Best of Bootstrapping: Bootstrap to Exit, Bootstrap Again, Then Raise VC Money

Stephanie Leffler, CEO of OneSpace, bootstrapped her first company to $20 million in revenue from St. Louis. Her second, also from St. Louis, is venture-funded and crossed $10 million in revenue. Awesome entrepreneur, inspiring woman!

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

Stephanie Leffler: I am from Northern Virginia in Fairfax. I was actually born and raised there. Ultimately, I went to school at Washington and Lee University. I found my way to St. Louis as part of my entrepreneurial journey. I’ve lived here ever since.

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Best of Bootstrapping: Bootstrapping with Affiliate Marketing

Affiliate Marketing is at the heart of many wonderful bootstrapping stories. It’s inexpensive to get going and profitable quickly, and managed well, can scale substantially. Zeeto CEO Stephan Goss has bootstrapped a traffic arbitrage business to $42 million in 2015 revenue. If you are working on an affiliate marketing / lead generation type of business, this is a useful conversation.

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

Stephan Goss: I was born in Switzerland, pretty close to Zurich. I came to the US in 2007.

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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.

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Best of Bootstrapping: Bootstrapping with Freemium and Free Trials to $13M

SurveyGizmo CEO Christian Vanek has bootstrapped SurveyGizmo to $13 million from Boulder, Colorado. He has experimented with both freemium and free trial, and has managed to monetize nicely. Read more about the strategies that have worked for him.

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

Christian Vanek: I’m from upstate New York originally. I was born in 1977. Honestly, I moved around quite a bit. I never went to the same high school for more than a couple of years. In the end, I ended up in Massachusetts. After high school, I had no idea what to do with my life. I was not the best student ever. The beginning of my journey was probably when I decided to do a year of service for AmeriCorps as part of an urban peace corps that had started in Boston and spread around the United States. Through working in the homeless shelter there and building a software package to help manage clothing and service distribution, I got my hands dirty and started getting the bug of building software for other people.

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Best of Bootstrapping: RushOrderTees CEO Bootstraps to $23M

From setting up a printing machine in the dining room to $23 million in revenue, RushOrderTees CEO Michael Nemeroff’s journey is one of steady, diligent execution.

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

Michael Nemeroff: I was born and raised right outside Philadelphia. That’s where I’ve lived my whole life. It all started in high school. My parents were entrepreneurs. They owned a clothing line. It’s a lot different from what we do today.

Sramana Mitra: Having an entrepreneurial family is a very big driver in a lot of people becoming entrepreneurs because you grow up in an atmosphere where risk and working on your own enterprise is an accepted psychological premise. That’s a very big deal actually in any entrepreneur’s journey.

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Best of Bootstrapping: Wonderful Bootstrap with a Paycheck Story

This is a wonderful bootstrapping with a paycheck story of a really smart, scrappy entrepreneur, Suuchi Ramesh, CEO of Suuchi.

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

Suuchi Ramesh: I was born in India. I spent the first 15 years in Madras, which is Chennai now. My family is in Bangalore, so I went to school in Bangalore. I’m a software engineer. Bangalore has a lot of great technology companies. I came to the United States on a tech job.

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Bootstrapping with a Paycheck from New Jersey: Suuchi Ramesh, CEO of Suuchi (Part 5)

Sramana Mitra: How much did you do in 2018 in product revenue?

Suuchi Ramesh: It was about 10% to 15% of our revenue at that point. We only started commercializing towards the end of the year.

Sramana Mitra: How did that split change in 2019?

Best of Bootstrapping: Bootstrap Using Services First, Raise Money Later

Rich Waldron, CEO of Tray.io, is building an authentic tech company from London. While the company could have become a so-called Unicorn by loading up on liquidation preferences, they have chosen not to do so. Excellent story.

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

Rich Waldron: I was born in the UK in a place called Southampton, which is right down on the South Coast. Its most famous claim to fame is where the Titanic set off from. I was born there 35 years ago.

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