Meet Andy Dunn, the Founder of Bonobos Inc., who at 28 took the risky but fruitful journey to prove that clothing brands can be built by e-commerce. Even now, with the largest apparel brand ever built on the web in the United States, Andy still remembers the days he used to receive “pity looks” when he described his idea.

IVY Magazine sat down with Andy to hear his greatest advice on how to create an empire out of thin air.

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Become the Chief Praise Officer

The most important advice I’ve ever received came a few years ago from Joel Peterson, Chairman at JetBlue and a founding Angel investor of Bonobos. At the time, I was pretty down on myself; my Co-Founder had just left, and a year later, I thought the company might fail. I was worried that the narrative of the company would be: Bonobos screwed it up and lost the wrong guy. I felt low and I was transmitting that to our team, which was making it worse.

I told Joel that I didn’t understand what to do. What was my job? How could I inspire people? Joel said there were two ways I could do it: with carrots or with sticks. Both could be effective, but the stick was about fear and the carrot was about recognition. In other words, I could either build a fear-driven culture or a recognition-driven culture.

Here’s the piece of advice that changed everything: he told me that there are no diminishing returns on specific positive feedback. Instead of saying ‘good job,’ Joel told me to start saying why someone did a good job. Be really passionate about connecting your praise to the ‘why,’ and do it with as much time and energy as you can. By praising good behavior, you’ll create an environment where people are leaning in to that behavior. It’s like parenting. When a child acts out, ignore him; when the child does something good, reinforce that behavior. It might sound paternalistic, but it’s what great leaders do. Become the Chief Praise Officer, and in so doing you will not only inspire people to do great work, but you’ll feel better about what you do. Your job will be to give thanks and express gratitude and recognize others. Then it becomes a pretty fun job. Joel was absolutely right.

It’s hard to find the energy and show up in that way when your company is struggling. But I thought back to my own previous jobs, working in private equity and consulting, where my bosses withheld praise and made us operate on fear. One boss once told me my job was to be neurotic. I used to think I had to embody that as a CEO, but it wasn’t true. I could be myself. If I have any advice, it’s to show up as a positive person. It saved our company, not only for the people who worked here, but for me, too.

Balance being a CEO and a Founder 

“CEO” and “Founder” are two contradictory roles. Being a Founder is about being driven to distraction by the world, so much so that you need to put something new into the world to satisfy your curiosity and your ambition. By definition it’s an act of rebellion.

The problem is that if your act of rebellion works, and becomes a company, being a CEO is not about that spirit of rebellion on a day-to-day basis. Being a CEO is about leadership, which requires inspiring people with your crazy vision of the future, but also requires the hard day-to-day work of defining reality. The CEO of American Express paraphrased it best: “The role of a leader is to define reality and give hope.” As an entrepreneur, you’re good at creating hope, but becoming a business means you need to be good at defining reality.

The paradox is that most founders make bad CEOs. It’s a rare founder that can evolve. You have to self-lobotomize, eradicating some parts of your brain, constraining others, and making the company safe to your craziness. Some founders are really good at it and some are not.

Me? I’m a great Founder and a mediocre CEO.

Set boundaries for yourself

I was talking to a female Founder recently who had started and exited three companies. She founded one when she had little kids at home, another when she had older kids at home, and the last when there were no kids left at home. She said that the best experience she had was when she had little kids, because if she didn’t take care of them, they would literally die. There’s no question in your mind that you have to take care of them. She said the worst experience running a company was when there were no kids in the house, because there were no boundaries. There was no end to how much you work, and there was no perspective.

I see this in my own life. I don’t know how to draw the line between professional and personal. My sister is better at it than I am because she knows that she has to show up in her daughter’s life and her husband’s life and in our parents’ lives. It’s just part of her being. I’m an idiot because I work all the time. I have Bonobos, but I also have a seed stage investment firm called Red Swan. I’ve crammed so much professional action in to my life that I have to learn to have a personal life.

The future of Bonobos?

We’ve proven a couple of crazy things so far. First, we’ve shown that you can build a brand that’s digital at its core. This was revolutionary in 2005 and it will be old news in 2025. There’s now an avalanche of digitally-built brands. In the United States we were the first. So, we’ve done that.

Second, we’ve invented retail stores for our digital stores. We have thirteen as of January 2015.

The third thing we can prove is that we can replicate this. We’re not House of Cards; we’re Netflix. We are a studio for great digitally driven brandsthat’s what Maide By Bonobos is all about, and AYR, our women’s line. A lot of women say they will never buy clothes online without actually shopping and trying them onbut we’ve seen the opposite. All the women in my life are busier than me and I’m the CEO of a company with 280 employees. My mom, my sister, and my girlfriend are all busier than I am, and they tend to be more invested in the relationships in their lives. Women carry the world, which is why we named our brand after a female chimpanzee.

Andy Dunn is an IVY Thought Leader. To learn more about IVY, please visit