$100M Exits with Jason Kirby

Jason Kirby
  • 5.0 (2)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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!

  1. EP 112: How He Built and Sold a $100M Startup Twice | Dan Rosenberg

    7 HR AGO

    EP 112: How He Built and Sold a $100M Startup Twice | Dan Rosenberg

    He built a $100M creator platform—and sold it twice. Here’s what actually happens after the deal closes. Daniel Rosenberg, cofounder of Represent.com, shares how he helped creators and celebrities sell products without upfront cost using on-demand production. This removed the biggest barrier for creators: launching a business without upfront cost or inventory risk. In this episode, he explains how Represent grew by working with top talent, why they focused on fewer, higher-value creators, and the risks that came with scaling fast. He also breaks down what really happens when you sell a company—from long deal processes to post-acquisition challenges. Daniel also shares how the creator economy is changing. Today, creators don’t just want sponsorships—they want ownership and equity. What you’ll learn in this episode:If you’re building a startup or thinking about exits, this episode gives you real, practical insights. How creators sell products without upfront cost Why choosing the right market matters The risks of scaling through big deals What actually happens during an acquisition Why many deals fall apart How the creator economy is shifting toward ownership 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+112&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+112&utm_campaign=%24100M+Exits Here's what you're in for: 00:00 Meet Daniel Rosenberg  00:49 Represent Origin Story 03:07 Landing Big Talent 05:26 Growth Engine Explained 07:49 Mayweather Cash Drop 10:06 Licensing With Major IP 11:01 Affiliate Versus Celebrity Focus 15:05 Custom Ink Acquisition 18:18 Deal Terms And Earnout 19:59 Diligence Distraction Lessons 21:40 Post Merger Integration 25:10 Selling To Cameo 29:37 Cameo Integration Reality Check 33:33 Why Dan Stepped Away 35:51 Ownership Shift In Creator Economy 38:20 Partnering With Creators 40:57 Risks And Who Should Worry 43:12 Resources And Closing ABOUT DANIEL ROSENBERG  Daniel “Dan” Rosenberg is a founder and entrepreneur best known for building Represent.com, a platform that helped creators and celebrities sell merchandise without upfront cost. He scaled the company to a $100M+ exit, selling it to Custom Ink, and later helped lead another sale to Cameo. Today, he focuses on the creator economy through Material Group, where he works with creators to build businesses where they have ownership—not just sponsorship deals. You can reach out to Daniel through: LinkedIn: https://www.linkedin.com/in/danielrosenberg1/  Website: https://www.materialgroup.co/  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 much 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.

    47 min
  2. EP 111: How Defense Tech Startups Get Funded | AI, Warfare, and Venture Capital with Brad Harrison @ Scout Ventures | EP 111

    2 APR

    EP 111: How Defense Tech Startups Get Funded | AI, Warfare, and Venture Capital with Brad Harrison @ Scout Ventures | EP 111

    From building startups to backing the future of warfare, this episode covers what founders need to know about capital, defense tech, and AI. Brad Harrison, Founder and Managing Partner of Scout Ventures, shares how fast defense technology is evolving—and why selling into this space is harder than most expect. He explains how AI, drones, and autonomous systems are reshaping warfare, and why success requires more than a strong product—founders need the right networks, industry insight, and an understanding of government buyers. The conversation also covers how deals work in defense tech, what investors look for, and why choosing the right capital matters—especially when navigating government contracts. If you’re a founder, investor, or operator in AI, defense, or emerging tech, this episode offers a clear view on how to build and fund in this space. What you’ll learn: How operator experience shapes investment decisionsWhy defense tech innovation is acceleratingHow AI and autonomous systems are changing warfareWhy startups struggle with defense procurementWhat gets funded in defense tech todayHow to align with real government demandWhy networks and relationships matterWhat drives successful outcomes and exitsWhy understanding the end buyer is criticalHow capital strategy impacts growthRaising 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+111&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+111&utm_campaign=%24100M+Exits Here's what you're in for: 00:00 Entrepreneur Journey 01:55 Founder Support at Scout 03:46 Army Futures Command Shift 05:17 Ukraine Drone Autonomy Leap 08:12 Why US Procurement Lags 10:53 Key Defense Tech Domains 12:43 GPS Denied Navigation 15:17 Next Gen Wireless 6G 18:44 Founder Goals and Focus 20:43 Red Flags and Hard Calls 23:57 What Gets Funded Now 28:19 Vendor Lock Risks 29:11 AI Security Threats 30:31 Autonomy Changes Warfare 31:50 Selling to the Pentagon 32:27 RFPs, TRLs, and SBIRs 35:48 Lobbying and Budgets 38:28 Founder Insight Advantage 41:16 Tomahawk Robotics Exit 44:32 Defense Tech M&A Drivers 49:39 Scout Fund Strategy 51:53 Space Deterrence Vision 56:32 Founder Upside and Wrap ABOUT BRAD HARRISON  Brad Harrison is the Founder and Managing Partner of Scout Ventures, backing companies like ID.me, Voyager Space, and Tomahawk Robotics. A former U.S. Army Airborne Ranger and West Point graduate, he later studied at MIT Sloan, focusing on building new ventures. He has advised leaders at the White House and Pentagon on defense and innovation, and is now based in Austin, Texas. You can reach out to Brad through: LinkedIn:⁠ https://www.linkedin.com/in/bradharrison ⁠ Website: ⁠https://www.scout.vc/⁠  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.

    53 min
  3. EP 110: From Operator to Investor: George Alifragis on Scaling With Non-Dilutive Capital

    27 MAR

    EP 110: From Operator to Investor: George Alifragis on Scaling With Non-Dilutive Capital

    From building and exiting companies to deploying capital at a $1.8B investment firm, George Alifragis has seen both sides—as an operator and now a private credit investor at Metropolitan. In this episode, he breaks down the transition from operator to investor, lessons from scaling a global tech company, and how that shapes how he evaluates businesses today. He shares what really drives EBITDA growth, what makes a company attractive to private equity, and why operators often misunderstand how investors think about risk, growth, and returns. If you’re a founder thinking about exits or capital, this is a clear inside look. What you’ll learn in this episode: What changes when you go from operator to investor How George scaled a global tech company and drove EBITDA growth What makes a business attractive to private equity buyers The key differences between big corporations and mid-sized companies Why growth operators thrive in different environments How investors actually evaluate risk and opportunity Lessons from exiting companies to TELUS and a PE-backed firm Why understanding the capital strategy is critical for a founder 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+110&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+110&utm_campaign=%24100M+Exits Here's what you're in for: 00:00 Welcome and George Alifragis Intro 00:57 Operator Exits and Track Record 02:32 From Bell to Building Altima Telecom 07:24 Why He Left Corporate Life 10:43 Regulation That Forced an Exit 13:56 Moving to Miami and a New Chapter 15:17 Scaling to a Successful Exit 16:53 From Operator to Investor 21:43 Inside Metropolitan’s Investment Thesis 25:14 The Power of an Operator Network 27:01 The Operating Experts Model Explained 27:52 The Fishing Holes Investment Strategy 28:47 Building an Ecosystem Partner Network 30:12 Activating the Network at Scale 32:21 The Deal Flow Flywheel 34:30 How Deals Get Done at Metropolitan 37:45 Alternative Capital Explained 39:22 Structuring Bespoke Hybrid Deals 45:07 A Real Deal Structure Breakdown 50:25 Lessons on Cost of Capital 53:53 Final Thoughts and How to Connect ABOUT GEORGE ALIFRAGIS  George Alifragis is a multi-time operator turned investor, currently at Metropolitan, a $1.8B private credit firm, bringing experience from scaling companies, driving EBITDA growth, and evaluating businesses through an investor lens.He previously served as CEO of a global tech company, leading growth and exiting to a private equity-backed firm, and was earlier part of a successful exit to TELUS, one of Canada’s largest telecom companies. You can reach out to George through: LinkedIn: ⁠https://www.linkedin.com/in/galifragis/⁠  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.

    55 min
  4. EP 109: Why Silicon Valley Founders Are Panicking About AI w/ Jessica Mah

    19 MAR

    EP 109: Why Silicon Valley Founders Are Panicking About AI w/ Jessica Mah

    Jess Mah has built, scaled, and backed companies across multiple waves of Silicon Valley—but what she’s seeing now is different. In this episode of $100M Exits, she explains why even unicorn founders are under pressure in the AI era, where success is no longer about headcount, hype, or old playbooks. AI is compressing execution timelines, raising the bar for traction, and making many traditional founder skills feel outdated. Jess breaks down why relevance, speed, and adaptability now matter more than funding or past wins—and why many experienced founders are struggling to adjust. She also shares how to build lean, AI-first companies, protect your edge, use relationships as market intelligence, and why micro-teams may outperform bloated organizations. If you’re a founder navigating AI disruption, fundraising pressure, and shifting rules of company building, this conversation is a sharp reality check. What you’ll learn in this episode:• How AI is creating pressure even among unicorn founders• Why relevance and speed now matter more than money or status• What founders must unlearn to stay competitive• Why lean teams and micro-teams can outperform larger organizations• How to use side projects to rebuild your AI instincts and leadership edge• Why protecting your information edge matters more than ever 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+109&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+109&utm_campaign=%24100M+Exits Here's what you're in for:00:00 Meet Jess Mah01:21 Silicon Valley Stress04:03 Money Versus Relevance06:12 AI is changing the game11:06 Founders React Poorly14:17 Lean Teams And Traction16:37 Funding Bar Keeps Rising19:33 Differentiation And Wedges22:15 Bias In Venture Funding28:43 AI As Equalizer31:30 Multi-Project Mindset33:56 Building Quietly In Public38:17 Networking As Market Radar42:19 Protecting Your Information Edge50:07 Side Hustles For Legacy Founders56:40 Micro Teams And Reorg Reality59:22 Leadership Reset And Farewell ABOUT JESS MAH Jessica Ma is a serial entrepreneur, investor, and venture builder known for launching and scaling multiple technology companies in Silicon Valley. She founded her first startup while still in college and scaled it to a nine-figure valuation after Y Combinator. Since then, she has founded and incubated more than 10 companies with combined valuations exceeding $1 billion. Today, she focuses on AI-driven ventures and shares insights on how AI is reshaping company building. You can reach out to Jess through:LinkedIn: https://www.linkedin.com/in/jessicamah/Website: https://www.mahway.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.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.

    1 hr
  5. EP 108: Luxury DTC Founder Chris Wichert: Raising $20M, Surviving DTC Collapse & Turnaround Exit

    5 MAR

    EP 108: Luxury DTC Founder Chris Wichert: Raising $20M, Surviving DTC Collapse & Turnaround Exit

    Chris Wichert raised roughly $20M to build a modern luxury sneaker brand, pitching Koio as the “Louis Vuitton for millennials.” After business school, he moved to New York and secured investors, including the Winklevoss twins, Founders Fund, and the founder of Aldo, scaling through press, retail experiments, and premium positioning. Then COVID hit. Retail revenue disappeared. Demand for dress sneakers collapsed. By early 2023, Koio faced roughly -$3M EBITDA in a market where DTC multiples had compressed and fundraising slowed dramatically. In this episode, Chris shares how they reset the business: cutting 40% of SKUs, reducing headcount by 70%, going remote-first, closing most stores, and removing $3M in costs without sacrificing revenue, returning the company to profitability. He also breaks down their exit process: running 200+ buyer conversations, navigating last-minute tariff-related deal risk, and ultimately selling to a Miami family office. If you’re a founder navigating scale, crisis, or exit timing, this episode offers a candid look at capital strategy, cost discipline, and realistic decision-making. What you’ll learn: Why early fundraising is about vision, not just numbers How retail experiments validated a luxury DTC brand What happens when DTC multiples collapse How to cut millions in costs without shrinking revenue Why founders delay tough restructuring decisions How to run a disciplined, proactive M&A process 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+108&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+108&utm_campaign=%24100M+Exits Here's what you're in for:00:00 Meet Koio Founder00:59 Why Raise Early Capital04:43 Retail Growth Playbook08:55 COVID Shock and DTC Reset15:51 Turnaround and Investor Realignment29:19 Choosing a Full Sale30:24 Building the Buyer Universe33:26 Tariffs Shake the Deal39:43 Founder Realism Shift52:43 Capital Traps and Exit Advice ABOUT CHRIS WICHERT Chris Wichert is an entrepreneur and operator best known as the founder of Koio, a digitally native luxury sneaker brand built on craftsmanship and modern positioning. After raising ~$20M in venture capital, he scaled the business through retail expansion and premium brand building before navigating COVID and the broader DTC market collapse. Facing compressed multiples and a shifting capital environment, Chris led a full operational reset — cutting costs, restructuring the team, and restoring profitability — before successfully exiting to a family office. He now speaks and advises on capital strategy, turnaround execution, and proactive exit planning. You can reach out to Chris through: LinkedIn: https://www.linkedin.com/in/chris-wichert1/Website: https://ccatalyst.co/ ABOUT JASON KIRBY Jason Kirby is co-founder of Thunder, a tech-enabled investment bank helping founders reach ideal 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, having coached hundreds of entrepreneurs and transacted over $135M personally; 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: equip founders with knowledge, inspiration, and guidance to navigate capital strategy by interviewing founders and investors who’ve done it. For most, a $100M+ exit is a dream; for others, cash flow or IPO matters. Founders doing over $5M in revenue benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.

    1hr 1min
  6. EP 107: He Pivoted to Survive—Then Sold to Victoria's Secret for ~$700M | Brian Ree

    26 FEB

    EP 107: He Pivoted to Survive—Then Sold to Victoria's Secret for ~$700M | Brian Ree

    From near bankruptcy… to a $700M strategic exit. Here’s how it actually happened. Brian Ree built DailyLook into a premium AI-powered personal styling brand, nearly lost it in 2014, rebuilt it around ruthless unit economics and LTV, merged with Adore Me, and ultimately exited to Victoria’s Secret in a $700 million transaction. In this episode, Brian breaks down the real story behind the pivot that almost killed the company, the $40 styling fee gamble that saved it, how focusing obsessively on lifetime value created a defensible moat, and why relationships drive major exits. He also shares how DailyLook scaled from $30M to $140M post-acquisition, what it’s really like operating inside a public company, and why building a fashion brand is a decade-long grind, not a hype cycle. If you’re building in DTC, fashion, subscription, or thinking about a strategic exit, this is a masterclass in resilience, economics, and timing. What you’ll learn in this episode: How DailyLook built a premium styling subscription powered by AI + human stylists Why negative unit economics nearly killed the company in 2014 The $40 pricing decision that turned the business around How obsessing over LTV created a long-term competitive moat Why most DTC brands fail to control CAC and retention How relationships led to the Adore Me merger and Victoria’s Secret acquisition What it’s like scaling from $50M to $140M inside a public company Why building a fashion brand is a 10+ year commitment 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+107&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+107&utm_campaign=%24100M+Exits For full episode shownotes and resources, view them here.

    1hr 1min
  7. EP 106: How Sendoso Raised $100M From SoftBank w/ Kris Rudeegraap

    19 FEB

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

    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+Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+106&utm_campaign=%24100M+Exits Here'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 connect ABOUT KRIS RUDEEGRAAP Kris 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.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.

    55 min
  8. EP 105: From CEO to Employee: The Hardest Pivot of a Founder’s Career

    12 FEB

    EP 105: From CEO to Employee: The Hardest Pivot of a Founder’s Career

    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 exit How losing a business reshapes your view of risk, pride, and employability Why sales is one of the fastest paths to rebuilding after a setback The biggest mistakes founders make when fundraising or delaying M&A How minority roll-ups unlock value for founder-led service businesses What acquirers actually look for in profitable agencies today 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+105&utm_campaign=%24100M+Exits⁠ Get the latest fundraising insights, news, and tips:⁠https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+105&utm_campaign=%24100M+Exits⁠ Here'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 James ABOUT JAMES ROSE He 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 KIRBY Co-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 EXITS The 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.

    38 min
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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!

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