Are You an Entrepreneur?

The traits of successful entrepreneurs haven’t changed much in the digital age: you need more builders than branders, and it’s key to have a technologist as part of, or near, the founding team. But methinks there are 3 tests or questions:

1. Are you comfortable with public failure?
2. Can you sign the front, not the back, of checks?
3. How risk aggressive are you?

I know people who have all the skills to build great businesses. But they’ll never do so, because they could never go to work only to, at the end of the month, in exchange for working 80 hours a week, write the firm a check.

Unless you have built firms and shepherded them to successful exits, or have access to seed capital (most don’t, and it’s always expensive), then you’ll need to pay the company for the right to work your ass off until you can raise money. And most startups never raise the needed money. Most people can’t wrap their head around the notion of working without getting paid — and 99+ percent will never risk their own capital for the pleasure of … working.

Are you comfortable with public failure?

Most failures are private: you decide law school isn’t for you (bombed the LSAT), to spend more time with your kids (got fired), or work on “projects” (can’t get a job). However, there’s no hiding your own business failure. It’s you, and if you’re so awesome it must succeed … right? Wrong, and when it doesn’t, it feels like elementary school, where the marketplace is a 6th grader laughing at you because you’ve wet your pants … times a hundred.

Do you like to sell?

“Entrepreneur” is a synonym for “salesperson.” Selling people to join your firm, selling them to stay at your firm, selling investors, and (oh yeah) selling customers. It doesn’t matter if you’re running the corner store or Pinterest, you’d better be damn good at selling if you plan to start a business. Selling is calling people who don’t want to hear from you, pretending to like them, getting treated poorly, and then calling them again. I likely won’t start another business because my ego is getting too big to sell. I, incorrectly, believe our collective genius at L2 should mean the product sells itself, and sometimes it does. There has to be a product that doesn’t require you to get out the spoon and publicly eat shit over and over. Actually, no, there isn’t.

Google has an algorithm that can answer anything and identify people who have explicitly declared an interest in buying your product, then advertise to those people at that exact moment. Yet Google still has to hire thousands of attractive people with average IQs and exceptional EQ to sell the shit out of … Google. Entrepreneurship is a sales job with negative commissions until you raise capital, are profitable, or go out of business — whichever comes first.

The good news: if you like to sell and are good at it, you’ll always make more money, relative to how hard you work, than any of your colleagues, and … they’ll hate you for it.

How risk aggressive are you?

Being successful in a big firm isn’t easy and requires a unique skill set. You have to play nice with others, suffer injustices and bullshit at every turn, and be politically savvy — get noticed by key stakeholders doing good work and garner executive-level sponsorship. However, if you’re good at working at a big firm then, on a risk-adjusted basis, you are better off doing just that — and not struggling against the long odds facing a small firm. For me, entrepreneurship was a survival mechanism, as I didn’t have the skills to be successful in the greatest platforms in history, big US companies.

With the endless and well-publicized stories of billionaire college dropouts, we romanticize entrepreneurship. Ask yourself, and some people you trust, the above questions about your personality and skills. If you answer positively on the first two, and you’re not skilled at working at a big company, then step into the cage of chaos monkeys.

Cabo and Wheelchairs

My family — dad, sister, and I — are not close by American standards. No BBQ’s, daily calls, or watching sports together. However, I’ll trade closeness for harmony… and we have a lot of that. My friends who have uber-close, but dysfunctional, relationships with their families are often exhausted for the wrong reasons. The three of us are low maintenance, no-drama, and additive to each other’s lives. An unexpected bonus is, in addition to loving each other, we like each other — we get along well.

Every few years for the last two decades we go to Cabo, which my dad loves. This time, however, was harder. My dad is 87 and lost a lot of weight recently. His leg muscles, as they do, have atrophied, and he is having trouble walking. Our dad had been “that guy” who never seemed to age, so him requiring assistance to get around is rattling. Some of his most treasured items are medals for placing 1st in his age group (fifties) in several 10K races. He’s especially fond of one photo showing him on the medals podium celebrating his victory with a cigarette.

Both my sister and I have worked out 3+ times a week since 18, as our dad got us exercising in our teens, and it stuck. We will all need help walking at some point, but that day will likely come years later for my sister and me, as our chain-smoking, 10K medalist father got us into fitness.

The highlight of each trip is the three of us beachside drinking our dinner. The conversation inevitably turns to my dad’s ex-wives (three of them), my sister’s ex-boyfriends (guys who all lit up a room by leaving it), and my neuroses (numerous). None of these on their own are that interesting, but with several margaritas They. Are. All. Fucking. Hilarious. As cell death occurs, and it does for 100% of us, either cognitive or physical impairment sets in. We spend most of our time stationary, so having our dad ageless at 87 (alert, funny) while seated makes it obvious you want your legs to go before your memory.

Caregivers live longer than any cohort, and the number of people you love and care for is the strongest signal about how long you’ll live. Like many men I haven’t really provided care for many people. I spend a lot of time with my kids, but their mom is the primary caregiver. My caregiving is watching premier league highlights, taking them to Hibachi, and asking Alexa questions about Star Wars (never gets old). Getting my dad to and from Cabo and around a hotel — a stark reminder of how awesome government regulation is (American Disabilities Act) — is the most real caregiving I’ve done since my mom was sick. You can feel the benefits. It’s taxing, but rewarding. You have to be engaged and organized (key to brain health), and you feel you have purpose — in this case making sure my dad didn’t fall.

I told my dad it was time to start getting wheelchair service at airports, and he was cool, even zen about it. Being wheeled through security, he seemed relieved not to have to think about all the bullshit we endure on the other side of the metal detector — Which bag is mine? Where are my shoes? Fuck… do I have a vape in my carry-on? In front of us was someone else in a wheeled vehicle, a two-year-old girl. She wasn’t nearly as zen as my dad with the whole being pushed around thing — she was screaming.

All of us share strollers and wheelchairs in our past / future. We put people on wheels so they can be with us when we venture from home, and mobility is something so wonderful we pull it forward and extend it. The little girl was upset, as little kids get, and was clearly not convinced the wheels were a function of people who care about her. My dad, however, knows this is true.

Life is so rich,

Scott

Subscribe to the No Mercy/No Malice newsletter.