What do you do when your “successful” SaaS hits $403K MRR and you feel like you’re failing?
Most founders would kill for that number.
Groove has been profitable for years. Bootstrapped with no investor pressure. Complete “freedom.”
But here’s what I learned about reaching steady profitability:
Eventually, steady starts to feel heavy. When I opened Stripe for the twelfth month straight and saw that same flat line at $403K, I didn’t feel successful or free, I actually felt trapped.
Today, I’m going to share why I’m betting everything on rebuilding our entire business from the ground up, and the 3 decisions that led to unbundling Groove into a holdco I’m calling OptimizeCX.
Let’s dive in.
The moment steady became suffocating.
For ten years, Groove grew slowly but surely from $25K to $403K MRR at 60% EBITDA.
Every month, I’d check our numbers expecting growth.
Instead, I got the same flat line. $403,000. Again. And again.
That graph wasn’t moving up or down, just sideways into infinity.
But the real wake-up call came from our codebase.
Ten years of legacy code meant every small feature felt like a major rebuild. What used to take days had started to take weeks. Our roadmap became a wish list because we were drowning in technical debt.
That’s when it hit me:
Groove had shifted from build mode to maintenance mode.
500 customer conversations later…
Instead of panicking completely, I went back to the source.
I spent fifteen months talking with more than 500 customers and founders about their biggest customer experience pain points.
Their feedback was brutally clear:
- Tier 1 tickets were burning out support teams
- Knowledge bases were outdated the moment they were published
- All-in-one tools solved everything halfway but nothing well
These were massive complaints and expensive problems that AI could actually solve. The clarity gave me direction I hadn’t felt in years.
The problems were obvious, and I thought the opportunity was too.
I started to feel like the biggest risk for Groove was standing still.
The big bet that terrified my team (and me).
Some of the team thought I was crazy when I announced we were unbundling Groove to build multiple new AI-powered products.
Why risk what was working?
Because I realized “working” was really “barely surviving.”
We’re expanding Groove into OptimizeCX:
A family of focused products designed for the AI-powered future of customer experience:
- InstantDocs (launching November 12): The first AI-powered knowledge base that writes itself and looks beautiful
- Helply (launching October 27): AI support agents that cut ticket volume by 50%
- Groove (rebuilding 2026): A lean, AI-powered shared inbox for modern CX teams
Each product stands alone, but together they form a modular ecosystem that helps companies deliver incredible support without bloat.
We’ve already seen Helply users cut ticket volume in half while raising CSAT scores.
The north star is building tools that solve real problems with technology that actually works, while keeping each solution focused and “fluff-free.”
Why bootstrapped founders can build world-class products.
I’d be lying if I said I never noticed the flashier, funded startups getting all the attention.
YC badges. TechCrunch headlines. $50M Series A announcements.
Groove has always been profitable but quiet.
That’s changing.
I want to prove that bootstrapped founders can build products that aren’t just profitable, but world-class.
We’re aiming to become the #1 product of the year on Product Hunt. We’re scaling three startups simultaneously using the EOS system (more on this is future newsletters).
And we’re documenting every test, launch, and experiment in real time.
Groove gave me freedom, but I feel like OptimizeCX is giving me a renewed sense of purpose and excitement about entrepreneurship.
Honestly: the feeling of doubt is harder than the rebuild.
The biggest challenge hasn’t been technical or financial.
It was wondering how our loyal Groove customers would react.
Would they think we were abandoning them?
Would they lose trust in a company that was suddenly betting everything on something new?
Here’s what I’ve learned:
Customers want you to build solutions that matter. And sometimes that means taking risks that feel uncomfortable.
We’re not abandoning Groove, we’re using its solid foundation to build what’s next, faster and smarter.
I’ve never been more excited about what’s next.
Until next time,