$100M Exits with Jason Kirby

Jason Kirby

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

    MAR 5

    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.

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

    FEB 26

    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.

    1h 1m
  3. EP 106: How Sendoso Raised $100M From SoftBank w/ Kris Rudeegraap

    FEB 19

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

    FEB 12

    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
  5. EP 104: The Psychology Driving Fundraising, VC Decisions, and Founder Failure w/ Aram Attar

    JAN 29

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

    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.

    49 min
  6. EP 103: Built a $100M Software Business at 22 | Matthew Wyatt, Founder of TechTorque

    JAN 22

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

    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.

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

    JAN 15

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

    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 founderWhy fundraising looks easy from the outside—and why it isn’t the biggest mindset shift Nelson made going from VC to founderWhat he’d do differently if he had to raise again tomorrowWhy 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.

    46 min
  8. EP 101: Unicorn Founder Raises $8M Using AI (Andrew D’Souza, Clearco & Bordy.ai)

    12/11/2025

    EP 101: Unicorn Founder Raises $8M Using AI (Andrew D’Souza, Clearco & Bordy.ai)

    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 Episode How Andrew D’Souza raised $8M using an AI agent (Bordy.ai) Why the “warm intro” is dead — and what replaces it How Clearco scaled to a $2.5B unicorn Why investors chase the same 50 deals (and what founders should do instead) A breakdown of what’s actually broken in fundraising today The mechanics of AI-driven dealflow, investor matching, and credibility building 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=Episode101&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=Episode101&utm_id=%24100M++Exits Here's what you're in for: 00:00 Introduction and Guest Welcome 00:16 Using AI to Raise Funds 01:11 The Evolution of Fundraising 05:02 Clear Co: Building a FinTech Unicorn 08:56 Transitioning from Clearco to AI 18:37 The Birth of Boardy 25:45 The Initial Growth Strategy 26:23 Defining Bordy's Vision and Purpose 27:23 Building a Horizontal AI Platform 27:55 Achieving Network Effects and User Success Stories 28:57 Experimenting with Investor-Founders Matching 30:12 The Importance of Trust in Business Introductions 31:41 Boardy's Unique Onboarding Process 36:23 Future Plans: Monetization and Expansion 47:54 The Role of AI in Human Relationships 53:17  How to Connect with Andrew ABOUT Andrew D’Souza Andrew 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/andrewdsouza Linkedin: https://ca.linkedin.com/in/andrewdsouza  Instagram:https://www.instagram.com/andrewdsouza/  Website:https://www.boardy.ai/  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.

    56 min
5
out of 5
6 Ratings

About

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!