The Unconventional Path to $100K MRR

Forget the traditional stair-step approach. Here's my unconventional path to $260K MRR.

Most bootstrappers follow Rob Walling's methodical stair-step: build small products, repeat until you own your time, then tackle SaaS.

I took a different route.

Here's my Modified Stair-Step Approach:

Step 1: Build a bootstrapped SaaS (and fail) Body Boss was supposed to revolutionize fitness. Instead, it taught us so much that my co-founder Daryl wrote a book about our failure: "Postmortem of a Failed Startup: Lessons for Success."

Step 2: Join a funded startup → become CTO → acquire for $1 Joined Kevy as an engineer. Six months later, I was CTO. When the CEO left and the investor wanted to shut down, I made an unconventional proposal: "I want to do this, but without you."

He sold me the entire company for one dollar.

Step 3: Run a lifestyle business → sell for life-changing money Grew Kevy to $250K ARR as a solopreneur. The recurring revenue was great - it provided stability for my family. But doing everything from sales to support eventually wore me down.

I sold it while signing papers in the hospital after my daughter was born. Priorities became crystal clear.

Step 4: Take time off and recover Joined Google. Realized how burned out I actually was. Sometimes the best business move is stepping away.

Step 5: Find the perfect co-founder and build the "impossible" Met Alex on IndieHackers. He already had a language learning marketplace running, which made the "impossible" feel possible.

Still, conventional wisdom screamed: "Don't build 2-sided marketplaces. Too hard. Pick a side."

We ignored it. Built LanguaTalk anyway while I worked at Google.

Three years later: $8.19M in gross volume. But the real surprise? The SaaS app we built on top — Langua — became our rocket ship.

I've come full circle. We're now north of $260K MRR just on the SaaS side.

The key -> Your path doesn't have to be linear.

Failure, recovery, and unconventional moves can be your biggest accelerators.

What's been your most unconventional career move that paid off?

Originally posted on LinkedIn on June 18, 2025