Real Estate Development: Land to Legacy

Your land offer may be getting sorted over a trash can before anyone reads it.

Jessey Kwong, co-founder of Pebble, joins Eugene Gershman to examine what happens between identifying a property and getting its owner to talk. His central question is practical: does the outreach create an actual acquisition, or merely a response? He shares observations from campaigns passing through Pebble and explains why the size of a postcard, the specificity of its message, and an image of the recipient’s own property can change the conversation.

Eugene brings the developer’s problem to the discussion: filtering a market by parcel size, zoning, length of ownership, and equity can produce a targeted list, but a list alone does not build trust. Jessey describes how to turn those property facts into a relevant message, explain what you can offer beyond cash, and give the owner a reason to keep the card until the timing is right.

The conversation also separates cold outreach from following up with someone who has already responded. Jessey discusses repeat mailing, acknowledges uncertainty in the frequency data, and explains why familiarity with a small area can matter more than the size of a mailing list. He explicitly advises excluding people who have asked not to be mailed again.

The campaign figures are Jessey’s reported observations, rather than independently audited results or a promise of performance. The interview was recorded October 1, 2026; product pricing and mailing rates discussed reflect that conversation and may change.

This is an unpaid conversation prompted by curiosity about the service. Eugene has not tried or endorsed it. Viewers should do their own research, read reviews and compare alternatives.

Jessey Kwong is a co-founder of Pebble, a platform for land acquisition teams. His background includes design, digital marketing, and real estate investing. In the interview, he describes starting as a land investor and building tools to streamline property outreach. He also hosts conversations with investors through Pebble’s podcast.

00:00 — Why land offers get ignored
Guest-led excerpts introduce the unopened-envelope problem, recognizable property imagery and the trust question behind an offer.

01:04 — Land to Legacy introduction
The show introduction.

01:16 — Unpaid conversation and endorsement disclaimer
Eugene explains that the episode is unpaid, he has not used or endorsed the service, and listeners should research independent reviews and competitors.

01:50 — Finding land to acquire
Eugene frames the gap between development execution and finding a property worth pursuing.

02:23 — From land investor to outreach platform
Jessey describes his land-acquisition background and why he built tools to connect outreach with the resulting conversations.

04:21 — Why direct mail deserves a closer look
Eugene questions direct mail after his own disappointing experience; Jessey argues for examining the message and outcome rather than treating all mail alike.

06:34 — Postcard formats and completed acquisitions
Letters, larger postcards and 4×6 cards are compared. Jessey distinguishes reported acquisitions from response rates and connects limited space with clearer copy.

08:58 — Choose the property list before the card
The discussion separates parcel-data filters and local market selection from the outreach system used after a list is chosen.

11:16 — Make the message specific to the owner
Owner names, acreage and relevant property facts turn a generic approach into an identifiable proposition.

13:14 — Use an image of the actual parcel
Jessey explains owner-recognizable imagery and shares his reported acquired-deal comparison, rather than a universal performance guarantee.

15:16 — Subscribe and join the conversation
Eugene asks listeners to subscribe and leave a comment to help others discover Land to Legacy.

15:58 — Offer a useful solution beyond cash
The message should address an owner’s real questions, explain the sender’s role and establish credibility instead of relying on a cash-offer slogan.

17:55 — Repeat mailing and response patterns
Jessey discusses second and third outreach rounds and the uncertainty and selection bias in later campaign observations.

20:32 — How often should a campaign repeat
Eugene asks for a practical interval; Jessey acknowledges that he does not have an exact frequency figure and explains the six-month window he has observed.

20:57 — Cold outreach versus an existing conversation
Following up after an owner responds is distinguished from mailing someone who has never engaged.

21:47 — Market knowledge changes mailing volume
Rural investing experience and developers focused on small pockets illustrate why there is no reliable universal mail-volume answer.

24:28 — Turn a filtered list into tracked outreach
Eugene describes parcel filters for size, zoning, ownership tenure and equity; Jessey connects the data to customized mail and tracked responses.

27:04 — Platform and postage costs as recorded
Jessey discusses platform features and October 1, 2026 pricing. Listeners should check current product and mailing rates.

28:45 — Where to find Pebble and learn more
The conversation closes with Pebble’s website, demo and podcast resources.

29:26 — Closing
The Land to Legacy ending.

Pebble · Book a Pebble demo · Pebble podcast

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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.

Eugene Gershman · GIS Companies · Land to Legacy · Apply to be a guest

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A $15,000 house can still become a $200,000 project. Jerry Larkowski bought two Little Rock houses marked for demolition, then faced missing building systems, delayed materials, borrowed-money pressure, and a second project that sold at a loss. The purchase price was only the beginning of the decision.

Jerry joins Eugene Gershman to explain why he favors rebuilding in established neighborhoods, how proximity to a medical campus shaped his rental strategy, and why the condition of the roof and foundation mattered before reconstruction began. He describes changing the first property's finishes and holding it as an Airbnb when the original plan became less attractive.

The conversation moves from individual houses to the numbers behind development: carrying costs, rents that fail to support new construction, vacancy exposure in small multifamily properties, and the difference between improving a single house and improving an adjoining group of properties. Jerry and Eugene also compare their experiences with local approvals and discuss Jerry's expectations for data-center-related housing demand in central Arkansas.

Jerry Larkowski is an attorney, real estate broker, and property investor in central Arkansas who operates under The Larkowski Group at ESQ. Realty Group. Born in Chicago and raised in Arkansas, he says his education, work, homes, and property investments have largely remained within 30 miles of Little Rock.

In the interview, Jerry describes more than 35 years as an attorney, including 25 years in trial practice, followed by work as in-house counsel and a transition into full-time real estate sales. His clients include investors and owner-occupant buyers, and his own projects include restoring small houses in established Little Rock neighborhoods.

00:00 Episode highlights
A preview of the reconstruction decisions, costs, and development questions ahead.

01:03 Land to Legacy introduction
Eugene introduces Real Estate Development: Land to Legacy.

01:14 Jerry Larkowski and central Arkansas
Jerry traces his move from trial law to real estate and the value of working in a familiar market.

04:10 What drives the Little Rock market
Jerry describes the institutions, employment, and location advantages he sees supporting local housing demand.

08:55 Redevelopment versus new subdivisions
Existing neighborhoods offer a different starting point from subdivisions that require new infrastructure.

10:56 Rebuilding houses marked for demolition
Two purchases at $15,000 and $20,000 lead to a discussion of roofs, foundations, missing systems, and the scope of reconstruction.

15:50 Reconstruction costs and the Airbnb decision
Material delays and borrowing pressure change the first project's budget, finishes, and eventual use as an Airbnb.

18:11 The second project and its loss
Jerry explains the second property's sale at a loss and his reasons for considering the adjoining properties and rear access together.

20:14 Borrowing costs and development math
Debt costs, rental returns, and a small house that found a buyer illustrate the importance of testing the full project economics.

22:14 When new construction does not pencil
Eugene describes projects where construction costs outpace achievable rents, even with a very low land basis.

24:16 Fourplexes and vacancy risk
Jerry explains his interest in small multifamily properties and spreading rental income across several units.

26:48 Permits, inspections and local timelines
Their local experiences show how inspections, rezoning, infrastructure, and review calendars can affect the schedule.

30:02 Data centers and housing demand
Jerry shares his expectations for data centers and housing demand; the discussion reflects his outlook at recording.

32:58 Where to find Jerry
Jerry shares his business identity and direct email address.

33:52 Closing
The closing Land to Legacy sequence.

The Larkowski Group official website

Jerry Larkowski LinkedIn

Jerry direct email

Get the free GIS Feasibility Study Checklist

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.

Eugene Gershman

Land to Legacy

Be a guest

GIS Companies

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OVERVIEW
Lisa Wright, founder of Landings, joins Eugene Gershman on Land to Legacy to make the case that your rural land may have just become a fuel stop. While most of advanced air mobility focuses on urban air taxis, Lisa is building North America's largest planned network of vertiports — 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 BIO
Lisa 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 reel
1:23 — Intro reel
1:34 — Lisa Wright interview — main conversation
36:11 — 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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

What does a $47,000 architectural fee actually buy? Tim Derrington breaks down a proposal for a 17,000-square-foot gym in an existing strip center: $7,000 for design and code-compliance work, and $40,000 for coordination and documentation. The example explains why the initial concept can 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.

Tim 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.

00:00 — 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.

Derrington 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/

Lessons 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

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: 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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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.

Babak 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.

00:00 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.

Babak 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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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.

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.

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

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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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.

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.

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

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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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.

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.

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.

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/

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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

Host: Eugene Gershman

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:
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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/.

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