Dancing on Knife's Edge

On startups, friendship, and the strange mercy of not changing a thing

Earlier that morning, we left Lake Wanaka and its solitary submerged willow. Jamie, Seth, and I had lounged amid fields of lavender, counting shooting stars. The trick was you needed to let your eyes rest. If ever you focused too hard, the streaks that shot past your periphery would be lost to time.

Seth now rummaged through bags of nuts and half-eaten convenience-store sandwiches. Food was fuel. I sat in the front seat of the car, flipping through the songs that would define that vacation: R.E.M., Bleachers, Jacob Collier.

Jamie stopped at an intersection. He looked both ways, and the windshield wipers turned on again. “Dammit, where the hell are these New Zealand turn signals?”

Seth and I raised our hands and shouted, “Opa,” and began cackling with mirth.

Jamie shook his head in chagrin, then made the turn just a hair too tight. Clunk, clunk. He slammed on the brakes. A rogue side-view mirror lay in the road behind us, and Jamie was already reaching for our insurance papers.

Seth and I stood on the side of the road as Jamie argued with insurance agents, and Seth turned to me and asked, “Would you do it over again? Would you change anything at all?”

“About the accident?”

“No,” Seth said thoughtfully, “About your company, StartPlaying.”

“Well that came out of nowhere.”

He smiled wanly. Seth was pensive this trip. He was planning on making a big decision.

“Let me tell you a story Seth. It’s about the three talks at YC I remember…”

Seth leaned against the car and settled in.

I should be careful here because the YC talks I loved were old YC. Kind of like how some people love old Kanye. There were two talks by Michael Seibel and one by Brian Chesky.

The first talk was at nine PM. We’d just finished being preemptively eulogized by Michael Seibel in absentia. And out comes Brian, Joe, and Nate. They talked about being cereal entrepreneurs. About an angel investor who silently slurped smoothie throughout the pitch. And then literally in-person ghosted them, standing up and leaving without a word.

The second talk was on product development cycles, where Seibel enumerated the elaborate jousts the early Twitch team would have. Their constant debates. Their loggerhead product discussions. The symptoms that seemed so easily avoidable, that became manifest at Start Playing the second we had real customers.

But the talk I remember the most is the one Seibel gave on the founding of Twitch.

He talks about how Justin was arrested. How they almost lost all their money on mortgage-backed securities during the financial crisis. And how they came close to dying again and again, even after building a business that made millions of dollars.

He was asked countless questions afterward, tactics and brown-nosing, forgettable as the rest. But there was one that stood out: “Would you do it over again? Would you change anything at all?”

No. He wouldn’t go back. He wouldn’t change a thing.

“We were dancing on a knife’s edge throughout the entire journey of StartPlaying. And if I butterflied an eyelash, our house of cards may have come tumbling down.”

“So no, I wouldn’t go back and change a thing. We were damned lucky to make it out the way we did. To build a profitable business, let alone a profitable Dungeons & Dragons business.”

The car pulled to a stop at our destination: Kawarau Bridge, the home of bungee jumping. Seth smiled and clapped me on the shoulder. I was up first.

I strode out onto the bridge, confident that I appeared confident, at least.

Skydiving, roller coasters, and the running of the bulls have such a frenetic intensity. A rickety plane held together by duct tape makes a cacophony of noise. There’s too much activity to be afraid. Too much romp to hold focus.

Bungee jumping’s different. It’s like a good horror movie. You walk out there, and it’s quiet.

Your mind flits to the birds, tweeting, soaring, and diving, or to the sound of the distant river below. And then the attendant politely but insistently asks you to jump on the count of three. You jump, or you stand there, wait till four, and the platform you’re on drops from underneath you.

Either result is the same. You plummet.

You see this all the time in life. A “pip”. An unfaithful marriage. An exploding offer. Either you make a decision, or the decision is made for you. The outcome is the same either way.

But I take pride in knowing that I jumped.

Swish. Shwah. A blur of blue. A tug. And a gentle bounce.

We sat again in the car, exhilarated. Seth finished packing up. And we sped off down the road to begin the Routeburn Track.

“So you wouldn’t do it all over again, huh?” Jamie joined the conversation.

“Nope.”

I lounged in the back, letting my heartbeat settle down from its peak at 170.

“But it all worked out, you know?”

“Yeah. And?”

“Well, maybe if it didn’t all work out in the end, maybe you would go back. Maybe you would change something.”

Clunk, clunk.

“Did you hear that?”

Jamie looked up toward the roof of the car. “Yeah.”

Seth checked the mirrors. “I don’t see anything.”

“Maybe we hit a stray kiwi.”

Seth tapped on my shoulder. “Ah it’s nothing, just put on some tunes.”

He reached over into the side cup, his hand feeling around. “Where’s my phone?”

I looked over. I didn’t find anything.

There must’ve been three or four heartbeats of silence. That beautiful calm before the storm, hearing the wind rush past and the tires roll on paved ground.

“Shit.”

Seth used to have a habit of putting his phone and wallet on top of the car while he was fiddling around with the trunk. This time he forgot to grab them when he came back in. The wallet and phone flew off the car as soon as we hit the highway.

We got out and began looking in the ditch for whatever might remain of an iPhone, driver’s license, and credit cards.

“Have you ever heard of the three Viennese schools, Jamie?”

Jamie sighed and settled in to listen as he looked.

There were three great teachers in the tradition: Freud, Nietzsche (through Adler), and Frankl.

Freud proclaimed will to pleasure. Man is hedonic and seeks and strives but for the sake of his own pleasure. Even altruism is but a selfish act.

Nietzsche followed suit with will to power. “...to recreate all… until the will says, ‘Thus I willed it!’” Thus Spoke Zarathustra.

Frankl believed in will to meaning. He was a Holocaust survivor. He lost everything: his family, his health, his manuscript, his work. He was all but erased from history.

In a world of youth fetishization, of new YC, where the average age of startup founders is precipitously dropping, it’s easy to overvalue potentiality. We look upon the youth and say, “They have such potential. They can be great and good. They can get a million followers on X or raise at a billion-dollar valuation.”

So we undervalue, we nearly abnegate experience and the past. But the past can never be taken away.

“StartPlaying made me who I am today. Regardless if it’s good or bad, it’s my past. It’s part of me.”

Jamie heaved his backpack onto his shoulders looking up at the mountain we were about to climb, “Let’s go.”

The Routeburn Trail was the climax of our trip. One of the best hikes in the world. Densely vegetated. Rolling New Zealand greens. And up, up, up it went, until by the end we stood upon a peak that would make even Gandalf turn to go under the mountain.

It was beautiful. It was quiet.

I had just gotten new hiking shoes, and I thought I had been diligent. I’d spent a couple of days walking around San Francisco breaking them in. And I felt sure twenty to thirty miles of walking was a good test of function.

While San Francisco is hilly, yes, up and down it goes, Routeburn is mountainous.

The backs of my booted parts immediately began to blister. Small rubbing burn marks at first. Translucent bubbles later.

Fortunately, I brought moleskin. But unfortunately, I didn’t know how to appropriately use them. I cleansed and applied it at night. And out of undue diligence, I decided to reapply. I ripped it off, tearing off both mole and human skin.

By the end of the trail, every step shot lines of searing pain up my legs. And I switched from hiking boots to running shoes that gave more give to my freshly vulnerable Achilles tendons.

As we finally summited, there was a storm. The Routeburn closed. I silently thanked the gods. And began the luxurious downhill clomp back to our car. The pressure now blessedly on the fronts of my feet.

We pulled the car over along the side of the road to a tree that offered shelter in a savannah of neat crops. We sat there on a precipice. On a knife’s edge.

Trying to understand what we should do next in life. With start-ups, with family, with love.

“Okay, Nate, final question.”

“Final answer.”

“So even if Start Playing hadn’t worked out, you say it made you who you are. Well, what about this? The trip was a disaster.”

He was right. Almost nothing had gone according to plan. Jamie still had an angry New Zealander with a broken mirror to deal with. Seth spent the next month renewing his driver’s license and canceling all of his credit cards. And for me, it would be a month until I was walking normally again.

“So tell me, would you really not go back and change anything about our little adventure?”

I smiled. “You know what? I would go back.”

This was probably the last trip we ever had together. Seth would leave San Francisco some years later. And the tight-knit friendship that bound us through fifteen-mile hikes and mile-long swims would slowly loosen.

“I would go back. But to relive everything. To spend that night putting together shitty sandwiches in the hostel. Driving on the left side of the road. Rocking boy-band T-shirts. Jumping off a bridge. Goofing around on the funicular. Getting splashed by the icy fjord water. And even hiking with the backs of my feet raw. Talking, whining, riffing, complaining. Prevaricating and equivocating on all those decisions we’ve yet to make.

“I would go back again. I’d relive the whole thing. I’d relive it all.

“But I wouldn’t change a thing.”