Harley Finkelstein: President of Shopify – Democratising Entrepreneurship, Empowering Founders, & the Tools That Build Global Businesses
The Gstaad Guy sits down with Harley Finkelstein, President of Shopify and one of the most influential voices in modern entrepreneurship, to discuss how technology is redefining capitalism by empowering anyone, anywhere, to start and scale a business. From equipping first-time founders to run their own stores, to enabling global brands to reach millions, Harley shares how Shopify is democratising opportunity and lowering the cost of failure, making entrepreneurship more accessible than ever before.The conversation explores the ambition required to build at scale, the obsession with sharpening one’s craft, and the emotional reality of operating a business that spans borders, cultures, and time zones. Harley reflects on the future of entrepreneurship, the rise of young business builders, and why success today is no longer defined by access, but by the courage to create. An exploration of how entrepreneurship and modern commerce have become powerful engines for empowerment, creativity, and self-actualisation.Filmed at Casa Cipriani New York’s Battery Corner Suite.Chapters:(00:00) Intro ✨(02:49) What Gstaad Guy made Harley feel 🇨🇭✨(05:41) The golden age of entrepreneurship 🏆⚡(06:26) Building up Shopify 🧱🚀(13:16) Creating a business 🛠️💡(14:53) Entrepreneurship 🔥📈(17:47) Entrepreneurship in 2025 🔮🏢(19:20) Universities today 🎓❓(20:30) What is life’s work? 🧭✨(21:22) What Shopify solved ✅🧩(24:17) The story of Fashionova 👗📦(27:14) Sixteen years at Shopify ⏳🏗️(30:36) “We are spiky objects” 🧬⚡(31:10) Do you know the term Ikigai? 🎯🧘♂️(33:01) Love for storytelling 📖❤️(35:35) James Perse 👕🏛️(36:49) Side quests vs. main quests 🗺️🎯(38:15) The most successful stores on Shopify 🛒🏆(41:46) Appetite for discomfort 🌶️💪🏻(45:17) Nike 👟⚡(47:19) If you study history of commerce 📜💰(52:15) A desire to start a business ✨🚀(58:00) Intrapreneurship 🧠🏢(01:04:59) Company culture 🧬🤝🏻(01:06:30) Choosing a co-founder 🤝🏻🔑(01:07:30) À La Poubelle vs. Fantastique 🗑️✨See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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1:09:23
Jeremy Zimmer: Co-Founder & Former CEO of UTA – Building a Next-Gen Talent Powerhouse, Shaping Success, & The Nobility of Representation
The Gstaad Guy sits down with Jeremy Zimmer, co-founder and former CEO of United Talent Agency (UTA), to explore what it takes to build one of the most forward-thinking and culturally influential talent companies in the world. From discovering emerging stars to engineering opportunities across film, music, digital media, sports, and technology, Zimmer shares how diversification, strategic intuition, and innovation have shaped UTA into a modern powerhouse.The conversation delves into what it means to manufacture success alongside artists, curate teams driven by purpose, and dream in partnership with talent. Zimmer also reflects on the deep responsibility of representation, not just as a business model, but as a noble calling rooted in trust, belief, and legacy. A rare look into the mindset behind building an agency that doesn’t chase culture, but defines it.Filmed at Nobel LA’s Benedict property.Chapters:(00:00) Intro ✨(01:00) Starting UTA 🚀🏢(04:20) Building a next-gen agency ⏭️⭐️(05:02) Fear of big agencies 😨🏛️(05:38) Curating a motivated team 🔥👥(06:44) The term “talent” 🎭✨(09:50) Diversifying UTA 🌐🔄(10:50) Choosing the right path for growth 🧭📊(12:36) Pivoting to social media talent 📲🔁(18:25) Discovering talent 🔍⭐(20:59) The nobility of representing artists 👑🎨(21:40) The greatest business tool is a mirror 🪞💼(25:51) Progress breeds happiness 😊📈(27:59) Process vs. Outcome ⚙️🎯(29:52) Perfection is hard to achieve 👌🏻🧗♂️(31:28) Stepping down from CEO of UTA ⬇️👨💼(33:15) Focusing on what we need least 🧠📉(34:25) Unlocking a spiritual life 🧘🏻♀️🌱(37:34) À La Poubelle vs. Fantastique 🗑️✨See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Tinie Tempah: Artist & Entrepreneur – Faith, Creativity & The Balance Between Scarcity and Abundance
The Gstaad Guy sits down with Tinie Tempah — artist, entrepreneur, and one of the defining voices of the early 2000s music scene, to explore what it takes to pioneer success and stay ahead of the curve in an ever-evolving industry. From humble beginnings in South London’s council estates to commanding global stages, Tinie shares the mindset and discipline that carried him from mentee to mentor, artist to innovator.The conversation dives into the realities of risk, the power of reinvention, and the art of balancing creativity with entrepreneurship. Tinie reflects on his journey as a true poly-hyphenate, blending music, business, and culture, while unpacking how the early days of British grime and hip-hop shaped a generation of creators. A candid look at ambition, evolution, and the courage to keep building even when you’ve already made it.Filmed at The Berkeley, London, Knightsbridge Suite.Chapters:(00:00) Intro ✨(05:34) Modern poly-hyphenate ⚡🎭(07:37) Where it all began 🏁(10:20) “The MC guy” 🎤🔥(11:44) The birth of Tinie Tempah 🌟(14:12) Taking the leap of faith 🏃♂️✨(16:54) “Hood Economics” 🏙️📘(20:45) Launching a fashion brand 👕🚀(26:30) Challenges of a rising artist 🎶⛰️(31:27) Seeking discomfort 🧗♂️💭(33:36) Commitment to music 🎧💫(38:20) From mentee to mentor 🤝🏻🎓(42:53) Scarcity vs. Abundance in creativity 💭⚖️(50:36) Experiencing true joy 😄🌈(53:44) Nigeria breeds creativity 🇳🇬🎨(56:14) À La Poubelle vs. Fantastique 🗑️✨See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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1:02:05
Radha Arora: President of Rosewood Hotels & Resorts – Redefining Hospitality, A Sense of Place, & Loyalty In The Details
The Gstaad Guy sits down with Radha Arora, President of Rosewood Hotels & Resorts, to explore the philosophy and details that define one of the world’s most admired luxury hospitality brands. With decades of experience leading by example, Radha brings an insider’s view on how hotels can transcend function to become sanctuaries of self-actualisation and cultural expression.
The conversation unpacks the art of creating a true “sense of place,” why every detail matters, and how the “cocoon effect” transforms hospitality into an intimate, personal experience. Radha reflects on leadership, the evolution of modern luxury, and the pursuit of hospitality that is as much about inner fulfilment as it is about comfort. A rare look into the mindset of someone shaping not just hotels, but the way we experience belonging away from home.
Filmed at Nobel LA’s St. Ives property.
Chapters:
(00:00) Intro ✨
(00:40) Running a hotel 🏨
(04:23) Lead by example 🌟👣
(06:25) Rosewood 🌹🌳
(10:28) A sense of place 📍✨
(13:20) The living room of Paris 🛋️🇫🇷
(15:21) Shaping perception 👓 🎭
(21:36) Defining Luxury 💎✨
(27:20) Hiring the right team 🤝🏻👥
(31:03) Loyalty lives in the details 🔑🧵
(34:55) Dealing with guests 🙋♂️🤝🏻
(35:55) Hospitality isn’t for everyone 🚪🙂
(36:35) Absurd guest encounters 😂🍾
(46:13) Heritage vs. customer demands 🏛️⚖️
(49:23) The cocoon aspect 🪺🛌 Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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51:24
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51:24
Tom Chamberlin: Editor-in-Chief of The Rake – Wealth Whisperers, Being a Gentleman, Style Codes, & The Spirit of Savile Row
The Gstaad Guy sits down with Tom Chamberlin, Editor-in-Chief of The Rake magazine and author of Huntsman: Redefining Savile Row, to explore what it truly means to be a gentleman in today’s world. With deep roots in men’s style, tailoring, and the traditions of Savile Row, Tom brings a perspective that bridges timeless elegance with modern masculinity.
The conversation delves into the role of confidence in style, the artistry of tailoring, and how the codes of classic menswear remain relevant in shaping identity and character. Tom reflects on the evolution of masculinity, the values that define gentlemanly conduct, and why refinement goes far beyond clothing. An honest look at how style, substance, and self-assurance intertwine in the pursuit of modern elegance.
Filmed at Birley Chocolate in London.
(00:00) Intro ✨
(02:00) Land Rover Defender salute 🚙🇬🇧
(04:01) Codes of men’s style 👔📏
(06:38) Having bearing 🧍♂️🎩
(09:32) The Rake 📖👑
(13:45) Wealth whisperers 💰🤫
(16:07) Accessorising ⌚🕶️
(17:22) Values across Europe 🌍🤝🏻
(21:03) European tailoring 🪡👕
(24:45) Tom Ford 👔🕶️
(25:46) Huntsman 🧵🎯
(29:04) The core of great storytelling 📚✨
(35:49) Rethinking masculinity 🤵🤔
(37:08) The term gentleman 🎩🤝🏻
(42:36) Curiosity & escapism 🔍🌌
(48:15) American readership 🇺🇸📖
(50:18) London is changing 🇬🇧🏙️
(51:48) Elevating your style ⬆️👔
(54:10) Building your wardrobe 👕👞
(57:37) À La Poubelle vs. Fantastique 🗑️✨ Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The Gstaad Guy Podcast 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/gstaadguypodcast TikTok: https://www.tiktok.com/@gstaadguypodcast
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