I considered making this lesson number one, if only because the right partner—or certainly the wrong one—will inform every stage of your journey as an entrepreneur. In Tiger 21, as part of each member’s annual Portfolio Defense, they are asked to share their list of the top 10 lessons they have learned so far. A common denominator is some version of the following exhortation: Marry the right person; it makes all the difference. “It wouldn’t have happened,” recalled one member who left a successful job to start a business with a very large personal loan, “if I hadn’t married a woman willing to take a risk. I know so many people who won’t let their husbands or wives take a risk to get ahead.”

Linda and Magid Abraham are a particularly inspiring example of marriage working well. Linda and Magid met in 1985 through work. Linda was a marketing analyst at Procter & Gamble, and Magid, who had recently gotten a PhD from MIT, was working for a consulting company that Procter & Gamble had hired. As Linda puts it: “Ours is a relationship steeped in very geeky data.”¹

By 1992 they were married, and three years later they started Paragren, their first company together. It provided software for customer relationship management, and Linda and Magid sold it within two years. Then they moved on to their next venture, ComScore, which is where their entrepreneurial efforts paid off.

Partnership in love and business worked for the Abrahams from the start. “We are very complementary,” says Linda. “He is very good at the strategic vision. And I am very good at commercializing. At knowing what the client needs. We are both very confident in what we’re good at and what we’re not good at.”

More than two decades later, they are still working together. After working side by side for 14 years together on ComScore, they are now working on Upskill, a platform for wearable software like Google Glass. And they’ve managed to raise four kids along the way. “He’s been my partner at every single step,” says Linda.

“We have a very natural rhythm,” Linda says of the way they’ve shared work and family responsibilities. “It’s always been very fluid. A lot of women are faced with the choice of being all in or all out,” she says of the decision to focus on children or continue to pursue an ambitious career. “I was in a very unique position to be able to do both.”

Some people don’t get it. “We get a lot of eyebrows raised at cocktail parties,” says Linda. But for this pair of entrepreneurs, it just works. “Rather than being harder, it’s made everything easier. I don’t know if I could have accomplished what I have without him. Our interests are always 100 percent aligned,” she says. “I don’t buy into the whole work/life balance thing. For me it’s just life.”

The Abrahams’ model is exceptional. Not many people find romantic and professional partnership in the same person. Most entrepreneurs I know have had a significant other who was willing to play a supporting role.

Robert Oringer’s wife, Marla, actually encouraged him to quit his very good job at IBM and go into business for himself. They were engaged to be married at the time, and Marla, who had started dating Robert when she was a teenager, had just finished her business degree and was planning to get a job in retail fashion. “I never envisioned myself being married to a company guy—all I knew were family businesses,” explains Marla, whose father owned a successful garment business in Montreal.² “Don’t you want to leave to do something else?” she asked Robert, well aware that starting his own business had been his goal since he’d switched his major at the Wharton School from accounting to entrepreneurial management. Robert said that he had planned to stay at IBM for five years. “Well, you’re approaching five,” Marla noted. “Don’t you think it’s enough?” Robert thought about it for a moment and then said, “Yeah, I think you’re right.”³

Robert began looking for a business to buy in New York or Montreal, and with the help of business brokers Marla’s father introduced him to, an opportunity turned up in Montreal. “Three weeks before the wedding,” Marla recalls, “Robert called and said, ‘I’m moving up to Montreal.’” A few days before the wedding, they bought the business with wedding gifts and a $70,000 loan from Marla’s father. “We got married, there was no honeymoon, just a couple of nights in a hotel in Montreal. And at the end of the weekend, Robert left for Vancouver on his first business trip. That was okay with me because I knew we were setting ourselves up. It was part of the whole process for me.” Marla was 22, married to an inexperienced entrepreneur with a struggling company and a loan. Robert remembers his state of mind at the time: He would wake up at night “scared to death.”

Marla didn’t know that, but Robert did share with her his plans for developing the business. In the meantime, Marla had quickly found and furnished an apartment for them and landed a job as a fashion buyer, which she liked. “I was pursuing my own career because it was my income that was supporting us,” she explained. She wanted a family but made it clear that she was willing to wait several years to start it in order to give her husband a chance to grow the business. “We lived modestly,” she says. “I wasn’t complaining. Our conversation was about building our life together. I saw my role as being supportive in any way, shape, or form to get us out of the gate.”

Above all, Marla saw herself as “a partner.” That partnership got much stronger—and more complicated—eight years later. By then, Robert was tasting some success as an entrepreneur, having merged his company with another company where he had developed a partnership with the two owners of the company his merged with.

After five good years as a buyer, Marla had quit to take over leadership of a division of her father’s company after the unexpected death of her uncle, who had been president of the division. “I was now selling to retailers, and the buyers liked me because they knew I had been a retailer too,” she recalls. She continued traveling for the company well into the eighth month of her first pregnancy, taking only a few months off after their first son, Cory, was born. When their second son, Justin, was born, Marla went back to work after just a few weeks.

When Justin was nine months old and Cory was three, both boys were diagnosed with diabetes within three weeks of each other. Marla was doing blood sugar tests throughout the nights, going to work exhausted, and still traveling one to two days a week. “It was not going well,” she confesses. “I knew I had to make some changes. So I turned off the lights in my office and told my dad and everybody in my division that I’d be back in a month.” But she never returned. “After a couple of days at home, as sad as I was not working, I was hit with the double reality that managing two young children with diabetes was a 24/7 endeavor, and that I needed to support Robert so that he could do what he needed to do to be successful. Our lives had changed.” As an entrepreneur selling diabetes-related products, Robert was well versed in what families were up against long before his children were diagnosed. His path now became very clear to him. It was, in his words, “To develop products to improve the lives of my children.”

While Robert refocused on breakthrough products and investments related to diabetes, Marla sat outside her kids’ nursery, pre-K, kindergarten, and elementary school classrooms, checking their sugar levels every half hour and advising their teachers on care. When the Oringers could afford household help, she trained and supervised them. “That was my job, seven days a week, my own little company of around-the-clock help,” she recalls. “And we discussed everything that Robert was doing in his business related to diabetes, so we were really partners.”

Marla’s advice to young couples starting out their lives with a partner who is trying to launch a business: “Somebody has to be grounded in that relationship in order to allow that entrepreneur to thrive. So at the beginning of our careers, I was the grounded one who had the stable job in Montreal. I was not making waves. I was there to be leaned upon. I was the support.” Marla clearly held up her side of the partnership: Cory is now working at Goldman Sachs in New York. Justin is at the University of Southern California pursuing his passion for the business side of music. And with the nest now empty, Marla has entered a new stage of her partnership with Robert. “I was always a partner in his investments,” she explains. “But now I’m traveling with him, going to meetings with the founders of diabetes-focused startups, socializing with other potential co-investors, and being introduced as ‘partner.’ Up to now I’ve always been his support, but now he’s helping me find my new passion.”

Robert has helped Marla take her work with diabetes-related projects to a global scale. In the fall of 2015, she joined the Leadership Council of Beyond Type 1, a new California-based nonprofit creating programs and innovations to help people with diabetes around the world thrive. “The goal is also to change the conversation about diabetes and make people aware of what people living with diabetes have to deal with day to day,” explains Marla, who will be buying and sourcing all of Beyond Type 1’s branded merchandise. In September 2015, she also began advising on the public relations and social media efforts for The Human Trial, a documentary film following the efforts of a company that is searching for a cure for diabetes.

Rick Gornto (Lesson 7) and his wife, Janice, began their entrepreneurial journey a generation before the Oringers; they have been married for 45 years. When they met, Rick was 25 and had just taken some time off from his first semester of law school to recover from breaking his neck skydiving. While recovering, he met a devout Christian who was such a good guy that Rick decided he wanted to be just like him. Rick became a churchgoer—and then his mentor introduced him to his niece. “I like to say,” Rick says, “that at age 25, I met the two Js–Jesus and Janice, who have been very good for me.”⁴

“We started from scratch,” he recalls. “I mean, we had nothing.” But Rick’s belief in himself, and Janice’s faith that he would succeed, amazingly, turned out to be all they needed. “I was so naïve and trusting,” recalls Janice, laughing at her twenty-something self, just out of college with a degree in speech therapy, newly married, and soon to be a mother. “It didn’t start out so well,” she confesses.⁵ At first, Rick had trouble finding and keeping a job. Then he grabbed an opportunity with an insurance company in a suburb of Houston, moving there while Janice was pregnant with their second child. “It was kind of crazy,” she admits, noting that Rick was not getting a regular salary: “It was commission only.”

But Rick quickly proved to be a natural salesman, the commissions increased, and so did his confidence in his business abilities. “Rick was such a go-getter and self-motivator,” marvels Janice, conceding that by nature she was way more cautious and analytical, just the kind of person Rick needed to balance out his attention deficit disorder and impulsive nature. With Janice as his anchor—“I’m always keeping him on track,” she says—Rick’s reputation as a talented insurance salesman spread. He soon became a partner in another insurance company in town and began saving for his next move. Janice considered returning to school to become a nurse but quickly realized that Rick’s work was becoming too unpredictable for her to take a regular job. “Someone like Rick, eager to run his own businesses, needs a partner who can turn on a dime,” she explains. “He might call me from work on a Monday and say, ‘We’re going to Hawaii on Friday. There’s this meeting; we’ve got to be there.’ I had to immediately find a sitter to take care of the kids and get going. If I had a career, I wouldn’t have been able to do things like that.”

In retrospect, Janice has trouble believing how trusting she was. “If my daughter came to me and said, ‘My husband wants to quit his job and take a commission-only job, and I’m pregnant, and we’re moving,’” I’d be saying, “‘Are you crazy?’” Then she laughs: “And so the moral of that story is that sometimes you just have to be young and stupid.”

Or very, very optimistic, which, as I’ve noted, is an essential trait of the successful entrepreneur. (And let me quickly add that not all the entrepreneurs I know have had marriages as successful as the Abrahams, Gorntos, and Oringers.) For Janice, sharing a life with an entrepreneur requires one trait above all: “You have to be flexible.” She has no regrets and would recommend the entrepreneur’s life to anyone who sought her advice: “You will have an exciting life,” she says. “You’ll meet lots of people, go to lots of places, and life will never be dull for you.” Amen to that.

As I tried to frame the takeaway here, I was reminded that my own good fortune is similar to Rick’s and Robert’s, in that my wife of 40 years has also gone along with an ever-changing entrepreneurial life. Katja came from an extremely successful real estate family. If I had lost everything along the way, our kids would never have starved. This allowed me to take risks I might otherwise have thought long and hard about. Like Marla Oringer, Katja also understood the life of the entrepreneur in a fundamental way, having grown up with a father who was his own boss and suffered some significant ups and downs along the way.

When I had to drop everything for a deal or something related to a business I owned, my wife has been, in a thousand ways, more flexible and tolerant than most other wives would be, for which I am forever grateful. (Family emergencies still come first, and so do major life events, most of the time.)

For Rick, Robert, and me, the model was pretty conventional. Our wives played critical support roles, often doing most of the day-to-day work of raising a family and running a home. That career isn’t paid, but it can be just as taxing as running any business. Yet this is only one way of doing things—there are clearly other ways to make family, marriage, and entrepreneurship work. Linda and Magid are an important example of a different type of partnership.

I’ll close with this warning: Once you’ve committed to the entrepreneur’s journey, you should think twice about forming a lifelong relationship with someone who isn’t prepared to be supportive or, worse still, whose emotional or personal needs will prevent you from having the flexibility and capacity required to weather the inevitable storms that will arise throughout your career. If you possibly can, choose someone who is prepared to be your partner in every way.