For my life’s work, I’m going expedition-style

When I meet aspiring startup founders, I’m struck by how many of them quickly abandon their ideas and pivot to something totally different. Sometimes the pivot is relatively small, like a different type of product for the same persona they were already targeting. Other times the pivot is huge, like switching from B2B infrastructure to building a dating app. One founding team tried 15 startup ideas across diverse domains in 21 months. 

For these nimble folks, it feels like their main goal is to found a successful company, any successful company. While they might have strong values for the type of company they want to create, the subject matter is less important to them. Or maybe they need to explore a bunch of directions to discover what they want to work on.

Not being committed to a specific product vision comes with advantages. It allows you to see things unemotionally. You can test products in different markets until one of them swiftly takes off.

I’m in a different bucket. I founded DoubleLoop not because I wanted to be rich or run a successful company (although I wouldn’t mind). I founded DoubleLoop because I envision a better way for people to build software. To make my vision come true, founding a startup is a means to an end. While my mental model for how to proceed changes frequently, nothing will shake me from what I originally set out to do. It’s my “life’s work.”

Ever since I randomly watched Free Solo on an airplane, I’ve had an obsession with mountaineering films. The documentary is about Alex Honnold’s quest to “free solo” the steep face of El Capitan; that is, climb perilous heights without a rope.

In one sense, free solo climbing is the exact opposite of what I choose to do. I like endeavors with massive upside and minimal downside. By launching a startup, I’m expected to fail because most of them do. Failure would be painfully disappointing, but not ruinous. But if I succeed, it will be literally like my dream came true (at least I hope it will be like that). With free solo climbing, in contrast, the downside is extreme. If you make a mistake, you fall to your death or get seriously injured.

Despite the differences, I have one big thing in common with climbers like Alex Honnod: a fixation on a singular goal. Observing an exemplar of the “never give up” attitude makes Free Solo both entertaining and illuminating.

After watching Free Solo, I proceeded to devour a gamut of popular mountaineering movies including Meru, Sherpa, Touching the Void, The Summit, Beyond the Edge, and notably Climbing Blind, the story of a climber whose lack of vision doesn’t stand in his way of tricky ascents.

It’s both a blessing and a curse that I’m rarely capable of consuming media purely for its own pleasure. I watched these films, in part, to plumb the discipline of mountaineering for metaphors to apply to my monomaniacal DoubleLoop quest.

As I had hoped, an interesting distinction popped out between alpine-style and expedition-style mountaineering.

Alpine-style is when you pack the bare minimum supplies needed to go straight up and down the mountain, in one strong, lean, fast push.

With expedition-style mountaineering, the team invests more upfront to maximize the odds of success. They set up several camps on the way to the summit, repeatedly going up and down the mountain to bring supplies to higher camps.

Alpine-style route to climb K2 (
Camps for climbing K2 expedition-style (

Expedition-style mountaineering connects with my experience building DoubleLoop. Early after conceiving the idea, it became clear that there was no alpine-style route to the summit. I set out to create a world where software builders could learn from their predecessors through vivid historical records of past learnings, successes and failures. People liked the idea and signed up to try it. But after compelling my engineering friend to build a primitive version of the product, few folks were willing to spend the effort to actually build historical records in DoubleLoop.

DoubleLoop was my side project and I wasn’t in a position to quit my day job to do it full time. Given that my first attempt to get customer traction didn’t take off, it was clear that I had a big mountain to climb to make the vision real. But I’ve kept climbing. I still have a long way to go, but every month I get closer to the summit. I’m now full-time on DoubleLoop with talented technical partners, paying customers, and like-minded investors.

When you approach a mountain expedition-style, you don’t ascend with immediate ambitions of the summit. Your first goal is to establish a series of camps incrementally higher up the mountain. These camps are connected with fixed rope lines that make it feasible for the team to repeatedly ascend and descend the mountain. Each camp gets stocked with supplies, food, and oxygen for surviving the high elevation.

With alpine-style climbing, if you don’t reach the summit, you have to head all the way back to bottom. Failed attempts don’t yield a material advantage that make second attempts easier. You might as well go climb a different mountain.

Expedition-style mountaineering, in contrast, affords your team optionality and the possibility of multiple attempts to reach the summit. You can wait at the highest camp for good weather. If a subset of your team comes up short on a run at the summit, they can head safely down the mountain while another group takes a stab. While expedition-style mountaineering is more expensive and time consuming than alpine-style, it increases the odds that some members of your team will achieve the goal.

Expedition-style, applied to startup building, leads you to think about your company iterations differently. Instead of looking for a direct route to product/market fit, you start make moves with the purpose of positioning your future company for success, like setting up well-stocked camps progressively higher on the mountain.

Alpine-style company builders apply lean startup methodology, racing to validate the killer app. In this mindset, building a platform before validated user demand is waste. They want to show that people want an app before building the platform behind it.

Expedition-style startup builders apply fat thinking. They build platforms that can be quickly re-oriented in the form of different apps as the team learns. It’s relatively expensive and time-consuming. It requires raising venture capital to build a platform before you know what customers will pay for.

Expedition-style builders must drive customer adoption of a wedge product before their ultimate vision is realized. While high-altitude climbers need oxygen, product builders need users for (1) attracting investors and (2) product development feedback loops. As Matt Mullenweg said, “Usage is like oxygen for ideas.”

In mountaineering, a key variable in deciding between alpine- and expedition-style is how far the mountain is from civilization. Mountains nearer to civilization, like in the Alps or Rocky Mountains, lend themselves to alpine-style. The tallest, most remote mountains require expedition-style, like in the Alaska Range or Himilayas.

In choosing what approach to take for your startup, lean or fat, ask yourself the question, “How far is your idea from civilization?

In startup terms, “distance from civilization” is “distance from an established market.”

If your startup idea is an incrementally better way to serve robust buyer demand, go for it alpine-style. Quickly discover if you’re right or wrong.

If your startup requires creating a new market or new user behavior, you need the expedition-style approach. You’ll need many attempts to find product/market fit, so you want to set up “camps” progressively high up the mountain to maximize your odds of ultimate success.

For your life’s work, go expedition-style. There’s only one mountain to climb so spend more to get there. If you don’t make the summit, probably no one else will for years to come.

Mountaineering, obviously, is more dangerous than startup building. But startup building tops mountaineering in levels of uncertainty and ambiguity. While climbers must manage the possibility of unpredictable storms, founding a startup is like heading for a summit without a topographical map. You can’t tell which destinations will be easy or hard to reach until you start moving.

What I’ve learned building DoubleLoop can be expressed as contour lines on a map. I’m learning the coordinates of the highest points with the most customers. I’m setting up the camps to get there.

Both mountaineers and startup builders are looking for the same thing: the global maximum.

Topgraphical map of the DoubleLoop space. Countour lines = friction.

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