Best of Bootstrapping: Bootstrapping, Pivoting, Gaining Liquidity, Scaling to $100M+

Fascinating story of MediaAlpha, beautifully told by Co-founder CEO Steve Yi, relates how the team has navigated through various experiments to over $100 million in revenue.

Sramana Mitra: Let’s start at the very beginning of your personal journey. Where are you from? Where were you born, raised, and in what kind of background?

Steve Yi: I was born in Seoul, Korea. When I was seven, my family immigrated to Minneapolis, which is where I consider myself to have grown up. I went to high school in a small town. I went to Harvard College and majored in East Asian Studies. I had no idea what I wanted to do afterwards. I gravitated towards professional services. I worked at a company called Mercer Management Consulting, which is my first introduction to the business world. I opened my first spreadsheet working in management consulting.

After management consulting, I had some ideas about potentially going in and working with some social justice issues. I went to law school instead of business school with the thought that if I didn’t want to do that and I wanted to go back into the business world, I could effectively use my law degree in lieu of an MBA. After law school, I came to the conclusion that I wanted to go back into the business world, in part, because creating and running a great business that values its people and does something interesting and good for the world was one of the most impactful things that someone could do.

From law school, I looked forward to the path of having my own company or having my own startup. I graduated from law school in 1999 at the height of the first Internet boom. I went to go work for Goldman Sachs with an eye on using that as a platform to jump to the Internet space. After a year at Goldman, I took a job with an Internet company here in Los Angeles.

Sramana Mitra: What year are we talking?

Steve Yi: This was in 2000.

Sramana Mitra: In 2000, you quit Goldman and took a job with an Internet startup.

Steve Yi: Yes. The timing wasn’t great because a few months into that job, the crash started to happen. In 2002, we did have a sale of that company for a relatively modest amount – not the billion dollars that we were expecting. At that time, I think I really had to make the biggest decision. The veneer was off working in the startup space. What a lot of the colleagues who I worked with at that startup and other startups ended up doing was go back to management consulting, investment banking, or law.

I had already taken those professional services routes and I knew that I really wanted to build a business. I decided to stay with the Internet startup path. I worked for a series of Internet companies here in Los Angeles and focused on Internet advertising because that was one area that Los Angeles – not Silicon Valley – was particularly strong at. I worked for a variety of bigger and smaller companies, had my own startup, failed miserably, and tried again, and then failed not so miserably.

Our conversation continues here.

This segment is a part in the series : Best of Bootstrapping