Frank Addante fits the textbook definition of a serial entrepreneur. Since dropping out of college his junior year to create a search engine during the early days of the Web, he’s been with one startup after another. Since the late ’90s, these companies have almost entirely been in Los Angeles, making Addante one of the forbearers of today’s active L.A. tech scene. His current company, which also happens to be the one he’s been with the longest, is ad tech firm Rubicon Project. Although that sector is infamous for its esoteric construct of intermediary companies, Addante’s pitch for Rubicon is simple: make the process of buying an ad as simple as buying a plane ticket. He launched Rubicon in 2007 and has turned it into a firm with $292 million in revenue in 2012. It’s commonly expected to be the next L.A. tech company to go public, which would be a snow leopard-rare occurrence in today’s economy. Addante recently sat down with the Business Journal to talk about the companies he’s already taken public as well as growing up in Chicago, and the perils of being ahead of your time in tech.

Question: You’ve been part of L.A. tech for a while, but didn’t grow up here, right?

Answer: I’m from Norridge, near Chicago. It’s the only city that’s completely surrounded by another city. It’s right next to O’Hare, so the city of Chicago annexed all the land around the airport and my town was basically surrounded by Chicago.

What kind of a town was it?

Very small. My eighth-grade graduating class was 44 people and my high school was less than 400. There were a lot of Italians. Some didn’t even speak English. My dad was born in Italy and my mom was born in Poland, so they were immigrants as well.

What was it like growing up with two European, strongly Catholic cultures?

My wife and I got married last June and just from aunts and uncles, the first cousins – I have to say first cousins because especially for Italians you’ve got tons and tons of seconds and third cousins – but just from first cousins, we had 93 people.

A small working-class town is very different from Los Angeles.

Very few people went to college, many are in construction. Those that went to college went to community college versus universities. I’m guessing there were less than 10 that went to the university. It’s very blue collar.

So did you go to college?

Yeah. But I dropped out. I went to Illinois Institute of Technology. It’s one of the top two electrical engineering schools. Right up there with MIT.

Were you a good student?

No. I had a hard time studying. My senior year of high school for half the year I didn’t go to traditional class. I had an office at the school. I was working with the Illinois State Board of Education on vocational education. Our school had two organizations, DECA (an organization that promotes marketing and entrepreneurship) and Future Business Leaders of America. I was involved in both. I ran for state president and won, and for FBLA I was the second runner-up in the state for Mr. Future Business Leader. I lost because I wore a purple shirt. I got point deductions for wearing a purple shirt.

They just thought that wasn’t serious enough for a future business leader?

Had I not worn that purple shirt, I would have won.

Were there other hobbies growing up?

I played a lot of basketball. I played all four years in high school and was on varsity from my sophomore year on. I was a shooting guard and small forward.

Do you still play?

No. I injured my ankle when I was in high school. It was one of those things where a doctor told me to go get therapy and I said, “I’ll worry about it when I’m older.” Well, now I’m older. It’s been unstable, but I’ve been putting off surgery.

How did your parents feel about you going to college?

Neither of them went to college. My mom was a stay-at-home mom and my dad has had a series of jobs. He worked for Brach’s Candy for a while until Brach’s started letting people go. He’s had a series of manufacturing jobs since. He drives a forklift now.

Do they get what you do?

No. They’re very, very simple people. My mom doesn’t drive on the highway; they’ve been on a plane maybe five times in their entire lives.

So it was a big deal for you to get to college. They didn’t have a fund or anything?

I got a number of scholarships, student aid, loans; I worked three jobs when I was in college. It was $35,000 a year; probably not the smartest choice for me.

How did your parents feel about you dropping out in your junior year?

They didn’t know. The thought of going to a university was too far-out.

What led to your dropping out?

I started a company. It’s cliché, though it

wasn’t in my dorm room but my frat room. It was a search engine directory called Starting Point. It was one of the top 10 websites on the Internet back in ’97, ’98.

How did you begin to develop this thing?

Well, to make money in school for books and food I was doing contract work setting up computer networks for companies. I found that I was starting these servers and connections for people, building websites. But how do you know how to find them? How do you know how to find, say, a travel site? Starting Point was a search engine and directory, we’d organize sites such as the top 100 sports sites and travel sites.

So it was very human-sourced.

It was building like a card catalog for the Internet.

Were you always electronically minded?

I thought I was going to be an electrical engineer, but as part of engineering I had to take computer science classes and I didn’t get it at all. When I started Starting Point I went to the bookstore and I bought a book called “Learn PEARL in 21 Days” and I stayed up all night reading this book about coding. The next day I started coding and it all made sense. It was funny – I spent $100,000 on college and this $20 book was the most valuable book.

How did you fund the company?

Initially it was me doing odd jobs to fund it, then I needed a more sustainable way to make money and I thought of advertising. It wasn’t a normal thing to advertise online then. I cold-called Ameritech, a local phone company. I said, “There’s a ton of traffic here, would you be interested in sponsoring the home page?” They said, “How much is it?” I said, “$5,000.” They said, “OK.” I thought that was way too easy. So I called the next one, ATT, and they said, “How much?” and I said, “$10,000” and kept doing that until someone said, “How do I know there’s really that many users?” That turned out to be the genesis of the next company.

What happened to Starting Point?

It was acquired by CMGI, a huge Internet conglomerate, in 1999. They crashed in the dot-com bust.

How much did you get acquired for?

It was part of another transaction for a company called WebPromote, which turned into YesMail. The combined company was purchased for $450 million.

Did you have a good equity stake?

I did. It was a decent amount of money but it was all CMGI stock. It turned out to be a big goose egg.

But you had something that was worth a lot for some time?

Yeah, but I never paid attention to it. I should have. I didn’t really know what it all meant. I was 21. They’d want to take business meetings and want to meet at a bar and I couldn’t go.

What was next?

I was already on to the next thing, called Reactions. It was how to track and target a campaign. Then Reactions ended up merging with another company in L.A. that became L90. We took it public and it was acquired by DoubleClick. So then I started a mobile company.

What did that do?

It was mobile ads. The thought was your mobile phone is the only personally identifiable piece of info that you really have that’s digital. We could use the mobile device to do unique things with ads, like if you walked by a Starbucks you could get a coupon and use your phone even to pay.

What was the market response?

There wasn’t one (laughs). We just started too early. We had one customer and partner and that was Intel. Then I raised venture capital for it. It took me six months and I wasn’t paying attention to what was happening with the business and the market. I called up the investor and said I’m going to give you your money back. The world was imploding and no one was thinking about mobile ads. I was like, “I could either waste your money or give it to you.”

And from there?

I started an incubator called Addante LLC, which became Strongmail, a system for email infrastructure. We built a hard-core email infrastructure for companies like Charles Schwab to send secure statements or American Airlines to send flight notifications. I self-funded and we were profitable when it started taking off. Then I ran it as CEO and raised money from Sequoia Capital and moved it up to Silicon Valley. I spent two years there.

How big did the company get?

It’s still around. It’s now the leading provider of email infrastructure.

Are you still on the board?

No. When I started Rubicon I dropped off of all boards.

What’s the goal with Rubicon?

To automate the buying and selling of advertising. To make it as easy as it is to book a flight. Look at what buying stuff was like before Amazon. You had to go to all these individual stores and if it wasn’t in stock, sorry. You just go to Amazon now.

Will ads be able to support all these free online services?

It already does. The digital ad market is a $50 billion market. And it didn’t exist 15 years ago. Name any other market that’s gone from zero to $50 billion in 15 years. It’s insane.

Is Rubicon the longest you’ve been with any one company?

In an operating role. We just had our sixth birthday. I think we’ve made at least 12 years’ worth of progress.

You’ve taken companies public, you’ve sold some off. What’s Rubicon’s fate?

The start of this company felt like unfinished business. It felt like L90 was a great success. But we were No. 2 to DoubleClick, so it was bittersweet. For me it was unfinished business. I want to be No. 1, and I think there’s a real opportunity to be No. 1. Right now, there’s Google and everyone else. The “everyone else” market is larger than Google; we’ve already disrupted the market, so we’re stopping short of nothing.

How did you and your wife meet?

We met at Rubicon. It’s a funny story: We found out that we grew up in Chicago close to each other. We grew up on different sides of the airport. And we later found out that my uncle coached her basketball team and our cousins went to school together. It was wild.

Was that awkward dating her while she worked for you?

The company was smaller at the time and it was a lot of friends and friends of friends. I spent all my time at the company. Shortly after we started, she left the company. But she understands what I do for a living, which is nice. She’s my own in-house consultant. It’s great because she knows the marketing side, having worked for the Wall Street Journal (a Rubicon client), so she knows the market really well and understands the business at Rubicon and she understands me. She’s been more helpful being outside the company than inside.