Serial Bootstrapping Entrepreneur’s Journey

Serial Bootstrapping Entrepreneur’s Journey

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.

Going against the grain of Venture Capital mania, in 1999, Beyond Security CEO Aviram Jenik started his second bootstrapped venture. When we spoke in 2017, 18 years later, he was still running it. In 2021, Beyond Security was acquired by Help Systems

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?

Aviram Jenik:?I was born and raised in Israel. I moved to California about 10 years ago. I spent most of my adult life in?Israel. I studied at the Technion which is like MIT in Israel. We half-jokingly say that pretty much everyone can say that they went to the top 10 universities in Israel because there are less than 10 universities. I’m an entrepreneur by background. I started my first company, which was bootstrapped when I was about 19.

Sramana Mitra: Let’s start there. What was this company that you started when you were 19?

Aviram Jenik:?It was a software company and we ended up selling it to Microsoft for just over $100 million. That was a pretty nice exit.

Sramana Mitra: What was the idea that you started with and why did you start with that idea?

Aviram Jenik:?It wasn’t really based on an idea. Bootstraps are very rarely based on ideas. They’re usually based on people wanting to do something. At least, that’s how it worked for me. I’ve done three bootstrapped companies. At least with two of them, we really didn’t have an idea when we started. We just got together.

We really weren’t sure what it was we wanted to do. We thought we wanted to do something in the education field. Then the Internet came along and we switched to the Internet. We thought about distance learning. We switched again. There were these PC manufacturers. We did software for them. We went around and did a bunch of things.

Sramana Mitra: You did whatever you could make money of.

Aviram Jenik:?Pretty much. It’s a little bit better than that. We were focused on technology rather than the services. It wasn’t that we were just doing projects to make ends meet. We were developing technologies for fields that were interesting at that time. We kept changing what we were doing. It took a while. Especially with bootstrapping, there’s always the tension between selling products and services.

Sramana Mitra: I would want to hear about what you did at 19. By the time you did Beyond Security, you had two exits. Beyond Security was a story of an entrepreneur who was very seasoned and with capital. That’s a very different story than a 19-year-old entrepreneur navigating his first startup.

Aviram Jenik:?Those first few companies were more like going around in the forest trying to find a way.

Sramana Mitra: The first company you started, you ended up selling to Microsoft for $100 million. I would want to know how that happened.

Aviram Jenik:?Just because we got to the right place doesn’t mean we knew the way.

Sramana Mitra: How does this relate to Technion?

Aviram Jenik:?At that time, I was just finishing my studies. What I learned was that formal studies is definitely not for me. I get into fights with professors. With formal studies, they want you to do something in a certain way. There’s a certain way to do stuff. You know how the math teachers always tell you that you always have to show the way. In my opinion, that’s not true. You have to build software that does something. How you built it and how many shortcuts you took, that’s nobody’s business.

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.


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