Tranna Wintour is a spiritual, pop-culture-obsessed, fashion-hungry, transgender comedian, singer, producer, and writer. She’s basically Barbra Streisand minus the fame, fortune, and cloned dogs. On stage, Tranna brings a unique and rare mix of wit, glamour, and depth that always leaves audiences wanting more. She’s been named by Fashion magazine as one of the queens of Canadian comedy, and CBC Comedy just placed her at the top of their list of top comedians to watch in 2019. In addition to her work as a performer, Tranna co-hosts and co-produces CBC Podcasts’ Chosen Family with her creative partner/comedy soulmate, Thomas Leblanc. Chosen Family reached the top 10 of iTunes Canada’s top comedy podcasts and was named one of Apple’s Best Podcasts of 2018. Tranna will release her debut (musical) album, Safe From Your Affection, this fall on Oscar St. Records. Upon seeing her solo show in New York City, legendary comedienne, Sandra Bernhard, proclaimed: “A star is born!”
More on Chosen Family:
Montreal comedians Thomas Leblanc and Tranna Wintour shine a light on the intersection of art, community and sexuality. Join Chosen Family every other week for deep and spontaneous conversations featuring renowned artists and up-and-coming creators. Past guests include Margaret Cho, Xavier Dolan, John Cameron Mitchell, Jen Kirkman, Sandra Bernhard, and more! Live shows performed at Just For Laughs to sold-out crowds.
Chosen Family was born out of desire to have deeper conversations that are difficult to have on the comedy stage. It was born of a desire to spark discussion and connection within queer and artistic communities, but the show is open invitation to anyone interested in diving deep and having frank, open discussions.
The first season of Chosen Family was produced independently by Tranna and Thomas in collaboration with the Phi Centre, an arts organization in Montreal. For season two, Tranna and Thomas were picked up by CBC, Canada’s Broadcasting Company (like the UK’s BBC), which has allowed the duo to reach a much wider audience. For this new chapter of the show, Cristal Duhaime was brought on as producer and editor, giving the show a unique and rich sound design. Cristal is also the co-producer of CBC’s Love Me, a storytelling-based podcast about the human need for love in all its dimensions. Cristal is one of the best podcast producers in the industry and has helped taken Chosen Family to a new level by transforming it into a talk show that tells a story.
Chosen Family has reached the top 40 on Apple Canada’s overall podcast chart, and the top 5 of the comedy chart. You can subscribe and listen wherever you get your podcasts!
Questions now closed.
Staff asked this question
4 years ago
How would your approach your guests in sharing the episode? I somewhat feel like its part of the deal but I know its not always on the guests top priority especially higher profile guest. Just was wondering how you would approach that conversation with a guest.
Staff asked this question
4 years ago
Hi Tranna, thanks so much for doing this AMA! You’ve clearly had some great success with your podcast and I’ve to hear your take on what’s made it successful?
replied 4 years ago
Hey Tom, it’s my pleasure! I have such a hard time with the word success. In some ways we’ve definitely been successful, and in others ways we’ve been less successful. The greatest success, for me, has been the way show resonates with listeners. We’ve received really great feedback. I think that success is due to our authenticity and vulnerability. Chosen Family is a talk show, and like any talk show, the hosts carry the show in terms of the way it connects with people. I think this season, especially, we’ve pushed ourselves to share more, to go to more uncomfortable/challenging places. Podcasts are such an intimate experience, so I think that authenticity is everything.
The numbers side of things is so much more complicated. Being features on Apple’s homepage and being listed as one of their top 10 best podcasts (2018) provided major boosts to our numbers. But when you’re not famous, and you’re not on that homepage, it remains an enormous challenge to get the word out on our show and to get people to listen and subscribe.
Staff asked this question
4 years ago
Hey Tranna any tips for how to continuously come up with great episode ideas and content would be appreciated
replied 4 years ago
Hey Skyle! I think it definitely depends on what kind of show you’re doing and the frequency you release episodes. If you’re releasing an episode every week, that is an enormous amount of content, and it’s normal for some to be more compelling than others. You can never go wrong with whatever is currently inspiring you/making you excited. Your passion and interest will be contagious for the listener. I think it’s important to stay current. If you’re doing a culture-based show, find some blogs, twitter accounts, TV shows, that cover what’s going on in your area of interest. Ask your audience what they’re into right now; don’t hesitate to reach out to your listeners. People like to feel involved. Trust your instincts, and don’t be afraid to try out different things.
Staff asked this question
4 years ago
Thanks for coming on Tranna. Do you think there’s many genres of podcast left that don’t have great shows being produced for them? If so, which ones? The true crimes of the world seem to get all the new content, but there must be so many genres still underserved!?
replied 4 years ago
Hey Tash, my pleasure! That’s such a great question. Last I heard there was something like 700,000 podcasts out there right now. I’m not sure what–if any–genres are being undeserved. I have to admit I mostly listen to talk show style podcasts, and I’m not super familiar with all the genres out there. True crime is obviously the biggest one. Something I’ve always wanted to experience in a podcast is a soap opera (I’m sure there must be one but I haven’t come across one). So much of podcasts, especially more narrative/serial podcasts, are basically a return to the days of radio shows before television. Soap operas started on the radio, and I think there’s a way to bring that back in podcast form. But that’s my own personal taste! I think it’s safe to say that every genre is being covered, but I think there’s always room for a new, fresh voice/take/point of view. If ever you’re reluctant to start something because there’s already so much out there, just for it (if you’re passionate about it)!
Staff asked this question
4 years ago
What is your opinion on how long you give your show before calling it a day because of no listeners
replied 4 years ago
Hey Tony, that is such a good question! I think it applies to so much in life, not just podcasts. When do you call it quits? Building an audience is the absolute hardest part of podcasting, and often the most disappointing. I know that for me, this year, it has felt like we’ve done almost everything to build an audience, and it’s still not even close to where we want it to be. It can be so discouraging. But I think as a culture we are too tied up in the end results. We define success by numbers, and that is so limited. When I feel disappointed by our numbers, I remind myself that there are people listening and connecting to the show, and even if there’s just 10 of them, it means something to those 10 people and that’s amazing. I think to know when it to call is quits really depends on what your goals are in doing a podcast. If you’re loving the process, the creativity, if making your podcast excites you, keep going! Do not define the success of your project through numbers. If it’s not what you thought it would be, if you’re podcast is starting to feel like a burden, switch gears, try something new on the show, or just end it. In addition to teaching us to define success through numbers, our culture has also taught us to fear failure. It’s why most of us have such a hard time knowing when to end something; we don’t want to feel like a failure. Ending something that is not working and not bringing you joy is not failing. In fact, ending something that is no longer working for you is a great thing because you will open yourself up to something better that is more worth your time. In more practical podcasting advice, keep in mind that it often takes a lot of episodes before people start catching on. The only podcasts that can be immediate successes are big network true crime and talk shows hosted by famous people who already have an audience.
Staff asked this question
4 years ago
Hi there Tranna any insight on building chemistry with a cohost and whether you even need one?
replied 4 years ago
Hey Mauricio! That is a great question! I have to admit, I’ve always been a bit of a lone wolf, especially when it comes to the creative process. I have always preferred working alone, until I meet someone that I have amazing chemistry with and I feel that excitement at the idea of working with them. But I am SO selective about who I work with. When I met my creative partner and podcast co-host, Thomas, I just instantly knew it was going to work. The chemistry was there. I personally cannot fake chemistry, for me it’s either there or it’s not. If there was a decent pay cheque on the line, I would obviously fake it, but I don’t think genuine chemistry can be manufactured. I think even more important than chemistry is trust, especially if you’re doing a DIY project together. For example, with Thomas, it’s not just about the chemistry we share on stage (or on the podcast); we make money together, we make creative decisions together, we had to hire a lawyer together–working creatively with someone is almost like being married to them. I think there are two ways to go about having a co-host; either you are the sole creator/producer of the show, so you take care of all business/creative decisions and you hire someone to be your co-host and that’s their only job. Or you build something with someone and you’re both equally involved (obviously this way is much more demanding and again, it has to be with someone you deeply trust). And maybe you don’t need a co-host, it totally depends on your style. Jen Kirkman is a comedian and she does a podcast all by herself. It’s just her talking for an hour and it’s hilarious and great. I tried to do that and it didn’t work. I ran out of things to talk about after 5 minutes, because I either need an audience or someone to bounce off of.
Staff asked this question
4 years ago
Heya Tranna in your mind what are the best reasons to get into podcasting? I feel like so many people do it to make money then realize it’s not really a way to do that. I’ve found that the best mindset to have is to treat it as an enjoyable hobby and let whatever rewards come, if they ever do. But interested in getting your take.
replied 4 years ago
Hey Kat, I totally agree! I think in general, when it comes to anything related to the creative arts, including podcasting, the reason you should be doing something is because you have something you need to say; you feel so greatly about something that you need to share it; that you want to communicate with people and create discussions. People who only do something for the money are easily identifiable and very uninspiring, That being said, there is now money to be made in podcasting. It’s becoming/already is a major industry. Many podcaster creators now have agents and they’re selling shows to networks, just like TV. I think we’re still at a point where it’s rare to make money from podcasts. People who aren’t already famous and/or supported by a network who think they can just throw something up on Apple and make money from it are in for a rude awakening. It’s ridiculous to think that everything we do has to be monetized. You’re allowed to do something for the simple JOY of it, and you should! I think going into anything with expectations and a focus on the end results is a recipe for disaster. I think business and hobby are both perfectly fine approaches to podcasts, and the hobby approach is definitely way more fun. I’m going to be doing a second podcast soon that is strictly for PLEASURE and I seriously cannot wait. When your podcast is part of your business, it is seriously hard work.
Staff asked this question
4 years ago
What takes up most of your time with the podcast?
replied 4 years ago
Hey Jess! What takes up most of my time is the research for our guests. Chosen Family features a main interview with an artist every episode, and the research can be very demanding. In our first seasons, our interviews were unedited and basically unscripted. In this season, we’re doing something that is much more involved in terms of sound design and creating something cohesive, so now we basically script out our interview questions (while always leaving room for spontaneity and for whatever comes through in the moment) and that really takes a lot of time. And the second thing that takes quite a bit of time is everything related to marketing and audience building.
Staff asked this question
4 years ago
Tranna, what made you decide to release Chosen Family in seasons? I’m always interested in this format choice!
replied 4 years ago
So each of our episodes has a main guest that we interview for about 45 minutes (it usually gets edited down to 20-25mins), and honestly, booking guests is not easy! We’re quite selective with our guests, and always want to deliver conversations that people will be excited about/learn something from, and I just don’t think there’s anyway we could sustain that kind of quality while going on indefinitely; I think at that point we’d basically be a radio show. With the amount of work that goes into each episode, I honestly can’t imagine doing it without taking long breaks. The new podcast I’m going to start is going to be completely unedited, and much less work intensive, and for that one, I don’t think we’ll have seasons. We’ll just keep going.
Staff asked this question
4 years ago
What are your favorite podcasts?
replied 4 years ago
Hey Susanne! My favorites are:
Two Less Lonely Girls (it’s a podcast hosted by comedians Rosebud Baker and Corinne Fisher; it started off as a Justin Bieber podcast, they’re both women in their 30s obsessed with him, but it’s evolved into a more general pop culture show, but the Bieber episodes are hilarious)
Gay Future (a brilliant, fictional, serial podcast. It’s hilarious)
Missing Richard Simmons (that was the first podcast I really listened to, I was riveted)
Uncover: The Village (I’m not really into true crime in general, but this one was riveting, about a gay serial killer in Toronto)
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Hey Bobby! Great question. It’s honestly something I’m still figuring out. On a personal level, I find it very hard to ask anyone for anything (lol). We’ve had several high profile guests on our show this season who didn’t share their episode, and those feel like very big missed opportunities in terms of reaching new audiences. I understand that people very carefully curate their social media, and so a post about a podcast might not fit into that, but I think that’s what Instagram stories are great for: they’re up for 24 hours, they’re disposable, so who cares what you throw up there? I think ultimately the question of sharing the episode should come up in the booking of the interview, rather than after the fact. When you’re inviting someone to do your podcast, and giving them the rundown of your show, that would be the best place to say “we would also really appreciate it if you’d share the link to your episode when it comes out, I’ll send it to you as soon as it’s available.” I think it’s easier to bring it up then rather than after the episode is released and they haven’t shared it. It’s definitely tricky.