Quitting My Job for Short-Term Rentals (Everything I Learned) | Jake Martin

What does it really take to break free from the 9-to-5 and build a thriving short-term rental business? In this episode, We sit down with Jake Martin, a former corporate professional who left the security of his W2 job to chase a different kind of success—one built on freedom, flexibility, and financial independence. Jake opens up about the real story behind his transition: the fears, the failures, and the big wins. From learning the ropes of vacation rental investing in San Diego to managing multiple properties and navigating tough decisions, Jake shares hard-earned lessons and no-fluff advice for anyone dreaming of a similar leap. Whether you're exploring co-hosting, thinking about your first property, or simply craving a raw and honest take on entrepreneurship, this episode delivers both inspiration and actionable insights. 🎧 Tune in and get ready to rethink what’s possible. Things we discussed in this episode: Jake Martin’s decision to leave his corporate job and pursue real estate investing.The impact of corporate layoffs and lack of loyalty on career choices.Early investments in syndication deals and short-term rentals.The process and challenges of renovating and managing properties during COVID.Transitioning personal residences into income-generating short-term rentals.The financial strategy of covering mortgages through rental income.Building and growing a co-hosting business (Lodge and Leisure) in San Diego.Methods for finding and acquiring new property management clients.Common issues faced by property owners, such as maintenance, design, and guest experience.Advice for aspiring entrepreneurs and real estate investors, emphasizing adaptability and problem-solving. Get in touch with Jake: Email - ⁠⁠⁠⁠⁠⁠info@lodgeandleisure.com LinkedIn - ⁠⁠⁠⁠⁠https://www.linkedin.com/in/jacob-r-martin Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.lodgeandleisure.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Entrepreneurship #VacationRentals #PropertyManagement #CoHosting #FinancialFreedom #BusinessGrowth #AirbnbHost #InvestSmart Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first 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 Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Jason Muth on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠