For more than 25 years, Grant Asplund has been sharing his insights on how businesses can best protect themselves from sophisticated cyber-attacks in an increasingly complex world. As Check Point’s chief evangelist, he travels the world enthralling audiences with his passionate and relational storytelling at conferences like RSA and Next100 CIOs and numerous media interviews. Grant is the host of the CISO Secrets podcast and the Talking Cloud Podcast on Cloud security.

So Grant, how did you get into cybersecurity?

I tell my kids all the time, life is like falling down a mountain. You really don’t control much, you want to try to stay on your feet as best you can, not get hurt, not hurt anybody. And for me, it was very much that way. A recruiter called when I was out of business and skidding on my chin at probably the lowest part of my life. I was separated. It was dreadful. And the recruiter says, “Hey, we’re looking for a hotshot sales guy.” And it was like, okay, I’m there. I went to work for this small company with 35 employees called MetaInfo in Seattle. They were the first in the world to port BIND, the DNS BIND protocol to run on Windows. I went to work in early February, 1998. And on April 15th, 1998, Shlomo Kramer flew to Seattle and announced to all of us that we had just been acquired by this company headquartered in Israel called Check Point Software. And so that’s how I fell down the mountain into cybersecurity.

And now you’re a global evangelist at Check Point! What does an evangelist do?

This is incredibly near and dear to my heart, because the very first time I even heard of the title was when I helped open up an Apple dealership in 1983. I heard of this guy who helped introduce the Macintosh, Guy Kawasaki. His title was Apple Evangelist. I was so intrigued by that, I thought, man, that’s what I want to do. That’s what I want to be. And so for me, my ideal image of an evangelist was Guy Kawasaki. He was technical, but not uber technical. He understood it all conceptually. He could explain it very, very well. He used layman’s terms to make it very easy to understand what arguably could be very complex subject matter. That’s what an evangelist does. An evangelist goes into a greenfield world and gets everybody to want to get on his or her bus. I always see this industry like a train station in Munich and there are literally dozens of trains on multiple platforms. Each one has an evangelist saying, “Hey, get on my train.” You may not know where it’s going, but an evangelist’s job is to get you on their train. I’ve for years said that an evangelist is like a hood ornament on a car. They don’t have anything to do with driving the train. They don’t really have anything to do with the functionality of the car, but it’s one of the first things you recognize and assess the quality of that vehicle. And I really take a great deal of pride in the fact that I was Check Point’s first worldwide evangelist in 1998! I’m so thrilled that I can be back doing it again for the company. It’s pretty cool.

Why did you leave Check Point?

In the early 2000s, Check Point had some 419 employees and we were at about $140-ish million a year in sales. Everything was great until the tech bubble burst. That was actually when I decided to leave Check Point, but it wasn’t that I wanted to leave. In fact, I never really left Check Point. What happened was I heard that Gil was going to end of life the company product, MetaIP, which was the acquisition I joined through. A colleague said, “Hey, you should go buy it back if you think you can make a run at it.” And I was naive and young and believed I could. So I went and talked to Gil and he said “sure, he was open to it.” I negotiated and in January of 2002, I took over MetaInfo. We started with three people, myself, Steve DeJong and Ernie Vanden Ende. And we grew it. We managed to survive and in fact, Check Point retained a small percentage share of the company. And so I never really left. I didn’t quit, I didn’t get fired. I just took MetaInfo back and then subsequently resold it again to a company called Neustar. And so that was why I left Check Point, although I never left Check Point.

So why did you come back to Check Point?

The irony, I mean, you can’t make this stuff up. When I was at Check Point, I met many great people, many of whom are still friends. One of them was Zohar Alon, Founder and CEO of Dome9. I saw Zohar at RSA in 2018 and I said, “Hey, I should be evangelizing for you guys.” And a few months later, I was the principal evangelist at Dome9. And what do you know, a few months later, Checkpoint acquired us. And I was thrilled to hear that I was going to be back at Check Point. You can’t make this stuff up. That’s why I’m back. And it’ll be five years very soon.

You’ve had quite the wild ride, being the first evangelist at Check Point, leaving to run a company and eventually finding your way back. What makes you stay at Check Point now?

It’s very emotional for me because it’s changed my life. Never in a billion years did I ever dream that my career would have been as awesome as it has been. I’m just a regular guy. I put my pants on one leg at a time, like everyone else. But I’m really, really fortunate. The fact is, I love Check Point. I love the fact that we’re the steady eddy you can always count on. I love the fact that we’re unequivocally the best when it comes to building security products. I’m here because I have a role and I have a great story to tell. And there’s so much that people don’t know about Check Point because we haven’t been out shaking the pom poms quite so much. But I love the company. I think that Gil Shwed has been spot on with his overall strategy and plan to build the Infinity architecture, that really is like that spider web that knows when there’s a fly in any corner, whether it’s cloud, endpoint, a data center or anywhere in between. The pundits are telling us he’s right. We’ve been waiting for the puck for quite some time. And it’s really awesome to be at a company where you can tell that story. I just love being here.

Any advice for others interested in becoming technology evangelists?

You have to understand and be able to tell stories and articulate the technology. I’ve been asked many times, “what is it that you do that makes you as effective as you are?” And while I absolutely put my pants on one leg at a time, like everybody else, I work every day on trying to be better. What it comes down to, is what I always call EESP: it’s energy, enthusiasm, sincerity, and passion. I really believe those are the qualities. I have to share one thing that I really believe in, that everyone needs to think about. It’s a quote from Vincent van Gogh. “If you hear a voice within you say, you cannot paint, then by all means paint, and that voice will be silenced.” I love that. Deep faith eliminates fear. If you think you can or you think you can’t, you’re right. I really believe anybody can do anything they want. If you want to be an evangelist, go be an evangelist. Don’t be me, don’t be Guy Kawasaki, be yourself, be genuine, be sincere, and take it seriously. I have to give a shout out to Dameon Welch aka Phoneboy because he said something that really flattered me. I just love to know that someone like him and others maybe look at me. He was introducing me to someone right after I had come back to Check Point through the acquisition of Dome9. We were at headquarters in Tel Aviv and he and I were walking around and saw someone. Dameon introduced me and he said, “Oh you’re one of the Office of the CTO evangelists.” And I started to answer yes. And before I could even answer, Dameon jumped in and said, “No, he’s not one of them. He’s the OG evangelist.”

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