How Adam Robinson bootstrapped Retention.com to $22M ARR, $1M ARR RB2B playbook & best way to build wealth as a founder (VC vs Bootstrap)

Hey everybody welcome back to the Product Market Fit Newsletter 🚀

My name is Guillermo Flor and I write this weekly newsletter to help founders, growth professionals and product people to grow & fund their companies.

In this Newsletter I want to share my latest conversation with Adam Robinson, founder and CEO of Retention.com & RB2B.

Adam Robinson Bootstrapped Retention.com to $22M ARR and made $1M ARR in several months after the launch of RB2B

But, before, and as always let’s play some music: Fatboy Slim's legendary DJ set on Brighton Beach 🔥

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The Early Days: From Wall Street to Entrepreneurship

Adam Robinson had worked at Lehman Brothers in Manhattan for 10 years until the company went bankrupted in 2008.

However, he had been intrigued about software and entrepreneurship for a long time,

His roommate in New York at the time, was working on Vimeo and that together with the dea of building something from scratch Adam decided to start his first company.

The Birth of Robly:

After the Lehman fallout, Adam decided to make the leap into tech.

That’s how Robly, an email marketing tool, was born.

Robly found some early success. Adam and his team managed to get it to $3 million in annual revenue, which is no small feat.

After hitting $3 million, Robly hit a growth ceiling. No matter what Adam and his team did, they couldn’t push past it.

This was a tough pill to swallow. Adam knew that to break through, he needed to find a way to differentiate Robly from the competition. But how?

Hitting the Wall and the Frustration:

Adam described this period as being "stuck." For three long years, Robly was plateaued at $3 million in ARR.

Imagine the frustration: you’ve built something successful, but you can’t seem to get it to the next level. You’re trying everything, but nothing works.

Adam was single, in his late 30s, living in Manhattan, and realizing that if he wanted to achieve his personal goals—like starting a family—he needed to build something bigger.

The Breakthrough: Retention.com

The breakthrough finally came when Adam stumbled upon the concept of email identity resolution.

This idea was radical. It involved capturing the email addresses of website visitors without them filling out a form—a technique that was not only possible but also legal in the U.S.

Realizing the potential of this new feature, Adam made a strategic decision.

Instead of keeping it as just a feature within Robly, he spun it out into a separate company—Retention.com.

The Growth Phase: Scaling to $22M ARR

Retention.com started growing with Facebook ads with a modest budget.

But unlike many startups that burn cash on ineffective ads, Adam’s ads were highly targeted.

He focused on high-value users—specifically e-commerce companies with large email lists that could benefit the most from Retention.com’s services.

What made these ads so effective was the pricing model.

Retention.com offered a range of plans from $9 to $5,000 per month.

While the majority of customers came in at the lower price point, the occasional $5,000 customer would more than pay off the ad spend.

This model allowed Adam to scale his ad spend without running into negative ROI.

Challenges with Churn:

Selling leads tends to be very high churn because there’s a lot of businesses that just can’t make leads work.

Other SaaS giants like Salesforce or Shopify, whose products act more like systems of record with much lower churn rates because they are deeply embedded into their customers’ operations.

Adam knew he had to address this issue if Retention.com was going to continue growing.

He realized that his product was most effective for large e-commerce companies that were already good at email marketing and could make the most out of the additional leads Retention.com provided.

So, he pivoted his focus to these high-value customers.

Retention.com grows to 21M ARR and Adam launches RB2B

Moving forward, Retention.com had a great growth, until a recent plateau at 21M ARR.

And then is when Adam decided to launch RB2B, the Retention.com solution for B2B.

Premium:

1. How RB2B grew to $1M ARR in 16 weeks

2. The big Debate: Bootstrap vs. Raise Capital. Which is the best route to build wealth as a founder

How RB2B grew to $1M ARR in 16 weeks

RB2B hit $0-1m in 16 weeks.

You can access RB2B realtime metrics here

This is the 7-step playbook that made RB2B an 8-figure product with a tiny team 👇