Bootstrapping vs. VC with CollegeHumor and Vimeo Founder Josh Abramson

Entrepreneurial legend and founder of CollegeHumor, Vimeo, and TeePublic, Josh Abramson, joins Adam Robinson on this episode of Unfuck My Startup. Josh shares his journey from building and selling CollegeHumor to IAC, to buying back Busted Tees and launching TeePublic.

In this episode, you’ll hear Josh and Adam discuss the pros and cons of bootstrapping versus raising venture capital. Josh gets candid about the experience of selling a business and the importance of finding purpose in your work outside of financial gain. He also shares incredible stories, like the time a friend's company turned down an $800 million acquisition offer only to be worth zero 18 months later.


Key topics include:

The Bootstrapping Mindset: Why building a profitable, cash-flowing business can be more rewarding than chasing a billion-dollar valuation

The Dark Side of Venture Capital: How VC and board goals can sometimes be at odds with a founder's best interests

The "What's Next?" Problem: The unexpected emotional challenges that come with a life-changing financial exit

The Power of Derivative Startups: How building on an existing business or team can be an easier path than starting from absolute zero


This episode is a must-watch for any founder or entrepreneur who wants to build a sustainable, fulfilling business on their own terms.

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