IS IT HOT IN HERE OR IS IT JUST JESSIE?

Meet our February Boss Babe!

Jessie – thank you so much for being our February Boss Babe of the month, and arguably our most risqué (perfect timing for the month of “love”). You recently left your 9-5 to pursue your own entrepreneurial path – Can you share with us what you do and why you started?

I am always happy to be the most risqué woman in the room! ;) I do a few different things! I am the host and producer of the spicy and hilarious podcast, Your Place or Mine. This podcast covers self love pep-talks, steamy stories, and the ridiculousness of nonmonogamous dating life here in Toronto. I am also a stand up comedian, and in 2021 began hosting and producing my own Your Place or Mine themed comedy shows here in the city.

 

The podcast started as a bit of a pandemic project. Years and years ago I had a spicy and anonymous blog that detailed my sexual adventures. At the time, I was married and my husband and I had recently opened up our relationship, and this blog talked about a long term monogamist's journey into the world of sexual promiscuity. I had so much fun writing it, but didn't keep going with it. I considered bringing it back in 2020 with some extra time on my hands, but I wasn't personally reading blogs for pleasure anymore so it didn't make sense as a medium. I've always been a talker (read: loud and the life of the party) and a storyteller, and had some aspirations of work in some sort of broadcasting. The closest I got to that in the past was creating the in-store announcements for Sears in the early 2010's! The idea of starting a podcast seemed like both a fun project and a really cool way to be louder about the things that are important to me. 

 

I've been called loud more times than I can count. This podcast and my comedy shows have given me the opportunity to not only continue to be loud and take up space, but to feel really fucking great about it. Self love, sex-positivity, and body-positivity are the three main pillars I'm passionate about, and as a confident and curvy woman... I've got some pretty great stories.

 

So, the podcast was born, with the first few episodes launching in November of 2020. After having a bunch of my favourite local comedians on the show, it seemed a natural next step to take a comedy course to learn a bit more about the craft. The course turned into trying out some open mics. Open mics led to booked gigs. Booked gigs led to hosting and producing my own shows. This all happened in the span of 5 months. Talk about a whirlwind!

What motivated you to quit your job and put all your efforts into “Your Place or Mine” and your comedy?

In December of 2020 I had the honor of being selected as one of the models for NOW Magazine's Love Your Body 2021 issue. This was an issue I looked forward to every year, sharing the stories of people learning to love their bodies and then posing in the nude. I had spent a lot of 2020 focusing on my relationship with myself and my body. I took a break from dating, spent a bunch of time in therapy, and got to a place with my sense of self that I hadn't quite experienced before. Having the opportunity to be photographed by an incredible photographer (shoutout to Samuel Engelking), completely naked, while feeling more comfortable in my own skin than I ever had before was pretty fucking amazing. 

 

Then the issue launched, thousands of people saw me naked both in print and on the internet. I was flooded with positive comments and love from friends and family and was flying high. Not long after, I got a meeting invite at work and was told that if I was going to post content like that online that I needed to ensure my coworkers or clients couldn't find it. I was instructed to go through and block anyone who could potentially search for me and ensure no one would accidentally stumbled upon these pictures. 

 

My first thought was one of acceptance. It made sense, the company was trying to run a business. I was on our company's social media and having me connected to that and also being naked on the internet was tricky. Then, I cried like 6 times that day. Turns out having one more man tell me to cover up and quiet down made me realize why I did the shoot in the first place. 

 

I don't hold any ill feelings toward my former employer, I worked there for two and a half years and they were good to me and paid me well. But it made me realize that if I was going to continue to be loud about the things that are important to me, it's going to piss some people off. Having to continually censor myself because of the looming fear of my personal life and professional life crossing lines just became tiring. I was on the podcast and on stage talking about the importance of living life authentically, only to show up at a job where I couldn't be my true self.

 

So I saved up my pennies, bided my time, gave 6 weeks notice and finished up at the end of December and damn, it feels pretty fucking great. I'm not at a place where I can do comedy and the pod full time, so I'm currently interviewing with a dream brand that I already work alongside. This would allow me a part time gig that is aligned with my own values to help pay the bills as I grow Your Place or Mine and it's ever-expanding opportunities. 

 

Do you have someone or something that has inspires you?

I was going to loads of comedy shows before I started all of this, and I pull a lot of inspiration from hilarious comedians I've seen over and over. Toronto is chock-full of incredible talent who are hilarious on stage and write on some of my favourite television shows. I could name 30 but I'll shout out Allie Pearse, Sam Sferrazza, Fiona O'Brien, Adam Christie, Natalie Norman, John Mostyn, Dan Udy and Steph Neale. The talent in this city is wild, if you're not going to comedy shows in Toronto you're missing out.

 

I'm also blessed to have some absolute powerhouse babes in my corner. Friends who've been with me through the darker chapters and are now celebrating with me on the highs, I couldn't keep all this up without their support. You babes know who you are. I'd say I'm lucky to have so many strong women in my corner, but it's not luck. I work very hard to make great women around me feel uplifted, empowered, and supported, and that will continue to be a priority for me. 

What challenges have you had to overcome at the beginning of your journey?

I feel like I got a lot of the real, big challenges out of the way in the first big chunk of my life. I had a super rough childhood that involved a messy divorce, a parent with an alcohol addiction, and then was bullied really badly. I've lost and gained a bunch of weight, and have been 50lbs lighter than I am now, and also 50lbs heavier than I am now. I've experienced big love and big heartbreak, marriage and divorce. All of this has turned me into a pretty fucking resilient human. So to be honest, this current Your Place or Mine journey has been a fairly smooth road. I know I'm still in the beginning, and more challenges are coming, but I'm better equipped to handle what comes my way because of my journey thus far. The biggest challenge is 100% impostor syndrome. When I started the pod I had a moment where I messaged my two closest friends and said, "I'm about to drop $600 on podcast equipment. People will actually listen to this right?". And people are listening. A bunch of people, and they keep coming back, and it's really fucking great. 

What do you think is unique about your business?

Probably how much I talk about sex. 😅 In all seriousness, being a plus-sized, polyamorous woman who is in love with her body even though society doesn't want her to be definitely sets what I'm doing apart. I'm not ashamed to talk about enjoying sex, I'm a hedonist at heart. Women are told their entire lives that we're not worthy of enjoying pleasure and that is fucked. Talking about my own indulgent sexual adventures and self-pleasure shows other women that we're allowed to enjoy this. Making jokes about this on stage shows that this is a normal part of life. A lot of people get pissed off to see a plus sized woman enjoying her body and I love that. I spent 8 years in the fitness industry completely destroying my sense of self. Now that I've climbed my way out of the rubble, turns out there are a lot of other women who need to heal. And maybe it's cheesy, but laughing about this shit truly heals. 

It takes a lot of self awareness and confidence to do what you do and share aspects of your personal life with the world. How do you work through any negativity that might come your way?  

I'm definitely in a place right now where overall negativity is fueling me in a positive way. Having more opportunities to be loud about what's important to me is really empowering. It means when negativity is thrown my way, I'm better equipped to handle it. Does it still suck? Totally. I've realized that facing negativity is always going to feel a little bit like shit. Realizing that you're allowed to sit in that hurt and that pain for a little bit in order to process it and move on is important. Sometimes having a good cry and then journaling it out is the right move. Being loud and confident definitely doesn't mean that bad energy doesn't impact me, and some days are easier than others. But I've gotten really good at noticing when I'm not doing okay, and doing the right things to keep my cup full. Oh, and sometimes you just need to smoke a bunch of weed and drink some wine with your girlfriends and watch bad tv. That's also an important form of self care. 

What piece of advice would you give other aspiring female entrepreneurs?

Don't underestimate the power of networking. When my husband and I separated 6 months after we moved to Toronto, I didn't know anyone here. I just started taking myself out and got to know the names of people who worked in my area. I started supporting local businesses and creators that were doing interesting things. I remember people's names, I mention their names in rooms when opportunities arise, and that energy comes back to you. If you focus on growing meaningful connections with as many people as you can, even in micro-connections with acquaintances, people remember you. 

If your life were to be turned into a movie, what would it be called and who would play you as leading actress?

I've been told I look a bit like Reese Witherspoon by like 5 different people, which I find hilarious because I don't see it. I'd probably go with Amy Schumer, maybe Rebel Wilson! I feel like this is like a 10-15  year plan, so it would be really cool if a local comedian made it big in the acting world and she played me, whoever she may be. As for a title. I have aspirations to write a book about my journey of becoming a sex-positive woman comfortable in her own skin and call it "The First Hundred", referencing the first hundred men I slept with. The idea that a woman is allowed to sleep with a hundred people is baffling for so many, and I think women everywhere would come and see that movie. 

Instagram: https://www.instagram.com/jessie__olsen/

TikTok: https://www.tiktok.com/@jessie__olsen

YouTube: https://www.youtube.com/channel/UC4nQW_nGeC531gpVGT82_Lw?sub_confirmation=1
Website: https://www.baesavage.com/

Facebook: https://www.facebook.com/yourplaceormineTO
Spotify Podcasts: https://open.spotify.com/show/6O8R4JluNeGa9iPfqezxAf
Apple Podcasts: https://podcasts.apple.com/ca/podcast/your-place-or-mine/id1536752936