restructuring the team, and restoring profitability — before successfully exiting to a family office. He now speaks and advises on capital strategy, turnaround execution, and proactive exit planning.You can reach out to Chris through:LinkedIn: https://www.linkedin.com/in/chris-wichert1/Website: https://ccatalyst.co/ABOUT JASON KIRBYJason Kirby is co-founder of Thunder, a tech-enabled investment bank helping founders reach ideal outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building, having coached hundreds of entrepreneurs and transacted over $135M personally; Thunder has transacted over $200M+.You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: equip founders with knowledge, inspiration, and guidance to navigate capital strategy by interviewing founders and investors who’ve done it. For most, a $100M+ exit is a dream; for others, cash flow or IPO matters. Founders doing over $5M in revenue benefit the most from this podcast.Be sure to subscribe and let me know who you want me to interview next.