Bootstrapped to Exit, Bootstrapped Again, then Raised VC Funds

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 .

Stephanie Leffler, Founder of OneSpace, had bootstrapped her first company to $20 million in revenue from St. Louis when we spoke in 2016. Her second company, also from St. Louis, was?venture-funded and had crossed $10 million in revenue. Ascential acquired OneSpace in 2021. Awesome entrepreneur, inspiring woman! You can also listen to our conversation as a podcast here .

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.

Sramana Mitra: What did you do for education?

Stephanie Leffler:?Just a basic Bachelor’s degree in college. I majored in Business Administration. When I graduated, I did not know very much about the Internet. From a timing perspective, I sent my first email during my freshman year. I had gotten online in my high school library a few times prior to that.

Sramana Mitra: When did you come out of college?

Stephanie Leffler:?In 2000.

Sramana Mitra: This is right after the dot-com crash?

Stephanie Leffler:?That’s exactly right.

Sramana Mitra: What happens next?

Stephanie Leffler:?During my senior year, I wrote a business plan with a friend to sell sun-protective clothing online. After writing the business plan, we decided to pursue doing that. During the second semester of my senior year, we built our online store and sourced the product. Ultimately, we launched a website. When we graduated, we moved to St. Louis, mainly because his dad was a commercial real estate developer and we knew we could get free or very cheap rent if we worked out of St. Louis. That was how everything got started.

Sramana Mitra: This company is OneSpace?

Stephanie Leffler:?No, this is my first company.

Sramana Mitra: Let’s actually do that story. You moved to St. Louis. You had a business plan and a co-founder. What happens next in that story?

Stephanie Leffler:?We were planning just to bootstrap everything, which we did. We both had a small savings account from waiting tables in college. We just set out to try to make a dollar more than we spent. We started to build this online store and found out very quickly that it was really difficult to build an online store at that time. There weren’t a lot of tools available.

You generally used a developer and it was tough. Seasonality hadn’t necessarily accounted for that. We realized that retail was going to take a long time to make it big. What we did figure out was it would be great if there was a tool to make it easier to build an online store. We found a do-it-yourself online store builder and started to use it for our store.

We realized that just like the people during the gold rush, the people who made the money were not necessarily the gold miners. We said, “What if we put our focus on figuring out a way to buy this company or grow this e-commerce company and leave retail behind if we can?” We were able to do that. We worked with the founder of the e-commerce company to become his sales team.

Eventually, we were selling so much that we were able to buy the company from him. That company became known as Monster Commerce. We were one of the five customers when we first started using it. We grew it to more than 10,000 small businesses and sold that to Network Solutions in 2006. We had about 80 people when we sold the business. Network Solutions scaled up after the acquisition to about 250 people here in St. Louis.

Our conversation continues here .

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