Couverture de $100M Exits with Jason Kirby

$100M Exits with Jason Kirby

$100M Exits with Jason Kirby

De : 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 Direction Economie Management et direction
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    • 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
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