An Entrepreneur’s Life

An Entrepreneur’s Life

Havana one evening

I write a lot about the life of entrepreneurs. And sometimes about life, family or relationships. But I have never had a chance to write about life and family and relationships and entrepreneurs. Honestly, it’s been hard to understand it myself, let alone explain it to others I care about. Then a special friend sent me Inc. Magazine’s 18 rules for dating an Entrepreneur. I especially love #13 and #15. Here’s a few more that I would add, in my own words:

#1) Being an entrepreneur is LAH. That’s Lumpy. As. Hell. 

Love it, or leave it I guess. By definition, we create from gaps. Literally diving into nothingness, trusting we can grab the ropes of two swings (the problem and the solution), and betting we can tie the two together before we hit the ground. We make these bets with our time, our money, our devoted attention, and our passion. And statistically, a majority fail. And the best at it, simply dust off and move on, having learned lessons and picked talent we would work with again.

On this fluid foundation, we attempt to have relationships, build and enjoy families, and do something good for the community. The money comes in big lumps, followed by harrowing troughs. Salaries, benefits, pensions and the other white collar trappings are a rarity. The idiots among us look at one good month and multiply it by 12x and figure that’s the yearly take. Never happens. But the lumpiness extends to emotions, self-worth, mental health and a whole host of other baggage. We get over it, too quickly perhaps, leaving our partner dumbfounded.

#2) Nothing is a good as it seems, or as bad as it seems.

Failed financings. Mass defections of talent. Bone crushing competitors emerging from stealth mode.Code that breaks on launch. Then…Big client wins. Secondaries like manna from heaven. Awesome exits. (Multiply that by 5x if you’re an exec-angel with a portfolio). Through it all, if the business doesn’t die that day (or you don’t) things are pretty often in the middle. Leave the drama to others, and make today a little better than yesterday.

#3) It is truly special to even make a living doing this

Working 9-5 is total bullshit. Working 8-6 is even worse. Wearing some badge for working “late” and “hard” is so Gordon Gekko. Any dinosaur like that, still wearing Berlutti shoes and a bespoke single-breasted peak lapel Hermes scarf-lined suit… would never get it. Today’s entrepreneur lifestyle is quite the opposite; getting up at 4am -no alarm- to train for a marathon, mainly to have quiet thinking time and to burn excess energy and stress. She’d be walking the dog at 11am because of a Google hangout break. Working on a plane to Havana on Sunday afternoon. Picking up kids at 2pm on Monday, making them dinner at 5pm, but studying UX/UI after they are in bed. Entrepreneurs work better in short bursts anyway, and then need to recharge the batteries. It may not look like we’re doing much, but it usually involves tremendous discipline. Most suits can’t figure us out, but who cares, as long as one good partner can.

Really, the Inc.. article is that good. Try it.



Read this far? Tell me about a great entrepreneur that you know.



I mentor two kids and several entrepreneurs. Similarities are coincidental.