Real Estate Development: Land to Legacy

Eugene Gershman
  • 0.0 (0)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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.

  1. Land Development Tips

    MAR 12

    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 land can be taken from a simple parcel to a 50-, 100-, or 200-home community, why builders often prefer buying finished lots instead of taking on development risk themselves, and what landowners should understand before selling too early and leaving serious money on the table. Guest Bio Brandon Cobb is a real estate entrepreneur focused on land development, paper development, affordable housing, and selling individual lots to builders. Eugene introduces him as someone who has completed more than 180 transactions. In the episode, Brandon shares how he moved from a successful career in medical device sales into entrepreneurship, then into flipping houses, building homes, and eventually developing land after national homebuilders began approaching him to buy projects he was working on. Episode Highlights and Chapters 01:29 Eugene sets up the conversation around how value is actually created in land development, with a focus on paper development, affordable housing, and the real leverage behind entitlement work. 02:50 Brandon shares how losing his medical device sales job became the turning point that pushed him toward entrepreneurship and real estate. 05:44 After getting inspired by a Shark Tank pitch, Brandon experiments with several failed business ideas before discovering real estate, flipping his first house, and learning through costly mistakes. 21:33 Brandon explains the layered value creation in land deals, from entitlement to infrastructure to vertical construction, and why multiple exit strategies make the model so attractive. 24:16 The conversation turns to why national builders often prefer entitled or finished lots over raw land, especially when speed, timing, and return on capital matter more than taking development risk themselves. 26:31 Brandon breaks down what builders typically want in a project, why around 50 lots can be a meaningful threshold in his market, and how smaller communities can still work when they fit a builder’s pipeline. 28:25 One of Brandon’s biggest lessons for landowners is to understand what their land could be worth after entitlement, instead of selling as-is and potentially leaving major upside behind. 29:42 Eugene adds the owner’s perspective, explaining the tradeoff between certainty and upside, since developers often take on the work and risk but also delay the seller’s payoff until approvals are complete. 32:08 Brandon shares the two main ways people can work with him: education and coaching for people who want to learn land development, and passive investment opportunities for those who want exposure to the strategy without operating deals themselves. Contact Information Brandon Cobbhttps://learnlanddevelopment.com Investment opportunities:https://hbgcapital.net/waitlist Interested in being a guest on our podcast? Contact us at:https://giscompanies.co/podcast/ Download the Feasibility Study Checklist to assess your project’s potentialhttps://giscompanies.co/development/feasibility-study/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    34 min
  2. The Airbnb Moment for Commercial Space

    FEB 26

    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 commercial space hiding in plain sight? The conversation explores a “Craigslist-style” approach to commercial listings, designed to make fractional and unconventional spaces feel approachable, searchable, and actually monetizable.  Guest Bio Steve Taylor is the founder of SoCommercial, a platform built to help owners list and monetize commercial spaces of any type or size, especially the odd, fractional, or overlooked ones that don’t fit neatly on traditional listing sites.  Episode Highlights and Chapters 00:03 The origin story of a pandemic-timed lease and an 1,800-square-foot empty office 05:50 Why traditional commercial listing sites felt clunky and overpriced, and what a better experience looks like 06:28 The Airbnb comparison and the bigger question about “unmonetized” commercial space 07:43 Real-world use cases from warehouse racks to spare chairs, basements, display space, and collaboration concepts 09:57 The brutal reality of building a marketplace and why traction matters more than perfect tech 14:31 If everything is free to list, how does the business eventually make money 16:04 How developers can use flexible leasing and “artisan mix” thinking to enhance retail and office projects 18:21 The problem with small ground-floor retail in residential buildings and why brokers often ignore it 21:13 Why the platform stays focused on listings instead of consulting, and when to use AI for ideas 22:37 Not a broker, not a competitor, just another option for visibility and exposure 25:12 Launch timing, bootstrapping, and why this kind of startup is a long marathon 28:23 The ask to listeners, plus the tease of a jingle you have to hear on the site  Contact Information SoCommercial website: https://socommercial.com Contact Eugene Gershman for real estate development advice and guidance. Download the free feasibility study checklist at https://giscompanies.co/development/feasibility-study/ If you’d like to be a guest on the show, visit https://giscompanies.co/podcast/. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    31 min
  3. 1031 Exchange and DST Investing Basics

    FEB 19

    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, and why many long-time owners eventually trade hands-on management for passive ownership through Delaware Statutory Trusts (DSTs). Eugene and Ashley also explore the gray areas developers run into, why investor intent matters, how DST restrictions shape risk and return, and what due diligence looks like when picking sponsors and properties.  Guest Bio Ashley Romiti is the founder of GCA 1031 and works with real estate investors who want to transition from active ownership into passive real estate investments using tax-deferred 1031 exchange strategies. She frequently uses DSTs as a fractional-ownership structure that can help investors pursue capital preservation and income while deferring capital gains and depreciation recapture. Ashley is a registered representative affiliated with a broker-dealer relationship through which these offerings are made.  Episode Highlights and Chapters 00:00 Ashley’s niche: helping investors move from active ownership to passive investments using 1031 exchanges and DSTs  02:54 A plain-English definition of the 1031 exchange and why taxes can be so painful on a sale  06:01 The core timeline: 45 days to identify replacement property and 180 days to close  06:27 What happens at death and how step-up in basis affects long-term strategy  07:09 Development and 1031 exchanges: where the gray areas appear and why CPA guidance matters  10:50 What a DST is, how fractional ownership works, and why “Delaware” is about the trust structure  12:49 Why DST properties often concentrate in landlord- and tax-friendly states  14:32 DSTs versus syndications, including how ownership and economics differ  19:11 SEC framework and disclosures, including how offerings are presented and documented  21:05 Sponsor incentives, exit decisions, hold periods, and DST rules that shape operational flexibility  24:03 Where DSTs can fit for developers, including “takeout” concepts and solving for leftover exchange boot  26:17 How Ashley screens deals: sponsor track record, fundamentals, structure, and investor goals  30:20 Common DST asset classes today and why office remains challenging  32:07 Typical minimums, accredited investor requirements, and diversification across multiple DSTs  35:51 How to reach Ashley and where to download her 1031/DST ebook  Contact Information Ashley Romiti / GCA 1031  https://gca1031.com Free ebook available. 949-235-5606    Host Eugene Gershman / GIS Companies https://giscompanies.co/ If you’re a developer or investor evaluating a deal, download Eugene’s free Feasibility Study Checklist to pressure-test assumptions, costs, timelines, and returns before you commit capital. If you’re interested in being a guest on the show, visit the podcast page to connect and apply. https://giscompanies.co/podcast/   Ashley Romiti offers securities through Concorde Investment Services, LLC (CIS), member FINRA/SIPC. GCA 1031 is independent of CIS. Concorde is headquartered at 3909 Research Park Drive, Suite 200, Ann Arbor, MI 48108. This podcast is for informational purposes only, does not constitute as investment advice, and is not legal or tax advice. Please consult the appropriate professional regarding your individual circumstance. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    37 min
  4. Digital Nomads are Coming: How to Develop Overseas

    FEB 12

    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 markets, and what it really takes to develop across borders without getting “skinned alive.” Along the way, he breaks down the mindset that keeps projects (and reputations) intact: treat mistakes as tuition, lead with humility, and build local trust the hard way—without bribes.    Guest Bio Michael K. Cobb has been building communities and working on real estate development across Latin America for over 25 years, with experience in places like Belize, Nicaragua, and Panama.  He also consults with investors and developers on overseas due diligence and execution, and he’s the author of “How to Buy Your Home Overseas.”   Earlier in his international career, he helped start a mortgage company in Belize that later became a bank, giving foreign buyers access to financing in-market and adding liquidity for developers after sales close.  Episode Highlights and Chapters 00:00 Humility as the “biggest asset” when you leave your home turf  01:16 The real question: how to avoid getting destroyed building overseas  01:47 Horror stories, getting ripped off, and reframing mistakes as “tuition”  03:47 How to enter a new country: test every assumption, and use multiple lawyers (including a hyper-local one)  06:44 “We’ve never paid a bribe” and the CSR strategy that builds local advocates  08:59 Timelines and entitlements: a Panama “horror story,” and what “a long time” can mean  10:27 Project size and phasing: the Panama plan (110 acres, smaller phase one) and an anchor continuing-care concept  13:53 The demand shift: digital nomad visas, renters (not buyers), and why this wave is “exploding”  16:44 Build-and-sell vs. hold-and-rent, and how “easy button” services change long-term demand  19:10 Financing overseas: why it’s mostly private equity/private lending, plus buyer financing as liquidity  21:14 Pre-sales: how projects get stranded half-built, and when pre-sales can make sense  40:32 Belize as an “easy button,” and a 1,600-acre project looking for development partners  44:52 Mike’s book offer: email to get a free Amazon coupon  45:53 Where to find Mike and ECI Development online  Contact Information Michael K. Cobb / ECI Development podcast@ecidevelopment.com (email to request the free Amazon coupon for “How to Buy Your Home Overseas”)  www.ecidevelopment.com Host: Eugene Gershman https://www.linkedin.com/in/eugenegershman/ To learn more about GIS and our real estate development services, explore our website and see what we’re building. www.giscompanies.co Interested in being a guest on the show? Visit our podcast page for details and how to connect: https://giscompanies.co/podcast/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    46 min
  5. Preserving Affordable Housing with 75% Returns

    FEB 12

    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% below market while still structuring “sustainable bonds” that (at the top tier) advertise a 75% total return profile over 36 months. The conversation gets into how these private, unlisted debt securities work, who they’re for (accredited investors), why the strategy focuses on preservation instead of new construction, and how factory-built homes can be deployed quickly to bring more units online without the waste of traditional site-built development.  Guest Bio Dr. Canaan Van Williams is the managing founder of Proactive Sustainable Bonds and describes his organization as a Reg D 506C fund issuing sustainable bonds through the Proactive Realty Income Fund II to LLC. He works in the affordable housing and social impact housing space, focusing on low-income and workforce residents across multiple states, and notes third-party impact verification efforts including Morningstar Sustainalytics, UNPRI, BlueMark, and an Impact Evaluation Lab assessment.  Episode Highlights and Chapters 00:00 – The episode’s focus: affordable housing, manufactured homes, and raising capital.  01:55 – Dr. Van introduces Proactive Sustainable Bonds and the Reg D 506C structure.  02:28 – What the “sustainable bonds” are: private, unrated debt securities for accredited investors tied to affordable housing outcomes.  04:12 – How the bonds are secured: real estate hard assets and property insurance (not a public rating or guarantee).  05:22 – How capital is used, bridge debt takeout, and Dr. Van’s personal investment in the fund.  06:39 – Hybrid approach: mostly funding their own strategy, with some allocation possible to aligned projects/managers under the PPM.  07:26 – UN Sustainable Development Goals discussed and how the strategy aligns with specific SDGs.  08:24 – Why a bond structure instead of a typical private debt fund: proving a profitable-and-impactful model.  08:43 – Liquidity and duration: private, unlisted, illiquid; commonly 2–3 year terms with longer options.  09:23 – Target assets: manufactured housing communities, multifamily, SRO motels; prioritizing “impact rate of return.”  11:36 – Defining NOAH (naturally occurring affordable housing) and why it matters.  13:38 – Why new construction rarely replaces NOAH and why preservation is a key strategy.  14:46 – For-profit vs nonprofit: how a for-profit social impact mandate intentionally preserves affordability.  16:46 – The nonprofit support layer: housing essentials, transportation support, and behavioral workbooks for second-chance populations.  18:59 – Manufactured homes in the model: sourcing factory-direct homes, rapid deployment, and passing savings to residents.  20:05 – “We don’t build anything”: focusing on distressed properties and infrastructure upgrades in existing parks.  21:02 – Investor programs and tiers: accredited-only, minimums, current income approach, and the headline 75% return tier details as described.  24:10 – Closing thoughts: execution, claimed investor repayments to date, where to learn more, and Dr. Van’s book.  Contact Information Proactive Sustainable Bonds website: www.sustainablebonds.com   Email: invest@sustainablebonds.com Phone: 1-800-626-2089  Direct: 803-989-8264  LinkedIn: https://www.linkedin.com/in/dr-canaan-williams-aa3924b/ Host: Eugene Gershman – https://giscompanies.co/podcast/ Interested in real estate investing frameworks, underwriting insights, and episodes like this one? Head to https://giscompanies.co/podcast/ to get resources and connect with GIS. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    25 min
  6. The Safe Play: Debt and Mobile Homes

    JAN 14

    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 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 just on returns, but on character. Ian opens up about the psychology of trust-building with investors, why he values stability over flashy returns, and what makes mobile home parks an overlooked but compelling asset class. Whether you’re looking to raise capital, allocate capital, or simply understand what separates a good deal from a great partner, this episode is packed with timeless lessons. Guest Bio Ian Noble is a Texas-based investor and founder of RunSteady. After selling his family’s dry cleaning business in 2023, Ian transitioned into real estate full-time, focusing on mobile home parks and private lending. His investing philosophy centers around capital preservation, character-driven partnerships, and accessible passive income strategies. Episode Highlights and Chapters 01:00 – Why capital preservation trumps high returns in Ian’s investment philosophy 02:00 – From dry cleaning to real estate: Ian’s journey into passive investing 04:20 – The challenge of trusting others with your capital 05:45 – How Ian vets character in potential partners 07:45 – Switching roles: From investor to capital raiser 09:00 – Why trust takes time and urgency kills relationships 10:10 – Referrals and long-term relationships as the core of Ian’s investor network 12:30 – Real estate is a full-time job: The appeal of passive investing 13:30 – Marketing and capital raising: Why last-minute outreach doesn’t work 15:30 – Ian’s two key focus areas: private lending funds and mobile home parks 17:30 – How Ian’s debt fund works and what makes it low risk 21:30 – Managing defaults and borrower relationships in a volatile market 23:50 – Why Ian emphasizes risk over upside in private lending 27:30 – Investor psychology: logic brings them in, emotion seals the deal 30:00 – Tips for analyzing underwriting assumptions and red flags 31:30 – What mobile home parks are (and what they’re not) 33:20 – Manufactured homes, zoning, and why foundations matter for taxes 36:00 – Touring a factory: the surprising quality of manufactured homes 38:00 – Why Ian chose mobile home parks over apartments 40:30 – Value creation by infilling lots in mobile home parks 42:00 – Why cities resist approving new parks and how that creates opportunity 43:30 – ADUs, zoning laws, and development trends in Seattle 45:00 – Gentrification, real estate change, and why Ian says “Play the game” Contact Information You can learn more about Ian Noble and his investment firm at https://runsteadycapital.com Free Passive Investing in Real Estate Cheat Sheet: https://go.runsteadyinvestments.com/land-to-legacy-podcast Join Ian's Passive Investor Mailing List: runsteadyinvestments.com/investor-club LinkedIn: www.linkedin.com/in/iannoble1/ Instagram: @ian_invests   For more episodes, visit Eugene Gershman’s podcast page at https://giscompanies.co/podcast/ Download our free feasibility study checklist: https://giscompanies.co/development/feasibility-study/  Find out if your project is ready to be financed here: https://giscompanies.co/development/feasibility-study/   Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    47 min
  7. No Money? No Problem in Real Estate

    JAN 6

    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 multimillion-dollar real estate deals using creative financing. He explains how growing up in Detroit with no examples of financial independence shaped his early limiting beliefs — and how shifting his mindset was the key to changing his life. Whether you’re an investor, a developer, or just someone starting from zero, this conversation offers a compelling breakdown of how deals can be built without traditional financing. Guest Bio David Webb, known as the “No Money Millionaire,” is a real estate investor and educator who built a multimillion-dollar portfolio using creative financing strategies — all without investing his own capital. Raised by a single mother in Detroit and evicted more than 15 times before making it, David’s success came through a mix of grit, relentless sales experience, and out-of-the-box deal-making. Today, he mentors others through his platform No Money Millionaire and recently published a book by the same name, aiming to help aspiring investors overcome limiting beliefs and get into real estate regardless of their financial standing. Episode Highlights and Chapters 00:35 – David’s backstory: from Detroit struggles to his first break in sales 03:40 – Surviving 15+ evictions and powering his home with a car inverter 06:46 – The mindset shift that made real estate investing possible 10:38 – The underrated power of reading and taking action 13:46 – David’s first seller-financed home and early creative deal structures 17:46 – How David funded a 9-home deal using bank and private money 22:43 – Top three no money strategies for real estate investing 26:20 – Understanding ARV (After Repair Value) and securing 100% financing 27:14 – Overcoming fear of rejection: sending “those 3 texts” 28:26 – Why sellers agree to finance deals themselves 29:36 – Where to find seller-financed deals (Craigslist, Zillow, Crexi, more) 31:05 – David’s son’s path from Detroit to USC and real estate in California 33:22 – Real-world parallels between creative investing and development 34:50 – David’s first passive deal and learning from the sidelines 36:05 – How to connect with David and get his free book Contact Information David Webb Free book download and resources: https://nomoneymillionaire.com Search “No Money Millionaire” to find him on Facebook and all major social media platforms.   Eugene Gershman If you’re interested in being a guest on the Land to Legacy podcast, submit your application at: https://giscompanies.co/podcast/ Explore more free tools and resources at the GIS Companies website. Download the Feasibility Study Checklist to assess your project’s potential: https://giscompanies.co/development/feasibility-study/ If you’re preparing to finance a development, visit https://giscompanies.co/development/financing/ and take the Financing Readiness Score Card to see where you stand. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    37 min
  8. Mobile Home Money And Mayhem

    2025-12-08

    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 storage. Eugene talks with investor and podcast host Gabriel Petersen about how he transitioned from a corporate role at Microsoft into niche commercial real estate, why he loves sticky pad-rent income over single-family rentals, and how he structures creative seller-financed deals (including a 20-year interest-only note). They walk through underwriting mobile home and RV parks, differentiating business models, dealing with crime risk in self storage, navigating municipalities that don’t want new mobile home parks, and deciding when it’s finally time to sell and roll capital into the next opportunity.  Guest Bio Gabriel Petersen is a real estate investor focused on mobile home parks, RV parks, and self storage facilities. After starting his career in the corporate world at Microsoft, he flipped houses and wholesaled single-family properties before realizing it would take too long to reach his goals with small rentals. That pushed him into commercial assets, beginning with a mobile home/RV park acquisition in Washington State that he bought with seller financing and then expanded from there. Gabriel now owns multiple parks and storage facilities across markets including Washington and Arkansas, and he is the host of The Real Estate Investing Club podcast, where he interviews active investors across a wide range of strategies and asset classes. Chapters 00:00 Introduction to Mobile Home Investments 01:47 Gabe's Journey into Real Estate 03:32 First Deal: Underwriting and Financing Insights 08:06 Understanding Mobile Home and RV Parks 10:09 Business Models: Tenant-Owned vs. Park-Owned Homes 10:48 Lessons Learned from Early Acquisitions 13:18 Property Crime and Self Storage Facilities 18:54 Cold Calling vs. Brokerage: Finding Deals 19:11 The Benefits of Off-Market Deals 20:07 Negotiating Directly with Sellers 22:22 Understanding Cap Rates in Real Estate 23:19 Challenges in Developing Mobile Home Parks 25:01 The State of Self Storage Development 26:35 Utilizing Seller Financing 29:14 Finding New Properties in the Market 30:48 Deciding When to Sell Properties 33:26 The Role of Podcasting in Real Estate Networking   Contact Information To connect with today’s guest, Gabriel Petersen, visit The Real Estate Investing Club at therealestateinvestingclub.com or email him at gabe@therealestateinvestingclub.com.  To learn more about host Eugene Gershman, his projects, and the Real Estate Development: Land To Legacy podcast, visit https://giscompanies.co/podcast/. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    36 min
See All (61)

Trailer

About

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.

Information

You Might Also Like