When You Hate Being A CEO…


Blake Mycoskie, founder of TOMS shares what he's learnt.

Image courtesy of TOMS

From hiring a new CEO to selling 50 per cent of his company to Bain Capital, Chief Shoe Giver Blake Mycoskie talks why he hated going to work – and what he did about it.

When I started TOMS I had no experience at all. No developmental experience, no public health experience.

Poverty alleviation is complex and it requires what I would call a very unique cocktail and a little bit of luck. The cocktail has everything from basic aid – clean water, shelter, shoes on your feet and food in your belly – to making sure the right centre program exists for girls to go to school, to finding ways to break the unemployment by creating jobs for people. It really is a very complex thing that I think sometimes gets over-simplified. What I’ve learned is everyone has to do the part that they can do best and no one can do everything.

I’m an entrepreneur and I like to make fast decisions with small groups of people who are all passionate and connected to the same mission. And over time, as the company got bigger and I think we started to bring in some executives that maybe weren’t the best cultural fit, that weren’t aligned to the overall mission, I found that it started getting quite bureaucratic and not as much fun.

So I took some time off and kind of re-evaluated where we were as a company and what I felt we needed to do to go to the next level. We made a lot of changes, and it’s been about a two-and-a-half-year process of trying to get us back on track.

I think attitude is the most important thing and also just ease to work with. I think we hired some people we knew were going to be challenging but they had the right résumé and the right experience, and I think as an entrepreneur you get insecure about the things you don’t know and you stop trusting your gut as much. So now I think we’re much more focused on attitude and ease to work with. They need certain basic experiences, but it’s much more important that they’re going to be someone who’s going to be a real team player, fun to work with, easy to work with, and with a very positive attitude towards the challenges we – every business – has.

I think I did what a lot of entrepreneurs do [on sabbatical]; I made the classic mistake, I swung the pendulum way the other way, I fully disengaged. I played way too much golf, probably drank too much, just went to the retired life. It didn’t take long before I wasn’t enjoying the golf, I probably wasn’t that easy to live with and I realised that I really enjoy working and I enjoy creating and growing TOMS, I just didn’t enjoy the current situation that the company was in and some of the people I was having to work with every day.

It wasn’t that I was burnt out on TOMS’ mission, I was just burnt out on the way we were operating. That was a great learning. It was also great learning that while I do love hobbies and recreation, if that becomes your main focus it loses its lustre really quickly. We need a good balance in life; in order for you to enjoy a vacation you need to feel like you’ve earned it. Even if you have all the money in the world it doesn’t matter. If you don’t feel a sense of hard work and purpose in life, it’s hard to enjoy your time away because your time
away almost becomes a job itself.

The biggest changes really were people. We changed a lot of our executive team.
I also brought on a financial partner to help me really make the big decisions and also help us think about the long-term growth and capital structure. And then also really putting our focus back to footwear instead of lots of new products all the time.

I think the most important thing [in choosing an investor] is that you’re really aligned from a values standpoint and also from, ‘What is the role of the entrepreneur post-transaction?’ I was fortunate that I found a partner who saw my best uses exactly the way I did. And so they saw that I’d only be at the office about 30 per cent of the time; I’d really focus my time – when I am there – on the marketing and design and getting innovation; that I would not run the business; that I wouldn’t have any direct reports. Things that I felt got in the way of my growth, we agreed on.

I never felt comfortable or excited in that [CEO] role. I’m very excited about being a founder and talking about positions and where we’re going and what we can accomplish but actually having to have eight or nine direct reports, dealing with as much of the finance and HR areas that I would have to deal with as the CEO, it’s just not what I really signed up for or what I hoped to be spending my life doing. Some people are really good at that and really love that stuff and… it feels like a noose around my neck. For me it was a little bit in-between – I like some aspects of it, I like the leadership and the mentoring and some of that stuff, but I really did not like the day-to-day multiple decisions, time restraints. I had to take time making decisions and that role required a lot faster decisions.

It’s all about role clarity. Really understanding who’s running the company day-to-day, what are the responsibilities. Also it’s just about personality set. I don’t think there’s a science to it, it’s probably like a marriage – sometimes opposites attract, sometimes opposites repel each other – it’s about finding the right mix. I was able to find a CEO that I have really good chemistry with, we have very clear role definition, we have a lot of respect for each other’s strengths and I think we also have a good awareness for each other’s weaknesses. When it goes wrong I think that’s when you don’t have the role clarity and there’s not that mutual respect and connection.

Image courtesy of TOMS

Thankfully right now we haven’t had any major disagreements. Unless it’s something that I feel so passionate about, that I feel can hurt the business, I’m going to let him go with the path that he’s on. Because ultimately, as CEO, he’s the one who’s ultimately responsible for his decisions. So if I go to hire for instance, and we were to interview someone, and I like one candidate slightly better than the other candidate but he likes the other candidate, then I’m going to say, “Go with the candidate you like.” Now, if I thought he was going to hire a disaster waiting to happen, well then I would be able – and that’s what having the financial partner [means] – I’d be able to just say, “Hey, let’s take this conversation to the board and let the board help us make a decision because I think you and I are too far apart”. So that’s how that works.

You’re going to make mistakes and it’s okay to make them as long as, as soon as you realise, you deal with it – you rip the band-aid off, you have the hard conversation, you make the moves from a product standpoint or personnel standpoint. Denial is the worst thing that can happen for an entrepreneur. So I think I’ve become more decisive when I know that I’ve made a wrong decision, or a product’s not working or a retail relationship’s not positive, like, ‘Let’s make changes and move on’. Whereas before I’d probably operate a little bit out of fear and fear’s never a good way to operate as an entrepreneur.

Frankly, I miss living on a boat a lot. My life was so much simpler, I had no room for stuff so I had very little material possessions, and it was a very romantic way to live. To come home, have a couple of beers and eat some take out sitting on the boat watching the sunset, it was a very awesome, liberating feeling. In some ways I think it made my evolution into being married and now being a dad much harder, because I think I lived – unlike some of my peers – a life of really, really radical freedom from a lot of things that hold people back. And then when you get married, you get a house and you get all this stuff and it’s hard. And I think it’s even harder for me to adjust to marriage, to being a dad and having all these other responsibilities and stuff than had I not lived on the boat. But I’m still glad that I did it.

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