Wealthsimple is an investing service that uses technology to put your money to work like the world’s smartest investors. In “Money Diaries,” we feature interesting people telling their financial life stories in their own words.

I always wanted to do hair. When I was literally, like, a toddler, I talked about it, I was curious about it, I wanted to play with other people’s hair all the time. So it should have been a no-brainer, but it took dropping out of college for me to take it seriously.

After high school, I enrolled at the University of Arizona. I had a partial scholarship for cheerleading and I studied Political Science, but only for a semester. I got a 1.7 [GPA] and was put on academic probation, which kind of sucked, but I never took it super seriously or went back to class after that. You see, The Golden Girls and The Nanny were on from 7 in the morning 'till 1 in the afternoon on Lifetime and that's when all my classes were and that just didn't work for me. When I was kicked off the cheerleading squad and lost the little bit of scholarship I had, my parents got so mad because they were footing the bill for what it didn’t cover. I signed up for a second semester because I thought that was the right thing to do, but then I got real with myself and decided to drop out at the last minute. I pulled out on the final day of the reimbursement deadline, so my mom rushed into town and kicked down the Dean of Students’ door and was like, “We are getting that money back!” And she did. When she showed up on campus I was like, “I can’t do this, Mom. Who am I fooling? I’m not a college student, I’m a hairdresser.”

I grew up in Quincy, Illinois, which is a town of like 40,000 or so people on the Mississippi River. It’s five hours southwest of Chicago and can be described as this rural, cute, little Midwestern farm town. My family was never strapped for cash. I come from the 7th generation of a newspaper, TV and radio broadcasting company called Quincy. After school my mom would sometimes pick me up and I would go back to the paper with her. She was fierce and always working it — when you come from a family business, especially as a woman, you have to work twice as hard for half the respect of your employees. People thought that my mom had it easy and was only given the opportunity because she was the owner's daughter. In reality, she had to claw and fight just like she would have in any other male-dominated business. She’s been on her grind for such a long time.

My dad ran one of the local TV stations. I’m the youngest of four and the only one who didn’t go into the family business. My oldest brother runs an NBC affiliate in Peoria, Illinois; my other brother runs the NBC affiliate in our hometown; and my gorgeous stepsister is a writer and a mom with four kids of her own who are all just super cute.

My parents divorced when I was five. Money had something to do with it, I guess. When it came to budgeting, my dad was tighter than the bark on a tree. My mom, on the other hand, was a big fan of lighting money on fire and throwing it out the window, which I am too. She’s where I get my joie de vivre from, or however that saying goes. We used to drive an hour and a half away to St. Louis together, which was like our own mini metropolis. We’d go to the Galleria, which I guess is like the Midwest version of the Beverly Center in L.A. That was the big thing to do in Quincy. People would drive all that way to just hang out and spend their money and sit in a food court. My dad would never. Like, ever. They were so different in that way.

When my parents split they moved into separate houses. They both remained super supportive of my interests and were really involved. They definitely expressed their worry about like, you know, their son performing a ballet routine in the school talent show and how that would affect me socially. But they still made sure to pay for whatever extracurricular made me happy. I kept busy, girl. I took swimming classes and violin lessons and I did gymnastics. So the divorce didn’t affect me financially so much as it negatively impacted my organizational skills. I was always forgetting something somewhere because I was always dividing my time between two different places. I had a very privileged and extremely lucky childhood, but that part of it was tough. But maybe that's why I grew up to be a bicoastal person? I’m so used to living out of a suitcase. I actually love it now. It makes me feel alive!

My mom remarried when I was nine years old to her sweetheart of all sweethearts and that kind of brought back some balance. He was 11 years her senior and lived three doors down from her when she was growing up. It was so cute. She had a crush on him when she was like seven and he was a senior in high school, which was weird then, but sweet when they reconnected. His family owned an insurance company and he was an investor. He did well for himself until the stock market crashed and hit him really hard. He became a stay-at-home-dad overnight and raised my brothers and I. He taught me how to change a tire, how to fish, how to ride a bike. And if I left the house a mess he’d be like, “Son, you better drop down and give me twenty,” and I’d be like, “Ha! Yeah right,” and laugh at him. And then he’d be like, “I’m not kidding,” but I’d just run into the cornfields so he couldn’t make me.

When my stepdad first moved in, he and my mom attempted a short-lived allowance system for chores, but that went out the window pretty fast. Then they came up with a system where my siblings and I would pay off the stupid things we wanted, but that they didn’t think we necessarily needed. They would never charge us for food or make us pay rent, but anything outside of the essentials we had to earn. So I would basically have to work toward owning the exorbitant things I desired by weeding the garden or mowing the lawn, which I was really bad at. The first time I ever coloured my hair I decided to bypass the chores because I was terrible at using the lawn mower and because I knew they would never let me do it. Instead, I spent months siphoning quarters off of my stepdad’s bedside table until I had the $18 it cost to buy a box of that beautiful Garnier Feria bright red boxed hair colour. I was like 14 and I did it by myself.

When I was 15 I got my first job, teaching gymnastics to kids at a little summer camp that was stationed at the local community college. I did that for a bunch of summers. And then I also worked at my family’s newspaper in the circulation department. That was my second job. I had to deal with customers’ subscriptions and complaints. If a paper didn’t get delivered or was thrown in a puddle, I had to sort it out. It was annoying, but I got paid minimum wage and it was nice to have the extra spending money. I spent most of my paychecks at Bath & Body Works. I was obsessed with self-care things.

After I dropped out of college I enrolled at The Aveda Institute in Minneapolis, but this time I had to pay my own way. My parents were like, “We’re not paying for you to drop out again girl. No, ma’am.” They wanted to teach me a lesson. So I got a job at a tanning salon called Sun Places Tanning Solutions. I worked the front desk and cleaned out the nasty beds… a lot of sweaty, disgusting beds. And I took out a FAFSA loan and did the damn thing. My mom went halfsies on my rent though, which was so very generous of her.

I was also fired from Applebee’s when I was at hair school. I never even finished my training.

When I trained and worked at Aveda, the school charged the clients something like $12 for the services, but the students didn't get any of that money. The school took it all and then the clients would tip the students if they wanted. Sometimes they would tip me a quarter and sometimes it would be a dollar. But then other times the client would be generous and be like, “Aww, you're a little hair school student,” and would throw me $20. The tips weren’t great, and other students had jobs, but my friend Tara and I didn’t want to work after class. So we would just eat Hostess Susie Q’s and those Little Debbie Zebra Cakes and the off-brand wafer bar things that were like 25 cents. I could bring in anywhere between five and twenty-five bucks a day. In a really good week, I’d make about $100, which was just barely enough to get by.

I remember one woman who came in and I had to do a reformation curl, which is where you relax the hair and then you perm it. She was older and looked like she was in a shelter sort of situation. Basically, when the teacher saw her come in and was deciding which student to give her ticket to, he was like, “Who do I hate?” Like, he literally said that out loud. I was standing right next to him and he was like, “Here, Jonathan. This one’s for you.” It turned out she was a retired hairdresser who had fallen on hard times. She was like, “You know, I don’t really wear my hair like this. I just need it for texture. I tease it out to look like Dorothy from The Golden Girls.” So I did it for her, but I didn’t really know how to wrap a perm yet. She walked me through it. She was like, “No, boy,” like, “Wrap that thing tighter! Twist that thing around! Wrap it!” She taught me a lot. And when we were done she tipped me $30, which was more than the service itself. I remember thinking about how everyone in that classroom was so worried about getting that client. But every single one of them would have kicked me in the face for her if they knew about that $30 tip. It was such a life lesson. Be open to experiences.

I was in hair school from 2005 to 2006 and then I moved to Phoenix and did hair there for three years. When my grandfather saw that I had finished school and was working a steady job, he came through in a big way. He had put money away for me and my brothers for college, but he wanted to make sure I was really taking the hairdressing thing seriously before he dipped into that savings. He needed to see that I was being responsible. He paid off my FAFSA loan one Christmas. After that I was cutting hair in Scottsdale for a little bit before I moved to L.A. to work for Sally Hershberger.

I ended up losing my stepfather in 2012. He passed away on their 16th wedding anniversary and that medical bill was either $3.4 or $4.3 million in cancer treatment. I can’t remember which, but, either way, had he not had insurance my mom would never have recovered. Ever since he passed I’ve been constantly worried about getting caught in an unfortunate situation so I make sure I pay that shit on time. I put it on auto-pay. I love Obamacare. I get so mad thinking about the families who have to go through things like that and face the healthcare system without insurance and the politicians who are actively trying to take away those protections. It’s scary.

I worked for Sally Hershberger for two years at that salon. I built myself up until I had a waiting list. I worked out of a salon on Abbot Kinney near Venice Beach and just hustled and hustled and hustled. And during that time I would go back to Phoenix almost every weekend and do all my clients that I built up over the years. And I would practice all of the different haircuts and colour techniques that I was seeing in L.A. and just, like, try them out on these people who trusted me because they had already been seeing me for years. Sally Hershberger paid their assistant hairdressers something obscene like $8 an hour and scheduled us for 15 hour days with totally fake lunch breaks. That salon just rode you really hard. And so I made ends meet going back and forth to Phoenix.

Sally Hershberger charged $35 for assistant haircuts. And then once you got on the floor, it was $150. But you only got 20 percent commission because you were an assistant. Coming up in salons like that makes it really difficult to get ahead. I would even go as far to say it’s nearly impossible. It used to be that you would get a job at a good salon, and after two years you’d get busy. Just like that. But now you have to really work at it. You have to speak your craft. Talk about your craft everywhere. Grab people from the grocery store! Grab them from the mall! From anywhere! Just talk about what you do all the time. That’s how I built quickly. But that was before social media, so I got sick of having to build myself so much. I had to rely on word of mouth. And it worked.

My friend Monique and I both decided to go out on our own, and she’s been my business partner ever since. We co-founded and opened our own studio — MoJoHair — and have been at the same place in L.A. now for a while. The building charges like $680 per week, or maybe like $710 or something. I’m not sure because it goes up every year — just like renting an apartment. It’s not bad. But we also have to pay our assistants and pay for colour, towels, smocks and all of that. So there’s still a lot of overhead. But it’s really nice not having to answer to anyone else. We love working for ourselves, making our own schedules and setting our own hours. And it’s great being able to create our own work environment, as far as music and lighting goes.

When I started working for myself, things were just better, you know? That’s when I got the idea for my Funny or Die web series, Gay of Thrones. My friend Erin Gibson — who is the co-host of this amazing podcast, Throwing Shade — was in my chair and I was doing her hair and I did, like, an accidental high-energy recap of Game of Thrones. We were having a gay old time and she was like, “We need to make this into a thing.” She was a director for Funny or Die and so she pitched it to them and they were like, “Okay. We don’t get it, but okay.” And that’s how it was born. I didn’t get paid for the first season — it was just something fun to do. But then it became this huge hit and we started getting paid.

I actually got hired to groom the cast of Game of Thrones for Comic-Con at the same time as I was filming the first season of Gay of Thrones. It was really random. When I showed up, the creators of the show were like, “Aren’t you that guy who does the recap show online?” and I was like, “Oh, fuck. I’m going to get fired and I haven’t even been here three minutes. They’re going to think I’m some insane fangirl.” But it turned out they loved it.

We’ve since filmed five seasons, have racked up over 47 million views and in 2016 we received an Emmy nomination for Outstanding Short Form Variety Series. We didn’t win. Park Bench with Steve Buscemi beat us. But that’s okay.

Time is money, honey.

Gay of Thrones opened a lot of doors. I actually started doing Margaret Cho’s hair because of the show. I almost crashed my car in the Pacific Ocean when I saw that tweet, because she’s one of my favourite comedians of all time. I can literally recite Notorious C.H.O. from memory because that’s what singlehandedly got me through the 7th and 8th grades. I rented that from Blockbuster almost every weekend. And that led to me doing her hair for Fashion Police for the last two years that was on. And during that time I got to know all of the show’s producers, which then led to me filming a TV makeover moment for E! for the Oscars. Things were taking off.

When it leaked in the press that Netflix was rebooting Queer Eye at the beginning of last year I was like, “Ah, pick me!” I was starting to make a name for myself and just felt like, why not? So I submitted my application to the casting company and hello! She booked it. Like, she did the impossible. I think they had like a thousand reels — a thousand gays for five spots aren’t great odds. It was difficult. They were like, “Come in for this weekend-long chemistry audition where we’ll have you just kind of hang out with everyone,” and it was basically a hundred gays mingling each other to death. It was like being on Fire Island except all of us were vying to be America’s Next Top Model. You can only imagine.

When the boys and I were cast we banded together and made sure we got paid the same thing. I’m really into that part of our story. We’re homies. We’d all feel so resentful if one of us was getting more or less than the others. It would create a very, like, not cool work environment. We film in Atlanta because it’s cheaper to live there and we can do more for the guys we’re making over with less money. And for taxes I suppose. But there’s definitely a cultural piece to it as well. It creates a certain mood and gets us out of the typical LA or New York scene. The guys in Georgia have a different aesthetic too, which makes it interesting.

When I’m not filming I’m still doing hair. I currently charge $250 for a cut. The longer I do hair and the better I get at doing hair the more I can charge. But I do think that the more sought after I become, the supply and demand thing will have to apply. Time is money, honey. When I was younger I felt weird charging people to do something I loved and was passionate about, so I used to do a lot of freebies for friends. But that wasn’t sustainable. I used to barter services too, but that can get murky. I’ll still sometimes barter with photographers, depending on their social media following. A shout out on a major platform costs money. But that’s about it. Now my mom is the only person I don’t charge.

I haven't done any paid sponsorships yet because I just want to make sure that I can stand behind those products and that they're useful and valuable. I have psoriasis, which makes my skin really sensitive, and, because of that, I have to remain aware of what my word means and what it’s worth to other people with sensitive skin. I don’t monetize my bi-weekly podcast either. She’s my little passion project. We’re on our second season and she’s called Getting Curious with Jonathan Van Ness. It's really unproduced and just really fun. I feel like everything I’ve accomplished has been passion-driven and not money-driven, and that’s why I am where I am. But I’m also aware that this industry will chew you up and spit you out if you’re too nice. So I’m trying to find the balance. But how do you put a price tag on something like that?

Right now I’m saving for a down payment on a house. I’m really into the idea of a duplex situation. I haven’t taken the plunge yet, but I think next year is going to be my moment. I’ll invest in a home base after Season 2 of Queer Eye. For now, I’ve treated myself to a pair of gorgeous Jimmy Choo boots and this really fierce, really bold, silly, bright yellow Opening Ceremony jacket that I love. Eventually, though, I want to buy property in the Valley because that’s what I can afford in L.A. I thought about buying in New York, too, but I’d only want to live in Manhattan and I’m not delusional. I don’t want to live in New Jersey or Connecticut or something. That’s not my truth.

I am trying to make smarter decisions now that I’ve got a steady income and have this presence. But I am still a girl who very much likes to shop.

It’s weird, because the more successful you are, the more expenses you have. Like I have a publicist now. That costs money. While I was filming Queer Eye people kept asking me, “Are you ready for what’s about to happen? Like really ready for it?” And I was like, “Yeah. I already have Gay of Thrones fame.” I thought, “I got this.” But I did not get it. I didn’t understand how much my life was about to change. Now I understand.

As told to Maxwell Losgar, exclusively for Wealthsimple; transcript edited and condensed for clarity. Illustration by Jenny Mörtsell.