The ROI Masterclass

What if a single design change to your Airbnb could generate $400,000 in additional projected revenue? That's exactly what happened for commercial real estate investor and fund manager Cherif Medawar — after one conversation about aesthetics changed how he saw his entire portfolio.

About This Episode:

In this episode of the ROI Masterclass, Liat Siegel sits down with Cherif Medawar, commercial real estate investor, fund manager, author, educator, and the largest owner of historic properties in Old San Juan, Puerto Rico, with over 30 years of experience building, acquiring, and transforming real estate across residential, retail, mixed-use, hospitality, and commercial asset classes.

Cherif shares the defining philosophy behind his career: the money isn't in the property, it's in the structure. From his early days working at the Century Plaza Hotel in Los Angeles to becoming the right-hand man to a billionaire at just 21 years old, to building a $100M real estate fund, Cherif breaks down the exact frameworks he uses to assess risk, structure deals, and scale businesses without losing himself in the process.

Key Topics Covered:

The 6-part risk mitigation framework Cherif uses on every investment (safety, cash flow vs. cash out, liquidity, reserves, plan B/C/D, and diversification)

How a $70,000 aesthetic investment in Puerto Rico Airbnb units is projected to generate $400,000 in additional annual revenue

The three stages of wealth: working for money, working the money, and letting the money work for you

How to buy vacant single-tenant commercial buildings and convert them into cash-flowing or cash-out plays

The strategy-structure-system-automation-scale-sustainability framework for building a business you can sell or pass on

Why your guest reviews are your best punch list — and how Cherif used complaints to 10x his 14-room hotel's revenue before selling it

The Airbnb algorithm insight most operators don't know: higher-pixel cameras result in immediate higher ranking

Connect with Cherif Medawar:

🌐 cmrei.com

📺 YouTube: Search "Cherif Medawar" (3,500+ videos)

--------

The operators we interview every week are in this room. Come join us. Link in bio.

#RealEstateInvesting #CommercialRealEstate #AirbnbStrategy #RealEstateFund #STRoperator #BoutiqueHotel #ROI #WealthBuilding #Entrepreneurship #RealEstatePodcast #CherifMedawar #ROIMasterclassWhat if a single design change to your Airbnb could generate $400,000 in additional projected revenue? That's exactly what happened for commercial real estate investor and fund manager Cherif Medawar — after one conversation about aesthetics changed how he saw his entire portfolio.

About This Episode:

In this episode of the ROI Masterclass, Liat Siegel sits down with Cherif Medawar, commercial real estate investor, fund manager, author, educator, and the largest owner of historic properties in Old San Juan, Puerto Rico, with over 30 years of experience building, acquiring, and transforming real estate across residential, retail, mixed-use, hospitality, and commercial asset classes.

Cherif shares the defining philosophy behind his career: the money isn't in the property, it's in the structure. From his early days working at the Century Plaza Hotel in Los Angeles to becoming the right-hand man to a billionaire at just 21 years old, to building a $100M real estate fund, Cherif breaks down the exact frameworks he uses to assess risk, structure deals, and scale businesses without losing himself in the process.

Key Topics Covered:

The 6-part risk mitigation framework Cherif uses on every investment (safety, cash flow vs. cash out, liquidity, reserves, plan B/C/D, and diversification)

How a $70,000 aesthetic investment in Puerto Rico Airbnb units is projected to generate $400,000 in additional annual revenue

The three stages of wealth: working for money, working the money, and letting the money work for you

How to buy vacant single-tenant commercial buildings and convert them into cash-flowing or cash-out plays

The strategy-structure-system-automation-scale-sustainability framework for building a business you can sell or pass on

Why your guest reviews are your best punch list — and how Cherif used complaints to 10x his 14-room hotel's revenue before selling it

The Airbnb algorithm insight most operators don't know: higher-pixel cameras result in immediate higher ranking

Connect with Cherif Medawar:

🌐 cmrei.com

📺 YouTube: Search "Cherif Medawar" (3,500+ videos)

--------

The operators we interview every week are in this room. Come join us. Link in bio.

#RealEstateInvesting #CommercialRealEstate #AirbnbStrategy #RealEstateFund #STRoperator #BoutiqueHotel #ROI #WealthBuilding #Entrepreneurship #RealEstatePodcast #CherifMedawar #ROIMasterclass

Why Skipping Your Hotel Renovation Is a Slow Death — And What to Do Instead | Tommy Beyer

With over 20 years in hospitality from valet at a four-diamond resort to VP of Operations overseeing 15–20 hotels and co-founding a private REIT. Tommy Beyer has seen exactly what separates hotels that thrive from those that quietly fall apart.

In this episode, Tommy breaks down the costly mistakes hotel owners make when they defer renovations, cut corners on PIPs, or piecemeal their CapEx spend. He explains why good general managers will eventually walk away from properties that aren't being maintained, why the brand on your building matters less than people think, and how to renovate smarter — not just bigger.

Tommy also gets into flag changes, franchise negotiations, new build vs. existing acquisitions, and what it really takes to drive rate above your comp set rather than just catching up to it.

What you'll learn:

Why deferred maintenance becomes a "death throttle" for hotel revenue

How to time a flag change strategically around your renovation cycle

Why piecemeal renovations cost more and deliver less

The one thing that drives owners to finally do the PIP

How to hire the right team before the first dollar is spent

What it takes to push rate above the competition not just match it

Connect with Tommy:

🌐 bhospitalityadvisors.com

🔗 LinkedIn: Tommy Beyer

#HotelInvesting #HospitalityROI #AssetManagement #HotelRenovation #BoutiqueHotel #RealEstateInvesting #STR #HotelOperations #CapExStrategy #ROIMasterclass

What if your space was so well-designed that it closed deals before you even opened your mouth?

Mauricio Ruiz, founder of Worked Up, a co-working space in New Jersey, built exactly that. After launching 20+ businesses across industries including signage, branding, and hospitality, Mauricio identified a massive gap in his local market: co-working spaces that were either boring white boxes or inaccessible city locations. So he built something intentional, elevated, and different — and filled it to near-capacity within six months.

In this episode of the ROI Masterclass, Liat Siegel sits down with Mauricio for the show's very first in-person recording to unpack:

How entrepreneurial instincts started at age 9 in Peru — selling fireworks, running backyard movie nights, and stocking beer and cigarettes for family parties

Why environment and aesthetics aren't just "nice to have" — they directly drive occupancy, retention, and word-of-mouth

How a TikTok video he never planned went viral locally and converted viewers into paying members

The construction lessons he learned the hard way as a first-time GC — and what he'd do differently

Why he believes design is one of the single most undervalued investments in any business

His 3-point framework for anyone building a co-working space or experience-driven business

The long-term vision: 3–5 locations, potential franchising, and eventually a private equity firm focused on helping entrepreneurs grow

Mauricio's story is one of grit, intentionality, and the relentless belief that spaces shape the people inside of them.

——————

Join the Deal Makers Community — start your free trial today at stan.store/hadar

#coworking #entrepreneurship #realestateinvesting #ROI #designmatters #workspacedesign #businessgrowth #smallbusiness #boutiquehospitality #communitybuilding #startupstory #worklifebalance

The Golden Age of Multifamily Is Over — Now What

A $5 million equity raise is actually harder to close than a $20 million one. Capital broker Sitta Dumbuya breaks down exactly why and what sponsors need to know to get their deals funded in today's market.

With a background in engineering and years of hands-on experience in multifamily acquisitions, operations, and now capital strategy, Sitta Dumbuya brings a rare, grounded perspective to the financing side of real estate. In this episode, Sitta unpacks why the post-2022 capital markets have fundamentally changed the game for sponsors, what institutional equity partners are actually looking for before they issue a term sheet, and why most sponsors are approaching capital the wrong way.

Key Takeaways:

→ Why interest rate increases created a persistent spread between buyers and sellers — and how it's reshaping deal flow

→ The shift from high-leverage bridge debt to lower-leverage, fundamentals-driven underwriting

→ Why institutional capital wants to "bet on the jockey, not the horse" — and what that means for your track record

→ How to tell the story that moves a deal from spreadsheet to signed term sheet

→ Why raising $5M in equity is harder than raising $20M — and how institutional check sizes drive that dynamic

→ The incentive misalignment problem with third-party property management — and what to do about it

→ Sitta's 3-part capital-raising framework: storytelling, information discipline, and tailored ask

🔗 Work with us: stan.store/hadar

#RealEstateInvesting #CapitalRaising #MultifamilyInvesting #RealEstatePodcast #HadarInteriors #CommercialRealEstate #STR #BoutiqueHotel #PassiveIncome #RealEstateDevelopment #PropertyManagement #ROI #Entrepreneurship

104 Rejections Later How a Stay at Home Mom Built Jersey City’s Most Unique Coworking Space

She heard "no" from 104 landlords before a single one said yes. Eight days after opening Narra Collective, she was in the operating room with a ruptured appendix and she still built the space to 100 members, 100% private suite occupancy, and an 18-person waitlist.

In this episode of the ROI Masterclass, Sheila breaks down how she stacked revenue streams across private suites, event space memberships, hot desks, and after-school programming and how she achieved a 70% tour-to-member conversion rate with a team of four. She also gets real about knowing your numbers, when to pivot, and why community is the product.

🔗 Work with us: stan.store/hadar

📍 Learn more about Narra: joinnara.com

📧 [email protected]

#DesignForROI #STRDesign #BoutiqueHotel #HospitalityDesign #RealEstateInvesting

How Iconic Hotels and Restaurants Are Designed for Both Magic and Profit!

What does it actually take to create a hospitality experience people never forget?

Jennie Yip has spent 30 years building the answer from opening The Delano Hotel with Ian Schrager and Philippe Starck, to designing F&B concepts across boutique hotels, private clubs, and restaurants around the world.

In this episode, Jennie breaks down the systems, strategies, and collaboration frameworks behind some of the most iconic food and beverage concepts ever built and why most owners get it completely wrong before they spend a single dollar.

What you'll learn:

Why the roundtable comes before the kitchen purchase every time

How lighting creates (or destroys) revenue in a hospitality space

The guest journey formula Jennie applies to every project she touches

Why cross-training staff is the most underutilized solution to the hospitality labor crisis

The three startup cost categories developers consistently overlook

How the Delano Hotel taught her that magic can be designed but only when every collaborator is fully committed from day one

Three tips Jennie leaves every owner with:

Get concept clarity through roundtable discussions before anything else

Understand your full startup costs before spending a dollar

Study your competition at every level programming, staffing, guest experience, and price point

Whether you're opening a boutique hotel, launching a restaurant concept, or trying to revitalize an underperforming F&B operation, this conversation is a masterclass in doing it right.

#HospitalityBusiness #FoodAndBeverage #BoutiqueHotel #HotelROI #RestaurantDesign #HospitalityDesign #FBStrategy #HadarInteriors #LiatSiegel #JennieYip #HospitalityPodcast #InteriorDesign #RestaurantStartup #HotelOperations #GuestExperience

Adam from PadSplit built a marketplace with over 30,000 co-living units, and discovered that low-income tenants have a lower eviction rate than Class A renters.

In this episode, Adam breaks down how PadSplit converts underutilized single-family homes into affordable, income-generating rooms and why the data on who actually makes a reliable tenant runs completely opposite to traditional underwriting bias.

He shares how hosts like Dave Edwards in Houston built tiered pricing systems, how private bathrooms drive 30% higher gross revenue, and the single biggest design mistake that costs investors renters long-term.

Adam also explains why yield matters more than ever in today's interest rate environment, and why this asset class is positioned to grow for years to come. Whether you're an STR operator considering a pivot, a boutique hotel owner curious about shared housing economics, or a real estate investor looking for your next yield strategy, this conversation is packed with data-backed insight.

PadSplit: padsplit.com | Contact: [email protected]

#RealEstateInvesting #CoLiving #PadSplit #AffordableHousing #ShortTermRentals #BoutiqueHotels #PropertyManagement #ROI #RealEstateInvestor #PassiveIncome #HousingCrisis #InvestmentStrategy

How Co Living Delivers 25% Cash on Cash Returns When Airbnb Returns Are Collapsing

DD Garzon has spent over 20 years in property management, building a 500-door company from the ground up, selling it, and then discovering the most profitable real estate model she's ever seen: co-living.

In this episode, DD breaks down exactly why co-living is outperforming every other asset class she's operated, including long-term rentals, Airbnb's, and commercial properties. She shares the real numbers behind PadSplit investments (15% average NOI, 25% cash-on-cash return, full capital recovery in four years), and explains why 45 million Americans who can't afford traditional housing are driving unprecedented demand for this model.

DD also reveals why so many co-living operators are failing, and it comes down to one thing most investors ignore: the resident experience. From mattress quality to room size to lighting, DD shows how intentional design directly impacts retention, occupancy, and returns.

Key insights from this episode:

Why Airbnb returns in Atlanta have dropped from 20%+ to 10% and where the smart money is going

The mindset shift from "landlord" to "service provider" that transformed DD's business

What makes or breaks a PadSplit property (hint: the 80 sq ft room always fails)

How to budget for design before you buy, and why skipping it is the most expensive mistake investors make

The systems and processes that allowed DD to scale to 500+ doors and eventually exit

How a real estate investment fund is expanding co-living inventory and access for new investors

Connect with DD Garzon: 📧 [email protected] 📱 Instagram & LinkedIn: DD Garzon

🔔 Subscribe for weekly conversations at the intersection of real estate, design, and ROI.

#CoLiving #PadSplit #RealEstateInvesting #PropertyManagement #PassiveIncome #STR #AirbnbAlternative #HousingAffordability #ROI #RealEstatePodcast #BoutiqueHotel #ShortTermRental #WealthBuilding #Entrepreneurship #RealEstateInvestor

Most NYC developers lose money before they even break ground, and they never know why. Joseph Segal, New York City real estate strategist and pre-development expert at Real New York, reveals the costly planning mistakes that leave buildings sitting vacant for years.

Summary:

Joseph started in real estate at 20 years old with no formal training, and built a career by going deeper than most on the details that determine whether a development succeeds or fails. In this episode, Joseph breaks down why the number of people on the first call predicts the success of an entire project, why a missing golf simulator cost one Upper East Side building multiple tenants, and why NYC's outer boroughs, especially eastern Queens, may be the most overlooked development opportunity in the country right now. He also shares his take on the Mamdani administration, rent stabilization, the FARE Act, and what the data actually says about turnover rates versus price per square foot.

Key Takeaways:

✅ Why washer/dryers, wing-two layouts, and lobby design directly impact your rent roll

✅ The two KPIs every NYC developer must track: price per square foot and turnover

✅ Why transportation access is the single most important factor in site selection

✅ How the renter has evolved — and why 2010-era thinking is killing modern developments

✅ What the Mamdani administration could mean for development incentives and housing supply

✅ Why bringing in consultants early — from trash chute experts to interior designers — accelerates ROI

#NYCRealEstate #RealEstateDevelopment #NewYorkCity #RealEstateInvesting #MultifamilyInvesting #RealEstatePodcast #PropertyDevelopment #ROI #HousingMarket #NYCDeveloper #RealEstateStrategy #ROIMasterclass

India's Hospitality Boom What Investors Can Learn From the World's Fastest Growing Market

Everyone is looking at the same markets.

The same cities.

The same trends.

The same opportunities.

Meanwhile, one of the world's fastest-growing hospitality markets is hiding in plain sight.

For more than 35 years, Samir Kuckreja has helped hotels, restaurants, investors, and private equity firms identify opportunities others miss.

His message was clear:

Don't invest based on trends.

Invest based on demand.

India's hospitality sector is experiencing a surge driven by domestic tourism, a growing middle class, rising consumer spending, and a shortage of quality hotel rooms across multiple segments.

But the biggest lesson wasn't about India.

It was about how investors think.

Most hospitality failures happen before construction even begins.

Poor feasibility studies.

Overestimated demand.

Wrong locations.

Following competitors instead of finding market gaps.

The investors who win are the ones who understand the numbers first and the concept second.

Because great hospitality isn't built on beautiful designs.

It's built on return on capital.

In this episode, we discuss:

• Why India is becoming a hospitality investment hotspot

• The biggest mistakes hotel and restaurant investors make

• Boutique luxury, wellness, and experiential hospitality trends

• How to evaluate ROI before deploying capital

• Why some hospitality concepts thrive while others fail

This conversation completely changed how I think about hospitality investment.

#Hospitality #Hotels #Restaurants #Investment #HospitalityInvestment #India #RealEstate #PrivateEquity #BusinessGrowth #Entrepreneurship #ROI