There is a version of Brian Cunningham‘s story that sounds almost cinematic. The decorated professional soccer career that took him across four countries, the championship won with a legendary american soccer club in 2015, a clean arc, a good story.
But that version leaves out the part that actually shaped him.
The part that actually built him.
Figuring It Out on His Own
When Brian turned professional as an athlete, he quickly ran into something nobody had prepared him for. His management was all but present, leaving the deals, the team negotiations, the sponsorships, and even more in his hands. Life changing decisions that typically require management expertise, were handled by a young athlete who only just finished his business degree at Virginia Tech. “I had a really rough experience with agents and management,” he says. “I did almost everything myself. Finding teams, negotiating terms, finding brands that would sponsor me.”
He played anyway. New York, Jamaica, New Zealand, Tampa. He won a national championship with the New York Cosmos, a legendary American soccer club. On paper, things looked fine. But underneath all of it, he was carrying something that stuck with him long after the games were over,it was a lesson he filed away and never forgot: what it means to be in a trajectory-defining moment, and how much the right person in your corner can change the outcome
That word, trajectory, comes up when Brian talks about that period. He is precise about it. Because he understands, better than most, what it means when the right guidance is missing in the moments its needed most.
The Pivot Nobody Saw Coming
When his playing career wrapped up, Brian moved toward what had always been pulling at him anyway. He started working with former teammates and friends who were still playing. Managing their careers, putting into practice everything he had picked up along the way. Not as an agent, but as an advisor to his friends who found themselves at crossroads in their own careers.
It worked, their careers moved, and Brian noticed something.
The skills that helped an athlete navigate a career, knowing how to position yourself, how to negotiate, how to build something around your own name, those same skills translated directly into business. So he took what he had learned and started applying it to founders and entrepreneurs. Solopreneurs trying to get off the ground, established professionals trying to grow, public figures trying to build something off their beaten path.
Before long he had opened over 200 companies for other founders through his sole proprietorship, before eventually deciding to build a consulting firm. He was the background guy, the one who made things happen without making it about himself.
What He Was Actually Building
Over the years, Brian’s work has expanded in ways that are hard to capture in a single job title. He runs a consulting portfolio, holds positions on the cap tables of startups with multiple seven and eight figure valuations, and continues to play an active role in the companies he is invested in.
One of his portfolio companies grew 10x in revenue from year one to year two. Then 4x on top of that the following year. That kind of growth does not happen by accident and it does not happen without someone paying close attention.
He holds personal equity in eight companies. He has helped clients go from zero to $300,000 in a matter of months. From six figures to multiple seven. He has helped people pull themselves back from the edge of bankruptcy. And he is still doing all of it.
None of this gets performed online. Brian has always been deliberate about that, he is not interested in broadcasting success. He is interested in creating it, for the founders and businesses he works with every day.
The Thing Nobody Was Saying Out Loud
At some point along the way, Brian started noticing the same thing across nearly every consulting client he worked with. Their taxes and finances were not being strategically managed. They were just being handled. Filed, processed, and forgotten until the following year. Most of them did not know what that was costing them.
“So many entrepreneurs rely on their CPAs who are just paper-pushing their taxes and not really protecting their assets,” Brian says. “Your tax professional is your first financial advisor, people don’t treat it that way.”
He had ambitions of becoming a CPA himself at one point. He grew a firm’s monthly recurring revenue by $38,000 and spent two years studying for the exam. When the accountant he worked under could not endorse him, that door closed. But the knowledge stayed. And the drive to actually help people, not just file their paperwork, never went anywhere.
From purchasing private jets to structuring $21M acquisitions, accounting became a real part of Brian’s journey.. He aligned with forward-thinking CPAs and built something around what he believed tax advisory should actually be, not a once-a-year chore, but a real wealth creation strategy.
Olivantage
That thinking eventually became Olivantage, a tax advisory firm built for founders, high earners, and small to mid-sized businesses who need more than a CPA that shows up once a year.
The work at Olivantage covers the kind of territory most tax conversations never get to. Audit scrutiny, IRS debt resolution, business credit, real estate tax implications. The intersection of a founder’s business life and personal financial life, which rarely stay neatly separate from each other.
Brian is not a CPA. He says that plainly. But what he has built around himself, a network of strategic partners, a methodology refined over a decade of real client work, is something most CPAs are not offering.
“I’ve helped people save millions in taxes,” he says, with the matter-of-fact tone of someone who has seen it happen enough times that it stopped surprising him.
The Long Game
Brian talks about a venture capital firm that is in the works. He talks about building his entrepreneurial ecosystem so that clients and partners can actually benefit from the resources and relationships he has spent over a decade putting together. He is working with family offices, management companies, and agencies.
The work looks different now than it did ten years ago, but the motivation behind it never really changed.
Because everything Brian Cunningham has built traces back to the same original frustration: being in a pivotal moment without the right person in your corner. He lived that, he learned from it, and then he spent the better part of a decade making sure other people didn’t have to.
That is the through-line, that is the whole story.
