How a Southern Boy and a Pilot Upended the Accounting World
You’ve likely heard that 90% of startups fail within their first few years.
It’s the kind of number that sticks. Big, ominous, easy to remember… and funny enough, entirely untrue.
The real figure reveals that 65% of startups fail within ten years—20% in their first year.
Now that is interesting, isn’t it? The first year is disproportionately brutal compared to the later nine. Those first 365 days are a crucible, where your business either breaks… or forges something better.
I believe reflecting on “Year One” is essential for future growth. It takes pressure to make diamonds—and I’ve found quite a few gems looking back on Quadrant’s early days.
I’d like to share those treasures with you. But not as your typical “origin story” piece.
Instead, allow me to share how Quadrant Advisory reinvented the accounting game.
The First Meeting: A Tale of Two Entrepreneurs
Did you know that in Washington, DC, no building is allowed to be taller than 130 feet? No matter where you’re at in the city, you can look to the monuments that crown our nation’s capital.
It was in this unforgettable backdrop that I first met my business partner, Chris May, CEO of Quadrant Advisory. Let me set the stage:
- It’s 2019, and business is booming like never before
- I’d just exited a successful venture and was itching for the next one
- Quadrant Advisory had just undergone a rebranding from CM Solutions
Those three points may sound incidental, but looking back, it’s amazing how the stars aligned.
Call it serendipity, call it good timing, but had Chris asked me to join “CM Solutions”? Well, I probably would have politely declined.
But Quadrant Advisory?
Now that had weight. Vision. A nice homage to our geographical roots and the four quadrants of Washington, D.C., but also a framework to serve our clients with four quadrants in mind—Shepherd, Director, Strategist, and Catalyst. That resonated.
Our first meeting didn’t lead to anything concrete. But a seed was planted.
Chris: Strategist by Instinct, Catalyst by Nature
My first impression of Chris May? A big “idea guy”… who could use just a little bit of grounding.
In all seriousness, what stood out about Chris is that he showed a rare mix of strategic thinking and builder’s instinct with his ability to:
- Articulate Quadrant’s values and our value proposition with piercing clarity
- Build the “bones” of the business from scratch
- Rev up the growth engine and reimagine what an advisory firm could be
- Find a funny Southern saying for absolutely any situation…😁
But even the best ideas need grounding. That’s where I came in.
Ramsey: Strategic Shepherd, Dependable Director
When Chris and I started talking seriously, he joked, “If I’d gone off your resume alone, I probably would’ve passed.”
…and I agree! Who would have guessed an F-18 fighter-pilot-turned-entrepreneur could mesh well in an industry dominated by accountants? Yet it was these very qualities—operational rigor, creativity, and resilience to persevere with limited resources—that balanced out Chris’s big-picture energy.
Somehow, he sensed that.
“Ramsey’s intangibles are what sold me,” Chris later shared. “And in that first year of COVID, facing multiple existential business challenges? Yeah, I was lucky to have someone with a level head (and Marine Corps experience) at my side.”
And from that moment on, I’ve been all in.
A Battle-Tested Business
From day one, Quadrant didn’t look like a typical accounting firm:
- Leadership built from entrepreneurs and operators rather than traditionalists
- Hybrid-remote model (yes, even before COVID made it cool)
- Intense focus on talent, team, and culture
We weren’t trying to be rebellious. We were just building the kind of firm we wished we’d had at our disposal as business owners.
True, we aren’t CPAs, but rather operators who understand the pressures of running a business. We also aren’t marred by experience—we tackle legacy problems with fresh eyes, resourcefulness, and a “believe it’s possible” conviction.Most accounting firms hand you reports. We offer clarity. Most firms stay in their lane. We help drive the entire financial engine.
And where others saw our lack of “traditional background” as a weakness, our clients saw an edge.
Forged in the Fires of a Pandemic
As mentioned, Quadrant’s rebranding debut fell right in the thick of COVID chaos.
Our Downtown DC office, once full of hustle and chatter, now sat eerily silent.
No more drop-ins. No whiteboard sessions. No mentorship moments.
We were navigating the same crisis as our clients—only we were also helping them survive it.
To stay grounded, we remained focused on our clients. Just hands-on work with our team, solving real problems, one day at a time.
We didn’t have a playbook, but we were rigorous with setting priorities and allocating team members and resources accordingly.
And we made it through stronger—and more focused—than before.
Quadrant Advisory: More Than a Survival Story
Quadrant wasn’t born in a boardroom. It grew from real conversations, hard-earned experience, and a shared belief that financial clarity is mission-critical.
We orient our actions around the following key overarching objective for our clients:
Deliver the financial clarity business leaders need to make effective business decisions.
Even with the best capital, tech, and timing, you can’t anticipate every curveball. The first year may sound like the biggest hurdle—but it’s the first decade that kills 65% of startups.
And the single biggest reason for these failures? Poor financial planning.
We know what it feels like to look at a cash flow report and wonder if you’ll make it to next month. We know the weight of headcount decisions, pricing strategies, and investor pressure. And we know that good accounting is more than clean books. It’s the foundation of good decision-making.
That’s not something your everyday Joe CPA can say.
Quadrant’s outsourced accounting and financial advisory services aren’t a cold and calculated transaction. They’re us giving a part of our culture and people to make sure your finances are handled with the care and attention they deserve.
If you think you could benefit from outsourced accounting or financial leadership, why not reach out? Let’s connect for a consult and see where it goes.
The best flights always start with the right briefing. And wheels down, or wheels up, I’m always up for a good conversation!
Sources:
Forbes. Understanding KPIs and Their Importance in Your Business. https://www.forbes.com/sites/melissahouston/2023/10/20/understanding-kpis-and-their-importance-in-your-business/
Harvard Business Review. KPIs Aren’t Just About Assessing Past Performance. https://hbr.org/2021/09/kpis-arent-just-about-assessing-past-performance