The Way I Work: Tim O’Shaughnessy, LivingSocial

From the moment Tim O'Shaughnessy launched LivingSocial, in 2009, the Washington, D.C.-based daily-deal site has grown at breakneck speed. Fifty-four people bought its first deal, a $25 voucher for $50 worth of food at a local restaurant. Last year, the same offer attracted more than 6,000 customers.

LivingSocial has more than 46 million members in 25 countries and close to 5,000 employees worldwide, about 900 of them in its D.C. headquarters. Fueled by close to $1 billion in funding from VC firms and Amazon.com, LivingSocial has acquired nearly a dozen companies and launched offerings aimed at travelers and families. And the 30-year-old CEO continues to charge ahead. Every day, O'Shaughnessy scours company data, looking for growth opportunities. He also spends his time looking for new ways to connect with LivingSocial's ever-expanding work force. He told his story to Liz Welch.

I'm obsessed with numbers. I usually wake up around 5 a.m. Before I get out of bed, I grab my phone to check my e-mail and look at our numbers. We've got an internal tool that lets me see our aggregate revenue, number of items sold, and other figures. I track our revenue in 24-hour cycles, starting at 5 a.m. So I'll look at how the previous day's revenue ended up. If it's after 5, I'll look to see how that day's sales are going so far. If the morning pacing is off, I'll e-mail the CTO to see if there are any technical issues. He'll check and let me know if there's a problem. Or he'll write back, "Everything is pacing normally, Tim. You're crazy."

Then I usually go to the gym for an hour. When I get back, I play with my 1-year-old son, Peter, before he leaves for day care. The woman who runs the day care picks him up in the morning, which is superhelpful. It saves us 20 to 30 minutes in the morning. My wife and I trade off picking him up.

My wife, Laura, runs a Facebook marketing company called SocialCode. She works in New York City two days a week. I also travel a lot, so our life is a logistical nightmare. We make sure to spend every weekend together, as well as at least two nights during the week. We coordinate by sending each other Google Calendar requests. We'll send things like "your turn to pick up the dry cleaning" or "dinner with friends" or "Tim to Hong Kong."

I usually arrive at the office by 8:30. I like to ease myself into the day, so I don't schedule meetings before 9. That gives me time to grab three cups of coffee and go through e-mails at my desk. My rough rule is, if I can respond in less than 30 seconds, I write back immediately. If it will take longer, I will save it for my hourlong work session, which I take every day at various times to pound through everything in my inbox. If a response isn't urgent, I'll forward it to my assistant, Caitlin Levesque, who also manages my calendar.

I also spend time in the morning reading. I get Google Alerts about LivingSocial, our competitors, and other companies I find interesting. I also read Business Insider, TechCrunch, and Media ReDEFined, Jason Hirschhorn's newsletter. The more data you gather, the more likely you'll be successful in the long term.

Every Monday, I have a 10 a.m. meeting with the heads of every department. We go through key metrics and talk about longer-term projects, like Room Service, a new product that involves partnering with local restaurants to have a fine-dining experience delivered to your door. These meetings help catch me up on what's happening in the company and help me prioritize my week.

I also hold a biweekly meeting with our competitive-intelligence team, which is made up of about eight people. Their job is to research the competition—who else does what we are doing? Are they doing things differently? Better? Worse? It's important to know what the landscape looks like so we can fill in any gaps and improve our products.

I'm very involved in how the product works. For instance, we just launched a product in D.C. called Instant Ordering. We partnered with more than 70 restaurants and imported their menus into our system. Now members can order takeout and delivery through us. It was a concept I really believed in, so I sat in meetings three times a week for months with various teams to help figure out what to build, how it would work, and how we would promote it. So far, it has been really successful. We are planning to expand it to other metro areas. And I've been using it to order my lunch.

I'm constantly looking for patterns in the numbers. I get excited whenever I see a spike in sales, especially when it's for something new, like our Shootin' & Drinkin' package. Basically, we bus people to a shooting range and serve them whiskey afterward. I'll send an e-mail to the head of sales to find out how we approached the merchant and put the package together, so we can try to replicate it in other markets.

I carry a little leather Moleskine notebook with me everywhere. It's filled with lists, like numbers I want to discuss, agenda items for staff meetings, or the biggest threats to our business. If I have an idea, it goes in there. I often flip through my book at night. If there's a good idea, I will type it up and send an e-mail. I go through one notebook every month, sometimes more.

I meet biweekly with my chief of staff, Michelle Morris. She helps me figure out if we can build scalable business models around the ideas I'm interested in pursuing. We have an internal research team that does surveys and focus groups, and a team that pulls together all the pertinent financial variables. So we can figure out how successful a product, like Room Service, might be. If we can get x number of restaurants to sign up and drive y number of orders per day, and the average order size is going to be z, then we can figure out if it's a business worth pursuing.