Inspired with Alexa von Tobel
00:08:04 · Alexa von Tobel, Penny Pritzker
[00:08:04] S0: Yeah. I I I always say I think it gives... Going through something so hard, so early gives you a different gear. And the gear really is one of a zest for life, risk taking, comfort with risk. And I always say, if the roof's over your head and you can breathe, you're gonna be okay. [00:08:23] S1: Well, I think that... I mean, you and I have talked about this. You know, one thing that happens is, I think, when you've overcome a number of very difficult situations in your life, as you have, as I have, as many people have, when you then face the next one, the next challenge, you say to yourself, okay. I know this is gonna be hard. I'm not exactly sure how it's gonna work out, but I know I have it in me to figure this out. [00:08:48] S0: That is one of my favorite things about you, actually, which we will get there later. But when things get really hard, you become your best. Brings out a part of you that I've watched many times now. You become sturdier. And it's something I really admire about you. Okay, another thing I admire about you is when you were 16, your grandfather because your dad had now passed away you wrote to your grandfather a letter and said, why are you only talking to the boys in our family about business? And he responded by putting you in an accounting class. It is mind blowing to me to think that you, of all women, grew up in a world where women weren't supposed to be in business. I mean, I'm like, are we still gonna march for this? To say more, what made you write to your grandfather?
00:08:48 · Alexa von Tobel, Penny Pritzker
[00:08:48] S0: That is one of my favorite things about you, actually, which we will get there later. But when things get really hard, you become your best. Brings out a part of you that I've watched many times now. You become sturdier. And it's something I really admire about you. Okay, another thing I admire about you is when you were 16, your grandfather because your dad had now passed away you wrote to your grandfather a letter and said, why are you only talking to the boys in our family about business? And he responded by putting you in an accounting class. It is mind blowing to me to think that you, of all women, grew up in a world where women weren't supposed to be in business. I mean, I'm like, are we still gonna march for this? To say more, what made you write to your grandfather? [00:09:36] S1: So it was my grandfather's eightieth birthday. [00:09:39] S0: Oh my goodness. [00:09:39] S1: And my mother said, you can give your grandfather whatever you want for his birthday. And I'm thinking, here's a person in my eyes who'd accomplished everything and knew everyone. [00:09:51] S0: Yep.
00:09:51 · Alexa von Tobel, Penny Pritzker
[00:09:51] S0: Yep. [00:09:51] S1: Right? And so I was like, what am I gonna do? And then I thought, you know, I wanna tell him about who I am and what I wanna be. And he had always loved me very much, and we've been very close. But I'd never really sort of expressed to him what I did. So I wrote... Back then, they're... You know, colored stationery was new. It was like a big thing. And so I had this green stationary. I'll never forget it. And I wrote him a letter, and I basically said, dear grandpa, you know, you know, happy birthday. And I just really don't understand why you only talk business to the boys in the family and not to me. I'm very interested in business. So I arrive at his eightieth birthday party, and it's a who's who, as far as I could tell, is a 16 year old. And it's a big shindig. And my grandfather was not that tall. He was a little bit like my height. And my grandfather finds me in the middle of this party, and he's got his tuxedo on because back then you wore a tuxedo to a party. And he has my letter is in the breast pocket sticking out of his tuxedo. [00:11:01] S0: I love this.
00:11:01 · Alexa von Tobel, Penny Pritzker
[00:11:01] S0: I love this. [00:11:02] S1: And he grabs me and he pulls me into the hallway and he pulls my letter out. And he says to me, he said, Honey, I was born in 1896. How am I supposed to know girls, That was the word he used. Girls are interested in business. He said, but if it's something you really care about, because he had always said, I don't care what you do as long as you're passionate about it and really pursue it with all your energy. So if that's something you're really interested in, come spend time with me this summer, several weeks. And one of the things we're gonna do is we're gonna work on accounting. Because his view was, if you don't understand the income statement and the balance sheet and you can't do t accounts, you don't really understand what's going on in a business. And so I did that. And first of all, it was magical to spend time with someone who had seen so much and who had so much wisdom. But it also gave me a lot of humility about how hard it is to do what he had done. [00:12:06] S0: I love that. Also, what a great grandfather. Like, that was priority of his evening. [00:12:13] S1: I love it. I I... It was really fabulous. You know? And and... But I also appreciated his honesty. In other words, hey. You're stretching me a long way from where I started in my life. And so this is not necessarily comfortable, but I'm up for the challenge. So he also set a great example.
00:12:13 · Penny Pritzker, Alexa von Tobel
[00:12:13] S1: I love it. I I... It was really fabulous. You know? And and... But I also appreciated his honesty. In other words, hey. You're stretching me a long way from where I started in my life. And so this is not necessarily comfortable, but I'm up for the challenge. So he also set a great example. [00:12:31] S0: I know. I love it. I think it's something we can all do more of. Fast forward, you went to Harvard undergrad where you got a degree in economics, and then you went to Stanford for your MBA and for your law degree. So you got a lot of education very, very quickly. And when you came out and actually, an important stat. To this day, you have built almost seven plus businesses and I'm sure that even underestimates some of them. And that entrepreneurial spirit was really, really there. Talk just a little bit about you. You finished, you leave Stanford, and you start building businesses. How would... How do you remember that?
00:13:15 · Penny Pritzker
[00:13:15] S1: When I finished graduate school, you know, I went and and spent some time working with my family. And I was in a, quote, training program and for about eighteen months or twenty four months, and I was... Feel like I did one of everything, an acquisition, a disposition. I wrote a marketing report. I had to do something of... A little bit of everything. But I felt... And I said this to my uncle, who at the time was kinda chairman of everything that we... The family was doing. I said, you know, look, I love being here and I love working here, but I feel like I'm a fifth wheel. I don't think what I'm doing is making a difference. We have this idea to start a senior living company. It's kind of floating in the ether at the hotel company. I'd like to do that. And I was 27 years old. I had a ton of formal education, but I didn't have real... And I'd worked through school and during summers and everything like that, but I'd never built a business. Yep. But I had an idea. I thought I understood what it meant to build a senior living business because my mother also passed away at a very young age, and she was an only child. So I was responsible for taking care of my grandmother. And I realized a couple of things about that. One is my grandmother was lonely because many of her peers had passed away. She was bitter because of it, and she needed care. But back then, getting care, reliable care, was really difficult. And all of a sudden, I get a call in the middle of the night. Well, person taking care of her, because she was in a wheelchair, had left in the middle of the night. And so I'm getting up at, you know, 26 years old and driving over to her house to figure out what to do. And I thought, there's a business in this. There's something there. I didn't know what it was, but I said, I wanna go figure it out. I understood pretty well the hospitality business because I literally grew up in it. Yep. You know, from age five, was going with my dad to our motels and checking out, you know, what was going on. So for me, that was... It was a natural to try and start something. And also, frankly, Alexa, it was harder then as a woman to gain access to, let's say, fast growing opportunities. And certainly there wasn't a clear path to leadership.