Jake Singer is cofounder of Swapstack, the new marketplace connecting newsletter publishers and brands for advertising opportunities. Swapstack has been covered by Adweek and Business Insider among other publications and is sweeping up the newsletter ecosystem.
Here, Jake speaks about his experience writing The Flywheel, the newsletter that inspired Swapstack into being.
Jake's experience with newsletters
How did you get started writing?
I have always enjoyed writing! For whatever reason, and despite never really considering myself a writer, I have always taken great pride in writing well whenever the opportunity arose (schoolwork, professional settings, or even just emails to people).
My first true writing experience was as a contributor to one of the more popular Liverpool FC blogs out there, The Liverpool Offside in 2013 or so, and I did that during business school (so for 2 years).
A more seminal writing experience was when I started working at Amazon in 2015. Amazon has a super unique, heavy writing culture, and it was an incredible learning opportunity for me. It allowed me to sharpen what I suppose was a raw writing style, into one that was more professional and concise. Now, one of the aspects of writing I most enjoy is being able to go back and forth between more ‘creative’ modes and the more succinct one I learned at Amazon.
What was the first version of the newsletter like?
The first edition of The Flywheel went just about 11 months ago! It was an article about Peloton and its flywheel.
To be honest, I didn’t set out to create a popular newsletter—I was on my way out of Amazon, and knew I needed to experiment with multiple projects to find what I wanted to do next. Writing was just one of my ideas for such a project. I was so noncommittal about this as a legitimate project, that I didn’t even ask my friends/family to subscribe! The first email went out to 6 people (and I scored a rare 100% open rate!)
The idea to write about Peloton’s flywheel occurred to me because the concept is heavily utilized at Amazon, and as a new Peloton user my mind was full of ideas for how they could improve their offering.
I realized pretty quickly that I could create an entire theme around flywheels, and so The Flywheel was born!
How is it different today? How many subscribers do you have now?
The first 6-7 articles were almost all about public companies. Once it grew to a certain size, I started using the momentum to line up interviews with startup founders, which is what some of the more recent pieces have featured.
The Flywheel is approaching 4,000 subscribers! The growth curve has been really interesting. It was super sharp at the beginning, and then I lost steam. We’ll surely talk about that soon!
The newsletter business
What strategies have you used to grow your subscriber list?
I have explicitly decided not to pursue a lot of growth strategies. Every time I’ve attempted anything in the name of growth, it has fallen pretty flat. Conversely, all of the biggest growth days for The Flywheel were the result of someone with big Twitter followings discovering it and sharing it based on the quality of the content.
My main takeaway from this is that it’s a lot better to focus on producing good stuff consistently, than any particular growth tactics. That may change as my following increases, but in the early days that’s how I approached it and—although I am quick to recognize the role of luck—I stand by it.
To the extent that this is a tactic, I post each new article on Twitter and LinkedIn, and pray that someone big will retweet!
How do you think about monetizing your newsletter?
I haven’t really done much here yet. The journey has been interesting: I decided early on that I wanted to go the ads route (over subscriptions). When I topped 2,000 readers I started looking around for potential sponsors, and found them surprisingly difficult to find.
This led me to the early idea for what eventually became my current startup Swapstack. I realized that if I struggled to find sponsors, it’s likely that many others were in a similar position. After talking to tons of other writers and teaming up with my cofounder Jake Schonberger (who writes an awesome newsletter called The Premoney List, focused on early stage startups who are raising pre-seed and seed rounds), we decided there was enough here to go for it.
It’s been a fantastic experience; the only downside is it’s reduced my available time for The Flywheel quite a bit. Given my inability to produce consistently over the past few months, I’ve decided to lower monetization down on the priority list for the time being.
When it’s time to pick it up again, I plan to heavily use Swapstack to find sponsors!
Have you considered other monetization strategies? A subscription tier, e-commerce, adding a paid community, etc?
The only other idea I have gotten excited about is to build a shared knowledge graph about the companies that I’m researching through the course of my writing. I use Roam Research for research, outlining, and drafting, and thought that I could potentially turn what I’m already doing there into a product that would be useful for others. I haven’t gotten too far with this yet!
Jake's writing process
How do you decide what to write about? How do you edit yourself?
I wouldn’t say I have a clear process for this. Early on I was choosing public companies about whom I felt I could add something interesting to the discussion. This was a mix of companies I knew from personal experience (Peloton, Stitch Fix) and others that I thought the dominant narrative wasn’t really correct (Zillow, DoorDash). Now, it’s more driven by which interviews I have lined up.
I’m still deciding if I want to focus more on the public company analysis angle or the startup interview angle. If any Newsletter Crew readers have an opinion, I’m all ears!
How do you build trust with your audience?
To be honest it’s not something that has crossed my mind. For now, my main focus is on finding the right topics, cadence, and style that brings me the most joy. Of course I want my readers to love every piece, but I know that if I don’t love writing The Flywheel it won’t be sustainable. So, hopefully readers get that, and I think they do.
I won’t feel super comfortable turning on the monetization spigot until I feel more confident that I’ve nailed this aspect and can commit to writing it for years to come. Once I do, then I’ll have to come up with a more intentional plan to maintain trust.
What strategies have you learned about creating clear, concise writing week after week?
I’ll let you know when I get there! :)
What is the best writing advice you've ever been given?
“Perfect is the enemy of good”. This isn’t just writing advice, but it’s phenomenal writing advice.