• Fundraising: Demystified! True Stories Direct From Founders

  • By: Jason Kirby
  • Podcast

Fundraising: Demystified! True Stories Direct From Founders

By: Jason Kirby
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  • Summary

  • 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
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Economics Leadership
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Episodes
  • EP 68: From Bootstrapping to an Eight-Figure Exit with Conor Tomkies

    EP 68: From Bootstrapping to an Eight-Figure Exit with Conor Tomkies
    Jan 9 2025
    From dog genetics to bootstrapping to an eight-figure exit , Conor Tomkies has done it all. As the founder of Support Ninja, Conor scaled a bootstrapped business into a middle eight-figure success story, managing thousands of employees worldwide. After selling to private equity, Conor is now building Operator Equity and Entrepreneur Cooperative, empowering founders to scale and exit with purpose. Conor Tomkies shares how he leveraged strategic legal and operational efficiencies to save millions during acquisitions. He highlights his founder-first approach with Operator Equity, focused on scaling SaaS businesses using EOS, and discusses the startup shift from venture-backed moonshots to sustainable, profitable growth. ----------------------------------------------------- Raising capital? Get a list of vetted VCs for FREE here:⁠ https://web.thunder.vc/list-of-investors-vcs-for-founders⁠ Get the latest fundraising insights, news, and tips:⁠ https://blog.thunder.vc/funding-101⁠ Here's what you'll find in this episode: 00:00 Introduction 00:37 Dog genetics and the birth of Support Ninja 02:54 Bootstrapping vs. raising venture capital 05:30 Lessons from selling to private equity 10:14 Why EOS is a game-changer for scaling companies 18:34 Operator Equity’s focus on SaaS and ecosystem synergy 27:00 Common founder mistakes and the value of recurring revenue 30:45 The rise of moonshots and the future of venture capital ABOUT CONOR TOMKIES Conor Tomkies is a serial entrepreneur, investor, and post-exit founder with a passion for creating scalable businesses and empowering other entrepreneurs. He founded Support Ninja, a bootstrapped outsourcing company that scaled into a middle eight-figure success story and sold it to private equity. Now leading Operator Equity, Conor focuses on acquiring and scaling SaaS businesses using the Entrepreneurial Operating System (EOS), helping founders navigate successful exits with a streamlined 45-day process that prioritizes simplicity and a human touch. Conor is also the co-founder of Entrepreneur Cooperative (ECo) and host of the Made It Podcast. Through ECo, he has built a community where seasoned founders share experiences, collaborate, and gain insider strategies for navigating business sales and life beyond the exit. It’s the network every entrepreneur wishes they had when starting out, focused on meaningful growth, impactful exits, and supporting the next generation of founders. Connect with Conor: Website: operatorequity.com Entrepreneur Cooperative: entrepreneurcooperative.com X (formerly Twitter): @conortomkies_ ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: jason@thunder.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
    Show more Show less
    46 mins
  • EP 67: From Bootstrapping to $175M Exits with David Hauser

    EP 67: From Bootstrapping to $175M Exits with David Hauser
    Dec 19 2024

    Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders


    Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101

    -----------------------------------------------------

    What does it take to build, scale, and sell a business—and then do it all over again? David Hauser, the mastermind behind Grasshopper and Vanilla, has done just that. Starting with his very first pitch to his father for a Dell computer, David went on to raise nine figures for Return Path, bootstrap Grasshopper into a $175M success, and disrupt estate planning with Vanilla.


    But it hasn’t been all smooth sailing. In this episode, David opens up about the emotional aftermath of exiting a company, the identity struggles that follow, and how he found purpose by taking the leap into a new chapter. Now leading Durable Capital, David is focused on acquiring and scaling profitable companies while mentoring the next generation of founders.


    Here's what you'll find in this episode:

    • 00:00Trailer/ Introduction

    • 01:23 Early days: From a Dell computer to Return Path

    • 06:02 Bootstrapping Grasshopper to a $175M exit

    • 18:26 Vanilla and the decision to raise $42M in venture capital

    • 25:34 Navigating post-exit identity shifts and finding fulfillment

    • 39:00 Durable Capital: Buying and scaling profitable businesses

    • 41:28 Mentoring the next generation of founders


    ABOUT DAVID HAUSER

    David Hauser is a serial entrepreneur, investor, and speaker known for founding and scaling successful companies like Grasshopper (bootstrapped to $30M+ ARR, acquired by Citrix), Chargify (profitable, Mark Cuban-backed, acquired by Battery Ventures), and Vanilla (raised $42M from Venrock and Insight Partners). A founding member of National Entrepreneurs’ Day, he has also invested in over 50 startups, including Intercom and Unbounce. David’s insights have been featured in major outlets like CNN, Fox, and The Wall Street Journal, and he has spoken at renowned events such as SaaSFest and Big Omaha. Now leading Durable Capital from Las Vegas, he focuses on acquiring profitable businesses and mentoring the next generation of founders.


    Connect with David on:

    • Website: www.davidhauser.com


    ABOUT JASON

    Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.


    You can reach out to Jason through:

    Email: jason@thunder.vc

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


    ABOUT FUNDRAISING DEMYSTIFIED

    Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.

    Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
    Show more Show less
    48 mins
  • EP 66: How Patrick Butler Built 3 Wildly Different Businesses

    EP 66: How Patrick Butler Built 3 Wildly Different Businesses
    Dec 12 2024
    Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101 ----------------------------------------------------- What do a career coaching platform, a French-American football team, and a fraud prevention startup have in common? Meet Patrick Butler, the mind behind all three. Talk about a guy who doesn't do boring. One minute he's running a career coaching platform, the next he's starting a football team in Paris, and now he's crushing it with a fraud prevention startup called BizDefender. In this episode, Patrick shares the details of how he's jumped between totally different worlds. We're talking crazy fundraising tricks, buying up companies most people would run from, and basically rewriting the rulebook on how startups actually work. Seriously, who starts a pro football team as a side hustle? This guy. And he makes it sound like it's no big deal. It's the kind of story that makes you wonder: Are some people just wired differently? Patrick seems to turn wild ideas into businesses while most of us are still planning our next move. Want to hear about breaking every conventional rule in entrepreneurship? This is your episode. Here's what you'll find in this episode: 00:00 The Unlikely Pitch: Starting an American Football Team in France 00:48 Meet Patrick Butler: From Startup Success to Private Equity Exit 01:24 The Journey of Talent Inc.: From Struggles to Success 02:11 The Power of a Great Co-Founder: Meeting Jeff 03:29 Building Talent Inc.: The Resume Revolution 05:51 Scaling Up: Acquisitions and Growth Strategies 09:46 Navigating Fundraising: Debt, Equity, and Private Investors 19:59 Post-Exit Reflections: Life After Talent Inc. 21:30 A New Venture: Launching an American Football Team in Paris 25:51 Meeting a Nike Executive and Defining Our Vision 26:40 The Importance of a Brand Book 28:09 Convincing the French with American Football Culture 30:30 Economics of Starting a Football Team in France 31:51 Revenue Drivers and Merchandise 36:07 Launching BizDefender: A New Venture 41:13 Preventing Small Business Fraud with BizDefender 43:40 The Journey and Future of BizDefender 47:59 Final Thoughts and Contact Information ABOUT PATRICK BUTLER Patrick Butler is a serial entrepreneur, co-founder, and CEO of BizDefender, a first-of-its-kind fraud prevention tool for SMBs. His entrepreneurial achievements include leading Talent Inc. to a successful exit and co-founding a professional American football team in France. Patrick is passionate about creating impactful businesses while fostering innovation across industries. Connect with Patrick on: Website: www.pbutler.com Biz Defender: www.bizdefender.com ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: jason@thunder.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
    Show more Show less
    51 mins

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