SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips

LEVEL UP Your Airbnb Business in Your Early 20s | Bailey Kramer


Listen Later

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


    *****


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

    Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide.


    *****

    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


    *****


    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!

    ...more
    View all episodesView all episodes
    Download on the App Store

    SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting TipsBy Airbnb Superhost Jason Muth + Rory Gill

    • 4.9
    • 4.9
    • 4.9
    • 4.9
    • 4.9

    4.9

    39 ratings


    More shows like SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips

    View all
    BiggerPockets Real Estate Podcast by BiggerPockets

    BiggerPockets Real Estate Podcast

    16,773 Listeners

    Real Wealth Show: Real Estate Investing Podcast by Kathy Fettke / RealWealth

    Real Wealth Show: Real Estate Investing Podcast

    398 Listeners

    Rental Income Podcast With Dan Lane by Rental Income Podcast

    Rental Income Podcast With Dan Lane

    827 Listeners

    Get Rich Education by Real Estate Investing with Keith Weinhold

    Get Rich Education

    609 Listeners

    Passive Real Estate Investing by Real Estate Investing with Marco Santarelli, Investor and Entrepreneur.

    Passive Real Estate Investing

    975 Listeners

    Tax Smart Real Estate Investors Podcast by Hall CPA

    Tax Smart Real Estate Investors Podcast

    414 Listeners

    BiggerPockets Money Podcast by BiggerPockets

    BiggerPockets Money Podcast

    3,069 Listeners

    Real Estate Investing with Coach Carson by Chad Coach Carson

    Real Estate Investing with Coach Carson

    609 Listeners

    Thanks For Visiting by Airbnb Superhosts Annette Grant & Sarah Karakaian

    Thanks For Visiting

    580 Listeners

    Real Estate Rookie by BiggerPockets

    Real Estate Rookie

    1,843 Listeners

    Short Term Rental Secrets Podcast by MICHAEL SJOGREN

    Short Term Rental Secrets Podcast

    16 Listeners

    PassivePockets: The Passive Real Estate Investing Show by PassivePockets, Jim Pfeifer, and Left Field Investors

    PassivePockets: The Passive Real Estate Investing Show

    137 Listeners

    The Short Term Show by 8 Figure Airbnb and Short Term Rental Real Estate Investor Avery Carl

    The Short Term Show

    442 Listeners

    On The Market by BiggerPockets

    On The Market

    896 Listeners

    The David Greene Show by David Greene

    The David Greene Show

    690 Listeners