When Real Estate Gets Real

Real Estate Syndication, Capital Raising, and the Truth About Multifamily Investing

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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From Millionaire to Starting Over: Real Estate Lessons That Actually Matter

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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What Multifamily Investors Need to Know About Debt and Capital Raising

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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From House Hack to Multifamily: Why Scaling Alone Doesn’t Work

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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Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at info@raisegenius.ai.

The Truth About Real Estate Partnerships, Failure, and Finding Your Lane

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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How to Find Your Real Estate Superpower with Will Harvey

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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What Really Happens After Your First Real Estate Deal

In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with John Todderud of Cardinal Oak Investments to unpack the reality behind multifamily investing once the deal is done.
From managing tenants and operations to navigating investor expectations and market headwinds, this conversation reveals what most new operators aren’t prepared for.
John shares lessons from completing 9 deals, including the shift in responsibility when handling investor capital, the challenges of raising trust (not just money), and how today’s market is creating new opportunities for those paying attention.
What You’ll Learn:
What changes after closing your first deal
The biggest operational surprises in multifamily
How investor responsibility shifts decision-making
Why trust is the hardest part of raising capital
How interest rates and lending impact deals
Why today’s market may offer strong buying opportunities
Key Highlights:
The difference between solo deals vs syndications
Real challenges with bridge loans and cash flow
Why investors shouldn’t make every decision
The role of education in capital raising
Leveraging your network when things get difficult
Connect with John:Email: john@cardinaloak.comWebiste: https://cardinaloak.com/
 
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What Keeps Commercial Real Estate Deals Alive in a Down Market?

What actually keeps a commercial real estate deal alive when the market turns against you?
In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with Will Curtis, a commercial real estate broker out of San Antonio who has been involved in more than $1 billion in transactions and is known as the “Property Operations Whisperer.”
This conversation goes beyond surface-level real estate advice and gets into the real drivers of long-term success: disciplined underwriting, smart leverage, operational awareness, and the kind of leadership that only comes from experience.
Will also shares how his military background shaped his perspective, what he learned from watching seasoned investors survive past crashes, and why he hopes to eventually create a real estate fund for veterans.What You'll Learn
Why debt and leverage management matter in every market cycle
What operators can and cannot fix through property operations
How the office market changed after COVID
Why San Antonio has performed differently than Austin
Leadership lessons from commercial real estate and the military
The importance of humility, team building, and learning from mistakes
Key Highlights:
Why managing leverage is the #1 factor in surviving real estate downturns
Lessons from investors who survived the 2008 financial crisis
The real impact of COVID on the office real estate market
Why San Antonio outperformed other major Texas markets like Austin
The importance of buying right—before operations even begin
How experienced operators stay competitive during market declines
Emerging trends like flexible office and third-space environments
The concept of the “labor leverage ratio” and what it reveals about office demand
Leadership lessons from both military and commercial real estate experience
Why humility and team-building are critical for long-term success
Ways to connect with Will CurtisWebsite: https://www.vetsinrealestate.com/LinkedIn: https://www.linkedin.com/in/willcurtisccim/Facebook: https://www.facebook.com/willcurtisccim/Instagram: https://www.instagram.com/willcurtisccim/Youtube: www.youtube.com/@vetsinre
 
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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.