Outsider Inc. Bootstrapping to Exit, First Principles Thinking, Product Simplicity, and Mentoring the Next Generation w/ Jason Seats, Co-Founder of Slicehost & fmr CIO of Techstars
May 14, 2025
In a fascinating conversation, Jason Seats, Co-Founder of Slicehost and former CIO of Techstars, shares his entrepreneurial journey and the essence of simplicity in product design. He reflects on the unexpected acquisition by Rackspace and the challenges of integrating into a larger company. Jason emphasizes the importance of trust and partnership in startups, and the shift in the venture capital landscape over time. His insights into mentoring the next generation of entrepreneurs highlight the value of community and resilience in their journeys.
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Simplicity As A Winning Strategy
- Slicehost won because the product made provisioning servers instant and easy.
- Jason Seats said customers could get a server and first win within 45 seconds.
Rails Sparked The Idea
- Matt's frustration hosting Rails apps inspired Slicehost's idea.
- Jason Seats joined after a lunch where Matt sketched automating virtual servers.
Spousal Support Enabled Risk
- Amanda's instant support convinced Jason to start the business.
- That family backing made them naive enough to commit fully.