How This New Yorker Quit Her Job to Launch a Full-Time Book Club
+ the perfect summer read, the pants I'm living in, and pastels on the go
Cappuccino Thoughts is a weekly newsletter about culture and creativity in New York.
The Corporate Creative Class: Liz Montesano Quit Her Job to Build a Book Club Empire
The Corporate Creative Class series highlights New Yorkers working full-time jobs while making time for creativity on the side. We’ve previously profiled a focaccia maker, a painter, and a preservationist. Today, we’re spotlighting Liz Montesano from Open Book Club NYC, who went all in on her creative pursuits and has built an in-person book club series from the ground up.
She started with a TikTok post and a $5 Venmo ask—and 150 people showed up
CA: Where did you get the idea to start a book club?
LM: "I was part of a book club with friends, but it was hard to manage because there wasn’t really someone in charge of it.” In an attempt to open it up, she posted on TikTok saying she was hosting a book club and anyone was welcome. “Over 150 people tried to sign up for the first one, and I realized I was onto something.” She asked attendees to Venmo $5 to cover wine, and started with simple, accessible reading—essays from The New Yorker or The Atlantic. “Something they could even read on the subway ride over.”
"You can actually sustain a good conversation even around a piece that short. I had to get people into the habit of reading and then earn people’s trust. I was just a random person online at first, but now people trust my taste and they will read a whole book. And, of course, we start talking about the essay or book, but ultimately, people are there to meet each other, and the conversation would become about more than just the reading.
CA: How do you think about the challenges of building a community?
LM: "The thing about community building is it’s not technically hard. You don’t have to learn a new coding language. But there’s a lot of soft skills, and it doesn’t work for everyone.”
That’s why, she believes, brand-led community efforts often fall flat. “The goal is not actually to build a community, it’s to sell you perfume.”
What she brings instead is intentional facilitation. “I know how to ask the right questions to make people comfortable and start to engage.” She also emphasizes the importance of having a shared foundation. “Something I see where it doesn’t work is when people just plan things for something like ‘women in their 20s in New York’. That’s better than nothing, but you need something to bond over. It doesn’t need to be that deep. But at least a book gives you a starting point. It’s not like Soho House, where the connecting piece is just wanting to be cool.”
CA: It sounds like what you’re really offering is community, and books are the way to get there. I saw
write the other day that more community events should be monetized, but I don’t totally agree. At the same time, you’re providing a lot of value to your community. How do you think about monetizing this work?LM: “I do think that I’m creating something of value and I’m asking people to help make that my job. People are so okay with corporations ripping them off, but then, because there’s a face, people feel okay arguing about the price. Like, what are you talking about? Jeff Bezos is renting out VENICE.”
Still, she balances accessibility and sustainability. “I try to mix in some free events every month, but it's harder to gauge who will show up and how genuinely they'll engage. There’s a higher quality of engagement when the stakes are raised a little.” She also offers options for readers who may not be able to afford the book. “I am able to get copies of the books from publishers sometimes, and you can select on the form if you can’t afford the book and I can usually get you a copy.”
CA: Where do you think about taking Open Book Club from here?
LM: “I don’t know that community can really be scaled,” she says. “I’d love to expand it, but I don’t know about growing it to more places and more people. I think publishing could be a route. I think it would be really cool to give people the tools to start their own book club. Like books published with my discussion questions at the end.” She’s also started experimenting with author events. “I was hesitant at first because I wanted people to feel comfortable saying what they really thought about the book. But having the author there does add a lot of depth. I also want to do more experiential things, like for an upcoming book there’s going to be an art element to the event.”
CA: How did you make the mental leap to feel comfortable working independently full-time?
LM: “For me, I do better when the stakes are really high. Like, I had to figure out how to pay my rent. Or when I knew 50 people were coming to an author event, I had to figure out how to deliver value to them. Yes, I work for myself, but I actually work for my reflection. If I don’t produce a good experience, I’m out of a job. And then also just realizing that all the people you see on the internet are just people. I used to work at a startup that had 50 people when I started, maybe 100 by the time I left, and so I saw the founders all the time. And they were super smart and I respected them a lot, but also, I saw that they were just people.”
She even keeps a folder for inspiration. “If I like someone’s work, I look for the earliest example of their work to remind myself that we all start not knowing what we’re doing. The folder is literally called ‘everyone started somewhere.’”
CA: What’s your advice for others looking to launch a creative business?
LM: Just start—everyone you admire did.
This conversation has been condensed and edited.
Cappuccino Thoughts Getaway
September 6–10, 2025 | Mallorca | 3 nights, 4 days
This September, we’re sailing the coast of Mallorca with just eight people aboard a private yacht for the first-ever Cappuccino Thoughts getaway. Expect cappuccinos on deck, swims in quiet coves, and long, lingering conversations. Only four cabins are available — all meals, drinks, and magic included.
If you’re curious whether it’s the right trip for you, I’d love to hop on a call or grab a coffee. Just reply or send me a note at claire@claireakkan.com.
One of my absolute favorite parts of running this small business has been collaborating with other local creatives. At one of my pop-ups, Gunnar walked in and pitched me on painting one of my bags. I had to say yes!
One of a kind, hand painted by Greenpoint artist Gunnar Magnus, this vintage Gucci bag features unique artwork, original bamboo handles, and a retro lining. A true collector’s piece.
You’ll be the star of the Kentucky Derby!
Happy 4th of July, from the hot dog eating contest in Coney Island!
Three things I love, covet, or think are worth covering.
🎨Oil Pastel Set: My big goal for 2025 was to embrace my creativity, and recently I’ve been carrying this small set of oil pastels around so I can sit down and make a quick sketch if I see something beautiful. Super portable and no clean-up required.
👗Quince Pants and Skirt: I mostly work from home and don’t like working in sweatpants, but also want something comfortable. These silk pants and this silk skirt are the perfect lightweight pieces that are a godsend in this heat.
I’m fascinated by the brand Quince’s business model, which is to copy popular items, manufacture them in similar factories, and sell them for about half the price. On the one hand, as a small designer, I don’t approve of “dupe” culture, basically knocking off other brands. On the other hand, the profit margin on a lot of clothes can be 90%, so better value is warranted.
🦪Pearl Necklace: I recently read The Matchmaker by Elin Hilderbrand (full review next week) and the main character has a signature uniform including a strand of pearls. I love the idea of adding pearls to a casual outfit. You don’t need real ones to achieve the look.This is a great affordable option.
The Wedding People by Alison Espach may just be the perfect summer read. As I mentioned in my last newsletter, in the summer, I want light fiction that’s still well-written. This hit the mark. It’s about a burnt-out English professor who goes to a hotel for a very dark reason, but ends up accidentally joining a wedding party. The book has multiple love triangles, wonderful descriptions of Newport, Rhode Island, and loads of references to classic literature from Jane Eyre to Mrs. Dalloway. If you like your summer reads with a side of snark, give it a try. Four stars.
Editor’s Note: Cappuccino Thoughts will be on vacation next week! See you back here on July 23rd!
This week I am going to learn how to play mahjong. You can find my bags here. I’m on Instagram here. If you are interested in partnering or advertising in a future Cap Thoughts issue, want to book office hours to discuss your own creative side hustles, or are a publication looking to commission a piece, email claire@claireakkan.com.
All my best,
Thanks for having me!!