Caleb Drake
Caleb Drake has been a guest on Collecting Keys, the real estate investing podcast hosted by Mike DeHaan, Dan Austin and Dylan Koch.
Building a "Client's First" Short Term Property Management Business with Caleb Drake
Caleb Drake, an active-duty Air Force officer based near Pensacola, explains how he built a short-term rental co-hosting company to 20 units in about three months, plus a 15-agent realtor team, BRRRR and flip projects in the Midwest, and 12 long-term rentals. He breaks down his tiered management pricing, why he keeps cleaners and money handling off his books to avoid Florida's broker license requirement, and how he uses VAs and clearly defined partnerships to run multiple businesses around a full-time military job.
Key takeaways
- Caleb's co-hosting model charges 10%, 15%, or 18% of gross, plus a pass-through $50 technology fee for PriceLabs and Hospitable at cost, with no upcharges on cleaning.
- Because he never touches the owners' money (cleaners invoice owners directly, he invoices monthly), he avoids Florida's requirement for a broker's license to manage property.
- Short-term management doesn't pencil below roughly 10-15 units because of the cost of building VA and cleaner teams; 20 units currently take 10-15 hours a week, with a target of about 5 hours once systems mature.
- His differentiator against 200-unit companies charging 22-25% is transparent pricing and actual communication; he plans to cap at 40-60 units to keep the boutique service level.