I once beat Janet Lee, the famous black widow, at nine ball in a giant exhibition. * **

While you’ll have to read to the bottom for the whole truth, let me at least  explain partially: it was excellent training for starting and growing  companies. Really. Here is what I used over the next 20 years from what I learned in  that one game:

The crowd is mostly noise: forget about them. So many startups  compete in crowded fields, with others releasing news and versions day after  day. While it’s good to be in tune, an entrepreneur has to be about supreme  focus on the task at hand. Nothing else matters.

The break sets it all up– that’s the team and launch. The entire DNA  of the table emerges with the first big shot- the break. Same goes for the  launch in entrepreneurs. Get it right and give it your all. Otherwise, the table  is a mess and takes more effort to clean up.

Know the speed of the table– market. Nothing ruins a well  executed shot than a misread of the felt. Rollers become bouncers, or never  make it to the pocket. You have to know how fast a surface you are playing on,  in either game.

Miracle shots also come with consequences. It’s amazing how  many wild triple bank shots present themselves in any nine ball game. But they  are low percentage shots. Worse still, they may leave your opponent an easy angle to finish you off, then and there. Calculate the odds, both of the shot,  and of the consequences.

Momentum is real. Make a bank shot, a lefty and a combo and you begin to feel you are invincible. You see the table with possibility, and your stroke has a confidence that could achieve anything. It feeds on itself, and it is certainly picked up by your opponent.

Think ahead: making the 3 ball does not mean you are in position for the 4. Ah, yes, the essence of nine ball is actually the next shot. Players and entrepreneurs both have to look down the table at what could be, and how their next move positions them.

Don’t think ahead too much: getting a good leave for the 4 ball only counts if you sink the 3 ball. And the reverse corollary to the rule above is: think longer term, but don[t forget to execute on the little things right before you. Otherwise, there will be no next shot.

Nothing counts as much as the last ball: run eight in a row and scratch and you lose anyways. Funny how people can stroke smoothly and confidently on 1-8 and suddenly look twice at an easy 9 ball shot. Miss and the opponent suddenly has you over a barrel in a way uncommon to the previous 8 shots. For entrepreneurs, this might be analogous to the exit: blow that and  it’s a re-rack, plus probably a waste of several of your best years.

Be a creative problem solver: there are more than one ways  to sink the shot. My game really improved when I began playing on several  levels, mostly to include banks, combos and the occasional jumper shot. But  basically, this is looking at a set of circumstances (the balls and their table  position) and figuring out the best shot for your abilities and for the odds of  leaving nothing good for your opponent. I also shoot left and righty (which  most people don’t know and makes me good money on side bets). And the  last comment is likely safe because pool players don’t read many blogs!

Don’t confuse luck and skill. I had a little of the latter, and for a moment a ton of the former. In any case, don’t stay too long at any table. Knowing when to walk is a life saver.

Shake hands and be a gentleman, win or lose. Perhaps most  importantly, the handshake acknowledges that you won or lost fair and square,  and were a sportsman throughout. This plays equally in nine ball and  entrepreneurship. Get used to it; you are going to lose a few. Handle yourself  with dignity and learn a few lessons for the next game.

*And now, the technicalities: Janet Lee was hosting the Brunswick table at  the Chicago Housewares show at McCormick Center, in the mid 90’s which is a large exhibition  hall (ok, everyone else was there for blenders and hooks!). The fact I was walking the floor looking for companies (and  eventually found a deal I did there) should not get in the way of a good story. I have lots of bizarre analogies, this is but one.

**She challenged me to ONE GAME and sank a  ball on the break. She sank two more before trying a two-banker, perhaps  playing to the crowd. In my finest nine ball moment, I sank the next six  including the 9 ball for the win. She has gone on to tremendous success as a  touring pro, and wants to learn about digital media. Knowing the odds were long  I ever would beat her in any rack again as long as I lived, I retired from  competitive nine ball that afternoon and used the lessons for angel investing  and creating businesses.

Join me in liking Janet Lee on Facebook and Twitter and thanking her for all she has done for  start-ups!