Why to Not Not Start a Startup

I love this article – because somehow, I just get the feeling they are talking about me.  Really.  I’m not trying to brag, because I have no right to.  I’ve started nearly a dozen companies (ten, actually).  Six of them still exist, in some form or another.  I have nothing (substantial) to do with 4 of the remaining ones, and I’ve never made money (serious money) off of any of them.

I’ve gotten to be pretty good at failing small.  What I mean by that is that none of my failures cost anyone a huge sum of money – pocket change by most standards.  And I haven’t devastated myself financially (yet).  I haven’t found the right idea, with the right team, in the right market, at the right time.  Not yet, anyway.  I will.  I’m sure of it.

I’ve also not succeeded in a huge way yet – I’ve made some money (enough to spend a year or two trying new things).  But I haven’t paid off my mortgage and my newest automobile is four years old.  I have a son going into college this fall, and I don’t know how I am paying for it yet.

But here is the important thing (at least to me) – this does not scare me.  I know it should – but it doesn’t.  The truth is, I have far more ideas and opportunities than I have time/money to take advantage of.  So it’s just a matter of the right time, and the right opportunity.  Add in the right team in the right market, and I know I’ll do very well for my team, myself, and my family. 

I’m at the point in my life now that I can’t imagine NOT being in a startup.  The first successes I had in life were with startups.  The greatest financial success I had in life was with a huge global company where I was rewarded very well for cyclically hiring and firing people as the stock price fluctuated.  I bought into it, and I was living the American Nightmare – spending money I had not yet earned.  Because I trusted the source would still be there tomorrow. 

Eventually, it wasn’t.  My job, and my lifestyle were outsourced.  I went from a six figure income with houses in Texas and Florida to a zero figure income in the 2 minutes it took my new manager to tell me he didn’t need me any more.

Reality check time. Serious gut-check time.  What did I do next?  What did I want to do?  What was I really good at, and what made me happy?  Honestly, it wasn’t ever the money, even though I fell into that trap for a while.  But the money just made life complex – I spent more time worrying about money than I did about me.  Or my family.  The problem was, I was making just enough money to keep me enslaved by the system.  I wasn’t making enough to ever break free.  And this wasn’t an accident – my former employer planned it that way.  When I was first promoted to a management role I had ZERO debt – not even a car payment.  My boss’s boss’s boss told my boss to “tie me down” – to pay me enough that I could buy a house (and I bought two, eventually).  They wanted me tied to my salary.  Don’t get me wrong – I loved those bosses – I still do.  I have a ton of respect for them for trusting me – they gave me opportunities few people would have been willing to offer.  I had never run a QA group – they let me build one.  I had never managed a remote office – they let me do that, as well as handle two office moves over 5 years. They let me run my business.  I knew the trust they were placing in me – and I was not going to fail them.  Even if it took 20 hour days over a four year period.  I started with zero employees and ended with 47 – more if you count those that worked for me but didn’t report in my food chain.

So I had a bit of a pedigree at that point – a proven track record of building groups, managing budgets and delivering customer expectations.  I could have gone to a lot of companies.  But what did I want to do?

First, I wanted to build something.  There was a time I could walk through any computer or electronics store with my kids and point at the shelf and tell them, “See that, and that, and that?  I helped build them.  I was responsible for testing them.  It was my job to get them on the store shelves”.  Yes – I have to build something – it’s in my nature.  Yes, I have a deep desire to point at something, and tell people, “I helped build that”.

That’s what makes startups so painful for me – I can’t point at anything right now that I built!  There is a lot I have been involved in building over the last two years – but I was either a contractor under NDA, or the products haven’t released (or I am no longer involved with the company, and don’t feel comfortable talking about them as MY accomplishment).  I have nothing right now to point at.  Except one thing – my absolute belief that I will (one day soon) be able to point at something again, and tell my kids (and even their kids) that, “I helped build that”.

I live in a very different world than most of my friends.  They work 9-5 in offices, mostly for big companies.  I stay home and “do stuff”.  I know that’s how some of them see me – as the guy staying home “doing something, but we aren’t sure what”.  When they are here, I am a good host – I’m not working with guests in the house (usually).  So they don’t see the 20 hour days or hear the telephone conversations taking place at 2am.  They just don’t get it.  They can’t – it’s like a foreign language to them.

I’m a serial entrepreneur.  I’m just not a really good one (yet).  But I have the most important attribute for success – I KNOW I WILL SUCCEED.  Even better – I’m in no damn hurry to do so.  It’ll come.  And I’ll be prepared for it when it does.

But really – I would rather build marginally successful startups than ever return to working for a company that I was not personally invested in, and that wasn’t personally invested in me.

So, if you have a startup idea, and you want to bounce ideas off me, call me.  Contact info is in the Consulting Page.  And the initial consultation is always free.   And I can be trusted.


So here is an even more striking statistic: 0% of that first batch had a terrible experience. They had ups and downs, like every startup, but I don’t think any would have traded it for a job in a cubicle. And that statistic is probably not an anomaly. Whatever our long-term success rate ends up being, I think the rate of people who wish they’d gotten a regular job will remain close to 0%. The big mystery to me is: why don’t more people start startups? If nearly everyone who does it prefers it to a regular job, and a significant percentage get rich, why doesn’t everyone want to do this? A lot of people think we get thousands of applications for each funding cycle. In fact we usually only get several hundred. Why don’t more people apply? And while it must seem to anyone watching this world that startups are popping up like crazy, the number is small compared to the number of people with the necessary skills. The great majority of programmers still go straight from college to cubicle, and stay there.

Source: Why to Not Not Start a Startup


  1. Bruce – interesting link – thanks. I agree – a big part of being sucessful is finding people to work with that you “just connect to”. Customer relationships are important, but without personal releationships with your co-workers I don’t think you can fulfill expectations outside your domain. In other words, you have to be happy to make people happy.


  2. Also worth reading: http://blogs.salon.com/0002007/2007/03/26.html#a1818 on finding people with whom you can make a living.