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

A few years ago, Vince was working as a nurse.

Today, he’s built and sold a company that generated over $15M in lifetime sales… all while working full time.

In this episode, I sit down with Vince to talk about money, habits, and what it really takes to build freedom while still working a full-time job.

We get into why most people avoid talking about money, how that slows their growth, and what high performers actually struggle with when it comes to focus and follow-through.

This podcast is about creating optionality and becoming the person capable of the next level.

Daisy Chung spent 10 years in sales, most recently as Head of Revenue at a SaaS company, Orum.

At 33, she stepped away from the 9-5 job she loved after building enough cash flow from six real estate properties to cover her lifestyle.

In this episode, I sit down with Daisy to talk about what retirement actually means, how she built financial freedom through real estate in just 4 short years, and why the goal was never to stop working, but to gain control over her time.

We talk about how high earners can feel stuck despite making great money, how she accumulated 6 properties, moving from California to Las Vegas, and building cash flow without a master plan.

We also dive into identity, confidence, taking imperfect action, and how starting with even $100 a month in side income can change the way you see your future.

This conversation is about breaking out of the “well-paid but trapped” cycle, creating options for yourself, your family, and creating a life where money no longer dictates your decisions.

Ashley Du is the founder and CEO of Meaningful Beginnings, a growing network of childcare centers in the Bay Area.

In this episode, I sit down with Ashley to talk about growing up in scarcity, getting divorced at 24, building a million-dollar business, losing 40% of revenue in two months, and rebuilding after roughly $275,000+ in credit card debt.

We also dive into ego, identity shifts, leadership, meditation, healing childhood patterns, and what it really takes to grow into the next version of yourself.

This conversation goes far beyond business.

It’s about resilience, self-awareness, and becoming the leader your next chapter demands.

Calvin Chin lost $100,000 on his first real estate deal at 24. Today he oversees 1,400 units across seven states and runs multiple seven-figure businesses working just 25 hours a week.

In this episode, I sit down with Calvin and talk about the mindset, identity shifts, and discipline required to move from corporate success to true financial freedom.

We discuss real estate investing, abundance vs scarcity thinking, finding the right mentors, and why many high performers struggle with focus and follow-through even after achieving success.

This conversation isn’t just about real estate. It’s about building freedom, designing your life intentionally, and becoming the person capable of the next level.