E202 - From W2 to 11 STRs: Brandon Wood’s Approach to Sustainable Scaling

📄 EPISODE SUMMARY

In this episode of *The Peak Season Podcast*, Luke and Tyler sit down with *Brandon Wood*, founder of Adventure Nest, for a candid conversation about what it actually looks like to scale a short-term rental portfolio without losing your sanity—or your family in the process.

Brandon shares his journey from a demanding W2 career into full-time short-term rentals, including how he went from a single property to operating *11 high-quality STRs across multiple states*. Rather than chasing door count, Brandon takes a deliberate quality-over-quantity approach—prioritizing strong operations, protected markets, and sustainable income over flashy amenities and constant expansion.

They also get real about masterminds and coaching groups (the good, the bad, and the expensive), why smaller accountability circles often outperform massive paid communities, and how too much “learning mode” can quietly become procrastination.

Brandon unpacks hard lessons from early investments, including buying in overly saturated markets, misreading post-COVID data, and trusting large property management companies that dramatically underperformed. Along the way, he explains why he now _leans into regulation_, how data shaped his decision-making, and what finally pushed him to leave his W2—without the dramatic walkout.

This is Part 1 of a two-part interview, setting the foundation for how Brandon thinks about time, money, family, and long-term scalability in the STR business.



Find Brandon - http://www.myadventurenest.com

Work with Tyler & Luke - http://www.upstreamvacations.com




🎯 KEY TAKEAWAYS

Why quality beats door count when building a long-term STR business
How regulation can actually protect your revenue and asset
Why most large property management companies underperform
How small accountability groups can outperform expensive masterminds
The danger of staying in “learning mode” too long
What it really takes to replace a W2 with STR income
Why setup is the hard part—and operations get easier with reps
Co-hosting strategies Brandon used to land early clients



⏱️ EPISODE CHAPTERS

00:00 – Introduction & Guest Overview
01:54 – Brandon’s Entry Into Short-Term Rentals
05:42 – Masterminds: What Helped and What Didn’t
07:28 – Accountability, Networking, and Smaller Groups
10:15 – Learning vs. Execution (and When to Switch Gears)
12:50 – Brandon’s Background and W2 Career
13:19 – Early Successes and Costly Mistakes
20:34 – Building a Sustainable Portfolio
23:06 – Regulation as a Competitive Advantage
25:43 – Lessons from Tennessee & Saturated Markets
27:26 – Expanding Into New, Niche Markets
33:21 – Leaving the W2 World (Without the Drama)
37:20 – How Brandon Lands Co-Hosting Clients


🔮 WHAT’S COMING IN PART 2

In Part 2, Brandon goes deeper into his underwriting process, how he evaluates markets, and how he’s scaling co-hosting without building a bloated property management machine.




⚠️ DISCLAIMER

The information shared in this podcast is for educational and informational purposes only and should not be considered financial, legal, or tax advice. Every short-term rental business, market, and personal financial situation is different.