I quit a stable property management job with eight months of runway and nothing else lined up. Within a year I’d co-founded Blue Rabbit Group, launched Zenith Degree, and become a father.
Here’s what actually happened, and what I got wrong about what “freedom” would feel like.
No exit strategy, no soft landing, no side income quietly running in the background. Just runway, an itch that had been building for years, and a journal full of things I’d written down long before I had any plan to make them real.
The Stable Job That Stopped Making Sense
The tipping point wasn’t dramatic. I was working as a project manager, licensed as a property manager in South Carolina, and the math had stopped working.
The pay no longer matched the headache.
Even when a director role came across my desk where the pay was closer for the headache, I turned it down.
My wife and I were trying for a kid, and the Director job would have meant missing holidays, soccer games, and birthdays.
I’d saved during Covid and invested it, on top of stock options and RSUs I exercised from my time at Sonder (the Sonder stocks were nothing to write home about). That gave me a safety net most people quitting a stable job don’t have.
Safety net or not, the choice still felt reckless in the moment. My wife thought I was nuts. I don’t blame her.
I took a short sabbatical to figure out what came next. I didn’t have a business plan. I had a license, some savings, and enough conviction that the current path wasn’t it.
Eight Months of Runway, Not a Blind Leap
Quitting felt reckless from the outside, but it wasn’t blind. Between Covid savings I had roughly eight months of runway, enough time to build something real before the money ran out.
Eight months sounds like a lot until you’re the one watching it shrink every month with no revenue coming in. It was enough time to be patient. It wasn’t enough time to be lazy. Every week that passed without traction was a week closer to needing a real job again, and that pressure shaped how fast I moved.
A Phone Call That Became Blue Rabbit Group
Blue Rabbit Group started with a phone call, not a plan. A former colleague who’d built a successful consulting business kept fielding inquiries about long-term property management. She floated the idea of a boutique multi-family property management company for the Southeast. It took several more calls before it felt real.
The idea of starting a venture was foreign to me at first.
We spent weeks working out the brand, the identity, the culture, and more than anything, the mission.
Multi-family management across the Southeast is a different animal than what I knew, and I wasn’t going to attach my name to it without understanding what we were building. Once we did, it felt like something worth the effort.
Zenith Degree Started as a Side Project
While Blue Rabbit Group was still taking shape, I didn’t want my South Carolina property manager license sitting unused. I started Zenith Degree as something smaller and more local, built for friends and family in the Hilton Head Island area.
It was never intended to be the business that caught wings like it did.
Above is me grinning with my first signed contract for a tenant placement program.
What started as a side project to keep my license active and help people I actually knew turned into a business with its own momentum almost immediately.
The Same Month I Started a Company, I Became a Father
The day after I officially established Zenith Degree, my wife came home and told me she was pregnant.
Two companies in motion and a baby on the way, all within weeks of each other.
It felt less like starting business’s and more like having triplets.
Owning a business was attractive for a lot of reasons, but the biggest one was being present. I figured working for myself meant more time around my family.
What I didn’t understand yet was how demanding building something from nothing actually is, and how easy it is to work around the clock without meaning to.
Owning a Business Is More Demanding Than Any 9-5
The tradeoff of owning a business isn’t fewer hours, it’s where you spend them.
I work more now than I did at any 9-5. What I gained wasn’t free time, it was the ability to be physically present for the moments that mattered, even while working through the rest.
That’s a distinction most people don’t make when they picture quitting a stable job. Founder life doesn’t hand you your evenings back. It hands you control over which parts of your life you’re present for, if you’re disciplined enough to use it that way.
I am by no means a saint with this. It’s been hard keeping boundaries.
How Zenith Degree Scaled Without Losing the Boutique Feel
Zenith Degree grew faster than I expected, delivering management services at a competitive price with real value behind it.
I onboarded a virtual agent, got an office, and leaned hard on AI and open source tools to handle the volume without losing the boutique feel that got us here.
The specifics of what runs where are something I’m saving for people who actually want to dig in.
What I’ll say here is that marketing, tenant and vendor coordination, and applicant screening (with the applicant’s approval) all run through a mix of open source projects and different LLMs, depending on the task.
Which model handles what isn’t random.
It’s a system I’ve built and rebuilt more times than I’d like to admit through trial and error.
The Boundary I’m Still Trying to Set
I’m not going to pretend I have this figured out.
Setting real work hours, knowing when to put the phone down, and being honest with myself about what’s actually worth my time has been the true challenge.
Do I sometimes miss being fully off, the way I could be as an employee?
Yes.
But I remember exactly what that feeling was chasing. It was the same itch that started this whole thing. I’d rather have the itch and the ownership than the time off and the wondering.
So To Sum It Up
Quitting a stable job doesn’t require certainty.
It requires real runway and a decision you can live with if it doesn’t work out.
The tradeoff of business ownership is presence, not free time. Those aren’t the same thing.
Two companies and a newborn arriving in the same stretch will test every assumption you had about having it figured out.
Boundaries aren’t something you set once. They’re something you keep rebuilding as the business grows.
If you want the actual breakdown, which LLMs I use for marketing, tenant coordination, and applicant screening, and how the whole system fits together, that’s exactly what I’m covering in my newsletter!
