Most of the successful entrepreneurs I have known—including the guy I look at in the mirror—have a tendency to overrate their personal skills and wisdom. One of the great benefits of meeting confidentially with a group of peers is learning how much you don’t know—month after month, year after year.

All too often, entrepreneurs are experts at one or two things, but they don’t have a clue about the rest. Creating and growing a business requires a broad set of talents and skills. Those who dare to do it without plugging the holes in their skill sets are only increasing their already high odds of failure. Some of us learned this lesson the hard way, while others were lucky enough to make good hiring choices along the way. The smartest among us acknowledged our weaknesses at the outset and made sure we had a team in place whose talents made up for them, even before we launched our companies.

Over the course of Pete Settle’s career, he came to recognize that he was not a happy administrator. “Everybody is defective in some way,” he notes. “The best thing I did as a leader was finding people who could complement my weaknesses, which are many.”¹ Pete managed his family’s school bus company and then worked as a top executive for the large public company they sold it to. When he started his own company, the first thing he did was hire his older brother Mike as his chief operating officer.

“We have very complementary skill sets. I was the one who would go out and make promises to the clients about what we could do for them, and Mike would keep those promises.” In 2012, Pete sold the company to the National Express Group, a British multinational transport company, which is now the number two provider of school bus services in North America. After a few years as CEO of National Express’s North American transit operations, Pete tired of his administrative responsibilities and moved on. Mike stayed and is currently the senior vice president for the company’s operations in Ohio, Pennsylvania, and Michigan.

Some people discover their talents as entrepreneurs and dealmakers when they join forces with people with very different skills. Take my old friend Richard Block, who graduated from college in the early 1960s and went to work for Westvaco (the Fortune 500 paper company). Richard became the youngest sales manager in the company’s history, and in 1967 he was transferred to Chicago.² Months before returning to New York in 1970, Richard heard a rumor that a small printing company was about to acquire one of his biggest customers. A proactive salesman, he went to visit the small company to see what the real story was.

He met that company’s cost estimator, Don Kosterka, and made a real connection. Don was well schooled in the printing business but didn’t like the direction his company was going. Over subsequent meetings, he told Richard about the company he was planning to start, which would not only print record album jackets but design them too. He introduced Richard to his secret weapon, Jim Ladwig, a Grammy-nominated art director who was then at Mercury Records. A short while later, Don and Jim quit their jobs and launched Album Graphics Inc.

Six months later, Richard was back in New York settling into the next job on the ladder of Westvaco. But working for a big company had finally started to lose its appeal.

Back in Chicago, Don and Jim’s new company was up and running, and they were ready for a sales partner. Their first choice was the genius who got Andy Warhol to work with the Rolling Stones on the jacket for their Sticky Fingers album, which was instantly iconic because it featured a real, working zipper on a photo of a pair of jeans. Their prospective partner overplayed his hand by asking for half the equity of the company. (No wonder you hear the expression, “Bulls make money, bears make money, but pigs get slaughtered.”)

“Don was a manufacturing genius, and Jim was a creative genius,” Richard says. Richard claims his own main achievements in college had been on the football field, but Don and Jim needed an ambitious young salesman to round out the partnership and Richard met all their expectations. Plus, he asked to earn only 15 percent of the equity out of future profits. It was early days at Album Graphics, but they made a pivotal deal with Polygram Records, and within three years Richard and his partners were producing album jackets for almost every other major label. Even though Richard was based in New York and his partners lived in Chicago, “We talked every day on the phone about everything,” Richard recalls. “It was an incredible gearing of talents. We never got in each other’s way.”

“No printer offered high-quality design previously. That disrupted the business model,” Richard continues. “The best-selling artists wanted to control their own album art, so they came to us.” The trio’s timing couldn’t have been better. The British Invasion and the 1969 Woodstock Festival powered the music business into the next decade and beyond. Jim’s stable of innovative art directors and designers appealed to the aesthetic tastes of many of the best-selling bands.

Seventeen exciting years passed. Don and Jim believed the company had reached its maximum growth potential, and they were ready to sell. Richard disagreed, so with the help of private equity investors and a big bank loan, he bought them out. Don sold 90 percent of his stock, and Jim sold all of his, but Richard stayed close to both of them. Jim had sold out, in part, because he thought the company needed to be managed from Chicago, and even though Richard promised to commute three days a week from New York, Jim thought it wasn’t enough. Despite that, Jim stayed on as head designer, but with no equity exposure. Over the next 13 years, Jim and his team racked up another string of Grammy nominations and awards.

Growth always seems to create unexpected challenges. Most major artists released their big albums in the fall, which meant that for the first eight months of the year, Richard’s factories were grossly underutilized. Being a great entrepreneur, Richard chose to see this problem as an opportunity. To utilize that excess capacity, he diversified into new contra-cyclical categories, printing high-quality packaging for liquor and cosmetic companies, such as Avon, L’Oréal, and Estee Lauder, during the first months of each year. At its peak, Richard’s company, rebranded AGI, was running 17 printing plants (many adjacent to the major labels’ record pressing plants and, later, their CD pressing plants). Getting there wasn’t easy, and it was especially challenging to figure out how to lure really high-quality customers from completely different industries to balance the factory load throughout the year. It took almost a year to get a first sales visit to Avon, for example. At the time, Avon had nine suppliers in the category Richard was pitching business for. Seven years later there was just one, and it was AGI.

Under Richard’s leadership after Richard’s buyout of his original partners, sales went from $35 million in 1987 to $325 million in 2000. “I loved the company and didn’t want to sell,” Richard confesses now, noting that in the ensuing years he turned down multiple offers from one of the nation’s biggest paper companies. But eventually, his investors and employee shareholders were ready. In 2000, Richard finally agreed to sell the company—to MeadWestvaco, the latest manifestation of the company he had worked for in the 1960s when he first met his partners.

Richard is a sensitive guy. To this day, it weighs heavily on him that Don and Jim didn’t participate so much in that grand finale. Nonetheless, it was a point of deep pride to him that Don’s 10 percent was worth more in 2000 at the time of the next sale than the 90 percent he’d sold in 1987.

And even though Don and Jim sold almost all their interests before the period when the most value was created, Richard gives his initial partners plenty of credit for that later success. “It might have never happened for me,” Richard insists. “I believe the magic bullet was in the amazing synchronization between the three of us. Even after they dropped out, that quality of meshing for the common good at the company continued. It had become our DNA. Another astonishing thought is that had a simple spontaneous decision I made—to visit that little printer who was acquiring one of my customers—not been made, I would not have been part of this story.”

That kind of magic is often available to entrepreneurs who surround themselves with people who are smarter than they are—or who at least have the skills that they themselves are short on.