In this engaging episode, we are excited to introduce Bailey Kramer, a 23-year-old real estate entrepreneur who has already carved out an impressive space in the world of short-term rentals and co-hosting. Bailey's real estate journey began in college after reading Rich Dad, Poor Dad, a book that ignited his entrepreneurial spirit. From there, he dove headfirst into various forms of real estate investing, including apartment complexes and fix-and-flips, before finding his true passion and niche in short-term rentals. Leveraging platforms like Airbnb, Bailey quickly built a portfolio that generates passive income and expanded into co-hosting, helping other property owners turn their spaces into successful vacation rentals.

Despite his young age, Bailey has navigated the challenges of being an entrepreneur in an industry often dominated by older, more experienced investors. His resilience and sharp focus have helped him overcome hurdles like skepticism and imposter syndrome. In this episode, Bailey shares his invaluable insights, from creative financing strategies to effective co-hosting methods, and the importance of staying focused on your goals. Whether you're an experienced real estate investor or just starting your journey, Bailey’s story will inspire and equip you with practical tips to thrive in the short-term rental market. Join us as we explore the highs and lows of his remarkable success—all achieved before his 24th birthday!

Things we discussed in this episode:

• Bailey's journey into real estate, starting with reading "Rich Dad, Poor Dad" in college


• His initial focus on apartment complexes and the pivot to single-family properties


• The creative financing strategies he used to acquire his first few investment properties


• How he got started in the short-term rental business and the transition to co-hosting


• The challenges he faced as a young entrepreneur, including "imposter syndrome"


• The mixed reactions he received from older, more traditional real estate investors


• The importance of finding your niche and super-serving a specific target market


• The differences in mindset and approach between younger and older real estate investors


• The lessons he learned from partnership mistakes and the importance of client selection


• His decision to drop out of college to focus full-time on his co-hosting business

Get in touch with Bailey:

Youtube - https://www.youtube.com/channel/UC743mBwYcmpRdxMi8juvJ4g

Linkedin - https://www.linkedin.com/in/bailey--kramer/

Instagram - https://www.instagram.com/the_bailey_kramer

Facebook - https://www.facebook.com/bailey.kramer.986

#smartstayshow #realestate #realestateinvesting #realestateinvestor #realestatelaw #realestateagent #shorttermrentals #airbnbhosting #cohosting #entrepreneurship #businessgrowth #mediumtermrentals #insurancecontracts #chasingdreams #youngentrepreneurs #biggerpockets

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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for another episode of SmartStay Show!

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SmartStay Show Website and on Instagram and YouTube

Prideaway Stays Website and on Facebook and LinkedIn

SmartStay Coaching Website and on Instagram

Straightforward Short-Term Rentals Website

Attorney Rory Gill on LinkedIn

Jason Muth on LinkedIn

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This podcast and these show notes are not legal advice, but we hope you find both entertaining and informative.

Hospitality.FM

SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!