Driven: How Did I Get Here Ep.13 – From Tech to Guiding Founders Through the Waters

Chad Jones, CEO of Plesso Ventures, discusses how he catapulted into the VC world.

What is your current job?
I’m a serial entrepreneur and venture investor. I came up through the tech space and a number of different startups, and have gone through several acquisitions. I leverage the money I was blessed with from there to now invest in early stage ideas. I’m always looking for the next great idea that is at the seed or angel phase where I can help through my own investment or coordinating investments.

Let’s rewind – what did you want to be when you grew up?
I went to my guidance counselor’s office back in high school and they asked me the same question! I said I wasn’t sure, but I know I don’t want to wear a suit every single day. Little did we know at that time the technology explosion was just around the corner. When I was a kid, I wanted to be an astronaut. I was inspired by the space shuttle program and it really spoke to my imagination that anything could be possible. I got into discovering computers in the 1980s. My first computer was an Atari 2700, and it hooked me into all that was possible with computers.

At what point in your career path did you start to hone in on what you’re doing now?
Through fits and starts. In high school I wrote an inventory program for a company and ran it on an early network system, which was a big deal at the time. Then I went to college for a few years. I had been playing beach volleyball, so I actually jumped out and played semi professional beach volleyball on the AVP tour for about five years. Then I realized, this is a fun lifestyle, but I’m not going to make money doing this. So I jumped back into technology in the mid-90s as the internet bubble started to rise and focused my career on virtualization in the early Citrix days. I was part of a company that was acquired by a service provider – basically a cloud provider before it was called cloud. Before I could cash that check the bubble burst, so easy come, easy go, right? But to make a long story short, it opened my eyes that building companies, making them worth something and selling them can be quite lucrative. So I started to investigate how to do that. And now I get to do my favorite thing, which is to effect meaningful change.

Where did you go to learn how venture-backed businesses work?
I had a crash course in the basics by mentors and executives from companies I was with. And I read as much as I could. Today, you have Shark Tank and everyone seems to be wanting to jump into this game. People can go online for great resources and talks, but remember there’s an art to understanding what these deals actually mean. There’s one really good blog series by David Skok out of Harvard iLab I highly recommend. I did a video for Harvard iLab called, “The Business of the Internet of Things.” I did it to set an example of how I actually approach building businesses. Now it’s the third highest video for Harvard’s iLab in viewership. My advice for others is to just start reading.

What are keys to finding great mentorship?
You can look at mentorship in two ways, first as an outside source to give you information and knowledge. But another way is to look at it in a semi-political way, choosing someone who you can bounce only certain ideas off. I view a true mentor as someone you can ask any questions and there’s trust so you don’t worry you’ll feel stupid, that way you could get real answers back. Finding a network of mentors is important. You don’t want just someone with book knowledge, you want real world experiences.

What was the most important thing you learned at the beginning stage of your career? What allowed you to really parlay this experience and move on to the next level?
I knew after the first acquisition I went through that I wanted to be in that situation again because I realized taking a paycheck is awesome but if you wanted to create wealth, then it’s through markers of ownership. I always balance my deals with cash and equity, because equity is going to be the thing that gets you to the larger wire transfer day that will allow you to compound that into other investments.

What’s your favorite interview question?
The best question is to ask what drives them. It’s a question that shows your true self and what fulfills you as you’re going through your work. If work isn’t fulfilling, then it becomes something that you grind through and you may not love. Understanding what truly drives someone will tell you a lot about that person.

To contact Chad, find him on LinkedIn, connect with him on Twitter at @cloudjones or email him at

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