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Morning Walk: Gary Sheng, Matt Holm, Dan Hollander

Date: June 8, 2025
Location: Austin, TX
Format: Walking conversation

Executive Summary​

A wide-ranging conversation during a morning walk covering real estate development challenges, modular housing innovations, AI's impact on labor markets, and personal relationship dynamics. Dan Hollander, a real estate developer with NYC background, joins Gary and Matt for discussion about industry trends, Matt's ongoing divorce situation, and potential business collaborations.

Key Participants​

Dan Hollander - First Documented Interaction​

  • Real estate developer, originally from New York (28 years experience)
  • Moved to Austin area ~4.5 years ago
  • Air Force background, father also served Air Force
  • Currently focused on residential development, pivoting to "con for-sale" projects
  • Has 23-year-old and 3-year-old children from different relationships

Major Discussion Themes​

Real Estate Market Conditions​

Dan provided ground-level perspective on current market challenges:

  • Market Slowdown: "Well, yeah, ever since grades went up. Oh, yeah. It's just been very tough. But residential is real estate."
  • Strategic Pivot: Transitioning from rental properties to for-sale condos due to market conditions
  • Development Challenges: Discussed how interest rate increases have essentially frozen new residential starts

Modular Housing & Affordable Solutions​

Significant discussion about Lael Alexander's modular housing factory in Tulsa:

  • Cost Innovation: Gary explained Lael's ability to build one-bedroom modular houses for ~$100k
  • Scale Opportunity: "We were just with the Tulsa mayor's office. We're gonna help them achieve their affordable housing goals. At least 8,000 new houses by the time the term is up."
  • Breakthrough Necessity: Gary emphasized: "Literally just, oh, we're going to use taxpayer dollars to build the same cost as Palgic. It has to be, like, literally a breakthrough in cost."

Labor Market & AI Automation Discussion​

Extended conversation about workforce challenges and automation:

  • Immigration Impact: Gary noted the contradiction: "We are a nation of influencers and salespeople... And we've decided to stop importing Mexicans. That's a really bad decision from your perspective."
  • Skills Gap: Discussion about encouraging liberal arts education while lacking practical skills
  • Future Job Categories:
    • Jobs requiring personal relationships will remain human-dominated
    • Manual trades will be protected until robots can get certifications
    • Routine analytical work is most vulnerable to automation

Key Quote from Gary: "A robot is not replacing relationship building anytime soon. Any relationship building matters... But if you were mindlessly doing shit, it's going to be difficult."

Development Economics & Parking Insights​

Dan shared industry expertise on development margins:

  • Parking Economics: "Nobody goes less than 1 to 1 parking distance... It's essentially you're building housing around the giant parking facility. That's your whole margin right there, right?"
  • Cost Structure: Explained how parking requirements fundamentally drive real estate development economics
  • Future Disruption: Anticipation that autonomous vehicles will dramatically reshape development patterns

Matt's Personal Situation​

Continued discussion of Matt's divorce proceedings:

  • Strategic Approach: Matt taking non-emotional, business-like approach to divorce
  • Timeline: Divorce expected to finalize by end of summer 2025
  • Personal Growth: Matt acknowledged need to learn dating skills after being in committed relationship since age 23
  • Support Network: Discussion about learning from friends like Adrian who are skilled at dating

Key Quote from Matt: "My biggest thing was to resist the urge to immediately jump into a committed relationship. I need to learn how to have fun too while not getting STDs."

Business Development Opportunities​

Jewish Schools Project (NYC)​

Gary described major opportunity:

  • Scale: "There's a million private school students that are Jewish in New York City alone"
  • Problem: Schools being threatened with closure for not meeting NY state standards
  • Solution: Software Gary consults for could help schools meet compliance requirements
  • Networking: Gary attending Auschwitz Memorial Gala - "$10,000. Literally cost me with this. If the deal goes through, I'm gonna make sure I'm reimbursed."

Modular Housing Collaboration​

Discussion of potential partnerships:

  • Dan's expertise in residential development
  • Gary's connection to Lael Alexander's manufacturing capability
  • Tulsa mayor's office affordable housing initiative
  • Potential for Dan to visit Tulsa factory operations

Strategic Insights & Quotes​

On Manufacturing Renaissance​

Gary: "There's so many things that need to happen for manufacturing to be back. It's such wishful thinking right now... You tell factory builders, you can't import the foreign labor that has the specialized talent... and you also, we have decades of shortage of People that could actually run and work in those factories."

On Real Estate Innovation​

Dan: "You can build a one-bedroom with one bedroom modular house for like 100k. Exactly. And you can pump them out. Right. So that's what we need. It's just convincing the towns that it's not... Lowering their property values?"

On Skills Development​

Gary: "We have a critical window right now over the next 10 years to building up capital capacity. Where we can have managers of the robots, right? So now it's happening, and so people are not ready."

On Personal Growth​

Matt: "I almost feel like I'm older and wiser, but I'm like arrested development of 23 relationship-wise. The last time I dated, there weren't even cell phones. There was no internet."

Follow-Up Actions & Potential Collaborations​

  1. Dan-Lael Connection: Potential for Dan to visit Tulsa factory and explore modular housing partnerships
  2. NYC Jewish Schools: Dan's Orthodox community connections could be valuable for Gary's NYC project
  3. Affordable Housing Initiative: Collaboration opportunities around Tulsa's 8,000 unit goal
  4. Walking Group Continuity: Discussion about maintaining walking group even when Matt travels

Business Network Expansion​

This conversation represents Gary's continued strategy of connecting experienced professionals (Dan's real estate expertise) with innovative solutions (Lael's manufacturing capability) while maintaining personal relationships through regular informal settings like walking groups.

Key Relationship Dynamics​

  • Gary serving as connector and strategic advisor
  • Matt dealing with personal transition while maintaining business focus
  • Dan bringing industry expertise and NYC connections to Austin network
  • Shared interest in addressing housing affordability crisis through innovation

The conversation demonstrates Gary's approach of using casual settings to explore serious business opportunities while supporting friends through personal challenges.