The Way I Work byTim O'Shaughnessy

"If you're not nervous about one or two decisions every day, you probably aren't trying hard enough."

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.

We started with 30 employees, in 2009, and now we have about 5,000. As we have grown, we have had to become systematic about hiring. We didn't have a true onboarding process three years ago. Now, new hires are flown to D.C. to get a full office tour and orientation, which includes a tutorial on Pulse, our internal tool that lets you look up e-mail addresses and pictures of fellow employees. We have a lot more of those types of tools than we did several years ago, which makes it a lot easier to deal with the scale of our growth.

Preserving our company's culture is incredibly important to me. When we started growing so fast, we realized we needed to be proactive. About two years ago, we got a group of people together who had been with the company for at least a year and asked, "What makes this place tick?" Then we formalized those values and painted them on the walls of our offices. "Make strong moves" is one of them. It's something we say all the time. I truly believe that if you're not nervous about one or two decisions every day, you probably aren't trying hard enough.

We have acquired 11 companies since we started, eight of them in 2011. That has kept me very busy. Basically, I'm interested in acquiring companies when it's easier to buy than to build. Before we make any moves, we rigorously examine each company, including the leadership team, the financials, and the company culture. I'm as interested in the office vibe as I am in its output. For instance, I really liked the vibe at Ticket Monster, a Korean company we acquired last year. Their offices looked like ours. If we swapped LivingSocial employees with Ticket Monster employees, no one would notice a difference. After each acquisition, we fly a few members of our HR and business development teams to the location to do on-site training on our company values, benefits, and history.

Now, more than half of our employees are outside the U.S., so I travel internationally often. I'm usually gone for one week a month. I also do a day trip or an overnight trip once a week, most often to New York City, San Francisco, or Seattle, where we have offices as well as partners and investors.

Since we have grown , I've tried various things to stay connected to employees. I used to do a weekly lunch with new hires. Then I tried flash cards to remember names. I even put an ice cream freezer in my office and invited everyone to stop by. But I've come to realize that it's impossible to spend quality time with every person at LivingSocial.

Instead, I look for ways to make sure that my view and values permeate the culture. One thing I try to do is spend time with each of my direct reports and each of their direct reports, even if it's only 15 minutes a month. That's 80 people. I can have meaningful conversations with 80 people. Not 5,000. I don't always hit everybody every month, but I strive to.

I'm also a big fan of shadowing. I go and sit with one of our consumer advocates once a month for 30 to 60 minutes and take calls from our members. Or I will sit with our merchant services group and take calls from merchants. I want to know what's going on, and it's a great way for me to hear directly from members and merchants. Plus, I get to interact with employees that I haven't met before.

Another way I try to stay connected is through a companywide meeting I hold once a month. It's a live webcast that is streamed to all the offices. My goal is to make sure everybody understands the key metrics of the business and to identify areas of great opportunity or great risk. For instance, if we're thinking about launching a product, like Instant Ordering, I'll introduce it and have the project manager do a presentation about it. Then we'll have a 15-minute Q&A with everyone.

We usually end the webcast with an Ignite presentation from one of our employees. It's basically a five-minute PowerPoint presentation with 20 slides. Any employee can submit one. Normally, the topic isn't company related, though someone recently did a funny one called "How to Be a Successful Intern at LivingSocial." Somebody else did one about growing up in a family of six girls. I love these, because it highlights the real people who work here.

I try to do the webcasts from a different office each month, depending on my travel schedule. I also try to do them at various times, since our offices are spread out. So one month, the meeting might be at 9 a.m. Eastern. And the next month, it might be at 5 p.m. Eastern.

I try to maintain an air of fun in the office. Each of our offices has a fun room—with Skee-Ball machines, an Xbox, or a shuffleboard table. In one of our D.C. offices, we have a ball pit that doubles as a conference room. These things are important because they add levity to the day, but it's more about the tone. I want people to know this is a culture where they have permission to be creative and take risks.

I also try to set the tone by not working on the weekends. Monday morning to Friday afternoon is LivingSocial time. The weekends are your time. It's really important for people to take breaks and unplug. So unless something's really urgent, I don't send any work-related e-mails until late Sunday night.

My Saturdays and Sundays are primarily for family time with my wife and son. We have a weekend place 90 minutes outside of D.C. that we go to with some regularity. Sometimes we'll go visit family in New York and the Midwest. My wife and I are pretty low key. One of our favorite things to do is open a bottle of wine after Peter goes to sleep and play gin rummy. We like to spend time and talk, and just be together and quiet.