I started this interview with the kind of focus you’ve come to expect from me, but then I found out what book Kevin O’Connor was reading and I ended up having a more philosophical discussion.
So you’ll get the “how he did it” story in this interview and find out how Kevin launched a company in his basement that ended up leading an industry. In 1995 he launched what became DoubleClick, Internet ad-technology company that was sold to Google in 2007 for $3.1 billion. And you’ll find out how he’s following it up with FindTheBest, a comparison engine which lets you compare smartphones, cigars and more.
But, because he’s been reading the biography of Andrew Carnegie, you’ll also hear us talk in a more general and philosophical way about how picking up on successful people’s patterns can influence you.
Kevin O’Connor, O'Connor Ventures
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Let’s get started.
Andrew: Hi, everyone. My name is Andrew Warner. I’m the founder of Mixergy.com, home of the ambitious upstart, and you guys know the mission behind the website. It’s to bring successful internet entrepreneurs to share the experiences behind their businesses and teach what they’ve learned as they’ve built their companies.
Joining me today is Kevin O’Connor. In 1995, he launched the internet advertising network from his basement. That company went on to become Double Click, the internet ad technology powerhouse that was most recently sold to Google for $3.1 billion in 2007.
I invited him here to tell the story behind Double Click. I’m also curious to hear about his latest company, FindTheBest. It’s a comparison engine that lets you compare smart phones, cigars, and so much more. Kevin, welcome and looking forward to the stories.
Kevin: Hey Andrew, great to be here.
Andrew: I love metrics. How about if we start off with a number? I know that the site is fairly new. But, how many people do you have on FindTheBest.com every month now?
Kevin: We launched in August of last year. We’re up to about 1.5 million visitors a month across 500 comparison topics.
Kevin: When TechCrunch wrote about you, first of all, Michael Harrington loved the company. Does he happen to be an investor?
Kevin: He’s not, no.
Andrew: He’s not. So, just pure love for the, maybe not love, I don’t want to mischaracterize it. But he said, “Keep an eye on this one. This one looks like a hit.” He also said that you didn’t buy any traffic. Has that changed since then? Or are the millions still all organic?
Kevin: No, it’s all organic. Search engines is a big part of it. A lot of people syndicate our content, so embed it in their blogs. Probably 2,000 sites are doing that and [??] traffic.
Andrew: How do you get bloggers to embed anything in their sites anymore? It feels like most people just want to blog and that’s it. They don’t want to use widgets and anything else.
Kevin: It is a challenge to get people to get content in a way that’s useful for their blog, right. They don’t want people to leave. That’s really what we’re focused on is giving them great, objective content that relates to their audience. For example, there’s a beer blogger and giving them a comparison for beers. Or whether it’s dogs, helping their users find the best dog breed.
Andrew: Okay. Do you have someone in the company whose job is to be an evangelist to bloggers and to connect with them and help them? You do. What’s that role like?
Kevin: We have a couple of guys. Blogger outreach, lots of grassroots efforts, reaching out to whether it’s universities or governments, saying, “Hey, we’ve taken really interesting information that could help your econ students.” Reaching out to bloggers and so this can help your users.
We just hired Rabine Yaghoubi as president of the company. He was a former Double Click and Google guy, really focused on business development and content distribution. He’s going to be a huge addition.
Andrew: I want to talk about both companies. But before I even ask about Double Click, how does it feel to go back to 1995 and answer questions about a company that you started years ago?
Kevin: It was a fun time. I’d like to look forward to the future. But that was such a unique time in history. It was wild. By the way, just a little trivia that most people don’t know. This is how bad I am at coming up with names. Our original company name was Internet Advertising Federation.
Andrew: Oh, wow.
Kevin: Not that I’m a big Trekkie fan but it definitely sound very Trekkie.
Andrew: What was the vision that led you to the word federation? What were you thinking that the federation represented or would represent?
Kevin: The theory was going to be that content was going to separate from physical distribution, right. So you remember copy, well, those were all tied together and the Internet was going to really release it. We always envisioned this federation of websites that we would unite initially for subscriptions, but ultimately for advertising.
Andrew: Subscriptions, all right. I’ve got to come back to that. But let me first thank you for being so open about it, because what I’ve found is that a lot of entrepreneurs don’t like to look back. Like if I say, “Hey, let’s talk about a company you started earlier in your career,” they say, “No, Andrew, I want to focus on the future.” To me, that’s such a waste, because we built these, “we” I say, you and the people who do interviews here on Mixergy, built these incredible companies. I don’t want those stories to just disappear. I want them to be as useful and as heralded as the stories of the guys like Andrew Carnegie which many of us grew up on or Bill Gates.
Kevin: I’m reading his bio right now.
Andrew: The bio, the one with just a picture of him on a white background?
Andrew: Isn’t it a little depressing? It feels like a lot of what that book says contradicts, basically it feels like the author is calling Andrew Carnegie a liar or an exaggerator. What do you think?
Kevin: I think probably just the opposite. They guy’s working in a time frame that is completely different from what it is now. There really were no public markets back then. Carnegie actually avoided all that. It was interesting the way there was pretty cozy, quasi kickback relationships with the government. But I’m not sure things have changed that much either. I don’t know. It was interesting. I thought that he had spent his whole life. I didn’t realize that he was really a, sort of a hands-off operator.
Andrew: So you see, now, just the way that you are reading about Andrew Carnegie, my vision is that people a hundred years from now will be studying the Kevin O’Connor story. Let me ask you this, before I even get into your story, what do you get out of reading books about other entrepreneurs or studying their stories?
Kevin: What I always look for, I did a lot of startups and a lot of investing in companies, and just meeting and learning about how people have done it. I’m just looking for patterns. I’m kind of a, I don’t know, maybe brain man in that way. I’m always looking for patterns, what’s worked and what hasn’t. I try to stay away from anecdotes. That’s one of the dangerous things you can get in programs like this, people looking for, what happened for me. It was a confluence of events. There are lots of things that went on. But looking for things you can control. That’s really what I focus on. I wrote a book on innovation and how to create companies. I try to boil it down to what are the three or four things that you can really do to influence an outcome.
Andrew: What are those three or four things?
Kevin: Well, one of them is really simple and we always forget it. I always ask MBA students, “What’s the fundamental purpose of a company?” I used to hate when people would do strategies, these five-year strategies about increasing profits and gross margins. That’s nothing to do with the company. It’s all about solving a problem. It’s really that simple. I really obsess on how do you identify a fundamental problem a company has and then how to you apply technology into solving that problem more efficiently than anybody else. That’s by far, number one.
The other one is just really highly focused strategy and hiring what I call “smart athletes,” super competitive, high IQ people.
Andrew: Okay. I’m going to do what the New York Times did to you when you told them what you were looking for when you were hiring people. They turned around on you and said, “Well, what about you?” How about one other thing that’s key to a successful company that you discovered as you were looking for patterns?
Kevin: Really, a passion. And what I always look for, I want a, especially a tech company headed by a tech guy or woman. Guy, I’m from the Midwest. It’s transgender? That’s not the right word, crossgender. So, I’m looking for somebody that’s super passionate about technology and is a technologist.
Andrew: Super passionate about the technology and is a technologist himself?
Andrew: Okay. All right. So let’s go back now in time. This is 1995. You decide that the Internet is the place I want to be. What was it about the Internet back then that you saw that so many other people missed back then?
Kevin: I think the big thing was that looking into the future, that anybody anywhere could have access to the world’s information was just an absolutely, how could that not be massive. I didn’t know about all the mobile devices coming. I mean, cell phones were clunky back then. I figured that PCs would absolutely be ubiquitous. Internet connectivity would be ubiquitous to everybody, that we would have a common terminal that would access infinite amounts of information, and that’s kind of where we are today. To me, that was a slam dunk. Because sometimes I’m very skeptical of technology because 99% of technology never goes anywhere. It’s a bunch of marketing hype. Or it’s just impossible to do, at least over some framework of time. But this one was just inevitable. Just like the PC. When I first saw the PC in 1983, it’s like, that’s inevitable. That’s not even a question.
Andrew: And you worked at Intercomputer Communications Corporation. I’m looking at my notes here, so I don’t have this all memorized. But that’s where you helped connect microcomputers. Actually, what did you do there? Instead of me reading from my notes, I might as well have it come from you.
Kevin: That was the first startup that we did, right out of college. I was going to go get my Ph.D. That was my view. But these guys like Jobs and Gates were nobodies. They were just coming out, emerging, really pretty exciting. So we tied some of the first PCs into mainframe computers, which is what was running corporate America at the time. I remember, we were really excited. We created the product, and now we’re going to sell it. We took an ad out, waiting for the phone calls, and nobody called. So we started calling companies. The first hundred calls were, “There will never be a PC in my company, over my dead body.” Fortunately, about six months later, they called back and said, “You know what? There are PCs in my company. Now the CEO’s got one and I’ve got to connect it.”
Andrew: I see. So, the CEO would go out and buy his own computer, put it on his desk, play around with it, feel all kinds of power. Now the IT person had to connect it to the mainframe. To do what?
Kevin: Back in those days, the IT department had a stranglehold on any computer coming in. So people were bringing in computers, buying them as actual accounting machines, calculators, word processors, typewriters, anti-typewriters. So they were actually bringing them in as anything but a computer. Then all of a sudden, there were hundreds of these computers, if not thousands, and they would need to be tied in. Guys would literally have a terminal over here and a PC over here. It was a tough struggle.
Andrew: I see. So that the computer can access the data that the terminal would have given them as a separate machine.
Kevin: And then they wanted to be able to be able to bring the mainframe data down into the PC and into their spreadsheets or word documents.
Andrew: So was it just as you described, a lot of cold calling over and over? And then finally return calls from people?
Kevin: Yeah. And I think that’s the most brutal part about doing a startup, especially in an emerging technology market, is that it seems inevitable. When I talk to kids at college today, they’ve always known nothing but the Internet. These things were not inevitable. These were all highly resistive things, highly, highly resistive things.
Andrew: So, how would you get the companies to remember you when it was finally time, a month or six months later, to make the move?
Kevin: In those early days, we would always try to act as an educational resource. That worked great on the Internet. Because all of a sudden it does nit, and these guys are up a creek without a paddle and they need to come up to speed very, very quickly. One of my favorite questions I used to get is, “A lot of these CEOs don’t use the Internet. What are you going to do? How are you going to get past that?” And I said, “Well, the CEOs will all be dead. They’ll either be dead in five years, not dead, they’ll be out of a job or gone.” Eventually, it all comes around. I call it the “technology absorption curve.” It takes so long, it takes about seven years I think for a market to really hit critical mass. The Internet happened a lot quicker. Smart phones has happened even quicker. For some reason, it’s accelerating.
Andrew: When you say that you did a lot of education to stay top of mind and be the guy that people called when it was time to make the move. What kind of education would you do that would stick? Today I can understand. You’d just blog over and over and you’d be the person talking and teaching about a topic until customers are ready to buy. But back then, what would you do? Brochures, do seminars?
Kevin: A lot of seminars.
Andrew: A lot of seminars.
Kevin: Yeah, seminars are very effective. We would write in industrial rags and it was guest blogging. We would write guest articles. Not selling our company but just telling people how to help them to achieve what they’ve got to achieve.
Andrew: This would be you teaching in the seminars?
Kevin: Yeah, sure. Back in the early days, you do everything.
Andrew: It’s so interesting. In preparation for this interview, I did a lot of research on you. But for some reason, the articles kept saying over and over, you don’t have an advertising background, and they said it in a way that would kind of imply that the guy doesn’t know how to sell. He was a tech person. He came from behind the computer and joined Poppe Tyson who were advertisers. But it sounds like you were a salesman from the beginning, that you at least had the ability to persuade and communicate clearly. No?
Kevin: Yeah, I was a telemarketer in high school.
Andrew: You were? What did you telemarket?
Kevin: Heating and cleaning services. I got fired. Or I quit. I can’t remember. So I was a salesman baptized in fire out of necessity in the first company. We had to sell to stay in business. But I also realized, I was an engineer that hung out with business school people. I’m less of a sales guy than an evangelist. I get out there and I believe, and I’m very passionate about what we do. I wouldn’t be doing it unless I thought there was a big need that we could satisfy. So I always try to position it that way. What’s your problem? How can I help solve your problem? How can I make you more money, save you more money?
Andrew: I understand your point about anecdotes. But I’m wondering if you have one from the days when you telemarketed. One little story that sticks in your head, that when it’s time for you to sell, you think about, oh I learned that in that one incident.
Kevin: Oh, tough one. I think we’re having a bandwidth problem.
Andrew: Sorry? Nothing coming to mind?
Kevin: No, no. I thought we were having a bandwidth problem.
Andrew: Oh, okay.
Kevin: Nothing is coming to mind. No single incident.
Andrew: Okay. I did telemarketing once in high school and I remember the assumed close that you’d say, “I’ll start you off with a newspaper this coming Monday and you’d just have to pay once a month, only $5, and I’ll set it up right now. Okay?” And if you said that, people would find themselves just saying okay, just instantly apparently.
Kevin: Yes, that’s a good point. I found telemarket a little bit, stuff we shouldn’t do in sales. But that was one of the techniques that you learned very quickly. You don’t let them make a decision. We’ll send a truck out to you on Saturday. Does 10:00 or 11:00 work? The truck’s coming, so pick your time.
Andrew: It feels like it would be a confidence builder, to be able to do that and experiment over and over until you either quit or get fired. Did you find that for yourself? Is that where the confidence came from?
Kevin: That’s a good question. I think it’s less about confidence building than getting over fear of rejection. So, I was always terrible at getting dates. I would only ask a girl out if I knew 100% if she was interested in me, because I didn’t want to get rejected. So, that was the same thing with selling. It is a numbers game. Most people are going to say no.
Andrew: I see. And I can see how being told no over and over again would help get you over that. By the way, I’ve got to apologize to you for the technology, up until a moment ago, the video for some reason made you look tan and, like you were in an orange room. But it now cleared up and can see you as the way you are in real life. I said, “Boy, this guy’s getting a lot of sun in Santa Barbara.”
Kevin: We do get a lot of sun. I did look pretty orange.
Andrew: But it’s all coming in okay now. All right. So, I read that you spent eight months with your co-founder, Dwight Merriman, just thinking up business ideas. I’m wondering about the ideas that you rejected, as a way of understanding your thought process. Do you remember one or two of them?
Kevin: So, the big one we screwed up, and this was a good reminder, you’ve got to ask the right questions. Is we came up with basically what it is classified job listings online. So Monster and Career and Builder and all that. So, that was our idea. What if we could build a service for posting resumes and getting jobs? I went out and asked a bunch of [??] human resources, “Would you post your job online?” They all come back and said, “No. Why would we do that? First of all, I don’t know what you’re talking about. I don’t know what the Internet is. Or why would I post it online because no one’s on there. There’s less than a million people on the Internet today.” So, it was completely the wrong question. The question should have been, if you could reach out and get people anywhere in the world who is a perfect fit for your company at a really cheap price and do it quicker than you’re doing now, would you do it? Of course, the answer’s yes. And so we abandoned that idea.
Andrew: Wow. So how do you know today whether the problem is the way you’re asking the question or the product that you’re asking about?
Kevin: I think you’ve got to ask, you can’t ask about the product, you’ve got to ask about the problem.
Andrew: I see.
Kevin: You’ve got to really understand what is the problem you’re trying to solve. That is what we did with Double Click. It was very exciting. You’re right. I didn’t know anything about advertising or direct response. We went out and bought the definitive textbooks on direct response. Ed Nash, brilliant book on direct response. Then we bought, I can’t remember the book, on advertising. but we realized as we went through it that this is the foundation of what advertisers want to do. They couldn’t accomplish any of it because it was impossible to disconnect the media. We realized that we could actually do 99% of what they were talking about. So we modeled, we used terminology, so we very quickly learned all that stuff. And I have a model that, if you can learn a DFT, discrete fourier transform, which is what I learned in electrical engineering school, advertising business isn’t that tough. Learning the basics of advertising was pretty easy. I think that was our big advantage, why we moved to New York. Is that, we knew technology. We didn’t know publishing and advertising. That was our weakness. I mean, if I have any strengths at all, it’s realizing where I’m stupid, which is a lot of places. So you tend to either find people that complement you or you immerse yourself in an area to make yourself smarter.
Andrew: Why did you pick Dwight? How did he complement you?
Kevin: That’s a longer story. When our first company got bought by DC [??] Atlanta, we were going to move down there and start a research group. So I started asking around the company, “Who’s the smartest guy? Who’s the smartest guy?” expecting it was going to be one of the people who had been there a long time. You’ve got to talk to this Dwight guy. He’s only been here six months, right out of school, but he’s brilliant. So, I had Dwight come into the office. I said, “Dwight, what do you know about me? What have you heard?” And he goes, “Well, I’ve heard you can be an asshole.” And I was, like, perfect. This is what I need. Here’s a young guy who’s willing to tell me that my crap stinks. I needed someone who is just brutally honest who is really, really smart. And Dwight turned out to be. He really is one of the great engineers on the planet.
Andrew: You’re an engineer yourself. How does Dwight’s engineering complement yours? Or is it just two great engineers will figure things out and more than double their results?
Kevin: You know, I had done 10 years of programming and moved more into management for all sorts of different reasons. Dwight was a software developer, just a great, great software developer. Sort of the next generation of software developer. My software development skills are more important when getting close to the hardware was more important. Now, it’s more about the algorithms and scaling and stuff like that.
Andrew: So, you told us how you were asking the wrong question when it came to online classifieds. How did you phrase the question that led you to understand that Double Click was right? It was solving a problem that needed solved?
Kevin: So that was a tougher one because we were originally going to federate sites for subscriptions, and we were really trying to figure out what is going to be the economic basis of the Internet. E-commerce, subscription, or advertising? So we just looked at historically what has always won in every media and it’s been advertising. So that was that one night I still remember it was August. I went upstairs to my wife and said, “Our research is done. We’re starting a company tomorrow.” Dwight and I had come up with that simple twist and realized that all the pieces fell into place.
Andrew: What was the twist that made all the pieces fall into place?
Kevin: That we took the concept of building a network of subscriptions. You’ve got one subscription, you can go to any particular site, and to flip that around and be using that as advertising as the basis and realizing that we could solve virtually every problem that advertisers have ever faced through technology.
Andrew: I see. So, not subscriptions. You’d create a federation of sites and you’d enable people to get access to them because you’d pay for them with advertising. Do I have that right?
Andrew: I see, okay. Then, I wrote down “subscription” to come and ask you about it. Was there still a vision to add subscription later on?
Kevin: Yeah, we kind of killed it. It always came up at Double Click. Should we do this? And I still think there’s a market for that. It’s a tough one. People have done it in the adult industry. I don’t know how successful it’s been. And it would be really good for a lot of publishers because people still struggle with using advertising as the sole revenue source. I think there’s a market still.
Andrew: Okay. I’m hoping. I’m trying to do it here on Mixergy also. So, you started launching your own websites, is that right?
Kevin: And by the way, yeah, I’m involved with a company called Surfline.com. I don’t know if you’re a surfer, but they’ve done a brilliant job. They literally have half the revenue coming from subscriptions and the other half from advertising. So, it’s one of the few companies other than let’s say, The Wall Street Journal or porn sites that have really figured it out. So, if you need a good proxy, a good example.
Andrew: I’d love to be introduced to them. I’ve actually like to do a series of interviews with entrepreneurs who did make the subscription model work and try to figure out, as you say, what are the patterns there. What is it about these guys that worked when so many people have been struggling? Most famously, the New York Times for years has been looking for a way to do it.
Kevin: It would be a short series.
Andrew: I’ll dedicate just five days to all five companies who are doing it outside the porn world.
Kevin: You know what it came down to for them? And they were struggling with it for a little bit. And it’s to have that one wow feature.
Andrew: What was their one wow?
Kevin: High definition cameras of surf spots.
Andrew: That’s the wow? High definition cameras is what gets people to pull their wallets out and pay online?
Kevin: For a surfer, that’s like porn, to be able to see your surf spot in high definition.
Andrew: Oh, because it would give you a sense of whether you should go surfing that day or not, because, I see. Okay, that makes sense. All right. So you’ve got to find the wow. Let’s continue.
Kevin: I call it the MFP. That secret stuff in toothpaste that Colgate or Crest used to sell. I thought that “Social Network” movie did a good job, why I liked that movie so much. And it showed, what were the one or two things? And it always comes down to that. In every market, every product, the one or two things that separate it. It’s not 100 things. I think one of the problems that people get, here’s 100 features, 200 features. They get feature [??] they get obsessed with features. But it’s usually one or two things.
Andrew: What was it in the “Social Network”? I don’t remember that standing out in the movie.
Kevin: It was relationship status and exclusivity.
Andrew: Oh, that you couldn’t get in unless you were in a college and you wanted to find out whether the girl you were into was single or not.
Kevin: Yes. And they explained the exclusivity, where you had to be invited in order to get in, whereas MySpace at the time and most of the other ones are just open to anybody.
Andrew: What is it now at your current company, at FindTheBest.com? Have you found it?
Kevin: Yes and no. We are constantly testing. We are constantly looking to make sure that we have it. So, for us, it’s really being the consumer advocate, being completely objective. And then coming up with a rating system to allow people to more quickly assess what is best for them.
Andrew: I see. If you could come up with a rating system that unifies all the questions that I might have, so that I don’t have to look at all the different columns, then you’d have the one thing, the wow.
Kevin: Yes. And the rating system would have to be flexible enough because what’s best for you may not be what’s best for me. So, you have an overall rating system where maybe there’s a sort of general view, but I should be able to tweak it to really tailor it to myself.
Andrew: And it feels like it also needs to work across product categories. I was looking at the, there’s a question and answer section where I could, as a user, find the best question and answer site. Ask.com was the number one result on that page. And I said, ‘Why ask.com?’ I look over to the column on the right. I realize it’s automatically sorted by number of answered questions. And I realize, that’s not the way I would look at it. So, what else could I sort by? Well, I can sort by number of hits from Alexa. And I said, “That’s definitely not the way I would do it.” Because Yahoo would be ahead of Quora for example. I don’t want to get too deep into where you are today, but how do you solve a problem like that?
Kevin: It’s a tough problem. That’s one of our challenges was can you develop a platform that could be used to compare products and services from anything from mercury levels of fish to fractional aircraft programs. It’s different for each category. So, we have a lot of B2B software products where there’s a lot less information, especially pricing information. So it comes out of really products and features. Whereas, you have other information, other stuff like colleges where information can be very specific. So our goal is really to develop a platform. Quite honestly, I thought one of our big inspirations at the time when we came up with the idea was Kayak, kayak.com. I think they do a brilliant job of presenting, of trying to distill the most important information and give the power to the user to be able to figure out what’s important to them. FindTheBest is a bit of a play on words because, again, what’s best for you is not what’s best for me. And to give the filters, the sorting, give them the tools into the hands of the consumer. So they can control what’s best for them.
Andrew: I see. The name almost causes, just throws down a challenge. I’m going to show you what the best is and it almost makes the listener say, “Oh, yeah. Let me see.”
Kevin: Yeah. You know, we did a comparison on religions for example.
Andrew: Did you really?
Kevin: The best, right. We sorted by number of followers. What do you mean, Christianity is the best? We’re not saying it’s the best, we’re just sorting, sorry. It’s a challenge.
Andrew: You have a lot of guts, my friend.
Kevin: It’s a good challenge.
Andrew: All right. Let’s continue with the narrative and see where we were. All right. There was another company, Poppe Tyson. They had a company called Double Click. They actually named their business really well, no federation in that name. And they were going to sell ads online. Like you, they were going to create their own sites. Do I understand that right?
Kevin: It was Poppe Tyson and they had a division called Double Click.
Andrew: I misspronounced it, okay.
Kevin: And they were actually selling advertising on Netscape and Excite, and a couple other sites. In fact, we were selling, I don’t know, $10 million, we were virtually all of Netscape’s profit at the time. It was a little known secret that most of Netscape’s, because we were 100% profit, they had no people working on this. And it was generating a huge amount of money for them. But they never talked about it. It was almost this dirty part of Netscape. So they were selling advertising. They were one of the first advertising sales groups. I had read that they were going to launch this network. Dave [??] quoted an adage. And I was, like, “What? This is what we’re doing.” We were closer to finishing the technology to do it. So I reached out to Dave. And Dave says, “We don’t have any ability to do this, because we don’t have any of the technology. We can sell ads but we have no technology.” So we started talking and probably three weeks later, we merged the companies. It was four media sales guys and four of us down in Atlanta. So it wasn’t exactly a mega merger. And then it came down to, “Is Double Click a better name or Internet Advertising Network?” And we had Double Click.
Andrew: I’m wondering how you could make a deal like that so quickly. When you launch a company, it feels like it’s yours. You own the thing. To then go and split it with someone else, even when they’re investing money and they’re adding their own resources. Was that hard? What was that decision like?
Kevin: I’m super passionate about the company and everything. But I really look at companies as, it’s not my, it’s not my baby. It’s like family. And you’ve got to do what’s best for the family. So I always look at whether we bring in an outside investor, whether we merge the company, sell it, go public, or whatever we do, is the stock worth, is the company going to be more valuable tomorrow?
Andrew: I was talking to the founder of Carbonite recently and I asked him about how he has a similar philosophy. And I said, “How do you get there?” And he said, “Well, I sold the first company that gave me enough profit that I didn’t have to worry about the little things any more. And that let me focus on bigger ideas.” Is that what happened with you? How much of an impact did that first business have on your financial ability to do what you want and to call your own shots?
Kevin: One thing I always point out to entrepreneurs who tend to be a little bit possessive. Is that 100% of zero is zero. So, you’ve got to get over, what percent you own is meaningless. I always look for the biggest idea that I have at the time. So, at the time we did ICC, that was the biggest idea we had. It turned out to be, we did about $35 million in revenue, so it was good. But it definitely gave me the ability, gave me I guess what they call FU money. So, you can, there was enough money where I couldn’t retire but allowed me to take some risks, take some chances. At some point, after our company merged with another company and so on and so forth, I basically came down to FU and left and we started the company. So it gave us a lot of breathing room to take chances. I think what a lot of people run into, I always encourage people right out of college, this is the time you should get involved in a start up, you’ve got nothing to lose, nothing to lose. When you get married, have three kids, have a mortgage payment, two car payments, you’re pretty much screwed. I basically tell those guys, “Don’t do it. You’re going to destroy your life for this?” Because the probability is that it’s not going to happen. Which is one of the reasons my, when I took my book into the editor, when they were reading my book, they were like, “You’re a little negative, a little harsh on start ups.” Most folks are, “How do you get rich quick?” Doesn’t work that way, as you know. You’re an entrepreneur.
Andrew: It’s a lot more painful than people admit. You know what? Actually, as I’m saying this and you’re saying the pain, I’m realizing we’re not communicating that in this interview. It feels like, I see you, you’ve got a smile on your face, you’ve got an incredible track record. Take us through the pain. Make this more real than “get rich quick” fantasy that we’re telling people. What was some of the pain there as you built the business?
Kevin: You know, I’d actually say Double Click was easy, in the sense that there really was very little pain. I remember sitting and talking to Kevin Ryan. It was 2000. I said, “Kevin, I’ve never seen, startups are painful.” You know, my first startup, we couldn’t make payroll. We were always eating beans and burritos. I was making $6,000. I was sleeping on the floor of an apartment, no furniture, nothing in the refrigerator. Double Click is too easy. I don’t like it. Something bad is going to happen. Have we built a company that can withstand pain? Have we built a strong foundation? About three months later, talk about stuff hitting the fan. It might have been the privacy issues to the collapse of the dot com. 75% of our customers were out of business. The pain hit. Fortunately, we really had built a company that was resilient and we built it on a strong foundation.
Andrew: How did you sleep at night? What was it like for you during those tumultuous times? Now that we’re so far removed from it that you might be able to show vulnerabilities that you couldn’t have back then. What was going on?
Kevin: Well, for me as CEO and I’ve been pretty open about this. We were 2,500 person company, 25 countries. I was spending all my time dealing with politicians and lawyers. Everyone was class action this, class action that. Everyone was running to the internet companies because that’s where the money was. Just wasn’t having any fun. So, to me, that’s like, I always said, if I’m the best CEO for the job, I should stay CEO. Then I went to the board and said, “Ken Ryan’s going to be a better CEO in this kind of scenario where it’s less about product innovation and more about running a big public company.”
Andrew: That seems very analytical. What was the feeling internally? I usually like to give multiple choice questions out of some kind of crazy habit. I’ll just leave it to you. Describe, where was the pain there? What was going on?
Kevin: For me, it’s always been driven by passion. Almost an obsession. Maybe even borderline, who knows, borderline genetic disorder. I get totally obsessed with something. And I wasn’t obsessed. I wasn’t excited about going into the office. I can’t lead a company unless I’m totally fired up every single day. I’m the game. I mean, you have good days and bad days. But after a series of weeks and months, you’re like, the passion just isn’t there.
Andrew: But there wasn’t a moment where you were down on yourself or depressed or disconnected completely because you just felt empty. It doesn’t go from a ten to a zero, it goes from a ten to an eight. Is that right?
Kevin: I wouldn’t say an eight. I don’t know where it was. But to me, I was an eleven and it was a five or four. It wasn’t an eleven anymore.
Andrew: So, what is a five or four for you? If I’m pushing too deep, let me know. But the reason I’m asking is just, as we say, it’s really, really painful to be an entrepreneur but most entrepreneurs will only say that. When it comes times for us to say, “It’s painful because I was crying in the shower. Or it’s painful because I was so depressed, I was too afraid to go to work, and only went to work because I had to and no one knew how scared I was.” If we get to that, then the person who’s experiencing the pain will say, “I’m not the only one. I could fire up just like they did, just like Kevin did. Or just like Andrew described.” So what was that four like?
Kevin: Everyone always goes through cycles. Whether you’re having a good point in time in your life, and there’s lots of things that influence it, right. So, you are going to have bad days. You’re going to have bad moments, you can have bad weeks, you can even have a bad month. But when you realize that you’re having a bad month or bad two months, and it is because of the situation, that’s when it becomes tough. Because when you’re in a start up, I was fortunate at that point, I could walk away from it and still be involved with the company but not running it anymore. But it’s tough.
Andrew: Plus, you guys had, I think it was $900 million in the bank at the time. And I remember as everyone else was falling away, I don’t know who at Double Click, someone, I guess maybe more than one person said, ‘All these companies are all in a struggle. They’re all going to go away because they don’t have money. But we’ve got the money to withstand these difficult times and then we’ll be right back on top as soon as things clear up.’ And that was the feeling internally too at the time?
Kevin: I mean, yes and no. Jeff Epstein was a brilliant CFO. I even asked him, “Why are we raising money? We don’t really need it.” And he said, “Because we can. And you raise money when you can because you don’t know what’s going to happen tomorrow. And you want to have a big war chest when the inevitable comes, because it always comes.” So that was really smart. So we felt good that we had it. But when you have, I mean, I don’t know if you, were you around back in the 2000s? So you know what happened. It was a free fall. So, you didn’t know how far it was going to fall. Now, I’ve lived through a couple of recessions and so did the other guys. So we knew you’ve got to get yourself in a position where you can survive. You can’t go on losing $100 million a year and it may never come back. You’ve got to reposition quickly. And that’s one of the things that we did. We repositioned the company very quickly. And I always tell entrepreneurs, when a big economic catastrophe happens, you’ve got to overreact. You’ve got to overreact because your business is to stay in business. That is your only concern.
Andrew: Overreact by doing what?
Kevin: By reducing the size of the company. It always comes down to people. But you’ve got to do it. You cut your weaker people first. If it looks like it’s not just a little dip in the market because we had a couple of those dips. You remember back in ’99 was a correction and everything bounced back, everything was great. But when you have a long-term sustainable crash like we just had, really just coming out of now, you’ve got to adjust quickly. I always tell them, “Look, the bright thing, the bright part of this stuff is that the weak players, the people who didn’t react, the people that had marginal businesses, are going to be gone.” And my experience is that you always have way more profitable company, higher growth, better companies coming out of a recession. You’re competition is gone.
Andrew: Your competition’s gone. Your expenses are slashed and you’ve now prepared yourself to go.
Andrew: 2005 company went private. What was that like for you? How did your life change?
Kevin: Well, that’s why I was no longer connected to double Click, it didn’t change a whole lot. It was the right move. I think we made the right decision at that time. But the company really needed to be restructured and recapitalized and doing that in a public market’s pretty tough. So it was a good move. Now, Al Freidman turned around three years later and sold to Google for $3 billion. They looked like geniuses. But who knows. No one envisioned that our market was going to all of a sudden become one of these, a frenzy that you’ve got to have it. If you didn’t have it in your puzzle, your whole empire is going to collapse. It became their whole market. Obviously the guys from the second, third, fourth level companies, it all got scooped up. Because in a six month period, well about a two month period, six or seven companies got all scooped up for huge amounts.
Andrew: And when you hear about $3.1 million to Google, do you feel . . .
Andrew: $3.1 billion, did I say million?
Andrew: $3.1 billion. So how do you feel at that point? Do you say, “That should have been mine. I built, I took it so much further.”
Kevin: Yeah. So do I kick myself? Yeah, but what are you going to do? I made a free choice and there were lots of companies. I passed up investments on a bunch of companies that ultimately did well. I invested in companies that did crap, became tax write-offs. I don’t know. You can drive yourself crazy looking in the rearview mirror, so I just try to look forward. Make the best decisions at the time.
Andrew: All right. Let’s move forward. You start, after investing in companies, you go and you launch your own business with FindTheBest. Why launch a business this late in life and not when you’re just right of college? And not when you have to. What is it about this business that made you want to launch it?
Kevin: Well, I’m not sure what “have to” means. Right. Most of the guys you probably talk to on this program do it because they’re not doing it for the money, they’re just doing it because they love it. I can’t drive my, I get obsessed, when I get obsessed. I’ve got to do it. It’s always driven me in life. Whether it’s surfing, I got totally obsessed with surfing. I told Nancy my wife, “Something good always comes out of when I pursue my obsessions.” And so for this one, I kept coming across the same problem. Quite honestly, you only [??] hundreds of billions if not trillions of dollars has chased the Internet. It’s pretty hard to find something that hasn’t been done 20 times already. So I kept running into the same problem. It took me awhile to connect the dots that they were the same problem, which is I was looking for a ski resort, I was looking for a college. I was looking for a web hosting company. I kept running across these top 10 web hosting companies and their affiliate shills. I said, “My god, what has the Internet become?” A bunch of scammers and what can you trust? The certain thing is that you can find information on anything, right. You can find any information on ski resorts. But actually put them together and be able to compare. Who gets the most snowfall in the winter? Who gets the most skiable acres? Who’s got the most expert runs? Or for colleges or for dogs, all these different areas. It was just impossible to get there. I was spending all my time. I was, like, “Huh. This is a common problem across a thousand different niches.” There are competitors in each one of these markets. But they’re generally pretty small companies. They do a pretty marginal job. I was thinking if we could develop a platform and be able to use this across a thousand different niches, we could do it. It was a big bet.
Andrew: Why did you decide to go across all those different topics instead of zooming in on one, getting that really nailed down and then expanding slowly until you get the whole world categorized?
Kevin: I think that’s why we have a thousand different niches out there. I’m a technology guy. I felt that if we could develop this platform to go across a thousand different niches, it would be so incredibly powerful. The challenge was, could we actually develop this platform. If we would’ve pursued one niche, we would have built out that niche but we would not have created the platform. So what we did the first, I spent six months grabbing every government database I could and throwing it at it to see if we could represent it well. So that was a big bet. I knew the big gamble was, could we actually learn these markets better than or at least as well as these people that focus on the niches. And we discovered that we could take a researcher and in about a week’s time, master a market pretty quickly.
Andrew: How did you know that you mastered a market? What was a market that you mastered quickly? And how did you know that you mastered it?
Kevin: Well, we know we master it, almost every market we look at, ski resorts to colleges to dog breeds. You can take a look at what data is available out there. How are people searching for it? Google gives you all the intelligence you need in terms of what are the different attributes that people are most interested in relationship to a dog or a ski resort. And then, could we go out there and collect that information in an economical way. And we do. We don’t do any scraping. All of our data, not all of it but we bring in some public domain databases. But the vast majority of our data is actually human curated. Going to the source sites, whether a ski resort or company, often to buy the service and bringing the data into the system.
Andrew: I saw that. Smart phones, for example, had not just reviews from users like me as many sites have. But it was, I forget the title, but it was professional reviews or expert reviews. And there is so many smart phones listed in that. Does that mean that you have people internally who are all reviewing every single phone? How do you accumulate all that data?
Kevin: We do have people internally and externally that bring in manufactured data. The expert ratings that you’re referring to, we take a little bit of a more of a [??] critic or rotten tomatoes approach, which is you bring in a large number of different critics and you normalize their reviews and ratings to try to come up with a composite rating for the product. So that’s what we’re doing.
Andrew: Where do you get the ratings?
Kevin: Ratings come from, we either do our own internal rating system or they come from well known rating sources, probably a hundred different rating sources, whether it’s JDPower or CNet. There are tons of them out there.
Andrew: As you were talking early on in this interview, and as I research you, the word “smart” kept coming up. You said to the New York Times that you’re looking for smart people. And they put you on the spot, and they said, “Are you smart?” And you explained, “Smart in some things, not so smart in others. And what I’m looking for are people who can know where they’re really good.” Do you do this all the time, is what I’m getting at? Are you constantly evaluating people and saying, ‘Is this guy smart or not?’ Is that what you’re doing?
Kevin: Yeah, our interviews are tough. We lay it on the line from people. We’d rather have them walk out the door and not waste anyone’s time. We don’t want to waste their time. We don’t want to waste our time. We’re really brutal on people. Because we want, I’d say it’s like recruiting for the Navy SEALS. There is a certain caliber of person that wants to be put in that scenario, that wants to be challenged, that wants to be working with super smart people. They may not be the best. That they can learn from. A lot of people here are right out of college. And so they’ve taken on this interview style. And so we are looking. It’s tough to figure out if someone’s smart. So we take a look at how did they do in school. A big one is, can they solve logic questions.
Andrew: And so you give them logic questions?
Kevin: I’m sorry?
Andrew: So you give them logic questions in an interview?
Kevin: Yeah. I’ll give you a good example. This one, it kind of astounds me. It’s how much money is spent on haircuts every year in the United States. You only need to know three variables, population of the United States, approximate number of haircuts, and how much do they pay per haircut. Most people do not know, I shouldn’t say most, half of the people have no clue how many people live in the United States. Now we’ll take 200, 400, that’s fine. But when people say 10 billion, or people say 6 million. And when this 10 billion by the way, came from a Ph.D., person about to get their Ph.D. They just don’t, they’re either lacking in common sense or just intelligence. We need someone to be able to look at a solution and say, “That’s a reasonable solution. That could work.” If people think that there are more people in the U.S. than there are in the world, or 6 million people in the United States. It’s like, wow. And then we ask a bunch of other questions, somebody if they’re old, how many ping pongs can go in an airliner? People think the airplane is 4,000 feet long. They just don’t have any perception.
Andrew: That’s interesting. How about giving us one more? Without giving us away or thinking it through and we’ll leave it out for the audience to think about and then Google the answer. What’s another one that you ask?
Kevin: An easy one is you have eight ping pong balls and one weighs more than the other. And you have a scale. How many tries does it take for you to figure out which ping pong ball is the heavier one.
Andrew: [??] ping pong balls, one is heavier than the other, you have a scale.
Kevin: You have eight ping pong balls.
Andrew: Oh, eight, ah, okay.
Kevin: One is heavier than the others and you have a scale. The other one I also like to do is, you’re in a rowboat, the deepest part of the ocean, you throw a cannonball off, how long does it take to hit the bottom?
Andrew: All right. I’m leaving that out there. I can’t solve it right here. I can understand the pressure that you put people under. Now, do you do this in your life beyond this? Like, when you met your wife, did you put her through, not these kind of tests, but in your own way, a test to see if she’s smart enough for us to be married to each other?
Kevin: Well, there are other factors. My wife’s very smart. But there are other factors that go into it. But, yeah, I mean I’m not a judgmental person at all. Actually, I get along with people that, for example, I have pretty strong libertarian views on politics. But I can have discussions with socialists to hard right-wingers. I can have good conversations with people without, I’m not real judgmental in that way.
Andrew: I like your evaluation. Maybe not judgmental but evaluation. So for example, me, we’ve now spent 56 minutes together. Evaluate me as honestly as you wanted to be evaluated by your co-founder, and now I can’t find his name, Dwight. You wanted him to say to you, what was it? Jerk or something. Be open. so be open here, now that we’ve known each other for 56 more minutes and you can say whatever you want and then hang up a minute from now.
Kevin: So, evaluating you?
Andrew: Yes, I’d love to see Kevin O’Connor’s evaluation of me in this interview.
Kevin: Well, I find it interesting because I know you’re an entrepreneur.
Kevin: So, most entrepreneurs tend to be a little bit narcissistic, more interested in themselves and more centered around you. But you’ve chosen to do this and you ask very, very probing questions of other people.
Andrew: And what does that tell you then?
Kevin: That you’re on a complicated search for meaning of what you’re all about.
Andrew: Oh, what I’m all about. Interesting, okay. Nothing more aggressive than that? I thought maybe there’d be something fiery in there, no.
Kevin: Well, I don’t know you that well. But my guess is that you’re trying to figure something out. Of what is your meaning and role in life. I mean, we’re all, that’s a little . . .
Andrew: I see what you mean. Part of that is, could . . . I’m sorry, because of this internet connection, it feels like we’re stepping on each other as we’re talking. All right, fair enough. One last question about this process.
Kevin: Was it accurate?
Andrew: Yes. The goal is to talk to other entrepreneurs and figure out the same thing you pointed out early on, what are the patterns. Not what’s a great story that’s so memorable that it could move an audience of 1,000 people. But what are some interesting patterns that are actually applicable and are really used by real entrepreneurs, not the self-improvement guys who know how to sell you the stuff that you want to hear. With that in mind, sorry, you were going to say something.
Kevin: Well here’s a challenge to that. I remember reading a great book, “If You Meet the Buddha on the Road, Kill Him.” It was a great book. It was just about, basically, if you’re looking for the meaning of things in other people, you’re never going to find the meaning. It’s very much internal. I think a little bit of that is about entrepreneurism, is almost a disdain for what others think.
Andrew: I see. That if I’m looking for the pattern to success in other entrepreneur’s stories, I’m missing it. I need to do what my audience needs to do which is to look internally into our experiences.
Kevin: I’m being a little, I’m not sure if that’s not the case. I’m always reading. I’m reading everything from Andrew Carnegie, to Stalin to any, someone who’s had huge impact on the world and trying to figure out what it is. So, I mean, it’s still, it’s very valuable to learn. But at some point, you’ve got to say, “You know what? There is no answer.”
Andrew: Okay. So you read, or you know that Andrew Carnegie asked this guy Napoleon Hill to go and interview his friends, and then put together the learnings that he has from those conversations. I’m wondering, how can I do that today? How do I do it properly through these interviews? And I saw as I was saying it, there was either disgust or just non-familiarity.
Kevin: No, not at all. I ask the same questions, by the way. I do a lot of speaking in front of entrepreneurial classes at college. They’re all over the place now, trying to teach entrepreneurialism. I have a series of ten questions that I ask people. Because I am trying to figure out, is there, can you make an entrepreneur or is an entrepreneur born? Is it better to identify an entrepreneur and cultivate that? Or can you really teach it? So I can send you the list of questions. So it would be [??].
Andrew: Oh, in the interviews. To ask the entrepreneurs who I interview here some of the questions from your list?
Andrew: I would love that.
Kevin: I’m trying to get a Ph.D. student to do a study on it. If there was a sort of Meyers Briggs for entrepreneurs. Entrepreneur identifying, someone with more likelihood of being a successful entrepreneur.
Andrew: All right. So you’re saying, we ask some entrepreneurs who I interview here on Mixergy these questions. We get a sense of their answers and then based on that, we can find out what projects a Ph.D. student could put together around it?
Kevin: Yes. And I’m not even sure this can be done. But could you do a personality profile of people to figure out, is there something that separates the successful entrepreneur from the not successful entrepreneur.
Andrew: I want to know that too. But you know what? To me, I would say, let’s suppose, I would say the answer of whether anyone could do it or not is irrelevant. Everyone’s going to try. And a little tip here and there will make anybody better. I may not be born to be a writer, but if you tell me a little bit about the sentence structure and how to capture people’s attention with the first paragraph and how not to bury the lead, I’ll become a better writer.
Kevin: Absolutely. I use the example, I wanted to be an Olympic gold metal wrestler. I wanted to be in Olympic champion wrestling. And I got totally obsessed with wrestling. And I realized, there are people that are gifted. I did not have the genetic structure to be an Olympic wrestler. Without question, people who are Olympic wrestlers put in a lot of hard work. There also born with just a . . .
Kevin: And I think that entrepreneurism, absolutely. You can swing somebody, 10%, 15%. Do you have kids?
Kevin: Okay. I use the same thing with kids. We influence, we think, your kids are, they’re born a certain way and you can kind of influence them. But it’s tough, you can’t remake them.
Andrew: Yeah, I see what you’re saying.
Kevin: But you’ve done it.
Andrew: I have. And I know that there are little things that I learned from reading stories about Ted Turner for example that I would use in my life. When I used to read about Steve Case sitting down at . . . you know what? I’ll use Ted Turner, the example that I often use. Ted Turner would walk into an office of someone he wanted to do business with and start kissing the guy’s feet and saying, “What do I need to do to win your business? I will kiss your feet. I will be your whatever, your slave.” When I hear those stories, it’s not like I’m going to become Ted Turner afterwards. But it opens my mind up to the idea that I can push a little bit further. I can go and be a little outrageous in business and still be okay. It’s okay to just barge into someone’s office if you can do it with some kind of charm. That’s useful to learn. It’s useful to apply.
Andrew: It’s applicable. That’s what I’m looking for in these interviews. I know your story here today is going to stick in someone’s mind in the audience. And they’re going to say, “You know what, I could do this. I could do it the way that Kevin O’Connor talked about. I don’t know exactly how.”
Kevin: I’d rephrase it a little differently. You have to take your core, who you are and you’ve got to tweak it by some of these learnings.
Kevin: It’s got to be you. I think what you’ll find in all the commonalities. That’s probably is what, it probably wasn’t a trick that Ted Turner did. It’s probably who he is. You can always tell the guys. Have you done Dale Carnegie class?
Andrew: I used to assist teaching it, yes.
Kevin: There you go. I can always tell when someone’s done Dale Carnegie. And Dale Carnegie you remember, 90% of the people who went to those classes, it was really for psychological issues and not really to learn better.
Andrew: Or because they’re bosses often sent them.
Kevin: Yeah, but Nietzsche wrote a book of all the horrible stories people tell in speeches. Wow, dude.
Andrew: You took the session too.
Kevin: [inaudible] Keep it in the closet.
Andrew: You took Dale Carnegie too. Am I getting that?
Kevin: Yeah, my wife and I. It was good.
Andrew: How long ago?
Kevin: 25, 20 years ago. It was good.
Andrew: Yeah, the program is great. The program is great, the book is great. It changed me a lot.
Kevin: I learned a lot. My favorite one with Dale Carnegie is about people rationalize anything. I don’t even bother. People can rationalize murder. They can rationalize stealing from the company.
Kevin: They rationalize away anything. So, it’s futile to try to convince somebody they did wrong.
Andrew: Yeah. It starts off with the story of someone who killed, with the murderer who is still rationalizing it away. And you’re right. Never tell a person he’s wrong. That’s one of the key lessons from that book.
Kevin: But you can also tell, you know how the sweetest sound is a person’s own name. So you can always tell, like I know this one guy, “Well, Kevin, Kevin, Kevin . . .”
Andrew: Did you catch that, that I did that with you at the beginning of the interview?
Kevin: I didn’t.
Andrew: It wasn’t intentional but it just comes out, you know. You spend some time with them and you learn.
Kevin: But you don’t overdo it.
Andrew: Yeah, it’s not like I’m sitting down here and on my sheet I say, “Make sure to say Kevin’s name three times, and then he’ll love you.”
Andrew: Final question. Behind you, I see there’s something up on a screen being projected. Am I right?
Kevin: You know what? No, it’s a, I just saw that. It’s cars driving by, it’s flashing, the sun, sunny day down here.
Andrew: Okay. All right. I was going to say, what kind of funky southern California office do they have projecting all kinds of stuff on the wall behind them. But that’s not, it’s the sun.
Kevin: The sun.
Andrew: Kevin O’Connor, thank you for doing the interview with me. And I hope everyone checks out FindTheBest.com where maybe there’ll be a list of the best entrepreneurs and you guys can help categorize it or confirm whether it’s true or not. Kevin, thank you so much for doing the interview.
Kevin: Thanks. It was fun, appreciate it.
Andrew: Thank you for watching. Bye
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