Buzz Pressure

Communal Twitter stream by Defrag twits

http://twitter.com/defrag/with_friends

Day 2 of Defrag is starting and if it comes close to the experience yesterday it should be an awesome day.

Brad has a post up on his (Feld) thoughts on how Day 1 went. Jeff Nolan has an awesome Twitter stream going or at least he did yesterday.

The one thing I haven’t seen is a commentary on the quality of the crowd. There’s only about 250 people here but suffice to say that if lunch is a bit dodgy and the potato salad happens to take everyone down, this industry would take a major hit.

I’m going to miss someone important, but the people who built what the internet is today and those who are building what the internet will be tomorrow are all here. The thought leaders, the VCs who funded the crazies, — all here.

The huge plus is that you can’t grab coffee (I grab a lot) without bumping into someone important and interesting. For example, Ilya and I had a chance to chat casually with Esther Dyson while milling around the breakfast buffet this morning.

Many kudos to Eric Norlin for pulling this thing off.

UPDATE: the Closed Private announcement has resulted in Kevin Marks of Google showing up to talk Open Social today.

Darling you gotta let me know
Should I stay or should I go?
If you say that you are mine
I’ll be here ’til the end of time
So you got to let me know
Should I stay or should I go?

I’m writing this on a plane en route to Defrag. Less then 48 hours ago I worked for an entirely different company. In fact in the past 14 months I’ve worked for 3 different startups and quit two of them. Yeah I’m a catch.

Always tease tease tease
Siempre - coqetiando y enganyando
You’re happy when I’m on my knees
Me arrodilla y esta feliz
One day is fine, next day is black
Un dias bien el otro negro
So if you want me off your back
Al rededar en tu espalda
Well come on and let me know

I’m a self confessed startup junkie, I love the chaos, the insanity of building and bringing products to market and the personalities that startups gather like moths to a flame but sometimes you need to pull the chute, jump ship, and ride a new pony (I don’t think I’m missing any metaphors).

Should I stay or should I go now?
Should I stay or should I go now?
If I go there will be trouble
An’ if I stay it will be double
So come on and let me know
This indecision’s bugging me
Esta undecision me molesta
If you don’t want me, set me free

48 hours ago I was a member of the management team of a plucky stealth startup. I obviously can’t say much about the company but suffice to say it is the proverbial “big play”. If they’re successful, and I sincerely hope they are, they’ll change the experience and utility of the web. My role there was significant in the area of architecture and I had a great team that for the most part I personally hired. Hmmn sounds pretty sweet, “So exactly how long have you been an idiot Jeff?” Funny, I think they asked the same thing.

I wish it were that simple.

The startup experience could best be described as wacky. Sometimes things click and it’s magic. For me I get that endorphin rush at the whiteboard (no really). I can feel thicker bushier dendrites forming, ok maybe not but I’ve seriously felt waves ecstasy at various moments along my ‘career’. No wonder I’m addicted or possibly chemically imbalanced.

Other times the clicking is, uh, not so much. For a while you can successfully ignore the gnaw of dissatisfaction. You need to exercise patience, probe and have conversations about what you’re feeling. Everything doesn’t necessarily have to be fireworks. Every startup is a tough schlog and if it were cut and dry it wouldn’t have been a tough decision. And that’s the motivation of posting this article — if you find yourself in the same position should you stay or go? I’ve done both and will try to shed some light on my experience. First a word of warning, I have been called a “high effort subordinate” on more then one occasion. The first time was after running up a record number of union infractions at the university I worked at, so take the following with a grain of salt.

As a certain technology association president is fond of saying, the only think more dysfunctional then a band (like say I dunno The Clash) is a technology company. I believe that to be the case regardless of size. There’s a lot that can contribute to that dysfunction, be it market pressures, the working environment but probably more then anything it is the personalities sitting around the table.

My take/experience is that once the magic dies between the people it’s tough, tough, tough to get it back. It’s not unlike friendship, dating or marriage. Sure some relationships can weather the storms; some are even made stronger by them. Those are the rare ones. If you’ve got that right now protect it for all it’s worth, you should definitely stay and not go. They don’t come along that often, trust me.

However if the magic dies and you’re certain it’s not coming back, you should go. It’s not fair to your team, the company or yourself. I also believe (apparently) that not only there isn’t shame in doing so but rather it is the honorable thing to do. I also want to say it can be done with mutual respect and dignity and I owe a big thanks to the CEO and Founder/CTO of a certain stealth company. I also owe much love and gratitude to my family for putting up with my sucking and blowing (mostly sucking) during the past couple of months. I know it hasn’t been easy.

Exactly who’m I’m supposed to be
Diga me que tengo ser
Don’t you know which clothes even fit me?
Saves que robas me queurda?
Come on and let me know
Me tienes que desir
Should I cool it or should I blow?

So that was my last week.

Prior to that company I founded a financial services SaaS company. Like any company, we had our challenges along the way but also our successes. I’m very proud of what the team has done and am still involved at the board level. However if you’ve been involved with a startup, you know that growth isn’t linear. Companies tend to grow until they reach a breaking point, under extreme duress (incriminating photos help) the CFO finally caves and green-lights the hires you needed 2 quarters ago, Rinse, Repeat.

Along the way casualties are almost universally unavoidable. The early, early folks are typically long gone either unable to deal with the “oppressive bureaucracy” a 15 person organization brings or they simply aren’t willing to submit to the rigor of “buttoned-down” process and adult supervision. As we grew I was fortunate enough to back fill my team with some A-talent. After 4 years, my role as CTO seemed superfluous, at least to me, and the company’s greatest need wasn’t vision but rather execution. Through a combination of attrition and growth we had 3 or 4 open positions that I ended up filling and like any self-respecting CTO, not particularly well.

I’m a reasonably competent strategic product manager but I’d rather wash my cornea with a rusty cheese grater then be a long term (1.5 year +) technical product manager. I’ll die and likely kill others in the process. Same goes for project management. I’m what you might call a conscientious MS Project objector. I find the presence of Gantt charts to be a sure sign that a project is doomed. It’s silly I know but you have to understand I’ve worked on projects in the aerospace industry that had project managers who managed the “real” project managers and don’t even get me started about the Program Managers.

To me software is still an art, it can be guided but you can’t manage it in the same way you can manage the building of an office tower. At least not by me and not with the kind of people I like to work with. That isn’t to suggest you can deliver software predictably. Under the guidance of a great VP Dev we never (ever) missed a release while I was there and I believe the same is true to date. But I digress.

So with that context in mind, it wasn’t entirely surprising when the gnaw began and 9 tough months later with no end in sight I finally exited for everyone’s sake. Again I’d say the same caveats apply, if your work isn’t positively affecting yourself and your team, you should go. For me, role definitely contributes to personal satisfaction and I was running on empty.

Should I stay or should I go now? Yo me frio o lo sophlo?
If I go there will be trouble - si me voy - va ver peligro
And if I stay it will be double - si me quedo es doble
So you gotta let me know - me tienes que decir
Should I stay or should I go? Yo me frio o lo sophlo

Lest you think I run off the second I’m unhappy, I want you to know it certainly isn’t the case. I exited that particular company after it had lived its’ darkest days and was in the best position it had been in more then 24 months. Similarly I literally shut the lights off at my first venture backed startup, Ardesic, after the .com fallout. I’m not a duty dodger and I’m certainly not suggesting you should be either. But if you find yourself in the wrong role with no way out or in a working relationship where the magic spark doesn’t exist and you truly, deeply believe the company will be better for your departure then you should go. If on the other hand there is light at the end of the tunnel or you can weather the storm(s) then I encourage you to stick it out even if it is “character building”.

Lastly that chemical imbalance theory might be factoring pretty high in your mind right now as you realize that I’m writing this without even officially starting day 1 of my new job. Even better at this exact second, I’m sitting across the aisle from one of the founders. He’s madly reading research papers while I talk about when to quit your job. I know it’s shocking I don’t have a career in marketing. Rest assured I did *a lot* of thinking, due dili and getting to know people before making any decisions. I was extremely fortunate to have a couple of opportunities present themselves and for whatever reason I was even more fortunate to find some guys I really like in a space I really like. We’ve only done a little bit of whiteboarding but there was definitely some of that magic I was missing. My wife can attest I haven’t been this happy in a while.