Interview: Scott Weiss, IronPort's CEO

"Ready for lunch?" My conversation with IronPort's vice-president of technology, Patrick Peterson, comes to a sudden halt. Co-founder Scott Weiss has put his head round the door, and it is clear that, ready or not, it's time for lunch - my interview with him begins and that with Peterson comes to an abrupt end.

"I'm Scott Weiss, the CEO," he says, eyes fixing mine, his hand giving the firmest of shakes. You get the impression this guy is no shrinking wallflower. That intense gaze is not just for introductions. As I soon discover, it's part of the Weiss experience. It could be described as unnerving - if you were in any kind of negotiation, I'm sure it's a great weapon.

He rushes me out of the IronPort building listing the lunch options: "Chinese, Mexican, diner". I plump for diner - assuming it's a kind of burger-type affair. You get the feeling that Weiss is not the sit-down lunch sort of guy most days. We walk out to his canary-yellow Porsche Boxster - it sits in the company car park, as dazzling as the Californian sun this November morning.

We buzz a few blocks along El Camino Real until we reach a nondescript-looking diner called JoAnn's. "You'll love this place," he says, grinning. The diner is small, full and very noisy. The walls are covered in photos and random American memorabilia. Taking our seats in the booth, I notice that, bizarrely, just in view over Weiss's left shoulder is a framed picture of a British Spitfire. It seems appropriate, somehow.

We order. To combat the noise, Weiss grabs my recorder and, in the manner of an excited sports commentator, responds to my shouted questions. I get the feeling he likes to be in command. He has form in the Valley. He was with Hotmail when it had just 12 employees. And, according to his official biography, it was his time there that helped him identify the emerging business opportunity that would later evolve into IronPort Systems.

Before that could happen, however, he served some time at tech incubator Idealab as managing director and entrepreneur in residence, where he met fellow IronPort-founder Scott Banister. His CV also boasts stints at EDS and McKinsey, as well as an MBA from Harvard.

He mulls over his time with the bigger fish of the tech world. "I do have a natural bias against large companies," he admits. "They're bureaucratic, they're slow and they can't make decisions. If we brainstorm large companies versus small companies, we could come up with ten reasons against the large company."

But now, obviously, IronPort is part of a very large company, Cisco. You sense that Weiss was initially uncomfortable with the change, but he claims to see benefits in it now. "I have to be cautious of that bias as I'm within Cisco as a leader. I'm constantly challenging myself when I do that, because at the end of the day, Cisco is a very well-run large company," he says. Weiss is obviously not about to slag off his new paymasters, but he's refreshingly open about the pros and cons of living with uncle Cisco.

"The balance we want to strike is how to get all the benefits of being part of a big company without any of the negatives. The downsides could be being told: 'We no longer need your sales force because we have 16,000 salespeople at Cisco.' But they are not trained to sell advanced security products, whereas mine are.

"Our customers rely on us for being Johnny and Jane on the spot - when they call in, they don't want someone saying: 'Which Cisco product do you use?' There's a level of understanding and a connectedness in our customer support ecosystem that's never going to go away because of the nature of our products."

Cisco paid Ironport the compliment, probably for sound business reason, of allowing it to remain autonomous - not something all its acquisitions have enjoyed. "It's not separate for the sake of it. We might become a sub-brand or a Cisco brand at some point," Weiss cautions. He points out that Scientific Atlanta and Linksys, also part of the Cisco empire, have lost their autonomy. The difference is, he insists, that they are consumer brands. "We're an enterprise brand - that means something to enterprises."

I look at the Spitfire once more and venture that perhaps their benefactor is not the most loved of IT corporations - in fact it's right up there with Microsoft in the knocking stakes. It's big and dominant, lacks innovation and people - particularly its rivals - don't like it. What's Weiss's view?

"I think Cisco has a surprisingly good reputation for such a large company. I'd compare them with General Electric in that regard. It's managed to sidestep the monopolistic accusations that Microsoft has been painted with because it competes on the merits of its products. I've never read in the press that someone has questioned Cisco's motives with the same veracity as they do Microsoft's," he insists. Instead, the view is wholly positive. A good-guy image. A great brand for such a large company. There are always sour grapes.

Weiss makes another point about the Cisco way. It refers to a "Leadership Offsite" with Cisco CEO John Chambers a few months ago. There were 3,500 people there, Weiss recalls. "At my Leadership Offsite, there's maybe 12 people, and we get a whiteboard and brainstorm, but that's very different. I'm sure John has his senior staff meeting, and there's 12 people too; but with 60,000 employees you need to communicate a message, at least annually, to your top leadership, which means 3,500 people.

"When I first walked into this leadership summit I felt like Alice in Wonderland. You know, there are 3,500 people, this huge facility, some of the meetings were piped in via circuit TV. I was completely out of my element," he admits. "But they had each of the senior executives make a presentation. They were tight, the messages were clear, and they had external speakers, such as Lee Scott, the CEO of Wal-Mart, who spoke for an hour and a half about leadership.

"When I got back to my hotel room, I thought, if I was running a 60,000-person company, I would have done the same thing. I don't know if I would have pulled it off quite as eloquently as John Chambers did," he continues.

Well, OK, but what else was different? After all, big companies put on big shows, they can afford to. What else did he take away? Weiss neglects his lunch, grabs the recorder once more and fixes me with that stare.

"Something we do naturally at IronPort is care about our people. We created a culture at IronPort of people speaking up and feeling comfortable doing that. An open-door policy, people raising things to you as the CEO." He claims that, to his surprise, he found the same kind of approachability from Chambers and his executive team. "I feel I made a good choice when we decided to sell the company to Cisco. You know, these people are my employees. I started this firm when there was just me and my co-founders. I know every single person by name. The values at Cisco are the same ones I subscribe to," he says.

It's all still very new, the acquisition and the adjustment to it, but those values come from somewhere, and one suspects that Weiss will keep them. He's learned them. He worked for McKinsey, an experience he has fond memories of and that taught him the value of looking after people. He likens his time at McKinsey to a medical internship - watching the procedures but not being allowed to wield the knife. It was frustrating for an ambitious young man in 1996. "The internet was happening, Yahoo had just gone public - I told McKinsey that I wanted to get a job in technology."

What happened next taught him a lesson in business and people management. "McKinsey has this thing where they treat you well on your way out. Most companies are just, 'well off with you then'." To his surprise, the company even gave him a research assistant to help him find a job in Silicon Valley. The reasoning is that McKinsey people, once established, will tend to hire McKinsey people back - like IBM under Gerstner's rule - McKinseyites everywhere, he says. A nice line in perpetuity.

So began a period of intense interviewing - it seems he was grilling them as much as the other way round. Some interesting propositions and at least one lucky escape were involved. "I was going to be the head of business development at PointCast (the star of 1996) - thank God I didn't take that job. I was going to be the first man at woman.com, the first straight man at PlanetOut, had offers at Xcite - but what really intrigued me was a little company called Hotmail," he remembers.

After that blossomed, he went off to Idealab, which was then causing a sensation in the Valley. "It was going to be the biggest IPO ever. It raised a billion dollars in the private markets. Jack Welch had just joined their board; the first board he had ever joined. We were all counting our money when the train went off the rails," he says.

"I learned a lot. I think being part of Hotmail, which was an incredible success, and Idealab, which went off the track pretty hard, I got the best of a success and a failure.

"And having my own failed start up inbetween, I don't think my experience is atypical. I think most leaders in Silicon Valley have to have a few failures on their resumes, in order for a venture capitalist to put money into you," he muses. "You have to know what it feels like for the boat to be sinking. Because many times, people who have never felt it don't know, and the boat sinks."

So what would he say makes a good technology entrepreneur, apart from learning how fail? "I think number one, above all else, is to surround yourself with a great team. Because, at the end of the day, the idea, the concept, takes a lot of twists and turns, and you have to have smart people in every function. And, yes, learn how to fail."

He reels off all the business attributes that a successful tech entrepreneur needs: multi-facing, multi-tasking, the obvious ability to sell, the company, the product, getting investment ("the value of a company with no cash: zero") and being able to sustain the energy.

But what about technical knowledge? Can the chief executive of an information security business get away with not understanding the product? His speech on the business of entrepreneurship seemed to suggest that it was not so important. But he must have some understanding? "So I do," he says, between mouthfuls of chicken. He mentions his time at technology services giant EDS, when he had to go through the company's technical school.

"You have to know enough to know when things are going wrong. I'm glad I have that experience but, truth be told, great technology companies have the right mix of sales and marketing and technology prowess," he elaborates. "The hill is littered with great technologies that were never marketed correctly."

We muse on the culture of Silicon Valley. Weiss is a closet romantic. In his eyes, Silicon Valley is the modern equivalent of Renaissance Florence or Impressionist Paris: a place where like-minded people from all over the world are irresistibly drawn to and thrive.

Remembering my taxi ride from San Francisco airport the previous evening, this line of thought doesn't seem all that far-fetched. Famous names flashed by on the way to Palo Alto, home of Xerox Parc, Stanford University, and the famous garage belonging to Mr Hewlett and Mr Packard.

An entire ecosystem has been created around technology start-ups - the finance, the recruitment, as well as the engineers. The model has been recreated around America and the world - Bangalore is turning into an Indian version. But Weiss thinks that the dominance of Silicon Valley may be on the wane, citing Thomas L Friedman's book The World is Flat, which foresees a new era of rapid entrepreneurialism fostered on and by the internet.

"I think Silicon Valley is going to become less of a nexus. You could now be smart and in the middle of nowhere, but through the internet your brains will rise to the top," he suggests.

Lunch over, we head back to the car. Weiss insists there's time for more questions on the short run back to IronPort's San Bruno base. I ask about spam.

"Will we ever be able to break the back of spammers? No, it's just too lucrative," Weiss admits. "We will continue to fight the good fight and keep spam to levels where it's just an irritant. Many customers have no idea of the amount of time and effort and brainpower that goes into fighting this."

I get one product exclusive. The Cisco brand is likely to be used on an IronPort product targeted at the SME market. "You will see announcements that we're moving aggressively into that space, only because now we've got the product and the brand to go and prosecute that," he says.

He stops the car just outside IronPort's building to drop me off. We are out of time. Weiss has meetings and is heading straight out. I get out and watch the Boxster merge into traffic and fly away, car and driver equally full of energy.

ON THE SC WEBSITE

Interview: Patrick Peterson

In an online exclusive, SC editor Paul Fisher talks to IronPort's vice-president of technology, Patrick Peterson. Read his unique take on the emerging security challenges of cloud computing and Web 2.0, the difficulty of educating IronPort's customer base and how the war on cyber crime could be lost if we don't change mindset.

- www.scmagazine.com/uk/news/article/777656.