10 Things I’ve Learned from Entrepreneurs

I’ve started several businesses myself and I’ve worked with hundreds of startups. I’ve learned a lot more than 10 things through those experiences … but who reads anymore?  Here are the 10 things I thought of between playing with my daughter and feeding the dogs.

  1. Keep it simple. Most businesses start off way too complex. When you launch a business, if you don’t feel like you’re leaving a ton of money on the table because of the things you won’t do, you’ve probably not gone far enough toward sharpening your value proposition. Narrow is better. 
  2. Think small. You will never earn $50 million in your first year. Don’t tell people you will and don’t create a plan that’s doomed from the start. It feels really great to tell people you did better than you thought.  You just look stupid when you plan for $50 million and barely break $250,000 (which is a great start, by the way). Plan on earning between $100K and $250K per employee in your early days. No more (even if you have funding).
  3. ABH (Always Be Honest). Seems obvious, but it’s not. Don’t lie to clients, employees, business partners or your family. It’s the smallest lies that burrow into your culture. Like the lies you tell clients … “I sent that email on Wednesday … didn’t you get it?” Or the lies you tell your spouse … “Everything is great at work – I’m sure we’re right on the verge of a major breakthrough.” The worst lies are the ones you tell yourself … “I don’t know why it’s not working.” Yes you do – you always do.
  4. Stockpile cash. No matter how much cash you thing you need, you need more. New companies choke without cash. They can’t hire and they can’t market. If you don’t have cash, you don’t have a business. You’re not going to win the lottery, and you won’t fund your business through revenue.
  5. Choose partners carefully. Get to know your partners very well. Work together for a while before you commit to an official partnership. Before you become partners, negotiate a buy-sell agreement. Most companies fail because the partners hate each other. I promise – I’ve seen it a thousand times.
  6. Don’t be too nice. It’s your job to lead, not start a new club. Sometimes that means you have to deliver bad news to people, like, “You’re fired.” And always put your health and sanity first.  Remember, you started the business to fulfill your vision. People will try to mooch off you (either your brain or your wallet or whatever …). If you feel like you’re being taken advantage of, you probably are. Pull the ripcord fast.
  7. Don’t be too mean. There is no profit in being an asshole. If you can’t keep from being an asshole, don’t start a business. You’re just going to make a bunch of people’s lives terrible (that is, if you succeed, which is very unlikely.) Don’t laugh at coaching and therapy. If you’re starting a business, you’ll need both.
  8. Don’t fuck with people’s money. If you say you’re going to pay someone, pay them. Don’t fuck with commissions, salaries, bonuses, referrals, reimbursements … whatever. Just don’t do it.  Don’t fuck with people’s money.  If you made a mistake (set a commission plan too high, for example) you better tell people you made a mistake and then fix the problem gradually. After all – it was you who fucked up, not them.
  9. Get off the dime. By the time you’re comfortable making a decision, you’ve already lost half the value of doing it.  When you’re running a business, all of your decisions are tough. They’re all life and death. If you can’t be decisive, you’re going to screw yourself or someone else. Fire that person. Hire that other one. Spend that money. Launch that campaign. Sponsor that event. 
  10. All Business is Personal. At times, you will be tempted to believe that business is different from real life. That there is a different set of rules. “It’s just business …” Well it’s not. All business is personal. When you cut people, they bleed. Make the world a better place by caring about others. We’re all sick of you fucking sociopaths.