Eight Bosses on Their Biggest Money Regret

The professional and personal finance lessons founders and CEOs have learned along the way.

Takeaways

by Bloomberg AI

• Eight CEOs reflect on decisions they made, and offers they didn’t take, that they still regret, including thinking through the details of a company's sale and not buying shares in an EV maker at an opportune time.
• The CEOs' regrets include scaling their businesses too quickly, spending money on marketing without measuring results, and not learning about financial investments sooner.
• They also regret not taking certain opportunities, such as buying shares in Tesla's IPO, moving to France for a role, investing in travel abroad, and locking in a mortgage for 10 years when interest rates were rising.

Among the chief requirements for the people who run companies is the ability to intelligently oversee finances. There’s the expectation of positive balance sheets, that a deal will make money and that decisions will lead to something fiscally positive. But not every decision can be the right one.

Here, eight CEOs reflect on decisions they made, and offers they didn’t take, that they still regret. They range from thinking through the details of a company’s $94 million sale to not buying shares in an EV maker at an opportune time.

In the mid-1980s, defense attorney Rick Rosenfield co-founded the designer pie company California Pizza Kitchen Inc. In 1992 he and co-founder Larry Flax sold a controlling stake to PepsiCo Inc. for $94 million and, he says, “made two expensive mistakes.” Rosenfield expands on the first one: “We suddenly had what felt like a blank check, and we grew faster than our infrastructure, systems and leadership could support. When PepsiCo decided to exit the restaurant business, the consequences were painful: store closures, layoffs, cost cutting and, perhaps most damaging, a loss of trust among team members.”

Rosenfield says the second mistake came a few years later, when he and Flax sold their share of the publicly traded company to private equity buyers: “Larry and I were so focused on getting the transaction right for shareholders that we paid too little attention to our own future. Ultimately, we lost the ability to shape the company we had spent decades building.” He adds, “Both experiences taught me a similar lesson: It’s easy to become so focused on the opportunity in front of you that you fail to think through what comes next. Sometimes the costliest mistakes aren’t the result of bad decisions — they come from failing to anticipate the consequences of good ones.” Rosenfield goes deeper on the subject in his brand-new book, The California Pizza Kitchen Story: How Two Federal Prosecutors Changed the Way America Eats Pizza.

As CEO of the Sarkis Team at Douglas Elliman Inc. in Boston, George Sarkis oversees more than $500 million in annual sales volume. “My biggest money regret wasn’t a bad investment or a market downturn; it was scaling before I was truly ready to scale,” he says. “Early in my career, I hired people and increased payroll faster than I built the systems, processes and accountability needed to support that growth. Great people are important, but even great people struggle without clarity and structure.”

Another regret he has was when he would spend money on marketing without a definitive way to measure results. “For years, I invested in initiatives because they sounded good or looked impressive, or because everyone else was doing them. Today, every dollar we spend on marketing is tied to a strategy, a measurable objective and a way to track performance. Brand awareness matters, but understanding ROI matters even more.”

Amy Walker is one of the youngest CEOs of a publicly listed company in the UK; she turned 33 in July and is the boss at 4basebio PLC, a maker of synthetic DNA for biotech and pharmaceutical companies. She flashes back to her earlier years. “When I was in school, there was really no curriculum to support how young people should make money work for themselves. I knew next to nothing about investments, tax, anything. There really wasn’t anything in the curriculum, and I’ve learned that the hard way.”

Consequently, financial stability and understanding financial investments have become a motivating factor for her. “The regret is perhaps not learning about that sooner and being able to capitalize on that knowledge. How to build long-term financial security and make informed decisions about wealth creation,” she says.

“During my time between Experian and Disney, I executive-produced an indie comedy, Rock Slyde,” says JB Orecchia, the CEO and president of SavvyMoney Inc., the credit-score-focused financial tech platform based in California. It was “not exactly a line item most financial planners would approve of, and I knew going in it was a long shot. No regrets.”

And that’s the point, he says. “The money decisions I can live with are the ones I made with my eyes open, even when they didn’t pan out. The ones that actually stay with me are the quiet ones. You wait for a real moment — buying a house, losing a job, getting declined on something — and that’s when you finally look. By then, time has already cost you. It is important to take calculated risks with money you can afford and set a limit on what you can afford. What you measure, you will manage.”

In 2011, George Morgan-Grenville founded the travel firm Red Savannah, where he’s also the CEO. The company specializes in international adventures with categories that range from safari to sabbatical and VIP ski to glorious isolation. His specific regret dates back to 2010. “That I didn’t buy the 588 shares I was considering in Tesla Inc.’s IPO at a cost of $10,000. And then sell them again when the stock peaked in December 2020. The return — factoring in the 5-to-1 split in August 2020 — would have been $3.6 million, 20,655%.”

Meenakshi Lala has been the CEO of the online flower delivery business UrbanStems Inc. since November 2023. Her financial second thoughts trace back to before she arrived there. She was, she says, “too conservative too early in my career. I focused heavily on saving and minimizing risk instead of fully appreciating the power of compounding growth — not just financially but personally and professionally.”

One prime example: “I chose not to take an opportunity to move to France for a role. In hindsight, that decision limited my exposure to new markets, perspectives and relationships that could have significantly accelerated my growth.” It would have been, she says, “far more valuable than the short-term financial security I prioritized.”

Matt Navarro is the global brand president of Stanley 1913, the supersize reusable tumblers with limited-edition color drops and a cult following. His financial regrets also date back to his school days: He regrets not investing in travel abroad when he was in college. “I could not see past the cost of money and time at the time. Many of my teammates and fraternity brothers studied abroad in Europe the spring of my junior year. Looking back, that was a huge miss on my part.” As a result, he didn’t get to experience other cities and countries until later in his life. “I realize that the experiences, perspectives and memories you get from seeing the world at that age are worth every single penny. It’s definitely a lesson learned on prioritizing experiences over a bank account balance.”

Fredrik Nilsson has helped turn licorice into big business at Lakrids by Johan Bülow A/S in Denmark, where he’s CEO. The indulgent chocolate-covered candies, in flavors like salted caramel and passion fruit, generated an annual revenue of 449 million kroner ($46.4 million) in 2025. It’s a real estate decision that has stayed with Nilsson. “When interest rates started rising [in 2022], me and my wife rushed to swap our apartment for a house north of Copenhagen before rates moved further up. I was convinced rates had already peaked after roughly doubling, so I chose not to lock in our mortgage for 10 years. Unfortunately, rates continued climbing dramatically.” In hindsight, “that decision has been a very expensive lesson in humility.”