Épisodes

  • EP 106: How Sendoso Raised $100M From SoftBank w/ Kris Rudeegraap

    EP 106: How Sendoso Raised $100M From SoftBank w/ Kris Rudeegraap
    Feb 19 2026
    From raising $100M from SoftBank to shifting from “growth at all costs” to building a durable business, Kris shares the real story behind scaling Sendoso to over $100M in revenue.In this episode of $100M Exits, Kris walks through what it was actually like pitching Masayoshi Son over Zoom, deploying nine figures into aggressive hiring, then quickly pivoting when the zero-interest-rate era ended. He breaks down the hard decisions around efficiency, acquisitions, AI-driven sales automation, international expansion, and why building a 100-person advisory network became his secret weapon.This isn’t just a fundraising story. It’s a lesson in adapting fast, evolving as a leader, and making bold moves when the market shifts.If you're building toward nine figures in revenue — or trying to survive the jump from hypergrowth to operational discipline — this episode is packed with real-world insight.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+106&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+106&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Welcome and Kris from Sendoso 00:36 How SoftBank found Sendoso 02:07 The call with Masayoshi Son 04:46 What Kris did after the $100M landed 09:20 Using AI to scale sales without more headcount 12:11 Switching from hypergrowth to efficiency 16:32 Why Sendoso bought competitors 25:58 Making the merger work day one 27:18 The integration plan that kept it on track 28:03 Who they kept and who they didn’t 28:46 The tech migration and what took longer 29:47 M&A advice for founders 31:00 Talking to competitors before you need to 33:15 Why Kris chose a co-CEO setup 38:49 How Sendoso expanded internationally 44:17 How Kris changed as a leader 49:24 The advisor network that became a cheat code 51:42 Wrap up and how to connectABOUT KRIS RUDEEGRAAPKris Rudeegraap is the Co-Founder and CEO of Sendoso, an AI-powered sending platform helping B2B companies create meaningful engagement through personalized gifts, swag, and eGifts. He founded the company after recognizing a gap in how sales and marketing teams build real connections, drawing from over a decade in software sales.Under his leadership, Sendoso has scaled globally with strong venture backing, driven by his belief that authentic, personalized experiences win in a digital-first world.You can reach out to Kris through:LinkedIn: https://www.linkedin.com/in/rudeegraap/ Website: https://www.sendoso.com/ Email: kris@sendoso.comABOUT 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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    55 min
  • EP 105: From CEO to Employee: The Hardest Pivot of a Founder’s Career

    EP 105: From CEO to Employee: The Hardest Pivot of a Founder’s Career
    Feb 12 2026
    From building a booming business overseas to being forced to start over, this is the founder journey most people never talk about.James Rose built and scaled an online furniture company during a massive property boom in Eastern Europe—only to see it nearly collapse during the global financial crisis. After years as an entrepreneur, he was forced to swallow his pride, re-enter the job market, and rebuild through sales and leadership roles.In this episode, James shares the unfiltered reality of going from founder to employee—and back again. He breaks down how sales became his lifeline, why founders delay exit planning, and how those lessons led him to build Inflectiv Group, a platform acquiring and rolling up profitable, founder-led agencies.If you’re a founder thinking about scale, resilience, or engineering a meaningful exit, this conversation delivers clarity without the hype.What you’ll learn in this episode:Why most founders avoid the reality check needed to plan a real exitHow losing a business reshapes your view of risk, pride, and employabilityWhy sales is one of the fastest paths to rebuilding after a setbackThe biggest mistakes founders make when fundraising or delaying M&AHow minority roll-ups unlock value for founder-led service businessesWhat acquirers actually look for in profitable agencies todayRaising 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+105&utm_campaign=%24100M+Exits⁠Get the latest fundraising insights, news, and tips:⁠https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+105&utm_campaign=%24100M+Exits⁠Here's what you're in for:00:00 Introduction and Guest Welcome00:17 James Rose’s First Business Venture02:07 The Impact of the Global Financial Crisis04:09 Transitioning From Founder to Employee11:21 Re-entering Entrepreneurship Through M&A15:29 Market Trends and Acquisition Strategies29:58 Advice for Founders on Valuation and Exits36:35 Where to Learn More About JamesABOUT JAMES ROSEHe is the founder and CEO of Inflectiv Group, an investment firm backing independent marketing and communications agencies through minority investments, growth capital, and strategic support—while allowing founders to retain autonomy and control.A serial entrepreneur, investor, and growth leader, James brings over 20 years of experience across media, technology, and M&A. He has created significant shareholder value in private equity–backed businesses by scaling revenue from £0.5M to £7M+ and building effective go-to-market strategies.He has also worked closely with product and development teams to commercialize innovative SaaS offerings, bridging product vision and market execution. Today, James applies this hands-on experience to helping agency founders scale sustainably through disciplined growth and smart capital partnerships.You can reach out to James through:LinkedIn: https://www.linkedin.com/in/jamesroseequitypartners/⁠Website: ⁠https://www.inflectivgroup.com/⁠ABOUT JASON KIRBYCo-founder of Thunder, a tech-enabled investment bank helping founders achieve ideal outcomes through capital strategy and M&A.A serial entrepreneur with four exits, Jason has decades of experience in fundraising, M&A, and business building. He has coached hundreds of founders and transacted over $135M personally, with Thunder exceeding $200M+ in completed transactions.You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: ⁠https://www.linkedin.com/in/jasonrkirby/⁠ABOUT $100M EXITSThe goal of $100M Exits is simple: equip founders with the knowledge and guidance to navigate capital strategy by learning from founders and investors who’ve already done it.For some, the dream is a $100M+ exit. For others, it’s cash flow or IPO. Founders doing over $5M in revenue will benefit most from this podcast.Be sure to subscribe—and let me know who you want interviewed next.
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    38 min
  • EP 104: The Psychology Driving Fundraising, VC Decisions, and Founder Failure w/ Aram Attar

    EP 104: The Psychology Driving Fundraising, VC Decisions, and Founder Failure w/ Aram Attar
    Jan 29 2026

    Most founders fail for psychological reasons—not tactical ones.


    In this episode of $100M Exits, Jason Kirby sits down with Aram Attar, founder of The VC Factory, to unpack the hidden psychology shaping fundraising outcomes, VC decisions, and why smart founders keep repeating the same mistakes.

    With 15+ years advising founders, sitting on boards, and training venture capitalists, Aram shares a clear conclusion: most failures aren’t about intelligence, strategy, or effort—they’re about how decisions are made under uncertainty.

    They explore the difference between trying to win versus trying not to lose, how VC psychology impacts fundraising more than your pitch, the hidden risks in earnouts and partial exits, and why the strongest teams balance promotion- and prevention-focused thinkers.


    Subscribe & get our free investor/buyer list at https://thunder.vc


    Key Takeaways

    Why founders repeat mistakes—even after seeing others fail

    Trying to win vs trying not to lose

    How VC psychology shapes fundraising outcomes

    Risks in earnouts, partial exits, and misalignment

    Why balanced thinking drives better decisions

    What you’ll learn in this episode

    Why a “5-year plan” often turns into a 20-year journey

    How VCs avoid the sunk-cost trap in bridge financing

    The mindset frameworks behind outlier investment betsHow to spot “what can go right?” vs “how do I not lose?” investors

    The #1 mistake first-time fund managers make with fund size


    Raising capital?

    Get a list of vetted VCs for FREE:https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode104&utm_id=%24100M++Exits


    Get the latest fundraising insights:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode104&utm_id=%24100M++Exits

    Timestamps:

    00:00 Introduction

    00:39 A 20-year journey to a $2.2B exit

    01:57 How VCs make decisions

    03:50 Investing in a Mexican retail company

    06:20 What mindset-based investing really means

    10:04 Behavioral insights every founder should know

    15:34 Research behind successful VC thinking

    23:43 Missed deals and costly VC mistakes

    24:20 How investment committees really work

    24:51 The champion rule in venture capital

    26:06 Inside the investment committee process

    29:37 Why founder empathy matters

    33:04 The power of honest communication

    36:28 How to evaluate emerging fund managers

    43:01 Advice for new fund managers

    46:29 Final thoughts and key resources


    ABOUT ARAM

    Aram Attar is a venture capitalist and founder of The VC Factory, focused on improving venture outcomes by shaping how investors and founders think, decide, and align. His work spans advising VC funds, CEOs, governments, and accelerator programs, with an emphasis on psychology, character, and long-term performance.

    LinkedIn: https://www.linkedin.com/in/aram-attar/

    Website: https://thevcfactory.com/


    ABOUT JASON KIRBY

    Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders navigate capital strategy and M&A. A serial entrepreneur with four exits, Jason has coached hundreds of founders and led transactions totaling $200M+ through Thunder.

    Email: jason@thunder.vc

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


    ABOUT $100M EXITS

    $100M Exits equips founders with the insight and guidance needed to navigate capital strategy through conversations with founders and investors who’ve already done it. Best suited for founders doing $5M+ in revenue.

    Be sure to subscribe and let us know who you want us to interview next.
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    49 min
  • EP 103: Built a $100M Software Business at 22 | Matthew Wyatt, Founder of TechTorque

    EP 103: Built a $100M Software Business at 22 | Matthew Wyatt, Founder of TechTorque
    Jan 22 2026

    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 sales

    Why diversifying too early can derail focus on your core business

    How misplaced trust and lack of verification can destroy a company

    What breaks when a founder-led sales team tries to scaleHow to build a repeatable sales culture rooted in diagnosis, not pitching


    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+103&utm_campaign=%24100M+Exits

    Get the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+103&utm_campaign=%24100M+Exits

    Here's what you're in for:

    00:00 Introduction and Guest Welcome

    00:36 Starting a Business at 22

    01:14 Early Marketing Strategies

    01:57 Expansion and Diversification

    04:26 Challenges with Business Partners

    11:07 Boardroom Dynamics and Decision Making

    22:41 Sales Culture and Ethical Practices

    26:11 Opening a New Zealand Office

    27:28 Financial Troubles and Trust Issues

    29:04 Tax Problems and Internal Mismanagement

    30:06 Data Supplier Issues and Business Liquidation

    32:49 Rebuilding and Moving Forward

    37:45 Sales Strategies and Lessons Learned

    40:43 Advice for Founders on Sales Culture

    49:40 The Importance of Diagnosis in Sales

    55:42 Final Thoughts and Contact Information


    ABOUT MATTHEW WHYATT

    Matthew 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 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.
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    59 min
  • EP 102: He Raised $76M With No Defense Tech Background | Nelson Mills Founder of VATN Systems

    EP 102: He Raised $76M With No Defense Tech Background | Nelson Mills Founder of VATN Systems
    Jan 15 2026

    From VC intern to $76M raised, here’s how it really happened.

    He raised $76M in two years—without ever working in defense tech.

    Nelson Mills, co-founder and CEO of a fast-growing underwater defense startup. Shares how he went from a VC intern to leading a company building autonomous undersea vehicles and why the maritime defense space became the perfect opportunity.

    He breaks down how he validated the market, assembled a world-class team, and raised more than $76M across multiple rounds.

    What you’ll learn in this episode:

    • How Nelson raised $3.5M pre-seed, $13M seed, and a $60M Series A as a first-time founder
    • Why fundraising looks easy from the outside—and why it isn’t the biggest mindset shift Nelson made going from VC to founder
    • What he’d do differently if he had to raise again tomorrow
    • Why raising capital ≠ success (and what actually matters)


    Subscribe & get our free investor/buyer list at thunder.vc.

    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=Episode102&utm_id=%24100M++Exits

    Get the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode102&utm_id=%24100M++Exits

    Here's what you're in for:

    00:00 Intro

    00:06 From VC intern to founder

    01:18 Finding the opportunity in underwater defense

    02:56 Technical challenges & innovations

    07:23 Building investor relationships

    10:57 Inside the seed round

    23:17 Hiring & talent strategy

    26:31 Competing in defense tech

    28:24 Customer-driven product thinking

    29:29 Why lobbying starts on day one

    32:49 Navigating government sales

    34:23 Capital strategy & funding options

    37:28 Scaling hardware & supply chain

    44:18 Building a company with family

    46:00 Nelson’s advice for defense-tech founders

    48:38 Final thoughts


    ABOUT NELSON MILLS

    Nelson Mills is the founder and CEO of Vatn Systems, an underwater vehicle startup building some of the world’s lowest-cost, high-production UUVs. In just 15 months, he led the company from concept to TRL 7, raising more than $3.5M in venture capital and assembling a team pushing the boundaries of maritime tech.Before launching Vatn, Nelson led hull development at Pure Watercraft, a marine electrification company backed by over $170M in funding.

    He later moved into venture capital, with roles at Link Ventures, Lux Capital, and Global Founders Capital, giving him a unique lens on product development, capital strategy, and scaling deep-tech companies.Nelson holds both a BA and an MBA from Columbia University and brings a blend of engineering insight, founder grit, and investor perspective to everything he builds.

    You can reach out to Nelson Wills through:

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


    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.vcLinkedIn: 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.
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    46 min
  • 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)
    Dec 11 2025
    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 min
  • 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
    Dec 4 2025
    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 min
  • 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
    Nov 27 2025

    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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