diving inHaving invested a considerable amount of time, money, and energy into three startups, I’m often questioned about how to best prepare for starting a company.  When can you be sure that your idea is worth the risk or that you’re personally ready to man your own ship?  What should you do to lay a foundation for a successful business?  In short, there’s no simple answer to such questions.  Nevertheless, I’m happy to offer my thoughts.

First, let me tell you that you’ll never be fully prepared. Your analysis will never be perfect, you’re ducks will never all align in one perfect row. You just need to make the leap and jump in… even if you haven’t quite mastered the art of swimming yet! Regardless of how many hours you spend agonizing over your plans, there will be roadblocks you never accounted for and frustrations you never saw coming. To many, such uncertainty is enough to make them freeze and remain in a position that is unfulfilling. But the best entrepreneurs aren’t turned off by such uncertainty – they embrace it! You will never be perfectly prepared, so you really do just have to jump in and swim for your life. Here’s how I learned to swim.

Calling All Support

A strong entrepreneur does not try to go it alone. Sure, the idea can be all yours, but to turn any idea into a reality, you’ll need the support of your friends and family.  I openly attribute a vast majority of my success to the support I’ve received from the home front.  Starting a company is trying at the least, but more often stressful and time-consuming. It’s nothing short of a roller coaster ride.  Without a strong support underpinning that can help you through the tough times and cheer you on during your triumphs, you’ll burn out quickly.

Second to your family should be health and fitness. Take care of your body and stay in shape!  Regardless of how busy you may think you are, you’re never busy or lucky enough to overlook a little quality time with a pair of running shoes or a trusty bike.  Should you happen to neglect either your family or your body during your entrepreneurial endeavors, be assured that failure in one form or another is imminent.

Be Flexible

Too many entrepreneurs go into the game without stretching. They think everything will go according to plan.  As I said before, things will come up. Every startup begins with a set of assumption that must be tried and tested in the market. Sometimes, a few of these assumptions will be wrong. More often than not, most of them will be wrong.  But failure isn’t a bad thing. Continue to adapt and try out new assumptions until you find the right mix. Remember, most startups, after some growth, only look like a distant cousin of their original concept.

As a prime example, let me take you back to the day that we began fundraising efforts for my current business, Chequed.com. It was October 2008 and we were gung-ho to get the ball rolling. Hours before our investor event, Lehman Brothers went under.  The economy was tanking in a big, big way and we were hoping to convince angel investors to give us money.  Needless to say, we immediately had to readjust and recalculate, as we saw that only a fraction of the money we originally anticipated receiving would actually be coming our way.

It was precisely our ability to take a deep breath and reconfigure that allowed us to survive and thrive. You’ve got to be honest with yourself about what’s going on in the real world and be capable of going with the flow of unpredictability. In short, flexibility may prove one of your most valuable assets.

One Last Thing…

If I could go back and tell myself one thing I know now that I certainly didn’t know when I founded my first company, it would be to operate as if you are going to pass institutional due diligence any day without notice. In other words, have your crap together and your head in the game. Hire top talent, keep your finances straight, and anticipate major investor concerns.  I know it can be tough to resist the temptation to slack in these areas, as they can most assuredly be mundane and time consuming, but let me tell you – in the end, it’s worth it.

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