This is a reply I sent to Robert Cringely in response to his post “Dragging our asses to Boulder“, but other people may well find it interesting.

Hey Bob,

In your most recent podcast, “Dragging our asses to Boulder”, you used a phrase like “companies that have become successful seeming despite themselves.” I paraphrased it, be I think that’s the gist of it. That had special resonance with me as I’ve had the same kind of “unintended good luck” that the other people you mentioned have had.

I won’t go in to the detail here (I can tell you later if interested), but the short story is I came up with a dumb idea in the early 2000′s, decided to wrap a web site around it and only a few months later and through no real intention of success the site was the new hot thing on the internet among a certain demographic. I was 23 years old and I had no real experience running a business, but the business I ended up running didn’t seem to care.

But here is where your comment really got me: In 2005 I decided to sell the site, partly for money (obviously!) but most because I felt like I was deeply unqualified to run the business. At the time it was supporting me financially, but I hadn’t hired any staff or done anything “Buiness-ey” with it because I didn’t think I could, I thought I needed special skills that I didn’t have.

So I sold the site and what did I find? The company I sold it to, and who I then worked for, had no better “business skills” than I did! They were just people who were also seemingly playing things by ear.

Later on, that company sold the web site to year another, larger, company. This one was a Fortune 500 company. I ended up working for them, too. I thought that the first company had been a fluke, and that a truly successful company had to have some “magic business bullets” they used to become the corporation they were.

And yet, I was wrong again! They had “business processes”, “management processes” and even “idea processes” but in terms of the actual “being business-people”, they were doing things no different than I was when I was doing it alone.

The round-about point I’m getting to is this:

So many people have totally legitimate ideas for becoming entrepreneurs but never execute on them because they think they are lacking some “special sauce” that the big guys have yet they lack. They feel inadequate, which makes them second guess themselves and their ideas which ultimately scares them off.

What they don’t realize is that those huge companies are probably just a nervous as you, though they may have a larger safety net. The ideas, drives and skills of a one-man-operation are just as viable and valid as a huge institution with thousands.

Fast forward to today and I’ve recently joined up with another startup that was founded by a former manager from another Fortune 500 company. We have a great staff with great ideas and yet these same doubts creep in — we still have moments of fear that somehow we’re just delusional and this can’t really work.

When that happens, though, I have to sit back and think about all the times in the past when I thought that “they”, the big companies, had something I didn’t only to later find out that, in fact, I was doing things better on my own than they were with huge committees and boards.

Those big companies are made up of people just like you and I, we can’t short-change ourselves by thinking they have magic qualifications we don’t.

Anyway, thanks for listening, I hope that this can be of use to you and I wish you good luck in your trip. You’re going to be passing near me soon most likely (Salt Lake City, Utah), so if you see a little red VW honking at you when you go by don’t be alarmed.

– Matthew N.
(yet another serial entrepreneur)