09/27/2011 02:31 pm ET Updated Nov 27, 2011

How's Your Wolfpack? Startups and the Vegas Litmus Test

I love The Town. Ben Affleck does a great job as actor/director and effectively neutralizes the whole J-Lo/Gigli debacle. The other night I turned it on, figured I'd catch about 30 minutes and fall asleep. Three hours later I turned the TV off at 2:30 a.m., having watched the whole movie... again. As much as I like it, it's not the true reason I was still up.

When you lie in bed and start thinking, sometimes it's hard to stop. This particular night it was work. I'm doing so many things I'm excited about these days that it's hard NOT to think about work. My last job was at an ad agency. The two worlds have as much in common as Michael Moore and Rush Limbaugh (if you discount the zaftig shape they share). Previously, when work kept me up, it had more to do with how unhappy and bored I was. Is that stress? Sure, but it isn't pressure.

For me, and, I think, for many entrepreneurs, it's the pressure that beckons like a siren's song. Pressure had the tendency to breed fear -- fear of failure, or mistakes that lead to missed opportunity. So how does one mitigate this fear? By being part of a great team (said in the Al Capone voice from The Untouchables). And how do you know when you've built a truly great team? I believe I may have stumbled upon the perfect litmus test while lying awake one night thinking about my own team's chemistry:

Ask yourself how you'd feel about a weekend trip to Vegas with your founding team.

You learn a lot about people in Vegas. Remember, Vegas is all about "the wolfpack." Wanna fight for your agenda? What is the reaction when you push it? Are you willing to eat at Olives if you really think Nobu is the right choice? Does someone bitch because they are at Cirque du Soleil instead of playing blackjack at The Playboy Club? Oh, and are you willing to share a room? We're on a fixed budget until we raise another round. How would you and your startup wolfpack fare... would it be a fun, team-building adventure or a disorganized, every-man-for-himself mess?

I haven't personally tried this litmus test yet but I'll say I'm pretty confident in my wolfpack. Why? Because if you want to build a very large and successful company, and let's assume you do, then the the founding team has to be highly functional, passionate about the idea, respectful of one another, willing to disagree and happy to support any decision (regardless of how they voted). Mistakes are lessons, not knives to be shoved into your back to prove a point. Trust is established and rewarded, not violated. Accountability is consistently upheld. Pressure is embraced as fuel that drives to the finish line.

Are you ready to build something? Willing to "take the leap" as so many of my friends have said to me? Then be honest with yourself. Open yourself up to difficult questions. Find a visionary leader who attracts extraordinary talent... talent that would thrive together as a "wolfpack" in Vegas.

And get ready to stay up late watching The Town. A lot.