Bootstrap, Pivot, Gain Liquidity, Scale to $100+ Million

Bootstrap, Pivot, Gain Liquidity, Scale to $100+ Million

I publish this series to discuss the nuances of bootstrapped entrepreneurship. Please subscribe to my Best of Bootstrapping series to never miss an article and?learn what to expect from 1Mby1M.

Fascinating story of MediaAlpha, beautifully told by Co-founder CEO Steve Yi in 2016. He relates how the team 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 was 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.


Looking For Some Hands-On Advice?

For entrepreneurs who want to discuss their specific businesses with me, I’m very happy to assess your situation during my free online?1Mby1M Roundtables, held almost every week. You can also check out our free?Bootstrapping Course, our?Udemy courses,?YouTube channel,?podcast interviews?with VCs and Founders, and, to?follow my writings, click "Follow" from?here.

CHESTER SWANSON SR.

Realtor Associate @ Next Trend Realty LLC | HAR REALTOR, IRS Tax Preparer

2 年

Attaboy for Bootstrap, Pivot, Gain Liquidity, Scale to $100 Million.

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