Former Banker & Master Tailor: PROFF (AskOkey) – Reinvention, Identity, & The Power of Dressing Well

Former Banker & Master Tailor: PROFF (AskOkey) – Reinvention, Identity, & The Power of Dressing Well

The Gstaad Guy sits down with PROFF, the man behind the AskOkey universe, a former JP Morgan investment banker turned tailor, blogger, and one of the most quietly compelling voices in men's style, to explore what it truly means to dress with intention and live with purpose. From the boardroom to the cutting table, PROFF reflects on a life shaped by reinvention, resilience, and the profound relationship between how we dress and how we carry ourselves. The conversation ventures into the philosophy beneath the cloth: the stoicism that steadies him, the desire to grow that drives him, and the responsibilities inherited along the way that forced him to find his footing faster than most. PROFF shares what it means to build something from nothing, why necessity has always been his greatest teacher, and how observation, solitude, and a commitment to becoming the best version of yourself can quietly transform a life. A thoughtful and deeply personal conversation about identity, grit, and the elegance of knowing exactly who you are. Filmed in the One&Only One Za’abeel Royal Suite. (00:00) Intro ✨🎙️ (00:58) Aura ✨🌀 (02:55) Solaro Suit 👔🌞 (05:32) Ask Okey Universe 🌍🙏🏼🙏 (07:49) Public Persona 🎭😎 (09:55) Becoming A Tailor 🧵✂️ (11:58) Audience Engagement 🎤👥 (15:04) What You Stand For 🏛️💪🏻 (17:00) Life Changing Moment ⚡🔄 (20:00) JP Morgan 🏦💰 (26:30) Playbook For Life 📖🗺️ (28:27) Stoicism 🧘⚖️ (30:18) Desire To Grow 🌱📈 (34:18) "Why Am I Doing This?" 🤔💭 (37:40) Spending Time Alone 🌙🚶 (38:49) "The Journey vs. The Destination" 🛤️🏁 (40:49) The Irony Of Life 😏🔄 (43:46) Being Content With Progress 😌✅ (47:35) Family 👨‍👩‍👧‍👦❤️ (48:39) Necessity Is The Mother Of Invention 💡🔧 (53:00) Gentle Guidance 🧭🌿 (53:26) Grit 💪🏻🔥 (57:25) The Greatest Gift Is Observation 👁️🎁 (59:56) Knowing Where You Come From 🌍🏠 (1:02:21) Be The Best Version Of Yourself 🌟💯 (1:05:38) Looking For Knowledge 📚🔍 (1:08:01) À La Poubelle vs. Fantastique 🗑️✨ Learn more about your ad choices. Visit megaphone.fm/adchoices

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Episoder(66)

Founder & Chairman of Cookson Adventures: Henry Cookson – Polar Records, Real Wealth, & the Legacy Question

Founder & Chairman of Cookson Adventures: Henry Cookson – Polar Records, Real Wealth, & the Legacy Question

The Gstaad Guy sits down with Henry Cookson, the polar record holder turned founder of Cookson Adventures, to explore what actually constitutes a life well spent. Henry left a prime brokerage desk at ...

19 Aug 1h 17min

IM8 Co-Founder & CEO: Danny Yeung – Serial Entrepreneurship, David Beckham, & Building the World's Most Complete Daily Essential

IM8 Co-Founder & CEO: Danny Yeung – Serial Entrepreneurship, David Beckham, & Building the World's Most Complete Daily Essential

The Gstaad Guy sits down with Danny Yeung, co-founder and CEO of IM8 and one of Asia's most accomplished serial entrepreneurs, to explore what it truly means to identify a gap in human health and buil...

12 Aug 58min

Design Historians, Authors & Curators: Charlotte & Peter Fiell – Collecting, Watches, Taschen & Why Everything Is Designed

Design Historians, Authors & Curators: Charlotte & Peter Fiell – Collecting, Watches, Taschen & Why Everything Is Designed

The Gstaad Guy sits down with Charlotte and Peter Fiell, the design historians, authors and curators behind Taschen's Ultimate Collector series, to explore what separates objects that endure from obje...

5 Aug 1h 5min

Eight Sleep Co-Founder & CEO: Matteo Franceschetti – Sleep Optimisation, Billion Hours of Data, & Why Recovery Is the Last Frontier of Human Performance

Eight Sleep Co-Founder & CEO: Matteo Franceschetti – Sleep Optimisation, Billion Hours of Data, & Why Recovery Is the Last Frontier of Human Performance

The Gstaad Guy sits down with Matteo Franceschetti, co-founder and CEO of Eight Sleep, the company that has quietly become one of the most powerful sleep labs in the world, to explore what happens whe...

29 Jul 1h 17min

Jaded London Co-Founders: Jade & Grant Goulden – Disruption, the London Look, & Building a Fashion Brand Without a Business Plan

Jaded London Co-Founders: Jade & Grant Goulden – Disruption, the London Look, & Building a Fashion Brand Without a Business Plan

The Gstaad Guy sits down with Jade and Grant Goulden, the siblings behind Jaded London, the boundary-pushing fashion brand that has built a devoted global following by moving at the speed of culture a...

22 Jul 1h 13min

Il San Pietro di Positano Owner: Vito Cinque – Family, Farm to Table, & the Art of Making the Complex Look Simple

Il San Pietro di Positano Owner: Vito Cinque – Family, Farm to Table, & the Art of Making the Complex Look Simple

The Gstaad Guy sits down with Vito Cinque, owner of Il San Pietro di Positano, one of the most beloved and enduring family-run hotels on the Amalfi Coast, to explore what it truly means to build a pla...

15 Jul 1h 13min

Complex CEO: Aaron Levant – Street Culture, the Convergence of URL and IRL, & Why Curation Is the Highest Form of Innovation

Complex CEO: Aaron Levant – Street Culture, the Convergence of URL and IRL, & Why Curation Is the Highest Form of Innovation

The Gstaad Guy sits down with Aaron Levant, CEO of Complex and one of the most conviction-driven figures in modern media and culture, to explore what it truly means to build something at the intersect...

8 Jul 1h 25min

SKIMS Co-Founder & CEO: Jens Grede – Timelessness, the American Dream, & What It Really Means to Make a Simple Product Great

SKIMS Co-Founder & CEO: Jens Grede – Timelessness, the American Dream, & What It Really Means to Make a Simple Product Great

The Gstaad Guy sits down with Jens Grede, co-founder and CEO of SKIMS and one of the most instinctive brand builders of his generation, to explore what it means to connect products with culture in a w...

1 Jul 1h 12min

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