Best of Bootstrapping: Bootstrapped to Exit, Bootstrapped Again, then Raised VC Funds

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

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.

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Best of Bootstrapping: Bootstrapped Using Affiliate Marketing

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

Affiliate Marketing is at the heart of many wonderful bootstrapping stories. It’s inexpensive to get going and profitable quickly, and if managed well, can scale substantially. Zeeto Founder CEO Stephan Goss had bootstrapped a traffic arbitrage business to $42 million in 2015 revenue when we spoke in 2016. If you are working on an affiliate marketing / lead generation type of business, this is a useful conversation. You can listen to our entire interview [2:10 – 33:50] from our 1Mby1M YouTube channel:

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: Bootstrap, Pivot, Liquidity, Scale to $100M+

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

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 is my first introduction to the business world. I opened my first spreadsheet working in management consulting.

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

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

When we spoke in 2016, SurveyGizmo Co-founder Christian Vanek had bootstrapped the company to $13 million from Boulder, Colorado. He experimented with both freemium and free trial, and managed to monetize nicely. The company is now named Alchemer.

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: Bootstrapped a Custom Apparel Business to $23M

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

From setting up a printing machine in the dining room to $23 million in revenue when we spoke in 2016, RushOrderTees Co-founder 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.

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Best of Bootstrapping: Wonderful Bootstrapped with a Paycheck Story

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

This is a wonderful bootstrapping with a paycheck story of a really smart, scrappy entrepreneur, Suuchi Ramesh, Founder 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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Best of Bootstrapping: Bootstrapped First, Raised $120 Million Later

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

This discussion from 2020 with Madwire Co-CEO JB Kellogg includes all sorts of interesting nuances, including DIFM vs. DIY. Read on.

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?

JB Kellogg: I’m from Colorado. I was born and raised there. We moved around, but most of my childhood was in Colorado. I was very into sports as a kid. I grew up with that as my primary focus, which catapulted me into college on scholarship for football.

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Best of Bootstrapping: Bootstrapped to Over $10M First

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

Koncert (formerly ConnectLeader) CEO / CTO Senraj Soundar had bootstrapped his company to over $10 million in revenue before raising VC funds when we spoke in 2017. We love stories like this that reinforce our philosophy: “Do not go to VCs as beggars, go as kings!”

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?

Senraj Soundar: I was born and brought up in India, particularly in Southern India. I got my Bachelor’s degree in Electrical Engineering in Chennai. Around that time when I graduated, I received an award from the President of India for the best invention in the country. It was called the National Technology Award. They give out one award each year. I won that award in 1991, and it was given in 1992. The following year, I came to the US and went to UMass to get my Computer Science degree.

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