
Advertise on podcast: Real Estate Development: Land to Legacy
Rating
5from
This podcast has
70 episodes
Language
EnglishPublisher
Eugene GershmanExplicit
No
Date created
2024/06/23
Latest episode
2026/10/12
Average duration
39 min.
Release period
20 days
Description
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.
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Check latest episodes from Real Estate Development: Land to Legacy podcast
Your Land Just Became a Fuel Stop
2026/10/12
OVERVIEWLisa 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 — landing and charging sites for electric aircraft — in the rural markets where the density of use cases, not population, drives demand. The conversation covers why regulators and manufacturers are converging on a 'rules-first' safety culture, how a rural-vertiport network could connect Upstate New York to LaGuardia-style hubs, and the energy strategy choices between solar colocation and waiting for grid connection at fast-charging sites. If you own rural land, the podcast makes a single practical case: this is a window to position your property as revenue-generating infrastructure for the electric aircraft era, before aviation reaches critical mass.
GUEST BIOLisa Wright is redefining the future of aviation infrastructure by focusing on the 80% of America that urban air mobility developers are overlooking. As founder of Landings, she is building North America's largest network of vertiports: landing and charging sites for electric aircraft, strategically positioned across rural markets where the density of use cases, not population, drives demand. With a background in architecture and energy management, Lisa brings a land-first perspective to advanced air mobility. While competitors race to launch urban air taxis, Landings is securing a planned network of 2,000+ rural sites across North America, from agricultural hubs to medical facilities to last-mile logistics centers, positioning vertiports as revenue-generating amenities for the electric future. Its first sites are advancing in New York's Mohawk Valley. As a manufacturer-agnostic developer, Landings builds infrastructure that any manufacturer's aircraft can use, giving it a neutral position as the major eVTOL makers race toward certification. Featured on Bloomberg Businessweek Daily and actively raising capital, Lisa is pioneering Rural Air Mobility as a distinct category, arguing that rural markets offer earlier adoption pathways through emergency response, agricultural services, and last-mile logistics, where infrastructure needs to be ready before aviation reaches critical mass.
EPISODE HIGHLIGHTS AND CHAPTERS
0:00 — Highlights reel1:23 — Intro reel1:34 — Lisa Wright interview — main conversation36:11 — Outro reel
CONTACT INFORMATION
Guest website: landings.co
Host and show links:- Eugene Gershman: https://egershman.com/- Land to Legacy hub: https://egershman.com/podcast/- GIS Companies: https://giscompanies.co/- Guest application: https://egershman.com/podcast/guest/
Get the free GIS Feasibility Study Checklist: https://giscompanies.co/development/feasibility-study/Considering development? Before you spend on design, use GIS's free Feasibility Study Checklist to organize the basic property facts, identify questions that still need answers, and prepare for a more useful conversation with your development team.
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Why Architects Cost So Much
2026/09/17
OverviewWhat 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 account for a small part of the work required to deliver a buildable project.
Tim joins Eugene Gershman to examine what owners should expect from an architect, how to evaluate a design team's construction knowledge, and why a convincing rendering leaves important questions unanswered. They discuss the responsibilities behind a complete set of plans, the limits of early cost estimates, and the money owners must spend to reduce uncertainty before construction.
The conversation moves through real project problems, including an engineering handoff that delayed construction and unexpected conditions beneath an existing building. Tim and Eugene examine how architects, civil engineers, structural engineers, and builders need to coordinate, and why the professional who leads the team should depend on the project.
They also discuss defining the development program before design, balancing function with the experience of a space, and the benefits and frustrations of building information modeling. Tim explains where he currently finds AI useful and closes with questions owners can ask to compare architectural proposals, understand exclusions, and choose a team they can trust.
Guest BioTim Derrington is the founding principal of Derrington Building Studio, an Austin-based architecture practice he founded in 2011. He trained at the University of Houston and is licensed to practice architecture in Texas.
The studio designs commercial interiors, adaptive reuse projects, and places for gathering, fitness, and recreation across Texas. In the conversation, Tim describes the firm's work in Austin, Houston, and San Antonio, including climbing destinations, retail spaces, and wedding venues. His perspective connects design intent with the coordination and construction details needed to carry it through.
Episode Highlights and Chapters00:00 — Episode preview
A preview of the conversation on architectural fees, hidden building conditions, verifying design details, and spending money to understand a project's feasibility.
00:58 — Land to Legacy intro
The Land to Legacy introduction.
01:09 — Meet Tim Derrington
Eugene introduces Tim and the questions developers bring to the relationship between architectural design, construction, and cost.
01:35 — What makes a good architect
Tim explains the combination of vision, coordination, and construction knowledge an owner should expect from an architectural team.
05:21 — Why early construction estimates remain uncertain
A concept can support a rough budget, but the materials, assemblies, and documentation needed for firmer pricing take time and money to develop.
08:38 — Check an architect’s work with builders and clients
Tim recommends speaking with previous clients and builders to learn how an architect's drawings and working relationships perform during construction.
09:55 — Knowing how the design will be built
Tim describes how his team researches assemblies, checks details with specialists, and tests whether a design can be built before treating it as resolved.
14:01 — Construction mistakes and hidden site conditions
Project stories show how coordination failures and unexpected existing conditions can interrupt construction. Tim also discusses taking responsibility for mistakes and bringing design disciplines together early.
25:23 — Which professional should lead the team
The appropriate lead depends on the building and its purpose. Eugene and Tim compare the priorities of architects, civil engineers, and structural engineers.
28:22 — Define feasibility and the program before design
Eugene explains how land-use research, a preliminary budget, market demand, and a potential exit inform the program given to the architect.
30:06 — Designing for function and experience
The discussion moves beyond attractive renderings to how spaces work for people, what problem a design solves, and how function and experience influence each other.
36:46 — Architectural software and documentation
Tim describes the studio's progression from early sketches to Archicad and three-dimensional modeling, including the time required to manage and revise detailed building information.
41:06 — Where AI helps in Tim’s practice
Tim discusses early concepts, text and contract review, and checking his own code research. Eugene shares an example of using AI for preliminary site-planning options.
45:19 — What an architect’s fee actually covers
A proposed $47,000 fee for a 17,000-square-foot gym illustrates the difference between initial design work and the larger coordination and documentation effort.
49:11 — Compare scope before comparing fees
Tim recommends asking what each proposal includes, who handles permitting and consultant coordination, and how revisions and design development will be managed.
51:54 — Tim’s practice and closing thanks
Tim describes Derrington Building Studio's commercial work across Texas and shares where listeners can learn more and contact the studio.
52:39 — Land to Legacy outro
The Land to Legacy closing.
Contact InformationConnect with Tim DerringtonDerrington Building Studio: https://www.derrington.co/
Contact Tim through the studio: https://www.derrington.co/contact/
About Tim and the studio: https://www.derrington.co/about/
Derrington Building Studio on Instagram: https://www.instagram.com/derrington.building.studio/
Episode lessonsLessons from Why Architects Cost So Much brings together six practical lessons from the conversation, each with an episode example and what it means for your project.
Get the episode lessons
Considering development?Before you spend on design, use GIS's free Feasibility Study Checklist to organize the basic property facts, identify questions that still need answers, and prepare for a more useful conversation with your development team.
Get the free GIS Feasibility Study Checklist
Eugene Gershman and Land to LegacyEugene Gershman: https://egershman.com/
Land to Legacy episodes: https://egershman.com/podcast/
Eugene Gershman on LinkedIn: https://www.linkedin.com/in/eugenegershman/
GIS Companies: https://giscompanies.co/
Apply to be a guest on Land to Legacy: https://egershman.com/podcast/guest/
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Will This ADU Pencil?
2026/09/15
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 ADUs have become a major housing strategy to the questions that decide whether a project works: purpose, feasibility, soft costs, hard costs, financing, parking, contractor pricing, prefab delivery, and the homeowner's tolerance for risk.
Guest BioBabak Mortazavi is the founder and CEO of LADU, a Los Angeles-based ADU design-build company.
LADU's official company profile says Babak has more than 15 years of experience in commercial and residential real estate development and founded the company to make ADU projects easier for Los Angeles property owners to plan and execute.
Episode Highlights and Chapters00:00 Highlights on pricing transparency, homeowner risk, permitting, and budget discipline.
00:57 Land to Legacy introduction.
01:08 Eugene introduces Babak and the role of accessory dwelling units in the housing discussion.
01:51 Babak explains why property owners have become an important part of California's housing strategy.
08:27 The conversation breaks down LADU's design, permitting, engineering, and construction platform.
11:43 Babak explains why the first question is whether the ADU is for family, income, or another specific goal.
16:38 Babak discusses construction pricing and why contractors should price the project instead of the customer.
19:38 Trust, reputation, and the high cost of failure in a homeowner's first major project.
21:28 A Coastal Commission delay becomes a lesson in reading the fine print and managing expectations.
25:24 Standardized lot patterns, repeatable designs, and the move toward a smaller menu of proven options.
26:55 Babak explains the promise and limits of prefab, including delivery, inspection, financing, and panelized construction.
33:04 Feasibility, stamped plans, contractor estimates, and why an ADU budget can expand like a wedding budget.
36:51 Eugene and Babak discuss neighborhood resistance, architectural fit, density, and the second-order effects of housing change.
45:35 Pocket neighborhoods, tenants in common, and alternative paths to homeownership.
47:43 How to contact Babak and request an LADU consultation.
Contact InformationBabak Mortazavi
LADU: https://www.ladu.co/
Free LADU consultation: https://www.ladu.co/free-consultation
Instagram: https://www.instagram.com/dreamladu/
LinkedIn: https://www.linkedin.com/in/babak-mortazavi-56966a254/
Host: Eugene Gershman / GIS Companies
GIS Companies: https://giscompanies.co/
Eugene Gershman: https://www.linkedin.com/in/eugenegershman/
Download the Feasibility Study Checklist to assess your project's potential: https://giscompanies.co/development/feasibility-study/
Interested in being a guest on the podcast: https://giscompanies.co/podcast/
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Protect What You Build
2026/08/29
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 revocable and irrevocable trusts, succession planning, trust-owned businesses, holding companies, LLC structures, corporate governance, personal guarantees, due-on-sale clauses, anonymous ownership, and the importance of separating operations from assets. Matthew also explains how these structures can grow with a portfolio and where lenders, taxes, and ongoing administration change the calculation.
Guest Bio
Matthew Meredith, Esq., CFP®, is the founder of Meridian Legal Advisors, a law firm focused on estate planning, tax strategy, and asset protection. He brings more than 20 years of financial-services experience to work that coordinates legal, tax, business, and financial planning for families, entrepreneurs, professionals, and real estate investors.
Episode Highlights and Chapters
00:00 Highlights
01:22 Land to Legacy intro
01:33 Matthew Meredith joins Land to Legacy
02:14 From wealth management to tax law
04:18 What owners should address before a project begins
05:58 Why protection must precede a claim
06:45 Revocable and irrevocable trusts
11:06 Trust-owned businesses and holding companies
13:50 Separating operations from real estate assets
16:45 Hub-and-spoke ownership for multiple properties
20:03 Scaling the structure without separate tax returns for every LLC
25:26 The limits of asset protection when a loan has a personal guarantee
28:02 Anonymous ownership and litigation deterrence
30:31 Domestic and offshore asset-protection trusts
37:52 How trust structures affect real estate financing
40:41 Due-on-sale clauses and structuring before a transfer
42:35 Subject-to transactions and lender risk
44:42 DSCR loans, rental income, and real estate opportunity
46:09 How to connect with Matthew
Contact Information
Matthew Meredith / Meridian Legal Advisors
Website: https://meridianlg.com/
LinkedIn: https://www.linkedin.com/in/matthewrmeredith
Eugene Gershman / GIS Companies
GIS Companies: https://giscompanies.co/
Eugene Gershman on LinkedIn: https://www.linkedin.com/in/eugenegershman/
Download the free Feasibility Study Checklist: https://giscompanies.co/development/feasibility-study/
Apply to be a guest on Land to Legacy: https://giscompanies.co/podcast/
This conversation is for general information and does not constitute legal, tax, investment, lending, or insurance advice.
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Building Wealth at Your Pace
2026/08/26
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 enough cash available to wait.
KAYR traces his path from moving about 18 times before age 18 to building a portfolio of more than 160 rental units. He explains the three forms of capital behind his first purchases—intellectual, social, and financial—and why he grew from one rental in 2009 to 105 units by 2020 at his own pace.
The conversation covers personal-name and LLC ownership, cash-on-cash return, downside scenarios, market and neighborhood filters, occupancy, cash-out refinancing, investor expectations, and reserve funds. KAYR also breaks down the strong deals he lost over relatively small negotiation gaps and the long-term cost of letting a good opportunity slip away.
Guest Bio
Kevin “KAYR” Robinson is a USA TODAY best-selling author, entrepreneur, real estate investor, speaker, and consultant focused on leadership, discipline, decision-making, and long-term growth. Raised in West Philadelphia, he describes moving about 18 times before adulthood, later working at Goldman Sachs, and building a portfolio of more than 160 rental units. His memoir, Can’t Break Me, examines how discipline, structured execution, and long-term thinking can turn unstable beginnings into durable ownership.
Episode Highlights and Chapters
00:00 Highlights
01:09 Kevin “KAYR” Robinson joins Land to Legacy
01:49 From West Philadelphia to 160+ rental units
02:50 How real estate entered the picture
05:11 From knucklehead to valedictorian
08:03 The three forms of capital behind a first purchase
10:27 Growing from one rental to 105
11:26 Buying personally versus through an LLC
14:11 Conservative underwriting and cash-on-cash return
20:09 Market, neighborhood, and zip-code filters
21:41 Eugene’s development return benchmark
25:26 What if the project does not sell?
27:30 Reserves, patience, and downside protection
31:41 The $5,000 mistake that cost much more
34:43 Your past does not define your future
35:33 Can’t Break Me and where to find KAYR
Contact Information
Kevin “KAYR” Robinson
Website: https://www.kayrmotivates.com/
LinkedIn: https://www.linkedin.com/in/krobins2/
Instagram: https://www.instagram.com/kayrmotivates/
Book and free prologue: https://www.kayrmotivates.com/book/
Eugene Gershman / GIS Companies
GIS Companies: https://giscompanies.co/
Eugene Gershman on LinkedIn: https://www.linkedin.com/in/eugenegershman/
Download the free Feasibility Study Checklist: https://giscompanies.co/development/feasibility-study/
Apply to be a guest on Land to Legacy: https://giscompanies.co/podcast/
This conversation is for general information and does not constitute investment, legal, tax, lending, or insurance advice.
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Land Use Traps
2026/07/03
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 filed, and how municipal relationships can shape the outcome of a project.
The conversation covers neighbor opposition, zoning analysis, planning-board dynamics, peer reviews, AI-assisted code research, affordable-housing density tradeoffs, and the practical difference between saving money and creating avoidable risk.
Guest Bio
Kelley Morris Salvatore is a partner at DarrowEverett and works in land use, municipal law, administrative appeals, business litigation, and energy and infrastructure matters.
She is licensed to practice in Rhode Island and Massachusetts and has practiced for about 30 years, mostly in Rhode Island.
Kelley also serves as a municipal attorney and town solicitor, and she has worked as special counsel in land-use matters.
Her experience gives her perspective from multiple sides of the land-use process, including developers, municipal staff, boards, neighbors, and public officials.
Episode Highlights and Chapters
00:00 Eugene introduces the conversation around land use, laws, regulations, and the issues developers can face during the approval process.
00:38 Kelley introduces her legal background, municipal work, and experience on multiple sides of land-use matters.
02:37 Kelley explains when a developer may need land-use counsel and why early involvement can prevent a weak application from becoming an expensive problem.
04:49 The conversation turns to why calling a lawyer only after there is a problem can cost more than getting the application right at the beginning.
05:23 Kelley explains why the type of application matters, including special use permits, variances, waivers, and zoning analysis.
06:22 Eugene describes why a general call to the city is often less effective than researching the code and asking a specific, routed question.
08:46 Kelley shares examples of projects that became harder because of local opposition, board behavior, or a town's resistance to the applicant.
11:05 Eugene describes a Bellevue project where early neighbor outreach still turned into a costly appeal and prescriptive-easement claim.
14:12 Kelley explains why she still recommends early neighbor engagement on larger projects and why reasonable comments can sometimes be solved before they become appeals.
15:28 Kelley discusses peer reviews and why traffic and drainage studies can help developers answer common public objections.
18:18 Eugene and Kelley discuss how AI is changing code research, legal research, and document review while still requiring professional judgment.
22:32 The conversation covers the risk of relying on outdated or incomplete online codes, especially when local ordinances are not fully codified.
25:29 Kelley explains why housing work has increased in New England and why affordable-housing requirements can create financial pressure for developers.
29:51 Eugene explains why rising costs, high interest rates, and weaker resale values are forcing developers to make harder choices on consultant budgets.
30:22 Kelley explains why planner support can matter even when a developer is trying to save money.
31:48 Kelley closes with advice on administrative approvals and avoiding unnecessary public-meeting risk when a project can qualify for staff-level review.
Contact Information
Kelley Morris Salvatore
DarrowEverett
Email: [email protected]
Website: https://darroweverett.com/
Profile: https://darroweverett.com/lawyers/kelley-morris-salvatore/
Host: Eugene Gershman / GIS Companies
GIS Companies: https://giscompanies.co/
Download the Feasibility Study Checklist to assess your project's potential: https://giscompanies.co/development/feasibility-study/
Interested in being a guest on the podcast: 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.
One Deal Changes Everything
2026/05/10
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 can make outreach less fragile, how culture and operating systems shape a company, and why leaders need to understand their own highest and best use before piling more complexity onto the business.
Guest Bio
Forth Heffner is an Executive Leadership Team Guide and business coach behind Heffner Leadership Coach and The Faculty Resource. His public bio describes a path into coaching shaped by firsthand experience in a family business, where he and his brother stepped into leadership after their father's sudden passing, learned through consultants and coaches, and later recognized culture, vision, values, and communication as critical ingredients for sustainable growth. His site describes his earlier work helping grow the family business before selling his majority position, and his current work guiding leadership teams through operating systems, strategy, culture, and execution.
Episode Highlights and Chapters
00:00 Opening highlights: failure as a lesson, one opportunity changing everything, highest and best use, and the danger of cramming ten years of progress into one deal.
01:19 Land to Legacy intro.
01:31 Forth explains how he came into commercial real estate from the vendor side and why that gave him a different view of developers, owners, and leadership teams.
02:42 Forth reframes failure as part of the learning process and compares business development to cold calling: collecting 100 no's can reset the pressure around every attempt.
04:20 Eugene explains why he often talks about what went wrong in development, because preventing expensive mistakes is more useful than pretending the business is easy.
07:10 Forth describes the importance of slowing down, clarifying who the business serves, defining shared vision and values, and staying disciplined about the chosen path.
11:31 Forth explains why one out of 100 opportunities may hit, but one disciplined and strategic deal can change the entire business.
13:31 The conversation shifts to coaching, why it can be hard to sell as a service, and why the real value is helping leaders pursue the endgame they actually want.
17:36 Eugene and Forth discuss highest and best use, not just for assets, but for people, leadership teams, and the roles founders should or should not keep carrying themselves.
18:55 Eugene explains why GIS shut down its construction company and how development plus construction can create too much operational and risk complexity for a growing business.
28:56 Forth and Eugene talk about building a legacy instead of only building an asset, including the pride that comes from pointing to real projects in a community.
30:19 Forth names one of the biggest mistakes developers make: trying to cram ten years of progress into one deal instead of committing to a path, mastering a niche, and building repeatable discipline.
32:32 Forth explains why even strong leaders need coaches, how outside accountability can push people past self-imposed limits, and what a prospective client should ask before choosing a coach.
34:00 Forth shares where listeners can find him and connect after the episode.
Contact Information
Forth Heffner
Website: https://heffneriv.com/
The Faculty Resource: https://www.thefacultyresource.com/
LinkedIn: https://www.linkedin.com/in/forthheffner
Host: Eugene Gershman
GIS Companies: https://giscompanies.co/
Download the free Feasibility Study Checklist to pressure-test a development opportunity before committing serious time and capital:https://giscompanies.co/development/feasibility-study/
Interested in being a guest on Real Estate Development: Land to Legacy? Visit:https://giscompanies.co/podcast/
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The Cash Flow Trap
2026/05/08
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, and worst-case planning before the market changes.
Guest Bio
Richard Boyd started an accounting practice in 2021 to help small businesses and real estate developers get clarity around their books, cash flow, payroll planning, debt, and financial forecasting. His work focuses on helping owners understand the health of the business, build better reporting, and put financial controls in place as the business scales.
Episode Highlights and Chapters
00:00 Eugene introduces Richard Boyd and frames accounting as the boring topic developers still need to understand.
00:54 Richard explains why owners avoid accounting, and why clean books reduce stress by making payroll, debt, and cash-flow questions clear.
02:49 Richard breaks down the difference between rear-view accounting and forward-looking financial forecasting.
03:41 Eugene and Richard discuss why starting entrepreneurs and developers often focus too much on profit and not enough on cash flow.
05:10 Richard explains why developers need accurate numbers to present a compelling story to lenders and support a viable development plan.
07:32 Richard describes what developers overlook as they scale from a small operation into a more complex business.
09:54 Richard shares the cautionary story of a $16M real estate investor who grew quickly, lacked visibility into cash flow and DSCR, and was forced to sell inventory at a discount after the market shifted.
13:02 Richard explains how deal assumptions can change, and why developers need contingency planning, exit strategies, and controls before the downside scenario arrives.
15:46 Richard describes how accounting support can scale from basic back-office bookkeeping into scenario modeling and financial planning.
18:39 Richard explains how early startup costs should be tracked when a landowner and partners are still testing whether a project is viable.
21:09 Richard discusses revenue recognition, project-cost capitalization, and why development costs belong on the balance sheet until the project is complete.
23:53 Richard explains why many owners misclassify development costs, then have to fix their books during tax season.
25:38 Eugene asks how AI is changing accounting, and Richard explains where AI helps with task-oriented work but still falls short on strategic CFO-level judgment.
30:07 Richard shares his core advice: it costs nothing to plan, and developers should pressure-test worst-case scenarios before they become real.
33:07 Richard shares how listeners can contact Atlantic Business Advisors.
Contact Information
Richard Boyd / Atlantic Business Advisors
Website: https://atlbusinessadvisors.com/
Email: [email protected]
Host: Eugene Gershman / GIS Companies
https://giscompanies.co/
GIS Companies has a free Feasibility Study Checklist available here:
https://giscompanies.co/development/feasibility-study/
To be a guest on the 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.
The Hidden Housing Edge
2026/04/23
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 sewer, roads, insurance, or resident issues. It is the problem no one budgeted for.
Guest Bio
Leo Young is the founder and managing partner of Cornell Communities, a company focused on acquiring, operating, and turning around manufactured housing communities across eight states. Cornell Communities focuses on providing affordable housing to hardworking Americans while targeting risk-adjusted returns for investors. Before building the company, Leo worked at Tesla during a high-pressure period in the company's history, an experience he says shaped his work ethic, mission-driven mindset, and approach to entrepreneurship.
Episode Highlights and Chapters
00:00 Eugene introduces Leo Young, founder and managing partner of Cornell Communities, and sets up the conversation around manufactured housing communities.
00:30 Leo explains Cornell Communities' two-part mission: provide affordable housing and generate strong risk-adjusted returns for investors.
01:04 Leo talks about moving from Tesla to trailer parks, including how Tesla's intense environment and near-bankruptcy period influenced the way he approaches entrepreneurship.
02:13 Leo explains how he found real estate, why passive cash flow caught his attention, and how a friend's investment thesis led him into mobile home parks.
04:49 The conversation turns to acquisition, underwriting, diligence, and what actually happens after closing when a new operator takes over a community.
07:31 Eugene and Leo compare land development feasibility work with manufactured housing due diligence, including utilities, public water connections, and business-plan assumptions.
08:07 Leo describes the biggest operational fear for investors and operators: an unaccounted-for event that blows up the budget.
08:57 Leo walks through resident management, road conditions, utility issues, collections, violations, and the day-to-day work behind operating manufactured housing communities.
10:29 Leo explains the diligence process, including municipal records, test ads, vendor checks, and a detailed checklist before closing.
12:01 Leo describes a cost-control approach to due diligence: start with the free or low-cost items, then move into more expensive third-party studies only when the deal still makes sense.
13:25 Leo explains how seller renegotiations happen when new information changes the economics of a deal.
14:07 The discussion covers the wide range of mobile home park pricing, from small properties to large institutional assets.
15:13 Leo explains why Cornell Communities prefers long-term holds, including the role of depreciation and tax consequences when selling.
16:10 Leo describes how deals are sourced, why brokered deals have become more competitive, and why proprietary outreach matters.
17:26 Eugene challenges the return profile, and Leo explains why the asset class can offer strong risk-adjusted returns compared with new development.
19:23 Leo talks about local contractor networks, small-market relationships, and why good vendors are often found through referrals rather than Google.
20:49 Leo explains the regions Cornell Communities likes, including the Southeast and Midwest, and how tornado risk interacts with a land-lease business model.
23:25 Leo describes typical deal financing, including fixed-rate loans, investor equity, reserves, capex budgets, and depreciation benefits.
24:19 Leo explains that Cornell Communities is primarily an operator, with in-house property management, asset management, and acquisitions.
24:58 Eugene and Leo discuss whether it is still feasible to build a new manufactured housing community from raw land, and why infrastructure costs and municipal resistance can make the numbers difficult.
27:05 Leo compares manufactured homes, park models, tiny homes, and container homes, and explains why manufactured homes are often the easiest for municipalities to understand and approve.
29:10 Leo gives his core lesson for landowners and operators: measure twice, cut once, get more bids than you think you need, and do the diligence before committing.
30:31 Leo shares how listeners can learn more about Cornell Communities, connect with him, and request his free mini-course on manufactured housing communities.
Contact Information
Leo Young / Cornell Communities
https://cornellcommunities.com
LinkedIn: https://www.linkedin.com/in/leo-young
Instagram: https://www.instagram.com/leoyoung.realestate
Free mini-course: message Leo the word MHC on LinkedIn or Instagram.
Host: Eugene Gershman / GIS Companies
https://giscompanies.co/
GIS Companies has a free Feasibility Study Checklist available here:
https://giscompanies.co/development/feasibility-study/
To be a guest on the 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.
Land Development Tips
2026/03/12
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/
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The Airbnb Moment for Commercial Space
2026/02/26
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.
1031 Exchange and DST Investing Basics
2026/02/19
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.
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Digital Nomads are Coming: How to Develop Overseas
2026/02/12
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
[email protected] (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.
Preserving Affordable Housing with 75% Returns
2026/02/12
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: [email protected]
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.
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The Safe Play: Debt and Mobile Homes
2026/01/14
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/
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Podcast reviews
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Sonny Moyers 2024/07/27
Super Host
This was an excellent interview and allowed me to share important ideas like, "Best use of Land..." concepts. Enjoyed the Podcast immensely. Great int...
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