Eugene Gershman
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.
Author
Eugene Gershman
Category
Podcast website
Latest episode
Jul 3, 2026
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Episodes
How Blue-Collar Investors Build Wealth 21.05.2025 27:10
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 farmland solo to raising capital for value-add multifamily syndications tailored to a working-class in...
What They Don’t Teach You About Land Use 16.05.2025 32:58
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 scenes of Marre , his latest project—a 67-home, design-coordinated community in Rockport, Texas. With tho...
The Hidden Power of Thoughtful Design 12.05.2025 39:22
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 them. She shares actionable strategies for developers to infuse warmth and uniqueness into homes withou...
Why Most Investors Miss Out on Industrial Deals 07.05.2025 34:42
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 co-sponsorship accelerates development, and why due diligence in this space demands more than spreadsheet...
How a $20M Portfolio Nearly Broke Me 04.04.2025 40:16
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 through his evolution from taking a $200K line of credit to building (and pivoting) a real estate empire...
Why Self Storage Beats Apartments 03.04.2025 22:13
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 real estate. From analyzing market demand to dealing with REIT competition, Sean breaks down exactly how a...
How to Pay Less in Taxes Without Breaking the Rules 28.03.2025 19:50
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 down complex tax strategies like bonus depreciation, passive vs. active income treatment, and even how...
Mastering Real Estate Marketing with Digital Strategies 20.03.2025 33:30
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 marketing early and effectively. From “5-a-day” ad campaigns to leveraging AI-driven engagement strategies, A...
Raising Capital and Surviving Market Crashes 05.03.2025 38:30
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 dive deep into how he bounced back, strategies for raising capital, and why taking a hit in business c...
The Truth About HOAs Every Developer Must Know 19.02.2025 30:47
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 communication to reducing frustrating fines, Brandon shares how technology, AI, and good old-fashioned...
Scaling Development, Risk Management, Builder Selection, and Coaching 03.02.2025 33:23
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, navigating historic remodels, and dealing with the risks that come with both construction and development. Wh...
The Secrets to Securing Loans and Managing Risk 23.01.2025 23:12
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 equity and debt, and effectively presenting loan packages to lenders. From creative uses of debt funds t...
Zoning, Financing, and Real Estate Growth 12.12.2024 32:14
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, evaluate investment risks, and structure deals that attract and retain investors. With $50 million in as...
Feasibility Studies and Team Building for Developers 07.12.2024 27:40
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, creating strong contracts, and avoiding common pitfalls that derail projects. Whether you’re an aspiring...
The Real Talk on Multifamily Development 06.12.2024 10:17
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 often impractical allure of luxury finishes and rooftop decks, Eugene's insights brought laughter and val...
The Art of Raising Capital 30.11.2024 27:30
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 employed, such as educating potential investors and leveraging relationships. Conner also discusses the bene...
Developing Profitable Short-Term Rentals 23.11.2024 35:56
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 navigation, and strategic market positioning. He shares how his portfolio leverages lifestyle-driven amenit...
Developing Built-to-Rent Projects 16.11.2024 30:26
Real estate developer Andy McMullen discusses the growing trend of “build-to-rent” communities, explaining their appeal, economic advantages, and the challenges of development. He highlights strategic market selection, streamlined entitlement processes, and the increasing demand for single-family rentals. Andy also shares personal anecdotes from his career, offering valuable lessons on navigating...
The Future of Real Estate Lending with AI 14.11.2024 23:37
Let’s talk about the intersection of AI and mortgage lending with Michael Vandi, the 24-year-old CEO of Addy AI. Michael shares insights into how his company is revolutionizing the mortgage process for real estate lenders by using AI to automate document review, compliance checks, and borrower follow-ups, speeding up what traditionally takes weeks down to mere days. He explains how Addy AI’s techn...
Real Estate Investing and Fundraising Synergies 13.11.2024 40:20
Eric Burns, founder of Flowers Capital, dives into his journey from a finance major and firefighter to a real estate entrepreneur and capital raiser. Eric shares how his background in finance and real estate helped shape his approach to investing, managing projects, and raising capital. He discusses the transition from residential to commercial real estate, emphasizing the importance of community,...
Creative Financing and Market Trends in Real Estate 06.11.2024 32:37
In this episode, we dive into the dynamic world of real estate financing with Kevin Amolsch, a real estate investor and private money lender. Kevin brings a wealth of knowledge on creative financing strategies, navigating complex deals, and adapting to shifting market conditions. He shares invaluable insights on private lending, explains the impact of cap rates, and offers a realistic perspective...
Preventing Legal Pitfalls and Conflict Resolution 31.10.2024 41:29
Attorney Corinne Rockoff dives into the nuances of legal planning, contract negotiation, and dispute resolution in real estate development. Corinne shares actionable strategies for avoiding litigation through early-stage legal planning, fostering strong relationships with contractors and consultants, and crafting clear, enforceable contracts. With a focus on real-life scenarios, she illustrates ho...
Building Smarter: Tax-Saving Secrets and the Future of Modular Construction 26.10.2024 32:55
This episode features James Bohan, a CPA, real estate investor, and developer with extensive experience in navigating the complex intersections of real estate investment, tax strategy, and modular development. Known for his insights into real estate’s unique tax advantages and innovative construction techniques, James brings a tone of knowledge to help investors make savvy, tax-efficient decisions...
Passive Income Strategies: Real Estate, Oil, and Gas Explained 23.10.2024 29:23
In this episode, we go beyond just real estate development. What does it take to diversify your portfolio and unlock passive income streams through real estate and beyond? Let's dive deep with Keshav Kolur, a software engineer by trade and an investor in real estate, private equity, and oil and gas. Whether you’re a tech professional looking to diversify your wealth or an investor seeking new oppo...
Risk, Reward, and Returns with Max Gonzales 11.10.2024 38:35
In this power-packed episode, real estate expert Max Gonzales joins host Eugene Gershman to explore the vast and dynamic world of real estate development and investment. This episode is more than just a discussion on real estate—Max takes us through critical insights on managing risk and the decision-making process in real estate projects. Max explains the often misunderstood risk profiles in mult...
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