Darren Guccione | From Rockstar Musician to Rockstar CEO

Darren Guccione is the Co-founder and CEO of Keeper Security Inc., a password management application that works with various companies including AT&T and HTC. It protects more than 10 million consumers and over 3,000 organizations worldwide. Darren is a cybersecurity expert and entrepreneur who has been quoted in media outlets including CBS Evening News, Fox & Friends, USA Today, ABC, and Mashable. He has also been named to the “Chicago Top Tech 50” by Crain’s Chicago Business. Before taking the entrepreneurial route, Darren was an aspiring rock star musician.

In this episode of the Smart Business Revolution Podcast, John Corcoran interviews Darren Guccione, the Co-founder and CEO of Keeper Security Inc., about his journey from being a rockstar musician to entrepreneur. They also discuss the effects of the pandemic on cybersecurity, tips for promoting data breaches, and how to be a great leader.

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Here’s a Glimpse of What You’ll Hear:

  • Darren Guccione’s experience singing with a rock band
  • How Darren joined the finance industry, helped build Apollo Solutions, and influenced the sale of Apollo to CNET Networks
  • Tips for getting feedback from customers and protecting user privacy
  • How the pandemic impacted the cybersecurity industry
  • Why companies under-invest in cybersecurity
  • Darren’s tips for managing competition and being a great leader
  • The peers Darren respects

Resources Mentioned In This Episode

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Episode Transcript

Intro 0:14

Welcome to the revolution, the Smart Business Revolution Podcast, where we ask today’s most successful entrepreneurs to share the tools and strategies they use to build relationships and connections to grow their revenue. Now, your host for the revolution, John Corcoran.

John Corcoran 0:40

All right, welcome everyone. John Corcoran here, the host of this show. And if you’re new to this program, if you haven’t heard it before, check out our archives because we got some great interviews, including I want to specifically point out my episodes with Derek Harp and Paul Farrell, if you’re interested in the topic that we’re gonna be talking about here today, but also in the archives. We have interviews with smart CEOs, founders and entrepreneurs from Netflix to Kinkos’, YPO, EO, Activision Blizzard, LendingTree, and many more. And of course, I’m also the Co-founder of Rise25 where we help connect b2b business owners to their ideal prospects. My guest here today, first shout out to Steve K. Han was one of my past guests, who I asked him who he’s grateful for. And Darren’s name came up. His name is Darren Guccione. He’s a cybersecurity expert and entrepreneur. And the creator of Keeper, which is a password management application, works with many different companies from AT&T to HTC, predicts more than 10 million consumers and over 3000 organizations worldwide. And he’s also a cybersecurity expert who has been quoted in all kinds of major media outlets from CBS Evening News to Fox & Friends, USA Today, ABC, and Mashable, and also been named to the Chicago Top Tech 50 by Crain’s Chicago Business. And fun fact, was an aspiring rock star, which we’ll get into at the beginning of the interview.

And of course, this is brought to you by Rise25, my company, where we help b2b businesses to get clients, referrals, and strategic partnerships with done-for-you podcasts and content marketing. And you can learn all about it by going to our website at rise25.com. All right, Darren, pleasure to have you here. And I love the name of your band. So you’re studying engineering, and you also have this band. You’re kind of like a hard rock aficionado, and your lead singer of this band and kind of going in two very different directions, which is kind of fascinating to me. First of all, start with the name of the band, and what are you thinking as you’re graduating from? from college? Are you thinking like, I’m gonna prove, pursue, you know, becoming a rock star? And if that doesn’t work out my backup is engineering and entrepreneurship. And that just seemed a little bit crazy.

Darren Guccione 2:47

No, but I think music has always been a love of mine. You know, since the sixth grade, I was in bands, really since while probably 13 years old, and the band and college at U of I was named yuppie hippie. I think it was sort of it was indicative of I think how we viewed ourselves. Most of us were engineers. Our drummer was in pre law, but we were all engineers are one of our lead guitars, we had to lead guitarist one was an industrial design became a toys designer, and he was amazing. But yeah, it was yuppie hippie. We played every Friday and Saturday, like clockwork we practice on Thursdays. And then every other day was, you know, basically engineering. You know, they gave you five hours a day of homework. So kept us pretty busy.

John Corcoran 3:35

Yeah, for sure. And you actually went off to Los Angeles to Hollywood to pursue your music career right after graduating. But once you got there, and you decided that you it wasn’t the right lifestyle for you. So if you’d put so much time and energy into this, what was it about? Kind of going pro that made you feel like, this isn’t for me?

Darren Guccione 3:57

Yeah, well, I was, you know, I had this goal of becoming a lead singer of a, you know, popular rock band, or at least joining a rock band and becoming huge and playing arenas and stadiums. It’s just something that I aspired to do, because I loved it. And when you know, sometimes when you have a vision of something, and you actually go out and do it, it’s just, I think, just generally the scene, the band members, the environment, what I wanted to do, just the overall trajectory wasn’t there for me. And I decided to just pivot and I was offered a really a fantastic position with a company named Bell sports at a Rantoul, Illinois, the lead product engineering, I think, at a very young age, and that would bring me to the Far East so I lived in Asia for two and a half years with Belle sports developing, you know, and CO designing mountain bike products. So my job was to take the designs from you know, Los Gatos, California is where we were located and Bring those designs to reality. So I take the designs, bring them to the factories, and I wouldn’t come back from the far east until those products were produced. So I had a, you know, a fantastic time doing that. And I stayed in the music scene, I did some work, you know, with some rock bands, you know, in between, but it was a, it was a passion of mine, you know, I’ve always believed, like, if you if you’re passionate about something, you’ve got to pursue it, because the worst thing in life would be to die with regret. And that’s something that I know will never happen with me because I’ve always pursued. Yeah, and if I didn’t like it, I would just pivot and try something else.

John Corcoran 5:37

Okay, so this sounds like a fairly standard trajectory career trajectory, like you’ve heard a million times before. And studying engineering undergrad, to Rockstar to designing and producing mountain bikes in the Middle East, fairly standard. And then you end up with tell us about Apollo Apollo solution. So this is an interesting company. We’re talking late, you know, kind of the tail end of the.com era, so late 90s companies around for less than two years, and then is sold to CNET. So talk about

Darren Guccione 6:09

that. Yeah, yeah. Well, before that, there’s a really important point is that, you know, I was a golf caddy since I was 12. That was my summer job. And I became an that was not my

John Corcoran 6:19

bingo card. By the way, golf caddy was not the next one. Yeah, so

Darren Guccione 6:23

I was a golf caddy, you know, my hair at the time, it ultimately grew to almost the bottom of my bag. So my nickname was hair, as in the hair on my head. And that was cool, because I was given the Evans Scholarship, which was a blessing. And it’s a you know, full ride, it paid for my school at U of I. Well, as I was chatting, I wound up meeting, a gentleman who did mergers and acquisitions. He was a CPA. And, you know, ultimately, when I was with at Bell, I decided that you know, what, I’d love to pursue business and finance. So I went back to grad school in Chicago, got my Master’s in finance and accounting, sat for the CPA exam, and then ultimately went to work for him for two and a half years doing mergers and acquisitions. When I was there, the advent of the Internet and that proliferation, you know, began to really take hold. And that’s when I decided to ultimately leave and start my own firm. And the first month I started my own firm in m&a, I wound up meeting Craig Lurey, from a payroll company named paychecks, you know, paychecks the payroll company,

John Corcoran 7:33

was he trying to sell to you trying to sell his services

Darren Guccione 7:36

to? No, so what happened was paychecks came in to sell payroll services, and I just started and they said, Hey, do you have any clients that need payroll? And I said, I don’t have any clients yet. I just started in this young lady, really cool. She said, hey, you know, I, I met this guy named Craig Lurey. And he’s in the process of, you know, leaving Motorola to start his own company. And he built some kind of software, and he’s looking for somebody to help him with his business plan. Can I make an introduction? I said, Sure. So that’s how Craig and I met Craig, as you know, today is the CTO and co-founder of Keeper. So we’ve been partners, really since October of 1998. In different business ventures. Yeah.

John Corcoran 8:18

Wow. Wow. So tell us about Apollo because this incredibly fast as for even for the.com era, less than two years, and then it sold out to CNET? Well, you were in it was actually one of the first e-commerce software engines.

Darren Guccione 8:32

Yep. So Craig, and I met at a restaurant I just said, Hey, you know, bring your file cabinet with you. I was it was a, you know, figure of speech. And I didn’t realize it, but he actually pulled his file drawer out and brought it to the restaurant, he walks in with a big metal file drawer, has everything in it. And if you met Craig, you’d know that he’s eccentric in that way. And that’s like, no big deal. So we went through everything. And I said, look, the first thing I want is, I don’t want to look at numbers, you know, show me the product. So it was really cool, because it was a web based ASP solution. One of the first of its kind, you know, for buying and selling computer products over the internet, and I looked at it and I said, Oh, my God, like, this is the future. Now remember, this is like 1998 when, you know, people would barely even think about putting a credit card into a computer.

John Corcoran 9:20

Right? In the early days of Amazon even. That’s right. So

Darren Guccione 9:23

most people were still shopping in malls and hanging out at the mall and going the stores. And I was looking at this like, oh my god, like let’s see free parking. You don’t have to drive there. It’s super fast. You can compare products instantly, right? Get real time pricing and inventory information, and secure purchase within a few seconds. This is awesome. This is the future. So we sat down and I said hey, you know I’m not that busy with my firm yet. I just started so how about if we joined forces, I’ll be your CFO. I’ll help you know build the business plan help you with that. All the infrastructure. And you don’t even know you had no clue?

John Corcoran 10:03

No, even though you had the engineering background, it sounds like you, you still stayed away from like coding or anything engineering.

Darren Guccione 10:11

That’s right. Yeah. So the way that we delineated the business is exactly how we operate today. So I work closely with the front end. So design team reports to me, and then, you know, everything from finance, HR, sales, marketing, I would take care of that. And then Craig would lead on the development, so QA, Dev, engineering, sec, ops, DevOps, all of that falls under Craig. And that’s exactly how we operate at Keeper today. So we bifurcate the responsibility on the business. And it’s worked beautifully. Well, no, since the early days.

John Corcoran 10:47

Yeah. So you must have some kind of traction if CNET acquires you in less than two years.

Darren Guccione 10:52

Yeah, well, what was interesting was, you know, we, we were living off of like credit cards at the time. You know, Craig had, like, you know, I think multiple mortgages on his house, I was living on my mom’s couch. You know, we have this office in Addison, Illinois. And we had this really clear vision and a fantastic product. And I said, Look, we need to raise some capital, we need to do a Series A, so there was a trade show. You know, you remember, Comdex back in the day? Yeah. Cena was exhibiting there. And first demo that CNET saw, they just said, is this real? Or is this you know, just sort of a mock up? I’m like, No, it’s this is real. And they said, we’ll be in your office next week for diligence, we want to invest. And they came out on a Monday. And the following, I think it was Monday or Tuesday, they had wired us, you know, $2 million on a Series A, and then won’t, you know, wound up purchasing the rest of the company 18 months later. So it was pretty amazing, you know, to go from, you know, living on your mom’s couch and eating ramen noodles every single day, to having, you know, a fantastic outcome 18 months later, so it was really great, what a