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How to Boss It Like… Gary Stewart, Director of Wayra

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Smart people get an incredible amount done, in an impossibly short space of time. But how do they do it? In our Boss it Like series we find out what’s behind some of the brightest leaders in business.

Today we meet Gary Stewart, Director of Wayra UK, the no.1 startup business accelerator in London.

Stewart has an eclectic CV. After graduating from Yale Law school he started his professional career in Washington and then moved to London, working at some of the City’s most prestigious law firms. A move to Spain took him on a new path to entrepreneurship, launching a successful online property search engine.

Then Stewart joined the world-leading IE Business School, where he became an Associate Professor and Entrepreneur-in-Residence.

Today he continues to give back to the entrepreneur community at Wayra’s academy in London.

A busy man, with big ideas, The Memo asked Gary Stewart how he gets it all done…

How do you start your day?

Depending on whether my insomnia kicked in the previous night, I tend to get up at about 6am.

I read The New York Times, The Wall Street Journal and The Guardian before going to the gym for a spinning or high-intensity interval class. I obsessively check my Facebook and Twitter feeds, which I probably need to control at some point.

What apps do you use?

I’m kind of old school in this regard. I’m a neurotic New Yorker, so my main challenge is not being productive.

For me, the issue has always been learning to enjoy life and not take anything too seriously.

To counter my perfectionist impulses and get myself in the right state of mind at the beginning of each day, in addition to going to the gym, I listen to the same Spotify playlist. The songs are all either gospel or sappy pop songs that help me to come to work feeling good about life and keeping things in perspective.

The most important thing is to remember how lucky I am, how short life is and that my focus really should be on trying to be happy. That is, after all, why I left the US to come to Europe.

What smartphone do you have?

I have a black iPhone 6 with 64GB of memory.

I prefer the gold one, but the IT guy at Telefónica said he only had the black one in stock when I replaced my last one after my phone fell and the screen cracked.

How many people do you meet in a day?

I probably meet actively with 20-40 people most days.

We have 80-100 entrepreneurs in our Academy on any given day, in addition to the internal Wayra team and our investors in residence.

We also have a lot of current and future partners, as well as startups that are interested in joining Wayra.

Most of my days are spent meeting various permutations of these different groups.

What books are you reading?

I am not currently reading any book right now, given that when I’m not at work, I’m mostly obsessed with reading (and watching) everything about the Brexit referendum and the US presidential election.

Now is not the time to escape and suspend disbelief; the current political reality already seems like a bit of science fiction.

When do you work until? Are you still sending emails in the night? Or do you have a wind down routine?

I used to live next to the Wayra Academy, reasoning that it was more “convenient”.

What it meant was that I never disconnected and would work and send emails all day and all night. I was soon made to realise, however, that it was a recipe for destroying my personal relationships and just generally a way to age more quickly, because I was always being tired and stressed out.

I’d lived in London for a year but hadn’t found the time to really enjoy it. Now that I’ve moved, I make an effort to disconnect once I get home and devote that time exclusively to family and friends.

As soon as I get on the tube, I put my gospel music and sappy pop songs on, and once I reach my house, I know that work is over. I can interrupt my personal time in the case of real emergencies, but they should be an exception and not the rule.

What piece of advice would you give to anyone starting a career now?

Don’t worry if you don’t know what you’re doing. You’ll probably feel like an imposter all the time, and it doesn’t matter that you have no clue where it’s all going to end up. That’s life. Be entrepreneurial about it.

When I graduated from Yale, I had a 5-year plan to conquer the world. But then life intervened. I ended up switching both careers and countries 3 or 4 times, and none of it was ever planned.

It was always about looking for new opportunities and challenges that I felt passionate about, and then trying to believe in myself and remain optimistic, even if my friends and family told me that I was crazy.

And I think it worked out OK for me.

Why should people care about the Brexit vote?

For me, it’s simple. I left Spain for London, because London is the most dynamic and diverse city outside of my hometown of New York. The quality of life is awesome in Spain, but, in London, it feels that anything is possible, no matter where you come from.

And what’s crazy to me is that all of this is being put at risk without a coherent argument or plan to replace it.

People are replacing logic and facts with false hopes, delusional optimism and a bit of populist xenophobia. The NY Times, The Wall Street Journal, The Financial Times and The Economist have warned of the dangers of Brexit, as has NATO and most of the world’s leaders.

They worry that it’d do significant harm not just to the UK but to the global economy, and anyone following the stock and currency markets over the last few months knows that the investors are also worried. Yet the only argument that the pro-Brexit side has is that worrying about your job and home is “Project Fear”, and when asked for a plan, they say that a plan is not necessary and experts should not be trusted.

If any entrepreneur ever came to me with such a pitch, I’d tell her that she was delusional and then secretly wonder what she was smoking.

Taking a monumental risk without knowing your facts or having a compelling plan is suicidal.

Given what’s at stake, I can’t believe that anyone is even taking them seriously.


Come back next Thursday for our next #BossItLike interview, and get in touch if you know a business leader who’s also a productivity guru for us to talk to.

The post How to Boss It Like… Gary Stewart, Director of Wayra appeared first on The Memo.


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