$100M Exits with Jason Kirby

Jason Kirby
  • 5.0 (6)
  • Entrepreneurship
  • Updated Weekly

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!

  1. EP 117: The VC System Is Broken: Global IPOs Are The Alternative with Jeff Stewart

    Jun 4

    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 outcomes The rise (and risks) of secondary markets and SPV structures Why transparency and liquidity drive better capital allocation How global investors are reshaping IPO strategy Why “unit economics clarity” is the real IPO readiness test The 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 STEWART Jeffrey 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 KIRBY Jason 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.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT $100M EXITS My 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.

    48 min
  2. EP 116: How M&A, Product Innovation, and Family Legacy Built a $100M Industrial Platform

    May 28

    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 KIRBY Jason 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.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT $100M EXITS My 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.

    54 min
  3. EP 115: How We 10X'd EBITDA in 7 Years

    May 21

    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 firm Why other PE firms avoided Opta—and why Speyside leaned in How operational improvements alone drove a 10X EBITDA increase Why free cash flow reveals what adjusted EBITDA hides What founders should know before choosing PE over a strategic buyer 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+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 KIRBY Jason 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.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT $100M EXITS My 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.

    47 min
  4. EP 114 | What Founders Get Wrong After Making Millions From an Exit

    Apr 30

    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 years Why culture fit matters more than price in an acquisition The biggest mistake founders make when cash hits their bank account Why trying to time the market can cost you millions The difference between being a great founder and a great investor Why many founders hesitate to spend on themselves—even after a big exit How to think about diversification beyond just stocks What most founders get wrong about managing wealth after liquidity 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+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+Exits Here's what you're in for: 00:00 Welcome and Guest Intro 00:40 Building iLab Bootstrapped 01:15 Running the Sale Process 02:12 Choosing Agilent and Deal Terms 04:24 Culture Fit and RSU Earnouts 08:03 Deal Lessons and Next Steps 10:22 Managing Money After Exit 13:29 Founder DIY vs Advisors 16:42 Biggest Post-Exit Mistakes 23:51 Why Long Angle Exists 27:10 Inside the Community Offerings 30:11 Diversification and Private Markets 39:33 Founder vs Employee Behaviors 43:45 Advice for Newly Liquid Founders 47:37 How to Join and Closing ABOUT 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 KIRBY Jason 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.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT $100M EXITS My 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.

    46 min
  5. EP 113: The Truth About “Free” Investor Money

    Apr 16

    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 capital How to think about investor money the right way Why every dollar should be treated like a loan The importance of staying lean early on How to hire smart and build efficiently How 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+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+113&utm_campaign=%24100M+Exits Here's what you're in for: 00:00 Guest Welcome 01:17 Spending With Payback Mindset 01:32 Staying Lean and Hiring Lessons 01:40 Equity and Efficiency Goals 02:01 Stay Lean as a Founder 02:30 Why They Sold and Exit Mindset 03:02 What Gato Built in PropTech 03:49 Listening to CRE Pain Points 04:32 Dashboards Tickets and Waste Data 06:16 M&A Sale Mistakes and Advisors 10:35 Founder Takeaways on Cash and Raises 12:03 Life After Acquisition and Earnout Reality 15:40 Post Exit Reset and New Chapter 16:01 Learning Food Tech Sales at Fuda 18:25 COVID Pivot and CloudKitchens Consulting 19:46 Joining NAO and Choosing Equity 22:39 Scaling NAO Starts With CAC 23:14 Fixing Ad Spend Targeting 24:03 Referral Engine That Closes 25:44 Cookie Outreach Playbook 29:47 From Cookies to Healthcare Pivot 34:18 Where Health Tech Is Going 38:33 Winners Losers and AI Risk 42:31 Consolidation and Startup Survival 45:46 Closing ABOUT 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 KIRBY Jason 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.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT $100M EXITS My 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.

    48 min
  6. EP 112: How He Built and Sold a $100M Startup Twice | Dan Rosenberg

    Apr 11

    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 cost Why choosing the right market matters The risks of scaling through big deals What actually happens during an acquisition Why many deals fall apart How the creator economy is shifting toward ownership 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+112&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+112&utm_campaign=%24100M+Exits Here's what you're in for: 00:00 Meet Daniel Rosenberg  00:49 Represent Origin Story 03:07 Landing Big Talent 05:26 Growth Engine Explained 07:49 Mayweather Cash Drop 10:06 Licensing With Major IP 11:01 Affiliate Versus Celebrity Focus 15:05 Custom Ink Acquisition 18:18 Deal Terms And Earnout 19:59 Diligence Distraction Lessons 21:40 Post Merger Integration 25:10 Selling To Cameo 29:37 Cameo Integration Reality Check 33:33 Why Dan Stepped Away 35:51 Ownership Shift In Creator Economy 38:20 Partnering With Creators 40:57 Risks And Who Should Worry 43:12 Resources And Closing ABOUT 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 KIRBY Jason 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.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT $100M EXITS My 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.

    47 min
  7. EP 111: How Defense Tech Startups Get Funded | AI, Warfare, and Venture Capital with Brad Harrison @ Scout Ventures | EP 111

    Apr 2

    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+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+111&utm_campaign=%24100M+Exits Here's what you're in for: 00:00 Entrepreneur Journey 01:55 Founder Support at Scout 03:46 Army Futures Command Shift 05:17 Ukraine Drone Autonomy Leap 08:12 Why US Procurement Lags 10:53 Key Defense Tech Domains 12:43 GPS Denied Navigation 15:17 Next Gen Wireless 6G 18:44 Founder Goals and Focus 20:43 Red Flags and Hard Calls 23:57 What Gets Funded Now 28:19 Vendor Lock Risks 29:11 AI Security Threats 30:31 Autonomy Changes Warfare 31:50 Selling to the Pentagon 32:27 RFPs, TRLs, and SBIRs 35:48 Lobbying and Budgets 38:28 Founder Insight Advantage 41:16 Tomahawk Robotics Exit 44:32 Defense Tech M&A Drivers 49:39 Scout Fund Strategy 51:53 Space Deterrence Vision 56:32 Founder Upside and Wrap ABOUT 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 KIRBY Jason 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.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT $100M EXITS My 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.

    53 min
  8. EP 110: From Operator to Investor: George Alifragis on Scaling With Non-Dilutive Capital

    Mar 27

    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 investor How George scaled a global tech company and drove EBITDA growth What makes a business attractive to private equity buyers The key differences between big corporations and mid-sized companies Why growth operators thrive in different environments How investors actually evaluate risk and opportunity Lessons from exiting companies to TELUS and a PE-backed firm Why understanding the capital strategy is critical for a founder 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+110&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+110&utm_campaign=%24100M+Exits Here's what you're in for: 00:00 Welcome and George Alifragis Intro 00:57 Operator Exits and Track Record 02:32 From Bell to Building Altima Telecom 07:24 Why He Left Corporate Life 10:43 Regulation That Forced an Exit 13:56 Moving to Miami and a New Chapter 15:17 Scaling to a Successful Exit 16:53 From Operator to Investor 21:43 Inside Metropolitan’s Investment Thesis 25:14 The Power of an Operator Network 27:01 The Operating Experts Model Explained 27:52 The Fishing Holes Investment Strategy 28:47 Building an Ecosystem Partner Network 30:12 Activating the Network at Scale 32:21 The Deal Flow Flywheel 34:30 How Deals Get Done at Metropolitan 37:45 Alternative Capital Explained 39:22 Structuring Bespoke Hybrid Deals 45:07 A Real Deal Structure Breakdown 50:25 Lessons on Cost of Capital 53:53 Final Thoughts and How to Connect ABOUT 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 KIRBY Jason 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.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT $100M EXITS My 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.

    55 min
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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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