Lyft, Harry’s, Drybar founders share best business partnership lessons

Before starting Harry’s with Andy Katz-Mayfield, Jeff Raider was a cofounder of eyeglasses brand Warby Parker, where he learned partnerships thrive when cofounders have clearly defined responsibilities and set aside their egos.

Harry’s cofounders and co-CEOs Jeff Raider and Andy Katz-Mayfield.Harry’s

Jeff Raider: So I mean, I think having cofounders and co-CEOs in a company is great if you feel like you’ve got a great relationship with that other person, and your skills complement each other well. You know, when you’re starting a company, early on, you’ve got so many things you’ve got to do. I mean, there’s all these different functional buckets, and then there’s 100 items under each of those that you have to think about, you know? Just to ship product, you have to find a distribution partner. You have to negotiate the right rates. You have to figure out the right protocols and processes. And so, there’s just way too much for any one person to do. You’ve got to build a team that can help. And if you want to be excellent at a lot of those things early on, having amazing people who can, I think, drive different pieces of that is really valuable. And I think, you know, it was helpful for us to be able to kind of divide and conquer in that way; trust each other, in an implicit way, that we were going to execute well on our individual pieces; and then obviously, align on the areas of intersection on sort of the general vision for the business.

Richard Feloni: So, how would the co-CEO model be different from, say, one of you being a CEO, and one being the COO?

Raider: Yeah. I think, you know, for us, we always felt like we were equal partners in this business. That’s how we structured the business, economically. That’s how we structured our sort of engagement with the team. It’s us, doing this together. And so, we felt like creating unnecessary hierarchy would just complicate that dynamic. And it’s always been that dynamic. You know, Andy and I kind of joke that we finish each other’s sentences. We now, we’ve known each other for 15 years. We’ve spent so much time together, and that, sometimes, our email should just be Jeff and Andy at Harrys.com, instead of Jeff at Harry’s, or Andy at Harry’s. You know, like your grandparents have an email, you know, whatever-

Feloni: Like a shared email, yeah.

Raider: Yeah. And so, you know, we feel like it is a partnership, and that our titles just reflect that partnership. We’re also not precious about titles. I’ve never been like, you know, “Oh, I’m,” this title or that tile.

Feloni: If you have equal footing, has there ever been moments where you’ve butt heads?

Raider: I mean, I think there are times when we disagree, but I think we have a tremendous amount of mutual respect for each other. And so, our disagreements are never personal. It’s always just sort of objective, like what is the right answer to this specific question. And then, we usually use logic and reasoning to sort of solve it. The other thing that we’ve done a lot is, if we have really hard problems that we’re not sure of, we talk a lot about the fact that there’s not always necessarily a right answer. And so, what we then, often times, do is just get amazing advisors around us, and present those questions as a unified front; together, say, “Listen, we’re thinking about this. We’re actually not sure. Here are the benefits. Here are the drawbacks. Can you just help us think through this?” And I think, oftentimes, their input is really valuable to our decision making process as well.

Feloni: So, it sounds like the way that you guys have figured it out is a matter of like, setting aside your egos, and just letting someone choose?

Raider: I think that’s right. And I think we respected each other’s perspectives and ability to sort of drive our parts of the business together. When it came to strategy, where are we taking the company, what do we want to build in the longterm, I think that’s where we spent more time together. And I think, you know, one of the things that we always talk about is that strategy is what you don’t do, as opposed to what you decide to do, because we have all these opportunities. And so for us, it was about thinking about, “Okay, what are the things that we really want to do, and the things that we’re not sure about,” and then getting input from our team, and board, and advisors, and other people at the right points in time, to help us where those answers may not be as clear.

Alli Webb started Drybar with her brother Michael Landau and her husband Cameron Webb, and the experience taught her it’s necessary to draw a line between personal and professional lives.

Drybar cofounders Michael Landau and Alli Webb.Drybar

Alli Webb: I think when you run and operate your own business, it’s really hard to draw that line between personal and business.  We’re always all talking about the business. It’s just the fabric of our lives, really. There’s definitely been fights and disagreements, but I think it goes back to that level of respect we have for each other, that we trust, and that there’s an innate trust that’s there. I think you don’t always have to be just with your family, and a partnership with your family to have that, but having somebody you really trust that feels like family is crucial.

Feloni: Is there a moment that you could point to, either in the early days, or even as it was scaling, where one of those were, it was maybe threatening a personal relationship, but you figured it out?

Webb: Yeah, I mean in the very early days I was kind of the conduit between Cameron and Michael I would be sending, this is very early days, I would send Michael something that Cameron had designed, and been like, “Hey, what do you think of this?” Then Michael would be like, “Well, I don’t really like blah, blah, blah, blah.” I’d say, “Well, Michael doesn’t like this.” And Cameron would be like “What the f—? Why doesn’t he like that? It’s so stupid.” And I would be like, “I don’t know, I’m just the in-between here.” It was a bad place to be. Finally, it sounds so simple in retrospect, but finally I was like, “You guys just talk to each other. I don’t want to be in the middle of this anymore.”

It forced them to stop using me as this go-between of this back and forth, because that’s never a good idea. For them to talk directly, there was a much greater level, they’re not technically related, so there was a little more respect, I guess, between them, versus just saying whatever they wanted to me, because I was the sister and the wife. So, that was a lesson we learned really early.

Then what happened, it was kind of magical, because Cameron’s such a great designer, and marketer, and my brother is such an amazing marketer. So, when the two of them would get together and talk about things, it would get even better. It was like a blessing to actually get them to talk to one another versus talking through me, which was not a good idea. Which we learned the hard way. I think that’s why the partnership works so well.

Feloni: Staying in different lanes.

Webb: Yeah. Having strengths, and knowing your strengths, and your weaknesses. What you’re good at, and what you’re not, I think, is incredibly important for any business, no matter what it is. I feel like just how Drybar is built on this premise of doing one thing and doing it really well. I think that I have a lot of different skill sets, but I think my main skill, and best, and highest use with this brand is making sure the hair looks and feels a certain way in the training of the hair, the customer service, how the shop’s run. That’s all my stuff. That’s the stuff I know and understand. Michael is dealing with finding leases, and negotiating terms and all the sh– I hate. And Cameron, I didn’t really understand branding until we started building Drybar, and Cameron was so adamant about everything being yellow. I always tell the story our first Valentine’s Day, the shop was open, I wanted to bring in pink flowers, because it’s Valentine’s Day. Valentine’s Day, it’s pink and red. He was like, “No the flowers have to be yellow.”

Feloni: Go against branding.

Webb: Yeah. Everything has to be yellow, and gray and white. I slowly, but surely, learned that from him. And I learned so much from my brother about figuring out spaces, and learning how to raise money, and all those things. So, we’ve all taught each other so much about each other’s areas, but there is still that level of respect of like, “This is what you do. This is what I do.” So, we divide and conquer.

GOAT cofounders Eddy Lu and Daishin Sugano have a brotherly dynamic — which led to some serious fights — and they learned how to work through disagreements.

GOAT cofounders Eddy Lu and Daishin Sugano.GOAT

Eddy Lu: Every night after work we would just talk about what we could build on the side, what we could do, how to create a new business. It wasn’t a startup back then, it was just, “Let’s create a new business while we’re young.”

Feloni: Why? What do you think drove you to say that?

Lu: I don’t know, besides the fact that we always wanted more, for some reason. Daishin and I quit cold turkey on the same day in 2007. We were just like, “Let’s just quit and figure it out.” Much to the chagrin of our parents. My dad was very happy I had a Lehman Brothers job. But we just didn’t feel like it was right. We wanted to try something while we were young, so we just quit and started to do stuff.

Feloni: Do you think that you and Daishin would have quit your jobs cold turkey had you guys not had these conversations? Would you have done it on your own if he had not been in your life?

Lu: I think having a cofounder you can trust is so important. You hear all the time, it’s really hard to start a startup by yourself. I’ve seen it through the years, and believe me, Daishin and I have worked through our issues. We’re an old, married couple now, but in the beginning, we’ve had physical fights, we’ve thrown each other to the ground, there was this one time at a restaurant, I remember. We had a disagreement about some business term, and we were yelling at each other at the restaurant, people were looking at us. He got up and walked away, and I kept on barking at him, walking out the door. We totally forgot to pay. We just walked out the door all mad at each other. But we knew that, just right after that, we were just like, “Okay, let’s just focus again. Let’s just get to it.” And that’s what’s really built the company. Resilience is another one of our core values, and it’s because we were able to bounce back so quickly from setbacks. Thankfully, since we’ve been together, and worked through all those issues for so long, now that we’re doing GOAT it’s just so much easier. We know our lanes, we know what each other’s good at, and we just can execute.

Before he started running events for Drake and Mary J. Blige, Larry Morrow said he learned from an experience with an early client that you’re better off working alone if your partner doesn’t share your vision.

New Orleans entrepreneur Larry Morrow.Hollis Johnson/Business Insider

Larry Morrow: So, when [actress and model] Draya Michele came down, [she and her friends] wanted to get their hair and nails done. We go to the salon. I had a friend of mine, I’m like, “Yo, look. Let’s go half on their hair and nails.” And, he didn’t really want to. So, I paid for it. They went to dinner and I go, “Let’s go half.” He didn’t want to. I paid for it.

I’m 20 years old, and he was five, six years older than me at the time. And, pretty much, long story short, at the end of the day they told me, they were like, “You know what? Out of all the cities we’ve been to, you took care of us the most. And, you’ve been the youngest.” They were impressed by it.

Feloni: And, did that business partner that you started off with, did that not work out because you weren’t seeing eye-to-eye?

Morrow: Yeah. We had two different visions. When you align yourself with somebody, you’ve got to believe in the same things. Y’all have to share some of the same vision, and we didn’t. So, we worked together for about three years, and I’m thankful for that situation because it taught me so much.

And he’s a good dude, but we just had two different visions. I think it was best that we parted ways. And, let me tell you, when we did, it was on. It was on. Because when you do have a business partner, you’ve got to understand that it’s not all about what you want. It’s also about what they want. Not saying it’s not good to have a business partner, because you may go further together than you can on your own, but I took off.