Did the world's best climber save Timber?

A personal story about perspective after a year of effort put into building this company

One of the best climbers to ever pull on rocks, Chris Sharma, concludes a recent episodes of the new Climbing Gold podcast by Alex Honnold with wisdom about attitude:

You could go to a really crappy, chossy, little boulder .. with the right attitude, good friends, have an amazing time, and suddenly that boulder is transformed into this amazing thing, and vice versa. You could go to a place like … Yosemite and have a bad attitude and it doesn’t matter that you’re in the best place in the world. You transform that place into a bad place.

Depending on your mood this morning, this might be a helpful message or it might be a tired cliché from an action sports adrenaline junky. Even if you’re not a climber, believe me that climbing stories have the bones of good stories. High stakes and interesting characters combine with riveting storylines. Co-host and producer Fitz Cahall has a natural talent for story building. And although some of the recording is rough around the edges, you’ll be on the edge of your seat while you listen.

For me Sharma’s message came at the end of a 48 hour stretch of bad attitude that was taking me to a bad place.

If you’ve been following this newsletter, you know that I thought we’d have our podcast hosting product ready sometime in February. The calendar had just turned over to April making us two months late and a full year into development of a never-ending project. Worse, it looks like it could be who-knows-how-much-longer before we’re really ready. Three months? Six months?

I had been patient for a year, but then I stumbled on a tweet thread by Andrew Wilkinson. Known for inviting outrage on Twitter by saying he was quitting podcasts—despite having venture investments in podcast companies—he wrote a tweet thread about throwing away 10 million dollars of his own money. His thread talks about how he spent years trying to make his software todo list company successful and lost to Asana because they had vastly more venture capital. It has choice lines like, “We were a fart in the wind. Suddenly, Asana ads were everywhere.”

This hit too close to home. Every day I read Podnews and I see other hosting companies land new venture deals. Every million dollars of funding they get is significantly more than we can spend, and recently some hosting companies have gotten three, four, even 12 million dollars. How can we compete? The market is saturated! The service is a commodity! I was looking at all the money we’ve spent so far on software development and on paying writers and thinking about the private college tuition it could have paid for.

I went to a really dark place in my mind. I was imagining the conversation I would have with cofounder Chris Hickman that would lead to firing him and shuttering Timber. About how embarrassing it would be to quit before we even started.

These dark thoughts lasted one full day and I assumed I’d wake up the next day out of my funk. I’m generally an optimistic person! But I woke up the next day feeling worse.

I called Chris.

Before I called him I wrote up two pages of notes that I named after my favorite Succession episode, “Shit Show at the Fuck Factory.”

The notes had sad lines like, “Podcasting has changed since we started,” and “We cannot build a product mote,” and “This thing is just hemorrhaging money and it’s nowhere near enough.”

I said most of these lines to Chris. I did it in almost a pleading tone.

He listened patiently until I got it all out. So for about 2 hours.

Then he said the first of two important things. “We’re not trying to compete with the rest of the hosting companies that are in a race to the bottom. They’re all trying to figure out how to make money selling ads on other people’s podcasts. They’re not our competitors.”

Still that wasn’t enough. How would we find the people that even care whether their podcast is being monetized by Spotify or venture capital vultures Andreessen Horowitz?

The answer is that we just keep talking about it. We tell the story that not one single VC dollar gives a shit about audio, and doesn’t care about creators. No matter how enticing the marketing of those companies is towards creators, the money behind it is singular in purpose.

And then Chris said the second important thing: “You could look at all the money we’ve spent on Timber as a waste of money, and that you’d rather have that money in the bank, or you could look at it as the privilege you have to work on something you care about.”

I stopped pacing and listened. Chris said that either way, if Timber was just too much and I couldn’t do it anymore, I still have a great friend in Seattle.

The dark cloud lifted right at that moment, and I said that of course I wasn’t ready to quit Timber.

Maybe we’re late for our beta, but we’re plugging away. And we’re not cutting corners. We’re over here doing good work.

Later that evening I was driving 75 miles an hour into the sunset after taking my daughter to Walmart to buy Easter toys. I was listening to Climbing Gold. That’s when I heard Chris Sharma say the same thing about climbing as Chris Hickman had said about building a business.

It’s all about the attitude you bring to it.

I’m back in a good place and loving every second I have the privilege to work on Timber.

Thanks for reading! Please consider sharing with people that might like this message and have the patience to bear with us as we prepare our software.


—Jon Christensen