Real Estate Development: Land to Legacy
by Eugene Gershman
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
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The Rules That Backfire
A building can follow its written rules and still leave its owners carrying an unfair share of the cost. Condo and co-op consultant Mark Foley joins Eugene Gershman to examine what developers leave behind after the units are sold: governing documents, renovation controls, maintenance…
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Your Land Offer Gets Ignored
Your land offer may be getting sorted over a trash can before anyone reads it. Jessey Kwong, co-founder of Pebble, joins Eugene Gershman to examine what happens between identifying a property and getting its owner to talk. His central question is practical: does the outreach create an actual...
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When Cheap Houses Get Expensive
A $15,000 house can still become a $200,000 project. Jerry Larkowski bought two Little Rock houses marked for demolition, then faced missing building systems, delayed materials, borrowed-money pressure, and a second project that sold at a loss. The purchase price was only the beginning of the...
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Your Land Just Became a Fuel Stop
OVERVIEW Lisa Wright, founder of Landings, joins Eugene Gershman on Land to Legacy to make the case that your rural land may have just become a fuel stop. While most of advanced air mobility focuses on urban air taxis, Lisa is building North America's largest planned network of vertiports —…
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Why Architects Cost So Much
Overview What does a $47,000 architectural fee actually buy? Tim Derrington breaks down a proposal for a 17,000-square-foot gym in an existing strip center: $7,000 for design and code-compliance work, and $40,000 for coordination and documentation. The example explains why the initial concept can...
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Will This ADU Pencil?
A homeowner can be legally allowed to build an ADU and still be better off leaving the backyard alone. Babak Mortazavi joins Eugene Gershman to examine the economics, permitting, design, financing, and neighborhood tradeoffs behind accessory dwelling units. The conversation moves from the reason...
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Protect What You Build
The time to protect a project is before a claim arrives. Attorney and Certified Financial Planner™ practitioner Matthew Meredith joins Eugene Gershman to explain how real estate owners can reduce avoidable exposure before they buy, develop, lease, or refinance property. The conversation covers...
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Building Wealth at Your Pace
What do you do when a completed project no longer sells for the price you underwrote? Kevin “KAYR” Robinson and Eugene Gershman examine the decision that can determine whether a market downturn becomes a manageable delay or a permanent loss: accept the lower price, pivot to a rental hold, or keep...
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Land Use Traps
Overview A simple variance can turn into a costly appeal when the board, staff, or neighbors do not want the project. Kelley Morris Salvatore joins Eugene Gershman to explain where developers get into trouble with land-use approvals, why the right application strategy matters before anything is...
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One Deal Changes Everything
Overview One disciplined opportunity can change everything, but forcing ten years of progress into one deal is how developers get hurt. Forth Heffner joins Eugene Gershman to talk about the business lessons behind real estate execution: why failures are often the tuition, why collecting 100 no's...
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The Cash Flow Trap
Accounting may be boring, but Richard Boyd makes the case that boring is exactly where developers get protected. A growing real estate business can look profitable and still run into trouble if the owner does not understand cash flow, capital structure, debt service, work-in-progress accounting,...
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The Hidden Housing Edge
Mobile home parks are not really mobile, and the best operators are not just collecting rent from a row of trailers. Leo Young breaks down why manufactured housing communities can be a recession-resilient, infrastructure-heavy, relationship-driven asset class, and why the biggest fear is not…
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Land Development Tips
A failed motivational blog, a risky early move with retirement money, and a career setback all became part of the path that led Brandon Cobb into one of real estate’s most overlooked value-creation plays: land entitlement. In this conversation with Eugene Gershman, Brandon breaks down how raw…
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The Airbnb Moment for Commercial Space
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...
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1031 Exchange and DST Investing Basics
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…
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Digital Nomads are Coming: How to Develop Overseas
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...
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Preserving Affordable Housing with 75% Returns
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%…
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The Safe Play: Debt and Mobile Homes
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…
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No Money? No Problem in Real Estate
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...
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Mobile Home Money And Mayhem
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...
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Real Estate Cycles and Capital Raising
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...
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From House Hacking to Neighborhood Revitalization
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...
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90 Days to Stop Being the Bottleneck
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…
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How to Survive Your First Development
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…
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Nature Always Outbuild Developers
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…
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Secrets of a $3 Billion Portfolio
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...
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Seller Financing Secrets No One Teaches
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...
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AI Is Replacing Financial Advisors
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…
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Fixing Real Estate's Data Problem
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...
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The Future of Property Investing
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...
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The 200K Mistake That Made Him Stronger
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…
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The Discipline That Prints Wealth
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…
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How a $265K Deal Turned into $1.5M
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...
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How Blue-Collar Investors Build Wealth
Land to Legacy: Building Real Estate Success One Connection at a Time with Elijah Iung What happens when a former waste management entrepreneur transforms his network of blue-collar millionaires into a multifamily investment powerhouse? In this episode, Elijah Iung shares his journey from buying...
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What They Don’t Teach You About Land Use
From Land to Legacy: Navigating Coastal Development with Douglas Moreland How does a luxury community rise from concept to coastal landmark while preserving the environment and satisfying municipalities? Douglas Moreland, developer and founder of Moreland Capital Partners, takes us behind the...
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The Hidden Power of Thoughtful Design
Clean Lines, Smart Design: Why White Shaker Cabinets Still Work with Amy Barrickman White shaker cabinets might seem overdone—but not in Amy Barrickman’s world. In this insightful conversation, Amy, a seasoned interior designer, breaks down why design standards endure and how to innovate within...
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Why Most Investors Miss Out on Industrial Deals
What do Amazon warehouses, mom-and-pop tenants, and crab processing plants have in common? Gregg Gruehl reveals the unseen forces driving America’s industrial real estate boom. In this episode, Gregg shares why the world of industrial investments remains a mystery to many retail investors, how...
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How a $20M Portfolio Nearly Broke Me
When your net worth is in the millions but your bank account is nearly empty, what do you do? Wyatt Simon opens up about the raw moment in early 2024 when he found himself in tears, contemplating getting a job—despite owning 185 units and a $20 million portfolio. In this episode, Wyatt walks us...
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Why Self Storage Beats Apartments
When your rental property loses $30,000 and attracts squatters, it’s time to pivot—and Sean Graham did just that. In this episode, Sean returns for part two of his conversation with Eugene Gershman to dive deep into self storage, one of the most resilient and underappreciated asset classes in…
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How to Pay Less in Taxes Without Breaking the Rules
Did you know you could front-load your property depreciation to potentially wipe out your real estate income—legally? Sean Graham, CPA and founder of Maven Cost Segregation, unpacks how savvy investors leverage cost segregation to minimize taxes and maximize cash flow. In this episode, he breaks...
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Mastering Real Estate Marketing with Digital Strategies
Developers and investors often focus so much on building that they forget one crucial step—marketing. By the time they’re ready to sell or lease, it’s almost too late. In this episode, marketing expert Alex Thoric breaks down the essential strategies real estate professionals need to start...
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Raising Capital and Surviving Market Crashes
Mathew Owens learned the hard way that real estate isn’t always a straight path to success. From losing everything in the 2008 crash to building a thriving real estate investment business with over $150 million raised, Mathew shares the critical lessons that shaped his career. In this episode, we...
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The Truth About HOAs Every Developer Must Know
HOAs – love them or hate them, they’re here to stay. But what if your HOA actually worked for you instead of against you? In this episode, we talk with Brandon Barnum, CEO of HOA.com, about how his company is transforming homeowner associations across the country. From increasing transparency and...
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Scaling Development, Risk Management, Builder Selection, and Coaching
Flipping houses is one thing, but shifting to real estate development is a whole different game. Frank Iglesias shares his journey from being an investor and flipper to becoming a builder and developer—sometimes by accident. He dives into the lessons learned from building 20 homes at once,...
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The Secrets to Securing Loans and Managing Risk
Navigating today’s real estate financing landscape is tougher than ever, with rising interest rates and tighter lending environments. Jake Clopton, founder of Clopton Capital, explains how to overcome these challenges by leveraging strategic capital sources, understanding the trade-offs between...
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Zoning, Financing, and Real Estate Growth
Wayne Courreges III, Managing Principal at CREI Partners, shares a wealth of knowledge on mastering risk and maximizing returns in commercial real estate development. From leveraging seller financing to building relationships with municipalities, Wayne reveals how to navigate zoning challenges,...
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Feasibility Studies and Team Building for Developers
Real estate development offers incredible opportunities but demands careful planning and preparation to avoid costly mistakes. Sonny Moyers explains why building the right team and conducting a thorough feasibility study are essential for success. He shares insights on navigating hidden costs,...
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The Real Talk on Multifamily Development
Eugene Gershman of GIS Companies took the stage at the Bisnow Multifamily Conference in Seattle to deliver a sharp and humorous take on innovation in multifamily real estate development. From his candid thoughts on sustainable building practices and technological amenities to a critique of the...
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The Art of Raising Capital
Jay Conner shares insights on raising private money for real estate projects, emphasizing the importance of not relying on banks and instead creating a network of private lenders. He details his journey from begging banks for money to raising millions privately, explaining the strategies he...
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Developing Profitable Short-Term Rentals
The discussion explores the evolving dynamics of profitable short-term rentals, where hospitality meets real estate investment. George Salas provides insights into creating experiential properties that cater to families, business travelers, and vacation groups, emphasizing design, regulation...
About this show
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.
Hosted by
Eugene Gershman
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