An Interview with Tayler Carraway, Happy Medium
On being your own muse + the beginnings (and future) of Happy Medium
A Note From The Editor
Does great art beget great business, or vice versa?
The causal relationship may not be clear, but personally, I choose to believe it goes both ways. Happy Medium is a prime example of when both work together, and you don’t really know which side benefits the other more.
An art café slash pottery studio slash figure drawing class slash fill in the blank — what’s at their core?
For the uninitiated, the TikTok-beloved space opened in Two Bridges (near Chinatown) over three years ago. What started as a small gathering of friends opting for nights in has grown into a community and experience with two locations.
One could argue that the space and its supporters have brought creative gatherings and ‘artist dates’ into the mainstream. Bold claim, but truthfully not without merit.
I’ve had the pleasure of knowing Tayler since even before this arc in her life. We met online during the pandemic when she joined a room I was hosting on Clubhouse.
Recently, we caught up about Happy Medium, and what I anticipated would be a typical conversation about business challenges turned into something far more nuanced. We explored how leaning into discomfort can actually fuel creativity, and how hospitality isn't just about service—it's about creating the conditions for people to discover their creative voice. Most fascinating was her perspective on the supposed tension between art and commerce. Rather than seeing them as opposing forces, Tayler has found ways to make them thrive together, each supporting and strengthening the other.
Her background reads like a classic New York story: economics degree, a stint in fashion buying, all the makings of a traditional corporate path. But what she's built with Happy Medium is anything but traditional.
Take their approach to customer service. While most businesses race to automate everything, Happy Medium still handles bookings through Instagram DMs. On paper, it's inefficient. In reality, it's created something rare in today's digital world: genuine human connection before someone even walks through their door.
Throughout our conversation, Tayler talked about business the way others might discuss crafting a piece of art. Each decision feels intentional, from how they structure their pottery workshops to the way they train their staff. It's not about making things easier or more efficient—it's about making them more meaningful.
What became clear is that she's not trying to find some elusive balance between business and creativity. Instead, she's showing how these two worlds can actually make each other better. The business skills give structure to creative vision; the creative approach makes business more human.
And now for the interview…
LA: Let's start with your backstory before Happy Medium. What did that journey look like?
TC: The most common question we get is "What art school did you go to?" The funny thing is, I didn't go to art school and have no classical art training. I was actually an econ major, like my husband Rhett. That's how we met. After college, he went into banking and startups while I went into fashion buying.
I worked with brands like J.Crew, Ralph Lauren, and Victoria's Secret. They were all very brand-driven companies, which definitely influenced us. I was in e-commerce during its early days around 2014 – it was like the Wild West then. Despite my career trajectory, Rhett and I woke up one day around age 28 and realized we were just... unhappy. Nothing was technically wrong, but we weren't satisfied. I knew being a buyer wasn't my end goal.
Creativity is something you can never really replicate – it's about bringing that creativity to life through a brand funnel.
We decided to keep our jobs but work on something together. Our first venture was actually a real estate startup born from our frustrations with renting in New York. It was a very dry business – we were trying to sell tenant experience tools to landlords who didn't care about their tenants. The big lesson? You have to enjoy working with your customers.
After that didn't work out, we organically returned to our creative roots. Rhett's family had always built furniture, and I grew up doing crafts with my mom. He got back into furniture building, I started watercoloring. We completely redesigned our lives around creativity – sold our living room furniture and turned the space into an art studio.
Our friends would come over, initially confused, but then they'd join in. We'd provide supplies and teach them basics. The evening would transform from what would have been pregaming and going out into this meaningful creative connection. We were onto something.
Then we noticed a gap: art supplies weren't inspiring. They were either expensive professional-grade materials or cheap plastic stuff. We wanted something in between – beautiful pastels you could leave on your coffee table, materials you'd actually want to use rather than store away.
That's how Happy Medium started in 2019, focusing on creative goods for good people. I used my e-commerce background to build a supply chain for better art supplies. But what really worked were the in-person events. By 2020, we went all in – quit our jobs, and liquidated our 401Ks. Then of course, 2020 hit, which wasn't ideal for starting an in-person community business. But we survived.
By 2021, people were rediscovering their creative sides. Our vision accelerated – people wanted meaningful offline experiences that didn't revolve around eating, drinking, or spending lots of money. They wanted creativity.
LA: I saw you recently partnered with Glossier.
TC: Yes! That was huge – they've always been on my dream brand list. It was a true partnership, not just them renting our space. We created a custom ceramic piece shaped like their fragrance bottle for customers to paint. About 700 people came through. It was amazing to start with such a perfect brand alignment.
LA: I'm curious about your vision going forward, especially given the rise of art-direction-driven brands and consumers wanting that. You mentioned "art supplies for the casual artist" – can you expand on that?
TC: "Casual artists" is what we call our customers. It's meant to be unserious but meaningful – no pressure. Starting a brand is epically difficult, and I have tremendous respect for anyone who tries. With VC funding drying up in this space, brands starting now really have to come from the heart.
What you're really doing is crafting a narrative for customers to see themselves in. At Ralph Lauren, it was like working on a movie set – they'd spend so much on brand elements that would be immediately cut in a VC environment. But we believe it's worth investing in brand experiences, even if they're not the most efficient choice.
About a year in, it dawned on us: we're a hospitality company.
For example, we still take reservations via DMs. It might drive my team crazy sometimes, but it's a deliberate brand decision. Even when we have a fully integrated system, we'll keep it because it makes our brand feel human. Yes, it costs more to have a customer experience team working around the clock, but how do you quantify the value of someone walking in already feeling comfortable and welcomed?
We've put everything into this brand – our life savings, blood, sweat, and tears. You can tell which founders are doing it just to be founders or make money. The brands that will succeed are the ones with a specific point of view on art direction and are willing to invest in it. Creativity is something you can never really replicate – it's about bringing that creativity to life through a brand funnel.
LA: Let's talk about how Happy Medium evolved into a hospitality company. You mentioned the personal touch starts right from the Instagram DMs and carries through every interaction. Can you walk me through this evolution, from when you first opened the Art Cafe to how you developed your approach to customer experience?
TC: We've been here for three and a half years now. The first year, Rhett and I ran it ourselves while I was still working at Hill House. I couldn't have done this without them – they were incredibly supportive. We weren't VC-backed, so I had to keep working. That's why we were only open nights and weekends at first.
We started with one event a week plus Art Cafe on weekends. By year's end, we were doing four figure drawings weekly plus weekend sessions. Growing the team has been the most challenging part. Unlike a restaurant where you know you need a chef, dishwasher, and servers, we had to invent our roles and structure.
We use Airbnb's "11-star review" exercise as inspiration – imagining the perfect experience and working backward from there.
About a year in, it dawned on us: we're a hospitality company. We started researching how hospitality companies operate, how to communicate our values, and how to set expectations that everyone's primary role here is hospitality. Yes, we operate like a restaurant, but the heart and soul is hospitality because we're asking people to make art with us.
It's like karaoke – some people are totally confident, while others are terrified. We get that full spectrum of emotion, and our team needs to understand, read, and respond to that, ultimately converting everyone to loving the experience. That's how we grow – we still don't pay for marketing. It's all organic, all word of mouth.
Your team has to care deeply. When we're hiring, we make it clear: our primary goal is our customers. Everything else – operations, logistics – could be on fire, but as long as you're ensuring customers have an incredible time, you're doing your job. We'll spend whatever we need to make that happen.
I think we have it a bit easier because customers are physically here, doing something tangible. Our team becomes their built-in friends, and they're immediately connected to so many people.
LA: It's like you're micro-dosing joy at every touchpoint, leading up to the “hero dose” of creation. How did you learn to design these experiences and train others to deliver them?
TC: Rhett and I both worked in restaurants during high school and college, where hospitality directly affected your tips. We're both actually introverts, but we've learned to be conduits for energy in this space. Whatever you're channeling, that's what others pick up on.
We were good at it naturally because we had to be – this was our everything, with no Plan B. When we started hiring, we had to get specific about the elements beyond aesthetics, music, and lighting (which Rhett oversees). It's about building an environment we'd want to be in.
For customer interactions, we keep things like DMs even though we could automate them. Another example is when taking orders, our team kneels down or sits in chairs at table edges to be at eye level with customers. It makes you feel more like a friend than a server.
We always talk to customers about their art – it's something Rhett and I did instinctively and now encourage our team to do. It's amazing when someone comes in saying they can't draw a stick figure, and then creates something incredible. That connection is unique to us – it's different from commenting on someone's meal at a restaurant.
Sometimes these interactions reveal unexpected depths. I remember a woman who drew a beautiful lamb, and when I asked about her inspiration, it turned out to be a memorial for a lamb she'd cared for in agriculture school. People want to be asked about their creations – it boosts their confidence.
We also deliberately structure our offerings differently. In pottery, for instance, we offer unlimited clay, unlike other studios that limit you to a pound.
We use Airbnb's "11-star review" exercise as inspiration – imagining the perfect experience and working backward from there.
During busy seasons, we're processing 1,000 pots weekly. That's multiple full-time jobs just handling the logistics, but we've invested in the team and infrastructure to support that level of customer experience. These micro-doses of joy add up. The devil's in the details.
We're always learning and improving. For our new lamp-building class, we're thinking about how to make wiring a lamp approachable for beginners. We provide guardrails through curated choices – a few lamp bases and shade options. Sometimes removing choice is a courtesy, reducing decision fatigue while ensuring everything aligns with our design philosophy.
LA: The 11-star review framework reminds me of Will Guidara's "Unreasonable Hospitality," which they reference in season two of The Bear. You know that scene where Cousin Richie is at the Michelin star restaurant? He learns that "every day here is like the Super Bowl" – it's the highlight of people's year. Then there's that beautiful moment when they overhear guests wanting Chicago deep-dish and make it happen. What moments of unreasonable hospitality stand out to you, either giving or receiving?
TC: I love that question. It's funny – I could tell you more case studies I've read than experiences I've had.
But here's a meaningful one, though it's kind of tragic. We had to put down our dog earlier this year – he lived to almost 15. When we canceled his Chewy subscription, they sent us a gift. Their team, and even his insurance company, proactively reached out. Finding your customer in a vulnerable moment like that and showing up for them – it shifts your perspective. It was a small gesture, but when I was so sad, it felt incredibly impactful.
At Happy Medium, we try to create these moments too. We teach our team to "always be listening." Like the deep dish pizza example – you have to know what your customers are talking about. Yes, it's eavesdropping, but in a positive way, to facilitate incredible experiences. We call it "surprise and delight."
Sometimes it's as simple as overhearing someone talk about an artist they're inspired by, and our team will dig through our library to find a relevant book. Or if someone's looking for specific collage materials, we'll remember we have that perfect botanical book buried in our pile. It's about going above and beyond whenever possible.
These moments are hard to quantify, but they're where you make your most loyal fans. In our analytical world, it's difficult to attribute this kind of impact, but that's where the magic happens.
LA: It reminds me of Paul Graham's post about "doing things that don't scale."
TC: Yes, exactly!
LA: It's about creating systems that enable these moments of joy, but you have to start with the intention. You might not have direct attribution, but the impact is undeniable. Speaking of creative pursuits, have you read "The War of Art" by Steven Pressfield?
TC: It's been a long time, but yes.
LA: In "The War of Art," Pressfield talks about "turning pro" – that moment when an artist decides to take their work as seriously as a job. I'd love to hear about your and Rhett's "turning pro" moment. When did you realize "we should actually do this"? What was your psychology around that decision, especially given all the resistance Pressfield talks about – the logical doubts about time investment, giving up nights and weekends, and signing a lease? What got you over that hump?
TC: It's a huge hump. I always say to myself, "leap and the net will appear." In the summer of 2019, we started formalizing what we loved. There's that tech advice about making something one person loves, then a hundred, then a thousand. You're not as unique as you think – if you like something, others probably will too. It's about finding your tribe.
We tested the concept first, hosting prototypes of the Art Cafe in our apartment-turned-studio. We didn't tell our friends they were being tested, but we watched: Were they having fun? Were they eager to leave? Instead, they stayed for hours. Friends of friends started asking to come. We realized it wasn't just us and our ten Brooklyn friends who found this cool.
Then came the "now or never" moment. We were 28, had some savings, and I had confidence we could get jobs if needed. I picked October 4th, 2019, to quit – partly because September had five paydays. When you make that decision, you commit. I didn't love my current job anyway, and if I needed another in a few months, fine.
We survived 2020, picking up consulting gigs. Everyone was doing art during lockdown, which validated our concept. The next big commitment was signing our lease in 2021. We made it a three-month pop-up to feel less scary. You tend to catastrophize decisions, but we've never made one that would totally kill us. My advice? Try to make revenue before quitting your day job – totally opposite of what I did, but still.
I've developed such a thick skin and tolerance for discomfort. Even now, I get what I call "vulnerability hangovers." Recently, a TikTok about hiring got too many views and freaked me out. But you have to maintain perspective – if Happy Medium disappeared tomorrow, yes, people would be sad, but life would go on.
You need almost delusional confidence that you can figure things out. We sacrificed everything – nights, weekends, vacations, savings. We didn't pay ourselves for three years, then paid ourselves just enough for rent. Most people aren't willing to make that commitment or suffer through the discomfort of being an adult doing something completely new, failing repeatedly.
The next big moment was hiring our first full-time employees with salaries and benefits – before I even paid myself. Then opening our Greenpoint location, doubling our overhead and expectations. Now we're looking at a production facility. The pressure never really goes away, whether it's VC funding or going public. You just learn to live in that zone of entrepreneurial danger.
It's psychologically tough, which is why founders often burn out or feel isolated. You can't always share these feelings because your team and customers are looking to you. But if you can push through that, and if you're making something cool that you truly love, you're good.
LA: It's like you've built this support mechanism for people taking their own mini creative leaps. Speaking of future leaps, what's your vision beyond the production space?
TC: We're constantly thinking about it. Being bootstrapped means walking a fine line between what we want to do, what we can afford, and what's working best. We look at Disney as inspiration – how they've created experiences across media and in-person touchpoints, how they live in people's hearts and homes.
The production facility would let us explore custom furniture design, create our own ceramics (like we did with Glossier), and expand our product line. We're seeing huge demand on TikTok for expansion to Chicago, LA, Austin, or Dallas. Berlin would be amazing too.
Our dream is to create a casual artist retreat – a hotel experience centered around creativity and making things. We can't be everywhere physically, but we can create kits for people to experience Happy Medium at home: build-a-chair kits, pottery painting kits, etc. We want to reach people everywhere, even if they're not in New York.