10 Business Lessons From a Snarky Entrepreneur

As a companion to 10 Reasons You Should Never Get a Job and 10 Stupid Mistakes Made by the Newly Self-Employed, here are 10 positive lessons I learned from more than 12 years as an entrepreneur. A few of these are rehashed from the 10 Mistakes article, but most are new.

This list is the result of the liberal application of the advice from item #5, “Fail your way forward.”

Without further ado:

  1. Network selectively. Nothing says “business newbie” like shotgun networking. “You never know when someone might say yes” is marketing for dummies. Take the time to build a profile of your ideal customers, and target your networking activities to reach them. Speak to those who are already predisposed to want what you offer. Almost any profile is better than “anyone with a pulse.”
  2. Buy the best chair you can find. You’ll probably use your chair more than any other piece of business equipment, including your computer, so don’t settle for a crappy one. Consider a chair with padded arms and a high back (to the top of your head) for maximum comfort. The most expensive chairs aren’t necessarily ideal for you, so you must test your way to comfort nirvana.
  3. Understand that relationships are more important than contracts. Business deals are relationships between people. The signed piece of paper is important, but it’s merely the result of the relationship, not the cause. If the relationship crumbles, the contract won’t save you, although it could be very lucrative for your lawyer.
  4. Think for yourself. Unplug yourself from follow-the-follower groupthink, and virtually ignore what everyone else in your industry is saying (except the ones everyone agrees is crazy). Do your own research, draw your own conclusions, set your own course, and stick to your guns. When you’re just starting out, people will tell you you’re wrong. After you’ve blown past them, they’ll tell you you’re crazy. A few years after that, they’ll (privately) ask you to mentor them.
  5. Fail your way forward. Recognize that Ready, fire, aim is superior to ready, aim, aim, aim. Straightforward trial and error produces better results than endless vacillating. If you’re afraid to make decisions and act on them in the face of ambiguity and uncertainty, get a job. Failure’s lessons are essential to success.
  6. Become so organized it disgusts people. You’ll never achieve perfection, but you’ll be far better off than your peers who spend two weeks every year looking for things they misplaced. If you aren’t chronically well-organized, punctual, and dependable, rest assured you’re competing with someone who is.
  7. Embrace opportunities with limited downside, unlimited upside. The best deals are those where your risk of loss is predictable and fixed if things go wrong, while your potential gains are enormous if things go right. Take such deals whenever you can get them if the odds of success are halfway decent.
  8. Develop strong character traits. The height of your success is determined by your character more than your conditions. Face your fears to develop courage. Push yourself to build self-discipline. Identify other character attributes you’ll need to succeed. Entrepreneurship is as much about character building as it is about business building.
  9. Optimize your personal energy flow. Conduct 30-day trials to test various diet, exercise, sleep, and caffeine consumption patterns. Adopt the routines that give you the best concentration and focus. Dump your excess fat at the gym instead of slogging it to the office every day.
  10. Do what you love, but be damned sure it’s profitable. If you do work you love, but it doesn’t generate income, your business will fail. If you do work you hate, but it generates income, your health will fail… and your business along with it. If you can’t do what you love and make it profitable, you’ve either got a hobby or a headache, not a sustainable business. Don’t settle for anything less than passion and profit.

You may disagree with some of these items, or you may find some of them worthless, but no matter how hard you try, you’ll never convince me #2 is wrong.