A Recap of An Evening with Kevin Boehm: The Bottomless Cup
The Chicago Literary Salon — December 9, 2025
On a cold December evening, thirty-five guests stepped in from the chill and into the glow of Nic & Juniors, greeted first by candlelight… and then by a cocktail called The Resilience Gimlet.
It felt exactly right for the night ahead.
We were gathered for the second chapter of The Chicago Literary Salon, an intimate dinner-and-conversation series that brings authors and readers together around one long table. This month’s featured guest: Kevin Boehm—James Beard Award winner, co-founder of the Boka Restaurant Group, and author of the deeply vulnerable memoir The Bottomless Cup.
From the start, it was clear this wasn’t going to be “just” a book event.
After everyone settled in with their first bites and cocktails, we shifted from small talk to story.
I opened the evening with a toast, sharing the heart of The Chicago Literary Salon:
“A space where the dinner party becomes a book club, where conversation flows as easily as the wine, and where the stories on the page invite us to share the stories we carry in our own lives.”
Then we turned our attention to Kevin and The Bottomless Cup.
Kevin spoke about how the book began, not as a lifelong plan, but as a single essay about his mother that led to an email from a New York agent. What followed was years of digging into hard truths: a childhood marked by his mother’s trauma, a career built on ceaseless ambition, and the personal cost of building a hospitality empire.
One of the lines that seemed to hush the room was his reflection on success:
“I mistook magnificent moments for happy moments.”
He described the rush of opening restaurants, the dopamine hit of a busy dining room, the awards and accolades that should have felt like arrival, and yet didn’t.
“There is no finish line,” he said. “It’s all process. If you’re not enjoying the process, you won’t enjoy the win either.”
You could feel people around the table nodding. Many of us know that particular ache: the belief that the next milestone, the next promotion, the next launch will finally unlock contentment.
Kevin also spoke candidly about mental health, about being told at twenty-seven that he might be bipolar, about running from that diagnosis, and about eventually hitting rock bottom.
“Rock bottom is a gift if you can survive it,” he told us.
From there, he described rebuilding his life with intention, starting with a list of twenty things he needed to change, boundaries, therapy, medication, rest, and actually doing them.
One of the most moving parts of the conversation was Kevin’s description of hospitality as emotional work.
He told a story about a guest who brought in a treasured bottle of wine to honor his late father. The bottle was flawed; the wine undrinkable. What followed was a chain of problem-solving, generosity, and quiet improvisation that ended with the guest in tears, telling Kevin:
“You’re a beautiful liar, young man. My dad would have loved this.”
Kevin reflected:
“I became a miner of human moments.”
It was such a striking phrase—this idea that hospitality is not just about food and drink, but about searching for those small, luminous moments where people feel seen, held, and cared for.
After the moderated conversation, dinner really began—and so did the second half of the salon: the part where everyone in the room becomes part of the story.
At each place setting, guests found conversation cards inspired by The Bottomless Cup and the themes Kevin explores: ambition, identity, childhood, reinvention, and what it means to truly welcome others.
Some of the questions on the table:
When in your life has ambition served you well — and when has it gotten in your way?
What’s one goal you’ve pursued that ended up changing you more than you expected?
What do you think is the hidden cost of your current ambitions?
What’s one pattern from your childhood that you see echoing in your adult life — for better or worse?
What part of your identity do you feel you perform for others — and what part feels most true?
Think of a time when someone made you feel profoundly welcomed. What made that moment stand out?
What’s a failure you’re grateful for?
Some tables dove into ambition immediately—career pivots, burnout, the temptation to tie worth to productivity. Others started with childhood and worked forward, tracing old patterns into current choices. There was laughter, but also long, quiet pauses where someone gathered the courage to say something they weren’t expecting to say out loud.
At one point in the evening I said:
“The heart of this event is all of us bringing our own pasts, our own stories, and connecting them to the book and his story that he shared tonight.”
And that is exactly what happened. The questions were there for anyone who wanted them, but many conversations flowed naturally without them: stories about risk and reinvention, about therapy and nervous breakdowns, about complicated parents and the strange tenderness of grieving both people and pets. Guests found one another across the table with simple refrains: me too, same, I thought I was the only one.
One guest, who has known Kevin for years, pointed out that The Bottomless Cup is, in many ways, an underdog story.
He may be one of Chicago’s most influential figures in hospitality now, but he didn’t start that way. The memoir traces the long arc from a turbulent childhood, through early failures and reckless decisions, to a hard-won, more grounded version of success.
Kevin himself resisted framing the book as a hero’s journey:
“The book’s not really a hero story,” he said. “It’s probably more of a cautionary tale at times.”
And yet, there was something quietly heroic about the way he spoke—unpolished in the best way, open about mistakes, generous with his hard-earned wisdom.
By the time dessert arrived, the room felt less like “author and audience” and more like a gathering of people who had just collectively admitted that they, too, were tired of pretending everything was fine.
At the end of the evening, I raised one last glass and shared what has quickly become the refrain of this series:
“Thank you for taking a chance on the Chicago Literary Salon. We’re brand new—this is only our second event. You’ve helped create exactly what I hoped this would be: a space for deep conversation, shared experience, and meaningful connection.”
Someone had asked me earlier in the night how many people in the room I knew personally. The answer: three.
Everyone else came on a recommendation, a bookstore newsletter, a social media post, or a whispered “you should come to this” from a friend. That’s the kind of growth we care about: slow, relational, rooted in trust.
By the time Kevin began signing books—personalizing copies of The Bottomless Cup while guests lingered over the last spoonfuls of toasted coconut sorbet—the room felt full in the best possible way. Full of stories, of new connections, of the quiet relief that comes from hearing someone say the thing you’ve been afraid to name.
What’s Next
We’ll be back at Nic & Juniors in January with Amy Meyerson to discuss her emotional thriller The Water Lies, a story that explores motherhood, intuition, memory, and the quiet bonds that tie women together.
If you joined us for this evening with Kevin Boehm: thank you—for your presence, your openness, and your willingness to sit with hard questions.
And if you’re just hearing about The Chicago Literary Salon now, consider this your invitation. Pull up a chair next time. Bring your stories.
We’ll save you a seat at the table.
December 9, 2025 @ 6pm
Step into the adrenaline-fueled world of Michelin stars, opening nights, and the unrelenting pursuit of hospitality with award-winning restaurateur and author Kevin Boehm, as he joins us for the second chapter of the Chicago Literary Salon to discuss his unforgettable memoir, The Bottomless Cup.
Vibrant, funny, and deeply human, The Bottomless Cup traces Boehm’s remarkable journey—from dropping out of college and sleeping in his car to co-founding one of the most successful restaurant groups in the country. Along the way, he finds home in the chaos of the kitchen, the poetry of service, and the fellowship of broken-yet-brilliant souls who come alive when the dining room lights dim.
Whether he’s dodging disaster on the opening night of a six-table bistro or accepting the James Beard Award for Outstanding Restaurateur, Boehm’s story is a masterclass in grit, ambition, and finding your place in the world—one plate at a time.
Your evening includes:
A signed hardcover copy of The Bottomless Cup: A Memoir of Secrets, Restaurants, and Forgiveness purchased from our partner bookstore, Three Avenues Bookshop
A thoughtfully curated, multi-course menu by Nic + Juniors, featuring:
A welcome cocktail
Two passed bites
Seasonal salad
Handmade pasta
Entree
A sweet finish
A live conversation with Kevin Boehm on risk, reinvention, and the beauty of building something that lasts
Elegantly designed conversation prompts to inspire connection—no prior reading required
Whether you’re drawn to culinary culture, memoirs of resilience, or a behind-the-scenes look at the restaurant industry, this is your invitation to gather, dine, and dive deep into a story only Kevin Boehm could tell.
Seating is extremely limited. Reserve your seat today.
About The Bottomless Cup:
An eye-opening, entertaining, and unflinchingly honest memoir that reads like The Tender Bar meets The Bear
James Beard Award–winning restaurateur Kevin Boehm has opened 40 restaurants in his 30-year career. He’s worked with hard-core line cooks and celebrity chefs, suffered embarrassing setbacks, and won Michelin stars. Today his Boka Group is one of the most successful restaurant companies in the world.
But Boehm’s path was a complicated one. A turbulent family life and a shocking revelation about his father drove him out into the world in search of a home. He found one in restaurants. Amidst other gifted and damaged people, he discovered the magic of hospitality and the thrill of a dining room on the edge of chaos.
The Bottomless Cup is Boehm’s vibrant, funny and frank account of a life in and out of restaurants. This is a memoir about dropping out and finding your place, about opening nights and what comes after, about chefs, partners, guests, and critics. The Bottomless Cup is a story of ambition and adrenaline, of reaching remarkable highs and reckoning with the costs.
About Kevin Boehm:
James Beard Award–winning restaurateur Kevin Boehm has opened more than 50 restaurants over the past 30 years, building Boka Restaurant Group into one of the most celebrated hospitality companies in the world. With partner Rob Katz, he has launched over 40 acclaimed concepts, earning Michelin stars, national awards, and recognition from The New York Times, Robb Report, Eater, and the Chicago Tribune. In 2019, the duo won the James Beard Award for Outstanding Restaurateur.
Beyond restaurants, Boehm co-founded the wellness club Bian, contributes writing to publications such as Esquire and Fast Company, and frequently speaks at leading industry events and universities. His debut memoir, The Bottomless Cup (Abrams Press), publishes in fall 2025.