Are you Still the Best Person?


There’s no better story of the new, disruptive economy than Uber. What could be more set in stone than your local taxi company? But along comes Uber, along comes an iPhone app and everything is different.

Equally there could be no more archetypal disruptive entrepreneur than Uber co-founder Travis Kalanick.

Travis Cordell Kalanick is 40. He dropped out of UCLA (obviously: dropping out is mandatory for the disruptive entrepreneur).

His first business venture – with partners – was a multimedia search engine and file sharing company called Scour, which ultimately filed for bankruptcy.

Next came Red Swoosh, another peer-to-peer file sharing company. Red Swoosh struggled: Kalanick went three years without a salary, had to move back into his parents’ home and at one point owed the IRS $110,000. All the company’s engineers left and our hero was forced to move to Thailand as a cost saving measure. But in 2007 Akamai Technologies bought the company for $19m.

In 2009 Kalanick joined forces with Garrett Camp, co-founder of Stumble Upon, to develop a ride sharing app called Uber. And the rest as they say…

Uber now operates in 66 countries and more than 500 cities around the world. Wiki lists Kalanick’s net worth at $6.3bn. Presumably he’s not living at home any more.

But neither is Kalanick still at Uber. On June 20th he resigned as CEO after multiple shareholders demanded his resignation. We’ve all read the stories: let’s just file them under ‘abrasive personality.’

Looking at Kalanick’s early struggles he ticks every box for an entrepreneur. Dropped out of college, saw the future, first venture failed, money problems, do whatever it takes, absolute persistence, never lost faith in himself and – eventually – jackpot!

We can all imagine some of the scenes: we may not have ticked all the same boxes in our own entrepreneurial careers, but we’ve ticked enough to imagine Kalanick’s journey. And to empathise with it…

But now he’s gone. And his departure from Uber prompts an interesting question.

Are you still the best person to run your company?

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When I pushed my breakfast round my plate in Newport Pagnell services and decided to work for myself there were two main motivations. They were frustration: “There has to be something better than this,” and family: “Someone else is dictating how much time I spend with my wife and children.”

In some ways I was luckier than most embryonic entrepreneurs: my experience told me I could manage and motivate a team. But I wasn’t thinking about that in Newport Pagnell: what – after proposing to my wife – has turned out to be the best decision of my life was motivated purely by frustration at what I was then going through, and a determination to be there as my boys were growing up.

I suspect the vast, overwhelming majority of entrepreneurs are the same. We all started by saying, ‘I want to create something, I want to be in control of my own life, I want to build a future for my family.’ We didn’t say, ‘Oh yes, I have the skills necessary to lead a team of 30.’ Famously, even Mark Zuckerberg had to learn how to manage Facebook.

So the skills you had then – vision, a willingness to take risks (with both your career and your family), persistence and that sheer, bloody-minded determination to succeed – may not be the skills you need now. In fact, there’s no ‘may’ about it. Maverick entrepreneurs don’t always make great managers: you may have been the only person who could have started your business, but are you the best person to keep it going? Is it time for the visionary to make way for the general manager?

I’m not going to answer the question: I’m simply going to state that it is one of the most interesting and fundamental questions we’ll all face as our businesses grow, and one we’ll all need to ask ourselves. As I talk to the other TAB franchisees and to more and more business owners who are nearing the end of their entrepreneurial careers, it’s a question which increasingly fascinates me. We can never stand still: we’re always growing, developing and learning. Whether it is internal change or external change, the challenges we face this year are never the same as the challenges we faced last year.

That’s why you need friends. Whether it is your colleagues round a TAB boardroom table, your other franchisees or my team here at head office, they’ll always be there with advice, insight – and the occasional reminder that we shouldn’t take ourselves too seriously…

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One comment

  1. simonjhudson · 24 Days Ago

    Reflecting on this week’s blog, I am reminded of the observation that your Inbox is a To Do list that someone else is in charge of; it strikes me that this is a valid metaphor where Inbox = working for someone and To Do list = Life.
    The trick is to make sure, as an entrepreneur, that you don’t simply swap The Boss for The Business. Always that means keeping business and personal life balanced; sometimes that means stepping aside.

    Anyone want to run a successful IT company while I go boating?

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