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

Posted on Friday, Aug 14th 2020

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.

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.

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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