Bootstrapping to Exit, First Principles Thinking, Product Simplicity, and Mentoring the Next Generation w/ Jason Seats, Co-Founder of Slicehost & fmr CIO of Techstars

On this episode of Outsider Inc., host Ian Hathaway sits down with Jason Seats, Co-Founder of Slicehost, former Chief Investment Officer of Techstars, and a pioneer in the startup and cloud computing worlds. Jason details his journey from co-founding the game-changing cloud infrastructure company, Slicehost, to mentoring and investing in early-stage startups through Techstars. They discuss the importance of simplicity, first principles, and the value of building with trusted partners. Jason shares insights on navigating acquisitions, the challenges of integrating into a large company, and the evolution of the pre-seed and seed investment landscape. His story is a testament to succeeding as an outsider and the power of trusting relationships in entrepreneurship.

 

Show Notes:

 

(02:12) The Birth of Slicehost: Simplicity and Innovationt

(06:32) The Importance of Partnership and Family Support

(10:40) Navigating Early Challenges and Learning from First Principles

(13:55) Scaling Up: Hiring and Community Building

(18:31) Unexpected Acquisition: The Rackspace Story

(24:50) Transition to Rackspace: New Beginnings in San Antonio

(28:29) Transition to Techstars Cloud

(32:25) Launching Techstars in San Antonio

(35:47) Evaluating Startups and Investments

(41:58) Macro View on Venture Capital

(49:37) Life After Techstars

(51:03) Beyond the Bio with Jason Seats

 

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guest: Jason Seats - Co-Founder of Slicehost & former Chief Investment Officer of Techstars

 

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.

 

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