Entrepreneur, Explorer, Angel.

Sometimes all at Once.

23TH September 2013

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Start Up Choate/Fall ’13… Yes but Why

Next stop: SiliconBeach

Next stop: SiliconBeach

Note: Choate’s fledgeling Entrepreneur/Angel community begins its roadshow next week in LA and San Fran. To register (sorry: no Deerfield!) try this link. 

And as I began planning for our Fall Roadshow this recent post in Wait but Why caught my eye (kudos Woody Marshall for his FB share). It maps out, in quite stark and occasionally hilarious terms, why Gen Y has trouble with happiness: out of whack expectations don’t mesh well with reality.

I’ve written before about what I learned at Choate and how it helped me as an entrepreneur and angel. And so before jumping on planes to LA, SF, Boston and NYC for Choate’s Start Up program, I began to imagine what it would take to align expectations and happiness in the world of Start Ups.

1. Entrepreneurs are lionized in our culture: they are today’s rockstars. They have the Freedom to do as they please, work on what they want, when they want. The possess a can-do attitude and they are driven to making “dents in the universe”. What could be better!?! As one reads this stuff, it seems like everyone else has it figured out. And of course the natural reaction is, as Steve Martin said in Dirty Rotten Scoundrel’s “I -want-this!!!”.

2. The Media is in on it: these stories SELL. Every wiz-kid who started in his dorm room, got fired, came up with some digital arcane solution to something we didn’t know we needed five minutes ago… makes for great fodder. The stranger the better. And of course, if he/she sold out to Google, Facebook, Twitter all the better. Yes, this does happen, and the stories are wonderful. But no one seems to acknowledge they are rare.

3. So the expectations are

      • I’m gonna come up with a cool app or similar idea
      • Everyone will think it’s as special as I do – hey I thought of it!
      • People will line up to give me money at every stage- and take little for it. Because I’m me!
      • A team will gather around me and offload work for the same reasons.
      • Buyers will want what I’ve built 
      • I’ll be out as quickly as I was in, and I’ll retire

If 1,2,3 above look at all familiar with your thoughts… stop! If I can do one thing, just one thing of value for start up Choate and the entrepreneur community at large it is this:

startup-curvethis is hard…

you better love it

The rule of thumb/stats on start ups are that 80% fail in the first year, 10% the second and 5% the third. And, of the 5% left in year three, remember that the adage is about survival. The odds on thriving rather than just surviving are much tougher.

So how does one reconcile and justify taking the plunge let alone sticking a toe in the water?

First off, find something you love to do. Really love. That could be in a specific market, skill type, or even group of people. But when you imagine yourself in the long haul of start ups be sure you are aligned with a thing or group of people who are worth it.

Second: the most valuable thing you can predictably extract from most start ups is learning for the next one. As so many of them are DOA, you should expect to try more than once before seeing any degree of success. So, besides working on things and with people you love, consider each trial a chance to learn. About product, markets, and people. Sooner or later, you’ll have gathered enough of all three to make a go of it.

Third: be prepared for long and lumpyThe losers play themselves out pretty quickly… the winners usually take time and have brutal peaks and valleys along the way. Don’t get caught out of gas along the way.

No way would I discourage anyone who is thinking of this: for me it has been the most rewarding, invigorating, interesting way to spend a life and make a living. But I consider myself lucky.

And I look forward to hearing more great ideas and stories from my experience with Start Up Choate! The last road trip was awesome!


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