The Origin Story (how Zero to $10m came to be)
I never planned on becoming a founder. I just hated wasting time.
In 2006, I was doing freelance work for financial advisors and saw the same problem everywhere. Their client data lived in clunky spreadsheets. Notes were scattered. Follow-ups got missed. I didn’t know what “product-market fit” meant at the time, but I knew these people were drowning in mess—and they’d pay to clean it up.
So I built Upswing CRM.
No funding. No cofounders. Just me trying to solve a real problem. It was rough. It barely worked. But it was mine.
That project gave me a taste. Not just of building software, but of doing the research, getting in the weeds, talking to customers, and fixing things in real time. I was hooked.
Three years later, I went bigger.
In 2009, I launched Bantam Live. We folded Upswing into it and doubled down on a new idea: CRM meets social media.
At the time, Facebook and Twitter were exploding. Everyone wanted to know how to bring social into the sales process. So I cold-called and interviewed over 100 potential customers before we wrote a single line of code.
We weren’t guessing. We were listening. And it worked.
In 2011, Constant Contact acquired Bantam Live for $15 million.
It was the first real win of my career. I thought I’d feel unstoppable. Instead, I felt restless.
Success made me want to build again—but this time, I wanted to do it my way.
That’s how Groove started.
The Frustration That Sparked Groove
Right after the Bantam Live sale closed, I took a breath.
Then I wrote a check.
Fifty thousand dollars. My own money. No investors. No safety net. I wanted to build something I needed back at Bantam—but never found.
Customer support was a mess.
We were using one of the “top” help desks at the time. It was bloated. Slow. Took us ten clicks to do what should’ve taken one. We were growing, and our support system was slowing us down.
I figured we weren’t alone.
So I hired a local dev shop and got to work.
No office. No team. Just me and a hunch that there had to be a better way to help growing companies talk to their customers.
We called it Groove.
The idea was simple. Build a dead-simple, fast, and clean help desk for small businesses. Something teams could actually enjoy using. No training manuals. No clutter. Just a tool that made support feel human.
We launched the beta in July 2011.
A thousand signups in seven days.
It wasn’t magic. It was years of frustration, channeled into a tool people actually needed. That early momentum told me we were onto something—but it also lit a fire.
Now we had to deliver.
The Blog That Changed Everything
In the early days, we had no marketing team. No budget. No distribution. Just a product and a small list of users.
We weren’t growing fast enough.
I knew we needed to do something different, something scrappy. So in 2013, I made a bet.
I started writing.
Not feature announcements or fluffy “thought leadership.” I pulled the curtain all the way back. Revenue numbers. Growth struggles. Customer wins and losses. Team missteps. Every raw detail of building Groove from scratch.
I called it “The Startup Journey.”
It took off.
Founders started sharing it. Investors read it. Customers signed up. Within months, it became the single biggest driver of traffic, leads, and trust for the business.
But more than that, it became accountability. If I was going to write about building something real, I had to actually do it.
We kept shipping. Kept listening. Kept fixing what was broken. No big launches. Just slow, steady compounding.
By 2016, Groove hit $1M in ARR.
No venture capital. No big team. Just a handful of us, obsessed with solving a painful problem and talking to our customers like real people.
That year felt like validation.
But also a warning.
This was the phase where most companies either hit escape velocity—or stall out.
And I had no idea which path we were on.
From $1M to $5M ARR
Most people think the first million is the hardest.
It’s not.
The hardest part is what comes after.
Between $1M and $5M ARR, Groove nearly broke more times than I can count.
We rebuilt the product from scratch. Twice.
Not because we wanted to. Because we had to. Early architecture couldn’t handle where we were going. We hit walls with performance, UX, and feature bloat. Fixing it meant rewriting everything. Months of work just to get back to zero.
We hired too fast. Then had to fire.
Made the wrong calls on senior roles. Misjudged skill sets. Let culture drift. At one point, half the team turned over in under a year. Morale took a hit. So did momentum.
I stepped away from the day-to-day.
That was a mistake.
Without a clear driver, the engine slowed. We coasted. The blog stopped. Traffic flatlined. Growth plateaued. We weren’t bleeding out, but we weren’t sprinting either.
Eventually I came back in.
Refocused the roadmap. Rebuilt the team. Restarted the content engine. Tightened the value prop. Got back on calls with customers. Took it one week at a time.
We didn’t chase trends. We fixed fundamentals.
By 2024, Groove hit $5M ARR. Still bootstrapped. Still lean.
Five people. Five million.
No sales team. No paid ads. Just product, support, and content that worked.
It felt good. But I wasn’t satisfied.
Because I knew how much time we’d wasted figuring it all out the hard way.
What I Wish I Knew
There’s no playbook for getting to $5M ARR.
But there should be.
Looking back, there are things I would’ve done differently. Not small things. Big ones. The kind that cost you time, traction, and sometimes team.
I wish I’d focused on distribution earlier.
We spent too much time perfecting features and not enough time getting them in front of the right people. It took me years to understand that GTM isn’t a channel—it’s the entire engine.
I wish I’d said no more often.
We built things customers didn’t need. We took calls with partners that led nowhere. We hired for scale before we had scale. All because I was scared to miss an opportunity. Turns out, the real risk is spreading yourself thin.
I wish I’d measured the right metrics.
Vanity numbers feel good. But they lie. We chased signups and traffic when we should’ve been tracking activation, expansion, and payback. Once we started doing that, everything got clearer.
I wish I’d systemized support earlier.
Ironically, for a help desk company, our own support was duct-taped together for too long. We didn’t automate enough. We didn’t document properly. We let Tier 1 stuff clog up the inbox. That changed when we got serious about reducing volume, not just replying fast.
I wish I’d built for profit from day one.
Revenue hides problems. Profit exposes them. When the cash is tight, you notice waste. You notice inefficiency. Groove was lean, but we could’ve been leaner—and more profitable—sooner.
I wish I had a real growth system.
Something predictable. Something measurable. Not “try a bunch of stuff and hope.” That’s what most founders do. I know because I did it. It works—until it doesn’t.
So I built one from scratch…
Why I’m Building It All Again
In 2024, Groove was stable. Profitable. Five people. Five million in ARR.
Externally, it looked like the finish line. Internally, I was restless.
That year, something clicked.
I saw the shift happening. Agentic AI wasn’t just hype. It was the future of customer support. Smarter systems. Self-learning workflows. Real outcomes, not canned responses.
And nobody was doing it right.
So I went back into builder mode.
No funding. No deck. Just a blank doc and 300 customer interviews. I talked to founders, support leads, ops teams. Heard the same patterns. Knowledge everywhere. Agents burned out. Tools outdated. AI stuck in 2019.
I built a prototype.
It wasn’t pretty. But it worked. It showed me what was possible if we threw out the old playbook.
I started assembling a team. First hire: Tom Morkes, Head of Growth. We launched a private beta. Handpicked 100 VIP users. Watched every interaction. Fixed every edge case. Iterated fast.
In 2025, we went deeper.
We acquired InstantDocs to solve a critical gap—documentation was still broken. We brought in world-class developers. We rebuilt the authoring experience from the ground up. We connected the pieces: live support, AI agents, docs, and data.
Then we wrapped it all under one banner.
OptimizeCX.
A new micro, Ai-first holdco. Built for SaaS. Each company and each product is lean. Focused. Profitable by design. Not some bloated suite (the opposite of ’all-in-one’s’ and ‘one-size-fit-alls’ that never fit anyone).
Just the essential tools, deeply integrated, with an aggressive GTM about to go live.
This is the system I wish I had ten years ago, and we’re building it live.
What Zero to $10M Really Is
I don’t want to sell a course. Never did. Still don’t.
I don’t think a static course is really what a founder needs. Founders are active. In the thick of it. Deep in the trenches…
What founders need is a system; not just a GTM strategy they can implement, but everything built around that to support that system:
- live training
- real-time Q&A
- private Slack access for direct access to me and my team
- a list of vetted contractors (plus GTM playbooks for them to run)
- detailed, step-by-step guides for implementing specific GTM tactics
This is the system I wish I had when I was stuck.
Stuck rebuilding Groove for the second time…
Stuck hiring the wrong people…
Stuck chasing tactics instead of building a strategy…
Zero to $10M is not theory. It’s not recycled templates. It’s not “growth hacks.”
It’s the real-time playbook we’re using right now to scale OptimizeCX to $10M ARR - with InstantDocs and Helply on track to hit $1M ARR each in under three years.
Everything inside Zero to $10M is built around execution.
- Weekly playbooks.
- Live metrics.
- Our ad campaigns.
- Our outbound scripts.
- Our content calendar.
- Our exact AI workflows.
- Every test, win, and faceplant. In public. In real time.
It’s also a community.
Vetted. Founders only. No fluff. No spectators.
We run bi-weekly calls, review your GTM, and share what’s working across SaaS verticals. If it doesn’t drive revenue or save you time, it doesn’t get in.
We’re not selling hypergrowth.
We’re building sustainable, profitable companies with 50 percent margins.
This isn’t for founders chasing their next round. It’s for founders who want control.
We’re building for freedom, not exits.
If that’s you, this is for you.
