Inspired with Alexa von Tobel
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.
00:15:52 · Penny Pritzker
And so I figured if I started something and built it, at least it would be harder to get rid of me because I was sort of theoretically essential to the business, if you will. So don't kid me, that was part of the motivation. So anyway, that's how I ended up becoming an entrepreneur. It was the way I felt that, you know, there weren't a lot of paths for me to grow in existing businesses. You know, the guys were kinda looking out for the guys. And so I was like, okay, then I'll build it. I'll do it from scratch. And once you've done that, once you have... And and you learn a lot. I made so many mistakes. Unbelievable the number of mistakes I made and unbelievable some of the bad decisions I made. But I learned from them, and what I learned is is if you recognize you made a... You hired the wrong person. Literally, I didn't know how to fire someone. I had to call my uncle, and I said, I hired the wrong marketing person, but I don't know how to fire them. Could you give me a tutorial on how do you tell someone it's not working out? And, of course, I was racked with guilt and everything. Of course. But he helped me understand that when someone's not in the right job, they usually know it too and that you need to help them understand that it's just not working. It's often portrayed as being very brutal, but this was really... It was clear that this person I'd hired, they didn't really... They weren't comfortable in the job either. So, anyway, I learned a lot by doing.
00:17:36 · Alexa von Tobel, Penny Pritzker
[00:17:36] S0: There's a natural value system in your history around the the love of the builds. And you've even said it a few times. There's something honorable about it. And I think you and I have not really ever had the conversation directly of we believe there's something noble about building a net new business from scratch, taking a white piece to paper. I believe it's incredible because there's a lot of innovation rooted in it. Right? When you're innovating, you're making something better. You're rarely building something that's worse than what exists out there. And so I always love that piece. Why do you think you like building things? Like, what what what part about it makes you feel so... That is noble? [00:18:19] S1: Well, I think there are two things that are important. First is to build a business that succeeds means you're filling some need that society has. Yep. Businesses don't endure if society doesn't need them. Doesn't matter how much effort you put into it. I think the other part that I learned, and I learned this as a young person, I watched my parents, you know, help the bellman become ultimately the general manager of a hotel, if you will, or I watched this... Them helping people grow. And I and I really felt the humanity of that. I felt the... Boy, if you can create a new entity that employs people and gives people purpose and they feel belonging and the culture is healthy, we've all been seeing unhealthy cultures, but you can create a healthy culture where people feel respected and trusted. What's wrong with that? That feels noble to me.