Trailblazer Show

Wilson Liang is a physician assistant, investor, and founder of Finance Hospital, where he helps healthcare professionals build wealth beyond their W-2 income.In this episode, I sit down with Wilson to talk about why so many high-income earners still feel financially trapped despite making great money, how he and his wife reached Coast FIRE in their early 30s, and why building passive income creates options long before traditional retirement.We dive into Coast FIRE, private lending, real estate investing, brokerage accounts, and the biggest financial mistakes professionals make when planning for retirement.This conversation is about creating financial flexibility, building wealth intentionally, and designing a life where work becomes a choice and not a necessity.

Adam and Micah started exactly where many real estate investors do: buying short-term rentals and chasing financial freedom one property at a time.Today, they're building Comeback Hospitality after acquiring their first boutique hotel in Page, Arizona, transforming an underperforming property into an experiential destination while sharing every win, setback, and lesson publicly along the way.In this episode, we break down why they believe hospitality is one of the biggest opportunities over the next decade, how they found and negotiated a hotel at a significant discount, raising capital for their first commercial acquisition, and the systems they're building to scale beyond Airbnb.This conversation is about thinking beyond small deals, creating value where others don't see it, and building assets that compound for decades.

Ben Wolff is the co-founder of Onera, one of the most recognizable brands in experiential hospitality. After helping scale Onera into a portfolio of unique landscape hotels with $500+ ADRs and industry-leading occupancy, he sold Onera Fredericksburg to a publicly traded REIT and is now developing Baya, a tropical wellness resort in South Florida.In this episode, I sit down with Ben to talk about what it takes to build differentiated assets in a world where generic real estate is becoming increasingly commoditized. We discuss hospitality, branding, direct bookings, content marketing, raising capital, and why some properties continue to outperform even when the broader market slows down.We also dive into entrepreneurship, resilience, family, time management, and the realities of building multiple businesses while raising young children.

Courtney didn't start in real estate.She owned a Pilates studio, invested in long-term rentals, and eventually made the leap into short-term rentals and hospitality design. Today, her two Myrtle Beach properties generate over $500,000 in annual revenue, and her company, Denori Designs, helps short-term rental owners and boutique hotel operators create spaces that outperform their competition.In this episode, I sit down with Courtney to talk about what most investors miss when evaluating a property: the guest experience.We discuss creating competitive moats through design, designing around a specific guest avatar, turning ordinary properties into memorable experiences, and why hospitality is about far more than aesthetics. We also dive into entrepreneurship, intentional living, overcoming setbacks, and building a business aligned with the life you actually want.This conversation is about creating spaces people remember, designing a life with purpose, and building assets that generate both revenue and meaning.

Shaun Rahimi spent nearly a decade building a pain management company from scratch… eventually selling it for eight figures to Hinge Health.In this episode, I sit down with Sean to break down what it actually takes to build over 8+ years, raising capital, rebuilding after setbacks, and the level of belief required when nothing is working yet.But we also talk about what happens after you “make it.”We get into burnout, identity shifts, grief, and why success doesn’t automatically solve the things you think it will. This conversation is about building something real, questioning what you’re optimizing for, and creating a life that actually feels aligned, not just successful on paper.