Skirting the edge of startups

As someone who has been involved with the Internet — and its precursors — for over thirty years now (amazing but true: I first logged in to the ARPANet in 1980 while an undergrad at UCSD) I am privileged to constantly say “been there, done that” when bright folk come up with nifty ideas about new business opportunities.
I’ve also created, launched, funded and sold four startups, though to be candid the scorecard was more like one sold and then died at the dotcom collapse, one sold to an incubator that didn’t care about it and let it die a quick death while I was pulled into other projects, one merged with a sympatico business and the joint venture never gained traction and one never quite achieved liftoff. That’s okay because they were all extraordinary learning opportunities and I sure learned a lot through these various adventures.
Learning about things like… the dark side of hiring a fancy Ivy League MBA to help run a company, the advantages of having a big law firm (and then the idiocy of not exploiting that advantage), the Faustian price of getting a big ($1.3mil) check from a venture capitalist, and the pleasure of turning down VCs who cold called, asking if they could invest in my second startup.
Now I dabble, as is probably most appropriate for someone who doesn’t have the lifestyle or unifocus needed to really put in those 60+ hour weeks required to birth a startup. The cost of launching might have diminished with things like Amazon S3 (we had servers colocated in expensive facilities “back in the day”) but the time required to turn a slick idea into a viable business hasn’t changed a bit: it’s an intense, exciting and all-consuming adventure.
That’s why I really like being on the Board of Advisors or Board of Directors of companies, actually. Because as a startup person you might well know everything you need about your specific niche and market segment, but you quite likely know very little about the business of creating a business. That’s my job, and that’s where I try to add value to the many companies I’m involved with today.
I just really wish I had a mentor or advisor during my own startup days. The outcome would have been oh, so very different…

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