The Gstaad Guy Podcast

The Gstaad Guy sits down with Zaid Rahman, founder and CEO of Flex, who has never held a normal job, never spent a day at university, and now runs the financial platform behind some of the fastest growing companies in the world, to explore what building actually costs and why the people who look like they have already made it are so often the ones getting the least help. With a childhood spent watching his father’s construction business rise and fall in Dubai, Zaid reflects on where ambition is inherited from, why finance is the part of running a company nobody wants to touch, and what it means to hand someone the cofounder he never had.

The conversation dives into what an agent actually is once you strip the terminology away, the strange economics of token maxing, and where the value in AI will settle once the noise clears. Zaid shares what it looks like inside a company where forty five engineers ship twenty four products, where an intern can spend two hundred thousand dollars over a weekend, and where the most expensive department is now legal. A candid look at money, machines, and the unglamorous work behind every business that looks effortless from the outside.

Filmed at The Peninsula in London.

(00:00) Intro 🎙️✨

(03:13) Saudi, Then Dubai 🏗️🌍

(04:15) No Lamborghinis, No Butlers 🚗😏

(06:06) First Business At Thirteen 💻🚀

(06:54) Perspective Is The Greatest Luxury 🔭💎

(07:22) Flex Fuels Ambition 🧾🔥

(10:47) Paid To Drop Out 🎓💰

(13:15) Fifty Of Three Hundred 📊🏆

(17:00) Zero Days Of College 🏫😏

(17:55) Chaotic In The Nicest Way 🌀❤️

(20:41) Chewing Glass 🪟💪

(21:23) Why Finance Sucks 💸❌

(23:10) Wait Until You See Construction 🧱😮

(27:03) Sixty Days Of Float 💳⏳

(30:07) Hiding The Complexity 📱✨

(32:29) What AI Native Means 🤖💡

(34:01) Beacon, Your Financial Wrapped 📈✨

(38:32) The Best Thing Was Anthropic 🚀🤖

(40:03) What An Agent Actually Is 🗺️🤖

(43:19) White Collar Goes First 💼⚡

(45:06) Token Maxing ⚡🔥

(46:53) The Two Hundred Thousand Dollar Weekend 💥💰

(48:29) Charging For The Highway 🛣️💰

(54:47) Where AI Is Heading 🔮🌍

(59:22) Generalists Win Now 🧠🏆

(1:01:39) Flex Elite 💠✨

(1:04:07) Acquiring Selfbook 🏨💼

(1:05:42) The Most Confusing Age 🧭💭

(1:07:49) À La Poubelle vs. Fantastique 🗑️✨

(1:11:26) Ask Me In Five Years ⏳🔮
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The Gstaad Guy sits down with Ariane Gorin, CEO of Expedia Group, and one of the few people running a company of that scale who was once told plainly that her ambition would make her unhireable, to explore what it takes to hold your nerve when the quality that makes you good is read as a threat. With a career built across Berkeley, Paris, London and Seattle, Ariane reflects on adapting to a culture that will not adapt to you, betting on yourself when a room has already decided what you are, and the quieter work of knowing what you want before you ever say it out loud.

The conversation dives into manifesting as a practice rather than a slogan, why the roles nobody else wants are so often the ones worth taking, and how you hold a startup’s speed inside a company of fifteen thousand people. Ariane makes the case for expanding the pie rather than dividing it, for building a business that creates value on both sides of a marketplace instead of sitting in the middle of it, and for a purpose simple enough that everyone from the engineer to the lawyer can see their part in it. A grounded look at ambition, leadership, and an industry that exists because of what people choose to remember.

Filmed at The Londoner in London.

(00:00) Intro 🎙️✨

(02:34) Thirteen Years To CEO 🪜🏆

(03:33) A Household Name Of Household Names 🏷️✨

(05:19) The Brands Under The Group 🧳🌍

(07:11) A Berkeley Girl, Not A Hippie 🎓😏

(08:29) Twelve Months Became Thirteen Years ✈️⏳

(08:52) Eight AM In Paris, Empty Office 🥐🏛️

(10:37) They Didn’t Fit Me In A Box 🇫🇷💡

(12:05) Immigrant Of Love 💘🌍

(12:48) A Bird Without Wings 🕊️💭

(13:23) Too Ambitious To Hire 💼🔥

(15:11) On Manifesting 🔮✨

(17:53) She Wants Your Job 🏢😏

(21:49) Fourteen Days Versus Twenty Eight 🏖️⚖️

(23:06) Euro Curious Americans 🇪🇺🇺🇸

(25:44) Families, Pets And Travel 📸❤️

(26:34) How Expedia Started 🚀💡

(29:44) Holding Company To Platform 🔗📈

(31:57) What Partners Actually Get 🤝💎

(34:35) Expand The Pie 🥧✨

(35:57) The AI Question 🤖💡

(38:34) The NASA Janitor 🌙🧹

(40:54) Nobody Else Wanted That Job 📈💪

(42:22) Killing The Bureaucracy 🧹⚡

(44:06) Why He Left Apple ✨🍎

(47:19) À La Poubelle vs. Fantastique 🗑️✨
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The Gstaad Guy sits down with Devon DeJardin, the visual artist working across painting, drawing and sculpture, whose Guardian figures have travelled from a friend’s apartment floor in North Hollywood to private collections and the cover of a number one album. Devon had never picked up a brush. He had a world religion degree, five hundred dollars to his name, a mattress he folded into a laundry closet each morning and a stack of unsold jackets when a stranger in Indiana paid him a hundred dollars for a ten minute phone call to tell him he was meant to paint. Six months later some of the most prominent collectors in Los Angeles were emailing his studio.

The conversation is about what he has built on top of that. Devon makes the case for abundance over gatekeeping, for giving without expectation, and for treating money the way you would treat a current, as something that only works while it is moving. He is sceptical of grinding and precise about why, he keeps studio hours like a day job because discipline is what leaves you ready, and he argues that in a world of total access the doors you choose to keep shut are the last real luxury. Running underneath all of it is the posture he brings to every room he is invited into, which is to assume he is the least knowledgeable person in it and to ask accordingly.

Filmed at The Maybourne Beverly Hills Garden Suite.

(00:00) Intro 🎙️✨

(00:48) A Brand With His Brother 👕🤝

(02:12) Painted Jackets And Bad Interviews 🧥😅

(06:18) God Told Me To Tell You To Paint 🙏🎨

(07:43) First Canvas From Michael’s 🎨✨

(09:05) The Guardian’s Face 👤🔍

(10:16) A Cheque For Sixteen Grand 💰✍️

(12:50) A Lie About Paris ✈️😏

(15:19) Don’t Wait For The Call ⭐🚀

(17:30) Inside The Art Factory 🏭🎨

(20:53) Kanye, Condo And Hypebeasts 🎧👟

(22:15) The Gunna Album Cover 💎🖼️

(23:44) Midnight Dinner In Dubai 🌙🍽️

(25:12) Calling The Hit 🔥🎵

(27:37) Gunna As His Own Guardian 🛡️✨

(29:41) The Driver Who Had No Idea 🚗😮

(32:50) Privacy Is The Last Luxury 🔒💎

(36:32) The Absurdity Of The Rooms 😂🏛️

(39:41) The Dream He Had 💭✨

(42:35) The Sound Of Grinding ⚙️🔥

(47:12) Abundance And Gatekeepers 🚪🌿

(50:08) Currency Is A Current 🌊💰

(51:46) Ten Years Of LA 🌴⏳

(54:25) Forgiveness At A Distance 🕊️❤️

(56:28) The Studio As A Day Job ⏰🎨

(58:09) Prepare For The Best ✨💡

(59:19) À La Poubelle vs. Fantastique 🗑️✨

(1:06:30) It Makes Sense Looking Back 🔭💡
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The Gstaad Guy sits down with Emily Oberg, founder and CEO of Sporty & Rich, who turned a Tumblr mood board into one of the most imitated brands in fashion. Before the store on Place des Lices in Saint Tropez, before Selfridges, Lacoste, Hôtel du Cap and Le Bristol, there were twenty sweatshirts she packed and posted herself. Ten years on, she is clear that the stretch in between is the part nobody films, and that the day during lockdown when a single drop did fifteen times its usual figure only reads as a beginning because the decade in front of it is invisible.

What follows is an unusually plain account of what the work asks of her. She creates selfishly, on the conviction that you have to know what people will like before they know it themselves, and she romanticises the past without apology, from the O.C. campaign to the Carolyn Bessette shoot in Tribeca four years before anyone else arrived there. She is candid about the rest, that running the company is the least glamorous job inside it, that there is no right decision and only decisions and consequences, and that ninety five percent of this is the work while the outcome lasts a day. What she keeps returning to is originality, having an opinion of your own in a culture built on copying, and protecting the reason you started. She still makes everything for her fifteen year old self, and she still believes the Ralph Lauren line that you have to accomplish your dream before you find out what the real one is.

Filmed at The Maybourne Beverly Hills Garden Suite.

Chapters:

(00:00) Intro 🎙️✨

(01:42) The Supreme Line Videos That Started It 🧢📱

(03:05) Leaving Kith And Betting On LA 🌴🎲

(04:07) The Idea Was Just A Mood Board 📌💡

(07:04) A Boutique On Place Des Lices 🇫🇷🛍️

(07:42) Ten Years, And The Brands That Called 🤝⏳

(09:30) Why The Word Rich Makes People Flinch 💬💰

(10:28) Paris, Then Back To LA ✈️🌴

(11:42) Going Digital First, And Why She’d Say Don’t 💻⚠️

(13:14) When Discovery Became Pay To Play 📉💸

(14:33) The First Touch Of A Product 🛍️✨

(15:51) The Lockdown Day That Changed Everything 📦🔄

(17:49) Selfridges, And Why It Still Counts 🏬✨

(20:08) Who Sporty & Rich Is Actually For 👥🎯

(23:41) What Being A CEO Actually Involves 🗂️💼

(27:41) The Least Glamorous Job There Is 🧹😏

(29:33) There Is No Right Decision 🎲⚖️

(31:30) Dating When The Business Comes First 💍💼

(32:48) The King Or The Prince? 👑🤔

(35:41) Observer, Storyteller, Builder 🔭📖

(38:31) Why She Hates The Word Creative 🎬❌

(40:10) The World She Wanted To Live In 🚙🌍

(41:25) What People Are Really Chasing 💰🔍

(43:11) The Rhetoric That Follows Successful Women 🗣️⚡

(45:25) The Biological Clock And The Company ⏱️💼

(46:58) Setting Boundaries Early 🧱💪

(51:39) And Then What? 🧭💭

(54:57) Choosing To Be The Brand 📸✨

(56:34) Ralph Lauren And The Real Dream 🌅👔

(60:30) À La Poubelle vs. Fantastique 🗑️✨

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The Gstaad Guy sits down with Oliver Barker, chairman of Sotheby’s Europe and the man on the rostrum for many of the largest sales in the world, to explore what thirty two years at the same house teaches you about objects and the people who love them. Oliver joined as an unpaid intern in 1993 after Christie’s turned him down, and reflects on a career built on one unplanned afternoon, an eye trained by looking rather than reading, and the conviction that the greatest auctions are celebrations of culture rather than transactions.

The conversation gets into how an expert’s eye is actually formed, what it takes to authenticate a work that appears in no book, and why he thinks the auction world has been guilty of elitism when its doors are open to anyone. Oliver is candid about collecting on a salary, and about the trust required when someone hands over a collection fifty years in the making. He explains why lockdown changed the saleroom permanently, what the next decade demands on authenticity, and why he keeps coming back to a line from Damien Hirst about pockets and shrouds. Warm, erudite, and genuinely delighted by the objects he handles, it is a conversation about expertise, taste, and the pleasure of looking properly.

Filmed at AP House London.

(00:00) Intro 🎙️✨

(01:36) A Golden Era For Auctions ✨🔨

(02:26) Older Than America 🏛️⏳

(05:06) The Best Free Museum In Mayfair 🖼️🇬🇧

(06:21) A Hundred Thousand People For Freddie 👑🎤

(07:36) Thirty Two Years, Starting As An Intern 🎓⏳

(08:17) The Long Corridor Problem 🚪💭

(09:14) Due Diligence Before You Bid 🔍🔨

(10:25) Authenticating What No Book Records 📜🔍

(11:43) What Makes An Expert 🧠🏆

(14:57) Sotheby’s Said No To My Dad 🎨😮

(15:22) The Picasso Sale That Hooked Him 🏺❤️

(16:54) Cézannes From Snappy Snaps 📸😏

(18:59) Knowing The Room As An Auctioneer 🔨👁️

(19:39) Collections Fifty Years In The Making 🤝⏳

(24:02) Collecting On A Salary 💷🖼️

(25:23) Lockdown And The Livestream Auction 💻🔨

(29:16) David Bowie The Collector 🎸🖼️

(31:38) Grading The Birkin 👜🔍

(33:04) Restitution And Authenticity ⚖️🏛️

(37:19) From The Medicis To The Upper East Side 🏛️🗽

(43:41) A Collector’s Year 📅🖼️

(48:05) Specialists, Generalists And Sue Tilley 🎨🔍

(52:35) À La Poubelle vs. Fantastique 🗑️✨

(54:43) Advice For The Art Curious 🧭🎨
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