Quitting My 6-Figure Career with Only 20% Income Replaced: Gil Chan’s Story

"I knew that if I didn't take this chance, I would be kicking myself for the rest of my life."In this episode of the Grow STR Podcast, Donnie Dimes and Sam Mistretta sit down with Gil Chan, the founder and CEO of CraftedStays. Gil is a veteran of six Silicon Valley startups (including one bought by Samsung), but he risked it all to solve one of the biggest problems in the short-term rental industry: the over-reliance on Airbnb.Gil shares the radical story of leaving a healthy six-figure tech salary when his STR business had only replaced 20% of his income. He breaks down the "perfect storm" that led to the creation of the "Shopify for Short-Term Rentals" and how he used e-commerce principles to 4x his company’s revenue in just one year.In this episode, we cover:The "Kick Myself" Test: How to know when it is finally time to leave your W2.The PowerPoint Strategy: How Gil treated his marriage like a board meeting to build trust and get his wife on board with remote investing.The Shopify Moment: Why property managers need a high-converting direct booking site that works as well as an e-commerce store.Bootstrapping vs. VC: Why Gil turned down outside funding to keep his customers at the forefront of his product design.The Future of Search (AEO): How LLMs like ChatGPT and Perplexity are changing how guests find your properties in 2026.The Best Growth Move: Why Gil still onboards every single customer personally.Action Item: Stop being a "viral influencer" and start being an expert. Use AI to learn what you don't know, but keep your authenticity in what you do.Connect with Gil Chan:Gil Chan is the founder and CEO of CraftedStays, a direct booking website platform for short-term rental operators, recently named Website Builder of the Year by Travel and Hospitality Tech Outlook.He has spent 15 years in tech and worked at six startups across eCommerce, IoT, and logistics, including leading API integrations with Shopify, Wix, and Squarespace at Shippo.After becoming a short-term rental host in the Great Smoky Mountains and Branson, he experienced the limits of outdated PMS websites and high-cost agency builds, which led him to create a scalable alternative.CraftedStays launched in January 2024 as a mobile-first platform that integrates with systems such as Guesty, Hostaway, Hostfully, Hospitable, and OwnerRez, enabling operators to launch SEO-ready sites in minutes.Gil also hosts the Booked Solid Show podcast, speaks at industry events, and focuses on helping operators gain more control over their direct bookings.Website: https://craftedstays.coInstagram: https://www.instagram.com/craftedstaysFacebook: https://www.facebook.com/gilbertchanLinkedIn: https://www.linkedin.com/in/thegilbertchan/Connect with Grow STR:If Gil’s risk-taking spirit inspired you today, please follow the show and leave us a 5-star review!