$100M Exits with Jason Kirby

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.

From building a $100M software business to watching it fall apart—here’s what really happened.He built a software company from the ground up and scaled it past $100M in sales.Matthew Whyatt started his first tech business at 22—and learned the hard way what happens when growth, partners, and focus drift off course.In this episode, Matthew breaks down the real story behind scaling fast, losing focus, and the lessons that reshaped how he thinks about sales, leadership, and building sustainable companies. He shares why sales is the lifeblood of every business, how founder-led sales eventually breaks, and what it actually takes to build a repeatable sales culture.If you’re a founder navigating growth, sales, or scaling challenges, this conversation is full of hard-earned lessons.What you’ll learn in this episode:How Matthew scaled a software business past $100M in salesWhy diversifying too early can derail focus on your core businessHow misplaced trust and lack of verification can destroy a companyWhat breaks when a founder-led sales team tries to scaleHow to build a repeatable sales culture rooted in diagnosis, not pitchingRaising 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+103&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+103&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Introduction and Guest Welcome00:36 Starting a Business at 2201:14 Early Marketing Strategies01:57 Expansion and Diversification04:26 Challenges with Business Partners11:07 Boardroom Dynamics and Decision Making22:41 Sales Culture and Ethical Practices26:11 Opening a New Zealand Office27:28 Financial Troubles and Trust Issues29:04 Tax Problems and Internal Mismanagement30:06 Data Supplier Issues and Business Liquidation32:49 Rebuilding and Moving Forward37:45 Sales Strategies and Lessons Learned40:43 Advice for Founders on Sales Culture49:40 The Importance of Diagnosis in Sales55:42 Final Thoughts and Contact InformationABOUT MATTHEW WHYATTMatthew is a sales and go-to-market expert with over 25 years of experience in software and SaaS. He has built, scaled, and exited multiple software businesses and has been involved in more than $100M in tech sales.He is the founder of TechTorque, where he helps software and SaaS companies sharpen their strategy, improve their sales process, and build revenue-driving marketing engines.Matthew is also the host of The CEO and the Salesman, a podcast focused on practical lessons from founders and operators on what actually works in business.You can reach out to Matthew through:LinkedIn: https://www.linkedin.com/in/matthewwhyatt/ Website: https://techtorque.com.au/ 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.

Andrew D’Souza, ex-co-founder of Clearco and now Boardy.ai, explains how he went from building a billion-dollar FinTech company to creating an AI “super-connector” that changes how founders meet investors.Andrew breaks down why warm intros no longer work, how Boardy.ai sparked investor interest before he was even fundraising, and why real-time AI conversations may become the future of dealmaking. He also shares ideas on founder psychology, network effects, and the next chapter of AI-driven relationship building.What You’ll Learn in This EpisodeHow Andrew D’Souza raised $8M using an AI agent (Bordy.ai)Why the “warm intro” is dead — and what replaces itHow Clearco scaled to a $2.5B unicornWhy investors chase the same 50 deals (and what founders should do instead)A breakdown of what’s actually broken in fundraising todayThe mechanics of AI-driven dealflow, investor matching, and credibility buildingRaising 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=Video&utm_campaign=Episode101&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode101&utm_id=%24100M++ExitsHere's what you're in for:00:00 Introduction and Guest Welcome00:16 Using AI to Raise Funds01:11 The Evolution of Fundraising05:02 Clear Co: Building a FinTech Unicorn08:56 Transitioning from Clearco to AI18:37 The Birth of Boardy25:45 The Initial Growth Strategy26:23 Defining Bordy's Vision and Purpose27:23 Building a Horizontal AI Platform27:55 Achieving Network Effects and User Success Stories28:57 Experimenting with Investor-Founders Matching30:12 The Importance of Trust in Business Introductions31:41 Boardy's Unique Onboarding Process36:23 Future Plans: Monetization and Expansion47:54 The Role of AI in Human Relationships53:17 How to Connect with AndrewABOUT Andrew D’SouzaAndrew D’Souza is a veteran founder and tech operator best known for co-founding and leading Clearco, the company that transformed non-dilutive capital and funded 10,000+ startups with over $2.5B deployed. With a background in Systems Design Engineering from the University of Waterloo, Andrew now invests, advises, and serves as a visiting partner at HF0, helping high-potential founders scale faster and build category-defining companies.You can reach out to Andrew through:X: https://x.com/andrewdsouzaLinkedin: https://ca.linkedin.com/in/andrewdsouza Instagram:https://www.instagram.com/andrewdsouza/ Website:https://www.boardy.ai/ 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.

In this episode, we break down how founders and early employees can get liquidity before an IPO—without selling shares, triggering taxes, or relying on a shaky secondary market. Our guest is Greg Brogger, founder of SharesPost (sold to Forge Global for $160M, later taken public and acquired) and now CEO of Collective Liquidity.Greg is one of the earliest architects of the private stock market, with over $10B+ in transactions. He covers:Why founders often wait too long for personal liquidityThe hidden risks of SPVs and secondary marketplacesHow to diversify equity without paying capital gainsWays to create a “financial floor” while still buildingHow exchange funds work—and why top founders use themIf you’re a founder, operator, or employee with meaningful equity, this episode shows how to unlock liquidity and reduce personal risk well before an exit.Raising capital?Get a vetted list of VCs: ⁠https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+99&utm_campaign=%24100M+ExitsFundraising insights: ⁠https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+99&utm_campaign=%24100M+ExitsEpisode Guide:00:00 - Selling SharesPost01:04 - COVID-19 challenges01:51 - Broker dealer model shift03:45 - Merger vs acquisition07:04 - Fundraising dynamics11:14 - Building SharesPost16:54 - Employee liquidity pushback19:28 - SPVs & market health23:13 - Nasdaq joint venture29:47 - Strategic moves31:11 - JV dynamics32:32 - Growth & COVID impact34:53 - Timing in venture37:07 - Founding Collective40:04 - Exchange funds46:21 - Liquidity strategies50:50 - Advice for founders57:43 - Key takeawaysAbout Greg BroggerGreg Brogger pioneered private-market trading as the founder of SharesPost, later merging with Forge. Before that, he helped build the Nasdaq Private Market and co-founded TrueCar and Internet Brands. He began his career as a securities attorney at Wilson Sonsini and holds degrees from UC Berkeley, UPenn Law, and Wharton. He currently serves on the board of Ownera.LinkedIn: ⁠https://www.linkedin.com/in/gregbrogger/⁠Website: ⁠https://www.collectiveliquidity.com/⁠About Jason KirbyJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders navigate fundraising and M&A. He’s a serial entrepreneur with four exits and over $135M in transactions.Email: ⁠jason@thunder.vc⁠LinkedIn: ⁠https://www.linkedin.com/in/jasonrkirby/⁠About $100M ExitsThis podcast helps founders navigate capital strategy, funding, and M&A through conversations with those who’ve done it. Best suited for founders doing $5M+ in revenue. Subscribe and share who you’d like to hear next.

He sold his Adtech company to Oracle after burning out, took it easy, then raised $100M+ for his next venture. Most founders dream of a big exit but few talk about what happens after.Subscribe & get our free investor/buyer list at thunder.vc.Key Takeaways:The emotional and mental cost behind selling Crosswise to Oracle.How burnout nearly ended Ron’s startup journey—and what pulled him back.The surprising truth about life inside a big corporation after acquisition.Why Sentra’s $100M+ raise was more about mission than money.Ron’s lessons on cofounder chemistry, resilience, and building without losing yourself.-------------------------------------------------------------------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=Video&utm_campaign=Episode97&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode97&utm_id=%24100M++ExitsHere's what you're in for:01:28 - Mental Health in Entrepreneurship02:55 - Starting the Podcast: Oracle Acquisition Journey03:32 - The Decision to Sell Crosswise09:29 - Navigating the Acquisition Process22:27 - Post-Acquisition Reflections and Retention28:26 - Market Dynamics and Strategic Decisions30:29 - Navigating Competitive Markets31:23 - The Catalyst for Starting Anew32:45 - Building with Friends and Finding Happiness35:25 - Defining the Right Role37:31 - Raising a Monster Seed Round42:25 - The FOMO Round and Series B Success49:28 - Investing in Founding Teams54:54 - Advice for Founders on Raising Money and Selling Companies58:06 - Final Thoughts and Wrap-UpABOUT RON REITERRon is a serial entrepreneur and cloud security expert known for turning complex technical challenges into scalable, real-world solutions. As the Co-founder and CTO of Sentra, he leads innovation in data security helping organizations regain visibility and control over their cloud environments.Before Sentra, Ron co-founded Crosswise, a cross-device identification company that bridged digital identities across devices and was later acquired by Oracle for $50 million.With over two decades in software development and more than six years as an Engineering Director at Oracle Data Cloud, Ron managed the Tel Aviv R&D branch and led initiatives across ID graph, DMP, audience, and contextual data products. His career reflects a deep commitment to building secure, intelligent systems that power the future of data-driven organizations.You can reach out to Ron through:Website:https://www.sentra.io/ Linkedin:https://www.linkedin.com/in/ronreiter/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.

Most founders sell the wrong way. Here’s how to do it right.📣 Subscribe & get our free investor/buyer list at https://web.thunder.vc/vc-investor-listWhat you’ll learn in this episode:Forget the unicorn dream. This is how real founders achieve life-changing exits. Jason Kirby and Oliver Low — partners at Thunder — break down how to navigate the M&A process from both sides of the table: when to sell, how to structure a deal, and what to avoid when your future is on the line.🔥 3-6 Tactical Takeaways:Why timing your exit matters more than valuationHow to avoid the #1 killer of founder wealth: earnoutsThe rise of private equity buyers and what it means for startupsHow “venture orphans” can still create massive outcomesWhat Thunder looks for before taking founders to marketWhen Oliver Low sold his startup, it wasn’t a clean, overnight success story.It was years of building, negotiating, and learning the hard way how M&A really works.His company, Platform 360, eventually became part of a public company listed on the London Stock Exchange but the journey there was anything but straightforward.There were earnouts that didn’t go as planned.Buyers who vanished mid-deal.And market conditions that turned every negotiation into a gamble.For founders considering an exit or just trying to understand how real M&A unfolds — this conversation is a masterclass in playing the long game.Want more insights? Check out the full shownotes for Episode 95! HERE

Europe’s next defense-tech giant is being built in London. Subscribe & get our free investor/buyer list at thunder.vcHow Max Buchan helped take CoinShares from $0 to $50M revenue to $1.5B IPO —without VC money.The insider story behind founding Valarian, the UK’s answer to Palantir.Raising $20M in seed funding to build dual-use infrastructure for governments and enterprises.The shift from crypto to defense tech and why “digital sovereignty” is the next trillion-dollar opportunity.How Valarian attracted elite talent from Palantir, Darktrace, and top U.S. defense innovators.Lessons for founders raising capital in deep tech and dual-use markets.—-----------------------------------------------------------------------------------------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=Video&utm_campaign=Episode93&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode93&utm_id=%24100M++ExitsHere’s what you’re in for:00:00 – How CoinShares hit $50M revenue with no VC03:30 – The problem that sparked Valarian: cross-border data control06:00 – Pivoting from secure messaging to compliance infrastructure08:30 – Raising $11M pre-product and landing IQ Capital & Molten Ventures10:20 – Expanding to $20M total seed and U.S. strategic backers13:40 – How defense tech funding evolved post-Ukraine16:00 – Defining product-market fit for dual-use infrastructure18:00 – Recruiting Palantir and Darktrace execs to Valarian23:30 – Why the UK talent system lags behind the U.S.32:00 – Operating in stealth: why Valarian waited to go public35:30 – The hardware Pelican Case: Valarian’s deployable defense tech37:00 – Consolidation and M&A in Europe’s defense tech ecosystem39:00 – Advice for founders building category-defining companies----------------------------------------------------ABOUT MAX BUCHANMax Buchan is the Founder and CEO of Valerian, a company building next-generation digital infrastructure to solve global data sovereignty challenges.Before launching Valerian, Max was the first employee at CoinShares, where he worked directly with the co-founder and CEO. In just 18 months, CoinShares grew from an idea to over $55 million in revenue and nearly $2 billion in assets under management, expanding to almost 200 employees and later going public on the Nasdaq with a $1B+ valuation.His experience scaling CoinShares across London, New York, Paris, Stockholm, and Jersey revealed a growing problem—how international companies manage data across borders. That insight inspired him to start Valerian, focused on digital sovereignty and secure global infrastructure.Max holds a degree in History and Economics from the University of London and was named to the Forbes 30 Under 30 Europe list for Technology.You can reach out to Max through:Website: https://www.valarian.com/LinkedIn: linkedin.com/in/maxbuchanABOUT JASONJason Kirby is the Managing Partner at Thunder.VC and host of $100M Exits. He’s helped thousands of founders navigate capital raises, M&A, and exits, with a focus on tactical, data-backed strategies.You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/