How Tim Armstrong, a hotshot Boston sales guy, wowed Google's founders, built its multi-billion-dollar ad business from scratch, then became AOL's CEO
Before joining AOL, Armstrong was an executive at Google who helped build its advertising business from $700,000 a year to billions every quarter. He was also an expert advertising salesman and entrepreneur, and the first person to sell a $1 million digital-advertising deal, back when all the money was flowing to print and TV companies.
Armstrong visited Business Insider and spoke with Business Insider's US editor in chief, Alyson Shontell, for "Success! How I Did It."
In the interview, Armstrong discussed how he built a high-powered career. During the wide-ranging conversation, he talked about:
- How he started a newspaper out of college, where actor Casey Affleck worked for him.
- How he became a great digital-ad salesman and sold the first $1 million ad deal online.
- What it's like to be interviewed by Google founders Larry Page and Sergey Brin.
- How he helped Google pivot from a licensing business to an advertising business, and launch products like AdSense, which would eventually generate billions in revenue.
- How you know it's time to leave a safe, cushy job (Google) for one that's high-risk (AOL).
- The advice his dad gave him the night before he started at AOL.
- How he spent his first 100 days as CEO.
- How he makes gnarly decisions and comes to peace with them.
- How he inspires his teams when morale is low.
- How talks with Verizon CEO Lowell McAdam heated up and led to AOL's $4.4 billion acquisition.
- How you can be an effective leader who is also well liked and respected.
- The advice Tim gives to his children, and to anyone who wants to build a high-power career.
Here's the full interview, which you can listen to below.
Or, if you'd rather read it, here's a transcript, which has been edited for clarity and length.
A strawberry farm, volunteering to be fired, and employing Casey Affleck
Tim Armstrong: Alyson, good to see you. Thanks for having me on a rainy New York day.
Shontell: I want to go all the way back, to the beginning of your career. It sounds as if you were always entrepreneurial. I remember the story about your making a strawberry farm successful during college?
Armstrong: When I was growing up, I always had the entrepreneurial bug. There were multiple things I did when I was younger, in my middle-school and high-school ages. But one of them was with a friend from college. There was a strawberry farm that the bank owned. I don't know if the farmer had lost it to the bank, but there was a strawberry farm, and we went to the bank and they weren't using the farm, so we said, "Could we take over the farm for the summer and do a pick-your-own strawberries? It'd be a lot less work for us, and probably a lot more profitable."
And so we did a you-pick strawberry farm, from a farm we didn't own, and cut a deal with the bank to do it. We had hundreds of customers drive up and go pick their own strawberries, and it ended up being a very successful venture and a lot of fun.
Shontell: So then you graduate and you have a short stint in finance?
Armstrong: Right when I graduated from college, I actually taught a program called the Explorer Program at Wellesley College. That was for the summer. Then I went to an investment bank in Boston, and I was there for about three or four months, and I realized that banking was not something for me. So I went to my boss and said, "You know, I think you should let me go."
Shontell: You volunteered to be fired?
Armstrong: Yeah, I just said, "I don't think this is the career for me, and I should do something else." And they said, "No, why don't you stay? It seems like you could do a good job here over time." And I said, "I want to go do something else." So I left and ended up starting a newspaper in Boston, out of that experience. And that's really what got me - if you look back to the seminal moment for me - what got me sitting here today - it was really that decision.
Shontell: It's no wonder you're the head of essentially a media company now. So BIB, was the "Beginnings in Boston" newspaper that you started. And the way you got into that, I guess you had been cold-calling executives, just hoping they would talk to you? And you discovered that nobody would talk to you unless you were a reporter?
Armstrong: I was calling people in Boston. I was really trying to just figure out what I wanted to do, and learn about different careers. I again had thought that banking would be something I would be really interested in, but when I realized it wasn't, I thought, "I should go do research and find out, really, what I want to do." And so I would call different executives in Boston, CEOs of companies, and see if they would meet with me, and not many of them would. I called one of a very large financial institution in Boston, and the woman was very nice on the phone, the CEO's assistant. She said, "You know, the only people who really cold-call here, or who get through to the CEO, are journalists."
Later that night, I was talking to my roommate and I said, "You know what we should do? We have all our friends in their 20s, everyone's finding jobs or figuring out what they want to do - why don't we start a publication to get advice from all of these people, and give it to them? Boston's filled with young people graduating."
So we decided to launch the magazine. It was targeted at exactly my demographic back then, and I didn't know anything about publishing newspapers or magazines, but we basically launched from scratch.
We sold everything we owned - cars, bikes, surfboards, the whole thing. We bought an Apple Quadra 650 computer. And we basically learned how to publish from scratch, and print from scratch, distribute from scratch.
In that journey, I learned probably the most I've ever learned, just about what a business is from start to finish. And it was a wonderful experience. It was really hard. We did an OK job at it, not great. And we ended up buying a second newspaper, which was a better idea. That was in Cambridge and Harvard Square. So that was the launch of my phone calls to newspaper ownership, in a very short time period.
Shontell: It sounds like you never had a problem cold-calling people, which is Sales 101. So it's not really surprising that you ended up having a career in that. But you were telling me a funny story before this podcast, about how actor Casey Affleck used to work with you?
Armstrong: So we bought the second newspaper, The Square Deal, and if you went to Harvard back in those days, you used it. It had coupons in the back; it told you what was happening around town, in Cambridge Square. And we hired people, kids from Harvard, to hand them out to other Harvard students.
I was at a dinner a couple of years ago, when Casey Affleck said to me, "Hey do you remember me? Do I look familiar?"
And I said, "Yeah, of course you're familiar - you strike me as very familiar."
He said, "You don't remember, but I used to work at The Square Deal and hand out the newspapers for you." Obviously he's done really well, and he's not handing out newspapers anymore, for sure. I think he's even won an Academy Award, so that was a fun story, and a good memory back to the old days.
Armstrong: Another friend of mine, Peter Dunn, owned a store in Boston called Cool Beans, which was a Grateful Dead store. And he was very networked in the Cambridge and MIT communities. He said, "Hey, there are some people coming. They have this new thing called an "internet browser." We're going to meet down at MIT, and you can see it."
I went down, and literally within one minute of them turning it on and showing what the browser did, I looked at my friend and said, "I'm selling my newspaper as soon as I got back to the office. I'm going to go do this thing. This is 100 times easier, faster, and more scalable than what we're doing in the newspaper business."
And so I literally went back, called my parents on the way home from that meeting, and I said, "I'm selling the newspaper. I'm going to try to move to an internet environment."
We started actually trying to put our newspapers online. This is 1994, I think. And then, long story short, I moved pretty quickly. We sold our share in the newspaper back to another publisher in Boston, and then I went off to start doing internet things, which was a lot of fun.
Shontell: So you rise as this great salesperson, with the first internet magazine, I believe. And the company you end up later working for gets acquired by Disney?
Armstrong: Yes. After the newspaper, the only thing I found right away - because not many people were doing internet things - was IDG, the big tech publisher, was launching the first internet magazine, which was a magazine about the coming internet.
I went to work there. In those travels - it's an incredibly long story - but I went to an event with the founders of NASCAR, the France family. And the Frances got up and gave a presentation about where they thought this internet thing was going. I talked to the NASCAR family, and they basically said, "Look, there's this company. Paul Allen's starting a company on the West Coast called 'Star Wave.'"
Shontell: Microsoft cofounder Paul Allen, right?
Armstrong: Yes. And they were the first real content company on the internet. So when I got back to Boston from that trip, I had a voicemail on my phone from Star Wave. And they said, "Hey, we heard you're in Boston. We hear you're doing internet things, and you're trying to do advertising and content on the internet. We have a company in Seattle. Would you like to come out and visit us?" So I flew out to Seattle. I did a day's worth of interviews and got offered the job at the end of the day. I went back, moved from Boston with a bag of clothes - I didn't own anything else at the time -and moved to Seattle. And I had an awesome experience out of Star Wave.
We launched ESPN.com, NFL.com, ABCnews.com, and worked with a whole crew of people from all over the US who had moved there to really get into internet content. And that was an amazing experience. Then Disney bought us. I ended up moving back to New York, to work for Disney, helping them get their internet things off the ground, including ESPN and ABC.
Shontell: From what I understand, you were pretty young when you went out to Seattle. You were in your mid-20s maybe, and you were working across platforms, which was a really early concept of TV-plus-digital, plus all these things. And you're also working with the legacy-TV sales guys, who are the old guys who've worked their way up to the top. How did they let you in? Why were you such a good salesman?
Armstrong: Well, one is, when I was at Star Wave in Seattle originally, I had done, at the time, the largest deal on the internet ever done. So I did a $1 million deal back in probably 1996 or 1997. And this was when most of the deals were $10,000 deals. I got on Paul Allen's radar screen. I ended up flying down to a Portland Trailblazers game with Paul Allen and some friends from Star Wave. And then when Disney bought the company and I moved to New York, people knew about this deal.
The deal I had done was with Rick Scott, who's now the governor of Florida. He was the CEO of Columbia/HCA, and he did the first really, truly large ad deal at Star Wave and for ESPN. When I got to New York, I sort of had a reputation of somebody who was energetic, creative, and doing deals.
I showed up in New York, and I was really one of only a couple internet people there. It was a little bit more like we were outside-the-box people who didn't fit into the normal way that everything was happening in New York and media. So they kind of took us everywhere. It was sort of like a dog-and-pony show, and we were the dog.
I learned a lot from working at ESPN, which was an amazing company with amazing people. I got to spend a lot of time with people who were super knowledgeable about advertising and super knowledgeable about content. I became, like, their internet buddy.
What it's like to be interviewed by Google cofounders Larry Page and Sergey Brin
Shontell: That served you well, because then Google came calling. Google at the time was this tiny startup. It was barely generating any revenue. Omid Kordestani, who's now the executive chairman of Twitter, calls you up.
Armstrong: Right.
Shontell: And he's at Google at the time. What does he say and what's that meeting like?
Armstrong: Omid had called, through another woman I worked with at Star Wave. And he said, "Can you meet me in New York City?" I met him at the Carlisle Hotel in New York on a rainy Friday. And we hit it off right away. If you know Omid, he's one of the best humans on the planet, and one of the most engaging.
At that time, Google was into licensing software. That was the main business model at that point. And they were thinking about getting more into advertising, so Omid asked me a whole bunch of questions about what I thought, and I ended up going out to meet and have breakfast with Sergey Brin in Palo Alto.
I had had another job offer at the time from a large gaming company, an unbelievable job. Which would have, at my age, been super enticing. But after meeting Omid and Larry Page and Sergey Brin, and some other people from Google, you could tell there was going to be magic there. And it wasn't exactly clear what it was going to be, but I decided to join Google, and that was a great decision. A lot of fun, and just an unbelievable experience. And again, super-talented people. It was a highlight for me.
Shontell: Do you remember what that first meeting with Larry and Sergey was like? What is it like meeting the Google founders back then, as they're growing it?
Armstrong: I don't think I've ever told this story. But when I had my first discussion with them, they basically said at the beginning of the meeting, after a few questions, "We're not really sure what to ask you. Ask yourself the questions. Like, what questions would you ask yourself, if you were us?"
So I said, "Look, I'm very direct person, very honest. Here's what I would ask, the following questions." And I thought that was interesting. I realized later, after working with them, that that was not an anomaly, that was one of their tactics.
But they were driven. I think to this day, Larry and Sergey are obviously very smart, and very creative. They're very competitive also, in a good way. I'd say they care a lot. At their size now and what they're doing, I'm sure there's a lot of feedback on them, how people feel about them. But they're, at their heart, very good people. Both of them.
Creating AdSense for Google, from scratch
Armstrong: First of all, Salar Kamangar used to be the head of YouTube and was really the brainchild behind AdWords, and a few other people we worked with. Really, it all kind of came together in a very mad-scientist way, of how AdWords got off the ground, and the ad business. But there were a whole bunch of us working on it, and it had a good outcome on the AdWords side.
And then one day a guy named John Firm, who worked in our ad-sales group, came and said, "Hey, we have a whole bunch of customers who don't have budgets spent on search. They basically load all their budgets in. There's lot of room for other places they could run it, but we can't spend all their money."
And by the way, one of our publishers, About.com, said, "Is there any way for you guys to help us figure out how to make more money?" And so we literally took a PowerPoint page, mocked up a content page, and put AdWord boxes on it that were laid into the content. We took it into the Google meeting, to the executive-team meeting, and said, "Hey, why don't we syndicate all of our ads onto content properties?"
Which today doesn't sound like brain surgery, but it was a moment in the company's history when there were a whole bunch of people who didn't want to do it. They were like, "We're a search company. Let's stay focused on search. This doesn't make any sense. Display ads don't really work."
There was a big argument, back and forth, but at the end of the day we got a group of engineers. We hired Kurt Abrahamson, who was the president of Jupiter, to come and run it. We spend about a year in my group developing it and growing it, and then we turned it over to Susan Wojcicki, who's running YouTube now. She took it over and ran it.
Then Applied Semantics was a company that was bought by the product and engineering team, so that was another product that had a lot of founders to it, I guess, and a lot of success because a lot of energy got put into it.
One untold story about Google I should have gone back to is, one of the reasons Google is successful in ads is because the search-licensing business went away. Yahoo bought Inktomi, and so one of Google's major revenue lines kind of went away, because search licensing went to a free model from a paid model. That allowed a lot of the engineering talent at Google to go focus on ads. I think without that type of transition, we never would have had the horsepower in terms of the intellectual capital on engineering a product.
Sometimes in business you get lucky, and what looked like a bad situation with the licensing business turned out to be an unbelievably big opportunity. And that's really what led to AdWords. And with the DoubleClick acquisition, there was lots of stuff like that that came out of it. What looked like a tough situation originally turned out to be a boon for the entire company.
Shontell: So this works. You become this god within Google, managing this massive department.
Armstrong: I was not a god within Google. There were a lot of gods within Google. So there was a massively talented team there. Unbelievable talent, yeah.
A call from Jeff Bewkes
Armstrong: You know, a few things I would go back to. The reason I ended up going to Google was that it looked like there was a huge opportunity in the information business, and putting information connected with where commerce happens, was a big opportunity. Earlier in the 2000s I had cofounded and funded a company with my college roommate, Luke Beatty, called Associated Content, which was more of a content company that eventually got sold to Yahoo.
But my time at Google, I'd say after I was there for almost 10 years, I have a personal career philosophy, which is, I think you should continue to do something as long as you're learning quantum number of things in general. And I think the quantum learning is probably the most important attribute to people's careers, to continue to grow.
At Google I just wasn't learning anymore, but my interest level over time had started to get really focused in on the content space, and where media was going, and working on Associated Content a little bit. I was on the board for a while. It got me interested in where content was going.
And then when Jeff Bewkes called, it seemed like a unique opportunity. I could go into my investing philosophy, but I'm also somebody who likes to invest. I think a lot of opportunities are opportunities because everyone can't see them. And if you can read something in the newspaper, it's probably not an opportunity anymore. And AOL was the exact opposite. It was something that everyone had given up on, but they had a lot of resources, a lot of users, and they had a lot of talent. So it seemed like an opportunity.
If I was going to do something disruptive, that'll also be a big runway to do something disruptive because people frankly were counting it out. I think that you have a choice to go to a startup to start something, or you have a choice to do something at bigger scale. I wanted to do something at bigger scale.
And it was just an interesting asset. It was probably going to be a windy path, because it was inside of Time Warner. If we wanted to spin it out, we'd have to go through the whole process of spinning it out, and then we'd have to make all these changes to the company, and it was a challenging experience, and that's what I wanted at the time.
How to weigh a big, risky career move and leave your safe, cushy job
Armstrong: Yeah, you know, it's interesting. I didn't want to take the job if I didn't think I could do it. And I definitely had a lot of reflection time on that, because a lot of these companies that have these situations have a lot of CEOs, and they're all smart people. They are good at their careers. I was carefully thinking about it, but on the other hand I thought: What if this totally fails and it's the world's biggest failure? Really - who cares? I'll probably learn more doing it.
A lot of people said to me, "Why would you ever leave Google? Why would you leave Google and your reputation at Google to go do something like AOL?" But I thought about it the opposite way, which was, if you wanted to have the most intense learning experience, and apply a lot of the skills I had learned in the 10 or 15 years prior, AOL seemed like a great opportunity to do that. My personality is more entrepreneurial, and it just seemed like an opportunity that, although it had tons of risk, it also had tons of opportunity. And you've got to be willing.
My dad said to me the night before I started at AOL, "This is a burn-the-bridge moment. If you fail at this, you can't walk backward. So you should figure out how to always look forward."
And I think that was a great piece of advice, because that's essentially what we had to do, over and over and over again.
Shontell: How do you make a burn-the-bridge decision? How do you know you're making the right choice? Especially as the leader of a huge company?
Armstrong: One thing is, when I took the AOL job, I traveled around and went on a little mini leadership roadshow before I actually started.
I got to announce that I was going to start, and then I had some time before I started and I spent a lot of time with a lot of different leaders, who I respected, who are big leaders across corporate America and some entrepreneurs.
Essentially, I think in a CEO job, you have to be OK with risk and you have to be OK with failure. I have a saying which is, "You have to fail toward a goal."
As long as you're failing, if you know what the goal is, it's OK to fail in that direction. And that's the advice I got from people. On that roadshow, I had a lot of people challenge me. The best mentors I had are also the most challenging people. And on that roadshow, they asked me a lot of the questions I ended up facing further on. I wasn't prepared for all of them but I kind of knew what the role was, and what the job was going to be. And fortunately, or unfortunately, for AOL, a lot of that I learned on the job overall. So it was challenging.
Shontell: And when you come into a new job like that, do you need to bring your own team with you? Because that's something you did. You cleared out the executives, brought in some people from Google. Was that essential?
Armstrong: When I first started I brought a couple people like Maureen Sullivan, who's the president who runs Rent the Runway now. She was the first person who came over from Google with me. And what I told the AOL team was, "Look, this is the team. Everyone's going to have their shot. We have to change what we're doing. Some of the changes, if you want to roll with them and stick with them, great. If this is not what you want to do, raise your hand, because we're going to go in a different direction." And I think over time I did end up bringing a bunch of people in from Google, and other people as well.
I would say looking back on it, overall, you had a very challenged company. Out of the gates, we were trying to spin a company out of a public company and take it public alone, which is a massive challenge. Forget about one that's in a downturn, overall. I think there was a whole group of us who were somewhat experienced, but not fully experienced in doing all the things that we were doing. So we were figuring it out on the fly.
I bet if you went back and talked to a lot of those people, it was probably one of the best - and hardest - but best learning experience. If I went back to it now, at my experience level, I would probably take a step back and take a better account of my own skills of what I was really good at, and what I was not good at. And I probably would have augmented the team slightly. Not that I wouldn't have brought the people in from Google, but I would have had a couple other people around me who had more experience, and I think that was a lesson, and something I'm frankly taking into the Yahoo deal we're working on now.
How to inspire a team when morale is low
Armstrong: We did a 100-day process, and I traveled around the whole globe. There were about 10,000 AOL employees at the time, I saw about 9,000 of them in person, and I had three processes I was running: feedback from the entire company and team, feedback from the management team, and then a list I was keeping of things that I thought we should be doing.
After the 100 days, we held a meeting at the Time Warner Center and I put up three whiteboards. On one white board I wrote back the results from the entire global team of what they thought we should invest in. I put up a white board of what the management team thought, and I put up a whiteboard of what I thought. I flipped them all around at the same time. Each one had five things on them. All of the white boards were identical, except for one area on the white board that I had flipped around on my personal side.
So the whole company was already in alignment and I think that got people excited. They weren't told what the strategy was. They got input, and everyone was on the same path in believing in it.
A meeting with Verizon's CEO that led to a $4.4 billion deal
Shontell: Down the road, Lowell McAdam, the CEO of Verizon, and you have a conversation. Verizon ends up buying AOL for $4.4 billion. How did that conversation start, and how do you decide, as the head of a huge company, that this was the right move?
Armstrong: There were two things. Lowell is an incredible CEO at Verizon, and somebody who really helped grow it from a wire line to wireless - and Verizon to become one of the most successful companies on the planet in doing so.
When I sat down with Lowell, it was one-on-one. It was at the Allen and Co. conference at what they call the "duck pond," where people kind of have meetings after the conference is over. And essentially I had a blank sheet of paper and Lowell asked me a number of questions. Things like, where the industry is going, what the structure would be, and what I thought was happening. I drew him a diagram of what I thought was happening. We talked for an hour or two about it, and then I didn't see him for months afterward, and then he called.
We had talked about [how] maybe there are operational things to do together between the companies, and then he called and came back in the fall. I met with him, and we had more and more conversations. So over the course of time, there was a very natural progression of where things were going. On the AOL front, what was happening was everything was going mobile and everything was going data-driven. I used to carry around a five-column chart from our board-of-directors meetings that I started every meeting with, that had the strategic priorities for the company.
Mobile, video, and data were the first three things on that chart, and I knew we needed to solve that issue. And Verizon, at the time, wanted to solve their challenge of, how do they grow services? So what naturally grew out of that conversation was a combination of what Verizon needed to solve and what we needed to solve.
It didn't start out as an M&A deal. It started as a big operational deal, then it went to a joint venture, then it went to a full company sale. But that's how it started. And at the same time, there were other companies kicking the tires on AOL, and we were meeting with people, but the reality was Verizon, if you think the future is mobile, then it's going to be about video and data.
It's hard to argue Verizon wasn't a great outcome for us as a business. I've been there for two years now; it's been a great experience.
Shontell: One thing that's happening in the broader media landscape in digital is this term "duopoly." A lot of media executives keep talking about it - it's the idea that Google and Facebook. the duo, are taking a ginormous share of all digital-ad dollars. There was recent a study from IAB that showed 89% of the digital money was going to those two, and 11% was going to everybody else, like AOL or Business Insider. How do you look at this landscape and what AOL's role can be? Where is everything going, in your opinion?
Armstrong: I think you have got to add Amazon to that list.
Shontell: A "triopoly."
The digital triopoly of Google, Facebook, and Amazon - and how everyone else can survive
We're a big publisher; we're one of the largest publishers on the web with our content, and we're one of the larger ad players. So it's challenging, but you have a choice. I'll give you the choice.
You have a choice of being in an industry that's growing at 15, 20, 30% globally. The internet is going to double in the next five years in terms of people who are connecting to it, through mobile. Only 15% of commerce by 2020 is going to be on the internet. There's huge opportunity in front of us.
You have a choice as a leader and as a company. You can go compete in linear spaces or offline spaces that are really challenged, or you can go into a space that's growing and you compete against gold-medal Olympic athletes. It's tough to say Google and Facebook aren't executing at the top of their game. Same thing with Amazon. But that sets an awesome bar for us as a company to compete at that level. And it challenges us creatively to try to get in that game.
From where we sit right now, I'd choose the tailwind industry that's growing, and I would choose to have Olympic-gold-medal competitors, because it's only going to raise our game.
With the industry, I have a whole viewpoint on industry consolidation, but where the world's going, we're heading to a place where there's going to be giant scale we've never seen before globally. There's going to be a set of companies that have the abilities to do that. And those companies are going to really, really have the chances to build companies the size that the world hasn't seen before.
Shontell: A final question: You've had to make a lot of hard decisions as a leader of many companies at this point. But you're also personable and a likable guy. How do you strike that balance between gaining respect from your employees and making the hard choices, and being liked and respected at a manager?
The advice Tim gives to his children, and to anyone building a career
Armstrong: There's advice I got when I was growing up - and I give it to my own kids - which is: To thine own self be true. What you see is what you get. If you interact with me, this is who I am, love me or hate me. And I think being authentic is important.
The second thing is, the mentor crew I have. I have a bunch of advice I always give to younger people, but one of them is to build your personal entourage or board of directors.
I have five or eight people outside the company I rely on. I have one person, David Bell, who used to be the CEO of IPG. He's in our office almost every day. I meet with him every Friday. And every Friday he starts by telling me everything I'm doing wrong. For me, it's the most helpful meeting of the week because it always resets me back to, "OK, what am I supposed to be doing as a leader? What's my job? What are those things? If you're yourself, and you're authentic, and you're honest and direct.
The other thing I've learned from David and people like [former Starbucks CEO] Howard Schultz and [American Express CEO] Ken Chenault and other people like that who have mentored me over time is, just be direct with people.
I did an all-company meeting with AOL and Yahoo yesterday. I got asked if there are going to be impacts from doing the deal. I said, "Yes, there are. That's what happens when two companies come together."
I'm not going to beat around the bush. We're going to try to do the least amount we possibly can, but the bottom line is, that's part of what's happening with the deal and I want to be direct about it. So that directness, I think, helps a lot, and being honest with yourself.