Today Madison sits down for a bold, hilarious, and totally unfiltered conversation with Tiffany Haddish.

Just like Madison, Tiffany is someone who dreamed big early on and is making her success happen on her own terms.

Tiffany went from doing stand-up and grinding through the comedy scene to becoming one of the most recognizable voices in entertainment, breaking through in a massive way with the movie Girls Trip.

Tiffany is also a bestselling author, a producer, and a powerhouse performer who was also the first ever female African American Stand Up comic to host Saturday Night Live.

Madison and Tiffany share so much in common you wouldn’t expect, so tune into 21 Questions now.

21 Questions is made in partnership with Fairmont Hotels and Resorts. This episode was filmed in Santa Monica California at the stunningly beautiful Fairmont Miramar Hotel & Bungalows.

21 Questions is proudly made by by coastal and Project 10.

On this week’s episode of 21 Questions, Madison reflects on friendship, growth, and the people who shape us along the way.

She shares what it was like growing up without a large circle, and how her experience filming the movie Champions helped her build a true group of lifelong friends. At the heart of it all is the importance of having people you can count on. It’s something Madison deeply values, and something she’s committed to creating within her own community, too.

In this episode, Madison and Producer Sylvia also chat about love! And what it means to have a partner who supports you fully, someone who hypes you up, stands by you, and shows up for you on your best days and your hardest ones.

And, of course, there’s music. Madison shares how music is her love language - a universal way she connects with others, often through thoughtfully curated playlists. For her, music isn’t just a passion, it’s a powerful way to deepen relationships and bring people closer together.

21 Questions is proudly produced by by coastal and Project 10 in partnership with @fairmonthotels.

This is the first ever LIVE episode of 21 Questions coming to you from South by Southwest in Austin Texas!!

Madison knows first hand how fun it is to people wrong so today her and Ashley Callingbull are going to talk all about turning adversity into success.

Ashley is an actress, model, host, international public speaker and First Nations activist. She’s done everything from competing on The Amazing Race Canada, to winning Miss Universe Canada, to speaking at Harvard AND being the first ever First Nations Sports Illustrated model.

Ashley is a true change maker. She’s been named Canada’s Top 20 Under 30, the Top 10 Power Women, Indspire’s Youth First Nations Award, the Esquao Awards’ Circle of Honour, a UN Role Model Award, and the Queen Elizabeth II Platinum Jubilee Medal.

Ashley knows that your dreams are worth chasing, no matter what anyone else thinks, and we couldn’t agree more.

This is 21 Questions live from South by South West.

This episode was filmed at SXSW and in the heart of South by Southwest and at the Fairmont Austin.

21 Questions is made in partnership with Fairmont Hotels & Resorts.

21 Questions is proudly made by by coastal and Project 10.

On this week’s episode of 21 Questions, Madison opens up about the challenges and courage it takes to be your true, authentic self.

Madison and Producer Sylvia reflect on what it means to show up honestly, they also celebrate one thing that’s always grounded both of them: laughter. Proud “Gigglers” (shoutout to the Giggly Squad), they share how humour has carried them through even the hardest moments, because sometimes, laughter really is the best medicine.

In this episode, Madison also speaks candidly about her disability, sharing how she navigates support and why she prefers to ask for help on her own terms. For her, there’s a big difference between asking for help and having people assume she needs it.

Madison also reflects on the impact of her speech therapist, who encouraged her to push past obstacles and share her John Legend cover video with the world. That moment helped shape her path, one where she’s become a role model to many. Now, when strangers share how she’s inspired them, it’s a powerful reminder that every challenge has led to something meaningful.

21 Questions is proudly produced by by coastal and Project 10, in partnership with @fairmonthotels.

We’re back with a special bonus episode of 21 Questions, featuring Madison Tevlin and Producer and Director, Sylvia.

In this conversation, Madison reflects on what it was like growing up with a disability. As a child, she didn’t see herself as different, but the world around her didn’t always reflect that same kindness. There were moments when people looked at her differently, or when the energy from others felt off.

As she got older and began to understand Down syndrome, Madison navigated it all with the unwavering support of her parents. What could have felt like a limitation, she embraced as her superpower. This is a perspective she’s shared before, like in her conversation with Nicole in an earlier episode of 21 Questions, about the importance of choosing to live authentically.

By showing up fully as herself, Madison inspires those around her. She reminds people to have more fun and be present. And Sylvia shares that working alongside Madison has been a lesson in exactly that. Because at the end of the day, what people truly see in you is how you show up: with kindness, hard work, and authenticity.

So show up. Have fun. Be present. And if the moment calls for it, don’t be afraid to get up and dance.

21 Questions is proudly produced by by coastal and Project 10, in partnership with @fairmonthotels.

This week Madison Tevlin and Producer Sylvia are back to dive into more behind the scenes of 21 Questions. They talk about the future podcast dream guests (we’re looking at you Reese Witherspoon and Jennifer Aniston), advice for aspiring podcasters, what it was like interviewing Woody Harrelson and so much more!This episode was filmed at the gorgeous Fairmont Miramar Hotel & Bungalows in Santa Monica. Fun Fact - episodes with Kaia Gerber and Jordan Chiles were also filmed here. Be sure to check those episodes out too.21 Questions is made in partnership with Fairmont Hotels & Resorts, by coastal and Project 10.

Today you get to listen to a super fun chat Madison had with Kaia Gerber.

Kaia has been chasing her big dreams since she was a little kid, and she’s made them happen! She’s been modelling since she was a baby and was one of the first models of her generation to be on the covers of the Vogue Big 4.

But her career doesn’t stop there. Kaia has also started her own super successful bookclub Library Science to showcase some of her favourite authors, she’s taken to the stage in live theatre and has been building an amazing acting career in shows and movies like Palm Royale and Bottoms.

Kaia is smart, kind, talented and driven.

This is the power duo you never knew you needed.

This is 21 Questions.

21 Questions is made in partnership with Fairmont Hotels and Resorts.

This episode was filmed steps away from the beach at the Fairmont Miramar and Bungalow in Santa Monica.

Today, I get to share a conversation with two people I’m absolutely obsessed with. Seth Rogen and Lauren Miller-Rogen.

Seth and Lauren have been producing, directing, writing and starring in movies and tv shows for decades. They’re hilarious, hard-working, talented and SO stylish too.

As the founders of Hilarity for Charity, Seth and Lauren are using humor to drive real change in the fight against Alzheimer’s disease. Something that is very close to their hearts.

It’s actually very close to mine too. People with Down syndrome are far more likely to develop Alzheimer’s, so their work means a lot to me and my community.

This is 21 Questions.

21 Questions is made in partnership with Fairmont Hotels & Resorts. This episode was filmed at The Fairmont Century Plaza in Los Angeles. Fun fact, it used to be a studio lot.. Pretty perfect for this episode!