Most entrepreneurs will tell you that a new startup is a gamble. The question I’ve been thinking about lately is what kind of gambling I really like.

So I thought about my many trips to Vegas. I realized I’ve ever dropped more than $25 total into slot machines, and I’ve never even stood at a roulette or craps table. Sure, the excitement of a loud crowd gathered around a winner at these games is intriguing when it happens. But I pretty much plant my behind at the blackjack tables and (fortunately) usually leave having paid for my trip.

A lot of people I know do the same thing at the poker tables. One family friend is even ranked something like #400 worldwide.

So I got to thinking about what blackjack and poker could teach me about business, and whether a gambling preference says anything about entrepreneurial style. I think maybe it does… Blackjack is a game of rules. They’re not easy to remember, and they come on both the playing and betting sides if you want to do well. These rules require that you be unflinching. It sucks to take a hit on a 16 when the dealer has a seven showing, but that’s what you do.

When a good group of blackjack players gets together at a table, they have among the best odds of winning in the casino. Everyone is “ganging up” on the house and hoping that a consistent strategy among players forces a good  number of busts from the dealer. And when a dealer bust happens, everyone at the table wins. I like it.

Poker is more of an individual game. You are actually trying to take money from someone else who started out the tournament as your equal. Good cards don’t matter as long as you can throw down (and play through) a good bluff.

Poker requires the same unflinching nerve as blackjack; maybe even more, because you don’t get the psychological separation of feeling like you’re beating “the house.” You are going to take the dude’s money sitting right next to you if you win.

I think some entrepreneurs really like this poker approach when they do a startup. I’ve had some experience with people who basically dealt themselves a pair of fours through a combination of not working that hard and not being that good at what they do. But damn it, these people were going to try to play their pair of fours straight through to the final round where the $100mm+ payout happens.

I’m not saying I don’t get this approach or that it can’t make money. I just think poker strategy can create the worst kind of businesses if you’re  not careful. You know, a business where managers are all puffing up accomplishments, and good employees only come in when they smell success (and bail as soon as any hiccups come along.)

My “Startup 1.0″ inspired real loyalty among the team, and some of the top talent on the Web came in because they liked being around other smart people gathered around a common strategy.

Maybe bluffing would have gotten me a payoff from IPI as things went south when the dot-come bubble popped in 2001. Or maybe I’m wrong to think I couldn’t sleep at night if I became a stereotypical, wheeling and dealing, poker champion cheeseball.

Still, I’m willing to bet that my next thing looks more like blackjack than poker. I’ll be working to attract and retain a bunch of other smart people with me at that table. Together we’ll split, double-down, play strategy and stack up the chips!