Swapstack

Jake Singer and Jake Schonberger came together during an On Deck hackathon. They both had experience running their own individual newsletters and were curious about the space as a whole, specifically how they could help both writers and sponsors reach each other in powerful and efficient ways. “We built Swapstack to scratch our own itch,” their website reads. “Our goal is to serve as every creator’s sales team, so they can spend time doing what they love.” ‍

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How and when did you two first meet?

Jake Schonberger: Towards the end of my ODF4 program, I had just started working on my newsletter: The Premoney List. I was extremely interested in newsletters, and decided to partake in an On Deck hackathon. During the hackathon, I built a chrome extension with a few other On Deck fellows which focused on helping newsletter writers grow their audiences through cross-promotions. As part of the hackathon, I was introduced to Jake Singer (ODF5), who had also recently started his own newsletter The Flywheel. We kept talking, and ultimately began building a new version of Swapstack that focused on newsletter monetization.

Jake Singer: That was 2 years ago. We spent about 6 months building Swapstack together before actually meeting in person. 

What was your first impression of one another?

Jake Schonberger: Very good! The introduction to one another felt really serendipitous in its own right. I had just finished grad school, Singer had just quit his job at Amazon. We had both recently started our own newsletters, both recently joined On Deck AND both were interested in the newsletter space. So a lot of the biggest ‘initial co-founder questions’ of timing and interest alignment were already answered. That was really intriguing. 

Jake Singer: My first impression was a good one! He had a ton of cool ideas about opportunities to build for creators, and we had really energetic conversations.

How did you know your co-founder was “the one”? ‍

Jake Schonberger We worked together for a couple of months before we committed to each other and to Swapstack. For a while, we were both interviewing elsewhere, exploring other opportunities, all the while being extremely transparent with one another about those pursuits. Ultimately, our excitement around Swapstack kept growing and we decided to double down. 

Jake Singer: We took it pretty slowly and deliberately. Once we converged on an idea we wanted to explore together, we still wanted to make sure that we were compatible as people and colleagues. We found a ‘founder fit’ questionnaire — First Round Review’s “Co-founder questionnaire”— and spent a solid 2-3 weeks working through it.

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Was having a co-founder what you expected?

Jake Schonberger: My expectation was that a co-founder meant a partner, someone who is 100% aligned on vision and goals around value creation. This doesn’t mean our styles or processes need to be perfectly aligned or complementary. We get along and work very well together. Much of that relationship success came down to putting in the hours to understand each other and figure out the best ways to work together.

Jake Singer: My expectations were really high: I wanted both a practical partner and an emotional one. On the practical side, I wanted someone who had skillsets and interests that complemented my own. On the emotional side, I wanted someone who would be able to stay calm and patient through ups and downs, as well as be fun to work with. I think all in all, it has been pretty much what I expected!‍

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What’s a strength of your co-founder that you didn’t know you were looking for?

Jake Schonberger: A knack for process building. I’ve always known that I’m not a process-builder, but now having worked with someone who loves a good process, and is good at creating them, it’s a skill set that I’ll never look the other way on ever again. 

Jake Singer: His desire and ability to sell! I didn’t realize how little I wanted to do that until we started doing it, but he loves it. It really is amazing to be able to focus on building while you have someone else out there selling.

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Do you have any advice for founders looking for co-founders?

Jake Schonberger: There are two really important lessons that I learned from finding a co-founder and working with others in the past that didn’t work out as expected: 

Number one: you need the desire and the ability to build. I think part of the reason Jake and I ended up working together was that we were both actively working on similar projects on our own prior to meeting each other.

I would not have been comfortable kicking off a co-founder relationship with someone who wasn’t already actively working on something, or who hasn't proven their ability to start something from scratch.  - Jake Schonberger
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Number two: you need alignment on goal, not skills. It ended up working out great that Singer had a more technical side, but the most important part of the co-founder relationship was alignment on goals. Unless you are building a deep-tech startup, having a co-founder who is dedicated to solving the same problem and intensely curious is the most important thing. You can always find technical help when you need it.

Connect with Jake Singer and Jake Schonberger, and check out Swapstack