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All Forum Posts by: Miles Hobson

Miles Hobson has started 3 posts and replied 17 times.

Post: FREE Online Short-Term Rental Conference

Miles Hobson
Property Manager
Pro Member
Posted
  • Toronto
  • Posts 17
  • Votes 12

Don't miss out - the Hospitable Online Conference is back! Register for Hospitable's free short-term rental conference happening January 28-29, 2025. Register now and receive the recordings straight to your inbox, even if you can't make it there live! This year, Hospitable is focused on bringing you top insights from successful short-term rental hosts only, including Avery Carl, Zoey Berghoff, Seth Balogh, and more!

Post: Hiring: Accountant in Residence with Hospitable (Remote)

Miles Hobson
Property Manager
Pro Member
Posted
  • Toronto
  • Posts 17
  • Votes 12

Hospitable is hiring! And not just for any ordinary accounting role. The Accountant in Residence will impact the products that we build for our customers.

Hospitable is building a moat with fintech solutions tailored to the short-term rental industry. We handle an ever growing volume of our customer's revenue and payment flow: processing direct bookings as the merchant of record, distributing property manager's payouts to their owners, and soon facilitating a marketplace of service providers. Reducing the tax and compliance burden on our hosts is a critical step for our mission to make short-term rentals trivial to operate.

Experience in lodging taxes is a must-have!

To accomplish this, you will:

  • Support Product & Engineering for product and feature development.
  • Support Finance & Direct team in payment of short-term rentals, sales and lodging taxes in the US, determining a strategy for global roll out.
  • Work with Marketing and Support to create accounting and taxes related content and events, and educate our customers.
  • Work with Sales & Professional Services for supporting customers in getting the best setup (Owners or Managers).


What we are looking for:

  • Tax expertise: Deep understanding of sales and lodging tax calculation, filing, and remittance in the US market.
  • Accounting fluency: Proficient with relevant topics like 1099-K reporting, material participation, and cost segregation.
  • Industry experience: Awareness of the current short-term rental legal and compliance landscape.
  • Ownership: Take responsibility and pride to deliver best-in-class outcomes.
  • Communication: Excellent communication skills, with the ability to break down complicated concepts, like the fact that Andrew's favorite ice cream is pistachio.
  • Passion: Obsessive drive to deliver value to our customers and help them succeed.
  • Very special kudos if you are a short-term rental/Airbnb host.
  • Everything else is a lovely bonus that we're excited to hear about!

Post: Guesty / hostaway / hospitable?? Help!

Miles Hobson
Property Manager
Pro Member
Posted
  • Toronto
  • Posts 17
  • Votes 12

@Paul Stewart it's not on our roadmap yet, so I can't give you a timeline, unfortunately. I think you may have already upvoted the feature on our feedback page but you're welcome to find other hosts that want it and encourage them to upvote it too to signal to our product team that there is high demand for the feature https://feedback.hospitable.com/p/marriott-home-and-villas-i...

Post: Guesty / hostaway / hospitable?? Help!

Miles Hobson
Property Manager
Pro Member
Posted
  • Toronto
  • Posts 17
  • Votes 12

Hey I work for Hospitable and happy to answer any questions you might have. I can get you booked for a demo call to answer any questions or concerns you have and we'll tell you honestly if we're not the right solution for you. No need to jump on a call for a quote or anything though (pricing is here) and we're transparent with feedback from hosts and what we're building (we host public bi-weekly Town Halls where you can ask us anything).

Post: Offshore Airbnb Management

Miles Hobson
Property Manager
Pro Member
Posted
  • Toronto
  • Posts 17
  • Votes 12

Hey @Ashish G., I know some Hospitable.com customers utilize Extenteam.com. Their VAs will typically use Hospitable to manage your account and automate as much as possible but are there to answer one-to-one questions when a human touch is needed

Post: What's your best piece of advice or tip when starting out managing a STR?

Miles Hobson
Property Manager
Pro Member
Posted
  • Toronto
  • Posts 17
  • Votes 12

Thanks for the Hospitable.com shout-out @Brian Barch!

Congrats on your first STR @Jenny Milu. Since I work for Hospitable, I of course have to say that communication is key. Sending guests the right messages at the right time can transform a guest's stay. Send them the lock code in pre-check-in instructions and at time of check-in (because not everyone reads the full message first time round), and automate a "how are you liking the place?" message after the guest's first night. These are just two simple ways to enhance the guest experience and get you more 5-star reviews. Seems simple but it's highly effective.

Post: Short term rental best advice

Miles Hobson
Property Manager
Pro Member
Posted
  • Toronto
  • Posts 17
  • Votes 12

I'm biased because I work for Hospitable.com but a top tip for short-term rentals would be to look at tools that help you to automate hosting. STRs are traditionally seen as a lot more work than LTR because of the guest turnover but with tools that use AI to automate messages and send guests smart lock door codes at the right time...short-term can be almost as easy as long-term. 

Post: Negative Cashflow - STR

Miles Hobson
Property Manager
Pro Member
Posted
  • Toronto
  • Posts 17
  • Votes 12

I agree with all of those points @Michael Calvey!
I'd also ask if you're using a dynamic pricing tool such as PriceLabs @Joseph Shuster? Are you fully booked but maybe not charging as much as you could or are you failing to fill your calendar (maybe you're not pricing competitively enough).
If you aren't booking up your property then a tool like RankBreeze could help you increase exposure of your Airbnb listing while also doing some of those strategies Mike suggested.

Post: STR Networking Events - Orlando, Atlanta, Austin, and LA

Miles Hobson
Property Manager
Pro Member
Posted
  • Toronto
  • Posts 17
  • Votes 12

Hopefully see you there @John Underwood and thanks for the Greenville suggestion!

Post: STR Networking Events - Orlando, Atlanta, Austin, and LA

Miles Hobson
Property Manager
Pro Member
Posted
  • Toronto
  • Posts 17
  • Votes 12
Quote from @KiKi Wood:

You should do one in the Indianapolis area! 


Believe me, it was tough to narrow down the cities for this year. All going well we'll try to do again in Spring 2025 and hit up Indianapolis