Waiting for Waves

Founder vision is bullshit. Sort of.

Most startup stories are told in retrospect as if the outcome was obvious.

This idea worked.
The timing was right.
The founders saw it coming.

That’s not how it happens.

In the early days, you’re not riding a wave—you’re waiting for one. You sense the swell, which is why you start the company. But you’re often stuck in the water, fundraising and iterating and waiting — for the first big waves to arrive. Sure you might catch some small ones, but those are boring. Disappointing. Frustrating.

As for the big ones that came before? Someone already caught those. They left you in the dust. You watch their rides with envy. Or numbness. Or a jaw-clenched turn back to the horizon.

So you’re paddling, guessing where the wave might form, betting you’re pointed in roughly the right direction when it does. And you’re hoping some of your fellow surfers who are also still waiting get frustrated and swim in to shore.

Waves are inflections

At Bonobos, we sensed a swell.

In 2007, men’s e-commerce was only 7% of total retail but growing quickly. Apparel was starting to move online. Larger cohorts of men were beginning to care more about fit and style.

These were all important consumer waves—or what, in startup parlance, are called inflections. (Mike Maples Jr.’s book Pattern Breakers offers the best primer I’ve seen.)

But those consumer inflections weren’t yet matched by the technology, distribution, and infrastructure inflections required for Bonobos to work at scale.

Instagram hadn’t launched yet.
Facebook’s ad platform wasn’t live.
Smartphones and mobile shopping weren’t a thing.
Shopify hadn’t arrived yet.
3PL infrastructure was limited.
Venture capital wasn’t investing in the category.

Those developments—and the behaviors they unlocked—ended up being table stakes to what we built. It looked like maybe we knew what was coming.

We didn’t.

You can’t see them all coming

I was just as pleasantly surprised as you were the first time I saw Instagram filters.

Visual storytelling. Scalable customer acquisition (for a time). Lower friction commerce. None of them were part of the original plan. Because they didn’t exist.

There is no original plan that matters.

Luckily for me, at 28, I wasn’t even aware I was waiting for those inflections. I was too dumb to know that was how this worked.

We got the bet right on the customer. But betting on the ecosystem that follows the customer?

That was intuition and faith alone.

The cool thing I’ve learned is the ecosystem tends to follow the customer — forming and proliferating around where they’re headed…

When Facebook launched their ad platform, we had built a relationship to be one of the first 50 brands on it. We found the 3PL that was distribution for Zara and we talked our way in. We led a movement of DTC brands raising capital from venture by identifying the few that were open to it and converting them. We were too early for Shopify and we suffered a lot of time and energy trying to do it ourselves. We did a passable job at Instagram but didn’t take advantage of that inflection in the right way.

We didn’t hit all the waves right. But we hit a bunch of them.

That’s the truth about startups: success usually requires a stack of inflections. Some you see that lead you to jump in. Some you sense that keep you afloat and excited. Some you were too cool to predict and then they show up and change everything.

You hear this in hindsight stories all the time.

Game changing waves are only obvious in retrospect

Uber is the canonical example. People say it was “made possible by GPS on the phone.” Maybe that’s true. Or maybe the idea came first and GPS on smartphones made it viable at scale. The causality is blurry, which is kind of the point. I don’t know the history. Some of you do. The point is this:

The founders were betting that a set of technological and behavioral shifts would converge: smartphones, location awareness, mobile payments, density, trust.

It wasn’t one wave. It was several, arriving close enough together to matter.

A favorable swell.

When you’re early, this creates a strange tension.

On the one hand, you need conviction. You need to believe the future you’re building toward is real. You have to make decisions as if the waves are coming.

On the other hand, you’re often early enough that reality hasn’t caught up yet. Customers sort of get it. Or don’t. Infrastructure is half-there. Behavior is inconsistent. The thing works, but only barely. Or in the corner. There’s a product inflection, but no distribution inflections.

So you wait.

You ship.
You iterate.
You do okay.
You explain yourself a lot. Often to yourself.

And you wonder whether you’re early… or just wrong?

(Wrong can be early. And wrong can also become right later if you switch to right.)

Winning is nine parts preparation and one part vision

The best founders aren’t the ones who perfectly predict the future. Because those founders don’t exist.

They’re the ones who position themselves to benefit from multiple possible futures, and then stay alive long enough for one of them to arrive.

They notice some inflections clearly. They bet on others implicitly. And they remain open to the ones they couldn’t have named in advance.

That’s what waiting for the wave actually looks like. It’s less surfing and more treading water with intent.

Which brings me to Pie.

I won’t unpack it here. Partly because it’s still unfolding. Partly because you don’t know which inflections matter most until after the fact.

But something is changing in the water. I can’t wait to tell you more when I can with enough hindsight to know I’m not blowing smoke.

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Founders:

If progress feels slower than it “should,” it’s worth asking a different question than what are we doing wrong?

The better questions might be:

What waves do we see coming?

Are we positioned to catch a set when it arrives?

If we do, who can we delight? And who might we become?

Most overnight successes are built by founders who jumped in based on early inflections they observed, paddled towards inflections they saw coming, and won because they were ready to take advantage of the ones that blew everyone away.

They were the most prepared to get the most lucky.