I've had a couple and still do.
First company I co-started was a web development company. I would say this was the best learning experiencing I will ever have. It lasted for about 5 years. During those 5 years, we first started with web design. Money wasn’t coming in fast enough, so we expanded into other venues. We did a lot of spamming (sorry, but not really) and porn sites/referrals. This was at a time when not many people were privy to spam, so all our campaigns had high conversion rates. It was pretty awesome, it was automated. We did nothing and watched the money trickle in and on top of that free porn!! (Free porn was big back in 2002). We then started developing web apps, specifically Citrix integrated with accounting. This was it, my start to retirement. We developed a subscription based service using accounting software. It was taking off. We inked a deal with a CPA firm and they wanted to buy us out for high 7 figures while we still remained in control of engineering and innovation. It was a dream. But alas, you always have to wake up from one. The accounting software company we used sent us a C&D letter. In one moment, everything went poof. What happens a few months later? I visit their website and our product was on their website ready to buy. They basically stole our product, idea, implementation, planning and business model with no repercussions. My web company lived on for another year or so, until I had a falling out with my partner. We went to court, I won.
I then started my own IT consulting company. It was too unstable and I got lethargic and was content with the money I was making from my day job. I started turning down projects and gigs. My heart was no longer in it, as computers were my hobby and it was sucking the life working in the corporate world. I stopped to save something I enjoyed. However, I still consult time to time with IT/web development and design.
Next, I purchased a brand new apartment complex in another state with the money I made from my previous endeavors. I started a Venture Capital company, just because that sounds cooler than “I have property”. In addition, I was expecting to invest in more property. But with the economy the way it was, it started being a money pit. I couldn’t keep up with the maintenance, paying my property manager and managing from thousands of miles away. I ended up selling it at a loss. This was the biggest fail. It taught me nothing and my wallet is lighter because of it. I can’t say I’m upset though, because I accounted for all the variables in owning property and was actually comfortable in my assessment. However, I failed to factor in Bush. I will likely never get into real estate again.
During the same time, I purchased a small business. It’s a store selling collectibles, comics, statues, nerd shit. In hindsight, this was a bad idea. I had no passion or interest in any of it. I just considered the monetary aspect and let my partner worry about the minute details. The irony is this business is still running. You’ll see me (well my partner mostly) at most conventions in California (Comic Con). I’m rarely involved, unless there are issues and I need to make executive decisions. I want to sell it, but I don’t have the heart to tell my partner yet. It’s his hobby. It can be way more successful if I put just even 20% of my time into it. I can’t even do that, that’s how uninterested I am.
I just recently started a T-shirt business and developed an umbrella corporation. This will be easier when I start developing more things and have it all under one roof. This is starting off very slowly, but I’m optimistic. Plus I have more ideas waiting in the wings.
The most valuable lesson I learned from these experiences are don’t partner up with someone who accents your abilities or even have the same abilities. Partner up with someone who fills your deficiencies. When starting your own business, depending on the scope, I’d highly recommended working with someone, although we work much better alone. It will never work for an INTP if you don’t have an “E”, go getter, follow through person by your side. If I didn’t have partners that “just do it,” I wouldn’t have started any companies, except for maybe IT/web consulting.
The lunacy of all this - my failed companies were more successful than my current running ones. Time will tell though.