What’s the
BIG IDEA?

Q&A

On inspiration

PF: You’ve founded and led several successful startup companies in a wide range of industries—from fitness to technology and banking. Where do you get your ideas, and how do you decide if you are going to go for it?

It’s kind of an obsession with making sure ideas I believe in actually happen. I’m very passionate about ideas that I believe can improve people’s lives, particularly in terms of helping them make better decisions. I’ve always been in that business. In technology, software and multimedia, it was about helping kids learn. Ask Jeeves was an Internet company that helped people use the Internet more effectively. Then Yoga Works was about how to present yoga, which is an ancient, obscure discipline, to a broader group of people so they don’t have to rely on drugs and surgery for their bodies’ aches and pains.

I get a thrill out of realizing ideas that seem absolutely right and should be in the world. Part of that is just the excitement of working with great people to accomplish them. In some ways, it’s about the challenge that no one believes you can really get something done.

PF: Have you always been that way?

RW: Probably. But I never thought I would be an entrepreneur. I was always consumed by great ideas and making sure that the best ones would win in the world. That’s what drove me. That probably comes from when I was a kid. My parents were both fairly tough, intellectual types. Also, my grandparents were both entrepreneurs in their own ways. One grandfather was an Indiana farmer who moved to Chicago and became a salesman in a pipe supply company. He eventually started his own business.

My other grandfather went to Hollywood and became a very successful song writer and succeeded in the world of entertainment. I got to see these two men and their different American success stories, so they were my inspiration for how to get things done.

PF: Do you deliberately sit down with the objective of brainstorming a new business idea, or do they just come to you?

RW: I think most of my ideas have kind of come from my own personal life transitions. I bring together unlike things, and then I come up with ideas that I think should be in the marketplace.

Down to business

PF: Once you have decided to pursue an idea, how do you get started?

RW: The first thing I do is put together a board of advisors because I always know that I’m stepping into areas I know nothing about. I try to find people who I think are equally interested and passionate and might know some part of what I’m going to step into. This way I have a group of people from whom I quickly learn. If they’re good and they like what I’m doing, they usually have a network of other people that they’ll introduce to me.

I also use the skills I learned as a journalist, which is to constantly track down the story. I always do the basic research and try to get all the data, and I always build a spreadsheet and try to create the business model for what I’m talking about. I learned that during my early career on Wall Street. I build high-level and detailed business models. Then I play around with how the business would actually work. It helps me sort out what the business will be and how we are going to make money.

And then the third thing I do is get it all down one page. It’s important to create your executive summary as a way to take your crazy ideas and tame them down. This helps you crystallize your thoughts. Then you can use those as tools to connect with people and say, “Listen, I’m thinking about a business that’s going to look at a new class of organic stapler covers, and here’s why I think they’re important.” Eventually I will write a detailed business plan to lay out all the aspects of the market, opportunity and the business, but my belief is that if you can’t say it and sell the idea in one page, then you don’t have a great business idea.

The green light

PF: How long does this process take?

RW: If I push hard, I can get it done in three to six months, and I always set a do or die date for new ideas. This takes the emotional energy out of deciding if you are going to pursue an idea or not. Once I get some wind in my sails around an idea I say, “OK, no later than three months from now I’m going to evaluate what I’ve done and decide whether I’m going to go to the next step.” Then I decide what the next step is, and I set a date for that.

I usually pick a location that’s not a traditional business location to make a big decision so we can sit down and be loose and flexible. We decide if we are feeling good about where we are and what our next steps will be. Sometimes it’s on a long hike by the ocean.

RW: Oh, yes. I had an idea that I wasn’t passionate about. I was doing it because I thought I should. Technically it sounded interesting, but it was not my passion. Three of us hammered away on this thing. We pitched it to different people, but it never quite hit home.

We kept thinking it would, and then we finally set a date. We met at a bar in the Mission area of San Francisco. I said, “At five o’clock we’ll start the discussion. We’ll give ourselves one hour to make a decision and one hour to celebrate the decision—one way or another.” And we decided no. We just didn’t have the conviction, the objective standard of truth or the emotional yes that we needed. At that point, we bought ourselves a round of mojitos and drank to the failure of our idea.

PF: Was that a relief or a disappointment?

RW: It was a total relief. We put our best in, and we were very clear about the criteria by which we would evaluate the idea. That’s the best we could have asked for. When you stop and say, “I’m done, and it’s OK. I gave it my best shot,” within a few weeks another idea pops up. It just happens because you’ve cleared your mind for the next one to come in. You’re not a failure—just a good entrepreneur.

The human factor

PF: How important are the people around you to the success of your business?

RW: One hundred percent. The quality of the people you work with is really important. They become like workout buddies—people who get you up when you’re coming down and energize and think through ideas with you. When you’re not working on one thing, they’re working on it. What ends up happening is you get that multiplier effect and you really get leverage on your idea. You bring complementary skills and create energy and momentum for pushing your idea to the next level, which builds incredible team morale.

You need to work with great people who have very special energy around startups because it takes a really particular group of people to be successful. They’re romantic and bull-headed. They’re all-purpose, they’re resilient and they’re always upbeat. Because if you’re around people who are depressed, nervous or suspicious that everything’s going to fall apart, it’s really hard to create good energy and momentum.

PF: How much of your success do you attribute to a positive attitude?

RW: When things have worked, it’s 100 percent. You want to go into business with the kind of people you want to have on really big, tough camping trips. When the bears eat your food and you’re three days out of civilization, you want someone with you who can make a fishing pole out of a piece of birch or pull trout out of the creek with their bare hands.

PF: It sounds like being an entrepreneur can be unnerving at times.

RW: It definitely can take you out of your comfort zone. Being an entrepreneur means having to deal with things you never thought you would have to do before, like payroll, employee taxes, dealing with landlords and pitching venture capitalists. That’s the art of being an entrepreneur—being willing and able to do things you’ve never done before.

PF: What’s your best advice for getting through the challenges of entrepreneurialism?

RW: When you’re doing it, you have to make it epic in your mind—you have to believe you are an epic hero and that you’re doing an idea because if you don’t, the world will miss out on it. You always have to create a story in your mind that you’re part of a very elite group of risk takers and change agents. And even if the idea fails, and even if you go back to your old job, you took that shot, and no one will ever take that away from you. Even if you sink a portion of your retirement savings and all of your friends say, “Oh, what a sad thing you did,” you will know you took the path least traveled, and you did the heroic thing, the hard thing. And then you can feel good about any outcome.