Chris Pirillo is nearly 40 but could easily pass for 20 with his boyish looks, tech savvy, and the fact that he’s pretty much spent the last two decades indoors, in front of a computer screen. But in all that time eschewing a “normal” day job, and growing up, Pirillo has become a known face of geek culture. The Midwesterner turned Seattleite is the founder of the blog and online community Lockergnome.

Last week, he teamed up with T-Mobile to be the face of its new ad campaign, in a move that acknowldeges his growing Internet celebrity.

I spoke with Pirillo via phone to get his take on building a tech career and where he thinks the industry is headed. 

RW: You’ve been in this business for a long time (founding Lockergnome in 1996 and being online since 1992). How do you build  a tech brand and how do you stay relevant?

Chris Pirillo: It’s easier and more challenging than I realized. I know it sounds kind of strange. As an independent publisher who’s bootstrapped, I do not have a full team at my disposal. So as odd as it sounds, I find myself incredibly challenged.

It’s difficult to maintain velocity when you’re fighting for attention. So as the tools become easier and easier to use, and more well-funded and well-staffed organizations are able to crank things out quicker and in a more complete fashion, you have to be wiser about how you use your resources and where you spend the greater amount of time.

I’ve done my best over the years to not just sign up for various [social media] accounts, but I’ve driven pretty hard to balance my reach between any one of the social media channels, from Twitter all the way to YouTube. And it takes time and attention away from other things but at the same time has provided a greater amount of longevity for the things that I’ve been doing. I don’t exist in any one space. 

RW: How many hours of the day are you online?

CP: All. I don’t think there’s time that I’m not online. I’m always connected. Always. I’m always connected and that to me is not even an option anymore. Not just watching trends, but also developing and really fleshing through them. My primary vehicle is video. To stay ahead, you’ve always got to be connected. And that, to me, is as much entertaining as it is part of work.

RW: What’s your work station like?

CP: Well, my work station is nice enough that some people actually replicated it. Right down to the exact desk and light configuration. It’s clean, I can tell you that. It’s as clean as it possibly can be. Clutter tends to frustrate me. I learn to live with it, but I generally keep a clean work station. I’m surrounded by any given platform so whereas a lot of my computers are Mac, largely because of build quality, and the ability to run on Linux or Windows through them. In my work environment I try to keep it as balanced as I possibly can. If only because if I’m to provide perspective I have to have experience with things. My work environment reflects that balance. Course I have fun things around the office, too. I collect Darth Vader stuff, I’m an adult fan of Lego. I have so many unopened Lego sets … I can’t keep up.

On Building A Brand

RW: For someone who is trying to build a tech brand, what is your advice to entrepreneurs who want to do something along the lines of what you’ve done?

CP: Every day is a challenge and it takes a lot of work. It doesn’t get any easier. If only because you’re facing increased competition for attention. And that I think is driven me almost to the point of madness. So, while it’s certainly a possibility for you to grow a tech brand, my primary suggestion is to really take stock at what you’re doing, what you want to do, and how you’re going to do it differently than everybody else. That may boil down to your personality and perspective. And the best medium to portray that personality and perspective, more often than not, is video. Video’s going to catapult you further than written content I feel, at this point and time. In that video if you say something that resonates and you present something that resonates with the audience it could drive your connection with them at a very deep level versus just reading words on a page. It’s not easy, it’s a flooded space. There are perspectives that one might be able to share. But, the way that you’re probably going to be standing out from the crowd is to be starting with video. The Internet is a fantastic platform for that. 

RW: How can small business owners and entrepreneurs carve out a career in the tech space?

CP: I think more and more small business owners are going to be given an opportunity to do what they do better because of the advancement of technology. Technology is as much a part of the human condition as anything else at this point. I would say there’s a greater possibility for you to be yourself and carve out a career being yourself. And for small business owners it means lowering costs instead of increasing them. Meanwhile lowering frustrations at the same time. 

RW: Where do you think the industry is going? There’s so much with social gaming and social video, there’s so many avenues, what do you feel like is a big trend that’s a little bit below the radar?

CP: I think the way the Internet is going, I think I’ve always played into it. I think it’s going to be more displayed. I think realistically, the cult of personality is a very strong driver for attention. And the more you are yourself and the more you put yourself out there, I think that adds a deep level of legitimacy to you asserting yourself. What I mean by that is we’ve gone through the whole content farm thing. The industry goes in cycles. People want to trust other people. That’s the bottom line.

So the more you are yourself, the more you’re going to make connections with other people. That’s what is going to drive everything. It’s going to drive your business, it’s going to drive your community, it’s going to drive attention. It’s very, very draining on certain things, but for a long time we’ve had the main factor of celebrity coming out of Hollywood. And I think that’s going to dissipate quickly. We’re still going to be entertained. There’s still going to be a value in quality production, but in terms of “expertise” specifically within an industry that you talk about social media, everybody has these experiences. And everybody shares these experiences whether they’re in a broad scale or a narrow scale.

There’s only so much attention you can spend, only so much attention you can give. So the value of attention you can get, is going to increase. While at the same time the amount of attention you get is going to decrease. So the more things that get thrown at you, get thrown at everybody else. Where can you stand? Where are all the values at? What are the things that no one else has? Nine times out of 10, it’s going to be psychology. It’s going to be personality. That’s a unique perspective, but people. It’s interesting to me how this industry evolved. It’s difficult to pay attention to everything. You have to be able to be your own filter or rely on filters to cut through a lot of the noise.

The Fight For Attention

RW:How do you get your news and get a feel for what’s going on and what people are talking about?

CP: I say Facebook, Google+ Twitter. And emails, too. If I don’t see it in any of those channels, it’s possible I’m not going to see it. There are a lot of outstanding apps out there that allow me to dissect information and take it all in. Which makes it more difficult from a publisher’s perspective because if no one reads it, is it really going to matter. If you pour your heart and soul into something and spend a lot of time and money on something, it isn’t going to go anywhere. I mean that on a very micro level. Even an article, if it’s so outstanding and no one sees it, because there’s so much attention put to other things, it causes me to question the validity of spending two hours on an article when you’re not even going to get the money back on the time you invested putting that out there. When the same thing could happen in a tweet, or a link.

And that is a greater challenge for content providers because the value of written content is being greatly diminished because of these platforms. The more things we have to pay attention to, the more precious our time becomes. I mean that in a business way and I mean that also in a virtual sense, because it’s almost indelibly intertwined. With everyone out there writing, creating, who’s listening? That’s the biggest hurdle I think that the industry has at this point. It becomes easier and more difficult. You cannot scale to the level of traffic that would offset those costs, you’ve got to figure out, where can you benefit in the grand scheme of things if you want to establish yourself as a pundit. Or if you want to establish yourself as someone that has a perspective or something to add that’s different from everybody else. Where’s your value in this entire chain?

RW: What are you most proud of in your career?

CP: Being still up. I’m a still-up. There’s all this talk and buzz about being a start-up and what about the still-up? I think everyday that goes by  being able to turn through downturns and shift in direction and still be able to come out ahead. I’m not funded, I’m not effectively staffed and I bootstrap everything. That I am still able to be successful in light of all these hurdles, it does make me proud to say that I can still do it. But that’s just a a part of being able to watch trends and knowing where to spend the time and attention. 

RW: How has your personal brand helped Lockergnome and vice versa?

CP: In many ways I think my name has superseded that brand (Lockergnome) for better or worse. It’s lent me amazing opportunities on either side. I reach more with my strategy, it’s definitely benefited me directly. 

Working With The Right People

RW: What would you say the hardest moment in your career was?

CP: I definitely worked with a lot of wrong individuals. There are a lot of wrong people to work with. And I seem to find a lot of them. Not to say that the people that I’m working with now are in that range at all, but that’s the biggest drain on my time and attention and resources in general. I’ve made a lot of expensive mistakes and those expensive mistakes are largely in relation to really bad partnerships. Really bad hires. 

RW: And that’s you wanting to believe in someone and it not working out?

CP: Pretty much. A lot of under-delivering and or hidden agendas. And that as a small business owner can really hurt you. It turns out I have the ability to attract people that want to be like me. And that doesn’t work. There’s only one me and that’s what helps make the business work. 

RW: What does the word “geek” mean to you?

CP: I guess for me it boils down to being yourself or being passionate. A nerd may be (able) to talk about statistics and analytics and not be tied emotionally to something. I think a geek is tied emotionally to something. That’s my separation for me. At this point it doesn’t even really have anything to do with technology either. I think the definition has evolved. 

Disconnect? No Thanks

RW: What’s a typical day like for you?

CP: On an average day, to me, not much happens. Wake up, get coffee, now I carry the camera with me everywhere I go. It’s a point and shoot mod that’s targeted to real-estate developers. It’s a super wide angle lens, so I carry this with me wherever I go. I come home usually, go to the computer and plan what I’m going to be geeking out about that day on YouTube. Sometimes I’ll have meetings throughout the day. In the afternoons YouTube videos. At night usually is when I’ll edit the blog from yesterday and upload to YouTube. Amidst all this: Emailing, responding and following up, social media and trying to get a handle on where my business is going to be next. 

RW: How do you relax?

CP: Honestly, I don’t. It is stressful. It takes a lot of work to make something look effortless. I enjoy taking a lot of information in and to me that’s relaxing. Otherwise my mind is always spinning, my mind is always thinking. I find it really difficult to disconnect. I’ve always been an information junkie.

RW: Do you have any hobbies that you do to get you disconnected?

CP: I’m an adult fan of Leggo. The problem is I just haven’t had the time. Like this has been hell week: Microsoft, Apple, Google, boom boom boom. It’s been crazy. 

RW: Any outdoorsy stuff you like to do?

CP: Hello no. I’m a great indoorsman. I did a brief video series on that, I tried years ago. I’m a great indoorsman, I can cook a marshmallow over a stove and climb the stairs. 

RW: What are you going to be for Halloweeen?

CP: I’ve got a stormtrooper uniform. Funny thing, I surprised the pizza delivery guy one day. I opened the door and he went “whoa.” Kind of taken aback. I tipped him well.