When Real Estate Gets Real

How do you scale a real estate portfolio while maintaining a full-time career, raising a family, and preparing to take on bigger multifamily deals?
In Episode 12 of When Real Estate Gets Real, I sat down with Hugo Macau, Managing Partner of Forest Estate LLC Commercial Real Estate, to talk about Hugo’s journey from the IT world into hands-on real estate ownership and commercial multifamily investing.
Hugo currently owns nine units across three properties and is preparing to close on a 25-unit portfolio spread across four properties in Providence, Rhode Island. He shares how skills from his IT career including analysis, project management, contract negotiation, and organization have helped him evaluate opportunities and build his real estate business.
But scaling from a handful of units into larger multifamily deals changes the game.
Hugo discusses learning to delegate, building a team of property management, legal, and accounting professionals, working with like-minded investors, and maintaining the standards that matter to him as his portfolio grows.
What You’ll Learn
• How Hugo transitioned from IT into real estate investing• Why the first property can be the hardest one to buy• How corporate skills can transfer into commercial real estate• What Hugo looks for when analyzing real estate opportunities• Why scaling requires learning to trust and delegate• How investor relationships fit into Hugo’s growth strategy• Why tenant experience matters beyond the numbers• Hugo’s goal of reaching 100–200 units in the next year• How generational wealth influences his long-term vision• His advice for people afraid to make their first real estate move
Chapters
[00:00] — Meet Hugo Macau[01:00] — The 25-Unit Providence Portfolio[02:35] — From Portugal to Canada to the United States[04:20] — Overcoming Fear on the First Real Estate Deal[05:30] — Why Real Estate Became Hugo’s Passion[07:00] — Using IT and Negotiation Skills in Real Estate[09:00] — Balancing Career, Family, and Property Ownership[11:25] — Building Relationships With Real Estate Investors[13:25] — Becoming a Steward of Investor Capital[14:30] — Building a Team to Scale Multifamily[16:30] — Hugo’s Goals for 100–200 Units[18:25] — Generational Wealth and Hugo’s “Why”[20:00] — Advice for New Real Estate Investors[22:15] — How to Connect With Hugo Macau
For Hugo, real estate isn't simply about reaching a certain number of units. It's about building something meaningful, creating homes people value, and establishing a legacy for the next generation.
Want a chance to share your side of the story?
Apply to be a guest: https://whenrealestategetsreal.com/podcast-booking

Most homeowners are sitting on untapped equity without realizing it.
In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with mortgage advisor and investor-focused lender Benjamin Stef to discuss how investors are using Home Equity Lines of Credit (HELOCs) to fund deals, scale portfolios, and create opportunities without refinancing low-rate mortgages.
Ben breaks down how HELOCs work, why they've become significantly easier to access, and how investors are leveraging home equity to fund everything from rental properties to private lending opportunities.
The conversation also shifts into entrepreneurship, focus, and the identity changes required to build a successful business without constantly chasing the next shiny object.
What You'll Learn
What a HELOC is and how it works
Why investors are increasingly using HELOCs
How to evaluate financing opportunities based on ROI
The difference between active and passive investing
Why focus is one of the most important entrepreneurial skills
How successful investors avoid analysis paralysis
Decision-making frameworks for growing businesses
Key Highlights
Faster HELOC approvals and funding timelines
Real-world HELOC investing strategies
Using home equity without refinancing
Focus vs. distraction in entrepreneurship
Scaling a business while investing wisely
Connect with Benjamin Stef
Website: https://www.fundingfreedom.net/
Youtube: https://www.youtube.com/@UCYZIjA6JcV0DqLD-1q2iZbQ
 
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Real estate investing looks simple online but what happens when you actually start raising capital, managing investor expectations, and underwriting multifamily deals?
In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with Ray Woods, a real estate investor, engineer, cybersecurity professional, and entrepreneur building across wholesaling, Airbnb, multifamily, and real estate technology.
Ray shares how his first wholesale deal changed the way he looked at money, why reinvesting into the business mattered, and what investors often misunderstand about scaling into multifamily syndication.
This conversation also gets into the responsibility of managing investor capital, why communication matters when deals go wrong, and how Ray is building a syndication app to help investors underwrite deals more clearly.
What You’ll Learn:
How Ray moved from engineering into real estate investing
What he learned from his first wholesale checks
Why managing money is different from earning money
What changes when you start raising investor capital
Why communication protects credibility in tough deals
How better underwriting can help syndicators avoid bad deals
Why patience matters in multifamily investing
Connect with Ray:
Website: https://tinyurl.com/rewithray
Instagram: https://www.instagram.com/realestatewithrayy/
YouTube: https://www.youtube.com/@RealEstateWithRay?sub_confirmation=1
TikTok: https://www.tiktok.com/@realestatewithray
 
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What happens when you make millions early… then lose almost everything?
In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with Lawrence Dunning former MMA fighter turned real estate broker, investor, and developer who shares his raw, unfiltered journey through success, failure, and rebuilding.
From trading floors in Chicago to losing money in the 2009 crash… to navigating bad partnerships and lawsuits… Lawrence breaks down the real lessons most people never talk about.
This episode goes beyond tactics it’s about resilience, identity, and finding your place in real estate.
What You’ll Learn:
Why early success can actually set you up for failure
How to find your niche in real estate (and why it takes time)
The biggest mistakes new investors make
How to evaluate partnerships the right way
Why hardship makes you better in business and life
Key Highlights:
Transitioning from trading to real estate
Losing money and rebuilding from scratch
Lessons from a failed development partnership
The importance of intuition in business decisions
How real estate development transforms communities
Guest: Lawrence Dunning Broker | Investor | Developer | Former MMA Fighter
 
Ways to connect with Lawrence Dunning
LinkedIn: https://www.linkedin.com/in/lawrence-dunning-mba-2b97a120
Instagram: https://www.instagram.com/lawrencedunning
Webiste: https://enterthelionheart.com
 
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Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at info@raisegenius.ai.

Commercial real estate has changed dramatically over the last few years but is today’s market really like 2008?
In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with Jacob Clopton, founder and president of Clopton Capital, to unpack what’s happening in commercial real estate financing, debt markets, insurance, solar, capital raising, and multifamily syndication.
Jacob shares why today’s challenges are less about a lack of liquidity and more about leverage, interest rates, and cost of capital. He also explains what early-stage syndicators should understand about raising capital, building a team, and avoiding the trap of trying to do everything alone.
What You’ll Learn:
How today’s market compares to 2008
Why many multifamily deals are struggling despite strong occupancy
What commercial real estate debt looks like right now
How Clopton Capital supports investors across financing, insurance, sourcing, solar, and 1031 services
Why first-time syndicators should focus on direct investor relationships
The importance of delegation when scaling a real estate business
Connect with Jacob:
Website: https://cloptoncapital.com/
LinkedIn: https://www.linkedin.com/in/jakeclopton1
Youtube: www.youtube.com/@cloptoncapital3417
 
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Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at info@raisegenius.ai.

Most real estate investors start the same way solo, figuring it out, and trying to scale on their own.
But what happens when that model stops working?
In this episode, Stephen sits down with Jared Mickley, a Marine Corps helicopter pilot and multifamily asset manager, to break down his journey from house hacking and short-term rentals to stepping into multifamily investing.
This conversation goes beyond tactics it dives into the real shift that happens when you stop treating real estate like a side hustle and start running it like a business.
What You’ll Learn:
Why single-family investing hits a scaling ceiling
The real reason multifamily is a team sport
The 4 key roles in a multifamily deal
What makes capital raising actually work
The difference between investor interest and commitment
Why consistency beats speed in real estate
Key Highlights:
Transitioning from VA loan house hack to STR and midterm rentals
Lessons learned managing rentals remotely during deployment
How military teamwork translates into real estate success
Inside a real multifamily team structure
The mindset shift that changes everything
 
Connect with Jared:
Website: https://www.glidepathinvestments.com/team/jared-mickley
LinkedIn: linkedin.com/in/jared-mickley-b4008114a
Email: jared@glidepathinvestments.com
 
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Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
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What happens when corporate “security” disappears overnight?
In this episode, Stephen Lee Thomas sits down with Mike Deaton, co-founder of Flipping Dirt, to break down his journey from being laid off at Microsoft to building a land flipping business with over 700 deals completed.
Mike shares how he and his wife pivoted into entrepreneurship, why land investing became their focus, and the lessons they learned the hard way through partnerships.
 
What You’ll Learn:
How land flipping works as a business model
Why your first deal is about confidence—not income
The hidden risks of real estate partnerships
How to think about failure as an entrepreneur
Why deal flow matters more than perfection
Key Highlights:
From dual layoffs to full-time entrepreneurship
First land deal: $3K → $10K flip
Why land offers more control than multifamily
Lessons from deals that went underwater during COVID
Building a business that fits your lifestyle
Connect with Mike: Website: https://flippingdirt.us/freedom
Facebook: https://www.facebook.com/mikeandligia
LinkedIn: https://www.linkedin.com/company/flipping-dirt
 
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Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at info@raisegenius.ai.

What happens when you realize you like real estate — but not the part everyone assumes you should be doing?
In this episode of When Real Estate Gets Real, Stephen Lee Thomas talks with Will Harvey of Harvey Capital about his path from mortgage lending to flipping houses, passive investing, and eventually building a hard money lending business.
Will shares how he discovered that operations were not his strength — and that the finance side of real estate was where he truly belonged. The conversation digs into what changes when you begin managing investor capital, how to separate decision quality from outcomes, and why protecting capital matters more than chasing growth.
This is a valuable episode for operators who are still figuring out where they fit, as well as investors trying to better understand what makes a disciplined capital partner.
What You’ll Learn:
How Will Harvey transitioned from house flips to hard money lending
Why not every real estate investor should be an operator
What changes when you start managing other people’s money
How to think about good decisions vs bad outcomes
Why protecting capital matters before scaling
What most people misunderstand about raising capital
How to identify your real estate superpower
Key Highlights:
From mortgage business to real estate investing
Why Will exited landlording and leaned into finance
Lessons from a wedding venue deal that did not go to plan
Building discipline as a fiduciary
Scaling a lending business through a fund structure
Why raising capital takes long-term relationship building
The importance of staying in your lane and adding value
Connect with Will Harvey:Website: harvey-capital.comEmail: will@harvey-capital.com
 
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Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at info@raisegenius.ai.