What happens when a seasoned Wall Street portfolio manager enters the short-term rental game? In this episode, we sit down with Andy Newman, CEO of Newman Hospitality, to unpack the surprising parallels between financial portfolio management and building a successful STR (short-term rental) business.
With over a decade of experience in both banking and vacation rentals, Andy shares what most STR operators overlook — and how applying investment discipline, risk management, and diversification principles can be the difference between scaling sustainably and burning out.
Whether you’re an investor, operator, or just STR-curious, this episode delivers practical insights and honest reflections you won’t hear anywhere else.
What You'll Learn:
The “1,500-Mile Rule” for reducing market and seasonality risk in your STR portfolio
Why most people buy vacation rentals in the wrong places — and how to fix it
The marketing mistake that slowed Andy’s growth for 5 years
How to diversify STR investments like a true portfolio manager
Why Vacasa’s national scaling strategy failed — and what’s working instead
How to evolve from operator to CEO (and build a team that stays)