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/

On this episode of Unf*ck My Startup, founders Adam Robinson (RB2B) and Max Greenwald (Warmly) go head-to-head, debating the two most popular startup paths: bootstrapping vs. VC funding. They've both built multi-million dollar companies in the same market, but with completely different approaches.

In this debate, you'll learn:

The Numbers: RB2B's $5.8M ARR with a team of 3 vs. Warmly's $4.4M ARR with 55 employees.

The Philosophy: Why Adam chose to bootstrap for freedom and profitability, while Max embraced VC-funding to scale and learn.

The Reality: The psychological toll of each path, and why they're no longer direct competitors.

This is a must-watch for any founder weighing their options.

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

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/

In this episode of UnF*ck My Startup, we sit down with Pukar Hamal, the founder of SecurityPal, who has defied the conventional VC playbook. Pukar shares the story of his last startup, where a mind-numbing 200-question security questionnaire almost killed a game-changing deal. That frustration led him to create SecurityPal, a company that literally does the work for you by having a team of 250 experts and AI to complete these questionnaires. He raised a $20M seed round from one of the best firms in the world and then did what every VC fears most: he became profitable.


SecurityPal offers a free trust center at freetrustcenter.com to help companies communicate their security posture easily and deflect questionnaires.


Links:

Security PAL: https://www.securitypalhq.com/

Pukar Hamal's LinkedIn: https://www.linkedin.com/in/pukarhamal/

Adam Robinson's LinkedIn: https://www.linkedin.com/in/retentionadam/

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 sat down with Irina Novoselsky, the CEO of Hootsuite, to discuss her unique approach to personal branding and social media. Irina shares her journey from a Ukrainian refugee to leading a 1,500-person company, and why authentic, first-person content is a non-negotiable for modern leaders.

If you've ever felt held back by the fear of "messing up" on social media or struggled with a blank page, this episode is for you.


In this episode, you’ll learn:

The Power of Data: The math behind social media, including a staggering statistic that 77% of buyers look at a company's and its executives' social media content.

The Gen Z Factor: Why the new generation of buyers, Gen Z, are forgoing Google and turning to social media to research purchases, and their double likelihood to buy from brands they follow.

From Text to Video: How Irina overcame her struggles with writing and embraced video, finding it a more natural and authentic way to communicate with her audience.

The "Vibe" of the Algo: Insights from a LinkedIn executive on what the algorithm loves (and hates), and how to structure your posts for maximum engagement.

Strategic Engagement: The 70/30 rule for social media: spending 70% of your time commenting and 30% on self-posting to boost your profile's distribution.

The 9 to 1 Ratio: A powerful principle for building an audience by giving them valuable, educational content 9 times before asking for something in return.

The CEO's Playbook: Why announcing product features and awards is a "buzzkill" and how to instead turn your company's journey into an unfolding drama that your audience can connect with.

Get ready to unf*ck your social strategy and leverage your personal brand to drive real business results!


👇
Follow Irina → / irina-novoselsky
Check out Hootsuite → https://www.hootsuite.com/

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, Adam Robinson and Pete Crowley welcome Taylor Haren, the mastermind behind sending millions of emails a month for companies like Fixer and RB2B!

If you're wondering how to scale your cold email outreach, navigate the ever-changing spam filters, and get real results, this episode is for you.


Inside this episode:

-Infrastructure for Scale: Learn how to send 5,000 emails a day (and plan for 15,000) using 250 email accounts across 125 domains, and what happens when you push to 8.5 million emails a month.

-The Truth About Warmup: Discover why "warmup" is more about diluting your complaint pool than mimicking human activity, and the surprising results of A/B tests on new domains.

-Finding Your Leads: Taylor reveals his multi-vendor approach to building massive and effective prospect lists, including Apollo, Bounceband, Lead Magic, and Wizza.

-Cracking the Copy Code: Understand why "copy is king" and how even subtle changes (like "AI" vs. "ai") can drastically affect deliverability and reply rates.

-Beyond the Sequence: Challenge traditional notions of multi-touchpoint sequences and learn why a single, highly relevant email can be more effective.

-Get ready to unf*ck your cold email strategy and scale your outreach like never before!

👇
Follow Taylor → https://www.linkedin.com/in/taylorharen/
Check out Sales Automation Systems → https://www.salesautomation.systems/

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