A Startup Guy and His Tale of Recovery

By March 24, 2010Uncategorized

I’m a startup guy. I didn’t know that until I was already neck-deep in a startup, but it’s true. I often get asked why Glue’s sponsors are so dominated by startups. Partially that’s because guys like Techweb (producers of Cloud Connect) have “national account” reps for the big guys; folks that can pick up a phone and talk to the VP recently put in charge of the new cloud computing initiative at big software vendor X. That’s not me. Where they can land the big 50, 100, 150 thousand dollar sponsorships, it takes me months just to get put on Oracle’s budget planning for 2011 (ie, next year). And that’s cool. I’m not complaining. Because the other side of why Glue’s sponsors are dominated by startups is that I’m a startup guy, and Glue is a startup, and really — I just love the energy of startups.

All of that said, I was walking the dog (our golden) this morning, reflecting a bit on the 5 years since I left the last software startup I was involved in. And I thought I’d blog a bit about it. It’s not exactly “on topic” for Gluecon, but I figured what the f&#ck — I’m a startup guy.

Let me start at the ending– namely, what I have I done since leaving Ping Identity (the startup in this story; disclosure – I still have equity in Ping). In July 2005 (when I left), I began working as a contractor for IDG (the company that bought Digital ID World — the identity management conference I helped start), wherein I worked on shows like Syndicate (an RSS/feed show that was ahead of it’s time and went under) and LinuxWorld. I also started (inside of IDG) a show called SaaScon, which now runs under the Computerworld brand. After leaving my IDG contractor position, I started Defrag (now entering year 4 of existence) with my old biz partner Phil Becker and the guys from Foundry Group. That went so well that we started Glue. And Glue’s gone so well that we’re looking at a third show (Blur), and I’ve got one other fourth, super top-secret project in the hopper that I’m not discussing – yet.

Sounds like a lot, doesn’t it? Here’s the thing: From July 2005 until January 2010, I really took it easy. I was very careful not to take on too much. When we started Defrag, it felt exhausting. When we added Glue, it felt exhausting. And then, what seemed like very suddenly, in December of 2009, I started waking up in the morning with this overwhelming sense that I wanted to (needed to?) do more. An energy level was coming back that I hadn’t experienced since 2003-04. I’ve since doubled my workload, and I feel great. And it’s only upon reflection that I now know why.

I met Andre Durand in early 2002 (I think it was January 18th, or something like that). We’d been introduced by Doc Searls (of Linux Journal and Cluetrain Manifesto fame). Doc told me there was this guy who started Jabber that was doing some “security” thing for the internet, and I should meet him. I did. Andre went on to tell me about his vision for Digital Identity — which sounded suspiciously like Single Sign On to me. I thanked him, yawned and went home.

I woke up a couple of evenings later in the middle of the night in a cold sweat. I couldn’t STOP thinking about identity and the internet. I saw it in everything. It had completely consumed my thoughts. So, I did what any sensible startup guy (didn’t know it yet, remember?) does — I called Andre up and asked if I could work on this with him — for free. He, of course, said yes, and we were off.

We worked *constantly*. Round the clock. We didn’t even have any idea what we were doing, we were just obsessed. In a few weeks, there was actually the semblance of a company idea that Andre thought he could raise money around, and seeing that I was basically not sleeping (in lieu of working), he offered to pay me *something* from the small angel raise he had done. With one caveat — the money ran out in October (it was march or april). That was the wall – so we set off to raise money.

And we did. And then we did again (a Series A). And then we got offices, and employees, and policies, and an executive team, and (oh shit) CUSTOMERS, and revenue and — it was amazing. But from 2002 until July of 2005, when I stepped away, Ping Identity was my complete and total obsession. I used to have a contest with the main guy that worked for me (Steve Nakata) about who could show up to the office earlier. When it was all said and done, Steve and I were regularly meeting each other at the door between 5:30-6:00am — with a smile on our face. Ninety hour work weeks were common-place and “life balance” was for people who didn’t really have the dedication we did.

What I never realized in that intoxicating, high energy, hyper-aggressive (somewhere in there I bought a doberman and a sports car) atmosphere was exactly how exhausted I was.

When we sold Digital ID World in 2005, Ping was raising its C round. Things had gotten pretty bureaucratic, and my “screaming in the hallways” style wasn’t as….appropriate. (Yes, I really did scream in the hallways, and throw things in my office, and just generally cause havoc.) I left, and my then girlfriend and I moved to a beach in Florida.

At first after leaving, I really thought something was physically wrong with me. I felt like I was coming down with the world’s worst hangover. I couldn’t sleep. I didn’t eat. I really enjoyed laying on the beach and cocktails. After about six months, I realized it for what it was — some kind of post-startup depression, which I think was inspired by pure exhaustion. I was still working at the time, but at nowhere near the pace I’d held for years (nor the intensity). Oh – and I found myself *constantly* frustrated by working with people inside of a large organization — it was like these people were there for their *salary* or something (not the “vision” of what we were doing).

From 2005 until 2009, I slowly added work components back into my life. But the whole time there was this sense that my tank was always running on fumes. After the first Defrag, I literally slept for 2-3 WEEKS. It took everything out of me. By comparison, now when I finish a conference, I sleep for a solid day and plan to take a vacation for the 7-10 days following that (which is much different than sleeping for 2 weeks).

In any case, my startup exhaustion appears to have lasted about 3.5-4 years. I don’t know if that’s common. I don’t know if I’m an odd bird. But it is what it is. I do know this — suddenly, I’m coming out of that exhaustion, and it feels like someone lit a fire in my belly. I’m starting all of these new work things, and I can feel that old vibe: the more work I take on, the more energized I get. Pure, unadulterated, nitro-like passion.

Am I repeating the same mistake? Eh — first off, I never saw it as a mistake. Secondly, I’d like to think I’ve learned a lot about how to manage my own rhythms, needs, etc. And, frankly, I’m older – I just wear out faster.

But still, I’m a startup guy. Nothing gets me up in the morning like thinking I get to work on things with startups; to build a new “industry”; to break some new ground. And, to be fair, I know a TON of people that perform those jobs inside of big companies like Cisco, Facebook, Microsoft, Oracle.

In the end, I know this: Startup guys (and I mean “guys” to include “gals”) feel this nearly unquenchable obsessive fire around their startups. It can lead to all kinds of errors (failing too slow), and personal harm, and general badness. It can also be the most satisfying thing you ever can do in your work-life. I have some life-balance now. I’m married. I’m trying to lose some weight. I walk my dogs around the island. I still go out for cocktails and drive a sports car. But I’m a startup guy.

The other day, I was at a hospital picking up some X-rays for my wife, and someone asked me if I was an employee there. I almost took offense. Seriously? Me? Work here? Really? Uhhhh…that’s not what I do. I’m a startup guy.

Anyway — that’s my little morning reflection on being a startup guy and my tale of recovery. Cheers. 😉

P.S. I’d be remiss if I didn’t remind everyone that early bird pricing for Glue expires on April 2nd — REGISTER NOW.