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Pull up a seat at our table, where badass women from all walks of life—fashion, beauty, design, music, philanthropy, art, and more—come together to share honest stories, serve truths, and dig into the realities of modern womanhood.
Johanna Almstea...: Hi everyone. I am menu planning for my next guest and I'm really excited because I feel like she really understands the power and magic of food and bringing people together over food. So I'm super excited to prepare a meal for her. It's chilly here where I am, so I'm going to start with some warm appetizers, some kind of old school, warm, yummy hors d'oeuvres. I'm going to do some stuffed mushrooms with breadcrumbs and herbs and some really nice Reggiano cheese in there. I'm going to do a little bit of smoked trout with creme fresh on little blinis, just sort of like bite size pieces that we can have while I'm sort of preparing the rest of the meal. I'm also thinking I might do a little take on like a spanakopita, like a little spinach and feta pastry pie type of thing. And I think with those, she's a big wine person and she knows a lot about wine.
So I might even ask her to advise me, but I'm thinking I might open an old school sort of chablis. These are feeling a little '80s, these hors d'oeuvres for me. So I'm feeling a little '80s. Like a nice full chablis to have with these while we're cooking. And then for dinner, I'm going to make a beautiful crispy sea bass. The citrus is so beautiful this time of year, so I'm going to do that over a fennel and grapefruit and pistachio salad. A good friend of mine makes this gorgeous salad for her Christmas meal actually. So I'm doing a take on that with the champagne vinegarette and then a side of toasty roasted fero with a little bit of roasted veggies cut up inside that fero. So I think that's going to be a nice, warm, cozy, but also bright meal. With that, I feel like we might want a red, even though it's fish. We could stick with the chablis, but we might also want some sort of like pinot noir, a little chilled pinot noir with my fish.
So I might ask her for some recommendations of that. I do always often go back to the sea smoked pinot noir that I love so much, but maybe we'll do like a little French pinot noir. Anyway, that's what I'm thinking. And for music, I've kind of been digging these like old school lady crooners, kind of like these women who were so badass back in the day, making such incredible music. I've been very into Minnie Riperton, Betty Swan. So I'm going to have some of these badass ladies singing in the background. I might mix that in with a couple dudes, maybe a little Leon Bridges to bring it into current time. But she is a powerhouse and a delight. And I know we both kind of go hard all the time, and so I think it would be nice to sort of make the night mellow and calm and cozy and share a meal and share what I know is going to be an amazing conversation.
So this woman is going to knock your socks off. She is bold. She is intelligent. She is energetic as I'll get out. And I know that she is going to inspire you and ignite something in you and I cannot wait for you to meet her. So let's dig in. Hello everyone and welcome to Eat My Words. I am really thrilled to have someone on today who, as you will see, clearly contains multitudes. She is the Chief Executive Officer of Empower Aesthetics, a portfolio company of Shore Capital Partners, where she has also served on the board of directors since its inception. She's also the former CEO of Surgical Solutions. She's been a lecturer and management at Stanford University's Graduate School of Business and has served as an adjunct professor of entrepreneurship at the University of Chicago's Booth Business School. She's a slacker, clearly.
From 2005 to 2015, she was the founder and CEO of Bottle Notes Inc., an interactive media company recognized as a leader in the US wine, craft, beer, and artisanal spirits industries. She is also a wife, a mother, a daughter, a sister, a horse mom, a tennis mom, an avid sportswoman, a former competitive gymnast, a Midwesterner, and a friend, some of which she speaks about in the book that she is a bestselling author of. So Alyssa Rapp, welcome to Eat My Words.
Alyssa Rapp: That was about the nicest intro I've ever had. Let's record that for the ages. Thank you so much. It's a pleasure to be here.
Johanna Almstea...: You can just put it on a little megaphone and drive around your town and just make sure everyone knows.
Alyssa Rapp: Trust me, that'd be good for my ego and my soul, but thank you, thank you, thank you.
Johanna Almstea...: Thank you for being here and for taking time out of what I know is a very busy and full life at a very busy and full time of year. So I really appreciate you joining me. I always like to tell our listeners how we know each other, and I think this is sort of funny because we were introduced by a longtime childhood friend of mine, Andrew Margolic, shout out to you, who always joked with me that I'm super intense. He's always like, "God, you're so intense. You're so type A." You're so this, you're so that. And so a couple months ago he texts me out of the blue and he's like, "You need to meet my friend Alyssa. She's a total badass and she's crazy smart and kind and you'll love her." And after I got to meet you and talk with you, I texted him back and I was like, "Thank you so much for connecting us. I love her. She's amazing. And she makes me look like a slacker." She's like-
Alyssa Rapp: Now that is not true whatsoever. That's ridiculous. That's ridiculous. What are you saying? But Andrew's a great baseball buddy of my husband's for a long, long time. And when he says you have to meet someone, I usually say yes. And in this case, it exceeded all expectations. So thank you to Andrew Margolic too.
Johanna Almstea...: Thank you, Andrew. He'll feel good. He needs the shout-out. He deserves it. And then I read your book and it made me so happy and it made me admire you even more because you really talk about so many of the things that matter to me and that I've tried to live by throughout my career and my life.
Alyssa Rapp: I'm so glad.
Johanna Almstea...: Which we'll talk about a little bit of that more later, but it really resonated with me on many levels. So let's get into it. I always like to start with the question of where did your journey begin? Because it's always fascinating to me to hear what people say. So where did your journey begin, Alyssa Rapp?
Alyssa Rapp: I think that's a super hard and super easy question all at once. And thank you again for having me on Eat My Words. I'm impressed by what you're doing here and it's a privilege to be on. And thank you for reading the book. I think my journey began as a kid who was, my husband and I talk a lot about this vis-a-vis our two girls that you identified as the tennis and horse girls. But I think going back, it started as a young kid who was an athlete. I started in ice skating and then moved to competitive gymnastics as you articulated and eventually ended up in quite serious classical dance, modern and contemporary dance.
And I think as someone who was academically minded and focused with a major piece of her life driven by athletics as well, I was driven to pursue excellence and I was driven to be the best version of me I could be and had the great privilege of a mom who wanted to help make that happen through her hard work and support, and growing up in a community here in the northern suburbs of Chicago where education and athletic talent and artistic talent were all valued and had the privilege of great role modeling and an entrepreneurial stepfather and an entrepreneurial Holocaust surviving grandfather to go after it. So the journey starts young for all of us, and for me it started as that same quilt of life with a lot of drive and a lot of opportunity. But I think what I learned then is the same thing I know now at 47, which is hard work doesn't guarantee success, but it seems to be the inherent ingredient required for all of it, and the good, bad and the ugly. So I guess that's where it started.
Johanna Almstea...: Yeah. And was the sort of drive and the academic drive and the competitive drive, was that innate in you or was that something that your family sort of put upon you?
Alyssa Rapp: My husband, who was a World Series champion baseball player, and I have this conversation very often. I think drive is a tremendous amount nature, not just nurture. I think you are born with the desire to fight and to work hard and that can be cultivated and then opportunity can be put in front of you and you leverage it, but I don't know if you can teach someone the killer instinct of wanting to fight and win. I don't know if that can be taught. And I don't know, I think you can shape it around the edges, right? Your God given talents or your God given talents work hard and expectations are set forth by your role models, but whether or not you're satisfied being 92% of the way someplace or only at 98% I think is incredibly intrinsic.
I'd love to think that it can all be taught and a lot of it can, but grit, I think grit can be role modeled, but a lot of what the drive that I feel in me and I see in others that I mentor, married, what have you, a lot of it's intrinsic I think. The extrinsic motivation can be a powerful motivator. I think the greatest driver is intrinsic.
Johanna Almstea...: Yeah.
Alyssa Rapp: Do you agree? I guess is the question.
Johanna Almstea...: I do. And I think it's funny because I feel like there are some people I know who had parents who were super-duper intense and expected a lot. I mean, my parents were pretty intense too, so I don't know. And then I always wonder, would they have been as successful if they hadn't had that? And then I know there's people who don't have that and it's fully nature, not nurture. It's fully just who they are. And I think mine's probably a combination. No, I think mine's probably nature too. I think it's a combination of both, but I think there was a lot of pressure in my house to do well academically and to be a good person. Those were the big parts for us.
Alyssa Rapp: Yes. And I should caveat by saying, I think that living in a values-based home, and in my case now today, leading values-based organizations, those are choices that are cultivated and values that are cultivated. And that is 100% whom you're influenced by, our parents and role models and mentors. And that piece of influence is extraordinarily consequential, if not determinant. I'm really talking about the separate piece of it is within those frameworks, right? You could have someone incredibly driven without incredible opportunity and then the ceiling is different. It would be naive and unfair to suggest otherwise. Then there can be folks with endless opportunity without the inner drive and then you're only going to go so far. And then of course the cross tabulation of talent, opportunity and drive is where hopefully is necessary not sufficient for success. But ultimately what I have been reminded of time and time again is that extremely hard work is necessary, not sufficient for anything that's worthwhile.
Johanna Almstea...: It's so true.
Alyssa Rapp: Yeah.
Johanna Almstea...: So true. Doesn't come easy.
Alyssa Rapp: There is just no free lunch, not ever. Not that I've found. If you find one, tell me about it.
Johanna Almstea...: No, I have not found one either. I'm still working on that. So as a kid growing up outside of Chicago, did you have a picture in your mind of what grownup success looked like or what having it all would mean? And so it's very part of-
Alyssa Rapp: Absolutely not. Absolutely not.
Johanna Almstea...: No?
Alyssa Rapp: No, it's ironic. I had an incredibly talented mother who was a lawyer and a single mom for a period of time in the 80s when that wasn't really done in Winnetka, Illinois of all places. And then she and my stepfather were together. He passed this year, sadly, but they were together for three fourths of my life. And so he was this incredible role model of real estate development and entrepreneurship here in Chicago, Daniel Levin. And so I had the version of success that I lived by being their daughter of... He was a risk-taker, she was an attorney. Her career evolved over time into crisis management PR and then a great deal of public policy work. She ended up a US ambassador to the Netherlands under Obama and my stepfather was always incredibly civically engaged, philanthropically engaged in addition to his real estate and managerial life. And so to me, that was grown up success, right?
Johanna Almstea...: Yeah, I'd say so.
Alyssa Rapp: It was being actively involved in running organizations and being politically engaged, being civically engaged, being engaged in the arts. So in that sense, yes, I had incredible role modeling of what being a grownup is. My knee-jerk of no, if you had told me as a teenager, a young teenager, that I would have ended up at an Ivy League school and then working in politics for the national finance director for a US Congresswoman, and then at Stanford Business School as an aspiring entrepreneur, and then a dot com CEO in the wine space, if you had told me that much, let alone then a pivot to healthcare and private equity back, CEO life or raising a fund on the NASDAQ and Healthwell or back to PE CEO life again in healthcare, if you had told me that were the journey, I would have looked at you cross-eyed.
There was no piece of me truly that had any of those expectations or outcomes in mind. I was an academic, I was an athlete, I loved being a choreographer of modern dance and danced about 30 hours a week at Yale and Yale dancers and met some of my greatest girlfriends from college there and thought about maybe dancing professionally, not surprisingly glad I didn't, that's a hard life. I wrote essays going to college and grad school about being the first female president because there'll be one before my time would have been up, but those are traditional childhood dreams. I think what I realized then that is still true now is I'm a builder. I like to build things. I like to create things. That's why I ended up a dot com entrepreneur and that's why I'm running a growth equity based company right now.
I believe firmly in giving back to whom much is given, much is expected. I spend a tremendous amount of time, whether it's on nonprofit boards or currently as a elected school board member, which is my civic life of giving back. I believe in the old Buddhist saying, the best way to learn is to teach, which is why I taught at Stanford Business School for seven years when we were living out there and now moved back to Chicago. I'm at the University of Chicago Booth Business School. And I choose to do these things because they both give unto others and they give to myself. And then of course, the most challenging, truly, and most important job of all is being a mom and a wife. And that's not because it's a cliche thing to say.
It's because it's the most challenging and probably the most important thing I'm doing besides all the people for whom I'm responsible in my CEO life, and the students whose academic progress and entrepreneurial pursuits I take seriously as a professor of entrepreneurship at Booth. So I don't think I could have given you a paint by numbers portrait of how my life would have turned out, but I definitely am grateful for the twists and turns on the journey.
Johanna Almstea...: Yeah. You talk a lot in your book about having these incredible role models in your grandfather and your stepfather and your mom. And I love that you said at one point, I just knew that I could start a business because that's what people did. In my family, people started a business and ran a business and did it and that felt normal to me. And that really struck me because I feel like there are so many entrepreneurs who are... We have a lot of entrepreneurs in our audience and they don't have a role model. They don't have someone who has lived experienced being a founder and what running their own business means and stuff. So I thought that was sort of beautiful and so valuable and I'm sure such a major step in this country.
Alyssa Rapp: And shows you the power of role modeling and how important it is, mentorship. Be one, get one is probably my most discussed chapter in the book that you mentioned, Leadership and Life Hacks, right? To whom much is given, much is expected, but being a mentor, being mentored is crucial. I lost a very important mentor in the last month, Joel Peterson.
Johanna Almstea...: Oh, I'm sorry.
Alyssa Rapp: My favorite professor from business school. Thank you. It's been a tough year for loss, but he was incredibly important to me on many levels academically, professionally, incredible values led person, died unexpectedly at 78. And what I realized in his passing, and I thankfully communicated much of it to him, but mentors and sponsors are people who believe in you and signal to the world that their belief in you is something that should be taken seriously. And I try to do that for people I care about a lot. I've done it for students of mine like he did for me. I've done it for other entrepreneurs. I do it for people with whom I work, but you really realize that paying it forward is pretty crucial because to your point, the role modeling is incredibly powerful. If you can see it, you can be it to quote Gina Davis and I really do believe that women particularly need more role models.
And part of that means holding up the extraordinary talents of our generation, those who've made hundreds of millions, if not billions of dollars. It also means holding up the people who've had moderate success and are fighting and going for singles and doubles and triples every day and realizing that nothing changes if nothing changes and just having the courage to quote Brene Brown to enter the arena as part of the battle. And that's why I have my kids do sports because besides the obvious stat that like 90% of all female CEOs have been athletes as kids, I think that having the courage to be in the arena is what matters most.
Johanna Almstea...: Totally, totally. Okay. So you brought up your kids, your beautiful daughters, you have two girls. One thing that I really loved about your book was, and this felt new to me, maybe I didn't ever think to look for books like this because I probably just assumed they didn't exist when I was having kids and becoming a mother, but your book is literally like equal parts true business strategy and equal parts mother strategy, mother and life strategy.
Alyssa Rapp: And by the way, when I go to corporate... When the book first came out, I did a whole bunch of book tour stuff and corporate talks over it to women executives and firms that wanted to talk about Leadership and Life Hacks since I was a mom, wife, entrepreneur and executive. I am going to tell you that 95% of the time, I could be at McKinsey or I could be at Utz, I could be at any company, 90% of the time you walk in the room, the women want to talk about the life stuff.
Johanna Almstea...: I'm sure.
Alyssa Rapp: What's your hack for that? How do you do X? And it's quite amazing. It's actually remarkable because to me the strategic stuff is much harder, but the life stuff is the lifting of the lid of how it all works and the guts of it. It's interesting because it's hard. Managing all the spinning plates is hard.
Johanna Almstea...: Well, and I feel like they're usually siloed, at least in my experience. It's like either there's like the lean-ins of the world or there's like mom blogs, but there's not a lot that's like combining the two. And I think it's doing women a disservice if you're not combining the two, right? Because those do not live in separate places, which I have found out and you have found out on your journey of motherhood. It's like you can't separate them. They are so intertwined and you need to know both and you can't really do one well without the other, right? And so I think that that was sort of extraordinary because I don't know what your experience was like when you had your children, but when I had my children, it was like I had to pretend like I didn't have children.
Alyssa Rapp: Yeah. And I think that's the piece that's changed. And I think one of the rare blessings of COVID was that it sort of lifted the lid on all that too, besides kids popping into Zooms, which was obvious. But this idea of layering, everyone's like, multitasking is bad. I think that's absolute bologna sandwiches. I think layering is required. My kids have probably got an MBA in the calls they've heard driving to tennis or equestrian practices from the conversations I've had to have. Now it doesn't mean I don't want to spend quality time with them in the car. I try to only have calls one way so I can talk to them the other way, but sometimes there's no other way. If I want to be there to support them, I have to layer in some work over it. It's just the nature of the beast and it is what it is.
Johanna Almstea...: It is what it is.
Alyssa Rapp: The world has changed in fairness over the last 30 years since I was a teenager and there's no question people have become more aware, let alone accepting in many environments, but it's also... I mean, I have 6:30 AM calls almost every Monday with my private equity sponsor and that is also what it is. Being in the arena means working your tail off and being available lots of times, which means that those days I get up and make my kids breakfast and then I like punch out to take a call and I punch back in to see them and make sure their homework's on track and they're getting ready for school and all that, that's the world we live in today. So the intertwining is an opportunity because it allows flexibility in a way that I don't think was always available for.
The downside of it is for men and women, this is not just a gendered comment, it is much harder to turn off, right? I think that the expectation of being on is high. I set it up myself and what's tricky about that is then there's greater risk of burnout if you don't ever find times to turn it all the way off. I did turn it all the way off yesterday because I had a kid thing in Toledo, tennis tournament in Toledo, other kid was in an equestrian tournament in a different part of Ohio with my husband and there was a lot of kids sports stuff to manage. There was a long drive, all the things. And that was a bunch of time away from email. My inbox this morning was a disaster. It wasn't great and it was Monday at six.
So that piece of the pace of change I think has advantage and disadvantage. But to your point before, the layering and intertwining of work and home life I'd like to think has advantage for women because it means that you can be both more authentic and probably more flexible, even if it means you're probably "on duty" in both aspects of your life a tremendous amount.
Johanna Almstea...: Yeah. I also do think it gives our kids the opportunity to see us actually working. I feel like when my kids were really little and I still had a big corporate job, I would try very hard to be with them, dedicated to them and then get them to bath and bed and dinner and whatever, and then get back on my computer after bedtime and they never really saw it. They didn't really know, right? It was like out of sight, out of mind. Now with this sort of more flexible way of working, I do actually feel like they know now that we work, like they know what that is. And like you said, those calls that they listen to on the way to the equestrian center or the tennis lessons or whatever, it's like they're learning, they're seeing.
Alyssa Rapp: I mean, as someone who teaches at some of the best business schools in the country, I'm really going to start to question if I should pay for an MBA for these kids because they have had one. I'm just going to tell you right now, they have had one.
Johanna Almstea...: Osmosis.
Alyssa Rapp: Like it or leave it. Osmosis, baby. No degree associated with it, but osmosis. Yeah.
Johanna Almstea...: So when they're old enough to listen to this podcast, because we do curse on this podcast sometimes, so maybe they're not allowed-
Alyssa Rapp: Their father was a professional athlete. There's a lot of cursing. We've learned there are words adults say and kids don't say. Yeah.
Johanna Almstea...: What do you want your girls to know about this time though? This time when you've made a few career changes since they were born, you've chosen different paths, you've chosen different types of working where you are now, taking those calls in the car. What do you want them to know about you, about them, and about your relationship to them as a mother during this time of their life?
Alyssa Rapp: That's one of the best questions I've ever been asked. No wonder you have a wildly successful podcast. I have not been asked that before and it's a really good question and it's a hard one. I think this is the panini press of life. I mean, I really mean that. I've had dying parents, aging parents, in-laws and my own. I've had kids who are growing and thriving and challenges they face and you have to juggle all of that while also managing yourself, your marriage, your health and all the things. I do really think it's the panini press of life. And I think Ray Dalio describes it as such as well, even from the perspective of a gentleman. So in that sense, I hope they look back with some grace when patience was thinner than it should have been or when time was scarcer than I would have liked it to be.
I also hope they look back and they have gratitude, which was, wow, she really did everything she possibly could with the time she had available to do what she could to give us every opportunity in the world and then some. I think that that would be what I hope they look back on. And I hope they look back and see that passion and purpose is the point. And having impact is not just measured by economic outcome, but it's a piece of it. And listen, they're going to have a lot of privilege. I mean this like differently. Not to say that growing up in a wonderful North Shore community with a wonderful education and wonderful family isn't the definition of privilege, in many ways it is, but that will be a different level, and I talk about this a lot, like even than we had.
And so how do you think about that? How do you define success? And what our success looked like and what it will look like for them will probably be different in some ways. And yet, how do you think about the conversations you had, the values you were describing earlier in terms of what your family taught you about integrity and work ethic and caring for the world? I think that it's just different. It's different because their circumstances will be different. And yet I hope that the values that we put forth on drive and commitment and care and consistency and all of that stuff and the same values my parents showed me of giving back, giving of yourself meaningfully to others, to your career, to your colleagues, to your family and being a values led person, that's the part that I hope they try to emulate. Their application of it in their own lives will be their own choices. And I hope they use the privilege to leave a great impact on the world, whatever that means. And that's hard.
Johanna Almstea...: Yeah. It's super hard. Okay. I have to ask because clearly you have two very competitive people as parents, your children do. How does that manifest itself in their own sports and stuff? Because I have so many thoughts about youth sports. And having a professional baseball player as a father and having a former competitive, all the things, gymnasts, dancer, all of these amazing things that you've done, how are you as a sports parent? I need to know.
Alyssa Rapp: So it's a really good question. Someone described to me once having children is like having a piece of your heart living outside of your body.
Johanna Almstea...: 100%.
Alyssa Rapp: So when one kid was jumping around on the horse and I had my own PTSD from gymnastics and some battle orthopedic injuries, I mean, there's a piece of me that can barely watch and hides behind, not because... I have total confidence in her and I have admiration for her and her courage and her strength and all the things, but it is hard to watch a piece of your heart jumping around out there and hoping and praying for the best and not the worst. That's more like high cortisol spikes. It is hard for me to watch, big exhale when it's over and she's safe. And then the tennis, it's longer, it's more sustained, it's less life and death risk, but really highly physically demanding, but also mentally really demanding.
Johanna Almstea...: Mentally, yeah, emotionally.
Alyssa Rapp: So my concern there as a mother is more on the mental toll of the game and the psychological warfare than the physical, although the physical, she played for seven hours straight two days in a row and she was pretty beat up yesterday night when we were driving home. But I mean, ultimately I have extremely high expectations and also have the acute awareness that they're being given every opportunity to succeed. So I have no guilt about the opportunity. I have high expectations they both are dedicated and leave it all on the field. And I think by and large they do. Where my husband's experience is both incredibly best in class in the whole world, being best in something like he was in Major League Baseball, winning the World Series and all that and challenging is he knows and I know and he knows better than anyone too, leaving it all in the field is enough.
I mean, it is necessary and our kids work very hard in the lessons, but being the best in the world at something means you don't just put in the work and the practice, but you have a degree of loving obsession with it where you want to be a student in the game off the field, where you want to study the strategy, you don't just need to put work into the technique, but you also want to think about constructing points, the mental skills aspect of the game, even additional agility or other types of cross-training benefit you can have. And so in that sense, we have the blessing and the curse of really knowing what it takes to be the best in the world at something. And that perspective is exacting because our kids are bright and talented and fortunate. And yet if you want to be the best in the world at something, that is definitely not enough per our earlier conversation.
You have to want it badly or more badly than everyone else. And that's the piece where I think we've both struggled at times and that we are people who want it badly and always work our absolute tails off. And they both work hard. Please don't misunderstand me. But 90% effort in this day and age is not enough to be the best at something. You have to want it more than the next person and we can't want it for them and that's hard. That's what's been hard.
Johanna Almstea...: I was just going to say, do you want them to be the best? You want them to be-
Alyssa Rapp: I want them to want it for themselves. And then it's not even about the outcome for me. It never has been. It's about there is great peace knowing when you've left it all in the field. I've had wins in my entrepreneurial career and I've had losses, but when you sleep well at night, the wins are fun for sure and they feel really good. But the losses, you can still sleep well at night knowing if you literally gave it your all. If you gave your 150% and the cards didn't stack your away, the regulatory dynamics [inaudible 00:28:35] changed mid-game for me, got a deal done, it should have gotten done, we cleared the SEC and the seller decided they didn't want to consummate the transaction. That was imperfect and unexpected and disappointing and stunk. That was an L and I hated it. And yet I honest to God can tell you I did everything I could do for the W and it stinks, but you have peace knowing you left it all in the field.
I would have liked to win a whole lot more, but I've made my peace with it because there was nothing I could look back and say I didn't do that I did. And that's what I think we both want for our kids, but you and I both know you live life forward, not in reverse. And so you can't look back and say, you're going to regret this if you give it 99%. That is not how life experience is gained. You can't tell someone, sometimes they have to just live it. So that's been the hardest if you want the honest truth.
Johanna Almstea...: Yeah. No, I imagine it is. I mean, I'm definitely not as... Although my friend said that I am competitive. I don't think of myself as a competitive person. I think of myself as like-
Alyssa Rapp: Driven. You're driven.
Johanna Almstea...: I'm driven and I like the best of things, so I don't necessarily need to be better than anyone else. I just like it to be right. Anyway, as a sports parent, it's interesting to me because it's been my brother too, we talk about this all the time is like, how much do you push and how much do you let them just do their journey? It's their journey and it's not yours anymore, right? Does it matter if they're good? Does it matter if they're the best? Does it matter if they suck? I don't know. I just think about it a lot. So I was wondering-
Alyssa Rapp: Very, very challenging. And Apollo Ohno, I don't have the dates exactly correct in my mind, but I recall there was a period of time when his father was coaching him and it was before one of the Olympics and he just felt like his son, who's now one of the greatest speed skaters of all time, was sort of half-assing it for lack of a better phrase. And as the lore goes, he kind of said to him, "You've got to decide here, son. You're either all in on this and then you're giving it 110% or we are wasting our time because all the talent in the world, everyone else who doesn't have half your talent's giving 120%. So you either need to go for it or not go for it."
And as the story goes, Apollo Ohno went for it and I don't have all the lore in my head with great detail, but I think that that's... We live in an incredibly competitive world with more and more specialization as youth sports go, to your question from before. That's not going to change. I'm not going to change that and you're not going to change that. The stakes get raised therefore for all sports for children if everyone who's at the best of the best is practicing four or five hours a day and it's not... When I was training for gymnastics in the '80s and '90s, it was three hours a day, six days a week, and that was like the most anybody trained for anything. It was 6:00 to 9:00 at night, Monday through Friday with one weekend day for four hours, and it was intense.
And I wasn't even on the Olympic track at that point, which a girlfriend of mine growing up was for rhythmic gymnastics and other things. Then it was six hours a day. Many of our youth sports today, 30 plus years later, are that way where you have to kind of... And I have friends whose kids are on travel hockey and travel soccer and travel baseball. And my best friend from childhood, her son almost made the Little League World Series this summer and they were on the whole run up to it and he was one of the pitchers. I mean, they were on the road for like six weeks.
And I said, if they had not been able to do that professionally, which they were very fortunate they were, it's a lot of time away from work, it's a lot of support needed at home for the other kid. This is not-
Johanna Almstea...: It's no joke.
Alyssa Rapp: This is very serious competitive levels and it requires a lot of infrastructure and a lot of financial infrastructure and familial infrastructure. And I think that that has changed. And so to your point, no, we are not comfortable with mediocrity. It's not who we are and that is a big piece of us, and I think that creates a lot of environmental pressure for our kids without us saying anything to them. But the piece that we struggle with as parents, I do think I can say this and speak for my husband in saying this, is we both are acutely aware that to go from good to one of the best takes that extra effort. And the hard part is realizing that it has to come from the kid intrinsically versus extrinsically from us.
Johanna Almstea...: Right. It's fascinating.
Alyssa Rapp: Complicated.
Johanna Almstea...: Complicated. Yeah. I mean, because I have moments where I'm like, what is this all for? I mean, are we all going to the Olympics? Come on guys. This is too much. And then there's other times where I'm like, okay, this is what they want to do and this is who they are and they have the drive and we have to support it.
Alyssa Rapp: That's right because what else is it all for, right? To be the best you can be at something. And I have less ego around where you land and the rank order of life in that regard, but I do care that you learn to have a goal and work really hard to achieve it. That piece of the pattern matching I think is good life experience and learning from our loss, being a graceful winner and an elegant loser and learning from why we didn't win and what do we learn from it and continuous improvement. That's to me the life skill besides the dedication and drive and all the things, but it's a lot. It's a lot.
Johanna Almstea...: It's a lot to balance. You talk in your book a lot, speaking of balance, you talk a lot about not seeking daily balance, but episodic balance. I like that term, episodic balance. Because as you are trying to do all these things, you're trying to be the best at your job and your life and your parenting and you want your kids to be doing the best at their job of being kids and being students and being athletes. How do we strike that? I like this term of episodic balance. Maybe there's one day that's off and another day that's good and kind of like having a roundabout-
Alyssa Rapp: I think episodic balance is actually a very intentional concept. And my late mentor, Joel Peterson, I borrowed from him. He had the very famous conversation 20 years ago about juggling glass and rubber balls or the other metaphor is don't drop the glass ones, better [inaudible 00:34:07] know what they are if you don't drop them. His other famous metaphor and it relates to episodic balance is, he said, "If you want to get all the rocks and the pebbles into a glass jar with water, put the big rocks in first, then the small rocks, then the sand, then the water, and you'll optimize the space." And that metaphor as well, it's know what the large rocks are. And so I think with episodic balance, it's this idea of... Like this weekend I was a mom and I was a CEO. My husband was with the other kid. Being a wife wasn't number one in the list and being a lecturer in management didn't get to that piece of my life, right?
And then there'll be days this week where I'm traveling for work for 36 hours and it's like I'm a CEO, part one and part two, and I have to have the infrastructure and the plan in place for the wheels to stay on the bus at home. And there are things that like, I love my spouse, I'm a dedicated daughter, I'm a dedicated sister and dedicated friend. There are times when other things matter more than anything. I was choking with how our anniversary was one of my favorite days of the year and we had a board meeting scheduled for that day and I thought it was actually pretty unusual for a female CEO to tell a private equity firm, no, I can't do the board meeting that day, it's my anniversary. They're like, say what? I'm like, yeah it's my anniversary. No, we go away every year. And they moved it a day for me. So to be clear, that was-
Johanna Almstea...: Oh, that's good.
Alyssa Rapp: It was gracious and I have nothing but gratitude that they did that. But the point being, it's about prioritization and about self-awareness, right? If I lied to myself and I said like I was going to be the world's greatest wife this weekend when I didn't see my spouse, that is not accurate. On the other hand, if balance is to be achieved, I think it's by focusing on really trying to prioritize two stakeholders in a day, like being a great CEO and being a great mom or being a great wife and being a great mom or being a great daughter and being a great CEO and realizing that to achieve balance is something that you have to widen the aperture of time and think about those stakeholders over a two or three week period, did I invest as heavily in all those stakeholder groups as I meant to? But to do it all in one day is impossible.
If I woke up every day at 5:30 in the morning and said I have to be the perfect wife, perfect mom, perfect CEO, perfect lecturer, perfect daughter, all the things, I keel over. It's just not possible to do it all in a day. But if I really try to be focused, it does two things. One, it holds me accountable and honest of how I spend my time. And two, it means that that day never happens again. You have to leave it all in the field. If you're going to be focused on being a present parent, this is it. And present is tricky, right? And these transitions are hard, especially as you get more and more ensconced in your own life. That means not just like staring at the phone, that's my time with my kid is a fail. On the other hand, life sometimes comes up.
Crises don't necessarily pick their timing in any aspect of your life and you just have to kind of drop it all and focus. But the concept of episodic balance is that if you think of life as a series of episodes and you're trying to achieve balance in the episode, but not on a daily basis, being conscientious about who the stakeholders are that you're prioritizing and trying to prioritize them with evenness or relative ranking over a period of time is a more realistic approach and a more satisfying one. And then the final quota to that is it's quality, not quantity, right? A high quality experience, even if there are fewer of them matters most would be the point of that.
I think that's true. I think sometimes the in between times like driving a kid back from a thing or an unexpected conversation when someone calls you and you're finishing a run with someone from work that wasn't scheduled and you end up with a 15-minute one off. I think the challenge with that is I am highly scheduled and it's how I have to be to get in everything, but sometimes the transitions are where the-
Johanna Almstea...: The magic happens.
Alyssa Rapp: The magic happens and making time for that's the hard part. I don't have it all figured out.
Johanna Almstea...: I struggle with that too. I feel like on the days when I'm like, okay, I can get it done. I'm going here, we're doing this, we're doing this. And then I sometimes get through it and like, I kind of missed the in-betweens. I can tell that I missed the in-betweens. Or I'll sort of have the beginning of a conversation with my child or with my producer and then you sort of like move on to the next too quickly.
Alyssa Rapp: Exactly.
Johanna Almstea...: It's hard.
Alyssa Rapp: Exactly. It is. That's well said.
Johanna Almstea...: Okay. So I like to talk about this a lot with women clearly who you've gained a tremendous amount of success in your life. You have had lots of wins. I like to talk about what are the sacrifices that you've made to get this far in your life? What have you sacrificed?
Alyssa Rapp: I mean, listen, I would work out two hours a day if I could. I don't have the time right now. I'm lucky to get in 45 minutes. So I wouldn't say I've sacrificed my health, but my love of working out, it's not about aesthetics, it's about psychology, not physiology. I would run longer, lift more, maybe do more things competitively still if I had more time.
Johanna Almstea...: Okay.
Alyssa Rapp: I also think that we have not had, because of the intensity of work and our kids, we probably haven't had like a proper dinner party socially. We've had work events, but like a proper dinner party in a good six months, which was like, man, I used to have them monthly. It's not that I don't have close friends that I adore. I do, but having as much social life as I would have. Now my husband would prefer to have less, so he's probably very satisfied with where things are. And I adore our children, I realize it's a very finite period of time with our kids and they're growing up and teenagers and all that. So I'm trying to cherish those moments, but there's not enough time to do it all. And I probably would say I've sacrificed social life. I travel a day or two every week for work.
In no world would I consider doing a girl's weekend. It wouldn't even occur to me. If I'm going to have a girls' weekend with my kids, probably at a sporting event, right? I mean, so I'd say is it a sacrifice? No, it's a time constraint. It's not like there aren't women I'd love to spend time with. I just don't have the time.
Johanna Almstea...: Right. I struggle with that. I had a friend who was going away on a yoga retreat like the third week of school, like in September. And I was like, how does that even happen? I don't even understand those kinds of things. She's like, "Me and a couple girlfriends." I'm like, I haven't figured out how to extricate myself from anything like that to be able to do something like that. It was pretty amazing. So yeah, I can understand the girls trip thing is very few and far between for me. But you just alluded to it, and this is actually one of the things I want to talk to you about your book because obviously it rings true to me because I love to talk about food and I feel like communing over food and beverages is a very important part of life. I love that you even had like a chapter or a hack number of breaking bread together as a business strategy. And that's what I even liked.
I feel like so many places that I've worked and so many jobs I've had that this was totally missed, that nobody understood the power of breaking bread together as an actual business strategy, obviously seemingly as a personal one as well. But like talk to me a little bit about that because I've always been surprised when it's not a priority to people and I loved that you put it on paper and said it is.
Alyssa Rapp: I think that there's really no better way to just get to know someone than by having a meal with them. It does a bunch of things. For one, manners are a quick way to assess.
Johanna Almstea...: Manners. Oh my God, don't get me started on manners.
Alyssa Rapp: They matter. Second of all, I think guards are down, mine included, and so it's a nicer way to get to know someone with less pretense. And third of all, if I don't look forward to having a meal with you, then why am I going to want to work with you?
Johanna Almstea...: Good point.
Alyssa Rapp: Because that's supposed to be the easy, fun part, not the hard roll up your sleeves part.
Johanna Almstea...: Yeah.
Alyssa Rapp: And it's not the really silly euphemism of the past, which is, do I want to have a beer with this guy? It's not that. I mean, it could be, do I want to drink with you? It could be, do I want to have a bite to eat with you or a coffee with you? It's just really would I enjoy spending time with you outside of a formal environment? I had a lot of success in my Silicon Valley days of going for runs or hikes or workouts with people. I've done some of that since we moved back to Chicago with my team, but it is really, do I want to spend time with you? And it could be consuming calories, burning them, something, but something that's not on a screen and doesn't involve a phone call, but it's like being in the flesh and it doesn't have to be every day.
It's just those connections as humans I feel are what drive people to say, okay, I'm part of something bigger than myself and I'm going to work extra hard to not just do this for me, but for this team after the fact. And to your point, it builds relationships. So it doesn't always make the difference of people putting in the extra 10%. A lot of that, as we've talked about, is probably intrinsic, but it does matter, right? Not letting people down both ways. I mean, boards across the planet often have board dinners before board meetings specifically to erode barriers and build relationship capital. So this is not an idea unique to me, but the practice of it on a more frequent basis I actually think is really good. And I think that while remote work and hybrid environments which I've managed for the last 20 years are really helpful and easy to do in managing teams, I still think there's no substitute for in-person.
Johanna Almstea...: Yeah. I also think you can learn so much about someone and how they interact around food and beverages and service people and restaurant environments or in your home environment. I just think it's fascinating to me always. You learn so much.
Alyssa Rapp: Agreed.
Johanna Almstea...: You also talked about having snacks in offices, which I also am a huge proponent of.
Alyssa Rapp: Oh yeah.
Johanna Almstea...: And I feel like so many places. I mean, I guess you were in Silicon Valley, so they've gotten that part.
Alyssa Rapp: Totally.
Johanna Almstea...: They've nailed that. I came up through the fashion industry, which food is not necessarily a priority.
Alyssa Rapp: People don't eat much there. There are other things that are consumed there, jokes aside.
Johanna Almstea...: Seriously, but I've told this story before I think on this podcast, but my first big job out of college was at Prada, and it was really, really, really intense. And I was in the advertising and communications department of Prada and it was real intense. And food was not a priority there. And in fact, we would get in trouble if someone microwaved anything that had strong smells. You weren't allowed to have strong smells in the office. I mean, it was a whole thing, right? And then I left there and my next job was at Ralph Lauren. And I remember walking into Ralph Lauren and in the beautiful showroom reception area, there was a giant silver urn. It was like this big. It was huge, filled with M&Ms. And then you would go into the back kitchen where the offices were and there was always breakfast stocked every day.
There was bagels and there was cream cheese and fruit and coffee and whatever. And then they would have snacks throughout the day and cup of soup. I ate so much cup of soup. What is it? Cup of Noodles, whatever that was. So again, it wasn't super healthy.
Alyssa Rapp: Cup of Noodles, Cup of Noodles.
Johanna Almstea...: Cup of Noodles. This was back a long time ago. But I remember the feeling was just so different of like, oh, they care. They care that I'm nourished. They're not mad at my food. And so I think that's wonderful that you actually talk about it and talk about it as a CEO, that that's one of your priorities.
Alyssa Rapp: I mean, listen, it's also incredibly Machiavellian. If you have good snacks in the office, people leave less and they work more. So there's nothing completely free about it, but there's definitely... I hate being hungry. And so why if I need that in an office environment, would we not want to have that set up that way? So Surgical Solutions, there's lots of great snacks. And then in our office in Austin for Empire Aesthetics, there are incredible snacks, best I've seen. And you go to places like Google or Meta or anything else today, which I haven't mentioned in a while, but their kitchens and-
Johanna Almstea...: That's a whole other level.
Alyssa Rapp: That's a compensation benefit strategy. Yeah, it's a full-blown restaurant. That's not what I'm describing, but just snacks, a good coffee machine, nice tea, plenty of water and decent snacks, healthy snacks or grab and go. I think it's table stakes. And I also will say, I also think having a decent place to microwave your food, you brought it up in a joking environment, but bringing lunch is healthy and economical. Maybe not everyday, maybe you have lunch together as a team once a week, but I think making that sort of the culture of what's done and talking about it. I mean, when I order lunch for the team, I hope that everyone's going to take 10, 15 minutes to break bread together and have a conversation about it, otherwise, why am I buying you lunch?
Otherwise, make it easier for people to bring what they want and have it. It's just the way of the world. And yet, I think this transcends industry. For school board, we do a coffee truck once a year. One of my favorite things to do, we go into the schools, we thank the teachers, school board members can go, I always sign up first. The coffee truck guy is great and the chai tea is terrific, which is one of my favorites. But the concept of like it's seven in the morning, you get there, you get to see the teachers come in, you thank them in person, you have five minutes of conversation. I took a $5 tea or coffee and someone feels genuinely appreciated? That's worth a lot more than the five bucks.
Johanna Almstea...: Right, totally. Totally.
Alyssa Rapp: And that's the gift of food, right? The benefit of the breaking of the bread is the value of it's higher than the dollars. I sent champagne to all of my board members this year and people were genuinely appreciative, and my team, my executive leadership team and our seller partners. And I got a lot of really nice thank yous. It was a really nice bottle. Let's be clear. I have good taste in champagne, but it wasn't-
Johanna Almstea...: You're not fucking around when it comes to champagne.
Alyssa Rapp: No, no, no. I mean, A, it's one of my favorite things to drink, period. And B, I'm not sending you... It's a reflection of my taste to send you something. So I'm not going to send you something obvious and it is going to be delicious and all the things, but people are unusually appreciative. It was a nice enough bottle to have with Hanukkah or Christmas or New Year's. And I'm not saying I'm so wonderful. I'm saying like a really nice gift of even something that obvious. It's thoughtful, it's delicious and it's fun and it's festive and hopefully the goal in sending it was for people to feel valued and appreciated.
Johanna Almstea...: Yeah. It makes people feel valued, I think. I hope, right?
Alyssa Rapp: I hope too.
Johanna Almstea...: Okay. So you've had like nine million achievements in your life.
Alyssa Rapp: Yeah. Hardly.
Johanna Almstea...: I want to know which one you're most proud of. What are you most proud of?
Alyssa Rapp: I have said in public environments like an anniversary party that falling in love isn't a choice, but getting married is one and marrying my husband was one of the best decisions in my life. I think going to business school at Stanford was an unusual decision. My parents wanted me to go east to the Stanford of the East, haha. And a gutsy one. It set the trajectory of my career. So I think trusting my gut on that, I'd never been to Stanford in my life, and I got in third round and it's a whole funny, interesting story. And I didn't go to the admit weekend because I was traveling at the time in New Zealand and Australia, and sort of a real gut instinct that I really listened to and that was a really good decision. I think those are two probably of the best.
Johanna Almstea...: Okay. Is there anything that you once believed about yourself that you've since outgrown?
Alyssa Rapp: Yeah. I mean, I think I thought for sure I genuinely thought I wanted to be president and I definitely have had conversations with people while running for office in DC and other places. And I definitely feel like this time as a school board member is incredibly important and I'm proud of the work we're doing and it's hard work and it's a lot of time. It's a lot of education and it's micro local, it's not national. I don't think I need that anymore for my ego or for my vision of myself to have been complete. It is a thankless, brutal job. I've had a brother who worked for President Obama in the White House. I've had a mother appointed by him. I've known many members of Congress and the Senate. I don't think my idealistic view of Washington DC is what it once was. So I have let go of that.
Now, down the road, do I think running a state or being a high level executive in a state is more like running a business and has really important profit and loss responsibilities and you can make big impact? Yeah. So have I said I'll never have involvement in the executive branch? No, but I'm not doing it right now. It's the furthest thing from my mind. And I definitely think that those childhood dreams, abandoned may be too strong, but I no longer have that same aspiration. The shine around it is not what I thought it was. I think that you can have much deeper impact potentially on being a few public company boards or private company boards or investing in meaningful people and companies and entrepreneurs. I think that you can have impact on people's lives in many other ways besides that that are as great, which I don't think I had the insight as a kid to realize.
Johanna Almstea...: You've seen behind the curtain a little bit.
Alyssa Rapp: Oh yeah. It's a rough job. No thanks.
Johanna Almstea...: No, thanks. Okay. So is there anything that you've said no to in your life that you wish that you had said yes to?
Alyssa Rapp: I mean, life, you can't live it in hindsight, right? And I have no regrets per se. When I was founding my first company, it was in the early days of Facebook and had a couple of close friends who were going, there was employees one through 20 who were like, are you sure you don't want to look at this thing? It looks pretty interesting. I'm like, no, I have to do my own thing. That would have been a very lucrative outcome.
Johanna Almstea...: It would have been, yeah.
Alyssa Rapp: So regret, no, reflecting on sliding doors, maybe. My stepfather, when I was first back in Chicago after college and working in politics, wanted to buy my first condo, I thought it'd be a good small investment, and he was in the real estate space and offered me a unit in one of his buildings. I'm like, no, I have to do it on my own. I have to do my own thing, not in one of your buildings. That was the dumbest thing I've ever... That was probably the worst dumb call I've ever made. Not only would I have made money, I would have learned from him. That was just stupid youthful headstrongness that I would have done differently. That's probably my most meaningful regret because I would have learned from him. And then on the third front, it's related, but in learning from mentors, my favorite mentor who just passed from business school Joel Peterson and I were talking about co-teaching a course at Stanford Business School.
It's one of the most wonderful classes there called Managing Growing Enterprises. And I got too busy with my current CEO job, being a mom, being a wife, all the things, that level of travel to California every week was just too much. It was not feasible. So I regret that he passed before we could teach that class together because it would have been a real honor, but nothing but gratitude for his even willingness to consider it and no regrets that I didn't make the right decision at the time, just sadness of opportunity not fulfilled.
Johanna Almstea...: Yeah, that's hard. So I feel very strongly about women continuing to dream for themselves. What are you dreaming about these days? Or do you?
Alyssa Rapp: Yeah, of course. I do dream of a time in the future, 10 or plus more years from now where there's a little bit more breathing room. So whether I take a teaching assignment in London and Hal would join me or we do some big six month trip with our family as a unit or have a little bit more time to spend in places I love like Jackson Hall, Wyoming or places he loves like the ocean. Not to do less, but to do differently, I think would be a dream I've had in the back of my mind that I don't know if I've articulated that crisply. I don't even know what retirement means. My stepfather worked until he was 93 years old and loved every minute of it. So that's not what I'm really saying. It's just a different pace, cadence, more geographic flexibility is something I dream about. What about you? What do you dream about?
Johanna Almstea...: I dream about horses and I dream about more time in a very magical beach place that I love that I grew up going to and I dream about giving that to my kids. Those are the current dreams.
Alyssa Rapp: All makes sense to me.
Johanna Almstea...: Yeah. It changes though. I keep dreaming, which is nice.
Alyssa Rapp: It's fun.
Johanna Almstea...: Yeah. And I dream about this podcast getting bigger and better and book deals and that kind of stuff.
Alyssa Rapp: Well, you're off to a great start, my friend. You're off to a great start.
Johanna Almstea...: Thank you.
Alyssa Rapp: You could probably have a book deal tomorrow if you just patched them up with all the amazing interviews you've done.
Johanna Almstea...: Oh, thank you so much. Okay. So it doesn't sound like you take many of these, but what is the perfect day off for you?
Alyssa Rapp: I mean, a long hike in a mountain I love with a long lunch thereafter with people I love. That could be lots of things. And a great book and a great movie would probably be a great... And a dinner party I didn't have to cook, but have my favorite people attend would probably be the world's greatest day or two days. I don't pack all those things into one day lately. There's too much other obligation, but I try to chip off pieces of those things as often as I can.
Johanna Almstea...: Little bites. You talk a lot in your book also about the idea of work hard, play hard, which I also subscribe to that philosophy and have. Tell me why that matters to you.
Alyssa Rapp: I mean, I think blowing off steam matters. And I don't have embarrassment about saying that. My husband loves live music. We got invited to go to the Eagles concert at the sphere. Yes, let's do a day trip to Vegas for that. Why wouldn't I do that? Or our 13-year-old, as you know, is a serious tennis player. My one real tradition every year is I take her to the US Open Women's Finals for her birthday. That's a day trip. It's a lot. I mean, we're going on United, not NetJets, to be clear. And so it's a lot, right? But it wouldn't even occur to me not to do that because showing up matters and doing things that are perceived as playing hard, but really are probably better described as intensive experiences that are immersive that pull you out of your day-to-day life is what I find some pressure valve release from and enjoyment.
Johanna Almstea...: Yeah. Celebrating your wins, celebrating your losses sometimes too.
Alyssa Rapp: All of it. And I think celebrating the wins really matters, even small ones.
Johanna Almstea...: Yeah, I agree. That's something that I have as my kids have gotten older and I've gotten a little more like brain power and I'm not in the corporate world anymore as much, that has really become more important to me. We have to make sure we stop and celebrate this stuff, even the little things. We have to. Otherwise, it just flies by.
Alyssa Rapp: I agree with you.
Johanna Almstea...: Okay. Well, in the spirit of playing hard, we are now at the very, very exciting time in this interview of the lightning round of silly questions. Some of them are food related, some of them are not. I know you are a very academic person. I know you think about things very hard and you are very strategic. Do not think hard about these. Just say exactly what comes to your mind first right out of the gate and do not overthink this. Okay? Favorite comfort food.
Alyssa Rapp: Cheese.
Johanna Almstea...: Specific cheese? Any type?
Alyssa Rapp: I love gouda.
Johanna Almstea...: Oh, yeah. I love gouda. Do you like smoked gouda? Have you ever had smoked gouda?
Alyssa Rapp: No, I have and I don't.
Johanna Almstea...: Straight gouda.
Alyssa Rapp: I like gouda, straight gouda, from the Netherlands.
Johanna Almstea...: Oh, you're Dutch. Right. I forgot that part. Yes, of course you love gouda. I love that they sell gouda at the airport.
Alyssa Rapp: It's the best.
Johanna Almstea...: It's the best. Okay. What is something you are really good at? Beyond being a CEO, because we know that.
Alyssa Rapp: Making breakfast. It's the only meal day I'm really good at.
Johanna Almstea...: Okay. What do you make for breakfast?
Alyssa Rapp: Eggs, crepes, waffles, coffee from my husband, smoothies for my kids. Breakfast, I do well. Everything else it's downhill from there though, just [inaudible 00:55:51].
Johanna Almstea...: Okay. I like this. What's something you're really bad at? I feel like maybe you're not bad at-
Alyssa Rapp: Lots of things. Ironing, I stink.
Johanna Almstea...: Oh, I suck at ironing too.
Alyssa Rapp: I really stink. Really stink, not good. Not particularly good at folding dry laundry either. Washing it, I'm fine, but not particularly good at folding. Ironing I stink.
Johanna Almstea...: Yeah. Okay. Favorite word?
Alyssa Rapp: I was going to say supercalifragilisticexpialidocious, but I don't know why. Maybe because we listened to Julie Andrews on the drive back yesterday.
Johanna Almstea...: Because that's fun. I love that. I won't make you spell it. Okay. Least favorite food. Like you're just not.
Alyssa Rapp: I mean, I'm a pescatarian, so I don't eat anything with a heartbeat besides a fish.
Johanna Almstea...: Okay. No meat.
Alyssa Rapp: Mm-mm.
Johanna Almstea...: Least favorite word?
Alyssa Rapp: No.
Johanna Almstea...: You're not alone on this podcast. Best piece of advice you've ever received.
Alyssa Rapp: Respect your body, you only get one of them.
Johanna Almstea...: I like this one. Okay. If your personality were a flavor, what would it be?
Alyssa Rapp: Aged Merlot.
Johanna Almstea...: I like it. I like it. Got lots of depth. Got lots of-
Alyssa Rapp: Trying. Trying.
Johanna Almstea...: Trying. Okay. So last supper, you are leaving this body and this earth that you've taken very good care of this body and this earth since you've been here, so it's a celebration. We're not sad. We're just moving on to the next chapter. What are you eating tonight?
Alyssa Rapp: Caviar and some great champagne.
Johanna Almstea...: There you go.
Alyssa Rapp: Easy.
Johanna Almstea...: Have you had a moment in your life when you've had to eat your words?
Alyssa Rapp: Of course.
Johanna Almstea...: Can you think of any?
Alyssa Rapp: Yeah. I mean, I thought I was going to raise a special purpose acquisition corporation that took a company public and worked my tail off for two years and we didn't get the job done. We fell short. Stunk.
Johanna Almstea...: That stunk. Yeah. I'm sorry. That just got me in my gut.
Alyssa Rapp: It happens.
Johanna Almstea...: It just got me in my gut.
Alyssa Rapp: Yeah, it stunk. It stinks. We had the right team and the right strategy and the wrong timing and that stunk.
Johanna Almstea...: Yeah. That's really hard. Okay. On a lighter note, if you have to eat one food for the rest of your life, I feel like I might know this because you talked about it in your book, but maybe I'm wrong. All day, every day it's going to sustain you. You don't have to worry about the nutritional balance. What would you eat?
Alyssa Rapp: I mean, popcorn or cheese.
Johanna Almstea...: Oh, I thought you were going to say quinoa because you were talking about quinoa in your book.
Alyssa Rapp: I do love quinoa, but-
Johanna Almstea...: But that's for nutrition.
Alyssa Rapp: If it were nutritional value, that's the obvious answer. I'm very versatile at that. But if it was just flavors-
Johanna Almstea...: Popcorn or cheese.
Alyssa Rapp: Mm-hmm.
Johanna Almstea...: What do you put on your popcorn?
Alyssa Rapp: I like just straight up olive oil with sea salt. Sometimes truffle salt. That's the real secret.
Johanna Almstea...: That's fancy.
Alyssa Rapp: Made old school on the stove, by the way. Not in the popper.
Johanna Almstea...: Do you have the Jiffy Pop thingy?
Alyssa Rapp: I do have it, but that's not what I'm talking about. I'm talking about pan, olive oil, corn, truffle salt.
Johanna Almstea...: Oh, I like it on the stove too. I agree. I think it's delicious. Okay. Where's your happy place?
Alyssa Rapp: Jackson Hall, Wyoming.
Johanna Almstea...: What did you have for dinner last night?
Alyssa Rapp: I was driving back from my kids' tennis tournament.
Johanna Almstea...: That's why I love to ask this question. It's so good.
Alyssa Rapp: It's not a good answer. It was bad. Roadside coffee is the honest answer. It was some peanuts. It was a bad-
Johanna Almstea...: See?
Alyssa Rapp: It was not great. Not great.
Johanna Almstea...: See? This is why we talk about it because some people sit down and be like, "I had a steak frit and some grilled asparagus." And other people are like, "I had two Cheetos and a pickle."
Alyssa Rapp: It was not pretty. I'm just saying it was bad peanuts and bad-
Johanna Almstea...: And bad coffee.
Alyssa Rapp: Roadside coffee and I'm a tea drinker, so that was really bad. Had to drive home late. I had to get home.
Johanna Almstea...: Yeah. Oh, God. Can you drink coffee that late and still go to sleep?
Alyssa Rapp: I had to drive four hours from Toledo here, so I wanted to stay awake. And then when I got home, I was still that tired. Yeah. But normally not. I'm a tea fanatic. That was the exception.
Johanna Almstea...: How do you make your tea?
Alyssa Rapp: As was having peanuts for dinner. I really love great black loose leaf tea in the morning in a tea steeper with a dash of 2% of whole milk. That's my-
Johanna Almstea...: No sugar, no honey, no nothing?
Alyssa Rapp: Mm-mm.
Johanna Almstea...: Delish. Okay. What do you wear when you feel like you need to take on the world? Like big meeting, hot date.
Alyssa Rapp: Oh, that's an easy answer.
Johanna Almstea...: Oh, I like this.
Alyssa Rapp: Well, I have it in the book, actually. I think you need to put on your Superwoman suit. And I have found over the last 10, 15 years that St. John dresses or suits, the knits, they work for me and they travel well. And so I have them in fancy and every day. So I would say a St. John suit or dress.
Johanna Almstea...: I love that. You're like a brand ambassador for them.
Alyssa Rapp: Yeah, except I have no brand ambassador benefits, but I'd be happy to get them at some point.
Johanna Almstea...: St. John, are you listening? She wears you all the time.
Alyssa Rapp: I do, all the time.
Johanna Almstea...: You need her on your roster guys. Okay. Most memorable meal you've ever had.
Alyssa Rapp: I love The French laundry. I typically go annually. It's my favorite ever.
Johanna Almstea...: Okay.
Alyssa Rapp: That's easy.
Johanna Almstea...: Love that. Go-to coping mechanism on a bad day. So shit is going sideways. Kids are sick. Your board members are pissed. Something's going on at work, in school for the kids. What's going on? What do you do?
Alyssa Rapp: Glass of wine with my husband when the day is done.
Johanna Almstea...: Nice. Nice. Okay. Dream dinner party guest list, dead or alive. Everyone says yes. Who's coming to your dream dinner party? Because you said you wanted to have more dinner parties.
Alyssa Rapp: Yeah. I think it would be really interesting to see some of the founding fathers for dinner and their wives. I'd love to see what was going on in their heads during the American Revolution beyond what we've read and heard and seen in Hamilton and all the things. So founding fathers and their wives.
Johanna Almstea...: And their wives. I like it. I want to know what's going on through their minds, right? Ladies?
Alyssa Rapp: Yeah, all of it. All of it. If I had to pick a theme, that'd be it. Now, if you're talking about favorite musicians, U2. If you wanted to be really spicy, throw in some of your favorite actors, there are too many to count. I do think Julie Andrews is pretty remarkable. She's had such a diverse career.
Johanna Almstea...: I mean, Julie Andrews, U2, and the founding fathers? This getting good.
Alyssa Rapp: Dinner party's full.
Johanna Almstea...: This is getting good. This is getting so good.
Alyssa Rapp: There you go.
Johanna Almstea...: Are we asking U2 to-
Alyssa Rapp: We've got music and we've got politics.
Johanna Almstea...: Yeah. Are we asking U2 to play anything at this party or are we just letting them just hang out?
Alyssa Rapp: Of course. So does Julie Andrews. Yeah, of course.
Johanna Almstea...: Oh, she's singing like the Hills Are Alive? What's happening?
Alyssa Rapp: I mean, who knows? Something.
Johanna Almstea...: These are a few of my favorite things.
Alyssa Rapp: These are a few of my favorite things.
Johanna Almstea...: I love it. Okay. Lastly, finally, what is one thing you know for sure right now in this moment you don't need to have known it yesterday, you don't need to know it tomorrow. What is something you know right now?
Alyssa Rapp: Every day is a privilege. Maximize it.
Johanna Almstea...: I love that. Can you please tell the nice people where they can find you if they want to learn more about you and your story?
Alyssa Rapp: Oh, you're so sweet. Yes. You can find me at Alyssa Rapp, A-L-Y-S-S-A-R-A-P-P.com. And you can find my newsletter there, Hacks Newsletter. You can find my book there, Leadership and Life Hacks or on Amazon. You can find me at alyssarapp.com.
Johanna Almstea...: There she is. Guys, get her book. It's great. Subscribe to her newsletter. You're going to learn something. You're going to be inspired. Thank you, thank you, thank you, Alyssa Rapp for taking the time out of your very, very, very busy life. I know people are going to be so inspired by you and your story, and I'm so grateful for having spent this time with you. It's been a gift.
Alyssa Rapp: Thank you for the invitation. You are a talented interviewer and it was a privilege to be on. And I think Eat My Words is now something I'll look forward to featuring in my newsletter, but also sharing with my friends. Your approach is authentic and of the times. Thank you for the opportunity.
Johanna Almstea...: Thank you so much. You're so sweet. This has been wonderful. Well, that was a blast. I am so inspired by her. She just raises the bar for life, for mothering, for leading. I think it's all so exciting. So I hope that you guys felt inspired and excited by her. As always, we thank you so much for tuning in. Thank you for your support. We are growing this audience bit by bit, and we're so excited for what's to come this year, and we couldn't be doing it without all of you. So if you're not already doing so, please follow us on social media. We are at Eat My Words The Podcast on Instagram and TikTok. We are also in those comments all the time. So tell us what you want to know, ask us questions, tell us what guests you want on. If you think somebody who you know might like this episode, please share it with them.
We are trying to spread the word and share people's stories with the hopes of inspiring and exciting other people and making people feel seen and heard. So thank you, thank you, thank you and I will catch you on the next one. This Eat My Words podcast has been created and directed by me, Joanna Almstead. Our producer is Sophy Drouin, our audio editor is Isabelle Robertson and our brand manager is Mila Bouchna.