A Day In The Life Of A Multi-Billion-Dollar Startup Founder

tim o'shaughnessy livingsocial founder

Photo: Fortune Live Media via Flickr

Inc’s Liz Welch interviewed LivingSocial founder Tim O’Shaughnessy.LivingSocial is a daily deals company with a multi-billion-dollar valuation, more than 46 million members and 5,000 employees. It was founded in 2009.

O’Shaughnessy says he wakes up at 5 AM and grabs his phone while he’s still in bed to check email. He also checks company numbers, such as aggregate revenue and the number of items sold every morning.

He frequently fires off emails to his CTO to make sure everything is running smoothly.

Then it’s off to the gym for an hour followed by personal time with his one-year-old son, Peter.

O’Shaughnessy does all of that before 8:30, when he arrives at the office.  He doesn’t take meetings before 9:00 so he can grab coffee and sort through emails.

If he can respond in under 30 seconds, he will. Otherwise emails get stashed for later. Then he reads Business Insider, TechCrunch, and a few other news sites.

Monday mornings are when O’Shaughnessy meets with the heads of LivingSocial’s departments. He holds bi-weekly meetings with a “competitive-intelligence team.” He also meets with his Chief of Staff bi-weekly. O’Shaughnessy is also kept busy acquiring companies — LivingSocial acquired eight last year alone.

The founder says he’s obsessed with numbers and tries to find patterns in them.  If sales spike, he wants to know why.

He totes around a Moleskin notebook to jot down reminders and talking points. It’s his idea book and he often flips through it before bed. 

O’Shaughnessy is very interested in LivingSocial’s products and in keeping company culture.  He’ll often sit with the customer service team and answer phone calls.  Also, every LivingSocial office has a Fun Room with Shuffleboard, Skee-Ball and XBox consoles.

He believes people should “make strong moves” and says everyone should be nervous about at least one or two decisions every day.

Company-wide meetings are held monthly at LivingSocial. O’Shaughnessy hosts the web casts in different LivingSocial offices every month depending on his travel schedule.  Meetings are wrapped up with a non company related PowerPoint. PowerPoints are made be LivingSocial employees who share interesting things about themselves.

On weekends, O’Shaughnessy tries not to work. He believes it’s important to unplug and he spends Saturday and Sunday with his family.

His wife travels a lot for work too, but they spend every weekend together. Sometimes they’ll go to a vacation home just outside DC, but usually O’Shaughnessy and his wife enjoy a bottle of wine and gin rummy after Peter falls asleep.

To read more about O’Shaughnessy’s life, head over to Inc.

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