Founders: Are ya Feelin' the Boot?

The Relentless Pursuit of Winning Podcast

May 22 2024 • 40 mins

Navigating Startup Lifecycles - Lance Cottrell delves into the multifaceted journey of a startup, from the adrenaline-fueled inception to the strategic pivots required for growth. He offers a rich narrative that captures the essence of evolving from a technical founder to a visionary leader, the art of team and business development, and the critical moments that dictate a startup's direction. This episode is an invaluable compass for entrepreneurs at all stages, highlighting the resilience needed to navigate the startup lifecycle and the wisdom gained from embracing the full spectrum of a founder's role.


In this episode, Lance Cottrell, a former astrophysicist and founder of Anonymizer, shares his journey from academia to entrepreneurship. He discusses the challenges he faced as a technical founder and the importance of learning on the job. Lance emphasizes the need for technical founders to transition into the role of CEO and delegate responsibilities to others. He also provides valuable advice for startup founders, including the importance of understanding customer needs and focusing on the business side of the company. Lance's experience as an angel investor and mentor has given him unique insights into the startup ecosystem, which he shares through his podcast, Feel the Boot.


  • Transitioning from academia to entrepreneurship requires a willingness to learn on the job and adapt to new challenges.
  • Technical founders should focus on transitioning into the role of CEO and delegate responsibilities to others.
  • Understanding customer needs and focusing on the business side of the company are crucial for startup success.
  • Seeking advice and mentorship from experienced entrepreneurs can provide valuable insights and guidance.


  • 00:00 Introduction and Background
  • 04:01 Turning Theoretical Knowledge into Practical Knowledge
  • 06:18 Finding a Business Partner
  • 11:43 Transitioning Roles and Handing Over Responsibilities
  • 13:40 Transitioning from Founder to Advisor
  • 15:40 Getting Involved in Angel Investing
  • 21:50 Addressing Business Sense Gaps in Technical Founders
  • 29:25 Transitioning from Technical Founder to CEO
  • 32:05 Advice for Founders Who Prefer Technical Roles
  • 38:02 Resources for Startup Advice