Caleb Shore - Airbnb Investor & Consultant

💰 $2.6MM/year Host / 85% Occupancy in ‘25
| Helping Real Estate investors find, purchase & manage Short Term Rentals. 🎁 Airbnb Freebies 👇🏼

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

Am I weird?

I check my credit score and bank balance daily 👀

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

Reminder: buy the place that has the X factor

Roof top pool
Right in front of a park
The view that you can’t copy

Yes, those are more expensive but worth it.

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

How is the stock market at all time highs when we’re at war 🤔 something doesn’t add up

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

That’s the difference between:
“owning an Airbnb” vs
using Airbnb as a tax strategy.

Not advice — talk to your CPA.

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

Most high earners are overpaying taxes…
because they don’t understand this tax “loophole”.

If your Airbnb is structured right,
your losses may NOT be passive.

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

That means:
👉 You can potentially offset W2 or business income
👉 Pair it with cost seg + depreciation
👉 Create serious tax savings

The catch:

Avg stay ~7 days or less
You materially participate (100–500 hrs)
You actually run it like a business

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

@BiziEdit For sure you hit the nail on the head.
Side note but cool service you provide. I built something similar

https://t.co/BH4HHrzEPE for Airbnb photos

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

🧵 Most Airbnb hosts don’t lose money because of pricing.
They lose money because of missed details.

Comment “CHECKLIST” and I’ll send it to you!

Broken items.
Bad turnovers.
Inconsistent standards.

And every small miss =
→ worse reviews
→ lower conversion
→ lost revenue

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

What to check before EVERY check-in
How to catch problems before guests do

If you want cleaner operations, better reviews, and fewer headaches…

Comment “CHECKLIST” and I’ll send it to you.

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

AI things I’m working on in my business:

- listing optimizer (automate as much as possible). Tool below - open to beta.

- rev manager (make pricelabs tweaks for me).

- daily brief (collect all tools and prioritize my day). Integrates slack, email, asana, calendar.

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

Listing optimizer beta: https://t.co/b0Z1ZDEqpH

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

AI things I’m working on in my business:

- listing optimizer (automate as much as possible). Tool below - open to beta.

- rev manager (make pricelabs tweaks for me).

- daily brief (collect all tools and prioritize my day). Integrates slack, email, asana, calendar.

[Khairallah AL-Awady @eng_khairallah1]

🚨 Anthropic's own team just showed how to actually prompt Claude.

24 minutes. free. from the people who built it.

watch the workshop. bookmark it.

worth more than every $300 course you almost bought.

you've been using Claude without knowing 40 of its prompts.

Then read the guide below.

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

Anyone with an index finger ring I immediately lose trust

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

Don’t stay up late for things you wouldn’t wake up early for

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

Content breakdown:

70% commodity content (7 lessons to do X)

30% perspective content (your unique perspective)

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

Once you have momentum (business, life/etc), just get the hell out of the way!

[Caleb Shore - Airbnb Investor & Consultant @CalebWShore]

67% of first-time Airbnb hosts never break even.
Not bad luck. Bad math.

Here are the 4 things I check before recommending ANY property to an investor: