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 y...
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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 y...
Why Your Outbound Sucks (and How to Fix It) with Kyle Coleman
Unf*ck My Startup
55 minutes
2 months ago
Why Your Outbound Sucks (and How to Fix It) with Kyle Coleman
In this episode of Unf*ck My Startup, Adam Robinson and Pete Crowley welcome Kyle Coleman, Global VP of Marketing at ClickUp, to dive into why outbound isn’t dead—but your outdated playbook is. We cover: -Why most outbound fails in 2025 -How buyer behavior has shifted -Real talk on cold outreach (and how to actually get responses) -The “Pitch Slap” live segment where founders try to out-book last week’s record of 35 demos -How Adam’s team is running their entire business with AI for 7 days ...
Unf*ck My Startup
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 y...
