Q&A: Former Apple exec Andy Miller on Steve Jobs, becoming a VC, and owning a minor-league baseball team

Andy Miller left Apple this past summer to become a General Partner at Highland Capital Partners, a venture capital firm. At Apple, he was the company’s VP of Advertising, reporting directly to Steve Jobs. (Apple bought his mobile advertising company, Quattro Wireless, almost two years ago, and Miller helped launch Apple’s iAd product.)

Today, Miller’s day job has him focusing on technology investments for HCP, based in the Bay Area. He’s also an owner of the Modesto Nuts minor-league baseball team. And he’s finally using his Twitter account, where you can follow him at @AndyMillerHPC.

I recently caught up with Andy. Here is a lightly edited transcript of our conversation.

SplatF: The big story, of course, is Steve Jobs’ death. Do you have any thoughts on Steve?

Andy Miller: I was super fortunate to have spent any quality time with him over the last couple of years. My Tuesday meetings were unbelievably stressful but unbelievably rewarding. And between buying the company and moving my family out here and changing the way I look at everything, there’s probably nobody who had a greater impact on my life, even though we only spent a day a week together.

After a big hit like Quattro, and having spent time at Apple, I assume your options were wide-open. Why did you go into startup investing?

I got asked to interview for a really big job in Chicago. When I was talking with the group about the opportunity, it was hard to believe that they were interested in me. [Laughs.] So it made me think, wow, there’s an opportunity to run something really significant and exciting and sort of what I’d always thought I wanted to do.

And I sat down with my wife to talk about it, and we both pretty quickly came to the decision that we just moved out here from Boston, and we love it out here, and that there’s a lot to do here, and we wanted to stay. And the idea of being the front-and-center guy in a big company was not what we wanted to do at this stage in our life.

That made the rest of it pretty easy, because I didn’t want to start something else up from scratch. And I love the guys at Highland Capital. They’ve been my VCs at Quattro and mentors and sounding boards for a long time. And this was always an opportunity for me, if I was ever interested in it. So I started to explore it more and got really excited about investing and looking at companies out here.

I’ve been an angel investor and have loved that experience. So I get that company-building aspect of things over again. And I’m also helping Highland build their brand out here on the West Coast. They’ve been a phenomenal East Coast firm forever, and have made a real effort, and have really strong results already here on the West Coast.

What do you — Andy Miller — bring to the table, besides a check? What did you learn at Apple that you’ll be able to bring to a startup?

It’s really important to have a good firm, but it’s more important to have a great board member. It’s kind of a cliché, but it matters the most during your Series A and the early stages of your business. You’ve gotta have someone who’s going to help you build a business and take a look at it critically. And the fact that he knows, you know, Johnny and Jimmy and Joey, the corp. dev guys at these other companies, really doesn’t matter, because you’re not ready for that yet — you don’t have a business to present.

So, someone who will sit down and work with you, sort of the way Steve and I sat down with the other executives at Apple to take a look at: Okay, what is iAd going to be? How are we going to position this? What’s the visual? What’s the pricing? How are we going to market it? How do we make this simple and understandable in the Apple way? …Is the same kind of approach I want to help take to our startups here, the ones I invest in and the other ones that Highland has already invested in.

What kinds of investments will you be looking at?

It’s pretty broad. I am digital, generally. Mobile, consumer-facing Internet generally. Probably, if I had to stack it up, I’d say mobile has been the smallest part so far. Maybe I know too much or I’m too cynical. [Laughs.] I kind of have beginner’s mind on the other stuff. But there’s just no shortage of ideas out here.

But what I’ve really been blown away with is the quality of the teams. I’m not sure if that’s a Highland thing — being a top-tier firm, that we’re seeing really high-quality entrepreneurs — but just really impressive, well-formed teams that you can’t help but lean forward and listen to what they want to talk about. And I think that’s unique to the area.

Would you invest in a mobile advertising startup?

Let’s say “not right away.” Right now, I think that mobile advertising actually has a long way to go and there’s a lot of interesting companies to be built with it. It’s a little too close to what I just did, so I kind of want to separate myself a little bit from it.

I’d definitely look at ad tech as well as an investment, but I think that’s a little harder to make versus some of the other things that are out there. I’m really interested in the platform plays. We would like to do a consumer-facing Internet play here that we think can grow into a real big business. There’s just a lot, and whatever we decide on here will also be mobile. It’s hard to divorce the two.

Apple’s iOS and Google Android have run away with the smartphone platform story, but someone is probably going to be number three. Are you interested at all in some of the others, such as RIM’s BlackBerry or Microsoft’s Windows Phone?

As an investor, no. There’s no critical mass, it’s going to take a long time, I don’t think I’d want to invest in a company who says, “hey, you know, we’re concentrating on the RIM platform, or just Windows.” I think the Windows platform is interesting now, personally, but the share of voice and development ease and the best use of invested dollars is definitely on iOS and Android.

You’ve also invested in a baseball team. Tell me about that.

I have! I’m a big baseball fan. I bought into the Modesto Nuts, who are the Colorado Rockies’ Advanced Single-A team in Modesto, California. And it’s a total blast. Everything I had dreamed about. I love going to the games, and the team is fantastic. The quality of the player in Advanced Single-A is as good as it gets — you know, they’re number one draft picks, and the folks who they’ve given signing bonuses to. And pretty much everybody has a shot at being a Major Leaguer at some point. So it’s incredibly well-played baseball.

How’s that business?

It’s the movie theater business. The Rockies own the players, they draft the players and pay the players. We own the stadium, the concessions, the apparel, the promotions, the marketing, the advertising, and we house the players and drive them around. Basically.

Everything in between the white lines is theirs, which is great, but you have to realize you have some superstar stud first baseman, who’s ripping the league up and everyone’s coming to see him, and then in July the parent club calls him up to Double-A or Triple-A and that’s, you know, a big hole in your team.

But we made the playoffs this year, we won the second-half title, and lost in the playoffs, but it was a lot of fun. The City of Modesto really supports our team. We set an attendance record for the second year in a row, and we were named California League Franchise of the Year.

Thanks again to Andy for his time. And remember, you can now follow him on Twitter at @AndyMillerHCP.

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