The Greatest Story Ever Podcast – #10: Turning A Free Vacation Into A Job with Carol Roth

Carol Roth is an entrepreneur, creator of Future File, a commentator on TV and radio and she has her own podcast The Roth Effect. Carol joined me about the time she took break from post-college pageant life to go on a job interview she thought was just an excuse to go on a free vacation, and ended up with a career. It worked out pretty well for her. 

If you think you can top that story, shoot me an email at GreatestStoryEverPodcast@gmail.com

Photo by Joseph Barrientos on Unsplash

Keith Conrad 0:00
Thanks so much for joining me, Carol.

Carol Roth 0:01
I am pleased to be here, Keith.

Keith Conrad 0:03
Now my first job, I basically just worked in a grocery store and chopped up fruits and vegetables. Which is interesting because most people would be terrified to know that I was like holding large knives. But I mean, at the end of the day, it's not that unique, like a lot of people's first jobs tonight in a grocery store. But so you wanted to share the story of your first job because it's a little bit more unique.

Carol Roth 0:30
Yeah, well, it's just to be fair and clear. It's not actually my first job. I did the working in the day camp kitchen for the summer when I was 12. And babysitting and y'all you know, all kinds of minimum wage things but this is my like my first real job out of college. And to give context to the story, I think it's helpful to understand where I came from. So I came from a family in suburban Chicago, where I was the first person in my life family to graduate from college. And so, you know, coming from a blue collar family, we didn't really have the money to afford a fancy education. But I did get into Wharton, the best undergraduate business program in the country at the time, I think still still pretty much as at University of Pennsylvania, and my dad's like, how are you gonna afford this Ivy League education and I kept explaining to him, Well, based on my research, people make a lot of money coming out there so I should be able to pay off my debt. So he was down with that it was like okay, as long as you can pay down the debt quickly, you can go there. So I stumble in to the University of Pennsylvania, and, you know, take on $40,000 in college debt over the years and this is back, you know, in the early to mid 90's. adjusted for inflation.

Keith Conrad 1:59
There's been a little bit of that.

Carol Roth 2:00
Yeah, so you know, but But definitely, I mean, right now 40,000 is sort of the average that people have coming out of school. So I had hit that more than 20 years ago. And as I was approaching, you know, coming coming up and trying to figure out what I wanted to do, it's was sort of presented to me that there were a couple of options and one of them was investment banking. And the one of the things that you learn when you do investment banking interviews, is that if you get past the first round, and sometimes the second round, they have you out for what's called a super day where you get to go to the corporate headquarters, and you get to meet a whole bunch of people and have like, you know, eight interviews in one day to decide if you want to go work there.

Keith Conrad 2:52
You know, that's funny, because when I got my first job back here in Chicago and radio basically I unintentionally had the same thing where I had to, because of the fact they're bringing me in from out of town. They had me meet with basically like everybody at work there and do an interview. And by the end, I was just like, dead. I'm like, I don't want to talk to anybody for

Carol Roth 3:15
Yeah, the whole process is not for the faint of heart. And I interviewed in other realms to and consulting and whatnot. But me being me. So you know, I'm come from this blue collar family. I come from a family where we never went on vacations because we couldn't afford me the best we ever got was that maybe one or two years where we went up to Wisconsin, you know, with another family to a place that had like a hill that we could slip or something like that. But you know, my parents were struggling to afford the house but they were they had a sin and all that kind of stuff. So we never went on vacation. So I hadn't been anywhere. And so me being the schemer that I am decided that, you know, there are these places Like in places like California, like there's an investment bank in San Francisco, I've never been to San Francisco, I would love to go to San Francisco. What if I try to get an interview with one of these places, they'll fly me out for free to go on a trip to San Francisco. This is a brilliant idea. So I'm dropping my resume for you know, all the places I might want to work, the names that you hear the Goldman Sachs, the Morgan Stanley's and whatnot. And then I start like, the Montgomery securities and the Alex brown and all of these boutique banks that were just up and coming at the time in San Francisco, in hopes that you know, I could kind of rig their process in terms of the interview, and Montgomery securities decides that they want to interview me and I'm like, sweet, okay, it's this great, I'll totally like kill this process. Lois lo and behold the day of their interview Have a conflict. And what does Miss Ivy League educated person interviewing for an investment bank have a conflict with? Well, it happens to be the day that I am competing in the Miss Illinois pageant.

Keith Conrad 5:18
Why wouldn't it be?

Carol Roth 5:19
obviously, yeah. And I got totally roped into that, because for anybody who knows me and Keith, I'm sure you will appreciate this. I'm the kind of person if somebody's like, Hey, why don't you try that? I'm like, Okay, sure. Why not?

Keith Conrad 5:34
I've never done before. So I don't know that I don't, right?

Carol Roth 5:37
Yes. So I was I was working the summer before. My health club in the suburb of Chicago and the woman who owned the health club was a former beauty queen, and she decided that I would be great in the pageant arena, which to know me is hilarious. I would not be great in the pageant arena, but it was like okay, whatever. I'll just like Apply and see if I can get in and you have to do like the glamour shots and the bathing suit shots and whatever. And lo and behold, I didn't even know there are two different tracks of beauty pageants. There's the ones with the talent, which is the Miss America and there's the one without the talent, which is the Miss USA, which is one that used to be owned by the Trump Organization, by the way. And I had, unbeknownst to me applied to the Miss USA track, so I didn't even need to have this is like totally low budge, I probably would have been better off in the Miss America track, which is more of a scholarship pageant. But anyway, so

Keith Conrad 6:37
So you were working on you're juggling and it turned out you didn't need to!

Carol Roth 6:39
Did not need to know how to juggle the knives so that you know, I figured I just put that aside in case it came up in any of my investment banking interviews. And so, lo and behold, you know, I get accepted and I go through this whole thing. I go through this training and I you'll learn how to be in a pageant. So So I get this interview, and there's a conflict with my beauty pageant. And I'm like, Well, I'm not gonna jeopardize this free trip to San Francisco. So let's see what can happen. And by the way, I haven't even gotten past the first round of interviews yet, but doesn't matter. I'm feeling very confident about this.

Keith Conrad 7:17
You're just assuming you can.

Carol Roth 7:19
Just like, well, I feel like I can do this. So I call up the guy and I'm like, you know, Hi, I'm so excited. I'm really, really interested in Montgomery securities. It sounds so interesting. I have a little bit of a problem. I'm competing in the Miss Illinois pageant, the same day as the investment banking interview, and I was wondering if there's anything else we can do, and he's like, Can I swear on this podcast? Are you gotta fucking be kidding me? Like, seriously, you're telling me that you're gonna be in a beauty pageant and you're missing your investment banking interview, and I'm like, Yes, sir. I actually am, but I'm really, you know, flexible and entrepreneurial. And I could go up to New York and meet one of your bankers up there for dinner. Or, you know, whatever. And he's like, Oh my god, seriously? Okay, fine. Tell you what, what to do. Call me back in like three days, let me let me sit on it and see if there's anything else we can do. So I call him back, and like three days, and he's like, I don't know, and, and we just did this dance back and forth where he just kept putting me off like two days at a time, three days at a time, whatnot. And I must have called him 17 times and on the 17th time, he's like, you are the most persistent motherfucker I have ever met in my entire life. Fine, I am going to let you go up to New York and meet one of our bankers up there for an interview. And then of course, because you know, me just being me and having all the nerve. I was like, Well, do you think there's any way you guys could reimburse me? Get off there because I was doing it and I have no money and they agreed to reimburse me for the train tickets. So So now I've got a free trip to New York City. That's okay, first step. And

Keith Conrad 9:06
Especially when you got to this point, and they were like, yeah, we'll meet you in New York. You should start seeing what else you could get right?

Carol Roth 9:12
Yeah. Worst they can say is no, right?

Keith Conrad 9:16
Can we do an interview in Yellowstone National Park?

Carol Roth 9:21
So you know, so I take the train I get in the nice thing because I you have school in Philly, and there was the Amtrak train which is the fast train that would get you to the New York in an hour and a half. And then there was like the Securitas New Jersey Transit train, which was like a fraction of the price and got you there in two and a half hours. So anytime I ever went to New York because of course, you know, I had to find a way to pay for it. I was always taking the New Jersey Transit and having to change a bunch of times. And this time, I got to go on Amtrak. So I'm really a big deal at this point in time. And I go up and you know, my intention is to just kill it and you know, see if I can get past these rounds so I can get out to San Francis. Go. And I meet this incredible woman at the pier hotel. You know, it's like super glamorous and she's got this suite. And we sit down, we talk about the firm and I do my my song and dance, not the one from the pageant, the one from Wharton.

Keith Conrad 10:17
You actually did have to have a talent.

Carol Roth 10:18
Yeah, exactly. It was funny because there's something that you do when you're an investment banker called modeling, which is, you know, in Excel, you build a financial model. And then there's also modeling like as in the pageant, so there was a lot of confusion between like, can you build a financial model or can you walk down a runway so I don't know the whole thing just got like, blended up in my head. So I meet this woman, I kill the interview, and she loves me. Thanks, I'm great and a great fit, and go back and this guy, his name is Mark salzgeber. He's very impressed and he said, Fine, and then we had a phone interview at his Like, okay, we're gonna bring you out to San Francisco and like, yes. Okay, I finally got my free trip. So they bring they made that's what they do they bring me out to San Francisco. And you know, I'm the kind of person is like, I'm not gonna dial it in, like, if he's paying for it, I'm gonna, I'm gonna give my best effort I'm going to go through, I'm not going to be a jerk about it. And you know, I always keep my mind open, but you know, I go goldman sachs and Morgan Stanley and JP Morgan, like, whatever. So I get to San Francisco and then the funniest thing is I hate San Francisco. I think it's just not me. I know there are a lot of people who love San Francisco but I'm like, this is not nice. Like this is not like I know everyone thinks is charming. I don't like charming like, this is not my thing. I'm a city girl. I'm from Chicago. I went to school in Philly. I spent time in New York like, live like okay, but whatever. I've been here Yay. So then I have my day of interviews. And I go through and I'm meeting all of these amazing people and people who were former Olympic athletes, and just the really cool people on there working on all this cool stuff in their meritocracy. And as I'm moving further and further into the day, I'm like, Oh my god, I really like this. And by the time I was done, they made me an offer to work at Montgomery securities. And as I weighed all of my choices, I'm like, even though I hate San Francisco, I actually work at this place, and ended up making that the home of my career where you know, I got cut my teeth, I met my husband and it sort of set me on this path of success. But the only reason that I even like had the opportunity to end up there is because I was trying to scam a free trip, and then like, jumped through all these hoops of like, pageants and whatever To get my free trip, but having The Open Mind allowed me to capitalize upon that so yeah just never know. And that's my story of how I landed at Montgomery securities.

Keith Conrad 13:12
So important life lessons there if you can't afford a vacation just try to get a job interview they'll pay to fly you out Yeah, so that that's a good thing. Yeah, that's that's a good life lesson. right that's a positive and I guess just be open to any experiences that come along.

Carol Roth 13:30
Yeah, I think there are a bunch of I think first of all persistence you know that there are a bunch of people who when somebody told them no the first time well first of all, they're a bunch of people would never ask the question because it's so ridiculous but I have no shame so that you know, we could that went down but then you did. The persistence is that a lot of life is just being the person who's gonna knock on the door 17 times and finally, a guy's like, okay, whatever. And like you said, keeping an open mind because even though that wasn't your intention or your strategy, it may actually be the best thing. For you, so lots of good lessons. Also, if you're gonna be in a pageant and you're more of a smart person, then Miss America is more for you than Miss USA. So that's enough. So this this one was chock full of life lessons.

Keith Conrad 14:15
Well, thanks so much for sharing your story, Carol.

Carol Roth 14:18
My Pleasure.

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