The Hidden Cost of Being Right Too Early

There’s a particular kind of frustration that only entrepreneurs understand.

You see something coming. You’re convinced it’s going to change the way people live or work. You build a company around it. And then you wait.

And wait.

Not because your idea is wrong. But because the rest of the world isn’t ready for it yet.

We love to celebrate founders who were ahead of their time. We tell their stories with the benefit of hindsight, connecting the dots between an unlikely idea and an inevitable success. What we tend to leave out is everything that happened in between.

The years spent convincing skeptical customers.

The money spent educating a market that doesn’t yet understand why it needs your product.

The constant pressure to distinguish between a vision worth pursuing and a bet that simply isn’t working.

Being early is often celebrated as a competitive advantage. But being too early can be just as dangerous as being wrong.

It’s a tension I’ve experienced firsthand, and one that came up in a recent conversation with Stephanie Cartin, cofounder of Socialfly and Entreprenista, on Breaking Precedent.

Stephanie had recognized the opportunity years earlier, while studying marketing at Cornell. She believed social media would fundamentally change how businesses reached customers.

“We know this is coming,” but “Sometimes we’re too early,” Stephanie told me on Breaking Precedent.

She was right. But she was also early.

In some cases, she explained, it took the broader market four years to catch up.

Four years is an eternity when you’re running a startup.

When I launched TaskRabbit in 2008, the idea was straightforward: connect people who needed help with everyday tasks to people willing to do them. But the world wasn’t yet accustomed to hiring someone through an online platform to assemble furniture or run errands. Smartphones were just emerging, and the gig economy wasn’t part of our everyday vocabulary. There were trust issues.

We weren’t simply introducing a service. We were asking people to change how they thought about getting things done.

And changing behavior is expensive.

When customers already understand a category, you can focus on why your product is better.

When you’re creating a category, you first have to convince them the category should exist.

That means more education, more resources spent building trust, and potentially years before mainstream adoption. Worse, you can spend years educating a market only to have competitors arrive once customers are finally ready. Sometimes number two is the strategic advantage.

Stephanie and Courtney did something smart before quitting their jobs. They spent ten months building Socialfly on the side, signing early clients who paid a few hundred dollars a month.

They weren’t waiting for the entire market to embrace social media. They found customers willing to pay for it now.

As an investor, I want founders with a compelling vision of where the world is heading. But I also want to know how they plan to stay in business until that future arrives.

Who needs the product today? What assumptions have been tested? And what happens if adoption takes twice as long as expected?

Socialfly grew without venture capital, relying on customer revenue and later selective borrowing to finance expansion. That approach required Stephanie and Courtney to build around existing demand rather than anticipated demand.

Venture capital can be a powerful tool. I’ve experienced that firsthand.

But capital doesn’t make a market ready.

It buys time, and time is only valuable if you’re using it to learn, adapt, and build something customers want.

We tend to think of startup timing as luck. A founder launches when technology, consumer behavior, and market conditions align. But entrepreneurs can also manage timing.

You can start with a smaller market that’s ready today. Test assumptions before committing significant capital. Generate revenue while the larger opportunity develops.

Stephanie didn’t need every business to believe in social media in 2012. She needed enough businesses to believe in it to keep Socialfly growing.

For founders building around AI or any emerging technology, the question isn’t simply whether your prediction about the future is correct.

It’s whether you can build a viable business today.

Being right too early only matters if you’re still around when everyone else realizes you’re right.

This week’s essay pairs with our latest episode of Breaking Precedent, where I sit down with Stephanie Cartin, cofounder of Socialfly and Entreprenista, to explore what it takes to build a business before the market is ready for it. We talk about betting on social media when businesses still dismissed it as a fad, the challenge of convincing customers to embrace something new, and how Stephanie and her cofounder built a successful agency without venture capital. It’s a conversation about timing, conviction, and why being early only matters if you can stay in the game long enough.

Thank you to our Precedent Breaking Partners, Justworks, Taskrabbit, and SquaredAway, for supporting this season’s conversations.