top of page

Connection versus Connections

Now that we have reached 8 billion people, how do we find one another?

I fly a small plane between a cabin on the central coast and a cabin I’m building in the mountains of Idaho. This contrast is not unlike my two professions, as a backcountry bush pilot and a headhunter. Where commercial aviation delivers the masses, and private aviation the elite, I think of flying a small plane as delivering unique people to hard to reach places.

On a philosophical level, or at least as it relates to my job in tech, we might compare this to the difference between connection versus connections. Never could the singular versus the plural be so stark.

Connection Sells

We are driven by a need to connect. Offer a product or a service that provides it and you are tapping into a neurobiological need that runs directly to our amygdala. Its location so deep in our brains is an indication of its importance. It also says a lot about how primates’ brains evolved. Just as rejection from the clan was death, today we are bombarded by constant triggers to be liked, seen or connected with in a way that not having them leads to depression and isolation. A kind of modern day death.

The depth of connection is a factor of substance, so it makes sense that those that offer “connections” are usually flying empty-handed. Or as my grandfather used to say, “there’s the ice; then there’s the iceberg.”

In the mining town of my grandparents, population 62, we have a dirt airstrip and a few bars. Most of the pick-up trucks outside our Western-front town belong to fur trappers, pilots and gold miners. I grew up spending my summers working on our small mine, which was really just an elaborate excuse to fish. “Find yourself a good place” my grandfather used to say “and stick to it”.

The same could be said for people. Surround yourself with good people, and good things will follow. I focus exclusively on the so-called PayPal Mafia and more recently, the rising Palantir Pack. “Never get in the way of an entrepreneur and their dreams” Joe Lonsdale used to say, as we worked on the first 100 hires at Palantir. “The people we want have dreamed of starting their own companies since they were twelve-years-old, and every decision they have ever made since that time is towards this goal”. So I spend a lot of time trying to convince people to come and do that together. When their networks are built and they are fabulously wealthy, they can go do it on their own. We are seeing this now bear out:

Run Towards Substance

Our town in the Sawtooths sits at the confluence of two rivers, which join to make the longest salmon run in North America, over 900 miles long. We are the gateway to the River of No Return Wilderness, the largest uninterrupted wilderness in the lower 48. The only way through it is to float or fly, and our little airstrip is the launching point to week-long river trips and over 200 backcountry airstrips. From my cabin building site I look upon a thin line of wings perched on the mesa above our town. This provides a feeling of being connected to something larger. These planes deliver guides, sportsmen, miners, and “fly the mails” –we even have a flying pastor! My grandfather, my mother, and many of my cousins were all pilots. The GI Bill of WW2 produced a generation of them, and rivers like the Columbia and Snake, which our river flows into, allowed us to smelt a lot of aluminum through cheap hydropower. We out-produced the Axis powers. We won by scale.

But this is the problem with connections. Scale. And we are not winning.

The over-employment of the last decade (somebody said recently that we have somehow reached a “negative employment rate” for full stack engineers) inspired dozens of new platforms to streamline reaching them. The firestorm of Dresden became the air bombing of Linkedin. For a few thousand dollars a month, we now have services like Dover, LOXO and Gem that automate our funnel and even screen your talent. Finally the headhunter was being put out of business. But like Redfin and Zillow which promised to kill the real estate agent, we only built more tools to birth more recruiters and realtors. The system is broken.

A Forced Disconnect

I use my summers in Idaho as a forced disconnect –a kind of antidote to being the most hated of all things, a paper-pushing knowledge worker. The simplicity of stick and rudder flying — a plane built on on little more than 1950s technology — helps me to reconnect with analog things. Even at low altitude, flying the S-curves of a river or the rocky south coast of Big Sur, connects me to how things are related. A bay explains a town. A town on the edge of a wilderness explains our need to be a part of something.

And a forced landing…

“No matter what happens in an emergency,” my grandfather used to say, “always fly the plane”. As with flying, so with tech: get your head out of the dials. Ask yourself: what’s needed? What’s the most important problem to solve for?

Ignoring your instruments in bad weather will also kill you, but in the backcountry you better know what direction a river is flowing (indicates slope) or know that hot afternoons will cut your plane’s performance in half (air density). “Rudder out over the cooler air of water before making your turn” my uncle once slipped to me, knowing that a good day of fishing might once or twice find me pushing back a departure into a summer afternoon. A plane, like a mass email or even a Linkedin post, can get away from you real fast.

Mindfulness in the Fortune 100

Following the summer in the mountains, fall finds me busy with new connections. More than eighty percent of leadership changes happen at the end of Q4 or beginning of Q1. I use the creativity harvested over my time offline to produce a short video I make every year with my friend ET at Raineduponmedia, seen here. While America got back to work this year, and planes seemed to fill over night, I was compelled to write about the importance of staying still. For pilots this comes in the form of our first question: must we fly? Or am I fit to fly? I would do well to use a checklist in both of my professions. What is my ask? Does this person care? And checklists, not surprisingly, were developed by the medical community and also have a tie to our neurobiology. I write about so-called “Door Theory” hereon Medium.

Next year I’ll be working on a new book titled “Forms and The Formless — Meditations from the Fortune 100”. In the early days of Palantir I was asked to recruit chairmen of the world’s most successful companies to build a new kind of software. Over the years, these conversations took on a surprising and profound nature about how we organize and analyze our personal lives. “You can dig a lot of shallow holes,” said one chairman simply, “or you can dig one deep one”.

This reminded me of my grandfather’s comment about the iceberg. He had a great sense of humor, and despite being a man of very few words, he knew how to cut down an over-eager know-it-all teenager (which perhaps still seeps through in a post like this). One summer, last with him, I was eager to share some random fact about the type of metal in fishing hooks and World War II. I remember my grandfather raising his hand when I wouldn’t shut up:

“At this point in my life, boy, I have very little capacity for your incidental information”.

bottom of page