As part of CEO Insights series, the Chief Executives Council recently interviewed Cleve Adams. Cleve Adams is a five-time VC/PE backed tech CEO, with over 20 years of experience in leading, transforming, and selling companies in the cybersecurity AI and SaaS markets. One of the five of those was Websense, the first cybersecurity unicorn. Cleve has delivered an average return of 21 times to investors and successfully completed two IPOs and four acquisitions, managing companies from startups to 2 billion. Cleve is currently the founder and managing partner at Trestles Group that invests in and advises growth in late-stage companies. He is a member of the Forbes CEO Council and a board member of software startup XQ. He earned an MBA from Pepperdine University where he serves on the board of advisors for the Graduate School of Business and Management.

Following are questions from moderator Neil Brown, and answers from Cleve Adams. If you are interested in learning more, view the full interview video archive here.

Q: Your career is focused on technology including cyber, AI and SaaS. How did this specialty come about?

A: Well, put it this way, in 1996, which was 27 years ago, I had just sold a company that I was with, helped sell a company, and I was introduced by a friend of mine to another guy that was looking for an executive to help him so he could start a company. So, the company was Websense and the technology wasn’t even named cybersecurity yet. It was so early; they didn’t have a name for it. So, it was just security software. And there wasn’t such a thing as SaaS, but that’s what it was, a services software, which we then built. So how I got into it is I was just introduced from a friend of a friend to another guy that was looking for an executive to help him start a company.

Q: What are your responsibilities as a CEO and how do you think they differ for you being a VC/PE advisory versus an operator, CEO, let’s say?

A: Well, I’m an operator, CEO, so I can answer both of those, right? I’ve been operating startups, like I said, since the 1990s. I’ve done quite a few of them. I have stepped in and become an operator for many different companies all the way up to a hundred million ARR. So, when it started off in my career as a becoming a CEO of a software company in the cybersecurity area, which was in the SaaS areas, the first SaaS company in existence. Then when I went to more of a consultative role, I was an M&A advisor and an investor in companies. But what happened is when I invested in companies or when I advised companies on mergers and acquisitions or IPOs or whatever, or helped them raise money, I would get offered to come into the company and help operate it. So, I’m an operator at heart.

Q: Share some of the most interesting aspects of your job.

A: I get to see all kinds of technology from cybersecurity to artificial intelligence to software as a service. So that’s one of the best aspects is all the different technology that I get to see. The other thing is I get to pick and choose which companies that I think will do well. So another exciting aspect is I see great technology, I get to choose from, and try and sort out which ones are the good ones and which ones are the bad ones. And then another great aspect of my job is that sometimes I get asked to come into the company and help run it and make it a better company.

Q: Top three significant keys to your success

1. Work Hard
2. Learning a lot – from your mistakes and your success
3. Stay Humble

To learn more, view the full interview here.