He spent his family’s life savings on a hot dog trailer — and later cashed out for $1 billion. He still regrets it

By 2014, Portillo’s had 38 locations across four states, generated roughly $300 million in annual revenue and carried no debt. Portillo also owned the entire business himself.

Those numbers attracted plenty of attention from private equity. Portillo ultimately sold the company to Berkshire Partners in 2014, pocketing nearly $1 billion, according to Forbes.

“I’m sorry I sold,” Portillo told Forbes. “I didn’t owe 10 cents to anybody.”

He acknowledged that the timing made sense. Twenty-four private equity groups were interested in buying the company, giving him an opportunity to cash out after more than 50 years of building it.

But walking away proved harder than expected.

Perhaps that helps explain why Portillo didn’t retire after the sale. He spent more than $100 million buying back the land and buildings housing 20 Portillo’s restaurants and commissaries, then leased them back to the chain under 20-year agreements.

He went on to invest in strip malls, industrial properties, apartments, restaurants, stocks and other financial assets. Forbes now estimates his fortune at more than $1 billion.

None of it changed how he felt about selling the company.

“Portillo’s was fun. A lot of work, my God, the hours and the sacrifices,” he said.

Although Portillo built his wealth through tremendous work ethic and a concentrated bet on his own business, holding on to it has required a very different mindset.

The risk-taker became a conservative investor

For a man who risked $1,100 of his family’s savings to open a hot dog stand, Portillo has been surprisingly conservative with his money since selling the business. As Forbes reported, 63% of his portfolio is now allocated to bonds, compared with just 22% in stocks and the remaining 15% in other investments, including private equity.

Even his more than $100 million bet on real estate was part of a broader effort to spread his wealth around.

“You never want to put all your eggs in one basket,” he said.

Although Portillo’s wealth is extreme, his shift from entrepreneur to conservative investor isn’t unusual. Entrepreneurs often build their fortunes through a concentrated bet on a single company. Selling the business gives them an opportunity to diversify and shift their focus from building wealth to preserving it.

According to UBS, entrepreneurs often become more cautious with their money after exiting their companies as protecting what they’ve built takes on greater importance.