How I work – CEO of living social.com

“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.