From Inc. 5000 to 500 Employees: The Unsexy Truth About Scaling
When we hit #326 on the Inc. 5000, I got a lot of congratulations. LinkedIn posts. Text messages. People I hadn’t talked to in years reaching out. It felt great.
What nobody saw was the year before that ranking. The cash flow crunches. The hiring mistakes. The client I should have fired six months earlier. The nights where I sat in my office wondering if the growth we were chasing was going to be the thing that killed us.
The Inc. 5000 is a snapshot of revenue growth. It tells you nothing about the chaos behind the growth. And I think more founders need to hear the real story…not the press release version.
The Cash Flow Crunch of Rapid Growth
Here’s something they don’t teach you in business school — or if they do, it doesn’t stick until you live it: rapid growth is expensive.
At OA, we pay our team in the Philippines on the 1st and 15th. Our clients pay us monthly, usually net 15 or net 30. When you’re growing by 20 or 30 team members a quarter, the math gets ugly fast. You’re paying salaries before you’ve collected revenue from the clients those team members serve.
I remember a stretch where we added a significant number of new team members in a single quarter. Every one of them was tied to a signed client. Revenue was coming. But “coming” doesn’t help when payroll is due Friday.
This is the part of scaling that sounds like complaining to people on the outside. “Oh, you’re growing too fast? Poor you.” But anyone who’s been through it knows…growth without cash flow management will destroy a company faster than stagnation.
The lesson: growth is not the goal. Profitable, sustainable growth is the goal. And those are very different things.
The Hiring Mistakes
When you’re scaling fast, the pressure to fill seats is relentless. A new client signs. They need a VA by Monday. Your talent team is already stretched. And so you make compromises you swore you wouldn’t make.
You hire someone who’s “close enough.” You skip the second interview because there’s no time. You put someone in a role they’re not quite ready for because the alternative is telling a client you can’t deliver.
Every single one of those shortcuts comes back to bite you. Every. Single. One.
The VA who wasn’t quite right for the client creates a service issue that takes your Operations Manager 20 hours to resolve. The team leader you promoted too early makes decisions that demoralize their team. The hire you didn’t vet properly quits after three weeks, and now you’re re-recruiting, re-onboarding, and re-apologizing to the client.
I’ve learned that the cost of a bad hire isn’t just the salary you paid them. It’s the management time spent cleaning up the mess. It’s the client trust you have to rebuild. It’s the team morale that takes a hit when they see that standards were lowered.
Now we slow down to speed up. Better to take an extra week to find the right person than to spend three months recovering from the wrong one.
The Client You Should Have Fired
I’m going to be honest about something that took me way too long to learn: not every client is a good client.
When you’re growing, you want every dollar. You take clients you shouldn’t. You tolerate behavior you shouldn’t. You bend your processes to accommodate someone who doesn’t respect them.
We had a client — I won’t name them, obviously — who was consistently abusive to their VA. Unreasonable deadlines. Harsh language. Moving goalposts. Our team flagged it. Our management tried to address it. The client pushed back. And I let it continue for months because the revenue was good.
That’s a failure of leadership. Full stop.
The VA was miserable. The TL managing the account was spending disproportionate time on damage control. And the culture message it sent to our team was clear: “Revenue matters more than you do.”
The day we let that client go, I felt the relief in our team. Not just the VA who was reassigned — the entire team. Because they saw that we meant it when we said “people first, process always, profit eventually.” Profit eventually. Not profit at any cost.
Now we have a clearer filter. If a client doesn’t align with our values, they’re not our client. That alignment matters more to long-term growth than any single contract.
Growth for Growth’s Sake Is a Trap
There’s a culture in entrepreneurship that glorifies growth. More revenue. More employees. More clients. The bigger the number, the more impressive you must be.
I bought into that for a long time. And here’s what I learned: growth without purpose is just a more complicated version of the same problems you had when you were small.
At 50 employees, I was overwhelmed. At 200, I was more overwhelmed with better revenue. At 500+, I’m less overwhelmed than I was at 200…not because the problems got smaller, but because I finally stopped chasing growth and started chasing disciplined growth.
Disciplined growth means saying no to the client who doesn’t fit. It means hiring at the pace your systems can absorb, not at the pace your sales team can sell. It means accepting that a quarter of slower growth while you fix your infrastructure is worth more than a quarter of hockey-stick growth on a cracking foundation.
Jim Collins calls it the “20 Mile March” — consistent, disciplined progress regardless of conditions. Not sprinting when times are good and collapsing when they’re not. Just steady, relentless, boring forward motion.
That’s how you get to 500+ team members and actually enjoy it. Not by racing there. By marching.
The EO Lifeline
I would not have survived the hardest parts of scaling without the Entrepreneurs’ Organization.
I’ve been an EO member for 10 years. I served as president of EO Atlanta. I was the US East Coast Regional Director, overseeing 22 chapters and 2,000 members. And the thing I value most about EO isn’t the title or the network…it’s the forum.
For those who don’t know, an EO forum is a small group of entrepreneurs who meet monthly to share experiences. Not advice. Experiences. You present a challenge, and instead of telling you what to do, each person shares a time they faced something similar and what happened.
During the cash flow crunches, the hiring mistakes, the client I should have fired…my forum was there. Not with platitudes. With real stories from people who’d been through the same thing. “I had a client like that. Here’s what happened when I held on too long. Here’s what changed when I let go.”
Scaling is lonely. The bigger the company gets, the fewer people you can talk to honestly about what’s going wrong. Your team needs you to be confident. Your clients need you to be stable. Your investors — if you have them — need you to be optimistic. The only people you can be fully honest with are other founders who get it.
If you’re scaling and you don’t have a peer group…find one. EO, YPO, a mastermind, something. The ROI on having people who will tell you the truth is incalculable.
What I’d Tell My Earlier Self
If I could go back to the version of me who was celebrating our first big growth year, I’d say this:
Slow down. Not forever. Just long enough to build the systems that will make the next stage sustainable.
Fire faster. The client who doesn’t respect your team. The hire who isn’t right. The process that’s clearly broken. Waiting doesn’t make these better. It makes them more expensive.
Celebrate less, build more. The Inc. 5000 ranking was a lagging indicator of work we’d already done. The real question was always: what are we building right now that will still be working in three years?
And stop glorifying the grind. The unsexy truth about scaling is that the most important work isn’t dramatic. It’s disciplined. It’s consistent. It’s the thousandth Playbook. The hundredth weekly review. The tenth hard conversation handled with integrity.
That’s what scaling actually looks like. Not a press release. A practice.
Stay in the Conversation
Every week in The Full Potential Dispatch, I share the real lessons — not the highlight reel — from 25 years of building businesses across 18 countries with 500+ team members. If you want the unfiltered version of what scaling actually takes, subscribe here.
And my book “Automate and Delegate” drops May 30, 2026, with the complete framework for scaling with discipline, delegation, and systems that actually hold up under pressure. Pre-order your copy here.
