Milk Bar Founder Christina Tosi on Building, Burnout and Resetting

30 Sep 2026 · 1 h 10 min · 24 chapters

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In short

Christina Tosi (Milk Bar founder) discusses her “cannonball” approach to risk and failure, how she learned business by working “et cetera” roles at Momofuku under David Chang, and what it costs (emotionally and operationally) to scale a creative food brand. She also covers burnout, resetting after stepping down as CEO, and how she keeps creativity alive while mass-producing desserts.

Guests

Christina Tosi, founder of Milk Bar; former hire by David Chang to write a HACCP safety plan; creator behind compost cookie, cereal milk soft serve, compost cookie cereal, and other Milk Bar inventions. Maria Sharapova is the host (not a guest).

Key claims

Failing should be rebranded as useful; scale can kill creativity, so teams and “blinders” are needed; dessert is a form of self-care; leadership and boundaries matter; one day at a time and “marathon, not sprint” thinking sustain long-term success; she stepped down from CEO because she felt empty and wasn’t able to give fully to family or the business.

Notable examples

The “Milk Bar Life” healthy line (green juices, yogurt parfaits, coffee) launched and underperformed; Milk Bar’s origin next to Momofuku with late-night lines; her “et cetera” job title at Momofuku.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Maria and Christina Reconnect

1:44 to 2:49

Maria reflects on her last visit with Christina, discussing their mutual business journeys.

“This week on Bird's Eye View, I'm joined by Jessica Shepard of the Dallas Wings.”

Cannonballing Into Opportunities

2:49 to 6:15

Christina shares her cannonball personality and how it has shaped her career and personal life.

“I remember the last time I saw you, I was visiting your New York City office, and you were in the midst of it.”

Lessons from David Chang

6:15 to 11:25

Christina discusses her time working with David Chang and the valuable lessons learned.

“I start these interviews with a quote by the guest and everyone's always a little scared.”

Building a Creative Business

11:25 to 14:00

Christina elaborates on the challenges and successes of scaling a creative business.

“At that point, you pastry was not in your universe.”

The Marathon Mindset in Life and Business

14:00 to 16:43

Learn about the importance of viewing challenges as long-term hurdles rather than sprinting towards quick results.

“I'm a very, um, like turn my homework in student.”

Navigating Bad Bosses and Learning Opportunities

16:43 to 19:10

Discover how to maintain personal integrity and learn from different experiences with bosses, both good and bad.

“Like if it came quicker, would that have produced a better, stronger, more resilient, brilliant Maria or not?”

The Birth of Milk Bar from Momofuku

19:10 to 22:24

Explore how Christina Tosi transitioned from working at Momofuku to opening her own bakery, Milk Bar.

“because that's the origin of Milk Bar you get the space next to Momofuku and it ends up being your bakery.”

New York City Bakery Culture and Celebrity Encounters

22:24 to 26:04

Hear about the unique late-night culture of Milk Bar and celebrity interactions that shaped its identity.

“But when I look back to that, I think here's David, who's an accomplished entrepreneur's open Momofoco.”

Turning Passion into a Business

26:04 to 28:00

Gain insights on how to transform personal passions into a successful business venture while acknowledging the challenges.

“What is some advice that you would have for people that really want to turn a passion into something that's fruitful?”

Finding Joy in Hardship

28:00 to 29:42

Exploring how challenges can lead to joy and personal fulfillment.

“Maybe what I want to do is what you want to do.”
Show all 24 chapters

The Culinary Journey of Christina Tosi

29:42 to 31:35

Christina discusses her journey in the culinary world and the importance of training.

“Like plug your nose and tuck your knees and go for it.”

The Role of Nostalgia in Creativity

31:35 to 32:40

How childhood memories influence culinary creativity and product development.

“I wish I could say it happens every day in my life now, but for these moments, especially, and when I'm looking for grounding, I remember myself like you've been training for this moment your entire life.”

Overcoming Doubts and Trusting the Process

32:40 to 36:22

Maria and Christina reflect on handling doubts and trusting oneself in competitive environments.

“It's like, how do you quiet any other voice that might be popping up into your head or coming out?”

Building a Business from Passion

36:22 to 41:22

Christina shares her journey of turning her passion for baking into a successful business.

“And for more than a decade, I've hosted the podcast Criminal, telling stories about people who've done wrong, been wronged, or gotten caught somewhere in the middle.”

Empowering Women in Leadership

41:22 to 42:04

Discussing the importance of hiring women in leadership roles and breaking barriers.

“But these are all like little, again, like you've been training for this moment your whole life.”

Importance of Women in Leadership

42:04 to 43:19

Christina discusses her experience with women in leadership roles and the importance of creating space for them.

“Like not that the people that I worked for prior didn't believe in women, but I had girl, it wasn't just getting a foot in a door.”

Challenges of Scaling a Creative Business

43:21 to 45:13

The conversation shifts to the struggles of maintaining creativity while scaling the business.

“Like as much as I found my people, like as much as you find your people and that's your responsibility, your people will also find you.”

Learning from Failure

45:14 to 51:36

Christina shares her personal experiences with failure and the lessons learned from launching a new product line.

“And with that, occasionally comes failure and I feel like I'm sitting across someone that has a healthy relationship with failure and failing forward and acknowledging that in your profession.”

Personal Reflections on Work-Life Balance

51:37 to 54:01

A discussion about Christina's decision to step down as CEO and the impact on her personal life and happiness.

“And you go, ooh, we learned something, didn't we?”

Making Bold Life Changes

54:02 to 56:06

Christina talks about moving to Nashville and the decision-making process involved in life changes.

“Milk bar was my everything on every level.”

Building a New Life: Embracing Change

56:06 to 58:52

Discover the excitement and challenges of moving to a new city and creating a fresh start.

“And I remember one conversation we were having where he's like, well, what about this?”

Top Desserts Worth Traveling For

58:53 to 1:01:25

Learn about Christina Tosi's favorite desserts and hidden gems around the world.

“To wrap this up before we get to the pretty tough questions.”

Unlearning and Embracing Perfection

1:01:26 to 1:04:29

Explore the relationship between perfectionism and creativity in personal and professional life.

“Cookie dough, making your own ice cream sundaes.”

Finding Strength and Beauty

1:04:30 to 1:06:58

Understand how overcoming challenges can lead to feeling tough and beautiful.

“One could say that's unhealthy, but part of me is also like, and that's also part of you.”
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Transcript

Automatic transcript. May contain errors.

0:00We talk about this all the time, right? Like if you're not taking risks, you're not failing. And if you're not failing, you have no opportunity to win. You have no opportunity to win if you haven't put yourself out there. Okay. Favorite failure. That doesn't sound good. So many.

0:19my guest today is a literal sweetheart she was hired by david chang to write a safety plan she left with a james beard award a dessert empire and a cookie that broke the internet this is christina tosi the founder of milk bar and the woman behind the compost cookie cereal milk soft serve and a business that started as a side hustle christina's fearless mindset took her from suburban Ohio to French pastry school and fine dining kitchens to building one of the most recognizable dessert brands in America. But this conversation isn't just cookies and cake. We're getting into what it actually costs to scale a creative business, the burnout that comes with it, and how you have to get comfortable with plenty of failure if you want to find your way to success.

1:04I'm Maria Sharapova, and this is Pretty Tough.

1:14Your heart can tell you a lot about your health. Apple Watch Series 12 measures your heart rate every five seconds with the most accurate heart rate sensing in a wearable. So your vitals app, now with heart rate variability, can tell you when something is off. And your readiness score can let you know when to rest and when to push. Hear the story in every heartbeat with Apple Watch Series 12. The features described are for wellness purposes only and not for medical use. iPhone 11 or later required. Based on Apple conducted study of heart rate accuracy, August 2026. Visit Apple.com slash Apple Watch Series 12.

2:14Hey, it's Sue Bird. This week on Bird's Eye View, I'm joined by Jessica Shepard of the Dallas Wings. Jess and I get into how playing overseas helped her rediscover her love of basketball, why Paige Beckers is one of the best teammates she's ever had, and what the Wings need to do to find success in the playoffs. Plus, in Sue's view, I share my thoughts on the 2026 WNBA Awards race, including the contest for MVP between this season's frontrunners Asia Wilson, Kelsey Mitchell, and yes, rookie Olivia Miles. Check out this week's Bird's Eye View on YouTube and wherever you get your podcasts. Christina, welcome to Pretty Tough.

2:50I remember the last time I saw you, I was visiting your New York City office, and you were in the midst of it. You had so much going on. This was before our kids came into our lives. You were work, work, work. You were so focused. You were so determined. But you were also so joyful. And I came to visit you at a time where I was growing Sugar Pova. I was going to say, you brought me candy. I brought you candy. There's only one response to that, which is pure, unadulterated joy. I loved meeting you at a time in my career where I already had a focus and a profession that I was totally dedicated to.

3:28But I also had a side project, which was a real business in the candy space. And I came to you with so many questions. and it was just like a woman-to-woman conversation about experience, about business, about trial and error and how to scale, right? Because we were a packaged good and you were just about to get into it. And so like you shared your time and your wisdom and it wasn't like anything formal came out of it, but just spending time in a room with someone that knows what it's like to go through the ins and outs of a specific business is so helpful to say the least. Oh my gosh. Well, can I tell you when I was like, Maria Sharapova's coming to her office, everyone was like, and also this idea, this is like what I just love.

4:21One of the like many reasons that I just adore you are you couldn't even see yourself at that moment to be like, I'm sure you were in town because you had a very important match. We're just coming from a very important match. and you were just like in your free time building this brilliant business like for me you just defined all the odds of like what a human can be what like a badass business babe could be and also like what you can do with your day if you're thoughtful and passionate and girl you bootstrapped and crushed so hard that was that was like from a business standpoint one of them how much traction you got by doing it all yourself.

4:59I was so impressed. So impressed. What I loved about that day is that there was no agenda. And this is like more than five, seven years ago. And it was just about two individuals that are trying to learn from one another, which happens so rarely. I was going to say you don't find it. It doesn't happen enough. And you just want to learn because you're sitting across someone that knows it a little bit better or has a network that could potentially unlock something for you and just just being comfortable in their presence and being like I know what you're going through here's how I'm handling it so but I feel like that's a testament to one your humility which is it was like a pinch me moment myself to understand you as you are, which is like completely humble, like guard down, curious, open, already so successful in what you had built up into that point.

5:59And I learned so much just by like the validation of being like, oh, really? But real people exist, like real women exist and will 100 % just show up at your office to hang out and trade ideas. Anyways, we do need more of it in the world. Anyways, let's start this episode. I start these interviews with a quote by the guest and everyone's always a little scared. They're like, what did I say? I love this quote. You say, I'm very much a cannonball personality. I don't need to know any of the details. I just cannonball in and figure it out. And this was in the context of accepting your first job out of college, running a bakery, where you had absolutely zero experience of what you were doing.

6:50Do you still hold true to that mentality 20 years plus later? I think it 100%. I think it's both been a secret to loving and living life as just a person. it's been a secret to loving the people in my life it's definitely been a secret to success for milk bar it's also been a secret to failure for milk bar because if you're not taking risks and cannonballing in you're not failing but i also think failing should be rebranded because it's actually a good thing not a bad thing and it's been a secret to success in i think my personal life too my husband is not a cannonballer he's an analyzer and i do love the yin yang of that.

7:31And one of my kids is more of a cannonballer than the other one, TBD. But it's just who I am. I don't think it is even about how I was raised. It just is who I am. When was the last time that that cannonball mentality backfired? Oh, my gosh. It fired back pretty regularly at work. But I also I just believe so much in that mentality, whether it's the sort of like, I think we should do this flavor story, or I think we should pursue this format, or let's look at, let's look at building a bakery here, or, you know, let's build this in the aisles of the grocery store. But I'm, I'm not afraid of failing.

8:13Do you hold that mentality with your family and your children? A hundred percent. I thought you were going to say in life, and I was going to say, oh my gosh, we just moved to Nashville. And I just, I mean, Maria, I've been to Nashville once before in my life, before I moved there for like a day and was just, Will really wanted to move for like really fun, very specific, strategic, very well thought out research reasons. And as soon as I said yes, I was like, I don't need to know. I don't need to go there. Why would I go there? That doesn't make any sense. I moved to New York City 25 years ago or however long it's been with the same mentality of like once I decide that that's like right and it feels right and the decision is not here it's here it's not in the head it's in like the heart of the belly.

9:03After this bakery gig you go to culinary school you work in very fancy restaurants and then comes 2005 and you're hired by David Chang and for those who don't know who was he on the food scene at the time? Dave was it. Dave was what was happening at this pivotal point in food in 2005. So if you think about it, there were food blogs. Food did not have the stronghold on us in our lives that it does today. Our access to flavors and innovation and creativity through food was just starting to pick up. You had cuisines, right? You could, like, eat French. You could eat at a diner. You could eat at a steakhouse.

9:52You could have Italian food. Like, that was the story. You could go to Chinatown for a Peking Dut. Yeah, that was the news. But really interesting people and chefs like Wiley Dufresne were starting to do really interesting, like, the intersection of food and science things for food. But again, he was even an outlier. Dave came onto the scene, and he similarly, formerly trained savory chef um had worked for all the great he is korean american by birth but fell in love with japan and he just decided that he was going to open a japanese ramen shop on first avenue between 10th and 11th streets in the east village and when the idea of a ramen shop didn't really get the job done he just woke up one day and decided i'm gonna cook whatever the blank I want because Dave is also very much a cannonballer.

10:41He also likes to use bad words. He redefined what the dining landscape was both in that you could be a startup business, like literally Momofuku Noodle Bar was the name of the restaurant, was a hallway of a restaurant with 12 seats. There was no reservations. You could not make any modifications to the food and what was on the menu, whatever that man wanted to cook that day at a very accessible price point. And he really brought the aspirational, accessible, democratizing, savory food to life. And I just loved everything about what he was doing and nobody else was doing it. And I was really at a miss of like, I'm not a fine dining pastry chef.

11:23I had spent like a decade chasing like white tablecloth pastry chef. At that point, you pastry was not in your universe. You loved it, but that wasn't your core science. What was missing for me was I'm a home baker first, man. The spirit of handing someone a warm cookie or like brownie in a Ziploc baggie. I went to culinary school thinking I'm going to be the best pastry chef there. If I'm going to make dessert for a living, which was my dream, I'm going to be the best possible version of that. That was to become a pastry chef. and as I got into pastry chef land I was like this feels really fussy for the my why I love the art of it but the why is really about the heart the heart string the emotion and so I was I was on my own little quest to figure out like okay if I'm not a fine dining best in class pastry chef in the terms of now, what am I?

12:25And I found a home at Momofuku because they at least were doing what I knew the spirit of what I wanted to do was through savory, but they had no desserts on the menu. There was no reason for me to be there. But those years were so informative because you described the job as anything and everything. My job title was et cetera. We would literally joke. Dave was like, I love that. He hired me to write this HACCP plan, which is a very dorky food science plan because I also am a little bit of like a mad scientist in my own right. And once I had helped him write this HACCP plan for a very dorky cooking technique, he was like, well, just come and work for me.

13:05And I was like, what would I be doing? Like, you literally don't even have dessert on the menu. And I don't want to be a pastry chef in that way anyways for a restaurant. And he was like, you just anything and everything, which is very much the way two cannonballers speak to one another. And I was like, great. What is that? And he's like, at some point I needed to write a title on a form for like the bank doing payroll one day or whatever. And it was like, what's your title? And I was like, Dave, what's my title? And he was like, it's et cetera. And I was like, that's, that's perfect for me for a cannonballer.

13:36That's a very self-proclaimed title. I love how you described it because once you've been the plumber, the electrician, the contractor, the safety consultant. It's like, don't put me in a box, babe. I would take et cetera any day of my life as a job title. What were some of the most important lessons during that time before you created your own business? I think what I saw in Dave and what I found in Dave was I'm a very, um, like turn my homework in student. And Dave was very much like, well, technically I'm in charge, but stop trying to report to me. Stop trying to seek validation from me. Like what I saw that he was building when I took a step back was an environment of really passionate people that had their own drive and that he knew had their own self-worth.

14:25And he just had to like untrain some of the pieces of really what really driven people on their way up are trained to implicitly have in themselves. He taught me the power of what really delicious food on your terms can stand for and mean. I mean, Maria, I can't remember what we paid on rent for the original Momofuku noodle bar, but, you know, in like nowadays terms, it was nothing. It was a hole in the wall, right? That you can create magic and do something really meaningful, even if it's not the best location with the most expressed business plan. I mean, there was no business plan, right? Like there You created the business plan.

15:04Yeah, it was you create your own destiny. And you bring people along the way that you believe in and they believe in you in a two-way street, not a one-way street, right, of hiring. And it is a marathon, not a sprint, which I knew on some level. But watching him do it day in and day out, like I became just obsessed with that spirit. And a lot of it was validation for the cannonball spirit of like, no, if you're going to do it, you do it all the way every day. With your heart and soul. Yeah. Yeah. It's not nine to five. Balance is for the bees. I love the term. It's not a sprint. It's a marathon.

15:46And it's something that my father said to me when I was just a teenager playing one of my first Grand Slams. And the expectations were so high from the outside world, but especially for myself. Like I wanted it so bad. I didn't want the fourth round. I didn't want the semifinals. I wanted the trophy. Remember losing a hard match. It's early in the tournament. I expected myself to do better. I come off the court and his first words are not like, you know, you missed too many forehands. You didn't take a chance on that break point. It was, this is not a sprint. It's a marathon. So I love that because I think it applies to so many industries.

16:23It doesn't matter if you're a pastry chef or an athlete or an astronaut or you're in the office. Like you got to you got to think long term. And if the results come sooner than you expect, congratulations. You did it. But also a little bit like if you won that, would you be who you are today? You know what I mean? Like if it came quicker, would that have produced a better, stronger, more resilient, brilliant Maria or not? Like I dare to say not. It's a little bit of like I always have to remind myself like it's a marathon, not a sprinter. My other like colloquialism is this is a hurdle, not the finish line.

17:01Like when you have a really when you get caught in the cannibal spirit, you're like, this is not the finish line. This is a hurdle. You can call it what it is. You can name it. Sometimes you got to name it. But like this is you were just this is just one stop along the way. And for people whose bosses throw so much at them, when it doesn't feel like a collaboration, when you do feel like you could learn from all these different jobs within one organization, but you need to set your own boundaries, what advice would you have? I think you define your own self-worth but I would also challenge all of us to say one there's good and bad to learn from bosses like I've had really bad bosses and I've had really great bosses and in the bad bosses it wasn't I what I never allowed is the inner dialogue to be like well this person's a bad boss right so like screw them or like I'm out of here what have you right it's the it's the conversation, the internal dialogue of like, why am I here?

18:01What can I learn from this? How can this shape me? And what kind of person do I want to be? Like, am I going to walk off the job if it's a bad boss? Or am I going to, am I the type of person that is a person of their word, even if somebody isn't? And like, there's a lot of good I can still learn here. And I think that those are important boundary pieces because I think we live in a world sometimes where more often than not, we either don't speak our mind or we over speak our feelings in the moment as opposed to really grounding ourselves and going like, all right, what is this hurdle put in place for, right?

18:38Is it because like, if I feel like I don't have a boundary, is it because I'm feeling overworked or is it something else? Is this the place I'm supposed to be? Is this what I'm supposed to be doing? Like, what is this voice in my head or in my heart or what is it trying to tell me as opposed to just I think a lot of times we need jerk react and that either leads to us lashing out or acting out and I think there's a deeper dialogue in there so that would that would be like the first place that I would say to start so let's talk about what happens next at Momofuku because that's the origin of Milk Bar you get the space next to Momofuku and it ends up being your bakery.

19:20Yeah. Milk bars born. Yes. How did that happen? I was in the etc role. We had a new landlord and this laundromat next door whose basement we were just using at Momofuku. And the landlord was like, this space is now for rent. And from a Momofuku angle, we sort of thought to ourselves, well, we don't want someone we don't know literally coming in right next to us. It's better for us if we can, you know, control our own destiny, be master of our own destiny. And at that time I was like, you know, et cetera by day, but I had started to put like little bites of something sweet on the dessert menus at Momofuku, but like not as a dessert format, right?

20:05Like, oh, you just happen to be able to get soft serve at Noodle Bar or you can get this really cool strawberry shortcake kind of composed, decomposed dish, but we would like hide it under the farmer's market section of Sombar, right? Just to sort of have an outlet. But I would do all that dessert prep late at night, like started at 2 a.m. Best friend was the overnight prep cook. What? 2 a.m.? In the Sombar basement. And Dave, I think, started to see the like, you need some space. And he knew that my dream was to bake and was just sort of like, at some point you're going to get sick of this. Like at some point you're going to leave, like we joke like that, at some point you're going to leave me.

20:44And it's like, yeah, but leaving is not necessarily, you know, leaving is not a bad thing. You've got to celebrate people when they take flight. And his way, I think, of celebrating it was like, you should take the space next door. You should take the space next door. We'll be neighbors. You should just put whatever is in your crazy brain on the menu and just go. And give it a shot. And just give it a shot. I mean, as you're saying that, it's almost as if he believed in the business side of Christina before you did. That's interesting. Because you were, I mean, you were creating these dessert concoctions.

21:21You were experimenting. You loved it. But did you think that it could potentially be a business? I mean, I thought it would be a little like Meg Ryan. You got mail. Like, I was going to be a little shopkeep one day. But like maybe when I was 60, you know what I mean? Like I'm always a dreamer, but I was definitely like in my dreamer era of just I loved working with Dave and I also loved dreaming. And I think that there's a role that we can play in each other's lives when you know someone well enough. Like everyone needs a good hearty push sometimes. I think that's another thing. Maybe we've become like a little too soft about that.

21:59Or someone that just that believes in you a little bit more in that moment than you believe in yourself. Or maybe it's not even that you don't believe in yourself. You it's a little bit of like true friendship is like every once in a while you just got to turn the mirror around on the person that where it's like I can see you. I don't know why you can't see yourself. But here, let me show you what I can see right now. And he did that for me. But when I look back to that, I think here's David, who's an accomplished entrepreneur's open Momofoco. It's got a big name. There is some risk in opening your bakery next to an establishment in some ways.

22:41I saw it as a platform. Like I saw it as I don't have to worry about marketing this. I don't have to worry about I mean, I was I'm always worried about whether someone's going to show up just because that's like my mentality. But it was I saw it as like a springboard. True. Like, let's bring it back to cannibal mentality. Like it gave me leverage. I was like, at least they know with Momofuku, it's going to be big flavors. It's going to be bold flavors. It's going to be absolutely delicious. And that feels like an easy opt in. because I bake the way Dave cooks, right? We blur the lines. We have big flavors.

23:17Like we're obsessed with what we make and all we want to do is feed you and make you happy. And I had this idea that a bakery of all the things that I love to like push the edges of, I had this idea that this bakery was going to open at six or 7 a.m. because that's what time a bakery opens. And then it would get really slow by like 5 p.m. because this is like old school bakery mentality but because we were connected from a real estate standpoint sambar didn't close into momofuku didn't close until 2 a.m and so i was like well it's fine we're gonna be here baking we'll just keep the door open until 2 a.m and maria i kid you not like we we had lines in the morning but you know our busiest time 10 p.m to 2 a.m because everyone everyone that would leave momofuku would be like i'm trying to get some milk bar i'm trying to get Whatever the scene is that's happening in there, Lady Gaga would stand in line next to, you know, freaking John Doe just to get their hands on some cereal milk soft serve or a birthday truffle or whatever it is that they were noshing on until the early hours of the morning.

24:24Did you see her in line? Yeah, but like I'm like busy trying to pull a cake. Lady Gaga's in line to your bakery? But this is also like she was still Lady Gaga, but like she was becoming like, you know what I mean? And it was like, I also think the best way to welcome someone in in New York City is to not like not make a fuss. It's different than life in L.A. I'm curious about your opinion on it. Like in New York, part of New York is just like everyone's just trying to be a New Yorker. Like Anderson Cooper would just pull up to get some on a bike in the neighborhood to like get his milk bar pie.

24:53He doesn't want to fuss, man. That's like part of the New York City having the like swagger. We're in L.A. It's different. Very different. But also like playing in the U.S. Open, you know, you drive through these official cars that had U.S. Open branding and it would be slightly annoying because as you're driving through the city to the tennis, everyone knows that there is an athlete like, you know, blackout windows. No one sees who you are, but they still know that there is someone from the U.S. Open in this car. Who is it? And then the moments where you get to your hotel and you take a cab, that yellow cab to dinner, and you're just sitting there anonymously.

25:31I was like, this is the dream. This is the New York City I know. Anonymity for my freaking fellow introvert. That's it, right? Yes. There's something about that that is like, I hope that New York City always maintains the richness of that. Because everyone's just feeling themselves and doing their own thing. Doing their own thing. You're such a phenomenal example of turning something that is joyful and something that you loved into a business. I don't think many people find themselves in a job that comes from personal love or, you know, figuring out how to turn a passion into a proper business.

26:15What is some advice that you would have for people that really want to turn a passion into something that's fruitful? I mean, I had a lot of really positive modeling as a kid. My mom, actually by both of my parents, my dad, most passionate agricultural economist you've ever met, which feels crazy to say. And my mom, most passionate accountant you've ever met. I think that they found my mom specifically found a way to bridge her love of numbers with her sort of like arts and craftsy love of baking and like making things funny to keep it real mentality. She would make like scavenger hunts for she was the managing.

26:57She rose to a managing partner of an accounting firm. She would make grown accountant firm partner men go for scavenger hunts to find their yearly bonuses. Like she really she found ways to bring things into her workplace to bring more of who she was and give the opportunity, the invitation to other people to bring more of that. But I think in pockets of joy, pockets of joy, which I think is really important. And I think depending on where people are along the way, like I say this all the way to like people that are in high school or in college. I mean, honestly, because I'm a cannonballer and I thought I'd open this bakery at like 65.

27:38Like, you're not behind. Like, today is today. You have time, Christina. You have time. And then also what I'd say is, like, you don't have to have it all figured out. You just have to start paying attention. Because what I find oftentimes people go, but I don't know what I'm passionate about. Or they, like, sort of mask or they think that, like, modeling what they see maybe on social media are like, oh, maybe I'll do this. Maybe you seem really happy. Maybe what I want to do is what you want to do. And it's like, don't try and don't do that. It ends up being about someone else and not them. Just start paying attention to what makes you feel great.

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28:13Like, what are you interested in? What makes you happy? What brings you that little spark of joy? Even if it's hard. Oh, don't. The hard is not part of the equation. You're just in like, what makes you like, just pay attention. Second part is just so you know, it's going to be hard. Anything in life worth going after is going to be hard. Hard is part of the joy equation, don't you think? I, yes. If you just woke up. I lived it. Yeah. Literally, I mean, I know. Some of my joyful moments came from pain and injuries and losses and all the lessons that, you know, contribute to one victory, by the way, just sometimes one.

28:55Because how would victory feel if it wasn't hard to achieve? Like the whole point is mind over matter. Like that is part, heart is part of the joy equation. So if you have heart in your brain, one, what I might say to you is like, oh my God, that's great. What is it that you're worried about that you want to do that's so hard? That might actually be exactly what needs to happen. But also if you don't love the idea of whatever that joyful thing is, like early in the morning, long before anyone else wakes up, late at night, long after everyone goes to bed, I'm talking nights, weekends. You're not going to any family function.

29:32There's no weddings. There's no anything. If that's the thing that you're still like, yes, I still want to do it. That's it. Cannonball. There's your answer. Like plug your nose and tuck your knees and go for it. So you're running Milk Bar and your inventions become these full on crazes. You've got cereal milk ice cream. You've got cakes without side frosting. I'd say that's scandalous, Christina. They call them naked cakes now, Maria. I don't know who came up with the term, but I think it's hilarious. You've got compost cookies. Like, how important was the official culinary training to get to that point of experimentation and doing things that are out of the box?

30:20For me, it was essential. I mean, I think everyone has their own journey. I'm the type of person that loves to learn and I love to learn in a formal setting. Certainly at that point I did. I had to learn from my bad bosses, learn from my great bosses, learn from fine dining French cuisine, learn from an amazing Austrian pastry chef, learn from a molecular gastronomist, right? I had to learn from my grandmas. Like I had to learn from all of them to understand where I fit in and what my contribution was, how I saw the world, how the world looked through these eyes, everything about it was important.

31:00I think also like remembering to protect the like nostalgia in me, like how do you come up with cereal milk if you don't protect the like mornings as a kid where you could like bottoms up slurp the bowl? We call it fancy cereal. Fancy cereal is allotted on weekends only in my house. But like Like if you don't know what the, you know, the flavor of like milk that's been sopping up golden grams or Captain Crunch or Frosted Flakes, you know, or Lucky Charms. Yummy, I'm hungry just listening to you. And like being a, being a like nostalgist in that way, like knowing yourself and protecting those parts of you, no matter what else was happening in your life otherwise.

31:44So for me, I think about it like this. every day. I wish I could say it happens every day in my life now, but for these moments, especially, and when I'm looking for grounding, I remember myself like you've been training for this moment your entire life. It's not what you've been training for, for the last 10 years or 20 years in like pastry world. It's like, you've been training for this moment, this dilemma, this hurdle, or this success. You've been training for it your entire life. So like pull, Pull from all the different ways and places that you know yourself. Like that is your answer. We say that often.

32:20Like one, limitation breeds the highest form of innovation. But also the answer is always somewhere in this room. It's just about remembering to be human enough to know it. And is it also a bit of trust of just trusting that decision and going with it and not second guessing? For sure. Yeah. A hundred percent. It's like, how do you quiet any other voice that might be popping up into your head or coming out? I mean, what is it like, Maria, to be the champion that you are and stand on that court? What literally what dialogue comes up? Because it's I can't imagine that it's always like you got this girl.

33:00No, you got this. You're a champion. Snatch it. It is so up and down. I mean, within just one match, within 60 to 90 minutes, you can have some of the greatest thoughts and you can have a little devil in that head that just keeps telling you you can't do it. And then you're like, no, no, no, but I just did. I just I just overcame you. And now you're back. It's just it's a constant push and pull. What's your secret? Like, how do you know? Well, I don't play anymore. I know, but like, how do you know? Because I imagine you apply it every day. It's motherhood. I mean, a four-year-old little boy, girl, that's, you know what it's like.

33:40I thought you got spicier than a grand slip, you know, like, how do you do it in your, how did you do it then? It's a loaded question. How do you do it now? I was prepared to ask you the questions. I love that you're throwing it back at me. I always remembered that it's not about the first point or the first game or what you say or do in the beginning, but it's the entire journey. So it could be the length of the match or it could be the length of the tournament. And things happen fast, especially in sport. And you can have a great moment and you can be confident and you can be prepared and you're surprised by the outcome when it doesn't go your way.

34:21but I often flip that script because I would come in feeling like I'm just coming off an injury. I haven't played a lot of matches. You know, I'm not feeling my best. I don't know if my body's going to withstand like the physicality of these matches and the grind day in, day out. And you surprise yourself. And part of that is letting go and trusting the process. Because doubts are part of any profession. They come in and out. but you just have to trust it. It's not about the beginning. It's not about just one event. It's the marathon and finding, finding the process joyful. Like I love practicing because I got to like huddle with my team and, you know, even the water breaks, people joke like, oh, you love the water breaks.

35:10No shit. It's the easiest part, but I love the water breaks because I would have these few minutes with my dad where it would be almost philosophical, where it wasn't about technique, it wasn't about rhythm or what you have to do on the court. It was just zooming out of the intensity of one profession and being like, I can do this. I believe in myself. I have someone that's watched me grow up that is supporting me. Look how far we have come. We didn't come here because we didn't try because you know we didn't follow our instinct we might be in a rough patch but like we're gonna get through this and to have someone that believes in you like on on your side is really special and then you go out and you keep practicing and you know you still have tough moments but you overcome and I look back to those moments of you know with my coaches or my team members because on the official stadium you're on you're there on your own but in the moments that no one sees, you're there with your team.

36:17And those are, those are what really makes it. Like your grounding moments. Yeah, they really were. It's the stuff you don't see. It's the stuff that you don't see.

36:33I'm Phoebe Judge. And for more than a decade, I've hosted the podcast Criminal, telling stories about people who've done wrong, been wronged, or gotten caught somewhere in the middle. But while I was starting one of the very first true crime podcasts out there, I was also taking phone calls from my sister from prison. This fall, I'm going on tour and I'm telling a story I've never told before. My own. Get tickets at thisiscriminal.com slash live.

37:05so it's one thing to wear a chef's hat and it's another thing to wear a business hat how did you learn through this process of baking and working with dave and the restaurant to turn your hobby into a business i mean i learned one day at a time like i i i have the financial acumen because of my mom as an accountant, but like she taught me how to balance a checkbook, not how to create a business plan of which, by the way, we still don't have one. I mean, we have strategy and now because we're, you know, we're like a business that has to take themselves a little seriously, but not not seriously, seriously.

37:51I learned one day at a time. I think that's like another bit about life is maybe it's one day at a time. It's one day at a time and you stack up the days and they total something right it is no one's learning anything overnight no one's expecting you to become anything overnight but it's one day it's one challenge it's one late night at a time and maybe it's many late nights stacked up but one day at a time and I I have had to move like the dream the goalposts of the dream further and further because as you get close to nearing a goal I imagine the same for you you have to start you have to learn how to dream bigger and dream bigger and with those dreams come responsibilities and to your point hats you're gonna have to learn how to wear um and I think along the way part of part of I know the secret to myself is mastering myself is I have to trick myself into doing things whether that's like tricking myself into like not eating dessert at every meal tricking myself into to learning how to do payroll and being excited about doing payroll.

39:01I mean, I don't do payroll anymore. Somebody else does. So is it getting excited about things that are just not like happy or joyful or not full of sugar? For me, it was like, what's your carrot? And it's like, oh my gosh, well, it's the same like bad boss mentality of like, what is like the inner dialogue here? And it's like payroll. I was like, right. I mean, I literally would bring a three pack of truffles to my desk to do payroll on my team like just set an hour and a half for this call because if if I don't answer to this email it's because I'm I'm internally ignoring it it's like momentum right so like how do you trick yourself into being the person that you want to be but the other voices aren't going to let you or for payroll I'd be like but you want to know what Christina like girl you have a business where people are on payroll and there is health insurance and vision and 401k and they can count on you you remember when you work jobs where you didn't even know if you were gonna get paid that week not because you didn't work but because right of like don't let the voice in your head I think again we think like so much of it is like the mental grit right of like how do you be strong and sharp with your own brain but um that's a lot of it and it's the it's the it's one day at a time and like one day is never too precious for a high or a low right like don't believe your own hype in a day and the low of a day does not define tomorrow sort of thing it's asking for help it's being resourceful for the longest time I would um I demanded of myself to work the job whether that was human resources or ops or the delivery driver So you went in and worked yourself?

40:44Pick, pack, ship person. Yeah. Like the second we thought we needed a new function, I'd be like, okay, well, I want to understand what the function is. What is it like to work this job? What are the highs and the lows? What kind of personality would it take? Go back to everything and everything. Et cetera, et cetera. Yeah. And then how do I find someone that can be better than me at it? It's another great lesson. And in that finding someone that's better than me at it, it's also the not just someone that is better at the tactical function, but also the like, who are you going to be obsessed being in the trenches with?

41:18Celebrating the highs and being in the trenches on the hard days and lows with. So like figuring out how to build from there. But these are all like little, again, like you've been training for this moment your whole life. Like, okay. And you're still training. A hundred percent. It's not like there's a peak. A hundred percent. Things evolve. It is a constant learning, constant improvement process. You got to start somewhere. You can't ignore the problems and just give it a go one day at a time. And you were at the time also primarily focused on hiring women in leadership positions. Why was that important to you?

41:58I just knew firsthand how hard it was to get hired, to get a job, to have someone believe in you. Right. Like not that the people that I worked for prior didn't believe in women, but I had girl, it wasn't just getting a foot in a door. Like I had to put my whole body in the door jam just to like get in. And then I had to prove my worth. And I think the proving part is a really fun part of the climb just to be super clear. Um, but I loved the idea of a one. I know how smart and brilliant humans are. I definitely know how smart and brilliant women are. I know how tough they are. I know how driven they are.

42:35And I thought, well, this is a secret that maybe other people don't know yet. And I'm going to leverage it to my freaking advantage. And we have like a superstar team. I have like goosebumps on my arms thinking about it. I mean, as you're saying this, this is more than 10 years ago. Yeah. I'll start to tear up right now for you. This was not part of the conversation when you were giving women the leadership platform. It wasn't because of social pressure. It was because it was a personal experience of your own identity and finding your own space and rooms where you belonged. Yes. And recognizing that there are unique and special women that deserve the space and you gave it to them.

43:19I'm also very grateful. Like as much as I found my people, like as much as you find your people and that's your responsibility, your people will also find you. I wanted to talk to you about scaling because we all know that scaling is a creativity killer, especially in your business where you are so focused on a single serving, one item. And when you think about mass production and losing quality, I mean, is that something that you lost sleep over? I lose sleep over every single day. To this day. I mean, I lost sleep over it though, even on day one, right? Of like, am I gonna trust somebody else to mix the compost cookie today?

44:08And the answer had to be yes, because I couldn't do everything myself. Part of it is this sort of like the dimension and the tension of needing to ask for help and train and trust. You gotta choose your partners really, really carefully. But you are right. Scale is infamously known as a creativity killer. And so I would dare say we spend half, if not the majority of our time going, how do we put our blind? Also just today, being a human in the world, there's so much distraction. There's so much this and that, and look over here, how do we put our blinders on and how do we stay creative and uniquely who we are in a world where scale is a pressure point, where cost of living, making money, being able to be the place that you want to work and support and spend your time is a thing and where innovation and creativity and copycats, like it's just a cacophony of worry and hardship.

45:07How do we put on our blinders and show up as we are, who we are in this brilliant universe that we've created? and I do not have any of the answers, but I have some things that have worked for us that we're going to keep doing and I have some things that haven't worked for us that we're going to stop doing and we have some really great ideas about what we're going to start doing and I think this is bringing anything to life or being like, I'm going to be bold enough to say the thing out loud and go out and get it even though the odds are not in my favor. And with that, occasionally comes failure and I feel like I'm sitting across someone that has a healthy relationship with failure and failing forward and acknowledging that in your profession.

45:50Is there an example that you can share with us where in the moment you're like, I lost. We talk about this all the time, right? Like if you're not taking risks, you're not failing. And if you're not failing, you have no opportunity to win. You have no opportunity to win if you haven't put yourself out there. um okay favorite failure that doesn't sound so many well one that i thought like one that i was like super duper duper convicted i don't think we had raised any money i don't think we had anything we were just bootstrapping it from the proceeds from our next blah blah blah and i had this incredibly um courageous insightful passionate team and i was like okay guys i've got it figured it out.

46:41We, this was in the time where green juice had just started taking off where like cycling or like, like soul cycle cycling, like, right. We all live in New York city, like this sort of like the very beginning of this, like healthy lifestyle and being a little bit more attuned and aware to it. And what I would find in our offices and in myself regularly is we're crushing like, you know, we're crushing, um, a milk bar pie and we're crushing all these new dessert formats for the upcoming winter holiday. And then for like midday breakfast, and then we would go out and like crush a green juice and then be like, okay, tomorrow I'm going to whatever, go and sweat my face off at, at this course.

47:29And I was like, you know, you want to know what? It's crazy that we would see it in our customers. They would go and get their local juice or their salad and then come in and get their dessert, right? They're all forms of self-care. People don't realize dessert is a form of self-care. It very much is. Oh, you're not talking to the right person. We're going to look out this way, right? And I was like, well, this is crazy. Someone shouldn't have to go to two places to get the delicious things that they want to put in their body, even though they feel like yin and yang. So I was like, we're going to launch a whole new line.

47:59it's going to be called milk bar life and we're going to have like these really great like yogurt parfaits like they're going to be as obsessively delicious as the dessert you know and love but we're going to have things that you want to put in your body for breakfast if it's not cereal milk and a cornflake chocolate chip marshmallow cookie which is a breakfast of champions um we're going to have like three different green juices but instead of being called like super greens we're going to call it like high kick we're going to call the really green one hurt so good. Like we're going to make things funny to keep, you know, when you drink a green juice, like plugging your nose sort of thing.

48:33And I was like, such a big believer in it. We're going to have coffee and it's going to, our, our line of coffee is going to be called milk bar buzz because obviously you drink coffee because you're trying to like get up to like some sort of like, I'm awake. I'm awake. Let's go. And I was so convicted. I saw it. I believed in it in myself. I saw it in my team. We designed. We went. We launched this whole thing. And it went fine. Like it was middling at best. And Christina doesn't do fine. I don't do fine. I don't do middling. That's just, neither does Maria. I'm looking at the spark in your eye because you know.

49:10You're like, I'm going to take off sprinting right now. When you said content. When you said when you're just content and everything's okay. Not up and down. I don't mean because we can't find happiness. I mean like content and just middling. Yeah, no, I know what you mean. Just like content is not the word you describe. And that's buzzkill. And it was buzzkill. And what we found was that people were like, no, I mean, I think the juices are amazing or the yogurt. I've never had like a yogurt parfait with a passion fruit curd and like, you know, sesame seed and like ground tea, like a Thai tea granola.

49:44But that's not where I want to go to get it. This isn't where I want to go. I want a separation between my where I go for my like joyful time stops, the world pauses. That's my that's where I go for that. And I don't care if I have to walk four blocks or if I go across the street or or. And I use this mentality time and time again because we have some of like some of our stuff is super secret high protein. we have we call them coincidentally gluten-free or coincidentally vegan desserts on the menu that you wouldn't even know unless you actually go digging because what we realize time and time again especially in an era of like bfy better for you right people at least for us when they come in i don't care whether you're a cannonball or not when you come in you are prepared to cannonball into time stand still it's joy for joy at milk bar and even though these other things might be true you don't want to hear about it like that's not this is we are the joy bubble place for it in New York yeah exactly it's not the place for it and it's one of my favorite failures because girl I failed out loud my idea my push my passion failed out loud and you want to know what I am an introvert that was like always raised I have my face gets red when I'm embarrassed because I'm a redhead like there's all the telltale signs and I remember growing up as a kid always being in fear of being embarrassed and there was not a moment of me in that failure that felt embarrassed whatsoever because it's that mentality of like I went out there and I gave it my all and I left it all on the field and I was wrong and we failed and you did it well but that's not where people wanted to eat their healthier snacks they wanted a sweet treat that's it and And it was the like, you don't get, and you move on.

51:37And you go, ooh, we learned something, didn't we?

51:47It's 2023, and you make the decision to step down from your role as CEO at Milk Bar, which is a big, big deal. and you go back to the creative and culinary aspect of the business and you said something really intense um this can't be what life is i'm a shell of a human i mean just saying that out loud is like what were you feeling in that moment were you completely overwhelmed I was not overwhelmed I just felt empty I felt empty in like my tank is empty I had just had my second kid we had navigated this incredible business through COVID I had taken like three weeks off maternity leave for each of my kids not because anyone demanded it other than myself you know what I mean?

52:45And I just remember I had him strapped to my chest. Will was traveling. I'm on like a late night, last minute board call. He's crying into the phone. I'm talking. I've come from a day where I've like stealing from Peter to pay Paul between finance and culinary and operations and innovation. And I just thought I'm serving no one right now. Like I'm giving everyone a percentage of me. And that's not that's just not how I'm built. It's not what I believe in. I'm a cannonballer. I don't piecemeal out things, right? Like if I'm going to give something, I'm going to give it my all. And I had to have and have the energy to give anything.

53:27Yeah. And I was just like, I don't want a life where I don't know my kids or my kids only know what's going on in my life because I would joke about them needing to sign NDAs. You know what I mean? Where I was like, that's funny once it's not funny 10 times and I sat down with myself and was just like what you are gonna have to decide what you really want what is the thing that really brings you the most joy and what is the thing that you are uniquely positioned to do that no one can do better than you I mean this work ethic of like giving it your all is brilliant right like the highs are so high It's every for the longest time.

54:10Milk bar was my everything on every level. I didn't see friends. I mean, I have great friends that I work with. Right. But like I didn't see if you didn't work with me, maybe you can come by the baker and say, I didn't see my family. And I think what I realized after finding my person and starting a family was that there's not a part of me that loves Milk Bar any less. And when I am at work in Milk Bar Christina mode, it's the same, right? But what I also realized when I stopped to take a look at myself in the mirror was like, you are more than this. And don't forget that because the other side of my body was like pushing me to be like, like, stop.

54:59My body was like, I don't want to I would procrastinate to be three minutes late on a call because I'd be like, I just don't want to be on the call. And then you move to Nashville. Yeah, that's get out of here. I mean, talk talk us through that. That's part of like these stepping stones, right? Of I think my husband and I, we always joke that when we are doing our best work, it's because we're both dreamers and we're like dreaming the unreasonable, impossible together. And when we do our worst work, it's because we're both dreamers and there is there's nobody's feet are on the ground. We are up in the sky in a balloon with our dreams.

55:37We make our best and worst decisions together. We both just had moments where he had like his he was changing his professional life and we were both just like there's more to life. There's more in this life for us. And we have no clue what that is and what it looks like. But what we do know it's not doing what we're doing right now. And it's be and it was being unafraid to just to just make like not make a little change, just make a really big change. And he's more of an analyzer. So he was like analyzing it more. And I remember one conversation we were having where he's like, well, what about this?

56:12And what about that? And I was like, oh, babe, I already like my decision was made. Like, I thought we already decided on this long ago. And he was like, yeah, but what about our family and blah, blah, blah. And I was like, the whole reason I love it is because we're taking a chance on our family, on ourselves, on our tiny little family unit that we're building together. And I just that's not even if we fail and we don't like it, that's not a that's not a loss. It's not a failure. It's a data point. And we'll never regret it. What is something that surprised you about the move? Oh my gosh. Coolest part about the move that I didn't think about was when you live in a place that you've lived for so long, you don't realize the dialogue of like should, could, have to, must that goes into your how you make decisions, how you spend time, the people you see, the things you say yes to, et cetera, et cetera.

57:07when you go somewhere brand new where you don't really know anyone, you get to build that from scratch. And when you do it with your person, you get to build it from scratch with your person. So every time we do something, we'll just be brushing our teeth or like drinking coffee the next morning and be like, okay, we do this when we go out to eat at a restaurant. We order like everything on the menu. And then we like the next day or that night, maybe we'll do a debrief of like, okay, what's our like, what's the order when we go back now that we've had everything, when we go back, what is the perfect order for us?

57:37Can you guys film that? Oh my gosh. Between your and Will's sensibility in food. It's my favorite part of dining out is the after when we go, okay, so what is our perfect meal at that place like? And when you, socially, every time we go out, we'll come back and be like, okay, what did you think? Did you like, did we like who we were with? Did you like Joe? Did you like Jack? Yeah. Like, are these our people? Are they our medium people? Are they our like middle of the night people? There's tornadoes in Nashville. Are they the like come to my basement to watch Home Alone on VHS with me and the kids people, right?

58:13Are they the people that we go out with? So you're having an entire new dialogue which didn't exist in the city. You literally get to build one day at a time like what is your dream life? And by the way, like this is the cannibal mentality. Like your analysis is never going to go through these things. These are all of the humanity points and none of the like data points. But I highly recommend moving somewhere new. And when you do, like, really give yourself to it. It makes my brain, it's like adventure. I love that. Your brain, the happy parts of your brain. Full circle. Back to cannonballing.

58:51You're just firing on all synapses. Cannonball. All right. To wrap this up before we get to the pretty tough questions. Okay. I wanted to ask you, because you're an expert, what are the three top desserts that are worth traveling for? Whoa. that's a really good question start okay one okay the cheesecake in san sebastian in spain the basque cheesecake yeah the basque cheesecake dave baran has a restaurant in santa monica in california that has a basque cheesecake on it that i don't even know is on the menu you just have to know to go to the bar and ask for it it's really great look that's one okay two more what other desserts do you like i'm like now like i could go on forever i like the russian honey cake which is the layers and layers of pastry dough with cream in between all these layers it's quite i have a younger sister who's kazaak and a younger brother who is russian and they are obsessed so there is a place in manassas um that is i don't even know that there is specific cuisine but it's right off of um 95 in manassas and they are like an eastern european asian cafe and it looks like if you looked it up on google maps it would look like nothing um and they have the best russian honey cake or honey tea cake that i have ever had and i've had a lot because my sister brings me my younger sister brings me everywhere for it she's she's had me she sends me recipes every time we're gonna see each other um but they have the most delicious russian honey cake that i've ever had and the third one ice cream somewhere in europe is there like one of your god that's a really good question i what about in nashville an ice cream or any dessert in nashville oh god In Nashville, there are so many good desserts.

1:00:53The Yellow Table Cafe, which is in East Nashville, has one of the most delightful chocolate chip cookies. Like it's dry. It's kind of like a creperie. And she came from Park Slope and literally took a risk on herself, made a bet and opened this place in Nashville. and it is beloved and she is the kindest sweetest cannonball soul and she makes a very delicious chocolate chip cookie um we're a big east park donuts family as well where we will just i mean i'm a every donut please person but if it's gelato in europe um i would just say get every flavor we were just in venice a few weeks ago and i literally the best my friends were like you're embarrassing us now because you're holding up the line but yogurt is my favorite do you try all the flavors every one of them it is professional research maria my mother's an accountant that is a tax write-off entirely um but i also i'm a baked goods at home person like i'm a i'm a smiley cookie from the in-store bakery at a grocery store like i think it's really important to go out and support your local bakeries and cafes and dessert um queens and kings and people but also i'm a really big believer in eating dessert at home, like I still think there's nothing better than like chocolate chip cookie dough warmed in like a teacup for like five seconds.

1:02:15You're not making it into a cookie. It's like warm. The chips are melted. Oh, delicious. Cookie dough, making your own ice cream sundaes. What is something that you've had to unlearn? Something that I've had to unlearn that just because I'm an introvert doesn't mean I don't love people and being a human in the world. You and me same. That really resonates. When I'm in like a bad place, I'm like, I'm safe and happy in this corner. And like taking a risk on being a human in the world is always worth it. What is a routine that's helped shape your success? A routine that's helped shape my success is not looking at my calendar, like just going into the day.

1:03:02I don't look at it the day before. Like that has shaped my success because it forces me to be present and really look at the day as an adventure. When I'm in a bad place, I'm trying to control everything and that calendar feels like control. But really the calendar is just like a guidebook to what your adventure is for the day. I'm best and more creative, open, patient in that way. What is a common misconception about you? that I'm like just super loose and free and carefree I am like a type a perfectionist under the surface you really care like it'll I'll wake up in the middle like half of my stories to my team later today will be so in the middle of the night I woke up and this is what I was thinking about this is what I think we should do what is your relationship to perfection what's very unhealthy it's an ongoing battle i think as a baker you have to be a perfectionist because there are parts of it that are so specific the whole scale at mass um but i think of it as a relationship where every day the the human part of me and the perfectionist in me show up and they go how are we going to get this done today are we going to really battle it out are we going to give each other grace who gets to take the front seat who's navigating and i think the unhealthy perfectionist relationship part is part of me.

1:04:24Like I don't, I don't want to deny it or disregard it. Being able to say like, I don't, I didn't need to eat dessert at midnight last night, Maria. One could say that's unhealthy, but part of me is also like, and that's also part of you. So like, you just got to embrace it and move on. I needed it for the soul. What makes you feel tough? going for a sweat like lifting weight i'm a i was a long distance runner for the longest time and then like tore a hamstring got a like heel spur and so i don't run as much but anything physical that is mind over matter where my brain has to go to a different place where i have to my brain has to go like, you will get through this.

1:05:09And I find that in physical activity the most. It makes me feel tough. Like it doesn't even matter how long it is, how much the way it is. It doesn't like nobody else's measure is important to me. It is the way it makes me feel that I love. When you're overcoming your own personal limit. Because I disappear. Like there's always the voice that goes, oh, this is hard. Oh, I want to quit. Ooh, this is heavy. Ooh, this doesn't feel good. And when my brain tells that part, that voice to like go away and be quiet and like you can come back later, but just not right now. And then when it comes back, it's like, that was great.

1:05:49I got it. That was great. Yeah, that's great. We feel great, don't we? And what makes you feel pretty? A waking up after a great night's sleep. Waking up after a bad night's sleep with like a really great cup of coffee. Waking up just the feeling after a really great sweat or accomplishing something that somewhere along the way I told myself was going to be hard, maybe even impossible, maybe even like I want to quit. I feel the best most radiant version of myself when I've kind of I guess when I've overcome myself that and a really great night's sleep as you said sleep I was just thinking of myself a week ago I went on this like very quick trip with my girlfriend and it was the first time that I've done that in a long time where I'm not packing like toddler snacks and or a business casual I got undies and a pair of socks I need nothing else and I woke up like an hour later than I usually do.

1:06:45And I looked at my clock. I was like, this is fantastic. I could easily get used to this. This is not the norm, but boy, do I feel and look pretty. I'm with you, girl. Well, you look amazing. So Christina, thank you so much. I love your wisdom. I love your attitude. You have such a bright attitude and it shines through so much of what you do. So thank you I would say that you have been modeling for me and I would venture to assume so many that like being tough, redefining what's possible, the odds, like you have modeled it for me for many, many, many years before even Milk Bar. So thank you for just being a human in the world and putting yourself out there.

1:07:30I can't wait to hear more stories. That is very kind. Thank you, Christina.

From the publisher

Maria Sharapova sits down with Milk Bar founder, chef, and entrepreneur Christina Tosi. From getting her start writing food safety plans for David Chang to breaking the internet with Compost Cookies and cereal milk soft serve, Christina shares the raw, unfiltered reality of building a massive dessert empire.

They dive deep into the power of her "cannonball" mindset, embracing failure out loud, navigating extreme burnout, the pressures of being a CEO and why she ultimately decided to step back and move to Nashville to reset. 

Whether you're an entrepreneur, a creator, or just trying to figure out your next chapter, this conversation is packed with wisdom, humility, and inspiration.

SUBSCRIBE►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1

LISTEN:►Listen to every episode on your favorite podcast platform⁠:  https://pod.link/1893437254

CHAPTERS

00:00 — Introduction: The "Cannonball" Personality and Welcoming Christina Tosi

00:54 — Trading Business Stories: Maria Sharapova and Christina Tosi on Bootstrapping

04:46 — The Cannonball Mindset: Jumping In Without Knowing the Details

07:33 — Entering the Food Scene: Working with David Chang at Momofuku

09:59 — Finding Your "Why": Transitioning from Fine Dining to Heartfelt Baking

12:20 — The Power of Bad Bosses, Self-Worth, and Playing the Long Game

14:02 — It’s a Marathon, Not a Sprint: Shared Lessons from Sports and Business

17:42 — The Birth of Milk Bar: Opening Next Door to Momofuku

21:55 — Midnight Crowds, Late-Night Culture, and Anonymity in New York

24:32 — Turning Passion Into Business: Finding Pockets of Joy and Just Starting

28:31 — Culinary Training, Cereal Milk, and Protecting Childhood Nostalgia

31:13 — Mental Grit, Doubts, and Trusting the Process

35:05 — Mastering the Business Side: One Day at a Time and Trick Yourself to Win

39:35 — Empowering Women in Leadership: Proving Your Worth

41:35 — The Dangers of Scale: Protecting Creativity from Corporate Pressure

44:00 — Failing Out Loud: The Story Behind the Failed Milk Bar Life Juice Launch

49:33 — Stepping Down as CEO: Burnout, Motherhood, and Empty Tanks

53:02 — Moving to Nashville: Trading Old Rules for a Blank Canvas

56:32 — Rapid Fire: Top Global Desserts Worth Traveling For

01:00:07 — Final Insights: Unlearning Introversion, Perfectionism, and Feeling "Pretty Tough"

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About Pretty Tough

Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term.

About Maria Sharapova

Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship. 

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