#276 What if the one strategy that built your business suddenly stopped working? Would you know how to pivot — or would you crash and burn? In this episode hosted by Kirsten Tyrrel, we sit down with Adam Robinson, former Wall Street trader turned successful entrepreneur. After the 2008 financial crash upended his career at Lehman Brothers, Adam took a leap into the unpredictable world of online business. He shares his rollercoaster journey — facing failures, finding product-market fit, and ultimately building Retention.com into a multi-million dollar company. We dive deep into the importance of resilience, why cold email still works (when done right), and the hard truths about scaling a startup. If you're an entrepreneur navigating the early stages of business, this episode is packed with invaluable lessons you won’t want to miss!

What we discuss with Adam:

+ From Wall Street to startups – Adam’s transition after the 2008 crash

+ Early business struggles – Lessons from his first failed venture

+ Finding product-market fit – How one feature changed everything

+ Cold email & ethics – Debunking myths about outreach and compliance

+ Breaking revenue plateaus – The pivot that unlocked growth

+ Scaling a SaaS company – Growing Retention.com to $25M ARR

+ Behavioral email marketing – Why targeted emails outperform blasts

+ Common founder mistakes – Focusing on the wrong things early on

+ The right way to start – Talk to customers, validate, then scale

+ Grit & resilience – The real key to long-term success

Thank you, Adam!

Check out Retention.com at Retention.com.

Check out RB2B at RB2B.com.

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