The Boostly Spotlight: Garrett Brown from BiggerPockets

The Boostly Podcast

Host: Mark Simpson
Date: November 1, 2025

Episode Overview

In this engaging episode, Mark Simpson interviews Garrett Brown, the driving force behind BiggerPockets’ short-term rental (STR) content and a successful hands-on STR investor. The conversation delves deep into Garrett’s journey from hotel management to real estate investing, his lessons learned building a thriving glamping business, and a wealth of actionable strategies for hosts looking to secure more direct bookings and future-proof their hospitality businesses beyond reliance on OTAs such as Airbnb.

Garrett Brown’s Journey into STR (01:00-04:17)

• Background:
  Garrett graduated from the Conrad Hilton College (University of Houston) with intentions for restaurant management but shifted focus to real estate and investing.
• Entry into STR:
  Flipped houses, bought multi-family properties, and in 2018, started exploring STRs—leveraging his hotel background.
• First STR Investment:
  Bought three condos in Houston in 2019, generated $1k-$2k per unit monthly.
• Expansion:
  Founded Cameron Ranch Glamping in 2021—now over 25 glamping units across Texas, grossing $1M+/year.
• Role at BiggerPockets:
  Became the face of their STR education, building out content and resources as demand in the community shifted.

"I was making an extra, you know, each unit was giving me like $1,000 or $2,000 in my pocket each month."
— Garrett Brown, (03:05)

Frequently Asked STR Questions at BiggerPockets (05:13–07:36)

• Top Questions:

  1. “What market should I invest in?”
  2. “How do I make more money with the property I already have?”
  3. “How do I take advantage of the short term rental tax (bonus depreciation) opportunities?”

• On Tax Benefits:

  • Describes the legitimate short term rental ‘loophole’ in the IRS tax code (not advice—always consult a CPA).

"If you buy a property this year, put it into use... and you actively manage it...you can offset some of those losses by doing a cost segregation study."
— Garrett Brown, (06:39)

Direct Bookings & SEO Mastery (08:06–13:59)

• Direct Booking Sites:
  • Emphasizes patience: took 2.5 years to reach 75% direct bookings.
  • Importance of SEO: site must target specific local keywords; success takes time and consistent effort.

"Don’t get discouraged...It took me two and a half years to get to 75% direct bookings."
— Garrett Brown, (08:26)

• Niche Down for Visibility:
  • Example: Targeting “Lake Livingston vacation rentals” to dominate search results over OTAs in local SERPs.
  • Blogs are powerful—evergreen content brings high-performing, recurring traffic.

"People think blogs are dead...We wrote [about] romantic couples getaways in Texas and it was our third highest-performing link."
— Garrett, (12:00)

Automation, Upfront Effort & What New Hosts Overlook (13:59–17:38)

• Reality Check:
  • STR isn’t instant passive income; requires initial work and investment.
  • Today’s tech (automations, AI) allows for 80-90% automation if properly set up.

"It takes a lot of work upfront... but for the most part it can be kind of automated."
— Garrett, (14:07)

• Crucial Early Steps:
  • Get systems in place—software, messaging, operations.
  • Success builds through “reps” and continuous refinement.

Lessons from Glamping (17:38–20:15)

• Unique Challenges:
  • Landscape/infrastructure upkeep more demanding (and expensive) than many anticipate.
  • Don’t go cheap: lower-quality structures lead to high replacement/guest dissatisfaction costs.

"Whatever you’re thinking those utilities and infrastructure costs are—go ahead and triple that."
— Garrett, (18:26)

• Advice:
  • Hard-sided structures are more durable and valuable than soft-sided ones.
  • Visit successful comps before committing to a business model.

Finding STR Niches & Market Gaps (20:44–26:57)

• Luxury vs. Mass Market:

  • High-end romantic glamping performs well (hot tubs, saunas, unique amenities), but luxury segment is saturating.
  • Mid-priced offerings can capture a broader audience; conversion rates often higher at $150–$300/night.

• Pet-Centric Properties:

  • Major overlooked opportunity is the “dog centric” (pet-centric) rental, truly catering to pets (not just tolerating them).
  • Social media viral potential when combining cool properties and pets.

"I think that a dog-centric or pet-centric...place, where you’re catering to the dog more than the person, could possibly crush it and explode."
— Garrett, (25:46)

The Role of AI in STR & Enhancing Guest Experience (28:17–34:13)

• AI as a Tool:

  • Not a replacement for humans, but a powerful tool for efficiency.
  • Hosting automation with products like Host Buddy AI and dynamic pricing tools.

• Unique AI Applications:

  • Garrett’s VA uses AI to generate custom guest songs for special occasions—surprising and delighting guests.
  • AI-curated itineraries based on guest interests.

"We send them this link and tell them we made this special song for them...The amount of people that have commented...it’s amazing."
— Garrett, (31:04)

Favorite Tech Stack & Tools (36:01–37:32)

• Core “Holy Trinity”:

  • Lodgify (PMS): “a lot of them out there that are really good.”
  • Pricelabs (Dynamic Pricing): “definitely [the] best.”
  • Turno (Cleaning Ops): “cleaning, handy things there.”

• Team/Communication:

  • OpenPhone: For VOIP team lines, integrates with Host Buddy.
  • Discord: For team communication (free alternative to Slack).
  • Asana: Task management.
  • Breezeway: For ops/safety (tested).

"If you have [these] in line, you’re going to be pretty much ready to rock and roll all around."
— Garrett, (37:27)

Defining Success & Big-Picture Advice (38:40–41:34)

• STR is Adaptable:
  • Whether your goal is funding a personal vacation home or building a 100+ property portfolio, STR can fit.
  • Success is individual: design a business that serves your 5–10 year vision.

"The really cool thing about short term rentals is you—success is what it is to you in it...That’s the beauty in it."
— Garrett, (41:23)

• Core Tactics to Ignore Noise:
  • Focus on your own goals over industry hype.
  • Master your systems and guest experience—everything else follows.

Memorable Quotes & Moments

• On early restaurant experience:
  "Everyone should have to go and work in hospitality, even in a restaurant or in a home, and have to do this because it’d be so much nicer for people who haven’t worked in it."
  — Mark Simpson, (04:44)

• Automation & Guest Messages:
  "You need the human touch—give a guest a digital hug."
  — Garrett Brown, (13:59, paraphrased)

• On AI-powered guest delight:
  "People have been like, oh my god, she has such an amazing voice [on the AI song]. But it’s just one of those things that’s like: what are things that other people aren’t doing?"
  — Garrett, (31:22)

Where to Find Garrett Brown

• Social:
  • Instagram/TikTok: @GarrettBrownRE
  • YouTube: Bigger Stays (via BiggerPockets)
• BiggerPockets:
  • Short-term rental community, blog, and forums.

Takeaway Action Steps

• Invest time, not just money, into your direct booking strategy—SEO and niche targeting are key.
• Be patient: compounding effort over years will deliver.
• Don’t underestimate upfront work—automation pays off after initial grind.
• Seriously consider serving pet-centric and mid-priced market gaps.
• Leverage AI for both efficiency and unique, memorable guest experiences.
• Define your own success—STR can fit almost any lifestyle or investment goal.

(For full links and resources, check the podcast show notes.)