How Do You Grow A Hard-To-Explain Business?

This is the story of a woman who launched multiple successful tech companies and a venture capital firm.

In 1997, Maria Cirino co-founded i-Cube, which (2 years later) sold to Razorfish for $677 million. She followed that up in 2000 with Guardent, which (3 years after that) sold to VeriSign for $135 million.

In 2006, she became the co-founder of .406 Ventures, where she is right now an early stage venture capital firm whose investments include Mashery, a provider of on-demand API management and Memento, which provides fraud management.

Maria Cirino

Maria Cirino

.406 Ventures

Maria Cirino is a co-founder of .406 Ventures which provides capital and operational expertise to help innovators become tomorrow’s market leaders.

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Full Interview Transcript

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Here’s the program.

Andrew: Hi, everyone. My name is Andrew Warner. I’m the founder of Mixergy.com, home of the ambitious up-start. And this is the story of the woman who launched multiple successful companies and a venture capital firm. In 1997, Maria Cirino cofounded i-Cube, which just two years later, sold to Razorfish for a reported $677 million. She followed that up in 2000 with Guardent, which three years later, sold to Verisign for $135 million. In 2006, she became the co-founder of 406 Ventures, where she is right now an early stage venture capital firm whose investments include Mashery, a provider of on-demand API management and Memento, which provides fraud management. Maria, welcome.

Maria: Thanks, Andrew.

Andrew: Hey, Maria, all those numbers that I spat out there in the intro, trying to make sure that the audience knows how big a guest you are to me, are they accurate? Does it sound right? It was all from the research that I was able to pull from at least two sources, but I was sensing that maybe I was off when I was looking at you as I read it.

Maria: You’re a pretty good judge of facial characteristics. So, ball park, but let me make a couple of corrections for you. First of all, I was very fortunate to be an early executive within i-Cube, but I was not one of the cofounders. We had an esteemed co-founding group, but I was, pretty much, the person that came in and ran the commercial side of the business from ’97 until we sold it in ’99 and then I stayed on at Razorfish for a year. And Guardent, we actually sold for $142 million to Verisign in 2004.

Andrew: I see. All right. So I was off and I appreciate the correction. Let me see if I can understand this, actually. When I looked up what i-Cube did, the word the kept coming up over and over again, and my suspicion is that the reporters who wrote about it, didn’t even necessarily know what the company was, was all they kept saying was “back-end”. They were just kind of hanging on that word and saying, “This will help you understand what I don’t yet, as a reporter, understand.” Can you help us understand what this business was?

Maria: Yes. It was the toughest and most lucrative job I ever had.

Andrew: OK.

Maria: Probably what made it so tough was exactly that, very, very difficult to describe what the company did and very hard to differentiate. Essentially, we were a systems integrator that helped large organizations deal with their legacy applications. Around that time, ’98, ’99, 2000, the big thing that they were worried about was Y2K and the other thing that they were worried about was, in many cases, these applications had been running within their organizations for 20-25, sometimes 30 years. They were deathly afraid of changing the logic associated with those applications.

Yet they knew that the hardware that those applications was running on would stop running, literally, on January 1st of 2000 and so what we did was build a whole company around this notion that we would preserve the logic within a legacy application, transform it so that it would run on a new class of, back then it was NT or Client Service Systems and we would also do it on a fixed time, fixed price basis, which was very unusual because these were two-year, three-year type of consulting engagements, and $14 million, $16 million price tags.

For us to actually have the confidence in our ability to land that delivery 24 months from the day we started, and pick up our check for $14 million was really gutsy, and very, very few companies would operate that way. They would fix-price a piece of it but then they would do time and materials for the rest, and so it made us very popular with very large organizations that were dealing with these legacy applications. That’s the most concise description I’ve ever given of the company and that took us three and half minutes.

Andrew: By the way, you did a great job of explaining something that, I’m telling you, I did all kinds of research on you and I don’t think anyone did as clear a job of explaining what the business did. You said it was lucrative. What do you mean?

Maria: Well, the fact that we were able to, when I joined the company was sub-$10 million, probably doing around $5 million the year before in revenue, and two years later we were on a run-rate of over $50 million and we’re taking the company public. In fact, we were a “Massachusetts IPO of the Year” in 1998. It’s tough to go from $5 million to $50 million in two years, particularly when you’re doing legacy system transformation.

I think even tougher, was this whole positioning challenge, and so we were very pleased with the progress we were able to generate in that company in a relatively short period of time. I give tremendous credit to the engineers in the company because even though we’re a consulting company, we took a very technology-leveraged approach to that business. We built a toolset that enabled us to scope these projects more accurately than competitors could and to deliver them on a more timely basis than competitors could, and that’s a huge differentiator.

Andrew: When you say that sales grew, my sense was that you were a big reason why sales grew. In fact, as I said, I did a bunch of research on you, and even back at Sheeva I saw an old press release that said, we’ve opened up new distribution, new channels, as a result of Maria’s work. You’re the person; if I understand this right – especially back then, who was able to bring in more money, bring in more sales to a business?

Maria: I certainly led that charge. Part of my success, certainly in my career, is I’ve had the good fortune to hire and work with some incredible people. It’s never just one person. I’ve been part of a lot of successful companies. You can never point to one person and say, that person made this company. It truly is about the fact that if you’ve got passion and a vision for the business, and you’re working hard, you’re able to attract like- minded people who also have a passion for the business and are also working hard, and are incredibly smart. If you’re all working well together you’re probably going to make that company pretty successful.

Andrew: So how do you find people who share your passion for this? I can’t imagine that there are too many kids growing up who say, “I want to run a legacy transformation sales business.” You’ve got to find those people who have some interest and get them more excited. How do you do that?

Maria: Well today that would not be a business that would attract my attention, for instance.

Andrew: But back then, how did you find these people who were passionate, and get them even more passionate about this business that is hard to explain to your family what you’re doing, and it’s hard to explain to others what the business is about?

Maria: A couple of things: one, the executive team there was probably the smartest and most cohesive that I’ve ever worked with in my entire career, so that was contagious. To a person, people were bringing in people; A’s attract A’s, so we just had a group of people in that company that were unparalleled. It was also an interesting time. It was a very competitive time to try to bring top talent into a company. We had a terrific head of HR there; she was incredibly creative. She’d put billboards up all over Boston. We did these career fairs, we would raffle off BMW’s.

This was 1999, you were competing with all kinds of dot-com companies for talent, and we weren’t a dot-com company, so we had to really go the extra mile. I think in return, what we got were people who weren’t easily swayed by marketing, but were smart enough to look behind it and see real company, real profits, real growth. So we attracted not only the best and the brightest from a technology perspective, but also people who could connect the dots and say, the stock in this company is probably going to be worth a lot more than the stock in Petfood.com or whatever the dot-com [inaudible] was.

Andrew: I see. You were able to let them know this is a real company. When you put your sales energy, when you put all your energy in this business, you’re going to end up with shares in something substantive instead of putting all your energy in something that’s going to go away, ala pets.com or Cosmo, etc.

Maria: Exactly. And every person on the management team had been successful previously in terms of being a part of a company that went public, being founder of a company that went public, there was a lot of success that was already built into the [??] team.

Andrew: I imagine that some people in my audience have no interest in this space, but are still listening because they have a passion for business and sales. I want to hook them back into this interview by telling them one of your proudest sales stories from i-Cube. What’s one story that you can share with us that will show us how you closed a sale that made you feel like, ‘Yeah, we’re on top of the world here.’

Maria: The one sale that we took the company public on, I’ll never forget. We were selling a Y2K transformation project to the city of Columbus, Ohio.

Selling to a city government is quite complex, because not only do you have all the people who have to operate the system and don’t want anything to change, but you’re ultimately dealing with deputies, the mayor, and ultimately you’ve got to sell the city council, who might not have ever touched a piece of technology in their lives. It’s very complex and there are lots of different gates where you can fail along the way.

We were competing with much larger companies than ourselves, technology behemoths that have two letter or three letter acronyms associated with their names.

We were doing well, and then we hit a bump at one point. I had formed a close relationship with the top business decision maker, the number two guy to the mayor in charge of technology. He metaphorically put his arm around me and said, “You know, we’re going to have to go with the bigger guys.” I said, “Despite the fact that you believe in us more, that you like us more, that there is an obvious, visual, palpable difference between the team we put in front of you, and the other team that you’ve only heard about and never seen.” And he said, “That’s correct.”

I could have walked away, saying, “We get it, that’s stinks, but we’ll hold our head up high because we didn’t lose because of us, we lost because of them. We’re just smaller and there’s nothing we can do about it.”

Instead, I walked out of his office, turned around and walked back in. I said, ‘I need to ask you a couple more questions.” We then proceeded to have a four hour conversation, in which I kept saying to him, “What is it that you’re concerned about? What is it about our size that concerns you?”

Ultimately, what we fleshed out was his issue was the way we arranged the project plan. We didn’t have enough risk up front, it was more in the back. That’s what was making them think they’d be better off with a big company, because if we had missed some dates along the way, the big company could throw 1,000 people at it. We only had 150 people in our company at that point.

When we finally figured out that that’s what the concern was, if we missed there would be no recovering, and they’d have this Y2K problem, I said, ‘Let’s address that by flipping the project on it’s head. Let’s put the tough stuff up front. Let’s take all these tasks we would normally do in the back and get them done up front. You’ll actually have great confidence and still a year and a half to figure out if we’re going to fail.’

In that case, that made all the difference. We were able to turn the thing around and get the win. Three months later, we took the company public. That would’ve been a big loss for us, it would have delayed our IPO, and there was a lot at stake.

Andrew: I’m going to ask about the IPO in a moment, but first I need to learn, where do you learn to do that? When the average person hears a no, they walk away. When we hear this kind of no after putting all the effort in, we say let’s go somewhere else or try something different or find another customer. Where did you learn to go right back in that room?

Maria: I think it was growing up with fairly strict parents who were saying no more than they were saying yes. It’s constantly justifying why I should go here or there. I had a two year old brother that was able to do a lot more things than I was able to do. Maybe it was just not settling for no all along, and when it matters, what have you got to lose?

Andrew: What you have to lose is face, or be embarrassed. You don’t feel any of that? No? The IPO, what did it feel like the day you went public?

Maria: It was great. I’ll never forget it. At Shiva, I was stuck out in Las Vegas at a trade show, and I was going to visit some friends in Tahoe. I got stuck in a snowstorm in Tahoe and watched the Sheeva ticker go across the MSNBC ticker on TV in a dirtbag, fleabag hotel room two miles away from the Lake Tahoe airport, which I was really happy to have, by the way, because you couldn’t find a hotel room at that point because of the snow, and it’s just a magical moment. I mean it’s hard to describe.

The same thing with i-Cube. You never forget where you are. You never forget everything that went into it and you take that sort of one day and you just sort of revel in it. Then the next day, you’re back to work and you remind everybody that if they spend more time focusing on the price of the stock rather than the business of the business and the customers, that they’re not going to like what happens to the price of the stock. You move on, right?

Your IPO is a one day event, in my opinion. You’ve got to get over it. You’re not as good as the market tells you are when they’re telling you that you’re incredible, and you’re never as bad as the market tells you you are when the market is telling you you’re pretty bad. You’ve just got to focus on your business after that.

Andrew: How did your life change after the IPO? This time, I couldn’t find the right numbers, but I can see that you owned a substantial amount of i-Cube. How did your life change?

Maria: So, one of the nice things about an IPO, if you are in the good fortune of having been in the company early, is, pretty much, after that, you sort of own your own destiny. You get to kind of really decide everyday, “Do you want to get up and do you want to be going to work and do you want to be doing what you’re doing?” And I think for me, it only made that whole experience that much richer.

Andrew: What do you mean?

Maria: Well, when you actually decide where to choose to spend your time, and that you’re choosing to spend your time with something that you’re really passionate about and that you really enjoy, it doesn’t feel like work. And when you’re working at something that doesn’t feel like work, you get much better at it. When you’re working at something you don’t particularly enjoy, you’re not very good at it. So, I think when you can start to blend things that you enjoy about your life and spending time with the things that ultimately become part of your profession and your work, that’s the ultimate.

Andrew: You say “much better at it” after you don’t have to do it, when you get to choose to do it. You were already doing incredible work. You already helped the company go public by nailing a key sale. What happens when you get much better at this business?

Maria: The fly-wheel starts to spin, right? I mean, when you’re doing something you love to do, you’re thinking about it a lot. You’re spending time on it. It all accrues to the benefit of the business. Your natural passion and energy for it is contagious, so you’re able to hire people that pick and choose where they want to work. If you’re hiring A players, you’re going to be far more successful because the people that they hire are also going to be A players. So it really becomes a very virtuous circle.

But let me be really clear about this, right? I have never considered myself qualified for any job I’ve ever had, since the day I got out of school. I’ve been in the right place at the right time. I was given extraordinary opportunities always beyond where I felt my capabilities were. So I just had the good fortune of working for people who just pushed me into things that I probably would not have self-identified as, “This is the next job I want. This is the job I deserve. This is the job I’m ready for.” Never thought [inaudible] for any job I ever had. That paranoia was really good for me. Because I went into every job, including this one, thinking, “I can’t do that.”

Andrew: Can you give me an example of early on, when you were pushed to do something that you wouldn’t have recognized you had the ability to jump into?

Maria: So that was my first job out of school. I graduated a semester early just purely to save some money. I was looking, I was going to on to law school. I was looking for a job for a semester and a summer. After three weeks at home, all my friends were still at school, I got really bored. I picked up the paper one morning and I answered an ad for a guy who was looking for customer service help for a computer and software retail franchise headquarters that he had just started. He had just sold his first couple of franchises and basically became, sort of, a number two jack-of-all-trades person.

We built the thing up to a couple hundred store chain, for its day, and everything that he ever told me to go do, “Go build a distribution business. Go merchandise these stores. Go figure out what inventory we have to put in them. Go start a national advertising campaign. Go build a catalog. Go rake in a couple million bucks in market development dollars.” I didn’t even know what these words meant and basically, they were on my to-do list within the first 90 days of being with that company.

Long story short, I spent five years there. I must have said to him 100 times in the first 100 days, “I don’t know. I’m not qualified to do this. I don’t know what I’m doing. I’m 20 years old. You need to hire somebody who actually knows what the heck they are doing.” And he was very instrumental in my career because he kept saying to me, “Look, IBM just shipped the first personal computer 11 months ago. Who knows about micro computing than you do? Just go figure it out. And so, it was a total trial by fire experience. I stayed there five years; I learned a ton.

And then, I got recruited away and up to Boston by one of our big vendors, which was Lotus. I joined there because a guy that had called on me when we were distributing a lot of Lotus products, a fellow named Woody Benson, said to me, “We want to do some things differently, and you’ve actually always been a fairly vocal critic of our company and have told us what we were doing wrong and how these other vendors you were dealing with were much easier to work with. And we want to do some things differently. We want people to break glass. We’re only going to bring in people this year who break glass. We want you to be one of those.” And I thought that was really cool.

So, I joined there. I had a great two year run at Lotus. He left and went to this little startup called Sheeva and called me up and said, “You need to come here” and I said, “No, I don’t. I’ve got your job. I’ve got your office. Life is great. You’re not here”, and three weeks later I was there, and I’m terrific with that. I owe the people that I have worked for who have pushed me and pulled me into these jobs a lot.

Andrew: Your first business was Software City?

Maria: Correct.

Andrew: I want to learn how you learn so quickly. Can you give me an example of one of the things you did there that you weren’t prepared for? I wrote down: go start a catalog; learn merchandising; learn how to put together inventory. I couldn’t even write fast enough as you were giving a list of all the things you had to figure out from scratch. Can you give me one of those areas that you had to figure from scratch and show me how you go about figuring it out?

I want to know: does Maria Cirino go and ask everybody she could? Does she go to the library back then or the Internet today to do all the research she could? Does she have some other method? Does she screw up at first and then let the world correct her? What’s your process? Give me one example so I could see the process play out, if you could.

Maria: The process has changed a lot over time. Today in my job I do a lot more research than I did in the first 20 years of my career. But, no, back then it wasn’t about research. It wasn’t about reading. It wasn’t about learning. It was learning on the job. It was baptism by fire. And for me, it was being fearless and recognizing that anything I broke I could probably fix. I’ll give you a great example.

Andrew: Please.

Maria: The year I was asked to do this catalog. We had all these vendors. We had a couple hundred stores. Everybody wanted their merchandise in our stores. I remember Scott Cook, the founder of Intuit, flying himself around in a Cessna 172 and coming into my little office, holding up this package of Quicken. I’m sitting there now all of 21 and saying to him, “No, that’s not going to sell. That package is terrible, worst package I’ve ever seen.

I reached into my drawer and pulled out his principal competitor which at the time was a product called “Managing Your Money” by Andrew Tobias. “Look at this package. This is a package, silver, flashy”, blah, blah, blah. So, when you have given bad advice at 21 years of age to people like Scott Cook who founded Intuit, you’ve got some chutzpah.

So, these vendors were all trying to get these products into the stores, and they would pay us money to help them do that and help them merchandise them for our franchisees and then obviously to the consumers that would come into the stores.

And so, putting this catalog together, I thought it was a great idea, started to do it, got ads from all the vendors, and we were really excited about it. It was a huge money maker. The franchisees were all excited about it, and I had sold the back cover of the catalog to a computer company called AST. I don’t know if you remember AST; you’re too young. I was waiting for their ad. I was waiting for their ad. It was holding us up from going to print. We had all the other ads. The book was ready to go.

I’m calling these people, screaming and yelling, saying “You’ve got to FedEx the thing in here. You’re holding up our whole thing”, blah, blah. Finally, the film shows up. Great. The AST ad is here, the book is complete. Get it off to the printer, and two weeks later, three weeks later, the books start to come back, and we had printed up hundreds of thousands of these things.

This was a good-sized catalog, and I’ll never forget the warehouse guy, who was a friend of mine. He came into my office. He was white, white as a ghost, and he’s holding the book. He’s holding the front cover of the book toward me, and he’s like, “You need to look at this.” And I was like, “Oh, it’s here. This is great. I can’t wait to see it.” And he hands me the book, and as I go to reach for it, he turns it around.

And there’s the big AST ad on the back cover of our hundreds of thousands of catalogs which have been, by the way, drop shipped to all of our franchisees. And there’s the Business Land logo on the bottom of the page, one of our principal competitors. We were Software City. We competed against Business Land and Egghead Software and, and, and. In my desire to get the book done, wrap that film and everything else I never looked at the ad that came in, and they had used the same ad in one of our competitor’s catalogs. It was a defining moment for me, because here we were so proud of this book, and it was such a huge success, and now it had this enormous problem. I will never forget the feeling in the pit of my stomach.

I will never forget having to go in and tell my boss that it happened; but, within 30 minutes, I was like “OK, what are all the possible solutions for this thing?” We can’t afford to throw them all out and reprint them, we are going to get stickers that stick on the back of these things, and our logo will be on the sticker. If you peel it off, you will never see the Business Land thing behind it. That was our solution. Nobody died, and that was a really important lesson for me as well, because in the first 27 of those 30 minutes, I was reacting as if people had died. I think you come to a point in your career when you realize that there is life and there’s work, and hopefully people aren’t losing their lives at work.

Andrew: How do you snap back so quickly, within half-an-hour, to be able to say I have a solution is tough. Most of us would beat ourselves up over the first half-hour, the first day, or maybe for the rest of our lives this would be in the back of our heads–we screwed up once and now we are going to triple check everything and we are going to actually freeze because of our insecurity that stems from this one incident. How did you, like that, come up with a solution?

Maria: I was busy.

Andrew: You were what?

Maria: I was busy. I had a lot more work to do that day. This was a very fast paced environment and we had to just solve the problem and move on.

Andrew: I see. If you don’t have time to indulge your insecurities, if you don’t have time to indulge your second and third thoughts, or beat yourself up, you aren’t going to. You are going to move on.

Maria: I am an optimist. Look, we solved the problem, it’s not perfect, but it’s good enough. It will get the job done. How many people are going to look at that catalog and perseverate on that small sticker on the back of it. It’s not going to happen.

Andrew: What about the other side? You have just done something phenomenal, you have shown yourself that you can just push something out there, and if it breaks you will solve it. A lot of other people would become careless as a result of that, or think that they are supermen or women, or think that they are invincible and not pay attention to details before the produce, because they figure it will all work out. Did that happen to you?

Maria: No, what happened to me is I became the greatest proof reader on the face of the earth.

Andrew: OK.

Maria: I read every single thing that I am ever going to be associated with twice, before I ever send it to anyone. I have never had another incident like that, where there has been a mistake, a mistake in address, a spelling error, nothing. It doesn’t happen.

Andrew: You and I, before we got on here, we had some tech issues where we couldn’t hear each other and I quickly, ferociously started typing in potential solutions in the chat box with a lot of misspellings, and I realize, “This is the way I am introducing myself to Maria, through all these misspellings.” Do you look at that? Do you catch those misspellings as a result of that one incident and go, “Oh, my goodness?” What are you thinking?

Maria: No, fortunately I didn’t even notice that because I didn’t have my glasses on and I couldn’t even see what you were typing. So I didn’t even notice.

Andrew: Oh, good.

Maria: I was actually focused on your lips. I was trying to lip read what you were saying.

Andrew: I saw. You did a really good job of figuring out what I was saying. You also mentioned earlier that you need to have work and life. How do you keep the separation? How do you make sure that you have that one place that is safe; where, if everything goes to pot at work, you can still maintain a happy life outside of it?

Maria: I think it’s a couple of things. One, make sure your work is actually something you enjoy, so that it doesn’t become the thing you have to go to. You can actually incorporate it into a holistic life, it has its place, you actually enjoy doing it, you’re inspired by it, and you enjoy the people you are working with. For me, that was always very important. Two, make sure that you are happy at home. Make sure you go home to a home that you like, you are with people that you like, and you do the things that you like to do. Really take the time to focus on yourself and some of the leisure activities that are going to clear your head, so that you are not constantly thinking about one thing. I think the old adage can become “Makes Jack a dull boy.” You really need to have interests outside of your work. Always be reading something interesting. Take the time to travel. No matter how busy you are, pick your head up and realize there is a whole world beyond your four walls, office, company, job, or whatever.

Andrew: I want to move on to the next business, the one that you actually founded and that I did get right in the intro, Guardent. But let me ask you this. In the moment when you have to work, it’s hard to say, “I’m going to go home.” When you have a crisis going on or opportunity going on that you want to seize, it’s hard to say, “Hey, you know what, I’ve got to go pay attention to something outside of this.” Do you have any outside interests that are so fascinating, that you’re so excited about that you pull yourself away in those moments?

Maria: Sure, when you’re family needs you, that’s where you need to be. And it doesn’t mean that you can’t get back to your crisis four hours later, five hours later, and you know, once you’ve dealt with whatever needs to be dealt with at home. And I think, you know, for me when it’s not about where you work, right, it’s about bringing yourselves to the job, and that can be whether it’s at home. It’s about taking responsibility. And if you’re taking responsibility for the job, you don’t have to show up at the office. You just have to get the job done. How you do it, when you do it is really up to the individual. And I think the most successful people figure out a way to incorporate that. And it’s never about the hours that you’ve punched in. It’s about the responsibility overall that you take for getting that job done. And it’s about being where you need to be when you need to be there. And, you know right, great people never need to ask their boss, “Do I need to be there?” They know when they need to be there.

Andrew: So how do you explain what Guardent does? And in fact, I’ve got an explanation here from CRN magazine. But again, I think you could do a much better job than all the research I have in front of me of explaining what the business is.

Maria: So Guardent was a pretty earlier pioneer in the information security space, broadly defined. And very simply, what we did was we built a monitoring and management facility, not unlike what ADP does for your home alarms, right where they’re constantly kind of monitoring what’s going on in your home alarm system. We basically built that analogue for what was going on in large organizations’ network security infrastructures.

So, in the ’90s companies went out and they bought firewalls and intrusion detection systems to protect their network. They installed these things, and the equipment functioned as advertised and it was spitting out lots and lots of data. But what the companies figured out is, we don’t really have the people to be analyzing the data to then tell us we have to turn off this port and tweak this and basically administer the equipment and optimize the equipment so that it’s protecting you in the way you had intended it to protect you.

And so it was this whole analysis and management component associated with this equipment that was just sort of not happening within these large companies. And so we essentially built that, and we were able to remotely monitor and manage what was going on in large companies’ security infrastructures. And we built a lot of technology that enabled us to do that on an automated basis. We provided a lot of reporting so that people could look smart to their bosses and to their boards and say, “Hey, “look at us. Look at all the stuff that we avoided this month. And by the way, we’re a big bank and this is us compared to our other big bank cohorts, not by name, but on a customer de-attributed basis.”

And so we started to give them a relative picture of their own security posture relative to other companies their size, other companies in their geography, other companies in their industry. And that became really important because you can under spend in security and overspend in security. And so this notion of relativity is really, really important. Plus, we built it as kind of a learning platform. So the more you see, the more you know is Moore’s law playing out in full force and effect. And so we were able to see malicious incidents and attacks coming sooner than the organizations that were looking at their own networks only could see them because we had the benefit of looking at thousands of networks at one time.

So it became like the Center of Disease Control for viruses and malicious activities. And that became a very, very powerful model. And the majority of Fortune companies today outsource their network security infrastructures to manage security services providers. And we were really only probably the second or third one to exist back in that early-2000 time frame.

Andrew: Within seven months of launching I saw that you had 25 clients, including Fortune 50 companies and government agencies. You had offices in Boston, London, Toronto, Minneapolis, San Francisco, Washington. Let’s start off with how you got all those clients. How did you get so many clients so quickly?

Maria: Well, a couple things. One, we grew too fast. This was, you know, late-’99, early-2000. The first board meeting, my board was saying to me, “You’re too focused on profits and revenue. You need to be focused on acquiring people and opening offices. This is a land-grab for talent here. Blah, blah, blah.” A year later, it was, “Why are you talking to us about PR? Talk to us about POs. When are we going to bring some revenue into this business?”

So some of it was a little bit of a silent touch, but we also had the good fortune of acquiring a couple of companies early on that came with some great security experts and a couple of key customers. For a young company to be able to get off the gate early with security and key customers, that helped us get a whole bunch of other key customers early on. Again, it was more luck and timing than strategic [??].

Andrew: At that point, you were the entrepreneur, you were the CEO. How was life different as the woman in charge of the whole business, of the face of the company, after having run so many other people’s businesses?

Maria: It was a huge eye-opener for me. I always held the revenue responsibility for most of the companies that I worked for, and I thought that was a big responsibility.

Andrew: It was.

Maria: I thought that I’d be well prepared. When you run revenue, what else is there, really, right? There’s everything else. There’s every little spat between your executive team members, you’re adjudicating battle after battle. There’s cultural issues. There’s all kinds of stuff. It was a real eye-opener, and I think, in addition, that in that period of time, 2001, 2002, it was a tough, tough time to be building a company, right? 9/11, we lost an employee to 9/11. A huge hit for a small company.

Three years later, we lost three employees who were out in the [??] fire. This is stuff that, even if there was a CEO school, they don’t prepare you for it in CEO school. It’s the time, during your darkest days, is when you learn the most about yourself. That’s when you learn the most about the people around you. I had days, literally, where I just would lay in bed, and it would be 5:00 in the morning. It would be time to get up, and I would just pull the covers over my head, and say, “I just don’t want to do it. I can’t face it.”

Those are the days that you need to get up the most. You need to go in. Even if you’re not wearing a happy face, you need to go in wearing a confident face, and a calm face, and an empathetic face, and you need to pull the organization together. Our company thrived during that period of time, even though we took major hits, like I just described. Even though we were battling enormous heavyweights, just in terms of the economy overall, and I think one of the reasons that we did so well, is that people in our company really did pull together. To whatever degree that, as a leader, I was able to help facilitate that, that was probably my proudest moment.

Andrew: Do you ever feel like a fraud when you don’t want to wake up in the morning, when you want to just put the covers on over your head, and instead, you go into work, and you have to be beaming, confident, projecting that you guys are going to win at the end of the day? Do you ever feel like, ‘Well if this thing all falls apart, everyone will know that I’ve been lying up until now, or think that I’ve been lying up until now?’ Not too many people, I think, is the reason why they don’t project that confidence.

Maria: I couldn’t do that. That would make me feel fraudulent. I couldn’t have a morning where I could hardly get out of bed, and then go into the office and be beaming. I couldn’t do that. What I could do is go in, stand up in front of everybody, and say, “I had a really tough time getting out of bed this morning. I have a feeling I know exactly how you guys are feeling. These are the toughest times I think we’ll ever face, not only in this company, but probably in our entire careers. What we do over the next 30 days, or over the next 90 days, to pull ourselves out of this, and to pull our company out of this, will be the most defining moments for most of us in our career.

By the way, what we do day to day is really important. Think about the organizations who are counting on us to help them prevent issues and problems that could take planes out of the air, could lock up pharmaceutical transactions. There’s a real impact, and effect with everything that we do.” We had amazing customers, utilities, government plans, so it was an opportunity for us to take a step back and remember that the work that we were doing, in terms of protecting [??] infrastructure was fundamentally [??].

Andrew: I’m actually imagining that there are people who might be going through what you went through. I’m imagining they’re going through it right now, as they’re listening to this, and they’re rewinding that section, just so that they can remember it when they go back into work tomorrow. In fact, let’s put a finer point on it. If someone is going through that tough moment right now, maybe they were avoiding work while listening to you, because they’re trying to get themselves pumped to go back in, what do you say to them? How can they get back in the game?

Maria: Well, I think it’s about being honest and being authentic. And not necessarily putting on the happy face, if it’s not a happy time. But, pulling together. And that’s either pulling your team together, or going to your boss and saying ‘I’m really having a tough time. I could use some help’. But it starts with honesty. And it starts with being situationally aware enough to kind of know whether or not you’re bringing your A game, or whether or not you have an impact to help other people bring their A game, and work that you need to do. And so, I think it’s about honesty. It’s about communication. And it’s about never giving up. It’s perseverance. Success in entrepreneurship, success in your career- it’s really all about perseverance.

Andrew: All right. I’ve got two other questions about this business, and then I’d like to move on to where you are today to catch people up. The first is, you said ‘we thrived’. How do you thrive in such a tough environment?

Maria: Well, as I said, individuals in the company, and the company itself found something that we didn’t even know was there. And people started working much better together.

Andrew: But I mean, companies were cutting back, going out of business, laying each other off. I forget which company it was- I remember reading a story in the Wall Street Journal at the time about a person who said, ‘I had to fire someone. And then a few hours later, I was gone from the business myself.’ And that’s the environment that you were in- companies, government agencies, were cutting back, and here you were trying to sell something to them.

Maria: So the key- key for us was, we were selling something to them that, if they bought it, was actually going to potentially save them money. Because trying to do this themselves was actually a more costly proposition than outsourcing it to us. So we actually did have a good-value proposition that had a counter-cyclical advantage to it in a down economy.

And two, we were really good at it. And we were able to demonstrate how good at it we were. And we were able to say things like, “Hey, we saw Melissa virus, I Love You virus, XYZ, at 2:14 Tuesday morning. When did you see it?” And it became our mantra to sort of hold up [??], and sort of say, ‘look, if you’re seeing these things hours later, days later than we’re seeing them, chances are you’re being affected by them. If you’re being affected by them it’s costing you hundreds of thousands if not millions of dollars’. And so, of course it’s going to be cheaper to not be affected by them. And so ultimately that became a pretty powerful weapon for us.

Andrew: [??] by the way that I haven’t heard you speak anywhere before. You’re fantastic. You’re one of my favorite guests.

Maria: You’re a great interviewer.

Andrew: Thank you. I appreciate it.

Maria: You make it easy.

Andrew: Thanks. So, final question on this business is: why did you sell?

Maria: That’s a great question. And, first of all, it was a very good offer. At the time, the company was probably on a run rate of about 25 million bucks in revenue. So, to be able to sell the company for a 145 million bucks, with a half cash, half stock transaction, [??] stock was at a multi-year low. So we felt that there was a lot of room. Which it turned out there was. The stock more than doubled in the subsequent 18 months after they bought us. So it looked like it was going to be a really good transaction for all the shareholders, particularly all the employees involved.

Secondly, the business that we were in was starting to grow up a bit. And one of our principal competitors had already been acquired by a big security company. And we lost our first deal to a big financial services company that said to me, “You’re the best in the business, your reporting was the best, your stock is the best, your people are the smartest- we’re going with the other guys because they’re bigger. Now, what I’ve told them is, if they’re not where you are 6 months from now, we will be their most celebrated win and their toughest loss, all in the same year.” The company that he told that to was [??]. And they came back 6 months later and bought us. So it was a loss at the time, but it actually sort of became a win. And, it was just the way the industry was going. And today, you don’t find small MSSP’s. They’ve all been absorbed into big companies. Sometimes you have to read the tea leaves and realize that if you’re doing everything right, and you’re still going to lose to a big company because when it becomes part of an infrastructure fabric- big companies are just more comfortable buying from big companies- then you need to know when the right time is.

Andrew: I remember Wayne [??] selling his company, Blockbuster to Viacom at the perfect time. I mean, today we know that Blockbuster and videos and DVD rentals aren’t what they were. And even though he knew it was the right decision, and he was going to profit significantly from it, he cried, I think in public with all of his employees. He told them that it was because it was such a big loss. How did it feel to you? We talked about the upside of the sale, but how did it feel to you personally to have to give up the reins?

Maria: Well, it was interesting because on the one hand, I really like Lotus {?}.

Andrew: You stayed with them afterwards.

Maria: Yeah. I like the strategy at the time. I loved the woman I was going to be working for. I felt like the company was going to be really well positioned. And so, that (?) about the transaction overall, and I felt there was a lot of upside and the stock which was going to make my employees a lot of money.

All that turned out to be true and great, and I don’t mind change. I love change. If you look across my entire career, every four or five years I did something completely different. It was always technology, but it was a very different piece of technology. I like to have to plunge myself into new things, new areas, new industries. It’s part of what makes my current job so rich for me is that every day it’s a new thing. I look at new things, learn new things, meet new smart people, and that’s what makes this job feel like a gift.

I do remember the day I announced it. I was really happy about it because I thought it was a great outcome for the company. There was lots of runway, and I’m looking at a bunch of employees in a 150 person company saying, “A year from now this person is going to be running a division in Paris if they want”, or “This person can go do this”. Like, all these opportunities are going to open up that might have opened up for us, that might have opened up for them at the time if they stayed with Guardent. It could have taken years and years so this is going to accelerate advancement and professional opportunities for a lot of people.

People came to me with tears in their eyes saying, “How could you do this?” When I explained how and why and the risk associated with not selling, and the way I looked at it in terms of “Look at all these opportunities for you guys”, it turned around like that. So, on the one hand it’s very gratifying for people to say, “I love this place. I love the people work with. I don’t want anything to change” but on the other hand it didn’t take long for people to celebrate what a great opportunity it was going to be.

A bunch of people put a bunch of money in the bank, and that always feels good, too. A lot of those people, by the way, are still together in that business. It subsequently got purchased and purchased, and now it’s Dell’s Managed Security Services business. I’ll argue it’s the best managed security services business in the world because I still know most of the people running it.

I think it’s amazing. Here are these people . . . some of them have been together doing the same work for 11 years. In technology, that says a lot.

Andrew: Yeah. All right. I want to find out about where you are right now. Just give me a moment to check the connection to the microphone on my side. It’s looking OK, but I’ll be right back.

There was a time on MTV where they would have that big “Sorry we’re having technical difficulties with picture. We’ll be right back.” Today, of course, it’s just a relic of the past. I wonder if we’re going to say the same thing about the Internet. There was a time when Andrew had to go and adjust his own microphone. I remember those days. Today, everyone’s got a slick setup but back then . . .

Maria: I wonder what’s the time we’re going to get to first when we say, “Remember when cell phone calls used to drop all the time?”

Andrew: Right. I wonder if we’ll ever get to that point. I think we might even get to a point where we say, “Remember when people used to make cell phone calls”, like what? You can’t type, I’ll be right there? You have to call me up and tell me. Who knows?

Why did you decide to become a venture capitalist about two years after selling the business?

Maria: Again, it wasn’t my idea. I came out of Verisign, and I was on the receiving end of a lot of interest from VCs here in Boston who were saying things to me like, “Hey, we focus on security as part of what we do here. We want you to help us look at deals. Come in. Get to know some of the partners. Start networking with a bunch of interesting security people that you know. Bring them to us.

I actually helped start another company at that time called Verico (?) which is in our portfolio today, which is a terrific security company. I really enjoyed doing that. I loved meeting with the entrepreneurs, but the firms that I was doing this with and for were quite large. I just felt that if I wanted to do this for the rest of my career and I started to get interest and offers from these firms, hey, join us. Why don’t you join us full-time?

I think true to my entrepreneurial roots once I had realized that I had fallen in love with the work, I wanted to go test the waters and see if I could actually start a firm rather than join a firm because once you start something that’s what you want to do. So, I had the good fortune to team with a former colleague from i-Cube, Larry Begley, who was our CFO when I was there running sales and marketing. He introduced me to a VC that he had worked with the previous few years, and they had a close working relationship named Donohue who’s our third partner. That’s when we started talking about forming 406.

Andrew: What does 406 mean?

Maria: So, 406 was Ted Williams’ batting average. Ted Williams was a famous Red Sox baseball player, and he batted 406 in 1941. And it’s never been beaten since. The reason that Ted was able to hit so precisely was that – I’m going to use a visual aid here – he had extraordinary eyesight, and he wrote a book called, “The Science of Hitting”. Can you see the card that I’m holding up?

Andrew: Yes. It’s on the back of your business card?

Maria: On the back of my card. If you can see these little dots within the strike zone . . .

Andrew: Yeah.

Maria: So this is (?) and Ted wouldn’t just hit anywhere within the strike zone as most batters do, he would only hit in certain areas that he knew he could hit the best. And so, he was a very selective hitter. As a result of being so selective and having such good vision, he achieved a batting average that hasn’t been beaten since.

We felt it was a terrific metaphor for this business because we look at a thousand deals a year, and we fund five or six, as most venture funds do. And so, it’s a business of selectivity, and it’s a business where you need to apply some vision, and a URL was available for eight bucks. We didn’t have to pay up for it.

I want to give credit for our founding associate, Kara Sweeney, who came up with that. We sent her home on a Friday, and we said, “Don’t come back to work until we have a name, and it has to have a Boston flavor, and it has to be metaphorically connected to what we do.” I think she nailed it.

Andrew: Yeah. Absolutely. That explains, too, why there’s a point 406 before it. We’re talking about a batting average. What’s your small sliver of the batter’s box of it. What is it called again? What did I just miss the word? Strike Zone, excuse me. What’s your small sliver of the Strike Zone that you have to hit?

Maria: So, we’re incredibly focused here at 406. We start out typically by telling people what we don’t do. We won’t invest in consumer internet, social media, mobile, gaming, that’s not us. What we are is enterprise IT properly defined, and within that we have some specialties. Mine is not, surprisingly, information security, and a slice of infrastructure related visual media.

My partner, Lynn, focuses on IT health care and a slice of energy IT. Our partner, Larry, focuses on infrastructure IT, and so we’re very, very focused. One of the reasons that we’re so focused on these areas is that because we’ve lived in them as entrepreneurs and as operators we’re good at it. And we know good technology and differentiated technology in those areas when we see it.

We have an incredible network that we can bring to bear to help us vet ideas and technologies to help us become important first customers for these ideas and technologies, to help us form strategic relationships, to potentially come and run these companies or be part of executive teams in these companies. And so, we’re using all the assets that we have and that we’ve developed over 20 plus year operating careers, and that accrues to the benefit of our companies and ultimately, of course, to our investors.

Andrew: How do you get to know the new entrepreneurs in the Boston community?

Maria: A couple of things. One, we’ve been around now on the scene for five or six years. I’m really proud of the reputation that we’ve developed. Entrepreneurs today are so much more sophisticated about picking their VCs and their venture partners than they ever were, certainly when I was taking money. And they have great mechanisms with which to share that information.

There’s a site called The Funded where entrepreneurs talk to each other, and they rate their experiences with VCs. This is unheard of, and we’re exceptionally highly rated on sites like that. And we have a very good reputation because when people come in here they know that there’s a slim chance that they’re going to walk out with money, but what they’re also looking for is advice, some respect.

We’re not on our Blackberrys doing the whole meeting or at any part of the meeting. Meetings start on time; meetings end on time. We’re supportive. We’re friendly. We’re approachable, and unfortunately that’s all too rare in this business.

So, we have a lot of people who have come to us because they say, so and so said that he met with you or she met with you six months ago. They had an incredible experience. I’d love to come in and talk with you about my technology, my idea, that sort of thing. And so, that’s probably the biggest one, that’s the biggest area and the one that we’re most pleased with.

And then, it’s the companies we’ve invested in, the entrepreneurs we’ve invested in. They are also a huge lead source for us, and again that’s part of how we rate ourselves. At the end of every year and certainly as we look back on the fund cycle, once the fund cycle has been completed. If we’re doing the right thing by our entrepreneurs and the operating executives that we put into these companies, we’re the first person that they think about when somebody comes to them and says, “I need a recommendation or a referral to a VC”.

So, that’s very positive, and then I think we’re out and about in the community. We’re frequently asked to speak and present on panels at entrepreneurial events and watering holes. We sponsor a bunch of cool parties. We’ve got a terrific team here, Greg Dracon, who you’ve met briefly who was solving our tech issues, and Graham Brooks are active and engaged in a ton of entrepreneurial events on campuses. Graham actually started a really cool program for us called The Student Fellows Program, where we actually have .406 fellows on campuses, on about 16 different campuses. They meet as a group, generally on the phone or through Skype every other week. They talk about deals that they’ve found on campuses. They come here a couple of times a year for meetings.

Andrew: And these are students who are fellows?

Maria: These are undergraduate students for the most part, a couple of MBAs.

Andrew: OK.

Maria: And the criteria for the program is that you have to be exceptionally entrepreneurially-minded and you have to have already started at least one business. So this is an incredible group of people.

Andrew: So you’ve got entrepreneurs who are already on campus, who’ve started businesses, who are now helping you identify other entrepreneurs on campus who you should get to know. I see. By the way, I’ve got the “The Funded” here for .406 Ventures and I see, “decent, thoughtful, had a couple good meetings, they passed due to us being too early, but would definitely meet them again,” and “.406 invested in my company and sits on my board, so I have worked closely with them. These folks are the real deal. They are smart, perceptive and offer great operational support,” and so on. So you do get a lot of high marks here. Can you give me an example of advice you’ve given an entrepreneur based on your experience, or any advice that’s helped them act differently than they would have if they hadn’t met you.

Maria: Sure. We invested in three young guys probably close to three years ago, now. They were terrific. They were your classic entrepreneurs: early twenties, monster-smart, obviously not a ton of commercial experience, right, because they’re 20, but a great idea, and had already developed at least a demonstrable prototype for a really interesting technology. And we loved them. We wanted to fund them. We found them in Texas. We basically said to them, “You’ve got to move to Boston or New York.” They picked New York and we set about working with them.

And one of the introductions that we made to them lead to a company called Etsy coming to them, which Etsy is the largest marketplace online for handmade goods, and saying we thought they’d be a terrific partner for the company. And they basically after a couple of meetings said, “We need to own this thing. This technology is amazing. It could make a huge difference in terms of enhancing Etsy’s search capabilities.”

And the guys came to us and said, “Hey, they want to buy us. You know all we have is school debt and credit card loans and this looks pretty good to us.” And we said, “Look, you know you’ve got a really promising future ahead of you. We’re not going to get in your way,” even though we could because we actually had a blocking right in our documents with them. But we said, “Don’t worry about that. Let’s not focus on that. Let’s focus on what’s going to get you the most value. And we think what’s going to get you the most value is: say no a couple of times, keep your head down, keep growing the business. And we did enough research on you, enough diligence on you, we know they’re not going to find anything like you anytime soon. And if they really want you they’ll come back.” And so they did that.

And the offer kept going up, and up, and up. And finally they came to us and they said, “We can’t take it anymore. You need to take this over. You need to go work with them. You need to go say no. You need to go negotiate with them.” And so we worked together very effectively with that. And ultimately we did a deal, several months later. It was three times larger than the deal that they would have taken. And I think they learned a lot from that, in terms of a little patience can go a long way. You’ve got to continue to believe what you’re doing. You have to have the guts to say no and good things can happen.

Andrew: You mentioned that these entrepreneurs picked New York over Boston. I’m seeing that New York is overtaking Boston and D.C. in venture capital deals. Why? What’s happening in Boston?

Maria: Well, I mean when you say overtaking, right, I mean these sort of numeric indicators that change from quarter-to-quarter, I don’t know how much stock you can put in those. The reality is, I think that from a trend perspective ad-tech is pretty hot right now and big data is pretty hot. And New York happens to be a great market to start companies in both of those spaces.

And so if we were going to invest in an ad-tech company today, and in fact the anecdote I just described to you was an ad-tech company and that’s why we said to them, “You’ve got to be in Boston or New York.” And I think they wisely chose New York. So entrepreneurs who are focused on certain areas now are seeking out that market. By the same token, for the stuff that we do here, health care I. T., information security, infrastructure I. T., Boston has always been one of the strongest markets for those types of businesses and in particular security talent, amazing security talent here, right, coming out of EMCRSA and cell phones and a bunch of other interesting security companies so for the stuff we do we actually think our geography is an advantage.

We don’t get hung up on who does X number of deals, one little known fact is that of all the venture capital that flowed into company’s in New England last year more than 45% of it was imported from the West Coast, so anybody that wants to say there isn’t enough going on, there isn’t enough entrepreneurial activity here in Boston, simply not the case. The West Coast guys are making sure that their money gets planted in a bunch of activity here so there’s no shortage of activity here it’s just that I think it depends on how you define yourself as a part and if you’re an Ad Tech big data defines fund, you probably should be in New York not Boston.

If you are a consumer internet, mainly focus funder, a game focused fund, you probably should be focused out on the Valley but if you do what we do it you’re probably focused exactly in the right place if you’re in Boston.

Andrew: All right, let me make a quick plug here and then I’ll ask you one final question that I’ve been wanting to ask you but first the plug is this guys if you’re enjoying this interview and want to go to the next level with me, go to Mixergy.com/premium where we have courses lead by past Mixergy interviewees including Oren Klaff who not only shows you how he’s raised money for the companies that he’s raised money for, but he shows you the actual pitch stats and he shows you the whole process he’s gone through and Stella Fayman of FeeFighters shows you how FeeFighters gets so much publicity by walking you through the process that they take step by step so check out Mixergy.com/premium, if you’re already a member you have access to all of those courses, if you’re not I hope you go to the next level with me and sign up.

The final question is this, what do you miss most about being the CEO of one company?

Maria: So there’s a magic that happens early on in these companies and it’s really a cultural thing and it’s the recognition that you’ve started something together, everyday you’re experiencing you’re trial stipulations and victories and often times company’s start in one room, right? The living room, your kitchen, one little office and ad jump to your venture, you’re firms office, something like that [??]. I’ve started companies in all of those venues and you look around that room and all of a sudden what started with two of you or three of you or four of you, there’s now 15 of you or there’s now 50 of you in that one room and the ventures room is saying, ‘You have to get out, right, you’re eating us out of house and home.’, but there’s magic, there’s absolute magic to that.

And being able to, as a leader, get up in front of that group in good times and in bad, as we talked about earlier, and inspire and calm and create excitement and enthusiasm is really special and that’s not this business. This business is being able to find brilliant, forward thinking entrepreneurs and team with them and give them the capital and hopefully some advice to get them going and that’s really special too.

So people always say to me, ‘Well which one do you like better?’, and I loved doing what I did in my operating career but I was ready for a change and this was exactly the right change and I wouldn’t give this up for anything in the world because it is probably the most special job you could ever have because entrepreneurs are the most special people that you could ever work with and so it’s a real gift but I feel incredibly fortunate to have had both sides of the court.

Andrew: I feel incredible fortunate that you would come in here and do this interview with us … I’m hearing a little bit of an echo and bare the echoes with me and deal with the mic issues and I really appreciate all of this and I know my audience does too. If they want to find a way to say thank you to you what’s the best way for them to connect with you, maybe see you at one of the watering holes where you’re sponsoring drinks, what’s the best way for them to come by and say, ‘Thanks for doing this interview and good to meet you.’

Maria: They can hit our site, all of our emails are on the site and we’re one of the most approachable people on the face of the planet. I get about 500 emails a day so sometimes it takes me a little while to get back to you but most of the time it’s within a day or two but emails the best. Occasionally you’ll catch me in my office on the phones, I noticed it rang about five times during this interview which I apologize for but I think we’re very approachable and want to talk to people who have great ideas and I thank you, you’re a terrific interviewer and you’re doing great things for entrepreneurs so keep it up.

Andrew: Well, thank you so much, thank you for doing this interview, thank you all for watching and of course guys the company is 406Ventures, Maria, it’s great to meet you.

Maria: Thank you, Andrew.

Andrew: Thank you.

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