This is a guest post by Tac Anderson

I have a pretty good track record for predicting what trends will take off. I also have a pretty good record for predicting which cool new digital technologies will do well on the Web. I am horrible at predicting my own future.

A year ago if you asked me what I most likely would be doing today I’d have told you, probably doing a startup. While I was working at HP I was also the Entrepreneur in Residence here at Highway 12 Ventures. I worked with VC’s not just in the region but also across the company. Let’s just say I was in a very enviable position by any entrepreneurs stand point. While no promises were made Mark and the guys at Highway 12 Ventures were willing to fund the right idea. And if I proved the concept I had established a network of VC’s who would have been very willing to talk to me. All the doors were open, I just had to come up with the right idea.

Instead I’m working at Waggener Edstrom, a global communications agency, leading the social media initiatives for some of the biggest tech brands in the World. To some people I made the worst decision in the world, to others I made the smartest. The only thing I can tell you is that I made the right decision for me at the time.

To help you (and honestly myself) understand why this was the right decision for me right now I want to explain to you the two types of entrepreneurs I come across the most.

My Way vs. Cool Things

If you talk to an entrepreneur for any length of time you will eventually hear them say some variation of one of two things: “I have to do things my way” or “I have to do cool things”. While you may hear both from entrepreneurs only one of those is really right.

To the “my way” entrepreneur it doesn’t matter so much what it is that they’re doing as long as they are doing it on their own terms.

The “cool things” entrepreneur doesn’t care so much what it is they are doing, or who they are doing it for as long as they are doing something cool.

Both end up as entrepreneurs because that basic need wasn’t met. There are other types of entrepreneurs but my experience is the bulk of them fall into one of these two buckets.

Some History

I’ve been doing social media for over 5 years now. I got into it because I was passionate and I loved the field. While there is a healthy amount of “my way” entrepreneur in me (I have no problem walking away and doing something on my own) at the heart of things I’m a “cool things” entrepreneur. Five years ago I set out with a goal to be a leader in this industry.

For the first 3 years I was an entrepreneur because it was the only way I could accomplish the cool things I wanted to get done. Then HP came along and offered to let me do the things I wanted to do on a much bigger platform. This was a very cool thing. It was an opportunity I couldn’t pass up. As I entered my second year at HP I began to realize that because of the downturn, re-orgs and other factors the cool things opportunity was wearing out. Fortunately I filled my cool things fix with TechBoise, Highway 12 Ventures and helping local and regional startups. Lots of very cool things.

But I knew things at HP were coming to an end (more on my end than on theirs - I was getting bored). I needed to figure out what my next cool things was going to be. Doing a startup seemed like the right idea. I had no shortage of ideas and like I said the doors were open to the right one.

Complications

There were two complications to making something the right idea. I was no longer a young 20 something with few responsibilities. I am a mid 30 something with a wife, 3 kids a mortgage a student loan, car loans, etc. While that may sound like a lot (it does every time I start thinking about it) I know that it’s not an insurmountable obstacle. My idea just has to be a little better thought out.

The other complication I had was that I lived in Boise. Boise is a great place for startups. Just not the kind of startups that would make the right kind of idea for me. Developers (especially the kind I would have needed) are in high demand and in small numbers in Boise. If I lived in Boulder, the Bay or Seattle that would be another thing. Yes I could use developers from anywhere, but I didn’t have the personal relationship to rely on a developer I didn’t know from another state. I would have had to rely on my network and while, again, it wasn’t an insurmountable obstacle it created one more factor in creating the right idea.

I had two ideas I came really close to launching. I was just never quite able to get all the pieces lined up just right. That’s when Waggener Edstrom started recruiting me and ultimately made me a deal I couldn’t refuse. It wasn’t just the money, because once you calculate the higher cost of living of Seattle to Boise I’m not that much further ahead. The opportunity I couldn’t refuse was the chance to move to an even bigger platform than I had at HP and do even cooler things for a variety of companies. At Waggener Edstrom I work in Studio D, and my role is basically to do R&D while working with clients. The initiatives and programs we put into place get turned into products and processes that get pushed throughout the rest of the company. It meets my “cool things” requirement more than any job I’ve had before.

The Honest Answer

Everything I’ve told you is absolutely true. All of these are the main reasons I took “the job.” But there is another reason. One I have a harder time articulating and even harder time admitting- I was scared.

I’ve done the startup thing 3 times before. All of those times have ended in varying degrees of failure. That’s not totally true, but to me that’s what they feel like. I never achieved my goals and had to walk away with less than I had expected. Some of those times were mostly out of my control. Some of those times were completely within my control. I have always learned more than I thought was possible and never regretted the decision to do them. Just regretted how they turned out.

I see serial entrepreneurs that have been successful and I marvel. It’s proven that when you have one success you are much more likely to repeat success. I think that when you have that success, or a part of that success you learn to identify, on some cognizant level, those little things that happen that lead to success. I’ve never witnessed that. I’ve gotten really good (maybe too good) at identifying those little things that lead to failure, but just doing the opposite doesn’t lead to success. If you have 10 courses of action in front of you, 1 leads to the highest degree of success possible, 1 leads to absolute failure the other 8 lead to variations in-between.

For as smart as I am, for as experienced as I am and for as well connected as I am, I don’t know that I could produce success. I believe I could. But I don’t *know* that I could. And ultimately that’s what prevented me from ever coming up with the right idea.

And while I know that I made the right decision at the right time for me and my family, I wonder if I’ve prevented myself to never finding out.

To some of you that may sound like the most depressing statement in the world. I say it more out of curiosity that sadness. I get to work on so many cool things every day. I get to do things no one else has ever done before. And honestly I get to do most of them *mostly* my way.

These cool things that no one else has ever done before provide me something else. They provide me with little opportunities of success. Every time something goes well or better than expected or completely surprises everyone, I see little things happening. I see failure averted and I learn to trust myself more and more.

If that day ever comes that I am no longer working on cool things. If my job becomes a job and the passion is gone I don’t think I’ll hesitate to do what I’ve always done: Go find the next cool thing. That may be on my own or that may not. I don’t know. I’ve quit trying to predict my own future. Instead I just predict the next cool thing and make sure to put myself in it’s way.

Since leaving Highway 12 Ventures as their EIR Mark and the guys have allowed me to guest post as I have a chance to reflect on my time here. If you want to read more about me you can follow my blog New Comm Biz

Tags: Entrepreneur, Highway 12 Ventures, Start-Up, Tac Anderson, Waggener Edstrom

This entry was posted on Tuesday, August 18th, 2009 at 9:47 am and is filed under Start-Up. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.