Real Estate Development: Land to Legacy

Real Estate Development: Land to Legacy

Real Estate Development: Land to Legacy is hosted by Eugene Gershman, who scaled his company to $30M/year before the market forced a reset. Now rebuilding with deeper clarity, he shares real stories of growth, failure, and leadership. This podcast breaks down the real-life lessons and steps behind turning land into lasting value—educating listeners on what it truly takes to develop real estate. Guests include developers, investors, architects, land use consultants, and more. If you've lived the lessons and bounced back, we want to hear from you.

Episodes

February 25, 2026 30 mins

A five-year lease signed right before lockdown turns into an 1,800-square-foot “soccer field” of emptiness and a million-dollar headache. That pain sparks an idea with a big question behind it: if Airbnb unlocked the value of spare bedrooms, what’s the value of all the unused nooks and slices of commercial space hiding in plain sight? The conversation explores a “Craigslist-style” approach to commercial listings, designed to make f...

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A big real estate sale can create an even bigger tax bill, and that’s where Ashley Romiti steps in. She walks through how investors use a 1031 exchange to defer capital gains and depreciation recapture, what the “45 days to identify and 180 days to close” timeline really feels like in practice, and why many long-time owners eventually trade hands-on management for passive ownership through Delaware Statutory Trusts (DSTs). Eugene a...

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Digital nomads aren’t just a trend—they’re a demand shift that’s changing what “success” looks like for overseas real estate. Michael K. Cobb shares how his team thinks about building the right product for renters who stay three to six months at a time, why “clusters” create momentum for entire markets, and what it really takes to develop across borders without getting “skinned alive.” Along the way, he breaks down the mindset that...

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Preserving affordable housing doesn’t have to mean sacrificing investor returns. Dr. Canaan Van Williams breaks down how his firm targets naturally occurring affordable housing properties—older, often overlooked apartments, manufactured home communities, and SRO motels—and keeps rents 20–30% below market while still structuring “sustainable bonds” that (at the top tier) advertise a 75% total return profile over 36 months. The conve...

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January 13, 2026 47 mins

What does a dry cleaning business have in common with mobile home parks and private debt funds? According to Ian Noble, everything. In this candid conversation, Ian shares his journey from running a family dry cleaning business in Austin to becoming a thoughtful and selective real estate investor. He talks about selling his company in 2023, the mindset shift it took to move into passive investing, and how he now vets operators not ...

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January 6, 2026 36 mins

David Webb once powered his home by running extension cords from his car. Today, he owns over 100 doors in his real estate portfolio, all acquired without using his own money. In this gripping episode, David shares the raw truth of his journey from evictions and utility shutoffs to structuring multimillion-dollar real estate deals using creative financing. He explains how growing up in Detroit with no examples of financial independ...

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December 8, 2025 36 mins

A potato farmer who quietly bought an entire town, a septic system that failed almost the moment after closing, and a self-storage facility where thieves cut through every door just days before the sale—this episode goes deep into the real, unfiltered side of mobile home parks, RV parks, and self storage. Eugene talks with investor and podcast host Gabriel Petersen about how he transitioned from a corporate role at Microsoft into n...

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November 26, 2025 49 mins

Real Estate Cycles, Cross-Border Capital, and Why Raising Money Is Its Own Business — with August Biniaz

Why is now potentially the best time in years to enter real estate — and yet one of the most complex? August Biniaz, co-founder of CPI Capital, breaks down the current state of the real estate cycle, likening it to a clock that’s nearing “six o’clock” — the bottom of the market — and explains how this timing could spell opportuni...

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From House Hacking to Neighborhood Revitalization: Cameron Philgreen’s Journey to 35 Real Estate Units in Waco, Texas 

Cameron Philgreen did not begin his real estate career with a blueprint or a mentor—he started with a broken-down house in Waco, Texas, and a desire to offset his mortgage. By renting out his garage and basement, he turned his primary residence into a cash-flowing asset. That first step eventually led him to build a...

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September 12, 2025 36 mins

From Chaos to Control: Building a Self-Sustaining Contracting Business with Liz Chism 

Working 100-hour weeks, brewing beer, and managing international shipments while raising a toddler might sound like a recipe for burnout—but for Liz Chism, it was a wake-up call. In this powerful conversation, Liz shares how she transitioned from running a multi-million-dollar craft brewery to helping contractors escape the hamster wheel of long h...

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September 2, 2025 36 mins

A 27-Year Maui Project, Septic Setbacks, and Real Estate Wisdom from Both Sides of the Border

What do you do when a condo development takes nearly three decades to complete? If you're Dr. Jennifer Salisbury—real estate investor, educator, and ex-Navy Nuclear Propulsion Engineer—you grit your teeth, pivot with purpose, and document every lesson along the way. From her multi-year condo build in South Maui to launching a 48-pad tiny ho...

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August 29, 2025 31 mins

From planting his first seeds at age six to advising large-scale developments today, Belgian landscape architect Matthieu Mehuys has built a career around one mission — proving that working with nature is not only good for the planet, but also good for business. In this episode, Matthieu shares the journey from his family’s farm to studying in Munich, traveling the globe to learn from regenerative projects, and ultimately developin...

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August 8, 2025 40 mins


From $3B in Transactions to Building Smart: How Michael Kron Strategically Scaled a 13,000-Unit Real Estate Empire 


Decades before net lease funds became hot topics and Texas and Arizona dominated multifamily headlines, Michael Kron was already ahead of the curve—swapping out California C-class properties for A-class opportunities in emerging Sunbelt markets. In this wide-ranging conversation, Michael pulls back the curtain on how h...

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August 6, 2025 25 mins

Fuquan Bilal on Financial Friends, Flexibility over Freedom, and Building Trust in Real Estate 


Fuquan Bilal remembers the moment clearly: stuck at a toll booth without 35 cents, just months after earning a $40,000 check on his first real estate deal. That jarring contrast fueled a new chapter in financial discipline and long-term vision. In this episode, Fuquan shares how he turned early struggles and hard-won lessons into a portfo...

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August 1, 2025 35 mins

What do NASA, AI, and real estate investing have in common? According to Alexander Harmsen, quite a lot. In this episode, Alexander—a seasoned entrepreneur and the mind behind PortfolioPilot—shares how his background in aerospace and autonomous navigation systems led him to rethink financial advice entirely. After selling his previous company and navigating his own wealth management challenges, he saw firsthand the emotional pitfal...

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July 30, 2025 32 mins


From Town Planning to Tech Pioneer: How Jonny Britton is Digitizing Land Development 


What do a brick-sized cell phone, early Twitter, and a derelict lot in East London have in common? For Jonny Britton, they were part of the catalyst that pushed him from an uninspired town planning career into founding LandTech—a platform redefining how developers find, assess, and act on land opportunities. In this conversation, Jonny shares how a...

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July 24, 2025 30 mins

Legacy Meets Blockchain: Making Real Estate Truly Global with Ricardo Johnson 

What happens when you combine the timeless appeal of real estate with the revolutionary mechanics of crypto? Ricardo Johnson, Founder & CEO of Oasis, joins Eugene to break down how tokenization is making real estate investing accessible, liquid, and global. Drawing from his own journey—from launching a clothing brand and coffee business to building Oasis—...

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From Soccer Dreams to Real Estate Empires: Jacopo Iasiello’s Blueprint for Holistic Success 

A devastating injury at 17 ended Jacopo Iasiello’s dream of becoming a professional soccer player. But instead of succumbing to defeat, he pivoted—launching a jewelry business by 18 and eventually building a real estate empire that now spans the U.S., Italy, and Dubai. In this riveting conversation, Jacopo shares how a mindset shaped by medi...

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June 24, 2025 28 mins

From Ranger to Real Estate: How Justin Martinez Turned Discipline Into a Million-Dollar Mindset 

What drives someone to complete a 100-mile ultramarathon, flip multiple Airbnbs for six-figure profits, and still wake up each day ready to push harder? For Justin Martinez, it’s a mindset he calls "The Compounder’s Way"—where every disciplined choice compounds into a life of freedom and fulfillment. In this powerful episode, Justin shar...

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May 23, 2025 39 mins

Maximizing Value in Real Estate Development with Matin Haghkar 

How do you spot a winning deal that others overlook? For Matin Haghkar, it’s about knowing your numbers, trusting your team, and recognizing hidden potential—like the property he found sitting unsold for a year on the MLS, which he transformed into a lucrative mixed-use success. In this episode, Matin shares how he built a diversified real estate enterprise from scratch...

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