Short Term Rental Secrets Podcast

Ep 255 - How Two Investors Scaled from Co-Living to 80 STRs with Blake Anthony Carter and Jeremy Courtney

Aug 18, 2025
Blake Anthony Carter and Jeremy Courtney, seasoned real estate and property management experts, share their incredible journey from co-living spaces to managing 80 short-term rental properties. They discuss their strategic pivot, emphasizing the importance of systems and partnerships in scaling. The duo also delves into lessons learned about market timing, staying focused during rapid growth, and the value of hands-on evaluation of their properties. Their insights on adapting business structures reveal how challenges become easier with experience.
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ANECDOTE

From Three Rooms To A Management Business

  • Blake and Jeremy started by managing three houses rented by the room and charged $500 to manage 18 rooms to get traction.
  • That early co-living gig taught them operations and led to meetups and their Airbnb management pivot.
ANECDOTE

Hockey-Stick Growth That Broke Them

  • They grew to ~98 properties in a year by running meetups and posting heavily on social media.
  • Rapid growth overwhelmed them without systems, so they later cut bad clients and refocused operations.
ADVICE

Fire Bad Clients Quickly

  • Cut unprofitable properties and difficult owners as soon as overhead shows they're not worth it.
  • Use a minimum profit-after-overhead threshold and drop owners who create drag on your operations.
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