How I Selected My New Gig

Continuing on in the honesty and transparency theme - and hoping this will also prove to be useful for other entrepreneurs - I figured I'd follow up my "what did I learn from OneTrueFan" post with a new bit of sharing.

I recently took a new job with another start-up (the amazing AppFog team). How I got to this decision might be valuable to others.

After the OneTrueFan acquisition and my departure, I found myself at loose ends. Most everyone was telling me to take some time off. Some of the investors in OneTrueFan (thanks Rob!) immediately mentioned other portfolio companies they wanted to introduce me to. A bunch of former clients of mine reached out to see if I wanted to get back into consulting.

Given all the advice, and my exhaustion, I decided I'd take some time off. I scheduled a real vacation (for the first time in a while). But, honestly, every day that went by I felt more pressure. I couldn't identify the pressure - but I felt it and it was increasing.

And then one day I had lunch with Joe Schoendorf and he shared an incredible insight. He pointed out that - for people like me - nothing is more frightening (and dangerous) than boredom. Given this, he suggested I not take time off and not take my time looking for a new gig and not start consulting again. In other words, he told me the opposite of what everyone else was telling me.

And he was right.

For me, nothing is worse than being bored. And when I get bored, bad things happen. When I get really bored - if someone comes along with an opportunity that is dumb and doomed to fail (but won't be boring - at least for a little while) I am likely to take it out of desperation.

As soon as I accepted this - I felt the pressure decrease.

I decided my highest priority was to draw as wide a net as possible and evaluate as many opportunities as I could as quickly as possible. This - alone - made me far less bored. In fact, I found myself as busy as when I'd been employed!

First I decided to determine what kind of company I wanted to work for. This was easy. Going with my "boredom is my jabberwock" theory, I wanted the least boring kind of company. In other words, a start up (and an early stage one at that). Cool. I contacted all the various investors and entrepreneurs I knew and told them I was looking to join a new start up.

Second I decided what mattered to me in a job. For me this ended up being a pretty simple short list. Most important was the team. Were these people I wanted to work with? Would I enjoy myself around them? Would they push me - and support me? Could I learn - and teach? Second most important was my role (NOT my title). Was this a role where I could make a real, material difference for the company? Was it a role I could be successful in? Was it a role that I would find boring? Third (and last) in my list was Odds of Success. How good were the odds that this could be a win? And how big (in what timeframe)?

Third I looked at constraints in my decision making. I knew I wasn't going to leave San Francisco, so that was a big constraint. I knew that there was a minimum salary that I could accept (cost of living). I didn't want to work in a business that was dependent on Publishers for revenue. I didn't want to travel too much.

Along the way, many people gave me advice.

I'll be honest... 90% of it was wrong. This is perhaps my biggest piece of advice from this process. Listen to everyone - question everything they say. Each of us are not like the others. Do not assume that just because you want to go about this differently that you are wrong. In general, the best advice came from VCs. The worst advice came from recruiters. You really have to trust your gut here.

That said... if everyone is telling you to do one thing, you better be really sure that your gut isn't lying to you if you want to do something else. I kept hearing two pieces of advice that I disagreed with.

First - everyone told me "you need to be more clear on what you want to do and what job you want." Personally, I despise the way hiring occurs and think hiring should be for talent and ability first and foremost (not pegs into holes bullshit). So I dug my heels in and said, "no, I'm doing this my way."

I was wrong. You need to have a clear and cogent story for what kind of a job you want and why you want it and what excites you. That's just reality. Fighting against this is no-win. Move on.

Second - everyone told me "make sure you get a title that will make sense on your resume." Again... I think this is a symptom of the idiotic and failure-prone way we hire (or at least the way HR has trained us to hire). And again I resisted and decided to do it my way.

And I believe I was right. Focusing on title and all the artifacts and HR cruft surrounding the actual job would have resulted in my not taking the AppFog job. And I am very confident that would have been a huge mistake.

So in the end, I've ended up running marketing (a shift in my often broader focus which means I will be unlikely to be bored), for an early stage start up (again, unlikely to bore me), with an incredible team and amazing investors (who I want to work with, respect, and like), building a product that has amazing traction already and truly shocking potential (high odds of success).

I'm incredibly excited about this.

So, to sum up my lessons learned:

• if you're an entrepreneur you likely don't handle boredom well. Accept that and work with it instead of trying to act like something you're not.
• volume and velocity are vital in your decision-making. Get a lot of leads and eliminate quickly. Be decisive. If you find one that resonates in your gut... hustle. Fight. Chase. Win.
• work your connections in the VC world and the entrepreneurial world. Only use recruiters if you don't have a good network.
• write down what you're looking for and what would make you happy in a job. Prioritize. Simplify. Test against this (and be honest).
• listen to all the advice you get -- but trust your gut.

Ironically, in the end my decision was really cemented for me by three things.

Every investor I talked to (regardless of whether or not they were investors in AppFog) told me how impressed they were by the AppFog team in general and by Lucas (founder and CEO) in particular. That's a really good sign to look for.

The major AppFog partners I talked to were both very positive and excited -- and quite cagey. Again... a very good sign.

Most of all, however, I spent a day with the entire team. And it just felt right. It felt like the place I wanted to be.

So now I'm here.

Hell yeah.

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