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

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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:

• 00:00Trailer/ 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.

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

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Think debt is a trap? Think again. Learn how the right kind of debt can fuel your growth without sacrificing control of your startup. In this insightful episode, Jason Kirby welcomes Kyle Rector, co-founder and president of Boundless, to shed light on an often-overlooked aspect of startup funding: debt financing. If equity raises are the headlines, debt is the subplot that drives growth for countless businesses—but only if founders understand how to wield it wisely.

Kyle shares hard-earned wisdom from a decade of navigating the debt financing space, offering practical advice for founders at all stages. Kyle walks us through the spectrum of non-dilutive funding options, from the basics of debt vs. equity to the complexities of venture debt, revenue-based financing, and more. Whether you’re looking to extend runway, fuel expansion, or build sustainable operations, this episode equips you with the knowledge to make informed capital decisions.

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

• 00:00 Introduction to Debt Financing

• 00:08 Meet Kyle Rector: Debt Financing Expert

• 00:55 Understanding Debt vs Equity

• 03:41 Types of Debt for Businesses

• 08:27 Term Loans Explained

• 09:59 Lines of Credit: Flexible Financing

• 11:42 Secured vs Unsecured Financing

• 16:48 Venture Debt: A Strategic Option

• 22:23 Revenue-Based Financing: Pros and Cons

• 29:49 Exploring Different Types of Debt Financing

• 30:07 Valuing Contracts and Lines of Credit

• 32:56 Preparing to Secure Debt: Key Considerations

• 37:14 Understanding Debt Service Coverage Ratio (DSCR)

• 40:35 Benchmarking Debt Options for Different Business Profiles

• 51:47 Building Relationships and Trust with Lenders

• 54:05 Conclusion and Final Thoughts

  
  

ABOUT KYLE RECTOR

Kyle Rector is the co-founder and president of Boundless, a capital marketplace connecting businesses with lenders through tailored solutions. With over 10 years of experience in debt financing, Kyle has facilitated billions in capital requests, spanning industries and geographies. His mission with Boundless is to simplify the capital application process, enabling founders to focus on scaling their businesses.

Connect with Kyle on:

• Webiste: www.getboundless.ai

  
  

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.