What do you want your life to look like?

It’s such a simple question yet so profound. Instead of asking yourself what you want to do with your life, envision how you want it to be five or ten years out and start architecting it right now.

A year and a half ago I left LYFE Kitchen, the company I co-founded. I had spent the previous four year working and traveling non-stop in order to build the nations first coast to coast great tasting and good for you restaurant chain. It was a very exciting time even if I was never home, had no life, was the hardest thing I have ever done, and was completely consumed by the goal of “Changing the way America eats”.

I loved what I was doing so much that I don’t think I worked one day in four years. That is not to say I loved it all day every day but more days than not, I was happy.

Then it was time to move on.

About four years in we were taking in money from a strategic investor. It was very obvious that they were going to bring in their own team which means I wouldn’t be around very long. You are probably thinking that I cashed out with millions in the bank or have equity worth many zeros. I wish. The company made an equity investment so no one got any money out. On top of that, there was a cram down about a year after I left so my equity was basically worthless (including my initial investment). So after 4 years of hard work, I had only experience to show for it.

Was it worth it? YES. Not for a second do I regret it. We created something special and I am proud of that.

I took some time off to recuperate and then started working on a business idea with a former colleague. We worked on it for a few months but it became evident that he couldn’t dedicate the time needed to get it off the ground.

So what the heck am I going to do with my life? I love tech, I am in SF, know restaurants, and have a wealth of operating knowledge. I should do something in the food tech space. Makes perfect sense.

After a month of talking to different companies, I joined an on-demand food startup as co-founder/ COO. After about 30 days I realized that the CEO and I weren’t a fit, so I left. I had no plan and no idea what to do next. I know I didn’t want to work for a large company but other than that, I had no real direction. So I asked myself a fundamental question. What do I want my life to look like? So simple.

I want to live where I want, travel around, and be able to have enough money to do so. Sounds easy enough, right? LOL. I started to think through what I could do to make this happen. The list actually was quite short. I could be a consultant or have a business on the internet.

I already had been a consultant and didn’t want to travel for business that much, so that left one choice; run an internet business. Ok, but what does that even mean?

I didn’t want to start a business from scratch again, so that left buying one. Are small internet businesses even for sale? The short answer is yes. The long answer is there are a lot of bad ones out there.

After a few weeks, I figured out which business brokers had the good sites and which ones had some ones that shall we say were “less good” or scams. What was amazing is how many real businesses there are on the internet and have serious cash flow. These are businesses that have been around for years, are doing well and have ample room for growth. They are content businesses, e-commerce businesses, lead generation businesses, and many other business models.

Truthfully, I never gave much thought about internet businesses that weren’t going to be the next big thing or could be worth $1B some day. I had bought into the hype.

All my research led me to this hypothesis. There is a huge opportunity in buying small internet businesses and rolling them up to something larger. Think IAC but on a much much smaller scale. I could use my tech, consulting, and ops background to scale these businesses and create a mini portfolio that plays off one another. I know it’s not original, but it got me hooked.

I have spent the past six months searching for the right business and after a false start, I am in the final stages of signing a purchase agreement for an e-commerce business composed of three sites.

Why did I write this post? Many people have asked me what I am up to but more importantly, I want to put my stake in the ground and say I am going to create a different future and create the life I always wanted. It’s the path less traveled and it’s going to be hard but will be worth that much more in the end.

I am also going to blog about this adventure and all the steps along the way. My successes, failures, highs, lows, and everything in between. I invite you to join me on my journey @ www.singlesordoubles.com.

Why singles or doubles? It’s the core of my hypothesis. If I can hit a solid single or double every time, I won’t need to hit a home run to win the game.