Sam Strickberger

We thought it would be easy.

2026

We started July with the Fourth, a celebration of American independence. We ended it with Tisha B'Av, the saddest day in the Jewish calendar – a day that commemorates the destruction of the First and Second Temples and the loss of sovereignty. These days mark contrasting national moments. There's freedom lost and freedom gained.

Hope sustains movement from one to the other. It's the belief that, as one philosopher puts it, "together, we can make the world better." But hope alone isn't enough. Great projects often begin because people underestimate how difficult they will be.

When the Founding Fathers chose to break from the world's dominant power and "institute new Government," I'm not sure they understood how hard governing would be. Self-evident truths are not self-realizing, and the pursuit of a "more perfect union" remains unfinished. Likewise, when the ancient rabbis began recreating Jewish life, transforming a religion of an altar in Jerusalem to one of the home and synagogue, they could not have imagined that the road back to self-determination would take nearly two thousand years. Had either group seen reality clearly, they might not have started.

"We do this not because it is easy, but because we thought that it would be easy," reads a flag above Keller Cliffton's desk. Keller co-founded Zipline two years after undergrad to make logistics instant and autonomous, beginning with blood and medicine deliveries in Rwanda. Today, he operates the largest commercial drone-delivery system in the world. His flag flips John F. Kennedy's 1962 moonshot declaration: "We choose to go to the moon…and do the other things, not because they are easy, but because they are hard." Kennedy went to the moon because it was hard; Clifton runs the skies because he thought it would be easy.

This inversion captures how ambitious projects often begin. Or at least those of many young founders, first-timers or outsiders who misjudge the scale of their challenge. It's naivety that enables bold swings. Those who are sufficiently time-rich to keep swinging and smart enough to find the ball eventually make contact. And sometimes these hits are massive (please see: Zipline, American democracy, rabbinical Judaism, and the Knicks).

Flag: We do this not because it is easy, but because we thought that it would be easy

This is where the Dunning-Kruger effect falls short. The usual interpretation dismisses those with limited competence and high confidence – a position referred to as Mount Stupid. But it misses one gift of the summit: a view of the Promised Land when others see only despair or impossibility.

The opportunity of investing in young builders is discerning who makes it well beyond Mount Stupid, while still benefiting from it. We've followed a founding pair for the last few years. They were brilliant and fanatical about an overlooked category but admitted that they knew almost nothing about the specific problem area when starting. They've since become experts and built the category-leading team, generating significant revenue in a market most founders avoid.

I don't believe ignorance is a virtue. But a certain form of ignorance is bliss. And that naivety, along with hope, begins what obsession, persistence, and self-awareness can successfully finish.