Podcast
DevelopLex
Hosted by Middle Tech · EN
DevelopLex is a podcast diving into the ins & outs of real estate development and investing here in Lexington, Kentucky. This series will feature interviews with some of Lexington's most prominent real estate developers that have played a major role in building Lexington into what it is today.
20episodes
Episodes
Newest firstAll episodes
83. Democracy by Design: How Richard Young & CivicLex are Making Local Government More Representative
Dec 1200:39:43Tap to summarizeWhat would it look like if everyday Lexingtonians - not just elected officials - had a direct hand in shaping how the city works? That’s exactly what Richard Young and his team at CivicLex are putting into motion with a groundbreaking Civic Assembly and a once-in-a-generation review of Lexington’s city charter.In this episode of DevelopLex, Ross sits down with Richard to unpack the bold new approach CivicLex is taking to improve Lexington’s civic health - the city’s ability to make decisions that reflect the values, needs, and diversity of its people.Richard explains how CivicLex grew from a local project into a nationally recognized model for civic engagement, and why updating the city charter could be the most important local effort you haven’t heard about - until now.Through a process modeled after jury duty (but way more empowering), CivicLex is selecting 36 random, representative residents to deliberate on major topics like council structure, redistricting, and public input and recommend changes that could directly shape Lexington’s future.In this episode, you’ll hear:- Why the city charter is Lexington’s version of a constitution and why it matters- How CivicLex is using sortition to build a Civic Assembly that mirrors the city- What “civic health” means and how it impacts development and governance- Why this charter review process is Lexington’s most democratic effort in decades- How this model could be used for other contentious local issues- What it takes to engage people meaningfully, not just performatively, in governmentHosted by: Ross BoggessSupported by:SVN Stone Commercial Real EstateCraftsman ContractorsBowmanCommunity Trust Bank
Transcribe →82. The Blueprint for Scale: Lee Greer of Greer Companies on Cheddar’s, Activate, and What’s Next
Nov 2000:48:09Tap to summarizeWhat does it take to scale a business from a single restaurant in Kentucky to a nationally recognized brand? Few people understand that blueprint better than Lee Greer, President of Greer Companies - the force behind Cheddar’s national expansion, the real estate portfolio that underpins the company, and the global rise of Activate through Sounds Fun Entertainment.In this episode of DevelopLex, Weston and Ross sit down with Lee to unpack the strategy, discipline, and culture that have defined Greer Companies for decades. From raising hundreds of millions on Wall Street to working every station in a Cheddar’s kitchen, Lee shares how those experiences shaped the systems-driven, people-first approach that he now applies across restaurants, entertainment concepts, and real estate development.Lee breaks down the story behind the Cheddar’s exit - including the last-minute negotiation move that added $72 million to the deal - and how that capital helped fuel significant projects in Lexington like City Center. He also explains why Activate became the perfect next venture: a concept built on physical and mental challenges, designed for repeat play, and structured with low labor and no cost of goods.In this episode, you’ll hear:- How Wall Street deal-making trained Lee to think in scale, systems, and returns- Why Cheddar’s succeeded through culture, consistency, and operational discipline- The behind-the-scenes story of the Cheddar’s exit and how it reshaped Greer Companies- Why Activate’s experiential model is built for global growth and why it works- How real estate remains the backbone of Lee’s long-term investment strategy- What Lexington needs to unlock its next stage of intentional growthHosted by Weston Lockhart and Ross BoggessDevelopLex is proud to be supported by:SVN Stone Commercial Real EstateCommunity Trust BankCraftsman ContractorsBowman
Transcribe →81. From the Pentagon to 325 W Main: How Katie Kaufman Went from National Security to Building a Lexington Landmark
Nov 600:48:12Tap to summarizeWhat does it take to go from working at the Pentagon to shaping Lexington’s main street? Developer Katie Kaufman is doing exactly that with her newest project: 325 W Main, a landmark development redefining downtown Lexington’s future.In this episode of DevelopLex, Weston and Ross sit down with Katie to explore her unconventional path from national security and global development finance to leading one of the city’s most ambitious real estate projects. Katie shares how her time in Washington, D.C. and at the U.S. International Development Finance Corporation taught her to think globally, and how she’s now applying that experience locally to build spaces that are inclusive, beautiful, and community-driven.At 325 W Main, her team is creating a new standard for downtown Lexington development - one that blends high-quality design, hospitality, and everyday usability while staying rooted in the city’s character.In this episode, you’ll hear:- How Katie’s Pentagon background shaped her leadership and perspective on real estate- What inspired her transition from national security to development- The design philosophy behind 325 W Main and its role in Lexington’s evolution- Why inclusion and empathy are key to building better cities- How Lexington can compete for new investment and talent through design and collaborationHosted by Weston Lockhart and Ross BoggessDevelopLex is proud to be supported by:SVN Stone Commercial Real EstateCommunity Trust BankCraftsman ContractorsBowman
Transcribe →80. Building What’s Missing: Garyen Denning of Red Draw on Market-Driven Development in Lexington and the Need for More Senior Housing
Oct 2300:36:25Tap to summarizeIn this episode of DevelopLex, Weston and Ross sit down with Garyen Denning, partner at Red Draw Development, to explore how his team has built a reputation for identifying what Lexington’s market is missing—and creating it.From introducing Raising Cane’s to Kentucky to developing The Landrum, a new senior living community designed to meet the needs of a rapidly aging population, Red Draw has consistently leaned into new concepts before the rest of the market catches on. Their portfolio includes everything from public-private partnerships and boutique hospitality projects to The Haven, a collection of luxury auto garages on Delaware Avenue unlike anything else in the city.Garyen shares how Red Draw’s development philosophy blends operator-level insight with community-focused execution, the lessons he learned scaling a franchise before shifting to real estate, and why being early often means being right.Expect to learn:How Red Draw identifies gaps in Lexington’s market and builds to fill themThe story behind the Horse Soldier Distillery, opening July 4, 2026Why The Landrum addresses a critical shortage in senior living housingThe role of public-private partnerships in delivering civic impactHow Lexington’s embrace of infill and density is shaping its next phase of growthHosted by Weston Lockhart and Ross BoggessDevelopLex is proud to be supported by:SVN Stone Commercial Real EstateCommunity Trust BankCraftsman ContractorsBowman
Transcribe →79. How Lexington Is Planning Its Future: Inside the the Lexington Preservation and Growth Management Program with Vice Mayor Dan Wu and Councilwoman Liz Sheehan
Oct 900:39:44Tap to summarizeIn this episode of DevelopLex, Ross and Weston sit down with Vice Mayor Dan Wu and Councilwoman Liz Sheehan at Lexington Council Chambers to unpack the Lexington Preservation & Growth Management Program (LPGMP) - a landmark policy initiative shaping how our city grows, preserves, and evolves over the next 20 years.Together, they explore the critical balance between infill redevelopment and urban expansion, the role of community voice in planning, and why housing is at the center of nearly every challenge Lexington faces. From regulatory red tape to reimagining transportation through Complete Streets, this conversation pulls back the curtain on how public input is influencing the city’s growth, and how you can be part of the process.Whether you're a developer, a neighbor, or just passionate about Lexington's future, this one’s for you.Hosted by Weston Lockhart and Ross BoggessDevelopLex is proud to be supported by:SVN Stone Commercial Real EstateCommunity Trust BankCraftsman ContractorsBowman
Transcribe →78. Beauty in the Built Environment: Jon Carloftis on Garden Design, Restoration, and the Spirit of Kentucky
Oct 200:42:43Tap to summarizeIn this episode of DevelopLex, Weston and Ross sit down with legendary garden designer Jon Carloftis at his restored downtown Lexington home - known locally as “The Botherum”. From humble roots in Eastern Kentucky to designing rooftop gardens in New York City, Jon shares his journey of passion, intuition, and preservation and the importance of beauty in the built environment.Now back in Kentucky, John is helping redefine how we experience place, from Castle & Key and Maker’s Mark to The Summit at Fritz Farm. His approach to landscape design goes beyond aesthetics - it’s about enhancing how people feel, move, and connect within a space.Hosted by Weston Lockhart and Ross BoggessDevelopLex is proud to be supported by:SVN Stone Commercial Real EstateCommunity Trust BankCraftsman Contractors Bowman
Transcribe →77. Retail That Sticks: Kyle & Tom Jameson on Creating Successful Shopping Centers w Compass Capital
Sep 1800:53:01Tap to summarizeIn this episode of DevelopLex, Weston and Ross sit down with the father-son duo behind Compass Capital - Tom and Kyle Jameson - for a deep dive into Lexington-based retail real estate. From buying Lexington Green out of receivership at a 12-cap to running a successful campaign to legalize alcohol sales in Jessamine County (yes, really), the Jamesons share decades of hands-on lessons in ownership, operations, and opportunity.If you’ve ever wondered how local developers position themselves to win during market downturns, build sticky tenant lineups, or transform struggling retail centers into thriving community hubs, this one’s for you.Hosted by Weston Lockhart and Ross BoggessDevelopLex is proud to be supported by:SVN Stone Commercial Real EstateCommunity Trust BankCraftsman Contractors Bowman
Transcribe →76. Knee-Deep in Town Branch: Ross & Weston Wade Through Where Lexington Began and Where It’s Going
Aug 700:54:48Tap to summarizeIn this episode of DevelopLex, we go creekside with hosts Ross Boggess and Weston Lockhart at Town Branch Creek, the literal birthplace of Lexington, to talk about where the city began and where it’s going.What starts as a reflection on Lexington’s founding waterway flows into a wide-ranging conversation about real estate, infrastructure, population shifts, public-private partnerships, and the vision required to advance a city. From the evolution of the Distillery District to new developments around UK’s campus, Ross and Weston explore how Lexington is stitching together neighborhoods, activating forgotten spaces, and attracting long-term investment.This episode also dives into key insights around urban growth patterns, tax base challenges, crane counts as economic indicators, and how Lexington stacks up against cities like Charleston and Atlanta. The message? If we want a better Lexington, we can’t just grow — we have to advance, intentionally.Recorded in the water (literally), this is one of our most rooted and reflective episodes yet.Hosted by Weston Lockhart and Ross BoggessDevelopLex is proud to be supported by:SVN Stone Commercial Real EstateCommunity Trust BankCraftsman Contractors Bowman
Transcribe →75. Why Lexington SC Is More Than Soccer: Steven Dawahare on a Playbook for Community-Driven Development
Jul 2500:44:22Tap to summarizeIn this episode of DevelopLex, we sit down with Stephen Dawahare, longtime Lexington entrepreneur and real estate developer, to talk about the bold vision behind Lexington SC and how it’s become one of the most impactful developments in Central Kentucky.What started as a soccer project has grown into a $100M+ privately funded ecosystem on Lexington’s east side, complete with pro-level facilities, youth programming, and strategic commercial development. But this isn’t just about sports. It’s about long-term city planning, infrastructure, and access - especially for kids and communities historically left out of elite athletics.Stephen walks us through how the project came to life, what it took to move literal mountains (and rock), and why Lexington SC is built to be both economically sustainable and deeply meaningful.Hosted by Weston Lockhart and Ross BoggessDevelopLex is proud to be supported by:SVN Stone Commercial Real EstateCommunity Trust BankCraftsman Contractors Bowman
Transcribe →74. Donald Miller, Ben Shaffer, Carter Bishop, & David Dean: Making Gatton Park a Reality
Jul 300:29:10Tap to summarizeIn this episode, we partnered with Downtown Lexington Partnership to host another Downtown Deep Dive, presented by Dean Builds. This time, with the visionaries behind Gatton Park on the Town Branch - Lexington’s most ambitious public space project to date. Recorded overlooking the park’s soon-to-be-unveiled amphitheater, this conversation dives into the decade-long journey from asphalt lot to iconic green space.Guests:David Dean, President of Dean BuildsBen Schaffer, Senior Director of Advancement & Special Events, Gatton ParkDonald Miller, Park Director, Gatton ParkBishop Carter, Owner of Elaine AllenHosted by Weston Lockhart & Ross BoggessDevelopLex is proud to be supported by:SVN Stone Commercial Real EstateCommunity Trust BankCraftsman Contractors Bowman
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