Ben Sampson Headshot

Hey, I'm Ben!

I build, buy, and invest in businesses.

I've had 2 successful exits. Way more failures.

I send one action packed email a week called a 1x1x1 covering crazy cool businesses I spot, updates on what we're building and buying, and lessons from the journey of an entrepreneur.  

My current projects:

Luna

Accredited

Pono Ventures

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Ben's 1x1x1 - The Trough of Sorrow - June 12, 2026 🚀

For those of you that are new here, every week I send what I call a 1x1x1.

One thought from my week.
One interesting find/tool from my week.
One image from my life.

Let's dive in 👇

Thought from the week

Every entrepreneur eventually finds themselves in what Paul Graham calls The Trough of Sorrow.

Revenue isn’t growing fast enough.

Customers aren’t showing up.

The product is taking longer than expected.

Expenses are somehow higher than expected (they always are).

And you start questioning everything.

Last week was one of those weeks for me.

I was in the trough.

We weren’t seeing the traction I wanted with Luna.

Like multiple days with 0 new signups.

Entrepreneurship creates these wild emotional swings.

Monday: “We’re going to change the world.”

Thursday: “Maybe I should become a park ranger.”

After enough years of building businesses, I’ve learned that the goal isn’t avoiding the trough.

The goal is learning how to climb out of it faster.

Today I wanted to share a few tricks that consistently get me out of the trough:

Find someone 3-5 years ahead of you

When I’m stuck, I go find people who have already solved the problem I’m facing.

Last week I spent time talking with founders building consumer apps.

People who have the scars.

People who have made the mistakes.

People who have been exactly where I am.

Sometimes their feedback hurts.

Good.

Painful clarity is way better than comfortable confusion.

Create small wins

One of the hardest parts about building a company is that it feels like a project that never ends.

There is always another feature.

Another bug.

Another campaign.

Another goal.

I’ve found it helps to create bite-sized projects that can actually be completed.

Finish something.

Ship something.

Cross something off the list.

Momentum is a powerful antidepressant.

Spend time with other founders

Media is a highlight reel.

You see the acquisition.

You see the funding announcement.

You see the milestone.

You rarely see the three years of stress, uncertainty, and wondering if the whole thing is going to work.

Most entrepreneurs are fighting battles nobody knows about.

So talk to other builders.

Be honest.

Tell them where you’re struggling.

The fastest way to feel less alone is realizing you’re not alone.

Have a side project

I love side projects.

Not because they make money.

Most don’t.

I love them because they’re playgrounds.

Places to experiment.

Places to learn.

Places to get quick wins.

Sometimes a little momentum from a tiny project is enough to get your confidence back in your main one.

Zoom out

This is the big one.

Most of the pressure we feel comes from goals we created ourselves.

Deadlines we invented.

Expectations we made up.

That doesn’t mean they aren’t important.

But it does mean they’re not life or death.

When I’m in the trough, I try to zoom out.

Maybe this week wasn’t great.

Maybe this month wasn’t great.

But compared to five years ago?

Ten years ago?

Life is pretty incredible.

Progress is easy to miss when you’re standing in the middle of it.

Business is a long game.

A really long game.

The peaks are fun.

The troughs are inevitable.

Last week I found myself sitting squarely in the Trough of Sorrow.

This week I’m back to building.

And if you’re currently in your own trough…

Keep going.

You might be a lot closer to the next peak than you think.

Image from my life

Another week wrapped 😴

See you all next week!