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The Gstaad Guy Podcast

The Gstaad Guy Podcast

The Gstaad Guy

The Gstaad Guy Podcastย is your backstage pass to the untold stories behind excellence. Hosted by The Gstaad Guy, out of character, this guest driven, unscripted series explores the real journeys, challenges and turning points that shape those who have mastered their craft. From global tastemakers and industry leaders to creative pioneers and cultural outliers, each episode reveals what it really takes to achieve excellence. Through humour and curiosity, The Gstaad Guy peels back the layers to uncover the grit behind the glamour, offering listeners a rare glimpse into the worlds usually kept behind closed doors. Instagram: https://www.instagram.com/gstaadguypodcastย  TikTok: https://www.tiktok.com/@gstaadguypodcast

88 - Flex Founder & CEO: Zaid Rahman โ€“ Dropping Out, Token Maxing, & the Cofounder You Never Had
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  • 88 - Flex Founder & CEO: Zaid Rahman โ€“ Dropping Out, Token Maxing, & the Cofounder You Never Had

    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 fatherโ€™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 ๐ŸŽ™๏ธโœจ (03:13) Saudi, Then Dubai ๐Ÿ—๏ธ๐ŸŒ (04:15) No Lamborghinis, No Butlers ๐Ÿš—๐Ÿ˜ (06:06) First Business At Thirteen ๐Ÿ’ป๐Ÿš€ (06:54) Perspective Is The Greatest Luxury ๐Ÿ”ญ๐Ÿ’Ž (07:22) Flex Fuels Ambition ๐Ÿงพ๐Ÿ”ฅ (10:47) Paid To Drop Out ๐ŸŽ“๐Ÿ’ฐ (13:15) Fifty Of Three Hundred ๐Ÿ“Š๐Ÿ† (17:00) Zero Days Of College ๐Ÿซ๐Ÿ˜ (17:55) Chaotic In The Nicest Way ๐ŸŒ€โค๏ธ (20:41) Chewing Glass ๐ŸชŸ๐Ÿ’ช (21:23) Why Finance Sucks ๐Ÿ’ธโŒ (23:10) Wait Until You See Construction ๐Ÿงฑ๐Ÿ˜ฎ (27:03) Sixty Days Of Float ๐Ÿ’ณโณ (30:07) Hiding The Complexity ๐Ÿ“ฑโœจ (32:29) What AI Native Means ๐Ÿค–๐Ÿ’ก (34:01) Beacon, Your Financial Wrapped ๐Ÿ“ˆโœจ (38:32) The Best Thing Was Anthropic ๐Ÿš€๐Ÿค– (40:03) What An Agent Actually Is ๐Ÿ—บ๏ธ๐Ÿค– (43:19) White Collar Goes First ๐Ÿ’ผโšก (45:06) Token Maxing โšก๐Ÿ”ฅ (46:53) The Two Hundred Thousand Dollar Weekend ๐Ÿ’ฅ๐Ÿ’ฐ (48:29) Charging For The Highway ๐Ÿ›ฃ๏ธ๐Ÿ’ฐ (54:47) Where AI Is Heading ๐Ÿ”ฎ๐ŸŒ (59:22) Generalists Win Now ๐Ÿง ๐Ÿ† (1:01:39) Flex Elite ๐Ÿ’ โœจ (1:04:07) Acquiring Selfbook ๐Ÿจ๐Ÿ’ผ (1:05:42) The Most Confusing Age ๐Ÿงญ๐Ÿ’ญ (1:07:49) ร€ La Poubelle vs. Fantastique ๐Ÿ—‘๏ธโœจ (1:11:26) Ask Me In Five Years โณ๐Ÿ”ฎ Learn more about your ad choices. Visit megaphone.fm/adchoices

    Wed, 28 Oct 2026
  • 87 - Expedia Group CEO: Ariane Gorin โ€“ Ambition, Manifesting, & Taking the Job Nobody Wanted

    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 startupโ€™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 ๐ŸŽ™๏ธโœจ (02:34) Thirteen Years To CEO ๐Ÿชœ๐Ÿ† (03:33) A Household Name Of Household Names ๐Ÿท๏ธโœจ (05:19) The Brands Under The Group ๐Ÿงณ๐ŸŒ (07:11) A Berkeley Girl, Not A Hippie ๐ŸŽ“๐Ÿ˜ (08:29) Twelve Months Became Thirteen Years โœˆ๏ธโณ (08:52) Eight AM In Paris, Empty Office ๐Ÿฅ๐Ÿ›๏ธ (10:37) They Didnโ€™t Fit Me In A Box ๐Ÿ‡ซ๐Ÿ‡ท๐Ÿ’ก (12:05) Immigrant Of Love ๐Ÿ’˜๐ŸŒ (12:48) A Bird Without Wings ๐Ÿ•Š๏ธ๐Ÿ’ญ (13:23) Too Ambitious To Hire ๐Ÿ’ผ๐Ÿ”ฅ (15:11) On Manifesting ๐Ÿ”ฎโœจ (17:53) She Wants Your Job ๐Ÿข๐Ÿ˜ (21:49) Fourteen Days Versus Twenty Eight ๐Ÿ–๏ธโš–๏ธ (23:06) Euro Curious Americans ๐Ÿ‡ช๐Ÿ‡บ๐Ÿ‡บ๐Ÿ‡ธ (25:44) Families, Pets And Travel ๐Ÿ“ธโค๏ธ (26:34) How Expedia Started ๐Ÿš€๐Ÿ’ก (29:44) Holding Company To Platform ๐Ÿ”—๐Ÿ“ˆ (31:57) What Partners Actually Get ๐Ÿค๐Ÿ’Ž (34:35) Expand The Pie ๐Ÿฅงโœจ (35:57) The AI Question ๐Ÿค–๐Ÿ’ก (38:34) The NASA Janitor ๐ŸŒ™๐Ÿงน (40:54) Nobody Else Wanted That Job ๐Ÿ“ˆ๐Ÿ’ช (42:22) Killing The Bureaucracy ๐Ÿงนโšก (44:06) Why He Left Apple โœจ๐ŸŽ (47:19) ร€ La Poubelle vs. Fantastique ๐Ÿ—‘๏ธโœจ Learn more about your ad choices. Visit megaphone.fm/adchoices

    Sun, 25 Oct 2026
  • 86 - Visual Artist Working Across Painting, Drawing & Sculpture: Devon DeJardin โ€“ Guardians, Abundance, & Privacy as the Last Luxury

    The Gstaad Guy sits down with Devon DeJardin, the visual artist working across painting, drawing and sculpture, whose Guardian figures have travelled from a friendโ€™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 ๐ŸŽ™๏ธโœจ (00:48) A Brand With His Brother ๐Ÿ‘•๐Ÿค (02:12) Painted Jackets And Bad Interviews ๐Ÿงฅ๐Ÿ˜… (06:18) God Told Me To Tell You To Paint ๐Ÿ™๐ŸŽจ (07:43) First Canvas From Michaelโ€™s ๐ŸŽจโœจ (09:05) The Guardianโ€™s Face ๐Ÿ‘ค๐Ÿ” (10:16) A Cheque For Sixteen Grand ๐Ÿ’ฐโœ๏ธ (12:50) A Lie About Paris โœˆ๏ธ๐Ÿ˜ (15:19) Donโ€™t Wait For The Call โญ๐Ÿš€ (17:30) Inside The Art Factory ๐Ÿญ๐ŸŽจ (20:53) Kanye, Condo And Hypebeasts ๐ŸŽง๐Ÿ‘Ÿ (22:15) The Gunna Album Cover ๐Ÿ’Ž๐Ÿ–ผ๏ธ (23:44) Midnight Dinner In Dubai ๐ŸŒ™๐Ÿฝ๏ธ (25:12) Calling The Hit ๐Ÿ”ฅ๐ŸŽต (27:37) Gunna As His Own Guardian ๐Ÿ›ก๏ธโœจ (29:41) The Driver Who Had No Idea ๐Ÿš—๐Ÿ˜ฎ (32:50) Privacy Is The Last Luxury ๐Ÿ”’๐Ÿ’Ž (36:32) The Absurdity Of The Rooms ๐Ÿ˜‚๐Ÿ›๏ธ (39:41) The Dream He Had ๐Ÿ’ญโœจ (42:35) The Sound Of Grinding โš™๏ธ๐Ÿ”ฅ (47:12) Abundance And Gatekeepers ๐Ÿšช๐ŸŒฟ (50:08) Currency Is A Current ๐ŸŒŠ๐Ÿ’ฐ (51:46) Ten Years Of LA ๐ŸŒดโณ (54:25) Forgiveness At A Distance ๐Ÿ•Š๏ธโค๏ธ (56:28) The Studio As A Day Job โฐ๐ŸŽจ (58:09) Prepare For The Best โœจ๐Ÿ’ก (59:19) ร€ La Poubelle vs. Fantastique ๐Ÿ—‘๏ธโœจ (1:06:30) It Makes Sense Looking Back ๐Ÿ”ญ๐Ÿ’ก Learn more about your ad choices. Visit megaphone.fm/adchoices

    Wed, 21 Oct 2026
  • 85 - Sporty & Rich Founder & CEO: Emily Oberg โ€“ Originality, Nostalgia, & the Real Dream

    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, Hรดtel 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 ๐ŸŽ™๏ธโœจ (01:42) The Supreme Line Videos That Started It ๐Ÿงข๐Ÿ“ฑ (03:05) Leaving Kith And Betting On LA ๐ŸŒด๐ŸŽฒ (04:07) The Idea Was Just A Mood Board ๐Ÿ“Œ๐Ÿ’ก (07:04) A Boutique On Place Des Lices ๐Ÿ‡ซ๐Ÿ‡ท๐Ÿ›๏ธ (07:42) Ten Years, And The Brands That Called ๐Ÿคโณ (09:30) Why The Word Rich Makes People Flinch ๐Ÿ’ฌ๐Ÿ’ฐ (10:28) Paris, Then Back To LA โœˆ๏ธ๐ŸŒด (11:42) Going Digital First, And Why Sheโ€™d Say Donโ€™t ๐Ÿ’ปโš ๏ธ (13:14) When Discovery Became Pay To Play ๐Ÿ“‰๐Ÿ’ธ (14:33) The First Touch Of A Product ๐Ÿ›๏ธโœจ (15:51) The Lockdown Day That Changed Everything ๐Ÿ“ฆ๐Ÿ”„ (17:49) Selfridges, And Why It Still Counts ๐Ÿฌโœจ (20:08) Who Sporty & Rich Is Actually For ๐Ÿ‘ฅ๐ŸŽฏ (23:41) What Being A CEO Actually Involves ๐Ÿ—‚๏ธ๐Ÿ’ผ (27:41) The Least Glamorous Job There Is ๐Ÿงน๐Ÿ˜ (29:33) There Is No Right Decision ๐ŸŽฒโš–๏ธ (31:30) Dating When The Business Comes First ๐Ÿ’๐Ÿ’ผ (32:48) The King Or The Prince? ๐Ÿ‘‘๐Ÿค” (35:41) Observer, Storyteller, Builder ๐Ÿ”ญ๐Ÿ“– (38:31) Why She Hates The Word Creative ๐ŸŽฌโŒ (40:10) The World She Wanted To Live In ๐Ÿš™๐ŸŒ (41:25) What People Are Really Chasing ๐Ÿ’ฐ๐Ÿ” (43:11) The Rhetoric That Follows Successful Women ๐Ÿ—ฃ๏ธโšก (45:25) The Biological Clock And The Company โฑ๏ธ๐Ÿ’ผ (46:58) Setting Boundaries Early ๐Ÿงฑ๐Ÿ’ช (51:39) And Then What? ๐Ÿงญ๐Ÿ’ญ (54:57) Choosing To Be The Brand ๐Ÿ“ธโœจ (56:34) Ralph Lauren And The Real Dream ๐ŸŒ…๐Ÿ‘” (60:30) ร€ La Poubelle vs. Fantastique ๐Ÿ—‘๏ธโœจ Try Granola for free at: https://www.granola.ai/GSTAADGUY Learn more about your ad choices. Visit megaphone.fm/adchoices

    Sun, 18 Oct 2026
  • 84 - Sothebyโ€™s Chairman, Europe & Principal Auctioneer: Oliver Barker โ€“ Collecting, Taste, & the Magic of the Saleroom

    The Gstaad Guy sits down with Oliver Barker, chairman of Sothebyโ€™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 Christieโ€™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 expertโ€™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 ๐ŸŽ™๏ธโœจ (01:36) A Golden Era For Auctions โœจ๐Ÿ”จ (02:26) Older Than America ๐Ÿ›๏ธโณ (05:06) The Best Free Museum In Mayfair ๐Ÿ–ผ๏ธ๐Ÿ‡ฌ๐Ÿ‡ง (06:21) A Hundred Thousand People For Freddie ๐Ÿ‘‘๐ŸŽค (07:36) Thirty Two Years, Starting As An Intern ๐ŸŽ“โณ (08:17) The Long Corridor Problem ๐Ÿšช๐Ÿ’ญ (09:14) Due Diligence Before You Bid ๐Ÿ”๐Ÿ”จ (10:25) Authenticating What No Book Records ๐Ÿ“œ๐Ÿ” (11:43) What Makes An Expert ๐Ÿง ๐Ÿ† (14:57) Sothebyโ€™s Said No To My Dad ๐ŸŽจ๐Ÿ˜ฎ (15:22) The Picasso Sale That Hooked Him ๐Ÿบโค๏ธ (16:54) Cรฉzannes From Snappy Snaps ๐Ÿ“ธ๐Ÿ˜ (18:59) Knowing The Room As An Auctioneer ๐Ÿ”จ๐Ÿ‘๏ธ (19:39) Collections Fifty Years In The Making ๐Ÿคโณ (24:02) Collecting On A Salary ๐Ÿ’ท๐Ÿ–ผ๏ธ (25:23) Lockdown And The Livestream Auction ๐Ÿ’ป๐Ÿ”จ (29:16) David Bowie The Collector ๐ŸŽธ๐Ÿ–ผ๏ธ (31:38) Grading The Birkin ๐Ÿ‘œ๐Ÿ” (33:04) Restitution And Authenticity โš–๏ธ๐Ÿ›๏ธ (37:19) From The Medicis To The Upper East Side ๐Ÿ›๏ธ๐Ÿ—ฝ (43:41) A Collectorโ€™s Year ๐Ÿ“…๐Ÿ–ผ๏ธ (48:05) Specialists, Generalists And Sue Tilley ๐ŸŽจ๐Ÿ” (52:35) ร€ La Poubelle vs. Fantastique ๐Ÿ—‘๏ธโœจ (54:43) Advice For The Art Curious ๐Ÿงญ๐ŸŽจ Learn more about your ad choices. Visit megaphone.fm/adchoices

    Wed, 14 Oct 2026
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