Clay Cowan considered himself a personal finance guy. He had followed stocks and investing since childhood and knew his way around retirement strategies.
Yet when he encountered IRA Financial, the company he would soon join as CEO, Cowan discovered a sizable hole in his financial vocabulary: He had barely heard of self-directed retirement accounts.
Then he began counting the opportunities he had missed.
Cowan – a marketing veteran who has held C-suite roles at IBM, Betterment, and Gilt.com – had considered making a small real estate investment but did not know he could use retirement funds. He had invested in a private company without realizing that money might have gone into a tax-advantaged vehicle. And while doing consulting work, he had underestimated the potential of a solo 401(k).
“I say this sheepishly, but honestly: I should have known, but I didn’t,” Cowan [pictured above] told Refresh Miami.
That realization helped draw Cowan to IRA Financial, a nearly 100-person fintech company founded by tax attorney Adam Bergman. The business enables customers to use retirement savings for alternative assets including real estate, Bitcoin, gold and private companies, alongside traditional investments such as stocks.
Now overseeing some $8 billion in assets, IRA Financial’s next challenge is explaining why considerably more people might want access to its services.
For Bergman, the journey began with his own moment of financial bewilderment. While working as a tax associate in New York, a client asked to use an IRA to invest in a hedge fund.
“I was totally blown away,” Bergman said. He went on to build IRA Financial, learning how to lead a company along the way. “First-time CEO, I made a million mistakes.”
Bergman brought Cowan aboard to help turn the company from a successful specialist into a mainstream financial platform.
“I love what the company is about,” Bergman said. “For me, it’s more about just having the company really realize the vision of providing real retirement services, true diversification, flat fees, using technology to make it easy and simple.”
That vision depends on converting a strategy familiar to family offices into something ordinary investors can understand and use. Wealthy people often have attorneys, accountants and advisors who know how to place alternative assets inside retirement accounts. Reaching a broader market requires replacing bespoke paperwork with scalable technology.
“The problem with it is the same thing as the opportunity with it: It’s complicated,” Cowan said.
IRA Financial’s pitch is that its technology, backed by in-house legal and accounting expertise, can make those transactions accessible without placing a miniature family office beside every customer. Its longer-term ambition is expansive: If the IRS permits an asset in a retirement account, the company wants its platform to support it as seamlessly as possible.
Artificial intelligence could help remove some of the friction, though Cowan framed it as a tool for improving service rather than cutting jobs. “AI is always going to be an augment for our team,” he said. “The best usage of AI is to make something better.”
The company is exploring AI for faster customer support, internal searches, process automation and analytics. Its summer interns have even been tasked with finding operational, marketing or technical problems and building AI-powered solutions inside a protected sandbox.
As IRA Financial grows, Miami is expected to play a larger role. The company currently has around six employees in the area, a larger operation in South Dakota and remote team members around the country. Bergman, who moved to Miami from New York about 16 years ago, said the company planned to expand its local talent base.
Cowan pointed to Miami’s mix of fintech expertise and consumer-marketing talent, both essential for a company trying to explain an unfamiliar financial category.
“For the last five or six years, fintech in Miami has been kind of the heartbeat of what Miami has been up to,” Cowan said. “We think Miami can really be a core part of that story.”
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