Trailblazer Show

Ray left a successful career at Microsoft to pursue entrepreneurship and real estate full-time, starting with a $300K condo and eventually building a portfolio of short-term rentals.

In this episode, I sit down with Ray to talk about leaving Microsoft, building standout Airbnbs, and why he's now betting on capsule hotels and larger hospitality projects.

This conversation is about taking calculated risks, building for the long term, and creating a life where work doesn't come at the expense of what matters most.

Zach Metcalf spent 10 years building a successful career making over $400,000 in pharma while building real estate on the side 7 of those years. The 7 properties allowed him to say Congratulations to himself after being laid off.

Today, he owns multiple properties, and is developing micro resports and wedding venues in Joshua Tree and Upstate New York.

In this episode, I sit down with Zach to talk about leaving corporate life, replacing income through real estate, using hospitality investing to create tax advantages, and what it actually takes to build projects from the ground up.

We also dive into identity shifts, taking calculated risks, overcoming fear, surrounding yourself with ambitious people, and why building assets early creates options later.

This conversation is about creating freedom intentionally, betting on yourself, and building a life where your time belongs to you

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.

Soli Cayetano spent years flipping homes and scaling short-term rentals before finding her edge in boutique wellness hotels.

Today, she’s the developer behind Terra Palm Springs — a 13-key wellness hotel that outperformed revenue projections by 30-40% in its first year and landed features in Forbes, Vogue, Condé Nast, and Travel + Leisure.

In this episode, I sit down with Soli to break down what actually creates a premium hospitality brand, why branding and guest experience matter more than most operators realize, and how boutique hotels can compete with massive chains through positioning, wellness, and direct-to-consumer marketing.

We also dive into hotel investing, raising capital, designing experiences people remember, and why the future of hospitality is shifting toward wellness, intentional living, and experiential real estate.

This conversation is about thinking bigger, building differentiated assets, and creating brands people emotionally connect with.

Soli Cayetano spent years flipping homes and scaling short-term rentals before finding her edge in boutique wellness hotels.

Today, she’s the developer behind Terra Palm Springs — a 13-key wellness hotel that outperformed revenue projections by 30-40% in its first year and landed features in Forbes, Vogue, Condé Nast, and Travel + Leisure.

In this episode, I sit down with Soli to break down what actually creates a premium hospitality brand, why branding and guest experience matter more than most operators realize, and how boutique hotels can compete with massive chains through positioning, wellness, and direct-to-consumer marketing.

We also dive into hotel investing, raising capital, designing experiences people remember, and why the future of hospitality is shifting toward wellness, intentional living, and experiential real estate.

This conversation is about thinking bigger, building differentiated assets, and creating brands people emotionally connect with.

Blake Dailey has acquired over $20M in boutique hotels and short-term rentals across high-demand travel markets.

In this episode, we break down how he finds overlooked deals, why “saturated” markets aren’t what they seem, and how design, amenities, and positioning can completely shift returns.

We also dive into creative financing, building moats, and what it takes to operate at a higher level in real estate and business.

This conversation is about thinking bigger, executing with intention, and building assets that actually compound