Always Be Testing, Episode #108

“Lessons from a founder who built a lean, profitable SaaS—and still hit a growth ceiling”
Guest: Adam Robinson, CEO of Retention.com
Host: Tye DeGrange
Date: November 11, 2025

Episode Overview

In this episode, Tye DeGrange welcomes Adam Robinson, founder and CEO of retention.com, to dive deep into the nuanced journey of building and growing a lean, highly profitable SaaS business. Adam shares the hard-won lessons from a decade-long entrepreneurial ride, including how he built a company that hit impressive financial goals without compromising on work-life balance, managed the evolving challenges of product innovation, and navigated both B2B and consumer SaaS markets. The conversation is candid, practical, and rich with tactical advice for founders, operators, and marketers interested in data-driven growth.

Key Discussion Points and Insights

1. Adam’s Entrepreneurial Backstory

[00:43–07:01]

• Adam recounts his transition from finance (credit default swap trader at Lehman Brothers until the financial crisis) to tech entrepreneurship, inspired by friends who created Vimeo.
• First SaaS venture: an email newsletter app launched in January 2014, which plateaued at $3M ARR using inventive, sometimes “scrappy” tactics (like crawling contact data).
• Lessons from the early years: “The actual things that I’m doing every day have changed so much year to year that it’s just wild. It’s like not the same job I had 10 years ago.” (Adam, 01:27)

2. The Growth Ceiling & Embracing Lean Principles

[07:03–09:44]

• Adam details how he transformed the business by focusing on cutting costs, burn, and complexity, arriving at an ultra-lean operation: 40 people, ~$30M ARR.
• Reflections on achieving major financial goals: “I thought literally written down my dream… was 2 million a month MRR. And if we could get there, I would have no other problems. I would be satisfied. I would never ask for another thing in my life.” (Adam, 07:44)
• Realization after reaching financial targets: Topline growth slows, satisfaction becomes a moving target, and value is more than just exit numbers.

3. The Trap of “The Number”

[10:05–11:39]

• Cautionary tales from a Vimeo founder: “He had a number and then he had this perfect business, got offered a price that got him above his number… [he says] it was the wrong goal… If he just would have let it happen over the last seven years, he would have just been much more energized by his life every day.” (Adam, 10:20)
• Emphasis on the value of holding onto a good business and not being seduced by exit figures.

4. Lifestyle Design: Running a Business to Live, Not Living to Run a Business

[11:39–13:49]

• Adam describes his decision to relocate to Aspen for family and lifestyle, framing his business success as an enabler of quality of life.
  • “I want to just set my life up to just do this for a few more decades.” (Adam, 12:06)
• Discussion on the value of “fishing on the beach” type philosophies, and how entrepreneurship can create that freedom.

5. Navigating B2B and Consumer Sides of SaaS

[13:32–17:18]

• Adam is candid about his challenges in splitting attention between retention.com’s e-commerce and B2B products.
  • “Well, not well, to be perfectly honest.” (Adam, 13:49)
• Insights on building a personal founder brand, transparency (posting P&Ls publicly), and the differing content needs of B2B vs. B2C SaaS.
  • “It became clear… there was some author, audience, platform fit when I wrote about the B2B stuff that it did not... on the B2C.” (Adam, 15:12)

6. Product-Market Fit, Churn, and Competitive Moats

[17:18–20:33]

• Describes distinct market dynamics:
  • E-comm SaaS tends to be sticky as it’s intertwined with the customer’s business (like Klaviyo).
  • B2B data products are less sticky, with higher churn and easier switching.
• Importance of product differentiation: “Nobody can run this business like I can run it. And unless you could, you wouldn’t be in the market which is kind of what happened.” (Adam, 19:57)
• RB2B’s lean operation: ~$6.5M ARR with only three full-time employees; competitive edge is both product and personal founder brand moats.

7. Product Innovation: Staying Ahead of the Curve

[20:37–24:42]

• Adam previews a new e-commerce product inspired by B2B “clay” tables (data enrichment, AI-driven micro-segmentation, and personalization at scale).
  • “If you knew the persona of the person… you could create 300 variants of copy. That’s very easy to do with something like a clay table and OpenAI and that will work.” (Adam, 22:38)
• The unending demand for innovation: “We cannot stop innovating ever, anywhere, or these businesses will die.” (Adam, 26:10)

8. Founder Brand as Growth Lever

[29:01–32:00]

• Adam attributes RB2B’s entire success to his large personal brand and content—1M LinkedIn impressions/month leading to 30,000 unique web visits without paid campaigns.
• The challenge: founder’s audience is much broader than the paying customer base—how to create or white-label complementary products for a wider audience.
• Wrestling with the urge to chase new ideas versus maintaining differentiation.

9. Looking Ahead: Relentless Growth, Innovation, and Personal Balance

[26:10–27:46]

• 2026 focus: relentless product innovation, hiring for product leadership, and listening keenly for signals from the market.
  • “It’s just like you are either innovating or you are dying a slow death.” (Adam, 26:25)
• Adam highlights the importance of having top-tier product leadership as a competitive advantage.

Notable Quotes & Memorable Moments

• On building and iteratively changing as a founder:

  “The actual things that I’m doing every day have changed so much year to year that it’s just wild.” (Adam, 01:27)

• On chasing and reaching ambitious goals:

  “I wrote the goal [of $2M MRR] when I was 37 and I did it on my like 44th or something… all of a sudden like… I’m playing with the house’s money.” (Adam, 08:13)

• On the perils of selling too soon:

  “He had a number… he got above his number. And he’s like, ‘it was the wrong goal.’” (Adam, 10:20)

• On family and lifestyle design:

  “I’m bringing my 3 year old and 1 year old to Aspen… I want to just set my life up to just do this for a few more decades.” (Adam, 11:40 & 12:06)

• On product differentiation:

  “Nobody can run this business like I can run it. And unless you could, you wouldn’t be in the market.” (Adam, 19:57)

• On continuous innovation:

  “We cannot stop innovating ever, anywhere, or these businesses will die.” (Adam, 26:10)

• On leveraging a personal founder brand:

  “My founder brand is entirely responsible for the success of RB2B.” (Adam, 30:07)

• On juggling kids, work, and personal mission:

  “Once I had kids, it was just like, I got kids, I got work. I’m trying to stay in shape. I’m trying to see some friends... but that’s it. I have a simple life in that regard.” (Adam, 33:52)

Timestamps for Key Segments

• Intro & Adam’s journey: 00:43–04:24
• Early SaaS growth tactics: 04:24–07:01
• Profitability & hitting the growth ceiling: 07:03–09:44
• Reflections on exit numbers & fulfillment: 10:05–11:39
• Lifestyle & moving to Aspen: 11:39–13:49
• B2B vs. B2C business tensions: 13:32–17:18
• Product-market fit, churn, and moats: 17:18–20:33
• Personalization and tech trends: 20:37–24:42
• Innovation imperative: 26:10–27:46
• Founder brand and growth: 29:01–32:00
• Family and purposeful living: 33:22–34:29

Closing Thoughts

This episode provides unusually candid insight into the journey of building a profitable, bootstrapped SaaS company, the ongoing challenge of innovation, and the personal side of entrepreneurship. Adam’s practical quips, openness about missteps, and emphasis on enjoying the journey—not just the destination—make this a must-listen for anyone interested in SaaS growth, founder life, or data-driven marketing.

For more on Adam and his work:
Follow Adam Robinson on LinkedIn, check out retention.com, and keep an ear out for innovation announcements in the Shopify and B2B SaaS landscape.