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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:

• 00:00 Trailer/ 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.