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Like Death Cab for Cutie, you should be making plans

Posted by Chad O'Connor  July 17, 2013 11:00 AM

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So, you want to start a business? Well, I’m certainly not going to stop you. In fact, I’m a lawyer that helps people do that all the time, so it goes a long way towards paying my bills. Even so, I believe that there’s a fiction many entrepreneurs (and, for that matter, students) have been sold, and that fiction is that success is gained by some magic combination of forward momentum and desire.

“The way to get started is quit talking and start doing.” - Walt Disney

Thanks, Walt. That’s super helpful with bootstrapping a new venture. Rather than think through what I can reasonably do with what limited resources I have, I’ll just throw whatever I can scrape together at the endless sea of possibilities floating around in my head (which may be possible when you have infinite money). Those other people that tried the same thing but failed? I’m sure they just didn’t want it badly enough.

“Risk more than others think is safe. Dream more than others think is practical. Expect more than others think possible. Care more than others think wise.” – Howard Schultz, Starbucks

Okay, seriously? This kind of advice for starting up your business is like the verbal equivalent of the “Hang in There” kitten poster: platitude without substance. It can give you nothing but motivation, and taking anything but motivation from it is a perilous endeavor.

“You jump off a cliff and you assemble an airplane on the way down.” - Reid Hoffman, LinkedIn

I am not an engineer, but I am virtually certain that anyone that builds airplanes would tell you that method is a poor way to go about doing it. Now, if you find yourself unintentionally falling off a cliff, you should indeed start trying to cobble together things that can fly and/or glide. But, if you’re jumping, you should have shown up to said cliff with something at least airplane-like.

“Execution really shapes whether your company takes off or not. A lot of people start out with an exciting thing and they want to take over the world, but really the people who do take over the world have a good plan of how to get there and the steps along the way.” - Pete Cashmore, Mashable

Well, here’s one of the most irresponsi…wait, this is actually sound, useful, pragmatic advice. I certainly don’t mean to suggest that Pete Cashmore knows everything about starting and running a business or that he’s a better businessperson than any of those other quoted founders. I merely take the point of view that his statement is of a measured tone that can inspire both entrepreneurial desire and sound business practices. Helping people set up their businesses and plan for success is what I do, so the fact that I would latch on to Cashmore’s statement as a favorite is not surprising.

In fact, I think that future founders who sit down with lawyers should have broad conversations about a litany of business topics, such as the following:


  • who is on the (tentative) founding team

  • who/what skill they may look to have join the team later

  • what the short-term and long-term revenue models are

  • where the key geographic market is

  • what type of intellectual property will be generated

  • what type of risk comes from providing such a product/service

  • what exit strategies are on the table in the long-run

  • etc.

Serial entrepreneurs do not blink when asked these questions because they have crossed all of those bridges before, either the hard way (ex. being unable to pay a key team member, who then leaves) or the easy way (ex. learning from the mistakes of others, possibly by hiring away someone’s former key team member). Whereas, those who have never asked some of these questions before have told me and others like me that they came away with points to consider as they planned for their success.

Whatever the answers are, I’m not here to tell founders what goals, dreams, cultures, metrics, etc. are right or wrong for their businesses. I know that that’s not my place and, if I had those answers, I’d be a (much better paid) business mogul or work in private equity. However, armed with this information, I am better positioned to be the valued service provider that founders need to help them position their business for stability and success.

Therefore, when you show up to meetings to get help forming a potential venture, show up ready to talk it out with someone who is passionate about your success. Any lawyer (or other service provider) worth your time and money should tell you the same and make you believe it. If they don’t, then my unsolicited advice is to quit talking and start doing your best to find a replacement.

Dan Crocker is an attorney at New Leaf Legal, a law firm serving entrepreneurs, socially-minded businesses, and artists. He lives in Brighton with his wife and three cats and generally just loves playing video games and engaging in amateur philosophy.

This blog is not written or edited by Boston.com or the Boston Globe.
The author is solely responsible for the content.

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