Bailey Kramer bought his first investment property at 20 after reading Rich Dad Poor Dad and cold-calling vacant homes. Now 21, he co-hosts seven short-term rentals across four states and manages two giant vacation properties that sleep 20-plus guests and gross $200,000 to $300,000 each per year - one of them hosts weddings on a chain of lakes in Illinois. Bailey charges $2,100 a night in summer, books mostly through Vrbo to dodge Airbnb's new refund policy, and raised $180,000 from mastermind investors to buy his first STR with seller financing.
The episode covers Bailey's path from college dropout to multi-state STR operator: structuring co-host deals at 10-20% of gross, screening out high-school prom after-parties, using TikTok controversy to grow his following, and automating upsells with Hospitable's smart messages that have earned him thousands in extra nights. Myka and Bailey discuss the new Airbnb 72-hour complaint window, why cleaners matter more than ever, and how charging guests slightly more than the cleaning bill creates a damage buffer without filing petty claims.
Work with us. Interested in professional management or consulting?
Myka — Sharebnb: www.sharebnb.com
Steve — Argest Rentals: www.ArgestRentals.com
Sign up for PadSplit with Steve's link and get a free 1-on-1 PadSplit strategy call with Stevie Stacks: padsplit.com/hosts
Myka's other podcast, Entrepremarriage — building wealth without losing the marriage: youtube.com/@Entrepremarriage
All our links: linktr.ee/liveletthrive
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