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

Posted on Friday, Jul 31st 2020

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


. Bootstrapping to an Exit
. Why is Bootstrapping Important?
. How Can You Play this Low-Probability Game Intelligently?
. Do NOT Go to VCs as Beggars - Go as Kings
. Excess is NOT Required for Success
. Bootstrap First and Raise Money Later
. Some Bootstrapping to Exit Case Studies
. The Buy Side of Bootstrapping to an Exit
. Blitzscaling vs. Bootstrapping
. Bootstrapping to Unicorns
. Cinedigm Acquires Bootstrapped 1Mby1M Company Future Today for $60 Million
. Mailchimp Bootstraps to $600M Revenue
. Bootstrapping from Arizona to $10 Million
. Bootstrapped Basecamp Executes a No Nonsense Strategy
. How Under30Experiences Bootstrapped to $5 Million
. Bootstrapping with a Paycheck
. How Algo.ai CEO Amjad Hussain Bootstrapped using Services from Michigan
. Seed Investors Who Like Bootstrapped Businesses
. How iHeartRaves CEO Bootstrapped a Niche e-Commerce Company to $20 Million
. Bootstrapping with Services
. How The Intern Group CEO David Lloyd Bootstrapped to $13 Million
. How Passageways CEO Paroon Chadha Bootstrapped from Indiana
. How SmartBuyGlasses CEO David Menning Bootstrapped to $50 Million
. Death by Overfunding
. How RainmakerForce CEO Mack Sundaram Bootstrapped Decisively to $5 Million+
. How FormAssembly CEO Bootstrapped a Virtual Company with a Paycheck
. TimeSlips CEO Mitch Russo Bootstrapped to Exit with Sage
. The VC-Entrepreneur Compensation Disbalance
. BioConnect CEO Bootstraps with Sophisticated Strategic Maneuvering
. Tremend CEO Marius Hanganu Bootstraps from Romania
. Gesture CEO Jim Alvarez Bootstraps to $10 Million
. SproutLoud CEO Bootstraps to $30 Million from Florida
. Tuft & Needle CEO Bootstraps to Over $100 Million
. Co-founders Bootstrap Linguamatics to Over $10M from the UK
. Ownership Matters
. Vainu Co-founder Mikko Honkanen Bootstraps from Finland
. Entrepreneur Couple Bootstraps to $10M from Colorado
. Power2Motivate CEO Bootstraps to $80M from Canada
. Financial DNA CEO Bootstraps to $10M+ from Australia
. Big Barker CEO Bootstraps a Niche E-commerce Brand
. PrecisionLender CEO Bootstraps to Over $10M from North Carolina
. Master Bootstrappers with Over $1B in Exits
. Ultra Mobile Founder Bootstraps to Over $100 Million
. Bootstrapping a Two-Sided Marketplace to $10M
. Can You Bootstrap a Virtual Company to Over $5 Million?
. Capital Efficient Entrepreneurs Turn $1M into $80M
. Discussing the Journey Through Failure to Success
. From a Small Town to $12 Million
. Bootstrapping to Y Combinator and $10 Million Series A
. Bootstrapping a Marketplace to Over $10 Million
. Freightwise Bootstraps to $33 Million
. Bootstraps First to $5M ARR, Raises $10M Later
. Bootstraps in Europe, Raises Money and Goes Global in the US
. English Major Bootstraps a Tech Company
. Bootstraps with a Paycheck to $15M from Tennessee
. Queue-It Bootstraps from Denmark to the US
. Bootstrapping A Virtual Company To $25M
. ActiveCampaign CEO Bootstraps Using Services to $40M
. Alteryx Bootstrapped with Services to a Public Unicorn
. Inspyrus Bootstraps Using Services to an Awesome Business Model
. CEO Bootstraps Using Services to Millions from Russia
. Wiredrive CEO Bootstraps Using Services to $10M
. Scaling to Over $10M by Bootstrapping Using Services
. Bootstraps Using Services from Poland to a US SaaS Company
. ButcherBox CEO Bootstraps a Perishable Meat Business to Significant Scale
. Waveform CEO Bootstraps to $8M
. Bootstrapped Entrepreneurship from Estonia
. From Laid-off Engineer to Successful Startup CEO
. Imagine Easy Solutions CEO Bootstraps to Exit
. BannerBuzz CEO Bootstraps to $35M
. Bootstrapping a Virtual Company to Scale
. Bootstrapping Using Services from Wisconsin
. Best Tactic for B2B Startups
. Bootstrapping by Piggybacking from Romania
. Bootstrap First, Then Scale with VC Funds
. Bootstrap to +$10M First, Raise Money Later
. Madwire CEO Bootstrapped First, Raised Money Later to $120M
. Bootstrap Using Services First, Raise Money Later
. Wonderful Bootstrap with a Paycheck Story
. RushOrderTees CEO Bootstraps to $23M
. Bootstrapping with Freemium and Free Trials to $13M
. Bootstrapping, Pivoting, Gaining Liquidity, Scaling to $100M+
. Bootstrapping with Affiliate Marketing
. Bootstrap to Exit, Bootstrap Again, Then Raise VC Money
. Bootstrapping Using Services to $12M
. Bootstrapping an Ad Tech Company from Paris
. Bootstrapping a 100% Virtual Company from Ireland
. MiQ CEO Bootstraps with Services from London
. Bootstrapping to $8M During the Covid Crisis
. Bootstrapping a Marketplace from Brazil
. Bootstrapping Using Services from Sweden
. What Should Startups Do To Raise Seed Capital in 2021?
. EdTech Unicorn Bootstrapped First from Canada
. Coalition Technologies Co-founders Bootstrap to $10M
. Bootstrapping a Virtual Company to $10M from Atlanta
. Bootstrapping a SaaS Company with a Paycheck and Scaling
. Bootstrapping with Services to $20 Million

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