People pay me money to tell them things. This is one of the great scandals of the modern economy, and I intend to keep it going as long as the checks clear.
I coach CEOs. I run peer groups where founders sit in a circle and admit, out loud, things they’d never tell their boards, their spouses, or their therapists—which tells you something about the order of operations in a founder’s life. And after years of this, I’ve collected a small pile of truths. Not frameworks. Not a 2×2 matrix you can put on a slide. Just truths. The cranky kind. The kind that don’t fit on a mug, mostly because they’re too long and partly because nobody wants to drink coffee out of mortality.
Here they are. Read them or don’t. I already got paid.
Today is the good old days.
Right now—this Tuesday, this quarter, this stretch where the runway is short and the term sheet is soft and your best engineer just gave notice—this is the period you’re going to describe wistfully in a few years. “Remember how good we had it back then?” you’ll say, to someone who wasn’t there and doesn’t care. The garage. The whiteboard. The terror.
You won’t remember the terror. You’ll remember the closeness. So here’s a radical productivity hack from a man who hates productivity hacks: enjoy it now. Skip the middleman. The nostalgia is coming whether you book it in advance or not—you may as well get the early-bird rate.
Learn which losses are worth an “Oh well.”
This is the whole game, and almost nobody is taught it.
Some losses are Oh well losses. You lost money—oh well. You can make more; that’s literally what money is for, it’s the renewable resource that everyone treats like a vital organ. You lost the deal—oh well, there’s another deal, deals are like buses except they smell worse and arrive less often. You lost the job—oh well. I’ve been fired three times. I recommend it the way I’d recommend a colonoscopy: deeply unpleasant, occasionally lifesaving, and you find out things about yourself you’d rather not know.
And then there are the losses that do not recover from an Oh well. A partner. A friend. Your health. The kind of thing where the word “oh” comes out of you involuntarily and the “well” never arrives at all.
The entire discipline of a good life is telling these two categories apart—and then, this is the hard part, acting like you can tell them apart. I have watched brilliant people torch a marriage over a missed earn-out. I have watched them grind themselves into a hospital bed defending a valuation that a recession erased in an afternoon anyway. They knew the difference. They just couldn’t feel it in time.
Feel it in time.
“You can’t be too rich or too thin” is BS.
It’s a fun line. Wallis Simpson supposedly said it, and look how that turned out—she got a king and a lifetime of staring at him over breakfast wondering what they were going to talk about for the next forty years.
You absolutely can be too rich. I know rich people. Some of them are great. Some of them have turned their whole personality into a balance sheet and are surprised, surprised, that nobody comes to the party. And you can definitely be too thin, a sentence I am qualified to write because I have never once been in danger of it.
Here is the thing you cannot have too much of: people who cherish you. You cannot over-index on friendship. There is no point at which someone says you know, Glen, you’ve got one too many people who’d drop everything to drive to the hospital for you. That number does not have a ceiling. It is the only asset class with no downside, no carry, and no exit—you just hold it forever and it pays dividends right up until the last day, and arguably after.
Build that portfolio. It’s the only one that visits you.
There are three kinds of people. (The lint filter test.)
I’m serious about this one. The clothes dryer is a personality test cheaper than any assessment you’ll pay a consultant to run, and I say that as a consultant.
Type one cleans the lint filter after every load. These are your optimists. They clean it after because they fundamentally believe there will be a next load—that the future exists, that they’ll live to dry again, that tomorrow is a real place they intend to visit. Sunny people. Slightly exhausting at brunch.
Type two cleans the lint filter before every load. Why do a chore now for a wash that may never come? Why pre-pay maintenance to a future you’re not convinced you’ll attend? These people are running a tighter operation. They’ve read the actuarial tables. I find them restful.
Type three says: “Lint filter?”
There is no problem being a one or a two. They’re just two ways of being a person who’s paying attention. But do not, under any circumstances, be a three. Type threes are how houses become fires. Type threes are how a small ignorable thing—a clogged screen, a quiet metric, a feeling your cofounder has stopped looking at you in meetings—becomes the thing that takes the whole structure down at 3 a.m. while you sleep.
In your business, find your lint filter. The unglamorous accumulating thing nobody volunteers to check. Then be a one or a two about it. Your call. Just be somebody about it.
Humor requires three elements: intelligence, empathy, and creativity.
I used to do stand-up. Four times. I bring this up not to brag—four is not a number you brag about, four is a number you confess—but because it taught me what humor actually is, which is the opposite of what most people think it is.
Real funny is built from three things. Intelligence, to see the gap between what’s said and what’s true. Empathy, to know where the other person is standing so you can find them in the dark. And creativity, to put the two together into something nobody saw coming.
This is why some people are funny and a great many people who are certain they’re funny are not. Being crass isn’t funny—it’s just loud. Saying something stupid isn’t funny—it’s just stupid wearing a comedy hat. Cruelty isn’t wit; it’s wit’s understudy who never learned the lines. The funniest person in the room is almost always the most observant and the most kind, which is an inconvenient fact for everyone who wanted to be funny by being mean.
In a crisis—and if you run a company, every Thursday is a crisis—the leader who can make the room laugh without making anyone the punchline is the leader who survives. Humor under pressure isn’t a distraction from the work. It’s load-bearing. It’s the thing holding the ceiling up while you figure out the next move.
And finally: there are three types of people. Those who can count, and those who can’t.
That’s it. That’s the post.
If you read all the way down here looking for the third type, congratulations—you’ve identified yourself, and you’re in excellent company, including the cranky coach who wrote it.
Now go clean your lint filter. Or don’t. Just know which kind of person that makes you.
