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Funding Cushion

A few years ago, a friend of mine at FiftyThree reached out to see if I was available for a freelance gig. A few weeks later, we launched my first scroll-based animation website, for FiftyThree’s Pencil. Shortly after, my friend reached out again to see if I’d be open to an intro. FiftyThree’s earliest investor, Shana Fisher of Third Kind Venture Capital, saw the website and wanted to meet.

I’ve always had a pessimistic view of VCs and apps that take investment. In my eyes, taking investment meant looking for an early exit rather than building a sustainable product. (I’ve read enough Our Incredible Journey posts to become cynical.) My dream has always been to build an app that could fully support me—I would work on it for the rest of my career and have complete control of it. At the time, I didn’t have an app—I was only a freelancer—so, interest from an investor made me curious.

I took the meeting.

We talked about my work, my background, and my aspirations. We also talked about Shana’s role as an investor, her companies, and her views. Shana didn’t fit the negative image I had of VCs. Her transparency to my questions was refreshing, and I appreciated her straightforward way of speaking. Even though I didn’t have an app, or even an idea, Shana was interested in investing in me. I appreciated the gesture, but I wasn’t looking to take investment anytime soon.

Over the next two years, Shana and I continued to meet for coffee every few months. During this time, I burned out from freelancing and came up with the idea for Cushion. I took a few months off to bootstrap Cushion, re-investing the income from my freelance work. And, I officially launched Cushion the following year.

Cushion started growing, and as it grew, my vision for its future became clearer and more focused. I knew exactly where I wanted to take Cushion, but I also knew that continuing to work alone would only hold me back. I’ve always been reluctant to let others work on Cushion because it’s precious to me, and I thought I worked better alone. After years of working alone, however, my views changed. As Cushion grew, I grew, too. The timing was right to consider hiring.

Financially, I was in no position to hire anyone full-time, so I decided to hire several freelancer friends of mine instead—still using my own income from freelancing. After only a month, we were able to launch three major features and publish an entirely new interview series. I couldn’t believe how much we were able to accomplish at such a high quality and in such a short period of time. Hiring help was the best thing to ever happen to Cushion, but there was a problem—I knew I couldn’t afford to pay everyone for long, let alone pay myself.

I considered freelancing more, but then I’d be working on Cushion less. Taking investment was a clear solution, but I shot it down each time. I assumed that taking investment meant losing control of Cushion. I imagined being forced to sell by a board of shadowy figures. I thought everyone would be so disappointed in me. I was scarred from witnessing so many startups force an exit as a last-ditch effort or run out of money and spiral out of control. I never wanted to see that happen to Cushion.

I reached out to a friend of mine who has been through the startup world. I’ve always looked up to him as one of the smartest and most genuine people I know. Instead of simply giving me advice, he pulled out a notepad and spent over an hour in a coffee shop running through every angle of my situation. He eased my extreme views of taking investment and sketched out a path I could take based on what I wanted to do with Cushion. I could partner with Shana to fund Cushion, but maintain my goal of building Cushion into a real business, instead of a rocketship startup.

After speaking with my friend, I followed up with Shana. I wanted a better understanding of what taking investment would look like, instead of simply shutting down the idea completely. I met with Shana and her partner, Alex Binkley, at their office in Manhattan. I came prepared with a list of things that were important to me, if I were to take investment.

  • I only wanted to raise one round of funding, so Cushion could reach profitability without the expectation to raise more money.

  • I would stretch the investment, so we’d have a comfortable runway without feeling rushed.

  • I could continue Cushion’s transparency with the journal and running costs.

  • And, if we weren’t profitable by the time we ran out of funding, we could return to bootstrapping.

“Done”, Shana said.

We ended the meeting with every question answered and every doubt diminished—I felt a great sense of reassurance. After the coffee with my friend, I was leaning toward investment, but Shana and Alex’s openness and accommodation put me over the top.

When I started Cushion, if someone were to tell me I would one day take investment, I wouldn’t have believed them. I also wouldn’t have believed that I would hire a team. Over the past two years, however, Cushion has grown from an idea into something real, and I’ve grown with it. Considering where Cushion is now and where I want it to go, I know this is the right decision, and most importantly, with the right people.

So, what’s next? The most exciting news is that Larry Fox, responsible for Cushion’s recent smart features, is joining Cushion full-time. We’ll continue to work out of our co-working space in Brooklyn and continue hiring freelancers to collaborate with. And, for the first time in almost five years, I’ll finally have a consistent income.

I can’t wait for Cushion’s future. Stay tuned!