My drawing board is currently covered in a mix of art supplies and aggressively pungent deli meats.
I’ve got a puddle of Higgins ink dangerously close to a towering pastrami on rye, and my entire apartment smells of mustard. Outside my window, a sanitation truck is violently reversing down 9th Avenue. The floorboards are vibrating. On my monitor, looking entirely too relaxed for a man navigating the crazy New York City culinary scene, sits Ben Gollan, a fellow Aussie expat making a go of it in the big smoke.
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Ben’s the undisputed Sandwich Tour King of New York. He runs a wildly successful walking tour company called ‘A Man and His Sandwich’, where he guides people through the absolute best, most artery-clogging delis in the five boroughs. But the thing that always short-circuits my brain about Ben isn’t his encyclopaedic knowledge of cured meats. It’s his backstory.
It’s always deeply comforting to talk to another expat. We spent a significant portion of the hour just being two Australians with thick accents, complaining loudly about the structural inefficiencies of New York City while simultaneously admitting we’d never live anywhere else.
We got into the gritty reality of the New York hustle. If you’re an Aussie expat, you know the exact cultural whiplash we’re talking about. Back home, we have this insidious thing called the tall poppy syndrome. If you try something outside the box, people immediately try to cut you down. Ben mentioned that when he goes back to Australia and tells people he runs sandwich tours, they laugh and ask what his real job is. But here in New York? People look at him and say, “That’s a great idea, I bet you’re the best.”
The city runs on that delusional, infectious encouragement. It’s the only place where a hungover, out-of-work chef from South Africa can stare at leftover Indian paratha bread and some banh mi scraps in his fridge, accidentally invent a pulled-pork paratha taco, and suddenly end up running three wildly lucrative storefronts. (That’s the true story of Goa Taco, by the way. A legendary Lower East Side staple born entirely out of desperation and a hangover).
As I mentioned, Ben’s a fellow expat Australian. Back in Sydney, he was a crisply dressed corporate lawyer working for the government. He traded the courtroom for the chaotic, unforgiving streets of New York back in 2016, all to support his wife’s career. Somewhere along the line, a single pastrami sandwich at a now-defunct East Village deli completely derailed his professional trajectory. He ate the sandwich, had a culinary epiphany, and decided he was going to dedicate his life to the space between two pieces of bread.
There’s something deeply terrifying about abandoning a stable, lucrative law career to yell about sandwiches on a Brooklyn sidewalk. But it’s the kind of unhinged creative pivot I completely admire...
During our Draw Me Anything session, I set myself the absurd task of drawing a photorealistic pastrami sandwich while we talked. I quickly realised that drawing bread’s a nightmare. Bread’s just a chaotic sponge. You try to capture the crust with pilot pen, and it just looks like a diseased rock.
Ben’s got this incredible, magnetic energy. You can see exactly why his tours are perpetually sold out. The live chat was losing its collective mind over his deli recommendations. You could feel the audience getting hungry through the screen…
When Ben’s wife got transferred to the Audible headquarters in New York, Ben followed her with absolutely no plan. He spent his days wandering different neighbourhoods, picking an area based entirely on a sandwich he wanted to try. He started a travel blog read by exactly eight people (mostly his mum and dad). Fast forward a few years, and he’s running sold-out tours five days a week, debating the structural integrity of hot dogs with tourists from all over the world -mainly spending his time in my old stomping ground in the East Village.
Speaking of the East Village, Ben dropped an incredible theory about why the food there is so good. It all comes down to the MTA. There isn’t a subway station directly inside the neighbourhood. Because you have to slog fifteen minutes from the Second Avenue train just to get there, the massive corporate franchises don’t bother moving in. That lack of corporate gentrification creates a protective bubble for mom-and-pop shops to actually innovate. It’s a beautiful, accidental urban defence mechanism.
We swapped war stories about arriving in the city and actively trying to avoid other Australians. We both wanted to be real New Yorkers so badly that we shunned our own community, a decision we both regret now.
You have to figure out how to navigate the city on your own terms. For Ben, it meant weaponising his accent. He told a glorious story about rocking up to Staten Island for his American driving test. He sat in the car, looked at the instructor, and delivered a highly strategic, incredibly thick “G’day mate.” He passed the test in forty-two seconds.
My transition wasn’t quite as smooth. I confessed to Ben that after bombing on stage for the fiftieth time with my old Australian stand-up material, I had a total meltdown. I was sitting in a bathroom stall at the Ludlow Hotel, furious at my own joke book. I threw it in the toilet and flushed it. Naturally, the plumbing backed up, overflowed, and spewed seven years of my absolute worst jokes back onto the wet floor tiles. I had to run out of the lobby like a fugitive. You really can’t write a better metaphor for the creative process than watching your own material literally back up on you in a Lower East Side toilet.
We also got into the deeply contentious debate of whether a hot dog qualifies as a sandwich. Ben casually dropped the historical fact that burgers were originally invented in Germany as the “Hamburg sandwich.” My culinary snobbery didn’t stand a chance.
If you want to watch two expats talk shop about the New York hustle, the philosophy of sandwich bread, and the terrifying reality of career pivots, you need to watch the full replay.
As always, the video of our conversation and my disastrous attempt at live food illustration’s locked behind the paywall. If you haven’t upgraded to a paid subscription yet, please consider doing it today. It costs less than a decent bodega sandwich, it keeps the ink flowing, and it gives you access to the entire archive of Draw Me Anything episodes.
Thank you Nishant Jain, Nimita Kaul, Hue Walker, Catherine Brennan, and many others for tuning in on the day.
‘til next time!
Your pal,
PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.
