Posted on

The Startup Thing
(History Lesson, Part III)

This week Leapfrog Online held its first Hackathon. It was the culmination of several efforts in the organization around making innovation more tangible, and demonstrating the capabilities of unfettered time to build. We had 14 teams, with well over three-quarters of the company participating, and every single one of the teams’ projects was green-lighted. It was, in the words of our CEO, an “unqualified success.”

We tried something different, and it worked. And the things it produced will add meaningful amounts of business value for our teams, our company and our clients. You can read our blog post on the corporate site for that part. It’s meaningful, but there’s a deeper story.

MinutemenI’m a veteran of the dot-com era, which for me started in the mid-90s. I had a friend at CERN, and a friend at the National Center for Supercomputing Applications. I was in a PhD program at the University of Minnesota1 studying the political economy of technology. The friend at CERN would send both of us stuff about what Tim Berners-Lee was hacking on from time-to-time. Evenually, the friend at NCSA called me up in Minneapolis to try to get me to come back to Chicago to work for this company he was starting up. That friend was Alex Zoghlin and that company was Neoglyphics, the first real Web consulting firm in Chicago.2 I declined, but ended up coming back to Chicago anyway, when my proto-dissertation about how the Internet was going to radically change our socio-economic order was viewed with amused skepticism.

That was the summer of 1995. I started doing freelance Web consulting.3 and was shortly recruited by Playboy Enterprises to begin what would become Playboy Online. Alongside some early experiments from the New York Times, the Chicago Tribune and others, we built one of the earliest online magazines, and definitely one of the first major subscription revenue-model Web sites.

When I was at Playboy, we shared something…special. And it wasn’t about the content, or the brand, or the vibe provided by Hef.4 It was about the people. Most of us came from a variety of semi-related pre-Internet disciplines. Writers. Designers. Nerds. Musicians. Journalists. Theater people. There was only one real software engineer who had formal training. We were all the developer, all the sysadmin, all the UX person, and whatever else was required. We did our best, and it mostly worked.

And it was intriguing that it actually worked, because not only were there no clear guidelines about *how* to do something, but there were also no clear guidelines on even *what* you should do. Various generations of imported management made assertions. Various generations of salespeople from big and small software and consulting firms made more vague, PowerPoint-based assertions. But when it came down to cases, we just had to make it up. More precisely, we thought about it, tried something, and then iterated. There was less a sense of hierarchy, less a sense of rigidity, and more a spirit of adventure in the face of adversity and uncertainty. We made it up as we went along, and it was Good.5

This feeling will be familiar to anyone who has participated in a startup. In fact, every day is like this in a startup. It’s an adventure. There’s a lot of fear and anxiety. There’s a lot of exultation. There’s a lot of crushing loss. It’s not really for the faint-hearted, and if it’s not like that, then maybe you’re not doing it right, or it’s not doing it right for you.

In between the time I left Playboy and started at Leapfrog Online, I did two startups. One of these, Edventions, was started by someone who knew about executing on big ideas. Irv Shapiro’s idea was ahead of its time, an intranet/extranet system in a box, with hardware, software and networking for K-8 school. It was a fantastic idea, but the educational system was not ready for it yet. What made it great was that the Thing I experienced at Playboy was there. And it wasn’t just Irv himself, who was the first CEO I worked with that embodied the Thing, but a meaningful portion of the whole company. They believed in what we were doing, which hadn’t been done before, and it was Good.

I went elsewhere after Edventions was sold, and the Thing was totally gone. Not even part of the scene. I learned to sell, inside and outside. And then I did another start-up. This one was mine. And the horrible part was this: I didn’t create the Thing. I was so worried about the product, the next client, and not going broke that I didn’t even consider it. Terrible.

But when I sold the intellectual property from that startup to Leapfrog Online, the fact that I had been missing the Thing—not even *considering* it as important—came back in an instant. Smart people trying to do something that hadn’t been done before. And real value was being created.

Where was the Thing?

When I arrived at Leapfrog, I began pining for it. The Thing would show up in fits and starts, sometimes in big ways, sometimes in small ways, but it’s much harder to maintain that feeling—which certainly existed during LFO’s startup phase—when you get to medium size. Mid-size companies have unique leadership, strategy and talent challenges, and they’re all about scale and growth.6 Rapid change, but the kind of change that cannot be as nimble as that of a start-up, because the company has different things to prove to its founders and investors and clients. The pressures are different and the solutions to them are about maintaining focus while building out more specialized functions. Not the most conducive to that elusive startup Thing, or so I thought.

Until this week.

I have been trying to recapture that feeling, what it was like at Playboy back in the day, for a long, long time. And during the Hackathon, I felt it. It was glorious. But that was not the best part. The best part was at the *end* of the Hackathon, when I had a chance to sit down and talk with the people I had stayed up all night with, and who really, really got a lot out of it. I realized that THEY felt a Thing—not my Playboy thing—but their *own* version of that class of thing that they could look back on and say “I felt that and I *did* that.” I realized I wasn’t really trying re-create that feeling for myself. What I *was* trying to do was to create it for THEM. And that is really what I’ve been striving for all this time.

So. Pretty please, with sugar on top. Do a Hackathon at your company. Even if you’re not a startup.

  1. Home of Gopher. [↩]
  2. Started with his dad, Gil Zoghlin, whose then-ultra bleeding edge color laser printer we utilized for various nefarious purposes back in high school. [↩]
  3. You had to know sysadmin stuff. You had to know Perl, which was really the only viable language other than C to do stuff in, and you had to have some knowledge of visual design. But most importantly, you had to explain the crazy notion that the “World Wide Web” was critical to the future viability of a mid-size insurance company. Not easy. [↩]
  4. Though producing several live pay-per-view Webcasts from the Playboy mansion certainly delivered its share of amusing anecdotes. [↩]
  5. That it actually worked, to the benefit of the parent company, seemed almost but not quite secondary. [↩]
  6. A point worthy of explanation here, since the challenges of mid-size companies, relative to startups and big corporations, do not get discussed as much in the Internet world. [↩]
Posted on

Mid-Sized Company Growth, Specialists, Loss of Context and the Television Pilot Conversation from Pulp Fiction

When working with specialists, context is everything.

When I ran a startup, I tended to gravitate towards and hire people with a multi-disciplinary focus. I liked hiring people that wrote code but also understood interaction design. I wanted people who liked managing clients but were also obsessed with data. I liked hiring visual designers who understood marketing strategy. Those sorts of generalists are critical in a start-up, because you don’t have the capital or time to develop a wide variety of specialist functions. You pick your single area of focus and make big investments there, but rely on generalists for the non-core functions. I also think that generalists are more comfortable in the dynamic environment a start-up provides.1

When your company gets to be mid-sized, things change. You’re not quite big enough to have full-on specialist functions throughout the organization, but you’re too big to have a team consisting largely of utility players. People who were once all-in-one coders, testers, and project managers start to move up the food chain and get more focused. And in certain areas of the business where the possibility of eking out some competitive advantage exists, specialists begin to accumulate. This is entirely natural, but it has consequences.

As groups of specialists—more accurately, specialist functions—emerge, there is a concomitant loss of context. Groups of people begin to form who just do data analysis, or just do functional testing, or just write RFPs. If you hire correctly, they begin to do these things really well. But because there’s specialization, and because there’s less organic messiness in the way decisions get made, and just because there are more people, there’s a natural predilection towards increasing the efficiency of the individual specialized function. That team of search engine optimization gods look at each other and say, earnestly, “Let’s do this right. And with the best of intentions, the organization as a whole starts to optimize for its constituent parts instead of the complete entity.

I want to reiterate that this is a natural outcome of the growth process in companies. I’ve seen it happen again and again. It’s nobody’s fault. It is, however, everyone’s responsibility to mitigate the problem. And I’m not a big believer in large, overarching organizational methodologies as a panacea. Be simple and tactical, and develop a distributed solution to the problem. So while you can expect some additional writing on the dangers of over-specialization in future posts, I want to offer here one simple, tactical suggestion that anyone, at any level of your organization, can use to defeat the Context-Loss-from-Specialization problem.

When you’re working with someone who has a very specific type of knowledge and experience, you have to provide them with an easy way to unpack their thinking from the (otherwise useful) blinders imposed by their specialization. The best way to do this is a conversation, and the name for the special kind of conversation I’ve found to be the most effective in this situation is a Television Pilot Conversation.

This is a reference to a scene in Quentin Tarantino’s film, Pulp Fiction. Check it out:

The Television Pilot Conversation has two purposes, one relatively straightforward, and the other constituted by an ulterior motive. The straightforward purpose is to clearly and succinctly describe the context for the person lacking context. The more sneaky and sub-textual purpose is to remind that person that there are actual other humans out there operating with completely different sets of considerations, familiar with entire bodies of knowledge and experience, possessing skills equally as important or impressive as theirs, that should be taken into account. Now.

Television Pilot Conversations may take place on a one-to-one basis, or in large groups. The more deadpan the delivery (Samuel L. Jackson being the ideal to strive for here), the better. The more use of humor or irony, the better. The more familiar the person on the receiving end is with this particular scene in Pulp Fiction, the better. Here’s a convenient short URL for your distribution pleasure:

http://bit.ly/tvpilot  

The beauty of the Television Pilot Conversation is that anyone in the organization can deliver it to anyone else. It knows no bureaucratic strictures. It transcends seniority, hierarchy, and age. It requires no internal branding campaign, no corporate communications, no brown bag session, no long, boring meeting. It’s context in its most concentrated form, with a format guaranteed to generate results.

Enjoy.

  1. Frankly, I just plain like being around people who mix their chocolate and peanut-butter. Amongst even the most highly specialized people, an intense second interest—cf. correlation between superb software engineers that are also talented musicians—is often a good indicator of robust capabilities elsewhere. [↩]