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David Gardner, co-founder of The Motley Fool, is among the most respected and trusted sources on investing. As a best-selling author, hugely successful stock picker, and financial authority, David has led The Motley Fool’s growth into a worldwide investment and financial advisory services company. Each week David shares his insights into today's most innovative and disruptive publicly traded companies -- and how to profit from them by following his signature “Rule Breaker Investing” principles.
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Vacation Rental Success

Heather Bayer aka @CottageGuru

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Heather Bayer, author of Renting Your Recreational Property for Profit, former CEO of a highly successful cottage rental agency, and a popular blogger, hosts the Vacation Rental Success podcast. With many years experience of owning and managing multiple vacation rental properties, Heather brings her knowledge and views on every aspect of the business, together with interviews with vacation homeowners and industry experts. Heather has appeared as a guest on CTV Canada, CBC Radio, Rogers TV, a ...
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Decoding AI for Marketing

Greg Stuart, Rex Briggs

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Many speculate that marketing is the business realm poised to be fundamentally reshaped by Artificial Intelligence. However, the pressing issue is the prevalent lack of technical acumen and basic AI understanding among many marketers. Decoding AI for Marketing (DAM) aims to mend this informational void, delivering insights for the technically adept and beginners alike. We demystify AI’s intricacies and furnish hands-on, applicable marketing approaches from those leading the charge. DAM will ...
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Doug McColgin, Director of Marketing Strategy at UScellular, says that AI tools aren't enough to build an effective marketing strategy. As more and more companies adopt AI, the playing field will be leveled when it comes to productivity gains. But McColgin thinks AI can be used in more creative ways to differentiate from your competitors. He explai…
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If knowledge is power, today's show will give you superpowers! Our all-Fool cast is here to help you understand some common and not-so-common investing terms, so that you can leap tall buildings, swing from a web, and more importantly, be better investors! Are we heroes? Are we zeros? Keep score and let us know. Host: David Gardner Guests: Nick Sci…
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In this landmark episode of the Vacation Rental Success Podcast, Heather Bayer is joined by Steve Schwab, the Founder and CEO of Casago, at a truly pivotal moment - not just in his personal journey, but in the history of the vacation rental industry. As Casago steps into a groundbreaking merger with Vacasa, Steve reflects on the path that led him h…
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Tariffs, corruption, political posturing... it's no wonder that the market is crashing! But wait, is it? Back up that graph a bit and the market is still near all-time highs. In today's mailbag we strive to find happiness, maintain rational optimism, and see through the dark clouds plaguing the headlines. Plus, some tips on diversifying your portfo…
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In this powerful solo episode, Heather Bayer reflects on one of the most fundamental - and often overlooked - questions in the short-term rental space: What kind of leader are you? Through years of podcast interviews and her own journey managing STR properties, Heather unpacks the evolving nature of leadership and how it uniquely manifests in the v…
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Jen Kattula, CMO at Microsoft Advertising, has been testing out ways to improve the jobs of marketers through AI - while at the same time trying to improve organizational effectiveness. She shares use cases from Microsoft, how she thinks about agents and human intervention, and the hurdles around getting people trained up and in the habit of using …
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In remembrance of the life of George Foreman, we've gone back to the Motley Fool Radio Show vault to bring you this interview with the former heavyweight champion. From poverty to fame, sport to business, cattle to annuities, Foreman was fully invested in a life well-lived. A world-beater, a rule breaker, and by our measure, a true Fool. Host: Davi…
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We don't break the rules to cheat; we break them to improve. When conventional wisdom grows stale and unhelpful, it's the contrarians who lead the way to make investing, business, and life better. And the same is true in sports. Punting? Bunting? It's time we take a look, with the help of sports journalist, Kimball Crossley, at some sports rules th…
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Most short-term rental operators didn’t plan on becoming leaders. They started as solopreneurs - cleaning toilets one day, managing a team the next. If you’ve ever found yourself in a leadership role and thought, “How did I get here?”, this episode is for you. In this powerful and relatable conversation, Heather is joined by leadership coach Ali Ca…
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Buy me some peanuts and Cracker Jacks, because we're back at the ol' ball game with some softball, hardball, curveball, screwball, and knuckleball questions from ChatGPT. David is at the plate, taking swings at these pitches and batting you home to a smarter, happier, and richer future. Companies mentioned: AMZN, ISRG, NFLX, NVDA Host: David Gardne…
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In this special episode, we kick off our brand-new Leadership Series with someone who’s been part of this journey from the very beginning - Matt Landau. Matt’s been on the show more than 20 times over the years, but this conversation feels different. It’s deeper, more reflective, and marks a shift in how we talk about leadership in the vacation ren…
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Paul Roetzer, founder and CEO of Marketing AI Institute and Smarter X, left his agency world behind and now spends his days training marketers on how to better use AI to move their organization forward. When it comes to AI adoption at marketing organizations, there’s still a wide range of adoption - and Roetzer shares what he’s seen in terms of wha…
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Today David hosts the founder and CEO of Fair Trade USA, Paul Rice, who explains how trade can be more effective than aid in improving the world's economic issues. As consumers become more aware and more discerning about what they buy, companies that embrace conscious capitalism will enjoy an ever-growing competitive edge over those which simply lo…
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What happens when a vacation rental entrepreneur, his tech-savvy brothers, and a close-knit team of hospitality veterans come together with a mission to solve the biggest operational headaches in property management? You get Boom - the world’s first AI-powered property management system (AIPMS). In this episode, Heather sits down with Shahar Goldbo…
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It's time once again to dust off David's old writings and pull some lessons forward into the light of today. We discuss re-recs and buying stocks that you already own, annual predictions, risk ratings, and keeping a record of your investment decisions. We look back to be smarter about looking forward! (5:52) Introduction to May 2003 Issue (16:00) N…
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In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with Mark Simpson, the founder of Boostly, to discuss the practical applications of artificial intelligence (AI) for vacation rental hosts. Mark shares how AI can help streamline operations, enhance guest experiences, and optimize marketing efforts—without losing t…
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March 2025 Mailbag: Chalkboard Wisdom and Our Favorite Words March Madness isn’t just for basketball—it’s taken over Rule Breaker Investing too! In this month’s mailbag, David Gardner fields your questions and reflections with trademark Foolishness. Should you use forced rankings to evaluate your portfolio? Can AI help guide investment decisions? I…
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This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan*** >> Discover more about Guesty in the Virtual Vendor Showcase We’re back with Part 2 of my chat with AI educator and vacation re…
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It all comes down to this... the final event of March Market Cap Madness! Defending Champion Andy Cross has held off all contenders and pretenders, but young phenom and game show survivor Emily Flippen is not one to back down from a challenge. Who will win the crown for 2025? We're betting on you to come out smarter, happier, and richer as we all p…
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This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan*** >> Discover more about Guesty in the Virtual Vendor Showcase AI-Powered Marketing for Vacation Rentals: What You Need to Know W…
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Sadie Thoma, director of US B2B marketing at Google, and Derek Rodenhausen, managing director and partner at Boston Consulting Group, say that artificial intelligence is having a major impact on marketing - especially when it comes to the consumer journey. They partnered on new research that shows that the four main consumer behaviors today are str…
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We hope you've filled out your bracket because we're back with the second match of the March Market Cap Madness Final Four. Today it's the birthday boy, Bill Barker up against the survivor, Emily Flippen! Who will make it to next week's final? You will, Fool! Companies discussed: OKTA, UBER, WAL, AMGN, FUN, RKLB, GOOG, CARG, DIS, META, NOW Host: Da…
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This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan*** >> Discover more about Guesty in the Virtual Vendor Showcase Brooke Pfautz is the innovative mind behind Vintory and Comparent …
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The Olympics. The World Cup. The Super Bowl. These competitions bring the world together to back their favorite teams as they compete for the ultimate title. But March Market Cap Madness has an even bigger draw, because you not only get to root for your favorite; you get to compete! Strap in and get your pencils ready, it's go time! Companies discu…
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This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan*** >> Discover more about Guesty in the Virtual Vendor Showcase In a recent post on Linkedin, Amber Hurdle said: “Your ChatGPT Is …
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Michael Lacorazza, CMO of US Bank, and Mike Barrett, Founder and CSO at Supernatural AI, set out to break the mold: to partner together on an advertising campaign for the large financial institution using innovative AI methods and achieving fast results. If you’re interested in how to partner with AI agencies to take your work to the next level, li…
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Peter Lynch taught us to buy what we know. Can successful investing be that simple? And if we know and love the companies we own, how should we go about selling them? How are we supposed to remember why we bought these stocks in the first place? All this and more in month's mailbag! Companies Mentioned: TTD, AXON, COST, AAPL Host: David Gardner Pro…
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We’ve arrived at Week 5 of SSTIR Crazy 2025, and this might be the most critical challenge yet! Sustainability Week is here, and the stakes have never been higher for StayWise Rentals. This episode of the podcast and SSTIR Crazy Month is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect o…
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Little things can make a big difference. From spotting hidden competitive advantages in investing to rediscovering the joy in work, this episode is packed with moments that brighten our days. David shares fresh “pet perks” across investing, business, and life—including seeing through dark clouds, the thrill of entrepreneurship, and the simple magic…
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We’ve arrived at Week 4 of SSTIR Crazy 2025, and this might be the most critical challenge yet! Regulations Week is here, and the stakes have never been higher for StayWise Rentals. This episode of the podcast and SSTIR Crazy Month is sponsored by Guesty your all-in-one platform for hospitality businesses to automate and optimize every aspect of yo…
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Shiv Singh, co-founder of AI Trailblazers and the author of Marketing with AI For Dummies, knows that there’s still a huge range of adoption in the marketing space when it comes to artificial intelligence. He shares tips for those still early in their journey, and predictions for 2025 when it comes to how the marketing industry will be further upen…
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Every stock tells a story; it takes humans to find the meaning in it. This week, five Fools gather around our suddenly snowy campfire once more to share remarkable stock stories featuring lessons on patience, transformation, and long-term success. From a legendary auto auction company to the footwear brand everyone underestimated, we hope these sto…
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In this third week of SSTIR Crazy 2025, StayWise Rentals grapples with an insurance nightmare when a malicious pool party threatens to ruin their business. This episode of the podcast and SSTIR Crazy Month is sponsored by Guesty your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code…
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Some ideas stand the test of time. Others push us forward into an exciting, ever-changing future. This week, we revisit an old lesson about building bridges instead of walls, explore five cutting-edge innovations reshaping our world, dive into the power of social capital, and reflect on the hidden strength of habits—through the lens of a world-reno…
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In this second week of SSTIR Crazy 2025, StayWise Rentals grapples with a critical turning point: a safety crisis threatening their direct bookings. Easter Egg #7 [Justin] - >> SSTIR Crazy Registrants can enter this phrase in the gamification section on the app to earn big points towards the 2 VIP Tickets to VR Nation Conference, Austin, TX, April …
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