E203 - Brandon Wood Part 2

The Peak Season Podcast – Part 2 with Brandon Wood

In Part Two of our conversation, Brandon Wood goes deep on what actually powers a scalable short-term rental operation—without burning out or over-engineering too early.

We cover Brandon’s full tech stack (from PMS to insurance), how he thinks about outsourcing versus control, and why time is the real bottleneck most operators ignore. Brandon also shares real-world customer service stories that should’ve been one-star disasters—but turned into five-star wins, dinner included.

This episode is a practical, no-nonsense look at what works once you’re past your first couple of properties—and what not to take on, even when the money looks good.

----------------------------------------


CHAPTERS / TIMESTAMPS

00:00 – Intro: Part Two with Brandon Wood
00:48 – Scaling to 15 properties without losing sanity
01:07 – Airbnb & VRBO only: delaying direct bookings on purpose
02:30 – Hospitable as a PMS (and why AI messaging isn’t quite there yet)
03:45 – Custom reporting, Canva, and staying hands-on
04:30 – Task management and staying above water
05:10 – PriceLabs vs outsourced revenue management
06:10 – Buying back time with outsourced pricing
06:55 – Digital guidebooks & search ranking tools
07:30 – Guest damage insurance: why AirCover isn’t enough
07:52 – How guest-paid incidental insurance works
08:34 – Insurance integrations and claim workflow
10:00 – Outsourcing bookkeeping (and why it pays for itself)
11:45 – Cleaning platforms vs keeping great cleaners
13:12 – Collecting guest data before you’re “ready”
14:20 – Outdoor security, cameras, and real-world mountain problems
15:00 – Noise, smoke, and occupancy monitoring
15:53 – Auto-rebooting WiFi routers (a must-have for remote properties)
17:47 – Rapid fire: biggest win in hospitality
18:02 – Bear, broken windshield, and a five-star review
22:36 – Why bad situations create the best reviews
23:31 – Nightmare scenarios and emotional control
24:23 – Taking on too much (accidental GC lessons)
28:09 – Learning when to say no to clients
31:26 – Podcast recommendations for STR operators
33:37 – Book recommendations for business and life
35:16 – How to connect with Brandon

----------------------------------------


🔌 AUTOMATIC WIFI REBOOTER (MENTIONED IN EPISODE)

One of the simplest “why didn’t I do this sooner” upgrades for remote or rural properties.

Automatic WiFi Rebooter (Amazon):
https://www.amazon.com/Keep-Connect-D...

This device automatically power-cycles your router when the internet drops—often fixing issues *before guests even notice*. Especially useful for mountain, lake, and off-the-beaten-path markets.

----------------------------------------


DISCLAIMER

The views and opinions expressed in this episode are those of the hosts and guests and do not constitute legal, financial, tax, or investment advice. All examples discussed are for informational and educational purposes only. Every short-term rental market, property, and investor situation is different—listeners should conduct their own due diligence and consult with qualified professionals before making business decisions.