How To “Ask for Money” with Bill Allen (Episode 327)

Financing with Family: An Open-Minded Exploration of Creative STR Financing Opportunities

Today’s expert guest is Bill Allen in an interview conducted during TFVCON2023. Bill’s informative presentation inspired and empowered attendees to seek out creative financing outside of the typical bank structure. It may sound scary, but the logic behind this shift will surprise you!

Amid the buzz and bustle of the conference atmosphere, Bill gets tactical with tools to shift your mindset from lender to partner, from building a transaction to building a relationship. He also shares wisdom on what to do when it goes wrong, and how to hack your process to avoid failure (at least in the traditional sense) altogether.

It’s an eye opening perspective, to be sure. Check out the below linked related episodes for more information on these concepts, and keep an eye out for upcoming episodes in this area as more and more short-term hosts look to pull the plug on their short-term rental dreams. 

(00:01:23) #STRShareSunday: @theadamsfarmhousevt

  • Celebrating three generations of owners 
  • Leaning into snow coverage and ski season 
  • Shout out to amazing wallpaper 

(00:04:11) Exploring the Idea of Family/Friendly Financing

(00:06:52) Mastering the Mindset of Creative STR Financing

  • Everything is 80% tactics and 20% tactics 
  • Reframing your question: Lender vs. partner
  • Turning a transaction into a relationship

(00:10:39) What Happens When an STR Deal Doesn’t Work Out?

  • Think of it like a bank and cover your losses
  • Accepting risk and being transparent
  • Why continue to make the banks rich?

(00:15:52) Changing How We View & Use Banks

Download a transcript of this episode.




The Adams Farmhouse is a dreamy ski weekend retreat in Vermont. This charming farmhouse is the ideal base for winter adventures and cozy staycations – equipped with a working nook and some truly amazing wallpaper. Surrounded by beautiful mountain views, you can spend your day conquering the slopes; it’s a true winter wonderland. Kudos to Becca and all three generations of her family that make this property so special.

We would love to feature YOU, so don’t forget to use #STRShareSunday to get your chance!

Together, Annette & Sarah are the dynamic duo behind the wildly popular podcast Thanks For Visiting, co-creators of the Hosting Business Mastery Method, & seasoned short-term-rental hosts.

Meet Your Hosts


keep listening...