The Gstaad Guy Podcast

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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The Gstaad Guy sits down with Gary Vaynerchuk, chairman of VaynerX and founder and CEO of VeeFriends, to explore what two decades of watching attention move has taught him about people. Gary built a career on seeing platforms before anyone else took them seriously, and reflects on a trajectory defined by conviction, self awareness, and a willingness to say the thing nobody in the room wants to hear, including about himself.

The conversation gets into what he actually feels in rooms full of the one percent, why the loudest critics in someone’s life rarely deserve the authority they are given, and how he tells the difference between encouraging someone and enabling them. Gary is candid about the years he spent holding his own personality back in public and about where he disagrees with almost everyone on what AI will do to work. He argues we have become brilliant at pointing fingers and atrocious at pointing thumbs, and that the only honest place to start is with yourself. Blunt, unusually generous, and completely unbothered by how any of it sounds, it is a conversation about attention, accountability, and the insecurity underneath most of what people chase.

Filmed at Casa Cipriani New York's Premier River View Suite.

(00:00) Intro ✨🎙️

(01:19) Seeing Things Before The Trend 👁️📈

(04:20) One Day I Won’t Be The Kid 👶⏳

(08:28) Judge The Judger 👀⚖️

(12:25) Confirmation Is Not Advice 🗣️❌

(13:18) Hoping To Say I Don’t Know 🤔💡

(15:30) Betting On People 🎲❤️

(17:32) Why He’s Not Scared Of Being Let Down 💪🛡️

(19:47) Confidence, Insecurity And The Same Pillow 😴⚖️

(23:13) Curiosity, Optimism, Delusion 🔍☀️💭

(24:27) Romanticising Yesterday 📷🌅

(27:15) Compassion For The One Percent Cool ❤️😎

(29:46) Humour As The Way In 😂🚪

(30:51) Building The Marketing Death Star 🌑📢

(34:36) Why He Never Saw Luxury On His Feed 📱💎

(39:21) The First Eighty Episodes Were Subdued 🎙️📉

(40:26) Authenticity, Kindness And The Walk Away Test 🚶❤️

(43:21) Twenty Fifty And Nineteen Fifty At Once ⏳🔄

(48:17) Have You Ever Heard Of America 🇺🇸😏

(52:00) The Temptation Problem 😈⚖️

(54:50) Be A Parent, Then 👨‍👧💡

(1:00:33) Looking For COPs 🔍🤝

(1:04:34) À La Poubelle vs. Fantastique 🗑️✨

(1:11:19) A Closing Note 💌🌟
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The Gstaad Guy sits down with Harry Stebbings, founder of 20VC and one of the most prolific investors and podcasters in Europe, to explore what separates the people who say they want it from the people who genuinely cannot do anything else. Harry started a podcast from his bedroom at seventeen with no university and no network, built it into an audience of millions and a fund with around a billion dollars under management, and reflects on a career defined by seeing early that media would become venture capital's real differentiator.

The conversation gets into the specific signals he looks for in founders and why the usual answers about resilience and discipline tell you nothing. Harry is candid about the costs that come with real commitment, from the friends and birthdays missed to the dissatisfaction he thinks founders have to make peace with, and he is clear about where he draws his own line. He makes the case for Europe over the US, explains why he would rather be relevant than rich, and lays out what he believes is coming next with AI. Fast, unguarded, and willing to be challenged on every point, it is a conversation about ambition, honesty, and what you are actually prepared to pay.

Filmed at The Peninsula London.

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(00:00) Intro 🎙️✨

(01:44) Weakness Leaving Your Body 💪🔥

(03:15) If I Were You, I'd Do This 👆💡

(04:21) Insight Developments 🔍📈

(05:10) The Scene In The Social Network 🎬💻

(06:36) Three Ways We Make Money 💰🔑

(09:11) The Signals I Look For 👁️🎯

(10:44) Nobody Great Comes Out Of McKinsey 🏢😏

(12:25) Teach Your Children To Tell Stories 👶📖

(15:08) Fifty Thousand DMs At Two In The Morning 📱😮

(16:22) At Peace With Dissatisfaction 🧘⚖️

(18:33) Found On The Kitchen Floor 🍳😔

(21:20) There Is No Cheat Code 🎮💡

(23:23) The Coffee Bar In Milan ☕🇮🇹

(25:52) Betting A Career On Europe 🇪🇺🎲

(28:41) Why Founders Now Want To Build Here 🏗️🌍

(31:47) A Unicorn Isn't Enough Any More 🦄📈

(32:54) A Hundred Million Beats A Billion 💰⚖️

(35:09) Fame Is The Watch ⌚👀

(36:57) Founder Porn 💻🔥

(40:04) The Parent Problem 👨‍👩‍👧💭

(41:26) Four Hobs, Two Burners 🔥⚖️

(43:06) Where AI Actually Is 🤖🔍

(49:55) Build An AI School 🤖🏫

(51:50) Education, Romance, Housing 📚❤️

(55:32) The Friend Zone Is A Lie 💭❌

(58:50) Keep The Main Thing The Main Thing 🎯💡

(1:00:51) À La Poubelle vs. Fantastique 🗑️✨

(1:07:41) A Message For The Twenty Somethings 💌🌟
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The Gstaad Guy sits down with Éric Martel, CEO of Bombardier, at the company's completion centre in Montreal with the Global 8000 behind them, to explore how a snowmobile inventor from a small Quebec town became the foundation of one of the world's great aerospace companies. Éric reflects on a career that began on the factory floor and a company whose defining trait is a willingness to take on things it has never done before, from building metro cars without ever having built a train to inventing the regional jet.

The conversation gets into what actually separates one aircraft from another once you are past the specification sheet, and why the company still gathers the people who built each plane to meet the family taking it home. Éric is candid about the supply constraints no amount of demand can solve, the buyers now arriving in their twenties and skipping straight to the flagship, and what he looks for in the people he hires across engineering, design and everything in between. Warm, precise, and unmistakably proud of where it is all made, it is a conversation about craftsmanship, national identity, and the pursuit of perfection at scale.

Filmed at the Bombardier Completion Centre in Montreal.

(00:00) Intro ✨🎙️

(03:41) It Started With A Snowmobile 🏔️🛷

(05:46) He'd Never Built A Train 🚂😮

(07:28) Canadair, Learjet And The Regional Jet ✈️🇨🇦

(12:01) A Family Business At Twenty Thousand People 👨‍👩‍👧‍👦🏭

(14:27) The Ceremony Room 🏛️✨

(16:50) Ten Days To Become An 8000 🏔️💪

(17:59) Why You Land Rested 😴✈️

(19:24) Four Countries, Four Days 🌍⚡

(20:32) The Wing Is The Secret Weapon 🛩️🔑

(22:47) Thirty Minutes Or Two Days ⏱️🗺️

(24:07) What Bombardier Means To Canada 🇨🇦🏆

(29:22) Hydropower And Perfect Stitching 💧🧵

(30:41) The Craft You Can Touch 🤲✨

(32:51) We Invented The Winglet ✈️💡

(34:15) Inside The US Market 🇺🇸📈

(36:13) They're Knocking At Twenty Seven 🚪⏳

(38:11) How To Be A Good Guest On Board 😊✈️

(40:06) The Pen That Popped 🖊️✨

(42:46) From The Factory Floor To CEO 🏭👔

(47:17) The Plane That Calls Ahead ✈️📞

(51:04) Everyone Wants Theirs First 🏆⚡

(53:10) À La Poubelle vs. Fantastique 🗑️✨

(53:52) Luxury That Actually Works 💎✅
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