Couple Bootstrapped an EdTech Company to $10 Million

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.

Co-founders Mary Oemig and her husband, Eric, have been scrappy bootstrappers through a decade-long journey building Boom Cards and Boom Learning. Awesome 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?

Mary Oemig: I am the child of a blue-collar carpenter and a public school teacher who did, primarily, substituting. But my parents come from a long line of entrepreneurs. My grandfather on both sides of the family-owned their own businesses. My mom now runs the bar that she inherited on her side of the family. My dad founded his own construction company when I was young. I grew up in a world where entrepreneurship was normal even though it was in a small community in Idaho.

Sramana Mitra: Is that where you still are?

Mary Oemig: No, I have moved to Chicago. Because of that entrepreneurial spirit, I have always had this notion of I can make my own business. In college, I took a loan from my grandmother to create a business making flyers for real estate agents. That’s part of how I paid my way through college – through desktop publishing.

I ended up going to law school. I spent about 20 years advising technology startups on user-generated content. That’s my special area. I also advised a number of companies on how to straddle the world of fostering user-generated content without getting yourself in trouble and the nuances there.

Sramana Mitra: This was in Seattle?

Mary Oemig: This was in Silicon Valley. I went to law school at Berkeley and then worked at Fenwick & West for about three years. Then Microsoft recruited me to Seattle. I worked in almost every division of the company because I was in the Copyright and Trade Secrets group. We rotated which groups we worked with. My favorite is research. How do you take something from idea to production? That has been my core interest.

Sramana Mitra: Where does the entrepreneurial journey begin?

Mary Oemig: It begins with a prior entrepreneurial journey. I founded a small education co-op for children ages three to six. I was teaching. These kids were what we call highly asynchronous and twice-exceptional. They were strongly gifted.

Many of them also had areas where they struggled. These are children who are challenging to teach in a traditional classroom that’s designed for kids who are operating at roughly the same level across all subjects. It requires a lot of differentiation.

I knew all the education research and pedagogy I needed to be implementing, but I didn’t have any digital tools to make it easy. It was very time-consuming to use the processes to gather the right data and determine the right intervention. I would come home and complain because I don’t write code.

My co-founder and my spouse is a former performance engineer from Microsoft. He had been serving in our State Senate here where he had been working on public policy issues in K12. We both wanted to do something for education.

Our conversation continues here.

Looking For Some Hands-On Advice?

For entrepreneurs who want to discuss their specific businesses with me, I’m very happy to assess your situation during my free online?1Mby1M Roundtables, held almost every week. You can also check out our free?Bootstrapping Course, our?Udemy courses,?YouTube channel,?podcast interviews?with VCs and Founders, and, to?follow my writings, click "Follow" from?here.