Living the Dream at $35M ARR, 32 People | Adam Robinson

Resources and Links

• Retention.com: retention.com
• RB2B: rb2b.com
• MoltSets: moltsets.com
• Adam on LinkedIn: linkedin.com/in/retentionadam
• Adam's personal site: theadamrobinson.com
• Adam's newsletter: newsletter.rb2b.com
• Book mentioned: Delivering Happiness by Tony Hsieh
• Book mentioned: Rework and Remote by Jason Fried
• Blog mentioned: Mr. Money Mustache

Key Timestamps

(01:38) The neighborhood doctor who defined success
(04:18) The phrase that changed how he saw work
(07:19) Talking his way into Lehman Brothers
(10:22) Watching his roommates build Vimeo
(11:50) Why he finally left finance behind
(23:39) Why the first seven years were terrible
(25:30) Running a boiler room from his apartment
(26:17) The loophole that built his first company
(27:52) Brute forcing his way to revenue
(30:56) The layoff he still calls the worst
(32:29) How Retention.com was actually born
(34:41) Was selling Robly his first real success?
(35:37) $35 million ARR with 32 people
(36:44) How his relationship with money began
(37:41) The identity crisis he calls indescribable
(39:41) When money stopped being the point
(41:35) No longer attached to a number
(42:00) Moving to Aspen and living without lack
(46:51) Why he's starting a fourth company
(52:20) How he defines success today

Episode Summary

Adam Robinson grew up in Houston in the kind of suburb where the coolest dad on the block wasn't a businessman, it was the neighborhood orthopedic surgeon who clearly loved what he did, drove a nice car, and had what Adam calls the vibe. That image stuck with him more than any career advice ever did. His own father was an oil trader who worked mainly to pay for his kids' college and quit the day that job was done, which planted an early idea in Adam's head: work was something you did for money, until it wasn't necessary anymore.

Adam followed a version of his father's path anyway, talking his way into a derivatives trading job at Lehman Brothers despite having no real qualifications for it. He spent a decade trading credit default swaps, making more money in his twenties than he ever expected, while watching his old roommates build what would become Vimeo out of the apartment next door. Watching people who clearly loved their work planted the idea that he wanted that too, eventually convincing him to leave finance behind.

What followed wasn't the easier life he expected. His first company, Robly, grew off the back of a data loophole in a competitor's website, and for a while Adam ran what he calls a boiler room, cold calling leads out of his own apartment to force revenue. The company stalled at $3 million ARR for two and a half years. He had to deliver an in-person mass layoff, twice, years apart, calling an entire room of employees together to tell them they no longer had jobs. Around that same period, after a breakup and a failed attempt to return to trading, Adam went through what he now describes as the closest he's come to depression, an identity crisis so disorienting that a friend once told him to just make it through the day.

Robly's stall eventually led to something better. A feature nobody wanted the rest of the product for became GetEmails, and later Retention.com, a business Adam says felt like the first thing he'd actually built rather than stumbled into. Today Retention.com runs at $35 million ARR with just 32 people. Adam is now building a fourth company, MoltSets, and says his relationship with money has settled into something closer to equilibrium: not chasing a number anymore, just making sure the business keeps growing and he still has the energy to keep going.

Connect with Melissa

• Connect with Melissa at melissakwan.com and subscribe to 'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow Melissa Kwan on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Find her on @themelissakwan on Instagram, TikTok, Twitter and YouTube where she shares short videos of business advice and other truth-bomb sound bites.