*Some details have been changed, for legal reasons and good manners
I always meant to start my own business eventually as I have a poor relationship with authority, but the original plan was to work for a couple of years first. I did try– I interviewed at a company who needed someone to design infinite spatulas and another that openly laughed at my hourly rate– but neither my portfolio nor my character were attractive enough to land a desirable job right out of the gate and I wasn’t prepared to be patient.
In some ways I was extraordinarily lucky. I had strong emotional support from my family and partner and won a couple of student competitions which gave me a little name recognition and financial breathing room. I had also started freelancing while I wrote my graduate thesis at Pratt (an embarrassingly unserious document with hidden Clash lyrics) and discovered that I enjoyed it.
My first freelance job was memorable: it was a tech company headquartered in a storefront on Jane Street that was working on a Bitcoin ATM. The owner was a vast man permanently parked behind a huge array of screens in the back room. When I came by to interview he told me he was a committed libertarian, and with a stroke of inspiration I lied that I was supporting Rand Paul in the 2016 primary. He hired me on the spot. There was a hyperbaric chamber and a trampoline in another back room, and a bulgy Russian fellow in the front room whose job seemed to be banging enormous dumbbells together over his head. I was fascinated by the entire operation, and would show up when summoned, usually late in the evening, and ideate on how best to move cash and receipts around a box with an ever changing cast of sweaty men. The owner would pay me by fishing uncounted handfuls of damp bills out of his sweatpants pockets. Since they were hundreds, I did not object. My more sensible boyfriend would park at a cafe round the corner and worry until I emerged. Predictably, I went over one day to find the windows dark and the door padlocked and never heard from any of them again.
My second freelance project, which I picked up while still nominally looking for a real job, was to design food carts. This was bankrolled by an ex-priest who once showed up to a meeting with his SUV full of bullet holes (he tried to convince me they were from hail). This was a genuine design project, and I loved every minute of it. I met the man who builds and repairs most of New York’s food trucks and carts, a supremely talented Armenian named Ahmed who could take a twisted mass of sheet metal and mold it back into a working cart with his bare hands. I watched shawarma guys, lobster guys and sandwich guys performing feats of precision in their cramped mobile kitchens. We even finished a few carts, though their high aesthetic development wound up largely obscured behind chip bags. Alas, this company also went under unexpectedly, and I heard the ex-priest fled to Aruba with millions in NYC park budget cash, but I must say I don’t believe that.
Around that time, I decided that I should start going after more respectable clients.
I discovered, via now-defunct freelancing platforms, that there are many private individuals who have ideas and no clue how to get them to market. I barely knew more than they, but I had enough hubris to act like I did, and panic certainly sharpens the mind. I learned as much blundering a few small products into existence as I learned in three years of graduate school.
In retrospect, some of these clients must have realized I had no idea what I was doing and took a chance on me anyway. I’ll always be grateful for that. It’s astonishing to me that almost none of them fired me, given how frequently and noticeably I screwed up, and I’m grateful for that too. I started advertising in a small way, and they kept coming. My rates weren’t high, and I took on everything. Foam blocks to strengthen the neck? Rigid 3D printed bras? Cardboard lawn furniture? Bring it on. Some of these things are still in production, but most vanished without a trace.
While these small projects yielded few good stories, they did earn me a living. I moved my operations into a coworking space and myself out of my shared apartment. I stopped eating quite so much instant ramen and adopted a little black cat.
When I had more work than I could handle I started pulling in part time help. Perhaps because the only person I’ve ever successfully intimidated is my little brother, my first few hires were young fellows who superficially resembled him and whom I could order around without feeling ridiculous. As with the early clients, they must have known that I was making things up as I went along but they gave me grace and filled in on CAD work without a peep. Of course I couldn’t yet pay well enough to keep them around indefinitely, but Solidworks is a fairly common skill and at that point Spitfire was less of a business than a freelancer with help. I also brought on a packaging designer who was an LSD enthusiast and liked to tell me all about her sex party circuit. I would later learn that personality fit is important, but at the time I was just glad she was willing to work with me.
In the spring of 2019, after a run of decent sized projects, I took on my first full time employee. She had just finished her master’s at Pratt, and I thank my stars that I convinced her to work for me before anyone else did. Having someone who took Spitfire seriously helped me take it seriously too. The first three years had felt like a lark, and I always had the vague idea that I’d get a real job eventually. That changed when I was solely responsible for someone else’s income in addition to my own. I had to put more effort into finding work to keep us both busy, and raised my rates accordingly.
In February 2020 we moved to a new office. It was a tiny little former pasta shop in Park Slope, with exposed brick and a majestic iron door. I hired an artist friend to paint a razzle dazzle mural on the back wall. It was cramped, but wonderful. Every morning I’d open the huge door with a clang and sit down at my tiny desk, in my tiny chair, surrounded by plants and art and cheerful chaos and feel like a real proprietor. Clients who came by tended to stay until I ejected them, drinking coffee and eating the fancy chocolate I always have on hand.
Of course in March 2020, an office became irrelevant. I still went in every day- I’ve never liked working from home- but it was suddenly an unnecessary expense. We muddled through the blur of the Covid years, as work evaporated and supply chains struggled, sustained on PPP loans, savings and loyal clients. People would ask if I thought it was a good time to launch new products, and I had to say I didn’t know. It’s easy to remember that time as a cozy hiatus, blessedly free of social obligations, but that erases the constant weight of anxiety on everyone’s shoulders. When my parents got their vaccines I sobbed at my desk as a big part of that anxiety melted away.
As Brooklyn came slowly back to life, so did Spitfire. The team came back to the office, now more chaotic than ever, as well as client teams of varying sizes. We crammed everyone in somehow. Once a prototype meditation pod showed up in an enormous crate that I had to break down on the sidewalk, as it would not fit through the door. Another time, during a big overnight storm, the office toilet exploded. All the projects that had gone on hold during the pandemic picked up again, and I had to pull in more help. I hired another full time designer, whose brightly well organized mind is a wonderful counterbalance to my thoroughly disorganized one.
We made lamps that went on Shark Tank, electronics that went to CES, cold plunges that athletes went into. We made pots and pans, baby carriers, pet products, robots and carafes. A shipping container full of products we’d designed rolled off a ship and remains on the bottom of the pacific. Some products were successful and some weren’t. Sometimes I felt competent and sometimes I didn’t, but I tried to maintain an unruffled facade no matter what.
Reasonably high rates and a fancy zip code kept most of the crazier clients at bay– no one paid me in damp, uncounted bills anymore– but they still appeared occasionally. Once or twice I had to actively throw people out when they would not accept that their project was a bad fit. I found that rocketing to my feet, slamming my hands on the table and saying “You need to leave right now because I am going SAILING!” was quite effective, whether I actually was going sailing that day or not.
In the summer of 2024 we had outgrown our tiny office. We had actually outgrown it well before that, but it was such a nice space in such a nice neighborhood I couldn’t bear to let it go. We considered Industry City (too isolated), DUMBO (too bougie) Downtown Brooklyn (too depressing) and Red Hook (too inaccessible). We finally landed in a huge, scruffy red brick studio building in Gowanus with the nicest, most effective staff on the planet. Our new corner space, blazingly sunny with a constant rain of ceiling flakes floating down on us, felt palatial. Somehow the mass of materials, prototypes, samples, electronics and tools that had choked our small office filled the new one right up too. I splurged on nice electronic standing desks for everyone.
In the beginning of 2025 the newly reelected Donald Trump announced sweeping tariffs that affected about eighty percent of our clients. Even companies that did not manufacture overseas were impacted, as grants for green infrastructure and other sustainability-focussed innovation dried up. It suddenly became unaffordable for a private individual to produce anything overseas, at all. Clients pulled out en masse, and I could not blame them. Again, we survived on savings and the remnants of our Covid loans, finding North American vendors where we could, and hoping things would stabilize. I would lie awake all night, rigid with anxiety, before putting a brave face on the next day. My senior designer, understandably, packed up and moved to France. I considered leaving too.
Eventually some tariffs were struck down and some reduced, and I did an expensive but effective advertising blitz to bring in more clients. I have become acutely aware of how beholden creative industries are to world events and I resent that. Covid was one thing, akin to a natural disaster, but to be at the whim of a few corrupt individuals is a lot to bear. More than ever, I try to diversify the industries we work in and the people we work with so that we can maintain some sort of stability no matter what happens.
If there is one thing I’ve learned that helps with rough times, it’s compartmentalization. Even as business struggled and the news made me want to crawl under a rock, life went on and I forced myself to enjoy it. I sailed more than ever, went to every protest, volunteered for the Mamdani campaign, eloped with my long time sweetheart. These things, and the cheerful diligence of my team, provided some bright spots in the absolute dumpster fire that was 2025.
So it’s ten years and two big crises down, and we’re still going. Things could be better, but they could be a lot worse. My office is green with plants and chaotic with prototypes and the sun is warm on my shoulders. I get to work on things I enjoy and meet interesting people. I don’t feel like an imposter all that often anymore. I learned that the more seriously I take myself the more seriously other people take me, which is a mixed blessing. I can’t rant or tantrum or be a goofball all the time, and gravitas does not come naturally to me.
So what will the next ten years look like? Maybe I’ll get bored and go work as a welder or a bike mechanic or get a captain’s license. Or maybe I’ll buy a cabin cruiser and sail away somewhere. Or maybe the weight of living in a country that no longer represents what I believe in will become too much and I’ll start again overseas. Probably not, but it is part of my nature that I must keep the door to something else open just a crack.
Realistically, the next ten years will probably look much the same. Ups and downs, interesting projects, boring projects, clever people I love to be around and others whom I endure. I hope to grow my team a bit, and I hope the extraordinary luck I’ve had in my hires continues.
When I sat down to write this piece I meant to frame it as a humorously self deprecating list of regrets. As I thought back through the years, however, I found I had very few. Not that I haven’t messed up- I could kick myself up and down the stairs all day for the things I should have done differently- but that’s not the same as regrets. And for all the work it’s taken to build and maintain this odd little business, all the worry and excitement and boredom and delight and grey hair and bitten nails and success and stress and laughter, I would do it again in a heartbeat.
Isis Shiffer
