#236 - Hospitality Meets Simon Casson - The Boy They Called a Failure

To watch this episode, head to https://youtu.be/tMghGC2VZMo

This week, we’re in one of the stunning bedrooms at Corinthia London, talking to a man whose story genuinely feels like a film.

Simon Casson, now CEO of Corinthia Hotels and former President EMEA at Four Seasons, was once told at 15 that he was a failure, that his education was over, and that he should “learn to fix cars or join the army”

He went home devastated. His mum came back from a bar shift, wrapped her arms around him and said:

“Simon, you’re special. You’re going to be a leader of men. You’re going to achieve great wealth and success. And I believe in you”

From washing dishes and sleeping in a room above a local restaurant… to becoming the youngest GM in Four Seasons… to running 45 hotels and 17,000 people… to now leading Corinthia’s push to “challenge luxury’s usual suspects” - this is a story of belief, graft, failure, and a very people first kind of success.

In This Episode

1. “You’re a failure” at 15 – the careers officer, the crushing conversation, and the one sentence from his mum that changed everything
2. Dishes, cheap digs & cheap labour – washing up, living above the restaurant, then a “management training scheme” that was really just doing every job in the hotel (and secretly the best education imaginable)
3. Castles, chefs & the Four Seasons bug – being spotted by Kit Chapman at The Castle at Taunton, working alongside a young Gary Rhodes, and being introduced to Four Seasons as “the greatest hotel company in the world”
4. From managing to leading – the early disaster as Room Service Manager at Four Seasons London and the moment it all changed
5. Washington, Doha, Dubai & beyond – Clinton era D.C., meeting heads of state and celebrities, becoming the youngest Four Seasons GM in Doha, opening hotels in the Middle East and Africa, and eventually becoming President for Europe, Middle East & Africa
6. Sacrifice, anxiety & imposter syndrome – missing chunks of his kids’ childhood, hiding the fact he had no degree, and learning that pressure, doubt and growth often live in the same room
7. The “second mountain” – stepping away after 35 years at Four Seasons, retreating to a farm in Croatia, and then being courted by global brands before choosing Corinthia as the place to write his next chapter
8. Corinthia’s new chapter – why London was transformational, how New York became “the star of the Met Gala”, and what it really means to be a “true contender” in global luxury

Stand-Out Quotes

“When the whole world’s saying, ‘No, you can’t,’ you really just need one person to say, ‘Yes, I believe in you. You can.’”

“We’re all masters of our own destinies. We all have to polish our own diamond.”

“Leadership has to be rooted in humanity. It has to be rooted in kindness. It has to be anchored in really caring about people’s stories.”

“The absence of criticism is not the same as the provision of support.”

“You’re refined in that fire of defeat and failure and self doubt. Or you’re not. Or you fail”

“It’s about getting comfortable with the imbalance, that work is life and life is work”

Why Listen

This isn’t just a “big job” CV walk through.

It’s:

1. A proper origin story about how one conversation can change a life
2. A masterclass in leadership, learned the hard way through walk outs, self doubt and getting it wrong first
3. A peek behind the curtain of Four Seasons in its golden era and Corinthia in its challenger era
4. A very honest take on success, sacrifice, mental health, ambition and reinvention

If you’ve ever felt “not academic enough”, worried you’re an imposter, or wondered how people at the very top actually think about leadership and life… this one is for you.

Frankly, there's something for everyone in here.

Show Partners

A big shout out to the first of today’s show partner, RotaCloud, the people management platform for shift-based teams.

RotaCloud lets managers create and share rotas, record attendance, and manage annual leave in minutes — all from a single, web-based app.

It makes work simple for your team, too, allowing them to check their rotas, request holiday, and even pick up extra shifts straight from their phones.

Try RotaCloud’s time-saving tools today by heading to https://rotacloud.com/phil

Also, a massive shout out to our new show partners Apron

Running a hospitality business means juggling endless payments - from suppliers to staff - all while keeping cash flow in check. That’s where Apron helps.

With Apron Bill Pay, you can manage every supplier payment in one place, approve and schedule bills, and sync automatically with Xero or QuickBooks.

And with the Apron Card, your team can spend easily while you stay in control - and earn rewards on every purchase.

Learn more at getapron.com.