Hello! It has been over 2 years (coming up on 3) since my last published article on The Flywheel. Can you believe that? I can’t believe it, so how could you?

I stopped publishing The Flywheel shortly after announcing to you all that my cofounder and I took Swapstack out of On Deck and went for it on our own. Of course, that is no coincidence. Things got busy, stayed busy, and only recently became less busy.

I am now on the other side of my Swapstack story, and I wanted to share my journey with you all for two reasons: (1) I would bet some of you are navigating similar challenges, so I am hoping this might help; and (2) I want to put some asks out into the universe.

Swapstack Goes Off (Deck) Jake Singer · October 21, 2021 Read full story

Since that article, here’s a (very) short list of what we accomplished with Swapstack:

• We raised $650K in a pre-seed round from angel investors, friends, and family

• We hired a team of 6 (at peak team size) and grew to $25,000 monthly revenue, navigating an enormous global shift in advertising spending along the way

• We decided not to raise again, and instead sold the company to beehiiv in late 2023

• My cofounder Jake Schonberger and his team moved over and are thriving. My team and I transitioned certain pieces to beehiiv and then parted ways

When put in a bullet form list, it almost seems like it was quick and easy! But in all honesty it was at once exhilarating and exhausting..a true rich life experience.

This Email

Why am I sending this email, now of all times? I’ve been (mostly) off Swapstack since the beginning of this year, and I have not yet prioritized writing more Flywheel articles. If I’m honest, I don’t know if I ever will.

But at some point I realized that this newsletter attracted an unbelievable collection of people who, at one point, placed at least some value on my thoughts and writing. And with this being a transitional moment in my career (more on that below), I figured when would be a better time to tap into this incredible network for advice, camaraderie, and support?

I also have spoken to other folks navigating the end of their startup journey, and realize that it’s a difficult moment for many of us. I am hopeful that this story encourages any of you who need it.

Inspired by my friend Sid Jha, I’ve therefore decided to repurpose (temporarily for now) The Flywheel to send a personal update on what I’ve been up to, and what I’m hoping to do next. I’ll end with a couple of asks and parting thoughts, and hope you don’t mind my personal indulgences.

2024 in a nutshell

Jake Cooks

This year has been strange for me. After wrapping up work on Swapstack, I was feeling pretty burned out. I had been glued to a laptop for the better part of 8 years (between Amazon and Swapstack), and needed a break.

People who know me personally know I’ve gotten very into cooking in recent years, and I married this passion with a need to be offline by applying for and landing a job at an upscale restaurant in my DC neighborhood. This was by no means a conventional thing to do, and I could not have cared less.

I worked there for just a bit over two months—it was always going to be a temporary experience—but it achieved precisely what I needed it to: a break from the computer, an immersion into a new world with new types of people, and an opportunity to not think for a while. I also achieved a “viral” Google Maps contribution with a picture of some garlic knots I made (legitimately the most delicious garlic knots you’ll ever have, by the way).

Mini Retirement

After cooking for two months, I decided to take some actual unstructured time off. “Unstructured Time Off” now holds two different places on my LinkedIn profile. Not sure what this says about me and my career choices.

The arc of my mini retirement was U-shaped. It started so well. I got into baking sourdough at home, I launched a nascent Youtube and Gumroad project following my passion for productivity apps, I worked out every day, I spent a lot of time in the mountains, and I did some freelance work. I loved it.

And at some point, I stopped loving it. I started thinking about what I might do next “for real”, and it started to stress me out. As a founder, one fills basically any role available. At Swapstack, I was the CTO, CPO, and CFO. That’s a lot of things at once, and it turns out that’s kind of right for me. But I knew that being a founder again straight away wasn’t going to work, and so the prospect of finding a ‘real job’ loomed. And nothing felt like the right fit. From my couch at home, I kept ruling things out, and I was blocking myself from moving forward.

This process lasted for a solid month or two. I won’t call it a depression, but it wasn’t too far off from one. From speaking to other former founders, I have come to learn that this isn’t a wholly unique experience: there is a malaise period that hits you at some point after a startup, when you start to seriously doubt yourself and your options.

Thankfully this didn’t last forever. I’m an energetic person, so I probably was always going to have an upper limit on how long I could mope around, but I think there was a key turning point for me: I re-read Cal Newport’s So Good They Can’t Ignore You and it shifted my mindset from worrying about what I wanted to do to what I was good at and how I could add value to someone. That simple shift spurred me into action once again.

Job Searching

Through this process, I landed on “telling stories about and with data” as my superpower skill that I want to continue investing in during the next phase of my career. And to readers of the Flywheel it should come as no real surprise; after all, that was basically the premise of this newsletter.¹

This is a skill that can manifest in many types of roles, so I am trying to be open minded. For now, I’m exploring opportunities in three buckets:

• I’m exploring the possibility of becoming a “Data Scientist” at bigger tech companies. This would be a bit of a career pivot, but I think it would be absolutely awesome to learn how real Data Scientists do it in world class organizations. I have some interviews lined up (think places like DoorDash), and am working hard to be ready for those.

• I am also talking to a variety of large companies about data-heavy product management roles. This is closer to my roots (and resume), and that means I am targeting more senior roles for this functional idea.

• Finally, I am exploring the possibility of joining slightly bigger startups (think Series A) in a variety of roles as well. Anywhere from product to finance to ops to data, I think I can be useful, and while I think it’s a little tough to triangulate on the right role, level etc, I think this bucket is the most exciting for me because I love startups and I am probably more a startup person than anything else.

How you can help

Thank you for reading this far! I wanted to share this and put out into the world what I’m working on because good things have come to me when I’ve done that in the past.

Specifically, though, if you’re motivated to help, I’d love to ask for the following:

1. If you either work at, lead, or know someone at a company that fits into one of the three buckets above, and you think they might want to talk to someone like me, please let me know!

2. If you think my thinking is awful and you have some better ideas for me, please let me know!

3. If you are a fun and interesting person and you want to meet me for any reason, I’m a big believer in having agenda-less conversations with new people (back to the serendipity idea), so please let me know!

4. If you would like me to send personal updates like this again in the future (maybe 1 or 2 times per year), please let me know!

5. If you think I could be helpful to you in some way, please let me know!

I guess…just let me know!

OK, that’s it! Thanks again for reading, and actually..for everything.