Point It Downhill
Caution keeps you safe. Commitment makes you great.
“Go That Way, Really Fast. If Anything Gets In Your Way... Turn.” — Charles De Mar, Better Off Dead (1985)
I’m writing this from Aspen. Wednesday morning, watching it dump snow outside the window.
Lisa and I are here for our third annual Sugar Capital LP event, spending the week with our best friends the Moatzes. Lisa would rather be somewhere warm, she always would, but she showed up anyway. Juliet and Elle have the week off school, so the whole family made the trip. Katie joined us on FaceTime from Wake Forest, grinding through internship cover letters while her sisters learned to ski. Everyone at their own pace. Everyone figuring out their slope.
Eight inches of fresh powder fell overnight. As we left for the gondola this morning, Krista gave Lisa a ride to the airport. By the time we were on the mountain, Lisa was in the air to a conference in LA. She braved the cold all week and left on the best powder day. That’s why I love her.
It was Elle’s first powder experience ever. I watched her go back to pizza every time the terrain got heavy, find her edges, then push through again. We skied down to Bonnie’s for their world famous pancakes, where Uncle Aaron and Nate met us. Then the four of us headed back up. By the end of the morning Elle was pointing straight downhill through eight inches of fresh snow like she’d been doing it her whole life.
That’s when I realized the best startup framework I’ve ever encountered wasn’t in a book, a pitch deck, or a board meeting. It was right there on the mountain.
Every ski instructor in the world teaches the same two things first.
Pizza. French fries.
Pizza is a wide wedge, tips together, fighting the mountain. French fries are skis parallel, pointed straight downhill, trusting it. One is survival. The other is commitment.
Parallel is a decision.
Not a drift, not a feeling, not something that happens when it finally feels safe. It never feels safe. At some point, on some ordinary Tuesday, you bring the skis together, you point downhill, and you commit. The pizza is over. You’re in it now.
The pizza phase is real and necessary and nothing to be ashamed of. Every great company has one. The founder who personally called every customer for the first year before building a sales team wasn’t wasting time. They were learning the mountain before it taught them something worse. The wedge isn’t weakness. It’s the price of admission.
The mistake most first-time founders make isn’t that they pizza. It’s that they’re ashamed of it. They watch other founders shredding downhill in perfect parallel and think they’re behind. They’re not. They’re just earlier. But, and this part matters, stay in the wedge too long and your legs give out. The energy you spend braking is energy you’re not spending building.
The permanently cautious founder doesn’t fail dramatically. They just slowly stop mattering. They hedge every decision, take the safest line on every slope, and one day look up to find they’ve spent three years on the bunny hill while the mountain waited. It always was open. They just never pointed downhill.
Caution is a strategy. It just has a low ceiling.
Every company has french fry moments, and they are the moments that define you. The price increase you know is right but keep modeling instead of making. The hire you’ve been circling for six months. We once told a founder to price her beauty brand below every competitor on the shelf. Everyone in the room hesitated. Her margins were strong enough to absorb it. Her product was good enough to make customers come back and buy again.
We said point it downhill.
She did. It worked.
Control at speed is a different skill than control at slow. At slow, you approve every decision. At speed, you’ve built something that makes the right call without you. It isn’t the absence of fear. It’s fear reorganized into technique. That distinction took me years to understand.
Every new slope resets you. The founder who mastered direct-to-consumer hits the mogul field of wholesale, where shelf placement, buyer relationships, and reorder metrics have nothing to do with anything they built before. You pizza for a minute. You read the terrain. You bring the skis back together. Same founder. Different mountain.
The expert and the beginner both pizza on a new slope. The difference is how long they need to.
Nobody learning to ski is thinking about the view. They’re thinking about their feet. And then somewhere around the third or fourth day, something opens. You stop staring at your tips. You start seeing the run ahead, where it bends and opens. It was always there. You were just too scared to look up.
Fear never goes away. It just changes form. First it keeps you alive. Then it keeps you small.
That’s the whole game. Not the fundraise. Not the valuation. The willingness to go parallel when every instinct says wedge. The ability to reset without crying about it when the slope changes.
Elle figured that out this morning. She just kept resetting, kept finding her edges, and eventually stopped thinking about the terrain altogether. Eight inches of fresh snow, pointed straight downhill, fully committed.
That’s what’s waiting for you on the other side of the decision you’ve been circling. Not safety. Not certainty. Just the mountain, and you, finally moving.
Point it downhill. Trust your edges. And when the slope changes, because it always does, go again.