Meet Stephan Dyer — the Costa Rican-Canadian stand-up comedian, keynote speaker, and comedy coach redefining what it means to take a leap of faith. ✨
Born in Costa Rica and based in Toronto, Stephan was climbing fast in the corporate world, becoming one of the youngest senior managers at Scotiabank. The corner office, the title, the paycheck — he had it all. And in 2017, he walked away from every bit of it to chase a life on stage as a professional comedian. 💼➡️🎤
Since then, Stephan Dyer has performed over 2,000 stand-up comedy shows across 13 countries on 4 continents, delivering his bilingual brand of clean comedy in both English and Spanish. From Just For Laughs to Comedy Central, from TEDx Talks to The Second City, his comedy travels — and so does he. 🌍
But Stephan didn’t stop at the microphone. He co-founded MalPensando, the first and only bilingual Spanish-English comedy and public speaking school in Canada, helping thousands of students find their voice through humor. His corporate comedy workshops have reached 50,000+ professionals worldwide, with global clients like Coca-Cola, Uber, Ernst & Young, and TELUS trusting him to bring laughter into the boardroom. 🌟
What makes Stephan Dyer stand out in the world of stand-up comedy? He’s clean, he’s sharp, and he’s a master at connecting with diverse audiences across cultures and languages. In 2021, he landed on the cover of Toastmaster Magazine — the world’s largest public speaking publication, distributed to 364,000+ readers in 143 countries. 📖
This week, The Comics Unseen sat down with Stephan Dyer for an exclusive interview about quitting the corporate world, performing stand-up across continents, building a global comedy school, and why he believes anyone can be taught to be funny.
The Interview With Stephan Dyer
Question: One of the youngest senior managers at Scotiabank calls it quits to pursue stand-up comedy. What was the moment when you knew stand-up was your career?
Stephan Dyer: August 20, 2016. I had been bombing for two years straight until I took a stand-up course at The Second City and started studying joke structure—setup, punchlines, tags. We did a show in London, Ontario, and for the first time… I killed. My friend Juan killed. Our friend Jose killed. After two years of silence, everything clicked. I couldn’t sleep that night. That was the moment I knew I wanted to do this professionally.
Question: You’re a multilingual comic performing in English and Spanish. Have translations ever bombed, or do you keep jokes separate?
Stephan Dyer: Yes—many translations bomb. Some jokes simply don’t survive outside their culture. There are nuances in Spanish, especially within Latino culture, that don’t translate. Now I’m very intentional: I only translate jokes with universal premises and strong structure. If a joke is “culture-proof,” it works in both languages. If not, I keep it separate.
Question: You’ve cracked the corporate comedy market. Is it harder because it has to be “clean”?
Stephan Dyer: There’s definitely pressure—you avoid topics like sex, politics, religion, and profanity. But if the material is authentic and well-written, it still works. The advantage is that corporate audiences usually haven’t seen you before, so strong material has a long shelf life.
What really elevates corporate shows is customization and interaction. I send a questionnaire beforehand to gather insights—company culture, inside jokes, challenges. That alone can generate 10–12 minutes of personalized material. Then we layer in improv and audience interaction, sometimes bringing employees on stage. Structurally, it becomes a dynamic show with multiple segments, which keeps energy high and reduces risk.
Question: How do you create your set? Is it structured or more natural?
Stephan Dyer: Very structured. I typically start by introducing myself, then go into 3–5 bulletproof one-liners. Then crowd work early—within the first five minutes—followed by longer bits (1.5 to 4 minutes each).
I often organize material chronologically because it’s easier to remember and feels natural to the audience. If something interesting happens before I go on stage, I might open with crowd work instead.
In longer sets (40–60 minutes), if crowd work is hitting, I’ll ride that wave. The key is curiosity—you have to approach the audience conversationally, not like you’re forcing a joke.
Question: Your organization teaches people to be funny speakers. Can humor really be taught?
Stephan Dyer: Yes—because it’s a skill. We’ve helped over 800 professionals become more confident and funny speakers. Interestingly, extroverts often struggle more because they resist feedback. Introverts tend to do better—they listen, implement, and improve quickly.
We teach 20–25 communication techniques and 13 joke structures. Combine that with repetition and writing, and most people can build a solid 5-minute set in about seven weeks. Once they’ve performed in front of 50–100 people, speaking at work becomes easy. If structure is teachable, then humor is teachable.
Question: What was your most horrible night as a stand-up artist?
Stephan Dyer: 2018, Guadalajara, Mexico. I had quit my job the year before and was touring. By coincidence, my dad was in the audience—it was his first time seeing me perform. And I bombed. Hard.
Given the context—quitting a stable career, taking a big risk—it felt humiliating. But I also knew that if I stuck with it, the story would get better. Today, my dad is one of my biggest supporters. I even dedicated a show to him for his 70th birthday in El Salvador. That moment aged well.
Question: Who are your stand-up idols? Who do you look up to and why?
Stephan Dyer: Brian Regan and Hannibal Buress—I love how they approach SPORTS topics with originality. Love them.
Adal Ramones was the first person I saw doing monologues on TV growing up. That had a huge impact on me. Performing alongside him one day would be a full-circle moment.
And my brother, Kurt Dyer. He quit his corporate job long before I did and showed me this path was possible. He put me on my first stages over 20 years ago.
Question: You’ve been performing for a while, you have enough material, and yet you’re not chasing specials and are helping others learn comedy. How do you feel about it?
Stephan Dyer: I still feel like I have so much to learn. I’ve recorded three comedy specials, but I approach this as a business. Right now, my priority is creating content that gets people into seats—that’s what allows me to do this long-term, which is what I love.
It also allows me to tour and take my family to incredible places. I will record another special in the next year, but I’m not in a rush. I’m happy where I am—especially after the past year, being invited to festivals like Netflix Is A Joke Fest and Just For Laughs, which were once dreams that felt very far away.
Question: Which comedians are catching your eye right now? And what advice would you give to aspiring comics?
Stephan Dyer: I’m really inspired by Latino comics right now. Marcello Hernández is someone I’d love to perform with—we have a lot of mutual friends. One of those friends, Angelo Colina, is absolutely killing and selling out everywhere.
I also really like Geoffrey Asmus—super original—and Francisco Ramos, who I’ll be performing with at Netflix Is A Joke.
My advice: don’t try to do everything in one year. Most of the outcomes you want will take 10–15 years. Be impatient with action, but patient with results.
