Financial freedom buys time for work that never pays a dividend

Most arguments for financial independence are about escape: leaving a job, a boss or a commute behind. Jimmy Tran makes a different case. In his view, the point of building enough wealth to step away from full-time corporate work is the freedom to spend hours on things that will never show up on a balance sheet.

"The beauty and the privilege of pursuing time freedom, if you will, or financial freedom is that you can invest in things that don't immediately or maybe never pay [an] exact dividend," Tran said on Beyond the Ledger. For him, those things are concrete. He named coaching his kids' sports teams and serving on a civic board or a nonprofit board, work he can take on without treating every hour as an exchange of time for money.

That raises the question that matters to finance and accounting professionals weighing the same move. What does it actually take to get there, and how honest are the people who made it about the costs? Tran's account is useful because it doesn't skip the unflattering parts.

Why the corporate package is so hard to leave

Tran came to this argument from inside the kind of career people rarely leave on their own. He spent roughly nine years connected to Bain & Company, where he worked as a management consultant in Dallas, Hong Kong and Singapore, with three of those years in graduate school the firm sponsored. He then moved in-house at CBRE, leading corporate strategy and mergers and acquisitions for a $10 billion-plus business segment for seven or eight years. Host Troy Ashby credited him with helping build and lead more than $2 billion in acquisitions there, and over eight years the segment tripled its earnings. Tran estimated the team closed roughly one investment or acquisition a month.

That background explains the reaction he got when he started saying, in his twenties, that he planned to pursue FIRE. "I'd tell everybody and half the people looked at me like I was crazy," he recalled. Their argument was that someone with his pedigree wouldn't walk away from corporate America. Tran conceded the pull is real. "The golden handcuffs are real, you get sort of enticed to stay," he said. He still didn't want to be doing the same work at 62.

His sharpest warning is about the math of leaving. People who earn a salary plus stock and other incentives tend to underestimate how hard that package is to rebuild on their own. If you're in that position, Tran said, "you're not going to replace that in any short or near term."

He described most entrepreneurial journeys as a five-to-ten-year path. Even companies with famous exits, like Airbnb and Uber, took about a decade to get there, he pointed out. The fanfare around entrepreneurship tends to skip that part.

Building the cushion before the exit

Because the income gap is so wide, Tran treats financial freedom as a long project, not one decision. "It's a long game," he said. "You can't just decide today and then tomorrow, just do it." He set up an LLC before he and Ashby ever met, and by 2018 he was actively making private investments in real estate and other areas, including flipping homes, to build what he called "some cushion" that could partly replace his corporate income.

He was clear about how that turned out: "I didn't fully replace my income." That admission matters. Much of the cultural story around entrepreneurship assumes side income eventually matches or beats the salary. In Tran's experience, the realistic target was enough stability to make the move, not income parity. He also named the household variables anyone planning a similar move has to work through:

• Insurance coverage, especially for anyone with a family
• Whether a spouse works, and whether that income adds stability
• Side projects that can produce residual or other income before you leave

Each of these changes how big the cushion needs to be. A household with a second steady income and existing coverage can absorb a bigger shortfall than one that runs on a single paycheck. Tran didn't offer a formula. His list works better as questions to answer before setting a date than as a checklist to finish afterward.

The exit rarely arrives as planned

Tran had a target: out of corporate America by 40. He hit it in 2020, though not entirely on his own terms. "It was somewhat intentional, but to be candid, I was also laid off," he said, calling it "a blessing in disguise." Because he had been preparing for years, the layoff sped up a move he already intended to make. It wasn't a crisis that forced him to start from scratch.

What came next is what he calls an "entrepreneurial advisory kind of portfolio life": investing through Oak Lawn Group, the real estate and income-producing-assets firm he founded in 2010, advising middle-market business owners on the sale of their companies at Optima Mergers & Acquisitions, and working with civic organizations and nonprofits in Dallas. That's a different scale from CBRE, which by his estimate now has more than 150,000 people across roughly 50 countries. He contrasted it with the narrow but high-volume view he had there; even at very large companies, he noted, corporate strategy teams often number only a couple dozen people.

He also pushed back on the idea that his path was planned. On LinkedIn, he said, it can look deliberate and linear. In reality it was more like a jungle gym than a ladder, partly serendipitous, with "some second guessing along the way." Ashby compared it to Chutes and Ladders, and Tran agreed: "you could be at the very end and restart." In his framing, preparing for freedom is less about mapping every step and more about having enough cushion to absorb the moves you didn't choose.

Saying the plan out loud

Tran's most practical advice is about talking, not money. He told so many people about his FIRE goal that it became a running conversation. He argues that was the point. "You need to tell people because it creates accountability," he said. The next time a colleague sees you, they'll ask what happened to the plan you mentioned.

Ashby's own memory backs this up. When they first met, he said, he doubted a CBRE executive would actually leave. Then, in a later conversation, Tran brought up FIRE again, and Ashby remembered thinking, "okay. He's real." The two kept talking about it off and on for nine or ten months, around the time Ashby was starting his own firm, Benchmark Search.

Speaking up has a second payoff beyond accountability, Tran said. If you're considering an advisory business, a search firm or a new company, telling people can put you in front of an investor, a first client or someone who will spread the word for you. And announcing a plan doesn't lock you in. Exploring it and deciding "it wasn't for me" is still a legitimate result.

What he tells owners getting ready to sell

The corporate exit was not Tran's last one. He built a consumer-facing business during COVID, a stretch he called "really tough," and sold it in 2025. After the sale he weighed starting something new, buying a small business or going back to corporate work, and found that returning was hard once you "taste freedom." He landed at Optima Mergers & Acquisitions, which he describes as the owner's representative on the sell side for middle-market companies: firms too small for the investment banks and too large for main-street business brokers, often selling to private equity.

His starting point is the imbalance in those deals. A founder is usually selling for the first time, while the private equity buyer has done it many times over. "They know exactly where to squeeze. They know exactly where to negotiate. They have lawyers. They're armed up," Tran said. And unlike a public company, a private business has no ticker to settle the price: "It's not a stock that has complete price transparency."

The most common mistake he sees is anchoring on a headline multiple heard secondhand. "They come in thinking it's all about the number, but the number is just one aspect or one component of an overall deal or transaction," he said. Structure can matter as much as price, from how much equity the owner rolls over and whether they must stay on, to working capital, reps and warranties and the purchase agreement. With baby boomer owners retiring and the next generation often uninterested in taking over, he expects that deal flow to keep coming. "There's a term for this. It's called the silver tsunami."

His preparation advice echoes his own FIRE playbook: start well before the exit. Keep the business stable or growing, clean up financials that mix personal and business expenses, put client contracts in writing, and build the processes, playbooks or number two that let it run without the owner. "Buyers are going to discount whatever the value is based on these risk factors," he said.

What the freedom is actually for

Tran's account brings the argument back to where it started. The investing, the cushion, the years of telling people his plan, even the layoff, all served one goal: hours he can spend on a sports team or a nonprofit board without asking what they're worth in dollars. By his own account, the return on that time may never be measured.

For finance professionals who feel the golden handcuffs, his experience points to a few hard questions before planning an exit. Can your household cover the gap between a corporate package and whatever you build on your own, possibly for five to ten years? Have you started building that cushion while you're still employed? And who have you told? In Tran's case, the honest answer was that he never fully replaced his income. He decided the trade was worth it anyway.

Jimmy J. Tran is an investor, M&A advisor and civic leader based in Dallas. He founded Oak Lawn Group in 2010 and serves as an M&A advisor at Optima Mergers & Acquisitions. He began his career at Bain & Company, led corporate strategy and M&A for a business segment at CBRE, and holds four degrees from SMU and two from Harvard. He is vice-chair of the City of Dallas Economic Development Corporation, has served on the boards of the SMU Simmons School of Education and the Harvard Business School Club of Dallas, and is a Dallas Business Journal 40 Under 40 honoree.