A colorful landscape depicts winding roads and an ocean
David Hockney's "Pacific Coast Highway and Santa Monica"
And what they may or may not have to teach us about creativity, ingenuity, and building something entirely new. Version 01, June 2022.

FOREWORD


Corporate values make me uncomfortable. At least that’s my reason for why it’s taken us so long to get them down on paper. 

It's specifically the emptiness and the prescriptiveness of it that makes me uncomfortable. The ego of telling someone else how to show up, how to do what they do and the risk of cynicism if you don’t get it exactly right. 

We’re building a company after all, not an ideology. What then is there to ask of each other beyond “work hard and treat one another fairly.”

And yet, after two years of failed attempts putting pen to paper, here I am, hand-to-heart, convinced that it is in fact an exercise worth doing. Because in the two years since starting this company, and today looking at the team we’ve built, it’s resoundingly apparent that there is something collectively special and unique about all of you — a certain shared sensibility or likeness. I’m not exactly sure what to call it, but I’m sure it’s worth writing down. 

Because when you put something in writing you start to understand it better, and can better pull other people into the conversation to discuss a thing more objectively and get to the root of what it is you're trying to say, or in our case, do.

And sensibilities are notoriously difficult to define. My hunch is that the format typical of corporate values, ‘5 topline phrases with bullet points underneath,’ isn’t going to cut it here. Instead, we’re better off taking our first stab in the form of notes and musings, rather than making any staunch claims on how to build a business, or company culture, or whatever it is these things are meant to get at. 

All we’re doing here is capturing thoughts and observations from all of you about what we as a group have gotten right so far in creating an environment that’s allowed us to do our best, most inspired work. 

And because I’m still uncomfortable talking about company values, we’re going to do so by talking about something else entirely. We’re going to talk about Road Trips.

The following was inspired by all the things your colleagues shared on what makes this place so special. Brought to life in one person's recollections of their first road trip.
Four puppet characters sit in a moving car on a roadtrip
1

SHOW UP WITH HEARTFELT INTENSITY.

1. My first road trip was a family road trip. We opted to forgo the annual family summer vacation and instead drive down the Pacific Coast Highway,📌 starting in Vancouver and then down the California coast. Eventually we turned inland towards our final destination, Arizona’s San Pedro Valley,📌 at the base of the Mexican border.

2. Admittedly, at age 13, the value of ‘Road Trippin’ was lost on me. That is, the merits of highways and rest stops as opposed to other modes of transportation that get you there in half the time. 

3. Relegated to the back, back seat of a Chevy Tahoe, I spent the first leg from Vancouver to San Francisco asleep to avoid getting car sick, only to be awoken sporadically by my Father’s outbursts above the radio, “Still sleeping!? Jesus Christ, kiddo I take you to the most beautiful places and you fall asleep!? C’mon, baby! This is living!” 

I like to think this was his ‘passion for the road’ speaking.

4. ‘‘Passion for the road,’ as I’ve come to understand it, is a unique mood or motivation with which one approaches being ‘on the road’ and the specific style that they bring.

For my father, it has everything to do with freedom, also possibility; who you might meet and what you might find out there.

And it looks like Tod Rungren on the radio and a bag full of sunflower seeds. Also, stopping at eight jerky shops between Carmel and Petaluma to crack the secret to teriyaki seasoning (we were at the last place two  hours until he uncovered the ultimate sugar to sake ratio).

5. And it’s a sentiment that applies very much to the work we’re doing, particularly to how we build software. (Not specifically passion for the road, I promise I won’t call it that). But what there is, is a certain type of passion, virve, enthusiasm — whatever you want to call it— that each of you arrived here with and that motivates you to do what you do.

For our everyday sake, let’s call it heartfelt intensity. 

6. Put most simply, heartfelt intensity is a variety of intrinsic motivation. Not the thing a person is motivated to do but the drive underneath it all that makes them tick, so potent it puts a bit of magic behind the eyes. 

7. It is often more innate than taught. Not everyone you meet has got it and that’s perfectly alright, but we look for those people in which it’s undeniable.

8. To give a real-life example, so many of you talk about that irreplaceable ‘spirit’ with which your colleagues approach their work, particularly the ‘‘thoroughness’ and ‘thoughtfulness’ of it. And how it plays out in their attention to detail (not so much when the details are immaterial but when there’s joy to be had in them.) 

That thing that compels you all to obsess over the details others overlook, and do it with gusto —  that’s heartfelt intensity. 
That thing that compels you all to obsess over the details others overlook, and do it with gusto —  that’s heartfelt intensity. 
9. In other words, the important element here is not ‘what are you pursuing?’ Heartfelt intensity is ‘how are you pursuing it?’ — and why? Where does all that tenacity and spirit come from? 

Like one’s ‘passion for the road’ that motivating factor is different for different people, and therefore presents differently, outwardly. So much so that it’s almost a requirement of heartfelt intensity that it be animated by a person’s unique experiences and sensibilities. The immense pride in the work comes from the personal connection. 

10. There is also an element of relentlessness and fierceness to it, unabated persistence with which a thing is pursued. But met in equal part by genuine joy, and if not joy per se then at least genuine appreciation.

11. Very importantly, this notion of ‘showing up with heartfelt intensity’ is not to be confused with working hard. Probably more importantly, it’s not at all asking people to work longer. It’s singularly about how you show up. 

12. I keep going back to that quote one of you gave us — "People find joy in the work; they find joy in the details. There’s a passion for the thing itself but also for the attitude that you take on that thing.”
People find joy in the work; they find joy in the details. There’s a passion for the thing itself but also for the attitude that you take on that thing.
And that’s really it. Tapping into the ‘passion for the thing itself’ — whatever that thing may be —  it’s the crux of heartfelt intensity and the bit we find most worth celebrating. 

A young girl wearing a sports jersey runs after a moving yellow van, attempting to jump in
2

START WITH 'WHAT COULD BE?'

1. Try to imagine it like this: a gigantic reptilian neck jetting upwards from the flat horizon. Because that’s how I first saw it. We’d made our turn inland from the coast towards a very different California. This one was drier, more somber.

Driving closer, we learned the long neck was attached to the head of an animal, and like the creature emerging from black lagoon —  slowly then all at once — the head was in fact also part of a body. A staggering fifty foot, brontosaurus statue lording over the desert landscape. Welcome to Cabazon, California📌 (Population: 2,888).

“Dinny” was the dinosaur’s name (at least that’s what it said on the plaque at the gift shop.) Cabazon’s cultural centerpiece and a relic of its heyday before the construction of Interstate 10 diverted traffic from its mainstreet. The dinosaur was left behind to play the lonely role of welcoming committee for the few, like us, who’s ‘passion for the road’ landed them on the outskirts of the Mojave📌.

It was late in the afternoon, and everyone was hungry. We decided to call the odd, tiny town home for the night. (Dad lurched the car to a halt before anyone could protest.) “We’ll have the place wired by sundown!” He loped across the parking lot towards a roadside diner at the end of the main drag, keen to drum up local intel — what to do, where to eat, where to sleep. 

2. You see, there’s a specific tact to follow when navigating these new, sometimes strange places. Or like in the work we do, when we’ve decided to do something and now we have to determine exactly how it gets done. I’ve best heard it described as a specific rhythm and tempo to tap into in order to get to better answers, faster; now that you’ve made it from Point A to Point B, how do you most expediently get acquainted with Point B, peel back its layers and uncover the best it has to offer? Not to aggrandize it too much. It’s a riff on any classic form of experimentation: hypothesize, test, iterate, repeat and so forth. But the real dividing line between this and everything else is the ‘raw humility’ that’s demanded of a person to always start from a place of “I don't know.”And I’ll take a quick pause to tease this apart because what it means to “Assume you don’t know” is important to get right both in and outside of small towns in the American Southwest. 
But the real dividing line between this and everything else is the ‘raw humility’ that’s demanded of a person to always start from a place of “I don't know.”
3. ‘Assume you don’t know’ refers to the mindset that no matter one’s prior experience, acknowledging we are addressing new and often complicated things to which there are no ‘forgone conclusions.’ It doesn't mean ‘don’t bring prior insight or knowledge to the table.’ Bring all of it. Just don’t assume it adds up to a final answer or outcome. And rather than being fueled by a frustration and lack of ‘faith’ in what’s gone before, find the bit of freedom in the notion that you don’t know, no one knows, and that where you wind up might be miles from where you started.

4. What follows then, is how one responds in the face of ‘I don’t know.’ Or to put it formally: Five Suggestions for Visiting a Roadside Town You’ve Never Been Before (as told by my father.) 

5. The first instinct of ‘I don't know’ is to ‘just start.’ Get out of the car and put boots on the ground. A whole world of insight makes itself known to you once you’re looking at a place up close and at eye level. For instance, there’s a bakery on the corner with a line around the block. Clearly someone knows something we don’t. 

6. When surveying your surroundings, be sure to go wide in your options and in your understanding of those options. Explicitly refrain from going with a gut instinct out of the gate. This can mean breadth…walk the entire perimeter of the place. Get the lay of the land. It can also mean depth…sometimes you’re on a mission and the key, relevant bit to focus on is the 12 antique shops between Main and Broad St. To put a sharper point on it: don’t prematurely take anything off the table.

7. And always move quickly. Time is of the essence. The caveat to moving quickly is that we have to move deliberately. You’re here to get to know the place; don’t leave empty handed. (Even if the conclusion is: we’re never coming back!)

8. ‘I don’t know’ solicits input early and often and changes course accordingly. What do we want more of, what do we want less of…most importantly, what am I missing out on?!

Practically speaking, this isn’t the time to travel alone if you can help it.

A hack if you’re in need of better, more expert guidance: keep an eye out for locals and regulars. They’re meccas for this insider information and a whole lot more expedient than throwing mud at the wall. Be sure to mention you’re new around here.
In fact, it’s imperative to deliberately solicit these different perspectives. As many as possible.

I Don’t Know says “tell me your thoughts! Tell me your beliefs, observations, and experiences” And actually listens to them and is never be too proud to course-correct. It says “I’m all ears” and means it. The bakery had a long line but one step in the door and it’s clearly a tourist trap. The good spot’s two blocks over. 

9. Finally, carve out space for the strange, the different and the nascent. Isn’t that why we’re here in the first place? To learn and see a few things we didn’t before?  This requires us to bake in a bit of fearlessness to what we do and how we do it, and draw on a sensibility of ‘gutsy’ willingness to put ourselves out there, usually a few times over, with the  assurance that soon enough, we’ll find the good stuff.

1. The image I want you to conjure next is my mother, seated in the passenger seat, with arms and fingers outstretched wrangling a 3 x 4 map of central California. 

There’s a philosophy in my family, unspoken but that makes itself known often and perceptibly in moments like these, for instance, the collective refusal to rely on Google Maps.

The issue being that Google Maps has a singular directive: the fastest way from Point A to Point B. Which is all fine and good most of the time, except today we had another mandate in mind: locate the best roadside tamales west of the Sierras — Interstate 10 just wouldn’t suffice. 

2. We did this periodically: divert from the highway and seek an alternative route. Like with the tamales, usually when there was more to be gained or seen (or eaten), than just a speedy arrival at the destination. 

I liked it better this way. Because to travel, without at least the possibility of getting off the main drag, robs the experience of something so fundamental to turn it into something else entirely.

It turns us into tourists, that are forever stuck in the known, the familiar, and the comfortable.

3. How then — when traveling, but also in our work — do we not be ‘tourists”? How do we push past the inertia of the same, endless highways and byways via Google Maps? To know when to seek an alternative route, intellectually speaking, with both the audacity to go far and broad in our thinking, and the humility to bring back what we find there.

To know when to seek an alternative route — with both the audacity to go far and broad in our thinking, and the humility to bring back what we find there.

4. For us, for once, I think the answer is actually very prescriptive. Before you take on anything, you pause and ask what could be?

Create the space needed to break apart that everydayness and press on it for a while. Really press on it. Go on and dream a bit. Or as Toni Morrison says it “Dream, then think.” 

And go to different places with your dreaming. Pull from elsewhere, the objective being to bring a sense of multidimensionality to what we do and how we do it.

5. In some ways, asking what could be is a mindset. 

David Foster Wallace encapsulates it as well as any: “a huge percentage of the stuff that I tend to be automatically certain of is, it turns out, totally wrong and deluded."

All of it predicated on the notion that just because something is, doesn’t mean it has to be and certainly doesn’t mean it’s right.

Just because something is, doesn’t mean it has to be and certainly doesn’t mean it’s right.

6. But it’s also a very tactical line of questioning, meant to crack any preconceived notions about how a thing should or shouldn't be. The point being to strip the pretenses from our thinking wherever possible because that’s when we can be our most creative. 

There’s a line I love from Murakami that gets at this point, How to Access Creativity: "I have to pound the rock with a chisel and dig out a deep hole before I can locate the source of creativity…I’ve become quite efficient, both technically and physically, at opening a hole in the hard rock and locating a new water vein."

Asking what could be is your chisel. 

Two women drive in a car with the top down
3

ASSUME YOU DON'T KNOW

1. Whether it’s a friend or family member, we all know that person. The one you love and love to be with — most of the time, but god forbid find yourself riding shotgun with them on a road trip. 

Because traveling, for whatever reason, brings out the worst in them. It’s usually some combination of ‘refusal to live with ambiguity’ alongside ‘refusal to admit they’re wrong’ that makes their companionship flat out not fun. 

But that’s alright. Not all friends are roadtrip friends.  

2. In contrast, there are those who ‘come alive’ when ‘on the road.’ Or if we think about it in the context of our work, who are at their best staring down the barrel of novelty and ambiguity, big questions with multi-variable answers. 

3. Take my father for instance. He was like this. Even more than just a ‘style,’ it was a full on way of moving through the world that meant he tore through roadside towns uncovering the best they had to offer.

Imagine it like this. The car would grind to a halt — in Sacramento,📌 in Fresno,📌 in Cabezon, California📌 population 2,225 —  he’d take off in a direction and relentlessly keep pace. 

“We only got three hours! And a whole lotta ground to cover!"

4. The mystery was always which direction he’d tear off in. So much so, we’d started taking bets. 

“5 bucks it’s due east then he hangs left past the traffic light!” 

But that's besides the point. In this style of experimentation, the point is just to start — it could be instinct, observation, a mix of both, or something else entirely that takes you on your way. 

And that’s the liberating part, especially when it comes to our work. There are no right answers of where to go out of the gate because the real art is ‘course correcting’ along the way.

Think about it like this: “there are no mistakes, only new paths to explore.” 

My father was good at this, largely because he was so damn good at talking to locals and drumming up intel. Where to go, what to do. What he missed. I’d never seen anything like it. He could sit at a bar and within 10 minutes get an invite to the bar tender’s timeshare in Acapulco.📌

5. But I’d also say success here is equal parts persistence and  attentiveness. When my father looked, he really looked. Where crowds gathered. Which stalls at the flea market sold the ‘real deal.’ Who was the guy at the local diner with all the answers. 

Which looks different at different times and for different people. Sometimes it’s breadth — like when we walked the entire parameter of Salinas town. Or it can be depth — like when we tasted all the hot sauce flavors at a roadside stand just south of Monterrey to make sure we took home the very best. 

The real point being to never take anything off the table preemptively, even the nascent, strange, or never-before-tried things. All’s well as long as you’re moving quickly. 

6. What I’m getting at is a calculus that says ‘The more turns you make the better, the more people you talk to the better.’ 

But it’s really not a calculus at all, it’s a disposition and a posture. One that’s got an earnest relentlessness to it. Also a sense of giddiness, particularly about the discovery. That says “there’s so much to discover, and I’ll be damned if I don’t figure it all out.”

It’s a disposition and a posture. One that’s got an earnest relentlessness to it. Also a sense of giddiness, particularly about the discovery.

The hardest part to strike then, I think, is that you can’t be too careful, but you also can’t be too confident. Somewhere in between the two there’s this specific type of curiosity that we’re after, the key ingredient of which is humility. The kind that arrives at a new place, or a new problem and is willing to assume “I don't know" — but let’s figure it out, together.

Because in our work, we encounter new stuff all the time. And when you say "I don’t know" a series of things happen that wouldn’t happen otherwise, both with how you build a product: you just start, and you start quickly, you go wide. You think twice, maybe three times about the impact of what you’re about to put out in the world. 

And, just as importantly, how you engage with people — our members and each other. Most significantly, and it’s worth underlining, you’ll intentionally pull in as many different perspectives as possible around the table. And when those different voices speak you listen. You value and respect their opinion and let them know it, recognizing you’d be going nowhere without them. 

You value and respect their opinion and let them know it, recognizing you’d be going nowhere without them. 

The outcome of all this is really what we’re after: the chance to find ourselves places and uncover answers we never would have otherwise. 

A woman holds a man's face while they sit on top of a car's hood
4

YOU'RE ON THE HOOK FOR THE TEAM

1. My father loves to tell the story about when he drove the same route as a kid with his father through the Mojave. It was 1968, the family moved from British Columbia back east. The two of them peeled off in my grandfather’s 63’ MG Coup for an impromptu detour to Fort Huachuca,📌  the Arizona cavalry camp where he grew up. 

As he tells it, his father had a thing for stockpiling sea water, insisting they stop at each coastal town and overlook to collect some. He used the bevy of glass jars he brought along with him whenever he knew he’d be close to the ocean. Then every morning when back in New York, splash the water on his face. 

Their other substantial stop was the Southern California Mattress Company, the intent to outfit the backseat of the coup into a makeshift camper van. It was a technique he’d perfected on summer trips out to the Jersey Shore. The two of them could take turns driving and the other, if needed, could get a bit of ‘shut eye.’ Mind you, my father was thirteen at the time. 

I say this all to paint the picture: mattress in the back seat, glass jars clinking. Thirteen-year-old at the wheel. When I envision it, I envision Fear and Loathing in Las Vegas but in some alternative universe, more sober, less debaucherous but barreling just as fast through the desert in high summer to the heart of the American dream. 

2. His favorite bit to retell is how it all came to an abrupt halt halfway down Route 66, in the middle of the Mojave when he woke up from his ‘backseat nap’ in horror to a yellow-stained mattress and soaked jeans. “Age thirteen I could drive solo down the Pacific Coast Highway but couldn’t make it through the desert without a pitstop.” 

It was hot and the sun showed no sign of abating. They were miles from the closest waystation. The only way forward was to yank the mattress from the back seat onto the side of the road. My grandfather splashed the precious sea water to wash it down and used the shirt off his back to mop up any excess. 

When there was nothing more to do but wait for the mattress to bake dry in the sun, he lit a cigarette, handed another to my father, and turned on the radio. 

“Don’t apologize, kiddo. We’re on the road together, that means we’re the hook for each other.” 

3. The point of this story is not to get hung up on the corporate equivalent of wetting the bed in the middle of the Mojave. The point, and why I like this story so much, is that it gets at the interconnectedness of being on the road with other people. Or in our case, the proximity that comes along with building something new together. 

It necessitates a specific type of ownership. One in which your number one priority is the collective even more so than your own work. That is, making others better. Not to the detriment of your own work, but with the mind that a rising tide lifts all boats. This isn’t a zero sum game. 

It necessitates a specific type of ownership. One in which your number one priority is the collective even more so than your own work.

4. I find it most helpful to think about a ‘social contract’ you enter into with those you’re working with. 

On one hand, it’s the respect you give. Being ‘on the hook for the team’ means having a certain dedication to the potential in other people, specifically a desire to help it grow. 

Explicitly, this looks like being direct and honest in your communication, especially when it’s not easy. As anything otherwise would be a disservice. It’s helping others see in themselves what they can’t see. Areas for growth, but also yet-to-be discovered talent. Your imperative is to uncover it, then get them behind the wheel and when it’s time, put a foot on the gas. 

Areas for growth, but also yet-to-be discovered talent. Your imperative is to uncover it, then get them behind the wheel and when it’s time, put a foot on the gas.

5. To say it outright, even the most talented person in the world won’t do well here if they don’t have an interest in helping other people grow and succeed. The question you will be held most accountable for isn’t “how have you gotten better” it's ‘how did you make someone else better?” Better yet, how have you made the collective, the team, better?

6. You also won’t do well if you’re not willing to give other people large amounts of creative freedom. Because that’s what you get in return: large amounts of creative freedom to fill glass jars with seawater and retrofit 68’ coups into camper vans. That’s what people need to do their best work. 

7. ‘On the hook’ is never meant to be punitive or imply any sense of preordained blame.

It’s just another thing, like heartfelt intensity, that's hard to teach and more often comes ‘baked in.’  That proactive instinct to pull your weight, to 'do your homework,' and contribute to whatever needs to be done for the success of the whole and those around you. 

That said, ‘on the hook for the team’ is at its best and most honest when it means we see each other not just as colleagues but as people. And, when needed, put ourselves on the hook for one another in that dimension just as much. 

At the end of the day, the product we’re actually building here is each other.

A man plays the guitar amongst his fellow musicians on their tour bus
5

MAKE THEM FEEL SOMETHING

1. We’ve talked a lot about road trips and how roadtrips relate to all the things we’re doing here: the importance of showing up with heartfelt intensity. How to pare back expectations so you can cast your net far and wide in the roads you go down. And  what it means to do all these things alongside the people you’re traveling with, so that when you get to the end of the road, what you’ve built together is greater than the sum of its parts. 

2. But even if you’ve done all that, how do you know if you’ve done it right? Or to be less prescriptive, done right by the thing? 

3. Road trips’ lack of punctuation make them particularly difficult to assess formally. It’s always onto the next. Or like any slower, more deliberate mode of doing anything, it’s much more about the process, no culminating point to tell you what it all was for.

4. What matters most is that you felt something. That’s what I think. 

On how many occasions and to what extent did you see, experience, or lay witness to a thing that made you feel unmistakably alive. 

5. When we finally made it to Fort Huachuca,📌 my father insisted we see it for the first time at sunrise. That way, we’d see it like he saw it. There’d be a different dimensionality to the place, so much so it’d “stir something deep inside” but only if we caught it just as the sun came up across the mountains. Any other time of day and it’d just be another desert. 

So, on a dry, hot morning in early July we climbed to a mountain top in Southern Arizona and watched the sun rise and turn the sand dunes a shade I’d never seen before. And he was right.

6. When we build software, it’s an opportunity to make people feel something. 

It doesn’t need to be anything major. I don’t think we’ll ever compete with desert sunrises. Just that we might make them smile, laugh, see or realize something they didn’t before. 

So many of you already do this, often in the details. You leave your fingerprints behind, so that they know it was made by another person and that person cared. 

You leave your fingerprints behind, so that they know it was made by another person and that person cared. 

7. And it’s another instance when one of you already said it best: "We see what we're doing as giving a gift to people; at the end of the day it’s an emotional exchange.”

All else moves forward from there, and I think we’d do well not to overcomplicate it. 

8. Because way too often this gets lost in our industry amidst a few too many hard boiled narratives of idealism and progress (the forward-arrow kind). They’re unsettling because they feel not not-quite-human.

When we make them feel something we carve out a space for something else in between ‘all of that.’ A space that’s a bit softer, with less hard edges where software doesn’t even have to feel like software. It can be fun. It can be playful. Both for what it is and what it lets you do. So much so that we can make ourselves feel at home in it. 

It can be fun. It can be playful. Both for what it is and what it lets you do. So much so that we can make ourselves feel at home in it. 

After all, we spend so much of our life online these days. For better or for worse. For the internet to move forward as anything less feels lacking to me.  

9. In some ways make them feel something takes itself less seriously than most …we’re just trying to make it all a bit more fun. 

In other ways it takes the work that we do far more seriously. It requires that the work we do be an expression of ourselves. That’s a lot to give. 

And there’s no beating around it, that what we’re doing is hard. And we have no idea if it's going to work. We really think it will, and we’re going to give it all we got. Pounding the rocks with chisels over and over again until we find the place where the creativity pours out and the pieces fall into place. 

But, in the case that you forget everything else. Or in the case that we’ve got it wrong, let’s get one thing right. At least for the time being and while we can, let’s make them feel something…  It’s all anyone remembers anyway.

_________________
Fig 1. Almost Famous
Fig 2. The Blues Brothers
Fig 3. Rain Man
Fig 4. Thelma & Louise
Fig 5. Easy Rider
Fig 6. Little Miss Sunshine
Fig 7. Dumb and Dumber
Fig 8. Crossroads
Fig 9. The Motorcycle Diaries
Fig 10. The Muppets Movie
Fig 11. Mad Max: Fury Road
Fig 12. Easy Rider
Fig 13. Stranger Than Paradise
Fig 14. On the Road
Fig 15. Planes, Trains & Automobiles
Fig 16. The End of the Tour
Fig 17. Magic Mike XXL
Fig 18. Pee-wee's Big Adventure
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