I had a highly-memorable beer with two of the finest entrepreneurs I've come to know, our conversation meandered to a far more important beer they'd had once a month since they started their last company. They'd both been part of massive startups, and set out together to build another one. This monthly beer of theirs teaches all of us a very important lesson, often described as 'keep your eye on the prize.'

What's the 'prize?' In a nutshell, it's getting to the goal founders envisioned when they shook hands and agreed to 'go for it,' and launch the company in the first place. For a social venture, the prize could be something important like educating 10,000 underprivileged kids a year. For most entrepreneurs, however, the prize takes the form of measurable, oft-monstrous benchmarks or goals, usually measured in subscribers or clicks, or--most often--in revenue dollars..

So what was the important monthly beer about? We'll get to that in a moment, but most startup founders spend most of their long days simply overwhelmed by the day-to-day, often hour-by-hour focus of tactically moving their businesses forward. It's a consumptive process, as we know, to the point where I remember once sitting for two hours in a board meeting only to see, when it ended, that a huge pile of dough had just evaporated in my day trading account.

So these two entrepreneurs, buried in day-to-day operations, transactions, management and details, needed a way to keep their eyes on the prize, and they did it with an irrevocably scheduled monthly beer night. Their goal was clear: to build a business that would grow to a $1-billion exit in five years. Lofty, long-term goals are seldom what one thinks about in the middle of a hectic day running a startup. The goal might as easily have been to "issue 5,000 small business loans by next Christmas," or something more achievable like "get 1,000 paying customers in a year."

What prize is your eye on? Presumably you founders thought about that question long and hard before signing up to launch your venture. Planning a once-a-month discussion of the grand prize--not the problems of the day or week--is an excellent tool to force the co-founders to take a step back and think about the long-term trajectory or future of their business. Then, after not too many beers, it's time to go back to work on the long list of tasks of the day. Key elements of the question:

  1. Has anything changed in the trajectory of our business to cause concerns that we're missing the mark?
  2. Has anything changed in the world around us--competitive, regulatory, or in the marketplace--that affects our march on the prize?
  3. Is it time to "blow something up" (often known as a "pivot") to increase our optimism about nailing the prize?
  4. Does our team remain as confident and enthusiastic about our trajectory as we are?

In this instance, the billion-dollar goal proved too elusive for these two talented pros working night and day in a very crowded space. They've moved on to climb bigger mountains, and one is already far above the base camp!

When's your first monthly session? It works as well with coffee or wine, but a regularly-scheduled meeting with one single subject on the agenda forces all to take a step back and look objectively at 'the prize' to be sure it's still in sight. If not, pivot away!