Miss Simpson: A Teacher Who Changed His Path

Mo Gilligan started out working in retail (think Jo Malone and Levi’s) but quit in 2018 when his online comedy videos went viral. The leap paid off - sell-out tours across the UK, a late-night entertainment show on Channel 4 and his own breakout format The Lateish Show with Mo Gilligan, which earned him the first of three BAFTA wins. Netflix specials, world tours, primetime TV and a podcast soon followed.

Now in 2026, Gilligan is launching the biggest year of his career to date with a global tour, a major new partnership with Netflix and a feature documentary which will offer a glimpse behind the scenes of the 37-year-old at the top of his game.

In this episode, Mo opens up about being a dad to his six-month-old daughter and two-year-old son, the pressure of representing the Black British community in stand-up and the debt that shadowed him for years.

✨ IN THIS EPISODE:

00:00 Introduction

03:51 Retail Experience and Its Influence

06:11 Audience Interaction and Respect

09:13 School Struggles and Dyslexia

18:14 Family, Fatherhood and Financial Lessons

25:19 The Standup Struggle

26:37 Credit Card Chaos

31:12 The Viral Breakthrough

33:35 Touring Triumphs and Tribulations

36:04 Code Switching and Representation

39:43 Handling Success and Praise

45:51 Family and Future Plans

💬 QUOTES TO REMEMBER:

I really wanna make people feel cool. I think it’s the nicest feeling ever.

Knowing that I am my children’s universe... That is such a gift that I didn’t know I needed to have.

I find it hard to listen to praise about myself. I find it very, very hard... I'm always trying to move on to the next one.

🔗 LINKS + MENTIONS:

Get Mo’s tour tickets here: mogilligan.com/mo-live

Mo’s new Netflix show is available to watch now: Mo Gilligan - In the Moment

Join the How To Fail community: https://howtofail.supportingcast.fm/#content

Elizabeth’s Substack: https://theelizabethday.substack.com/

📚 WANT MORE?

Ashley Walters - on growing up fast, struggling with self-destruction and how accountability, therapy and fatherhood helped him rebuild his life and career. Fun fact: Ashley and Mo both went to the same school and had the same inspirational drama teacher! swap.fm/l/ksDRiLDV1iOXHRTTsdJ5

Miranda Hart - on public embarrassment, private anxiety and chronic illness. Plus: how learning to accept herself became her greatest success swap.fm/l/oTScN30b80GflJtO4rgu

Fern Brady - another stand-up who has experienced the precariousness of the industry and battled debt early in her working life swap.fm/l/cmeompBv7EHK20enmwbS

💌 LOVE THIS EPISODE?

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Elizabeth and Mo answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content

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Production & Post Production Coordinator: Eric Ryan

Engineer: Matias Torres

Assistant Producer: Shania Manderson

Senior Producer: Hannah Talbot

Executive Producer: Alex Lawless

How to Fail is an Elizabeth Day and Sony Music Entertainment Production.

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