So you’re a new entrepreneur. Here’s some snippets of wisdom from my entrepreneurial experience in the form of DOs and DON’Ts that might help:

DON’T spend too much time on an opportunity that keeps sliding or becoming too complicated to chase.

When the opportunity of a lifetime becomes too complicated (too many hoops, too many variables, too many dependencies, etc.), take your losses and move on. It’s better to survive on small and non-ideal opportunities than go bankrupt chasing the swan with golden eggs.

DO take even the slightest change for the worse in communication as an early sign of disinterest.

When there is interest, there is fervid communication. Pay very close attention to even apparently justified delays in replies as they may be early signals that your party isn’t giving the deal the due importance. Same thing goes for timely but ambiguous responses.

DON’T waste too much time with non-decision makers.

Non-decision makers aren’t always obvious, often hiding behind pompous corporate titles – Vice President this, Program Manager that. They may have some valuable information, but once it gets to decisions involving financial or resource commitment, pay close attention to excuses in the form of needing to involve the larger group, to think about this some more, to consider more facts, etc. Quickly identify the true stakeholders and decision makers if you intend to close a deal, remembering that time may be much more critical to you as a new entrepreneur than to someone holding on for dear life to a hard earned position, and trying to convince you of his or her importance in the process. Importance in business means usually one thing: the power to commit resources without higher approval.

DO be patient with mavericks.

Mavericks usually operate outside the system and social norms. The have a relative sense of time and commitment, but they can be the source of that black swan opportunity that transforms your business. Adjust to their pace and be patient. I once met with one such individual weekly for an entire year, paying for every single lunch, despite everyone telling me I was being naive. The opportunity came as unexpectedly as I had expected, and it made the vision I had for a services companies into a reality that continues to this day.

DO adjust your personality to the customer’s.

When you run into the military type be succinct and humorless, but indulge the artistic types into long conversations that have absolutely nothing to do with the business at hand. Delight the megalomaniacs with discussions about power games, and, of course, the adventurous with stories about opportunity at the limits of bearable risk. But introduce the tough part of the business discussion early if you can. Making the transition from general conversation to concrete business later will most likely result in a sudden emergency that cuts the meeting short, leaving you looking like you’re not the one focused.

DO delegate your areas of low expertise and interest, but remain involved.

Watch particularly the temptation to delegate those things you hate, hoping they just disappear into the ether and you never hear about them again. You will hear about them, when something goes broke. I used to hate meeting my accountant, but couldn’t let him see that I was mostly disinterested in the number details: he would catch on to that and not pay so much attention to his job knowing that I wouldn’t check anything anyway.

DO keep your eyes on everything at once.

But also stay focused on a singular vision that makes you unique, that made you go into business in the first place.

DO keep a (ridiculously) open mind!

Be ready to do the exact opposite of everything I suggested above and trust your gut feeling! There are no universal recipes for success in what is essentially a continuously experimental mode of operation!

Photo credit here.