Swinging For The Fences

After the Entreporn controversy, I was mildly insulted by the readers that took my words to mean “be a micro-entrepreneur and have no ambition”.

Nothing could be further from the truth.

The truth is I’ve “swung for the fences” all my life.

My arrogance always lead me to believe I was too good for anything smaller.

I’ve tried to build a venture backed Google/Facebook/Groupon 4 times in my career.

  • All Channels, a human powered search engine (2000)
  • NanoFlirt, a real world meets virtual world dating system (2006)
  • Woyano, Mahalo meets wikipedia meets digital content marketplaceĀ  (2007)
  • MashAPI, a cloud based programming language combined with metered transport layer (2009)

During the ride I also built an open source PHP database layer that is the backbone of WordPress, and prior to my startup career I spent 5 years trying to be a world famous rock star, with burning passion to be as big as the Smashing Pumpkins.

Repeatedly “swinging for the fences” has been the most costly entrepreneurial mistake I’ve ever made.

It wasted huge amounts of my life and delayed my ability to be a self sustaining businessman. I was so focused on big exits, and grand ideas, that I never learned the fundamentals of building a profitable business.

If I had been less big headed, and the very first thing I had done was to built a sensible micro business instead of – “swinging for the fences” – I would have had a better chance of fulfilling all my entrepreneurial goals.

  • I would have had a more rounded understanding of “business”
  • I would have been financially free sooner (and able to pursue my larger high risk ventures)
  • I would have proven my business chops and been more likely to get funding
  • I would have retained more control of any deals I tried to initiate

My delusions of grandeur, mixed with Entreporn’s promise of glory, kept me on that 0.001% path.

Of course that’s my story. You may be one of the 0.001% who “swings for the fences” and gets it right first time.

If that’s your story, more power to you.

But don’t, for one second, think that I don’t have the intention of swinging for the fences.

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  • janko says:

    Epic response. I also tried to do all sorts of cool/creative stuff (not as well as you) and financially remained a looser now /w 2 kids. Now I am creating a “base” for myself first, even if I can’t use grandiose (often total bullshit) statements about disrupting industries and saving whole planets with liking/group buying/sharing/… etc.

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