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and Pete Crowley welcome Kyle Coleman, Global VP of Marketing at ClickUp, to dive into why outbound isn’t dead—but your outdated playbook is.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 straight

Packed with tactical takeaways, hilarious moments, and some brutally honest sales talk, this episode is a must-watch for founders, marketers, and anyone tired of stale sales strategies.

📌 Follow Kyle on LinkedIn: https://www.linkedin.com/in/kyletcoleman/
📌 Get Adam’s AI playbook: https://www.rb2b.com/ai

Find out more
https://www.linkedin.com/in/retentionadam/
https://www.youtube.com/@retentionadam
https://www.rb2b.com/