Optimism fuels the entrepreneur’s journey past the naysayers. Self-control is a psychological mechanism for beating off temptations that seem irresistible, at least at the moment. But given the high failure rate for startups, successful entrepreneurs typically struggle for a decade or more to build a business that just might eventually appeal to a buyer. To keep struggling requires an additional psychological trait: grit. Angela Duckworth and her colleague James Gross define grit as “having and working assiduously toward a single challenging superordinate goal through thick and thin, on a timescale of years or even decades.”¹

Duckworth’s research into the psychological factors affecting achievement has enabled her to predict which teachers and students will succeed in tough inner-city public schools, who will survive the notorious cadet summer training before the first term at West Point, and which candidates will ultimately make it into the U.S. Army’s Special Forces, regardless of IQ, standardized test scores, or even physical fitness.²

Duckworth has not studied entrepreneurs, but her definition of grit pretty much summarizes most of the successful entrepreneurs I’ve listened to over the past two decades. Almost every one of them has faced moments of crisis when the businesses they were building suddenly cratered. Each of them coolly reviewed the situation, came up with a plan of attack, pressed their grit buttons, and spent the next several years revamping their operations into enterprises valued at tens of millions of dollars and more.

Take Ed Doherty, for example.³ Ed was born in Brooklyn and raised by a single mother who worked as a housekeeper and bookkeeper until she’d saved enough money to buy a deli on Long Island. Ed worked there for 40 hours a week during high school and college and 60 hours a week during the summer.

By 1973, Ed was working in the real estate division of Burger King, selecting sites for new restaurants on the East Coast, when he got a call from Marriott, which was looking for someone to do the same for their fast-food restaurants. “You have a good reputation,” said the man from Marriott, offering him $25,000 a year. Ed was already making $24,000, so he figured he was in a position to make a counterproposal: $26,000. “If he said yes, I’d take the job. If he said no, I’d stay with Burger King,” he recalled.

Ed got his bump in salary. During the next five years, he became a maestro of site selection and was promoted to the number-two position in Marriott’s restaurant real estate division. He soon requested a transfer to operations, where he ran a third of the Roy Rogers restaurants in the New York metro area. Then, in 1984, he took an even bigger step up the corporate ladder when he was promoted to general manager and vice president in Marriott’s Washington, DC, headquarters, running Big Boy Restaurants of America, which had 1,200 locations. He and his wife, Joan, who had just given birth to their third child, found a house they liked in the DC area.

While his wife was preparing for the move, Ed started working at headquarters and quickly realized that his talent as a manager would do him no good in a culture where some executives tried to win favor by sabotaging others. Ed was making more money than he had ever dreamed of. Even so, he called Joan in New Jersey and told her to put the move on hold. “We’ve got to figure something out.”

In fact, Ed already had figured it out. He wanted to buy the 19 Roy Rogers restaurants that had been his responsibility before his promotion. They each averaged $640,000 in total annual sales and lost $700,000. “I thought I could turn them around.” He persuaded Marriott CEO, Richard Marriott, to sell him the restaurants for a million dollars and quickly found a bank that would give him a personal loan for the money. Then he and his wife had the hardest conversation of all. “I said to her,” Ed recalls, ‘Okay, honey, I’m going to give up this job making $200,000, we have a mortgage on the house, and I’m going to borrow a million dollars personally. And we won’t have a salary for a period of time. But this is an opportunity to control our destiny.’ ” Fortunately, she gave him the green light.

Over the next five years, Ed’s new regime doubled the restaurants’ annual average sales. He borrowed more money to add another nine Roy Rogers franchises to his stable and then made a deal with TJ Cinnamons to buy six bakery cafés. “Life was good,” recalls Ed.

Then, it was not so good. In 1990, as part of a long-term strategic plan, Marriott decided to exit the fast-food restaurant business, selling its Big Boy and Roy Rogers operations to Hardee’s. In Ed’s opinion, the new owners “destroyed the Roy Rogers brand” over the next three years. Ed owed $4.5 million to banks and “saw it all going down the tubes.” And then he did what every successful entrepreneur I know does when hitting a wall. “I didn’t blame myself,” Ed explains. “I didn’t blame anybody. I just said, ‘I’ve got a problem. I’ve got to develop a plan, work the plan, and if it’s the right plan, I will come out of this successfully.’” In other words, he pushed his grit button.

He asked his bank to restructure his loan, but they refused because they only take that step once borrowers are delinquent. Ed quickly solved that problem because he had no choice but to stop making his loan payments. As he was nearly out of money, the decision was easy. He also had to stop paying royalties to Hardee’s. “I couldn’t afford to pay the loans and the royalties and my employees,” he explains. “My people come first.” He then hired the best lawyers he could find to help him renegotiate deals with Hardee’s and his bankers, which he was able to do without declaring bankruptcy.

Over the next few years, Ed continued to sell his leases while persuading the bank to reduce his loan to $3 million and convincing Hardee’s to forgive his royalty payments. In less than a year he had the $3 million to pay off the loan, which wasn’t even due for another four years. Proving to be a very persuasive fellow, Ed talked the bank into reducing the loan by another $700,000. “Cash is better than waiting for something,” he rationalized.

With enough money to stay in business, most owners would have stuck to their knitting. Ed, however, began looking for his next opportunity. He liked the Applebee’s brand, which was expanding in the east. The company resisted. Ed didn’t have the net worth to qualify as an Applebee’s franchisee. But he persisted: “Isn’t there some way we can work around this?”

The company agreed to work with him, and Ed opened his first two Applebee’s restaurants in New Jersey in 1993. Meanwhile, he was selling off his Roy Rogers locations, paying off his bank loan—and looking for more opportunities. He found six locations that he thought would work for Wendy’s. He contacted the Wendy’s corporate office to ask about converting his existing Roy Rogers restaurants. He wondered if they would lend him the money because his bank wouldn’t. Wendy’s agreed, mainly because they were already considering buying 150 Roy Rogers New Jersey and Long Island locations from Hardee’s and rebranding them as Wendy’s. Ed had offered them a quick test case. He converted three of his Roy Rogers sites into Wendy’s restaurants, and his sales tripled. In 1995, he built two more Applebee’s restaurants and converted his three remaining Roy Rogers locations into Wendy’s restaurants.

In three years, Ed had gone from the verge of bankruptcy to success. Six years later, he had 10 Wendy’s franchises and valuable experience. He had learned that his success—and his family’s future—depended in large part on the success of his franchiser. That didn’t sit well with him, so he decided to sell his Wendy’s restaurants in order “to put enough money in our pocket that our family would never have to worry again.”

Ed, 69, is doing fine. The company he heads, Doherty Enterprises, now owns and operates 107 Applebee’s restaurants, 43 Panera Bread cafes, and has also developed two Irish pubs and two wine bars. At the time I spoke to him in 2016, he expected yearly sales of $500 million. “It was all luck,” says Ed with a shrug that has won the hearts, minds, and cash of many bankers.

That kind of hard-won luck is a common denominator in the careers of many members of Tiger 21, but occasionally we hear stories that move even the toughest among us. When Rick Bennett joined Tiger 21and told his story to his fellow members in Austin, Texas, during one of his early meetings, he was welcomed as someone they knew quite well—the partner in a successful wealth management company who made money making look easy. Their perception changed, however, once Rick told the story of what it took to make his way into our network.⁴

Twenty years earlier, as Rick and his partner were starting their business, Rick’s marriage fell apart. The divorce was messier than most and, as if that weren’t enough to derail Rick from the single-minded focus and effort required in the early stages of any new business, he soon learned that his former wife would be unable to share in joint custody of their three young children. Rick would be a single parent.

He had to make a stark choice between the future of his new business and his children. He went to his business partner with his decision. “I take care of things. I don’t drop things in my life, and I’m not going to drop the kids.” They were his first priority; his health was his second. “If something gets dropped, it’s going to be work. So we have to figure out a way that I can have some flexibility to go to school events and do what I need to do.”

They worked it out, and Rick proceeded to do what he needed to do, which was to divide his life between building the business and taking care of his kids. For the next two decades, he pulled off an impressive balancing act, helping with their homework, having their friends over at his house, and traveling with them—all while advancing the company. He made a conscious choice to not remarry. He had some relationships, but he never brought anyone into the house.

When Rick told his story, “There was absolute silence in the room as the magnitude of the challenges he faced poured out,” recalls Chris Ryan, who chairs the Austin chapter of Tiger 21. “The respect in that room for Rick—you could feel it.”

Rick shrugs off those 20 years of resilience. “I didn’t agonize over it or feel sorry for myself,” he said, echoing Ed Doherty. “I just did it. I not only did it, I enjoyed it.”

I suspect that one of the reasons Rick’s story grabbed that room so tightly was that many of us were able to apply our customary grit only because we had an understanding, flexible significant other taking care of business at home. The other members were no doubt wondering whether they could have pulled it off as a single parent. Candice Carpenter Olson wouldn’t have been wondering. She’s another person who did it. Indeed, when I think about the grittiest entrepreneurs I know, Candice Carpenter Olson leaps to mind.

In the early 1990s, Candice was a highly ambitious, successful woman in Manhattan. She had already had an extremely impressive career in the corporate world. By the time she was 40, she’d been a vice president at American Express, the president of Time-Life Video, and the president of Q2, a high-end version of QVC that she built with Barry Diller. She gained a reputation for being tough enough to stand up to him, though she claims she felt like hiding under the desk most days.

She realized how desperate she was to be her own boss when, on the way to interviews with various corporations, she would get sick to her stomach and actually throw up. “There couldn’t have been a clearer sign,” she said. “I had to strike out on my own.”⁵

At that time, the Internet was just beginning to emerge into the public consciousness, and Candice, who had been advising one of the top executives at AOL, saw a huge opportunity to create an online network targeted at women. As a single woman, Candice knew how hard it was to find the right partner. She was dating a lot, but she couldn’t find anyone worth committing to.

“We were full of religious fervor about the idea,” she says. But investors didn’t get the concept at first. “They would look at me and say, ‘Women won’t ever use the Internet.’” It sounds laughable now, but at the time it was the conventional wisdom.

She tuned out the naysayers and forged ahead. In 1995, Candice founded iVillage. By 1999, the company was worth $2 billion.

While she was doing all this, Candice was also a single mother to a toddler. She had decided it was better to start a family on her own than to settle for the wrong partner. The fact that she was able to create a successful startup while she entered motherhood as a single parent is something that many people can’t quite believe.

Candice knew that when an entrepreneur chooses the wrong mate, the results—both personal and professional—are disastrous. “Entrepreneurs are artists, and they need the emotional support an artist needs,” she says. “A CEO is lonely. An entrepreneur CEO is even more lonely. But a female entrepreneur CEO with a kid? That was sort of one of a kind.”

It was tough, she admits, but she found a way to make it work. She hired a student cook who would prepare dinner every night for her and her young daughter. “I’d go rushing home at six o’clock and skid into my seat at the dinner table. Then, I would spend a few hours with my daughter, completely present. The minute I put her to bed, asleep beside me, I would whip out my computer and work until midnight or later. It was very intense, but I wouldn’t have done it any other way. Now my daughter is starting her first company at 22.”

The coda to Candice’s story is equally unexpected: Within two years of stepping down as CEO of iVillage in 2000, she met her husband, Peter, the head of Random House at the time. Together, their family has seven children, three adopted from Eastern Europe. Both Candice and Peter are currently working on new companies of their own.

I’m sure Candice would agree with Rick’s assessment of pulling off entrepreneurship as a single parent: “If it were easy, everyone would be doing it.” That’s something that every entrepreneur struggling to grind it out should memorize.