Hall of Fame footballer Ronnie Lott is sitting in front of a classroom, lecturing a small group of fellow players about the importance of learning the playbook. A blackboard hangs behind him. Florescent lights flicker overhead. The players nod eagerly as he talks. A coach sits nearby.

Lott, a former safety, was known in his playing days as one of the National Football League’s hardest hitters. He shows that same intensity as he talks — leaning forward, gesticulating and peppering the players with questions. But the playbook that he is discussing has nothing to do with running and tackling. His audience isn’t seated in a locker room but rather in a classroom at Wharton West, the school’s campus in San Francisco. And the coach isn’t wearing a whistle or brightly colored synthetic shorts. In fact, in this particular session, she is wearing a skirt.  

Lott is counseling a group of current and former NFL players on making the transition from pro football to business. “When you leave football, it’s going to be like you’re a rookie again,” he says. “You are going to have to close the NFL playbook and open up and learn a new one” in the business world.

He has come to teach these players as part of a year-long Wharton Executive Education program called “Entrepreneurial Management: Transitioning with Success,” organized by the Wharton Sports Business Initiative (WSBI) and sponsored by the NFL and the NFL Players Association. The program offers business education to NFL athletes, focusing on everything from financial analysis and entrepreneurship to real estate development and stock market investing. Lott’s talk is one of the follow-up sessions that are a key part of the program, which began in April with three days of classes in Philadelphia and is scheduled to run next spring as well.

The follow-up small-group meetings, happening on both the East and West coasts, allow the players to work closely with business people and Wharton professors to expand their business knowledge and plot out their post-NFL careers. “What I liked was that it was just two of us, another player and me,” says N.D. Kalu, a Philadelphia Eagle who attended one of the sessions at Wharton’s main campus. “We got a chance to ask every question that we had. And [Wharton real estate professor] Peter Linneman could go into his answers in depth. He told us about multimillion-dollar real estate projects that he’d been involved with, and then he answered questions about my projects.” Kalu lives in Texas during the off-season and owns a real estate company there. 

These sessions cement the lessons from the lectures that the players attended during their initial stint in Philadelphia, says Ken Shropshire, WSBI director and a legal studies and business ethics professor. “It’s a formalized way to ensure continued learning, rather than hoping that the players continue to address these issues themselves.” Plus, the smaller meetings give the players the freedom to explore their personal situations and business goals in a way that might feel awkward in a large group.

Some of the sessions have been more informal than Lott’s — more like mentoring than lecturing. Mori Taheripour, a WSBI associate director who has led several sessions on the West coast, sees her role partly as “just being there to help and listen. I’ll open doors for them — refer them to an attorney or a faculty member. The coaches are there to make the players’ journey easier.”

Among those who spoke to the players during the three-day program in April were Wharton alumni Jon Huntsman, founder and chairman of Huntsman Corp., and Lew Platt, who was former chairman and CEO of Hewlett-Packard, CEO of Kendall Jackson Wine Estate and chairman of Boeing before his death two weeks ago at age 64. Platt, who had a “true passion for fantasy football and was a big San Francisco ’49ers fan,” was already a mentor for several of the players and had planned to take part in a reception next February as part of the program follow-up, says Shropshire.

Framing Their Options

Jon Runyan, who also plays for the Eagles, sat down in Philadelphia with Shropshire and Georgette Poindexter, a Wharton real estate professor, to discuss real estate investments as well as how he might transition into broadcasting. “As you get older, you realize that this isn’t going to last forever and you are going to have to move on.” Runyan has played in the NFL for a decade.

The Wharton program, he says, has helped him frame his future options in ways he hadn’t previously considered. “The presenters give you ideas like trying to leverage your name and get into a partnership with as little money down as possible. That’s something I never thought about.”

In keeping with the less-formal approach in the follow-up sessions, Lott’s talk in San Francisco was structured as a conversation with David Pottruck, a Wharton alumnus and former co-chief executive of Charles Schwab Corp. In response to questions from Pottruck, Lott described his move from pro player to entrepreneur, including his mistakes. Lott and partners Harris Barton and Joe Montana, both former teammates on the San Francisco 49ers, own Champion Ventures, a venture capital firm. Lott also invests personally in a variety of businesses, including car dealerships.

He started his talk by admitting that he stumbled in his first venture. That was back in 1981, and he was a rookie. He decided to launch an amusement business. He bought a Pacman machine and persuaded an acquaintance to let him put it in his hotel. That machine led to several others. “I soon recognized that we were going to fail,” he says. “Pacman was special when we bought it, but a year later, Space Invaders arrived, and it was the special game.” Space Invaders gobbled up Lott’s business just like Pacman used to eat those little flashing dots and cherries. One consolation: Lott still has one of the Pacman machines in his house.

An early foray into real estate didn’t work much better. A graduate of the University of Southern California, Lott began by buying a piece of property in Los Angeles. At the time, the real estate market there was booming, and he saw a quick gain. “In 1989, I bought another, flipped it and made a pretty good profit,” he recalls. That led him to think he could build and sell a high-end home, even though a friend in the real-estate business advised against it. “I was sure I knew what I was doing,” he says. He lost $1 million. “I thought the market was easy. I didn’t do the preparation, and preparation saves you money. There are experts out there who will help you, but you have to be willing to open the Yellow Pages to find them.”

Preparation means studying your chosen field, finding good mentors and partners and understanding the ways in which the business world resembles football and, more critically, the ways in which it differs, he says. “When you play football, you play four quarters, and there’s an outcome. In business, you don’t get a scorecard. We had an event at our car dealership this morning. What’s the outcome of that? Did we win or lose? I know now that we won today. But how do I know that? In business, I had to learn a new lingo, a new way of keeping score.” 

Another difference in the business world is that people don’t cheer for you as they did when you played sports, says Pottruck, who was a football player and wrestler while a student. “In business, you can’t throw the ball down and spike it. You’ve got to find new ways to feel good about your success.”

Asking the Tough Questions

A paradox of being a professional athlete is that you are expected to work hard and show an intense commitment on the field but you are also pampered off it, with a retinue of people catering to your needs, Lott says. In addition, the bravado and macho posturing that are part of football often inhibit players from admitting their ignorance. “We’re afraid to ask the tough questions, the ones that we don’t know the answers to. We’re champions over here in football so it’s like, ‘How am I going to be vulnerable over here [in business]?'”

If you are willing to ask, many people, including executives at big companies, are happy to share their experiences, including their failures, Lott says. Even during the season, crammed with games, travel and video-review sessions, players have a chance to meet people who might be able to help them make the transition to their post-football careers.

“What are you doing on Tuesdays?” the NFL day-off during the season, Lott asks the players gathered in the Wharton West classroom. “You could go and see guys who have been successful in business and buy them a cup of coffee. In football, on the field, we watch everybody. In business, you have to observe everybody too. You have to see how they do what they do.”

Likewise, players need to tap into the alumni networks at their alma maters. Fellow alums who have gone into business are typically happy to chat with former college athletes who have reached the pros, he notes. Their help can be especially valuable once an athlete has written a business plan or started a company. “Tell them, ‘We’ve got a business, and we’d like you to tell us what we’re doing wrong. Chew holes in it.'”

Here, Pottruck jumps in. Unlike sports, he says, if you want to become a successful businessperson, you also have to acknowledge the possibility that your venture might fail, then make contingency plans. That can be tough for top athletes to do because they have been taught since grade school to focus only on success — to visualize winning. “One of the things that you always have to think about in business is risk management. You are taking capital from your investors. You have to explain the risks to them. You have to manage the risk, the downside. That’s part of every investment — what happens if it doesn’t go well?” Managing the downside can mean sharing the risk among an appropriately large number of investors or figuring out a way to salvage some of your investment if a project craters. 

A way to make failure less likely is to pick good partners, which some former pro players have difficulty doing, Lott says. Rather than selecting yes-men, pick smart people who complement your skills. “In football, we spend a lot of time looking at the draft, looking for the best player. When we get a business partner, we don’t expend that kind of energy. And you have to understand the what-ifs. What if something happens to you? What if something happens to him? In sports, we know each other for maybe four or five years. In business you’ve got to think it’s 10 to 15 years.”

Lott’s final piece of advice to the players was as much about handling the ups and downs of life as it was about transitioning from football or learning about business. “I have interviewed a bunch of guys at the end of their football careers, after they have been cut,” he says. “And they have been like, ‘How could they have treated me that way?’ They have got this hole in their stomach. But when they started out in football, they were excited every day.”

The key to a successful transition to a new career is keeping that youthful zeal and channeling it into your next venture, whatever it is, he adds. “When I was young, I had enthusiasm every day, not just for football, but for life. You’ve got to keep that…. My dad was in the military for 25 years and then he worked for the Post Office for 10 years. Now he’s working at a boys’ ranch. I said to him, ‘What are you doing? You don’t have to do that. Why don’t you take it easy?’ And he said, ‘You know me. You know I’ve got to make a difference.'”