Discover more from Between the cracks

Exploring, one half-baked idea at a time.

#25: Leaving Wren

And what I'm up to next.

Thomas Hollands

Jun 8, 2023

A few weeks ago I made probably the most difficult decision of my life.

I chose to leave Wren.

I loved the work and Wren’s mission, was paid well, the company is growing—and most importantly, I worked with a team of amazing people I am proud to call friends.

Several times I thought to myself: “What the fuck am I doing?”

Here’s some background on how I found Wren, my great time there, and what I’ll be up to next.

Early beginnings

I first heard about “Project Wren”, as it was called then, after seeing hype about them on Twitter in early 2020. Almost immediately, I became a customer.

Back then, I was an unemployed graduate who spent all his savings on intercontinental flights to Canada to visit his girlfriend.

Every time I stepped onto a plane, my excitement in seeing S was tinged with guilt and sadness: following my heart entailed polluting the atmosphere and contributing to climate change. Well before I joined the company, Wren helped me feel empowered to do something about my own environmental impact and make a difference.

I first considered joining Wren in October 2020, after seeing a job posting being shared around Twitter.

I read everything I could get my hands on about Wren (including Landon, the Wren CEO’s early interviews), then I applied. I couldn’t believe the team considered me for the role, and I was so keen to do it: I DMed Landon and the rest of the team “relentlessly”.

Relentless in a good way I hope ???? 😆 (also a friend did not share the interview, I stalked Landon and found it)

It’s hard to emphasize how big of a risk Wren cofounders Landon, Mimi, and Ben took when hiring me. But I’ll try anyway.

At this time in my life, I’d worked 14 different full-time jobs, each one of which I’d disliked and quit within 6 months. I wasn’t ever sure if I would find an environment where I felt comfortable or trusted to do great work. When Wren interviewed me, my biggest achievement was writing a blogpost about the economics of OnlyFans. When they hired me, all I had was a tattered work history, a slightly NSFW blog, and a lot of enthusiasm. I was a risk.

I’m so grateful the early Wren team took that bet on me.

Joining Wren

When I joined Wren we had 1,700 members. 15 new members joined in my first week.

I was in charge of figuring out how to make that number go up. Our growth curve looked like this:

The week I joined Wren we had 15 new subscribers.

I wasn’t sure if we’d ever see weeks with >100 new subscribers ever again. But the team always trusted me to figure stuff out, and together we found a few things that work. If there’s one thing I’m grateful for, its that Wren has given me so many opportunities over the past two and a half years.

From letting me rewrite the landing page on literally my first week on the job, to running paid marketing experiments on over a dozen ad channels, to eventually cracking creator marketing, and spending millions per year sponsoring 100s of creators, including Kurzgesagt and Veritasium, the largest science creators in the game.

Should’ve pushed harder to sign Rebecca Brand tbh

I’ve grown and learned so much in my time at Wren, and it has genuinely been the best job I’ve ever had.

We’ve hit so many accomplishments together—from offsetting over 20k tons of CO2e every month, to raising $5m in venture funding, but if I had to summarise my experience working at Wren, the most important thing I’d mention is the feeling of working with a team of smart, kind, optimistic people.

Here are some things I’ve learned from the Wren team and I’m grateful for:

Curiosity, empathy, and open-mindedness about our users (esp exemplified by Mimi, Landon, Path)
Desire to build a world-class, amazing experience (esp exemplified by Ben, Taylor, Eric, Sophie)
Meticulous attention to detail, which is a prerequisite for making something great (exemplified by Hilary, Sophie, Ben)
Relentlessly caring about what our users want and how they feel (exemplified by Hilary, Taylor, and Ben)
The belief that no matter how difficult something is, we can do it (exemplified by Landon, Mimi, and Ben)
A great attitude and a wonderful sense of humour, and truly caring about Wren’s mission (all of you 😊)

Thanks to the Wren team, the future of the company is incredibly bright.

So, why leave?

The long story short is: I feel I must.

Over the last couple months I’ve been reflecting about what I want out of my life and career.

People opt into different life-scripts. Banker, lawyer, doctor, founder, investor, physicist. You pick an aspirational identity and a well-defined career path, and stick to it.

That approach has never resonated with me. I don’t want to pick a life-script and stick to it. I want to live many lives in one.

At Wren, I had the opportunity to choose the life-script of Marketer. There was a clear path to eventually becoming a CMO. While I enjoy and am good at many aspects of marketing, I don’t want to “be” a Marketer.

I want to try new things, and then keep doing the things I want to keep doing.

So far, here’s what I know about what I want to do:

I want to understand the world better, and help other people by sharing my understanding with them.
I want to turn open-ended problems into closed solutions.
I want to build a network of smart, interesting people (like you, reader) and I want to have generative conversations where I can learn from people like you on a regular basis.
I know that I’m especially interested in climate technologies, the creator economy, and in the ways in which new tech shapes real-world human behaviour.

Where to next?

Remember that interview with Landon I linked about Wren up top? The interviewer, Erik Torenberg, is building a media company, and I’m going to work with him.

Erik’s an investor and podcaster, and I’ve been listening to his podcasts since 2018, back when I was a disgruntled physics student with a pipedream of someday working at a startup—and if I was brave or lucky enough, maybe one day investing in or starting my own.

His new company, Turpentine, launched today.

“Art critics sit around talking about Form and Beauty. Professional artists talk about where to buy cheap turpentine.” ~ Picasso

Turpentine is:

A network of podcasts, newsletters, and more covering tech, business, and culture, from the perspective of industry insiders and experts.

Think The Ringer or Barstool, for tech.

We believe that the world’s most interesting, important, and useful ideas and experiences come from those with skin in the game, sharing their expertise and passion – now matter how niche the topic.

Today, as generative AI is able to simulate all but the most original written content, I think this is more true than ever.

In a world where the marginal cost of creating personalised content goes to 0, it is the interesting ideas locked up in the heads of experts that remain scarce. At Turpentine we’re going to share these valuable ideas with the world.

I’m joining Turpentine to run “special projects”. This means identifying the company’s most pressing open-ended problems, and figuring them out. I’m excited to work with Erik, and I’m looking forward to an open-ended role that will let me meet lots of interesting people and help me learn which things I want to keep doing.

Thank you, Wren!

There’s no way this opportunity would’ve come up without my experience at Wren.

Wren has genuinely been the best job of my life. And the Wren team have been the smartest, kindest, most fun team I have ever worked with. The best team I’ve ever worked with.

So from the bottom of my heart, thank you, Wren.

🙏🙏🙏🙏🙏