Building a Startup Is a Marathon. Are You Pacing It Like One? 8/27/2026

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📰 Today's Edition: Building a Startup Is a Marathon. Are You Pacing It Like One?

End of summer. How are you actually feeling?

Not the answer you'd give at a networking event. Are you going into Q4 sharp, or are you already running on empty after months of heads-down building? Most founders won't admit the second one out loud, but a lot of them are living it. The grinding startup culture makes it feel like slowing down is falling behind, so people just push through, and push through, until something breaks at the worst possible moment.

There's a former Olympic runner named Jeff Galloway who figured out that the fastest way to finish a marathon isn't to run the whole thing. He started building deliberate walk intervals into his races, not because he was tired, but because the data showed it produced better finishing times than running flat out. 

When you sprint continuously, fatigue accumulates faster than your body can manage it, and by the time you hit the miles that actually demand something, you have nothing left. The walk intervals keep you fresh enough to push when it counts. It worked well enough that he now coaches thousands of runners on the same method.

Building a company works exactly the same way. 

What does hitting a wall actually look like?

It's rarely the dramatic collapse people imagine. More often it's a slow degradation that's hard to see from the inside. Your judgment gets worse but you don't notice because you're too tired to notice. You spend more time reacting to whatever's loudest rather than thinking clearly about what actually matters. Decisions that should take twenty minutes take three days. You're technically working but not really moving anything forward.

Startups have moments that require everything you've got, a tight fundraising window, a product launch, a critical hire, a make-or-break customer conversation. When those moments come, you need to be sharp. If you've been running at full capacity since January without a real break, you won't be. 

The people who build great companies over the long run aren't the ones who logged the most hours. They're the ones who had enough in reserve when the race actually demanded something.

Why is real rest so hard to actually take?

Because most founders don't know how to do it. They book a trip, they physically leave, and then they spend the whole time half-checking Slack and telling themselves they're just keeping an eye on things. They come back not feeling rested because they were never really gone. It's like Galloway's runners trying to "walk" while still jogging, you don't get the recovery benefit if you never actually stop.

There's also something worse: if you feel like you can't leave your company for a week, that's a sign something is structurally broken. A company that falls apart the moment the founder steps away isn't a company yet. Building a team and systems that can hold things together without you for a few days is part of building something that actually scales.

At Hustle Fund, the team grades each other on how well we vacationed. It sounds a little absurd but it exists for a real reason, because the default without accountability is to not actually disconnect at all. Vacationing well means getting off the grid: no email, no Slack, no "just a quick check." It means resting the mind, not just changing your physical location. You don't even need to go anywhere. The point is the disconnection, not the destination.

End of summer is a natural moment to take stock of this. Q4 tends to be when things accelerate: fundraising picks back up, enterprise deals start closing, hiring pushes happen. You want to be going into that stretch with something left in the tank, not already depleted from a long summer of grinding with no real break. If you haven't taken one yet, even a few days fully off the grid still does something.

What does this mean for your team?

This is where a lot of founders drop the ball. They might take a break themselves but let the culture quietly celebrate the people who don't. Someone works through their vacation, checks in constantly, and comes back having never really disconnected, and if you acknowledge that positively, even in passing, you've just told everyone else what the real expectation is.

A burned-out team makes worse decisions and moves slower, and the cost compounds in ways that are hard to see until you're already behind. Holding your team accountable to actually resting isn't a soft, feel-good thing, it's a productivity call.

The teams that pace well consistently outperform the ones that sprint until they break, recover, and sprint again. At Hustle Fund, grading teammates on how well they vacationed is a way of making that accountability explicit rather than hoping people figure it out on their own.

How do you actually build this into how you work?

The mistake is waiting until you feel like you need a rest to take one. By that point the damage is already done and you're making decisions from a deficit. Galloway doesn't build walk intervals in at mile 20 when his runners are already dying,  he builds them into the plan from the start. The better approach is to schedule rest the same way you'd schedule a product sprint or a fundraising push, deliberately, in advance, as part of the plan rather than a break from it.

For your team, make it explicit. Talk about it. Make "vacationing well" an actual expectation rather than a nice-to-have. Check in with people about whether they've actually disconnected, the same way you'd check in on a product milestone. The founders who build sustainable companies treat their team's capacity as a resource to be managed, not an infinite well to draw from.

Q4 is coming. It's going to move fast. The question is whether you and your team are going into it rested and ready, or already running on fumes before the real miles even start.

Until next time,

Dunky, the "vacationing" hippocorn

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