『$100M Exits with Jason Kirby』のカバーアート

$100M Exits with Jason Kirby

$100M Exits with Jason Kirby

著者： Jason Kirby
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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!Jason Kirby マネジメント・リーダーシップ リーダーシップ 経済学
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  • EP 101: Unicorn Founder Raises $8M Using AI (Andrew D’Souza, Clearco & Bordy.ai)

    EP 101: Unicorn Founder Raises $8M Using AI (Andrew D’Souza, Clearco & Bordy.ai)
    2025/12/11
    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.
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    56 分
  • EP 100: The Earnout Trap: What This Founder Learned After Selling His Company

    EP 100: The Earnout Trap: What This Founder Learned After Selling His Company
    2025/12/04
    After 20 years of steady, bootstrapped growth, Eric Friedman sold his company, eSkill, an online skills testing platform used by employers worldwide.In this episode, Eric breaks down how he built a profitable SaaS business with no outside funding, ran three separate sales processes, and closed a deal with private equity in 2024. He shares what founders should know about earnouts, how to choose the right investment bank, and the red flags he learned to spot during M&A negotiations.If you’re a founder thinking about selling a bootstrapped company, this episode is packed with real lessons on timing, valuation, and life after the exit.⚡ What You'll Learn: Why most earnouts never get paid — and how to protect yourself.The hidden risks behind LOIs, retrades, and exclusivity windows.How a dev-shop equity arrangement fueled 20 years of bootstrapped growth… until it didn’t.How interest rate spikes in 2022 instantly destroyed a great LOI.Why Eric ran three processes before landing the final buyer.How to evaluate PE buyers and spot red flags during diligence.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=Episode100&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=Episode100&utm_id=%24100M++ExitsHere's what you're in for:00:00 Introduction03:40 Choosing an Investment Bank06:22 Running the Sale Process15:42 Finalizing the Deal and Advice for Founders19:59 Evaluating Potential Bosses and Partners20:25 The Importance of Thorough Due Diligence21:34 Transparency in Negotiations23:22 Understanding and Negotiating Earnouts24:47 Post-Acquisition Transition35:39 Life After the Exit37:21 Final Advice for FoundersABOUT ERIC FRIEDMANEric Friedman is an accomplished startup CEO with over two decades of experience leading and scaling SaaS companies. As the founder and CEO of eSkill Corporation, he built the company from concept to successful exit—achieving 20 consecutive years of revenue growth without outside funding. Under his leadership, eSkill became a leader in the HR technology space, serving global clients such as PepsiCo, GE, Deloitte, Stanford University, Zappos, the United Nations, and the U.S. State Department.He brings deep expertise in lean operations, sustainable growth strategy, and product-market adaptation. His ability to lead through both stable and volatile market conditions has made him a trusted operator in the SaaS space. His approach blends strategic discipline with operational agility—adapting go-to-market models and product fit in response to shifting customer and market needs.You can reach out to Eric through:LinkedIn: https://www.linkedin.com/in/eric-friedman-604258/ 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.
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    45 分
  • EP 99: From Zero to $10B in Secondaries: Greg Brogger 's Journey to a $160M Exit

    EP 99: From Zero to $10B in Secondaries: Greg Brogger 's Journey to a $160M Exit
    2025/11/27

    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 liquidity
    • The hidden risks of SPVs and secondary marketplacesHow to diversify equity without paying capital gains
    • Ways to create a “financial floor” while still building
    • How exchange funds work—and why top founders use them

    If 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+Exits

    Fundraising insights: ⁠https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+99&utm_campaign=%24100M+Exits

    Episode Guide:

    00:00 - Selling SharesPost

    01:04 - COVID-19 challenges

    01:51 - Broker dealer model shift

    03:45 - Merger vs acquisition

    07:04 - Fundraising dynamics

    11:14 - Building SharesPost

    16:54 - Employee liquidity pushback

    19:28 - SPVs & market health

    23:13 - Nasdaq joint venture

    29:47 - Strategic moves

    31:11 - JV dynamics

    32:32 - Growth & COVID impact

    34:53 - Timing in venture

    37:07 - Founding Collective

    40:04 - Exchange funds

    46:21 - Liquidity strategies

    50:50 - Advice for founders

    57:43 - Key takeaways


    About Greg Brogger

    Greg 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 Kirby

    Jason 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.vc⁠

    LinkedIn: ⁠https://www.linkedin.com/in/jasonrkirby/⁠


    About $100M Exits

    This 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.
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    1 時間
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