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All entrepreneurs like to dream big: Things like the eight-digit sale of their business someday. Having been there—and done exactly that—I feel qualified to weigh in on what I consider, in my ten-plus years as a business coach, as the five keys to success, which too many entrepreneurs disregard at their peril. I don’t want to say they shoot themselves in the foot. But they often let the very tactics which have catapulted them to their first level of success (such as bootstrapping, penny-pinching, and fighting daily fires) to prevent them from reaching the very next level they seek.

Before I list those five keys, I think a little preface is in order. Entrepreneurs—and I see this all the time—often beat themselves up for making mistakes. Or they work too hard to try and avoid them. That’s laudable, but it’s wrong-headed. You’ll never venture down the road of success unless you pave it with your fair share of setbacks. Don’t be afraid to fail: Failing means that you tried, that you dared. And looking back on it, it means that you’ve learned.

As you grow as a business leader, you’ll be faced with decisions that no one was ever hard-wired to confront. Let me assure you: None of us was born with the knowledge needed to grow a $10 million—or $100 million—company. Those companies which do make it to unicorn status (i.e., over a billion) do so by standing on the shoulders of countless past employees, innovators, leaders, consultants, and suppliers. You can be sure that they made dozens of pivots before they hit their stride.


Okay, enough preface. Here are the five keys to big-time entrepreneurial success:


  1. Don’t sweat the small stuff. Time and again, newly-successful entrepreneurs will labor over the minutiae, at the cost of the big-picture decisions they need to focus on. Think big. Make decisions not only in the context of “today,” but “the business you will be running tomorrow… next year… five years from now.” Need help getting into the right mindset? Ask yourself: “What decision would I make today if my business were quadruple its current size?”


  1. Surround yourself with future leaders. Pardon the tough love, but if you’re still living in the low-level advisor/support-staff echo chamber, you need a clearer vision of where you want to be when you—and your business—grow up. Don’t get me wrong: There’s no need to cast off the old friends and loyal followers of your business’ early days. But you must make room, upgrade your resources, and deepen your bench. Again, ask yourself some not-too-theoretical questions:


  • “Is this the right CPA or banker for a $100 million firm?”


  • “Can this insurance agent give me guidance on risks of companies much larger than mine—and help me prepare to avoid those risks?”


  • “Can this manager still lead my team if it’s two to four times bigger?”


  • “Is this law firm experienced enough to keep me out of litigation—and if it does come down to that, could they win a fight for me?”


  1. Leave your history in the past. Here’s a mindset you need to rid yourself of right away: It’s the one that says, “We tried that before,” or “We’ve always done it that way.” That’s a surefire way to end up as a diminishing dot in the competition’s rear-view mirror. Who ever said you need to do things the same way tomorrow as you did last year? Tomorrow’s challenges are different than last year’s challenges, and thus the solutions are different, too. Tune in to industry trend-setters, skilled advisers, and outsiders. Always look at things with fresh eyes. You’ll be rewarded. Trust me.


  1. Evolve everything but your values. Review, revise, but never recriminate. Remember: Your systems will require upgrading. Your mission will change over time. The only thing you need to keep unchanged—indeed, guarded—is your set of values. Your commitment to deliver for your customers, to treat your employees with respect, and to do it all ethically and fairly, is the bedrock of your business. The ones that seem to go big before quickly spiraling out of control, only to crash and burn, are the ones that fail to follow their moral compass.


  1. Trust in trailblazers. “In the trenches.” “Smoke of battle.” There’s a reason these common metaphors for working at the front lines (another metaphor!) employ martial imagery: Just like fighting a war, it’s intense. It’s hard to see clearly. Emotions, personalities, and issues can—and will—cloud your vision. How, then, can you prevail? You’ve only got your past to guide you, and as I’d mentioned in Key 3, above, that can be dangerous. The answer, then, is to find people who have been where you are now, before you.


I always felt I was a great leader of the size of company my team was two years in the past: I had the benefit of hindsight and time to see how my decisions and the people I’d hired worked out. See where this is going? Surround yourself with people who have already seen the future. You could gain this with a coach, mentors, and an advisory board. (All of the $100 million companies I’ve worked with have had them.) Seek them. Lean on them. It’s not only a wise strategy; it’s also immensely gratifying. For both parties.

Are you ready to unlock the doors?

Now that you have the five keys, will you use them? If this article struck a chord with you, you might want to consider taking my (deceptively!) simple eight-item discovery questionnaire: the answers, which I can discuss with you in a no-obligation phone call, can be both eye-opening and empowering. Get in touch with me today to get your free questionnaire, and to book time for that call. [email protected]




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