How I Grew to 11 STRs in Months (Full Breakdown) | Chachi Horgan

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

Ever wonder what it really takes to pack up your life, move to a new city, and build a short-term rental business from scratch?

In this episode, We sat down with my friend Chachi Horgan — a former real estate agent from Maine who took a leap, moved to Florida, and built Roam Ready Vacation Rentals, scaling to 11 properties in less than two years.

We talk about everything — the mindset it took to start over, the power of building a solid network, what it’s like navigating a new market, and why learning to delegate is absolutely critical if you want to grow. Chachi also shares how coaching lacrosse and a love of personal development shaped how he runs his business today.

If you're thinking about starting a vacation rental business — or scaling the one you already have — this one's loaded with real stories, raw insights, and some seriously motivating perspective.

Things we discussed in this episode:

• Chachi's transition from real estate agent to short-term rental business owner in Florida

• The importance of networking and building relationships in a new community

• Strategies for analyzing and selecting properties using tools like AirDNA and PriceLabs

• The challenges of scaling a business and delegating tasks effectively

• Mindset development and personal growth through reading business and self-help books

• Dealing with seasonality in short-term rental markets

• The value of having a growth mindset and continuous improvement

• Expanding business operations across multiple markets (Florida and Maine)

• The role of virtual assistants and team members in business growth

• Leveraging coaching and athletic experience in developing business skills and mindset training

Get in touch with Chachi:

Facebook - ⁠https://www.facebook.com/chachi.horgan

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

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://roamreadyvacationrentals.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbInvestment #RealEstateSuccess #PropertyInvesting #STRStrategy #OffMarketDeals #AirbnbTips #RealEstateCoaching #PassiveIncome #PropertyManagement

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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!