$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 ton of value & insights you can apply to your fundraising journey. Don't forget to hit subscribe!

$100M Exits with Jason Kirby is a business podcast hosted by Jason Kirby, with 121 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Jason Kirby hosts $100M Exits with Jason Kirby, a business show with 121 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #119

  EP 119: From Family Liquor Empire to $300M Fund

  Jul 30, 202642 min

  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 scratch, and then deploy $300M backing the founders most investors overlook. Brian has lived every side of the deal table — operator, seller, and now investor — and he's not holding back on what he got wrong the first time. Brian scaled his family's liquor business from $30M to $100M in revenue, sold to PE, then built and sold BevStrat for $20M+ in just four years. Today he manages over $300M in AUM through InvestBev, one of the few firms exclusively focused on the alcohol beverage category — including a unique bet on bourbon barrel inventory that now holds roughly 10% of the country's supply. What You'll Learn: Why selling too much equity early cost Brian ~$10M and what to do differently How a strategic buyer will always outpay a financial buyer Why celebrity brand deals are a trap and what actually drives brand success The real reason 95% of beverage brands fail — and how to be in the 5% Why alcohol is one of the most non-correlated asset classes available to investors 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+119&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=EP+119&utm_campaign=%24100M+Exits ---------------------------------------------- ABOUT BRIAN ROSEN Brian Rosen is the CEO and General Partner of InvestBev Capital, the largest private equity platform in the U.S. dedicated to the spirits, wine, and beverage CPG sectors. He has scaled the firm to $350M AUM and $100M in private credit, supporting brands across all stages of growth while delivering first-quartile returns. With deep roots in the beverage industry across three generations, Brian has led M&A transactions, structured innovative financing solutions, and partnered with global leaders like Beam Suntory and BlackRock. He is recognized as a leading voice in alcohol beverage investing and a key builder of the modern global spirits investment ecosystem. You can reach out to Brian through: LinkedIn: https://www.linkedin.com/in/briandavidrosen Website: https://www.investbev.com - Company Email: brian@investbev.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.

  ListenShow Notes
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  Episode #118

  Ep 118: The AI Divide Is Here: Why Most Companies Will Fall Behind

  Jun 25, 202647 min

  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 investment committees are stalling deals, why founders are being forced to rethink exits, and how AI is rapidly becoming the deciding factor between survival and irrelevance. The conversation dives deep into what growth equity firms actually look for, how deal structures work behind the scenes, and why many founders misunderstand the moment they’re truly ready to scale. Jim also shares lessons from contrarian bets in ad tech, failed hyper-local rollouts, and the hidden dynamics that kill M&A deals in the final hour. They also explore: Why every company now needs to become AI-native The dangerous gap between public and private market valuations How PE firms think during market corrections What causes acquisition deals to collapse mid-process Why missing projections is a “death sentence” in M&A The new reality of SaaS valuations and AI premiums How great founders pivot before disruption kills the business This is a candid look inside the boardroom conversations shaping the next generation of exits, acquisitions, and AI-native companies. 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+118&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=EP+118&utm_campaign=%24100M+Exits ABOUT JIM FERRY Jim Ferry joined Volition Capital in 2014 and focuses on evaluating and supporting investment opportunities across internet and consumer businesses, including marketplaces, ad tech, consolidation platforms, and transactional companies. He works closely with founders and portfolio companies, serving on the boards of several high-growth businesses, including Aditude, Doing Things, Keynes, Linkby, Revi, and Rounds. Jim is known for his partnership-driven approach to investing, spending much of his time working directly with entrepreneurs to help them navigate growth and scale their businesses. You can reach out to Jim through: LinkedIn: https://www.linkedin.com/in/jim-ferry-91b33375 Twitter: https://www.jimferryvc Website: https://www.volitioncapital.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.

  ListenShow Notes
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  Episode #116

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

  May 28, 202654 min

  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.

  ListenShow Notes
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  Episode #115

  EP 115: How We 10X'd EBITDA in 7 Years

  May 21, 202647 min

  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.

  ListenShow Notes
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  Episode #113

  EP 114 | What Founders Get Wrong After Making Millions From an Exit

  Apr 30, 202646 min

  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.

  ListenShow Notes

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