From Wall Street Burnout to $25M ARR:
Adam Robinson on Building

Listen on YouTube, Spotify, or on Apple Podcasts

In this episode of Investing on Purpose, host JP Newman sits down with Adam Robinson, founder of Retention.com, to explore his remarkable transition from high-stakes Wall Street trading to building a purpose-driven, word-of-mouth business that scaled to $25M in ARR—bootstrapped.

Key Takeaways from the Episode

1. The Wall Street Grind vs. Entrepreneurial Freedom
  • Adam spent a decade in the cutthroat world of credit default swaps at Lehman Brothers, where self-worth was tied to profit margins.
  • After the 2008 financial crisis and a career low, he faced an identity crisis—leading him to question the emptiness of chasing money without purpose.
2. The Spiritual Awakening
  • Tony Hsieh’s Delivering Happiness sparked a revelation: true fulfillment comes from purpose, not paychecks.
  • Adam realized businesses thrive when they create environments where people want to work, not just have to.
3. The Hard Truth About Product-Market Fit
  • His first startup struggled because it couldn’t compete with giants like Mailchimp. The lesson?
    Without a truly unique, word-of-mouth-worthy product, growth is an uphill battle.
  • The breakthrough came with Retention.com, which solved an unsolved problem: identifying anonymous website visitors.
4. LinkedIn as a Canvas for Authenticity
  • Adam’s viral LinkedIn presence (100K+ followers) thrives on radical authenticity—sharing failures, raw stories, and unfiltered insights.
  • His mantra: “Be the most human version of yourself.” AI can’t replicate genuine connection.
5. Advice for Stuck Entrepreneurs
  • Stop pushing a weak product. Focus on solving an unmet need so compelling that customers refer you.
  • If growth stalls, pivot boldly (like his office-mates who pivoted to Jasper AI and hit $50M ARR in 12 months).
6. The Higher Purpose
  • Beyond revenue, Adam’s mission is to elevate others—through his podcast (Unfuck Your Startup), mentorship, and fostering a culture where employees feel valued.
  • As he puts it: “Success is creating something people love so much, they can’t stop talking about it.“

Final Thought

Entrepreneurship isn’t just about hustle—it’s about artistry, resilience, and serving a need so well that your product sells itself. Adam’s journey proves that when you align purpose with innovation, even the steepest setbacks become stepping stones.

Listen to the full episode for more on mindset shifts, LinkedIn growth hacks, and why vulnerability is the ultimate competitive edge.