Leigh was born & raised in Bellevue, WA, and both of her parents worked in public education as teachers. She grew up feeling different than other kids because they displayed much more wealth than she saw at home and that proved to be a driving force to advance her career. There is one thing that Leigh expressed in her childhood that she has never changed: A disinterest in conforming to the social norms of dress codes. Leigh attended the University of Washington, got her degree in Psychology, and ended up working for the Seattle Mariners as the Director of Public Affairs. There, she would be given the task of handling Senator Maria Cantwell's tickets. Several years after an initial meeting with the Senator, Leigh received a call asking if she was interested in helping campaign. Consistent with her strong tenet of being opportunistic and always saying "yes," she went on to help the senator win.
She then went on to serve a variety of other roles including Chief Marketing Officer for Avvo: a marketplace that connects lawyers with clients, and discusses a key failure during the interview. Leigh currently serves as the CEO of Whitepages, a data company that helps you uncover information about people such as background checks. Whitepages is trusted by over 35 million users!
00:00:00 Leigh McMillan: We had invested a lot of time into medical; a lot of energy into it. This isn’t unique to Avvo. This happens at companies, particularly start-ups all over the place, but it just didn’t work. It was a fail.
00:00:19 Ash Faraj: Hey! Welcome to the ExecuTalks Podcast. It’s the show that gives you insight to the personal stories of today’s top executives. In this episode, you will hear from Leigh McMillan, current CEO of Whitepages, a data company that helps you uncover information about people. Whitepages is trusted by over 35 million people every month. You want to stick around until the end to hear some key learning lessons that Leigh shares and how she approaches leadership.
00:00:52 Ash Faraj: Leigh was born and raised in the suburbs of Bellevue, and both of her parents worked in public education as teachers. She shares how she felt that her peers growing up had significantly more wealth than she’d grew up with. Although she felt different growing up, she never felt pressured to conform. That is something she’s held on to throughout her entire life.
00:01:13 Leigh McMillan: Well, I grew up in Bellevue. I’m one of those few apparently local people. Grew up in the suburb. Both of my parents were teachers. My father was a counselor for a while, a school counselor, and also taught woodshop back in the day. My parents both worked, and so I walked to school in the morning by myself. I came home. Was home for a few hours by myself where I would -- and I’m not sure if my parents even know this, I would -- turn up the stereo really, really loud [laughter] and play music loud and kind of dance around the house until they got home. We had a couple of hours, my brother and I -- I have an older brother -- where our parents weren’t around. We’re pretty self-sufficient and self-starters. We would get ourselves to soccer practice and do things like that. There were kids that I went to school with that were very affluent. I think that had an impact on me. I remember I came from school -- and I don’t remember how old I was, but in elementary school -- and came home and asked my mom if we were poor, which we were not. But comparatively there were kids that I went to school with they had wealth and means and things I saw. I think that influenced me when I was younger to -- I don’t quite call it peer pressure, but to -- do things in order to advance my career or advance my place. I always felt maybe a little bit of pressure or motivation around that. I’m not sure it’s legitimate or even should be a thing, but it was when I was a kid.
00:02:56 Male Voice 1: Did you feel pressure to fit in with the other kids?
00:03:01 Leigh McMillan: Yeah, I did. I did to a certain extent, but I picked ways to stand out as well. I didn’t feel like I had to conform, but I was always looking for ways to kind of be a part of that. It did influence me as I went to college and I was thinking about what career I would go into. Again, rightly or wrongly, I think that did have an influence on me. I didn’t feel peer pressure to fit in with the trends of the time, what kids were wearing, and I still do this today. I’m wearing all black.
00:03:41 Male Voice 1: You’re matching us though. [laughter]
00:03:43 Leigh McMillan: Exactly. So, you know, I would always kind of find my thing that would be slightly different, whether it was something I was wearing, trying to be entertaining, or sense of humor, and things like that. I think that served me well as I grew up. I haven’t felt pressure to conform, and I actually think it’s better to find your own way.
00:04:11 Ash Faraj: Leigh attended the University of Washington and got her degree in Psychology. She attributes a lot of her success to being opportunistic. After she graduated, she took the first opportunity that came to her.
00:04:25 Leigh McMillan: I started off at the University of Washington as an art major. My father was pretty creative, so he taught woodshop. He could build furniture, so he always had a really creative bent. I always thought that was something that we had in common and that I tried to tap into, but then at the same time I also realized how do you turn art into a career? Now, graphic design is a much bigger thing than it was back in that time. It dawned on me, and I think also due to some influence from my parents, that maybe that wasn’t going to be the thing. And then at the end of the day, I really wasn’t that good. [laughter] I kind of realized that, and then I went into the next career opportunity and that’s psychology. I actually have a degree in psychology.
00:05:16 Male Voice 1: She’s reading us right now. [laughter]
00:05:17 Leigh McMillan: [laughter] Gosh, can’t make money in art, you know, be a psychology major and don’t go into psychology.
00:05:26 Ash Faraj: Leigh, can you share real quick. How did the opportunity of the Seattle Mariners job come up?
00:05:31 Leigh McMillan: I actually worked at the Seattle Mariners twice. I worked there right after college. It was a friend of mine from college, a sorority sister of mine, actually. Had a job there, and was like, “Hey, they have an opening.” Come do this and I did. I think it’s kind of the very first example of one of my career philosophies and that is to just say ‘yes’ and go dive into something, whether you know how to do it or not. A combination of that and meeting amazing people and just being the right place the right time. That was definitely an example of that. I worked for a number of years with the Mariners. I worked the ticket-related stuff and then ultimately, as we were trying to figure out what to do with the Kingdome and wanting a new ballpark, I ended up running Public Affairs for that.
00:06:23 Male Voice 1: Real quick. You attribute a lot of your success to being optimistic. What’s the fine line between getting a lot of opportunities and knowing which one to go with? Each decision will lead to a different path. What was your thought process like when you’ve got an opportunity?
00:06:43 Leigh McMillan: It’s a great question because I didn’t always choose right. I think that’s the trade-off with always saying ‘yes’, sometimes you will get it wrong. At least that’s how I like to think of it. As opposed to I just didn’t think through something thoroughly [laughter] which is probably a combination of the two. There are a couple of jobs that I took throughout my career early, and also more recently -- not super recent -- but later on in my career where it just wasn’t the right choice. But I would take that trade-off all day long to be able to do what I’ve been able to do. I worked in major league baseball. I worked in politics. I worked in the video game industry. I worked in mobility services, so all of the car sharing. I’ve gotten to work in all of these different, really unique, and desirable industries. The couple of decisions that I made badly was a very small price to pay to be able to do those things.
00:07:48 Ash Faraj: Early on in her career, Leigh was working as the Director of Public Affairs for the Seattle Mariners. The owner of the team at the time was good friends with Senator Maria Cantwell, and she was a huge baseball fan. Leigh was given the responsibility of making arrangements for the Senator to make it out to a few games. Several years later, she got a call from Senator Maria Cantwell asking if she was interested in helping her campaign.
00:08:13 Ash Faraj: Where does the story of Senator Maria Cantwell start? Where does that story start?
00:08:18 Male Voice 1: I’m curious to hear that too.
00:08:19 Leigh McMillan: When I worked at the Seattle Mariners, this was back at an early ownership group, Jeff Smulyan, back when he owned the team. He was from Maria Cantwell’s home state, so they knew each other. She is a huge baseball fan, so he asked me to take care of her tickets and help her out and get her some tickets to spring training. At the time, I had no idea who she was, and she actually was in the State Legislature at the time. I called her office and asked them to send me some information about her, because I just didn’t --
00:08:52 Male Voice 1: -- had no idea.
00:08:52 Leigh McMillan: -- had no idea whatsoever. They ended up sending me a packet of press clippings. It was like this thick. I read through that and was really, really impressed with what she had done, even just being a State Legislator. She was early on one of the drivers of the Growth Management Act, which helps guide how cities grow and manage their growth and things like that. I just was impressed with what she had accomplished. As the years progressed, we just got to know each other better. At a time when she went into technology, then I actually followed her and that’s how I ended up with a career in technology. I went to RealNetworks when she went there, very early on. Because of a chance meeting with her, I got to work in politics in a way that I think would be hard for you to break into and then also got to move into tech.
00:09:55 Ash Faraj: What do you think some keys were to developing that relationship? Obviously. you got closer over the years, but what are some things that you did to flourish that relationship?
00:10:06 Leigh McMillan: I worked my butt off. [laughter] That’s the thing; when you get an opportunity like this around people who clearly are successful in their field, are doing good things, whether it’s in an industry or for the general public or doing something creative, the trade-off for that opportunity is that you have to work incredibly hard. Particularly since I didn’t have experience in either politics or technology, I worked a lot of hours. Did my homework and talked to a lot of people to learn about what’s the right thing to do, what’s not, you know.
00:10:50 Male Voice 1: Just curious, what were some mistakes that you made that were painful at that time?
00:10:57 Leigh McMillan: Oh gosh! Going on trips where we’d go to other states and do some fundraising events with some of the senator’s colleagues. You think you know the driving directions to get somewhere and you think you’re super prepared, but back in the day when you didn’t have a phone to tell you how to get somewhere, and you’re printing out MapQuests, and if you didn’t get it exactly right, you’re stuck in a car and you’re lost with a senator that wants to, you know, time is precious! You know, things like that. You get the background of a company that we’re going to see. You missed some of the subtleties about what that company does and produce and what their challenges are. You think you got it, but you just didn’t ask quite the right questions. There are examples of that where, despite all of that effort that you could possibly do, something goes sideways and then you just got to figure out how to deal with it.
00:11:55 Ash Faraj: Didn’t’ you work for the Senator on one of her campaigns?
00:11:58 Leigh McMillan: Yeah, I was the Finance Director on one of her Senate campaigns, her very early on Senate campaign, which means you raised the money. That was something I had done for her at a much smaller scale earlier on in her career, and so when she decided to run for Senate, I think she decided a little bit late to get in the race, there was some catch up we had to do. She gave me a call, and when you get a call like that you generally say yes. I did and fortunately it worked out. She’s in the Senate and continues to serve the state today.
00:12:36 Male Voice 1: Why do you think it was you she called?
00:12:38 Leigh McMillan: You’d have to ask her. [laughter] Maybe she was tired that day or, you know, had a hard day. I don’t know. I think I do this today; there are people that I’ve worked in the past that I trust that I know work well with me. All other mistakes aside but are a good counterbalance to me. I’ve had some folks that I’ve worked with here at Whitepages that I’d worked with at previous companies. When you work with a number of different people, you kind of get a sense of what it’s like to work with them and think they’d be excited about the opportunity and are going to come in and work hard. You give them the call, so I do that today.
00:13:37 Ash Faraj: After several years, Leigh got invited to take on the role of Chief Marketing Officer at Avvo, a platform that connects lawyers with clients. There she would accelerate the company’s growth and Avvo would end up being acquired after just five years. There was a key failure at Avvo that she shares.
00:13:58 Leigh McMillan: Avvo was really unique in that it was unique for me too. It was a legal marketplace. You had to build up a consumer side of the business and the attorney side of the business at the same time and get what Bill Gurley calls a flywheel going. How do you create demand and supply at the same time? It was a really interesting challenge just from that perspective, but then also working with lawyers.
00:14:31 Male Voice 1: That must have been tough.
00:14:32 Leigh McMillan: Really, it was fascinating. It was absolutely fascinating to me. So to build up both those sides of the business was I think any marketer’s dream challenge to do. Fortunately, when I had joined the company it had a couple of years to kind of figure it out and get things in place. So really my job was to just try and drive scale, which I love to do. The opportunity to work with lawyers across the country with so many different personalities and figure out how to do that. It was a lot of fun. It was a great experience. Great leadership at the company.
00:15:13 Ash Faraj: Can you take us through some of the growing pains in those five years? Maybe a couple of low points, just really like tough intense growing pains?
00:15:25 Leigh McMillan: Yeah, there was. Avvo was started off really focused on lawyers. But then as we got more and more successful with lawyers, it’s like, gosh, we have the infrastructure in place for this marketplace. Let’s do the same thing with medical and with doctors. We’ve got this figured out. Let’s go do it with doctors. As it turns out, doctors don’t think the same way as lawyers. The marketplace doesn’t operate the same way. Instead of having patients pay doctors directly there’s insurance companies involved. So it’s a much more complicated marketplace, and you throw in dentists. Dentists operate different than other doctors. Plastic surgeons operate different. It was a much more complex marketplace than I think we had realized at the time. We had invested a lot of time into medical; a lot of energy into it. This isn’t unique to Avvo. This happens at companies, particularly start-ups all over the place, but it just didn’t work. It was a fail.
00:16:28 Ash Faraj: How long did it take you to realize that it was a fail?
00:16:30 Leigh McMillan: The good news is, and it’s the lesson that you get, fail fast. While it didn’t feel like it was fast at the time, looking back, we didn’t spend an inordinate amount of time. We probably spent the appropriate amount of time to determine we could be number 300 in medical, or we could be number 1 in legal. Let’s be number 1 in legal. I credit Mark Burton and the leadership there at the company to make that determination, but it was tough. It was tough. We were feeling the success around legal and it just didn’t translate into health in the way that we thought it would. So that was a painful period, but that’s part of: you go in, you try it, you learn it, fail fast, move on, take the learnings with you.
00:17:21 Ash Faraj: If you had to pick two key lessons you learned during your time at Avvo, the five and a half years you worked there, what are two key lessons or takeaways you took from your experience there?
00:17:31 Leigh McMillan: I think this is not unique to Avvo, but definitely it plays itself out there; I’m a believer in changing up the guard. Meaning, whether it’s yourself, you’ve been doing something for a few years, you kind of mastered it, but the company is evolving and growing and maybe needs a different skill set now. I try and think about this too as we’re building out and growing here again at Whitepages. Maybe it makes sense to move someone from this role over to this role, both for their career advancement but also because bringing new thinking into roles can sometimes help. Just as the company’s needs change, bringing in some fresh perspective and also helping people grow their careers by creating opportunities for them to go take on something else that they hadn’t really thought of. So at Avvo we did; we moved people around, enabled people to take on different roles that they wouldn’t have originally thought for themselves, but their fresh ideas, their fresh perspective, helped move the company and also helped their careers. My career has been built on doing that. While I was at RealNetworks, I probably had twenty different jobs while I was with the company. That enabled me to figure out what I’m good at, what I like, what I don’t like, and it really helped me shape the rest of my career. I learned a lot about what I wasn’t good at. [laughter] So I try and bring that here. Avvo was the same way. As we grow and create opportunities for people, let’s not be afraid to change the guard around a little bit. That’s a pledge for me as well. There’ve been times where I was like, “You know what? I think your company would benefit from somebody else doing the job that I’m in,” and I think that’s an okay thing.
00:19:33 Male Voice 1: What’s your approach to leadership and how do you coach versus teach?
00:19:37 Ash Faraj: Oh, good question.
00:19:38 Leigh McMillan: That’s a really good question. My approach is I’m still learning every day. Just trying to do better today than I did yesterday, [laughter] and try and learn from past mistakes. You take these personality tests and they give you insight into your personality, some better than others, but pretty much across the board I’d be considered a driver. I try and leverage that. But have it manifest itself in a way where, instead of being a driver and pushing, I try and be excited about opportunities and have that catch on. Then also a sense of humor I think is pretty important. Work hard, have fun, laugh a lot. One thing that I would say is I’m not afraid to laugh at myself or acknowledge when I’ve made a bad mistake, or mistake, or I’ve been otherwise just done something stupid. I think by doing that [laughter] it gives other people the freedom to take the chance and mess something up.
00:20:59 Male Voice 1: We want to wrap this up with “Finish the Sentence” Game. The first one is: in my opinion the most important life skill is…?
00:21:11 Leigh McMillan: Listening
00:21:12 Male Voice 1: The second one. The one thing I dislike about my job is…?
00:21:17 Leigh McMillan: Oh gosh! I guess I should be honest. Budgeting.
00:21:22 Male Voice 1: The third one. One quality I think every leader needs to have to be successful…?
00:21:27 Leigh McMillan: Humility.
00:21:28 Male Voice 1: When I’m considering partnering with another person or business, some dealbreakers for me are…?
00:21:35 Leigh McMillan: At the end of the day, while business is important it’s not massively, massively high stakes. Nobody is going to die tomorrow in the tech space that I work in. You have to be able to not take things too seriously.
00:21:51 Ash Faraj: Interesting.
00:21:53 Male Voice 1: The fifth and final one. The worst advice I’ve ever received is…? It can be personal or professional.
00:22:01 Leigh McMillan: Frankly, dressing for first impression. A little bit of, you know, you need to fit in. This is what the expectation is of how you’ll dress, whether that’s a suit or this or that. The other thing, hair needs to look this way, whatever. I just haven’t paid a lot of attention to that, and the times that I have I didn’t perform as well. You got to feel comfortable in your own skin in whatever way that is. So, I guess it’s a more meaningful way of saying that is to be your own self.
00:22:40 Ash Faraj: Thank you for tuning into this episode. If you enjoyed listening, please subscribe on Spotify or Apple Podcasts. Please leave a review so we that we can better serve you. Take care, dream big, and we’ll see you next Monday.