Tuesday, October 16 is National Boss’s Day, a custom that leaders should ignore, if not outright discourage. Expecting employees to celebrate the wonder that is you with a supermarket cake or Hallmark moment suggests that what you do–develop, guide, and inspire people–is insufficient reward on its own. Remember who should be grateful to whom in this relationship.
That said, great leadership and management do deserve recognition. Many entrepreneurs borrow practices or philosophies from their former managers, some of who become lifelong mentors. In honor of the day we asked successful founders about the bosses who influenced them and helped make them–and their companies–what they are. Here are their edited responses.
1. Paul English, co-founder of Lola and Kayak
In 1999 I sold an e-commerce company to Intuit and went to work for Scott Cook [Intuit’s co-founder]. I loved meetings with him, the way he always came prepared. I had breakfast with him a month ago–even now we get together when he’s in town. He carried a little notebook in his shirt pocket, and a pen and he took notes during our breakfast. He is always hunting new ideas and taking notes and trying to improve himself and the people around him.
In meetings Scott always asked the “dumb” questions, the ones on people’s minds that they are too shy to ask. Why we are even working on this? Do any of our customers care? I remember once we were talking about opening up QuickBooks’s API so that people could develop apps, and we were making up what kind of apps we thought people would build. Scott sat there with his arms folded, looking at the floor. You could imagine steam coming out of his ears as we were pontificating. And at one point he said, “There’s a phone on the table. Why doesn’t someone just call a customer and ask them what they think?”
He also trained people at Intuit to look for coachable moments. If you see an interaction that is suboptimal, he said, use it as an opportunity to make the person stronger. Say you see something kind of funky in a meeting. Call people on it. Not in front of the whole room. But after the meeting, say, “Hey, let’s talk about this thing and see what happened.”
Sometimes I would wonder if Scott is intimidating to people because he is so quick. But he is actually a nice guy. I wish there were more profiles of people like that, who can be as bright as other genius entrepreneurs but are also wired to be a kind person.
2. Alli Webb, co-founder of Drybar
My parents were my first bosses. They were entrepreneurs who owned their own clothing store. Our parents made my brother [Drybar co-founder Michael Landau] and I sweep the floors and other stuff we didn’t want to do. At my first job, at an Express store in the mall, I worked a lot harder than anybody else because our parents taught us to treat every job like it is your own business.
While I was in beauty school I worked as assistant to a salon owner named John Peters. Today his business is in Delray Beach, Florida, but back then it was in Boca. John molded me into the hairdresser I am and taught me to run a salon. But more important, he taught me the importance of humor.
Any time the stylists had a problem or question they always came to him, and I was a fly on the wall for those conversations. I also watched him with customers, who were mostly older people. He was always humble about his mistakes, but he would also throw things back at people with a little bit of good-natured sarcasm. A client might say, “John, my hair was not as good as last time,” and he would say, “What? No way! Are you crazy?” He made the whole exchange lighthearted. He taught us not to take ourselves too seriously.
I don’t think I’m a funny person by nature. But I learned from John how banter can turn even stressful situations into something fun.
3. Eric Ryan, co-founder of Olly and Method
In the mid-’90s I was a junior planner at Fallon, which was the hot advertising agency at that time. My boss was Rob White, who ultimately fired me. I was very disruptive, always trying to rewrite the rules, and Rob recognized I should be an entrepreneur. When he fired me he said, “I’m pretty sure I could be working for you someday.”
If Rob hadn’t fired me I would never have moved to San Francisco and might have delayed starting something on my own. I’ve told that story to pretty much everyone I’ve let go. Firing people is the hardest thing you have to do as a leader. But I believe it frees them up to find out what they are really great at.
Rob was big into the idea that culture is the glue that holds things together when you’re growing fast. You can see the fingerprints of that all over the companies I’ve started.
He liked to call Fallon “the Harvard of planning” and wanted it to be the hardest place to get into. After I did all these interviews for the job, he gave me several marketing case studies and told me to write essays about my opinions of them. I did it over the Fourth of July weekend, and I hated it. But it was brilliant because it showed him what I knew and how I thought. The homework assignment we assign to applicants at Method and now Olly was inspired by that. If you make someone work hard for a job, then they want it even more.
4. Seth Goldman, co-founder of Honest Tea and executive chairman of Beyond Meat
In 1988 Lloyd Bentsen ran simultaneously for vice president and senator from Texas. I worked on both campaigns and became his deputy press secretary in the Senate. I worked on Capitol Hill and with the Senate Finance Committee. And I went along on his swings through the towns and small cities of Texas.
Lloyd worked on tax, trade, and health care policy. Much of what he did was very technical. But when he talked to constituents he would make these sophisticated, complex ideas relatable. I remember one time he was going to talk to union workers about his effort to extend unemployment benefits. The speechwriter had come at it from a wonky perspective. Lloyd marked the speech up so much that in the end it was just his remarks. Instead of talking about tightening credit, he quoted Harry Truman: “It’s a recession when your neighbor loses his job. It’s a depression when you lose yours.”
At Honest Tea and Beyond Meat the work can also get pretty technical, dealing with fair-trade sourcing or offsetting greenhouse gases. I learned from Lloyd that when it comes time to communicate to the consumer, we have to make it simple, clean, and easy to understand.
Also, I met my wife at an event in Longview, Texas while working on Lloyd’s campaign. So I feel personally grateful for the role he played in my life.
5. Todd Carmichael, co-founder and CEO of La Colombe
Starting at age 14, I worked on a fruit farm outside of Spokane, Washington. My immediate boss was a guy named Mike McGlade. We were both distance runners: running 100 miles a week in the dark. And then just as the sun came up I would be facing a row of strawberries half a mile long. I had to hoe all the weeds around it, all day long in 100-degree heat with no Walkman, no conversation, no relief. Then I’d get up in the dark the next day and start over. Fruit needs care, and it is a brutal kind of care. People would crack. People would leave.
Mike happened to be the son of the guy who owned the farm. He did not need to do much work. He was the boss. But there in the row next to me–maybe 50 yards ahead–was this guy. He worked his brains out with a smile on his face. He showed me that the way up is the hard way.
In 1994 when I was starting a company I applied that same approach. We would work 16 or 17 hours a day. I would sleep next to the green coffee bags. And we would grind it out. Mike taught me about endurance–how to keep going hour after hour and day after day. In my life and in my business I set out to be the last man standing. I got that from him.
6. Alon Cohen, founder and president of Houzz
My first job was in the army in Israel. Even though I was only 23 my boss, Ofer Dayan, trusted me. After just a few months there I proposed some pretty profound changes to a technology system that would have a large impact on his team and other teams that he supported. He asked me some questions, and then basically said, “Let’s do it.” He gave a kid his full backing, guiding me when necessary but for the most part letting me go on my own. From him I learned it does not matter if someone is super-junior or super-senior, they can have a great plan. And it’s best to let whoever had the idea execute because they are the one with the passion. So at Houzz I let folks on the team do what I was empowered to do when I was young.
Later, Scott Leahy was my first manager at eBay, where I started as a senior manager of engineering. In addition to the basics of how to behave in a U.S. work environment, he taught me what it means to keep a production system up and running 24/7. That included jumping on phone calls in the middle of the night and on weekends. It included going deep into data and dashboards to understand where there are issues. It included improving the system all the time and making sure it is resilient and reliable. From Scott I learned there is a huge difference between 90 percent and 100 percent.
At Houzz I personally review every interface change on the platform, even though we may have reviewed it in meetings. Sometimes people make fun of me because I find something that is one pixel to the right or to the left of what it should be. But it comes of caring that the consumer experience is great.
7. Peter Buchanan-Smith, founder of Best Made Co.
From 2005 to 2010 I was consulting design director for Isaac Mizrahi, working on his packaging, branding–everything except apparel. We also did a book and a magazine together. He was in the tail end of his partnership with Target at the time. The very first project I did with him was packaging for a box of doggy poop bags.
I have never worked for anyone as inspiring as Isaac. He is the definition of a polymath: designer, performer, TV show host, cabaret singer. He is like a creative superhero. Nothing scares him. And he is always the same: in front of the camera, behind the camera, in an office, in front of an audience. He is always himself.
His schedule on any given day would make my head spin. He had his TV show, and the studio was built inside his creative studio, so he could take a break and run behind the scenes to oversee a pattern being made or the layout for a look book. He applied his energy in so many places at once.
If you look at our product assortment, there is a part of Isaac in there. It is eclectic and knows no bounds, which is something I learned from him. He was also design-driven, not trend-driven. And he had a real reverence for the past but was not nostalgic–always looking ahead. What I really loved about him was he was insatiably curious. That spirit of curiosity is alive and well at Best Made.
8. Tina Sharkey, co-founder and CEO of Brandless
In the mid-’90s I was head of programming for Q2, a new shopping channel being launched by QVC. I worked for Barry Diller, who was CEO of QVC at that time. He was incredibly focused, demanding, and strong. Truly an entertainment visionary.
We built this network from scratch, and we had set a date to launch it. It was not just TV; it was very complicated. The selling and the ordering and the computer systems had to be integrated. And it was live. I called Barry and said, “I don’t think we are ready. I think we’re going to delay.” Barry is very succinct. He said, “Anything worth doing is worth doing badly.”
I didn’t get it at first. But his point was that you are never going to know what you have and where you are unless you do it. For all the conference room meetings that we had and all the rehearsals and all the planning and all the opinions – we were basically talking to ourselves. When we went live, all of a sudden we were talking to the country. And they told us what they thought.
At Brandless, I say “Look, every day we are trying something new. And every day we don’t know what we have until we see it perform.” I repeat to my team, “Anything worth doing is worth doing badly.” It’s one of the best pieces of advice I ever got.
9. Scott Harrison, founder of Charity: Water
I’ve only had one boss of note, and I paid to work for him. In 2004 I had been a selfish, hedonistic nightclub promoter for 10 years, and I asked myself what the opposite of my degenerate life would look like. I wanted to explore service to others, so I signed on to Mercy Ships, which sailed hospital ships along the African coast bringing doctors and surgeons to people without medical care. I paid $500 a month to volunteer.
My boss was Gordon Tyler, who was head of communications on the ship. Mercy Ships was a top-down structured environment, but Gordon tailored his management style to what he saw in me. I had signed on as ship photographer and my job was to take photos of patients pre-and post-op. But that wasn’t enough responsibility for me. I wanted my title changed to “photojournalist” so I could also write stories, and he let me.
Then he gave me unbelievable latitude to set my own hours and pursue assignments off-ship. He let me take days off to go sleep in the bush or stay at a leprosy colony to understand the disease. It was on those assignments that I discovered the importance of water. Gordon said this guy will die if he is not given freedom. As a result he got 90-hour weeks out of me. Now, at Charity: Water, I’m a big believer in giving people a lot of rope.