Wealthsimple is a whole new kind of investing service. This is the latest installment of our recurring series “Money Diaries” where we ask interesting people to open up about the role money has played in their lives.

I honestly don’t care that much about money. More money, more problems. I was happier when I didn't have any money.

In 2003, I was living in Astoria, Queens, and getting fired from all my waitressing jobs. I remember eating scoops of peanut butter for lunch. And always having that feeling of playing the lottery going to the ATM: like, is anything going to come out of the machine? I had a philosophy back in those days that I would have no loyalty to any restaurant that I was working for because I wanted to be an actor. So if I had an audition and my restaurant manager said, “No, you can't go,” then I would just quit or I would just go to the audition and get fired.

So I cycled through a lot of different restaurants. I was a cocktail waitress in a bowling alley. I was a cocktail waitress in a wine and tapas bar. I was a barista. You name it. But I was good at it — waitressing, I mean. I was good at getting fired, too, I guess. But I was good at getting tips, making money. My waitress philosophy was: always be thinking about tips. So I would give a lot of free drinks, stuff like that. So the patrons loved me, but the managers didn't.

I got fired from a tapas place on 54th and Lex called Divine Bar. It’s probably not even there anymore. It wasn’t good. They actually paid me to leave because I accidentally tripped a busboy down the stairs. It was an accident! It was New Year’s Eve. Leave it at that…

I had a really crazy first big break. Judd Apatow kind of picked me out of nowhere based on a tape that I'd sent in to him for a movie called Funny People. He said, “We're going to fly you out to LA and do a chemistry read.” So I went out to LA and in four days, I got Funny People, Parks and Recreation and a movie called Scott Pilgrim Versus the World. So it happened really fast. And I was living in Queens at the time and I had just been fired from the job where I tripped the busboy over down the stairs. So I never made the choice to move to LA. I just went one time and then I just never went back to Queens. Things just kept happening.

You want me to talk about my dad? He's a wealth management financial advisor for Merrill Lynch. He used to be a stockbroker. He worked his way up like Wolf of Wall Street style, you know? His parents were both born in Puerto Rico, but he was born in Philadelphia, where most of my Puerto Rican family still lives. My parents were both poor. My dad grew up in a really bad neighbourhood in Philly and my mom grew up really poor in Delaware.

My mom got pregnant with me when she was 20. I was a big surprise. When I was born, we lived in a one-bedroom apartment and I was in a crib and they actually slept on a mattress on the floor. But they both are kind of insane, how much they worked — like my mom put herself through night school, worked her way up. She's a lawyer now.

At one point, my parents were both working at the Wawa. You know Wawa’s? My mom was a manager and my dad was like the checkout guy. And my dad did all kinds of things to work his way up. He was selling books door to door, he was a taxi driver in Philly, he was all kinds of things. And he didn't even graduate from college. But he’s like a real salesman. He's very charismatic, very handsome. Likes to party, like me. He's like this crazy Puerto Rican hanging out with all these old, rich white guys in Delaware. Playing golf with them and telling them what to do with their money. He’s really good at it. I think that's why he’s so good at what he does, because he knows there's a value in not growing up with money — he understands something else that those people don’t.

I don't know what he does, actually, honestly. He doesn't ever seem to go to work.

I always just kind of live my life like I always used to when I didn’t have any money. The difference is now I buy fancy almond butter.

The irony is my dad didn't actually teach me anything about money. But, maybe I shouldn’t say that. I mean, he helps me with some of my money. He’ll say, “Hey, there's this new thing you should invest in.” And I don't know what he’s talking about, but if it sounds good, then sometimes I'll go, “All right. You can have a little bit of it.” But I'm very conservative about this because I think he takes a lot of risks. So, I try to trust him.

My dad is really obsessed with Roth IRAs. He calls me babe. He's like, “Babe, I got a really good idea for you. You got to listen to me. You're going to put your money in a Roth IRA and you’re going to just keep making money.” He calls it a tax shelter. It’s all about keeping your money in the Roth IRA so that when you're 59, you have all this money that's tax-free and then you can just take money out. And it’s basically like the government's money is working for you, you know, in whatever, in that cloud.

All I know is I have a Roth IRA, I have a SEP account because as an actor, I'm a business. My dad was saying it’s all about trying to save that money now so that when you're old you can maintain your lifestyle and not freak out and not have to work until you're really, really old. You know what's funny about the Roth IRA? When I was in high school, I actually worked on [Delaware Senator and Roth IRA namesake] Bill Roth’s campaign when he was an incumbent. RIP.

I wanted to give my dad a head’s up before talking to you so I'm like, “What do you think about this thing [Wealthsimple]?” And he said, “What do I think about it? This is my competitor. These companies are basically saying you don’t need people like me. You can have this robot basically tell you what to do with your money.” I talked to my dad this morning about it.

This is the most I've talked to my dad in like 20 years about this. But the positive thing he said was that for young people that have a certain amount of money but don’t have the minimum requirement for people like him — because he manages old, wealthy, weird rich people in Delaware that have, you know, DuPont money, big bags of cash in their, like, weird Foxcatcher dungeons that they keep. He said that these kinds of companies are really great for young people that don’t have the crazy amount that would make sense to hire someone like my dad. It’s good for people that don’t know what to do with their money — an easy, kind of safe way to make the money you have make more money. He told me that people are living longer. And my genes are good because I've got half Puerto Rican blood running through my body and my people live long.

No wrinkles either.

My favourite thing to do is not cash cheques, just forget them until it’s too late. I don't know what it’s about, honestly. The cheques don’t seem real to me. When I look at them, I'm like “This can't mean anything.” Some of my cheques go to my accountant. He opens them, I guess. Sometimes I do think, wow, am I going to be one of those people that wakes up one day and finds out all the cheques were going to some person that was then stealing half of it?

But, you know, I can't worry about that because life’s short. I always just kind of live my life like I always used to when I didn’t have any money. The difference is now I buy fancy almond butter. But I still eat it out of the jar.

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