From Wall Street to scaling SaaS companies with no outside capital — Adam Robinson shows us how it’s done (and the brutal lessons learned along the way).
On today’s episode of the [A] Growth Ventures Podcast, Hamlet Azarian sits down with Adam Robinson, founder of Robly Email Marketing, Retention.com, and RB2B, to uncover the true story behind building businesses the hard way — without venture money, without perfect plans, and without hiding the painful realities of entrepreneurship.
Adam’s story isn’t just about wins; it’s about resilience, reinvention, and radical transparency.
This is a playbook you won’t find on most startup podcasts.
What We Explored with Adam Robinson
Wall Street Origins: Chasing Money, Learning Realities
Adam shares how surviving Lehman Brothers’ collapse shaped his early hunger for financial freedom — and how he realized money alone wasn’t the goal.
Roommates with Vimeo: A Front-Row Seat to the Tech Boom
Living with Vimeo’s founding team gave Adam a rare glimpse into the wild, creative side of entrepreneurship — and planted a seed he couldn’t ignore.
The Bootstrap Journey: Robly and the Power of a Single Tip
Robly wasn’t a polished tech fairytale. Adam reveals how a scrappy cold-calling hack led to 5,000 customers and funded his education in real business building.
The Breakthrough (and the Bottom): How Retention.com Found Its True Product
From failed launches to near rock-bottom moments at trade shows, Adam walks us through how brutal honesty and listening to customers birthed Retention.com’s runaway success.
Scaling Without Venture Capital: Growth, Profitability, and Painful Lessons
We dig into how Adam grew Retention.com to $22M ARR with just 30 people — and why not all growth is glamorous behind the scenes.
The New Playbook: Building RB2B and the Art of Radical Content
Discover how Adam’s shift to building in public on LinkedIn — sharing wins and brutal failures — became his most powerful growth lever yet.
Why Some SaaS Companies Can’t Become Unicorns (and Why That’s Okay)
Adam breaks down the uncomfortable truth about churn-heavy SaaS models — and why focusing on cash flow, not hype, is his next big move.
Key Takeaways
- 01:00 — Early career on Wall Street and lessons from collapse
- 05:00 — Watching Vimeo grow: The creative itch begins
- 15:00 — How Robly survived (barely) through smart targeting
- 24:00 — The rock bottom trade show moment that changed everything
- 35:00 — Retention.com’s explosive growth — and hidden challenges
- 44:00 — Building trust in public: how radical honesty fuels real traction
- 52:00 — The next frontier: combining SaaS + education for sustainable growth
Final Thoughts
Adam Robinson reminds us that entrepreneurship isn’t about polishing your story — it’s about surviving long enough to build a real one.
It’s messy. It’s painful. It’s worth it.
If you’re tired of filtered startup stories and want the raw blueprint of what it really takes to scale a business from scratch, this episode is a must-listen.
Connect with Adam Robinson on LinkedIn to follow his unfiltered entrepreneurial journey — and learn more about Retention.com and RB2B through the links in the show notes.
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