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.

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

Is "solving big, obvious problems" a recipe for failure?

Peep Laja, founder of Wynter, joins us on Unf*ck My Startup to challenge classic business advice. We discuss why a small, profitable, bootstrapped company can be a bigger win for a founder than a VC-backed unicorn.


In this deep dive, we explore:

The VC Trap: Why a billion-dollar exit is an illusion and how VC-backed companies with "big, obvious" problems rarely succeed unless they have a massive war chest.

The "David" Playbook: How to win in a space that isn't a "mega urgent" problem. Peep shares his method for finding a niche where you can achieve

$10M ARR and freedom.

Message Market Fit: Before you write a single line of code, you need to know if your website copy will resonate with your ideal customer. Peep shares why a small sample size is enough to get 80% of the insights you need to get it right.

The Power of Bootstrapping: How to achieve generational wealth by focusing on profitability from day one, rather than diluting your equity for a massive outcome that may never come.

This is a must-watch for any founder who wants to build a business on their own terms and win the game for themselves, not for their investors.

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

This week on Unf*ck My Startup, we're joined by the team from Understory (Alex Fine, Chris Chambers, and Ali Yildirim) to dig into what’s really working in B2B SaaS advertising.


👉 Inside this episode:

-A behind-the-scenes look at how Understory runs ads for B2B companies

-A live walkthrough of RB2B’s campaigns in Miro

-Audience members jumping on stage to get real-time feedback on their ads & outreach

-Practical strategies you can use to improve targeting, creative, and performance


If you’re running ads for a SaaS startup—or want to see how top agencies think about paid media + outbound together—this one’s packed with tactical takeaways.

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