Three Things: The early days of entrepreneurship

Three Things I Learned In Saas, Sports, Tech and Live Events: 1. Entrepreneurship doesn't mean freedom like people think it does. The vast majority of those who intend to "be their own boss" one day overwhelmingly cite freedom as a reason. And there is a lot of freedom. But not nearly as much as most believe. Unless independently wealthy already, you'll still have banks, customers, the IRS, local government, and on and on who make demands of you, your time, and your calendar. Not to mention staff. Guess who covers when there are no shows? This Xanadu idea of being able to cruise in and out whenever you like? Not real. At all. In fact, you will have far less free time than you do if you work for someone else who provides holidays and vacation where you can turn off. Freedom of ideas, of purpose, of what to pursue? Absolutely. And those freedoms are what make it all worth it. But the freedom many imagine of cutting out on a Wednesday to hit the lake with some friends and unplug. Not at all. There's no unplugging. Nearly ever. 2. The Personal Guaranty is the least of your worries. Saw this great tweet the other day and thought back to our early days and the fear we had when we had to personally guarantee (financially) our loans, bank accounts, credit cards etc. Yeah, that S-Corp protects us from lawsuits and damages, but good luck getting a loan on a business with no revenue without staking your personal resources as collateral. We're not all Marc Benioff getting $2.5 mil from Larry Ellison on day one and keeping our jobs. In the end, the risk of a guaranty is a terrific harbinger of an entrepreneurs resolve. Trust me from someone who's done it and gotten as close to broke as it comes - that financial guarantee is the least of your worries. The mental, social and physical guaranty….much more demanding. 3. "What do i care about the law? Ain't I got the power?" Rockefeller had a number of 'ends justify the means' quotes and the "Battle for Uber" (or "Bad Blood" or "Smartest Guys in the Room" or "Billions" or or or) reminds us people will do just about anything to look out for themselves. And if it works? The confirmation bias goes through the roof and the justifications get even broader. When we ask start-ups we advise what they'll do if the incumbent plays dirty, they usually answer with "they wont. It's illegal. And if they do, we'll sue them." Trust me from experience kids, they don't care about the law and that lawsuit takes 2 to 4 years these days. Better have the stomach for it. (And if you do, have at it….it's a hell of a ride!)