How He Built the Bloomberg of Travel: The Story of Skift with Rafat Ali

What if the future of storytelling isn't about bigger platforms — but sharper taste? What if the real shift happening in media isn't just economic... but moral? Today, you’re about to meet Rafat Ali — founder and CEO of Skift, one of the most respected travel media brands in the world. But his story didn’t start there. Rafat grew up in India, a shy kid who stuttered — and somehow rewrote his future with nothing but words and a relentless eye for what others missed. He went from studying engineering to working for tech media icon Jason Calacanis during the first dot-com boom...to later building Skift into a brand so trusted that today, CEOs and world leaders cross conference halls just to get a bro hug from him. In this conversation, Rafat shares why legacy media is collapsing, what too many creators get wrong about influence, and how AI and independent media are re-drawing the map faster than most realize. We talk about why design — not data — will be the real differentiator in the next chapter of content. We dive into the hidden risks of "audience capture" — and why building something truly enduring requires the courage to be misunderstood for a while. And we explore why Rafat believes the next great media empires won't be built by corporations — but by people, building with instinct, action, and radical authenticity. If you care about the future of media, if you're trying to build anything magnetic, or if you just want a rare look inside the mind of one of the industry's true visionaries...you're in the right place. Behind the Stays is brought to you by Journey — a first-of-its-kind loyalty program that brings together an alliance of the world’s top independently owned and operated stays and allows travelers to earn points and perks on boutique hotels, vacation rentals, treehouses, ski chalets, glamping experiences and so much more. Your host is Zach Busekrus, Head of the Journey Alliance. If you are a hospitality entrepreneur who has a stay, or a collection of stays with soul, we’d love for you to apply to join our Alliance at journey.com/alliance.