Podcast Summary: The TreppWire Podcast – Episode 380

Episode Title: How Larry Connor Built a Multi-Billion-Dollar Multifamily Machine
Release Date: February 17, 2026
Featured Guest: Larry Connor, Founder and Managing Partner, The Connor Group
Hosts: Hayley Keene & Steven Bushbaum
Length: ~38 minutes

Episode Overview

This episode features Larry Connor, renowned real estate investor, adventurer, and philanthropist. Connor shares his journey founding and scaling The Connor Group into a leading multifamily investment firm. The discussion covers foundational real estate principles, execution-driven strategies, lessons learned from failure, navigating market cycles, the importance of resident satisfaction, risk management (in both business and personal adventures), and a deep commitment to philanthropy and education.

Key Discussion Points & Insights

1. Larry Connor’s Origin Story: Turning Failure into Opportunity

(01:41–04:15)

• Connor attributes his entry into real estate to failure. After a decade in the computer industry, shifting market dynamics and intense competition led to his company's closure, leaving him deeply in debt.
• "We didn't go bankrupt... but I was worse than broke." (Larry Connor, 02:44)
• Rather than seeing this as a setback, Connor saw it as a 'PhD in business,' learning more from failure than from success.
• The Connor Group began with a focus on applying business-operational rigor—people, plans, processes—to real estate, recruiting team members from outside the industry and running multifamily as a high-performance operating business.

2. Timeless Fundamentals vs. Industry Change

(04:45–07:26)

• Despite market evolution, the fundamentals of real estate haven’t changed: execution, operational excellence, and, uniquely for Connor, resident satisfaction.
• The Connor Group leverages real-time data (including AI-powered metrics) to monitor resident satisfaction actively.
  • "If they were satisfied two years ago, doesn't mean they are today, because this is where they live. So it's constantly changing." (Larry Connor, 05:14)
• Resident retention is the key metric: The Connor Group consistently retains over 60% of residents, compared to the industry average of 45-50%, translating to significant bottom-line impact.

3. The Economics of Resident Satisfaction

(08:04–11:18)

• Connor details the direct and indirect costs of tenant turnover (vacancy loss, turn costs, concessions), quantifying the savings from higher retention.
  • "You just saved, straight to the bottom line, $150,000." (Larry Connor, 08:53)
• Satisfied residents are more likely to accept rent increases, contributing to both stable revenue and asset value growth.
  • "The biggest value add play is operations, not the physical facility upgrade." (Larry Connor, 11:35)

4. Operating Philosophy: Simplicity Amid Growth & Strategic Adaptation

(13:06–14:22)

• Success over decades requires continual change, improvement, and a drive for simplicity as organizations scale.
• Connor emphasizes the need to re-evaluate what works as market conditions and organizational size evolve.

5. Navigating Market Cycles: From Boom to “Normalization”

(14:22–17:20)

• The unprecedented run from 2011–2022 (with low interest rates and high liquidity) led to compressed cap rates and surging valuations in multifamily.
• Connor sees this era as over, predicting a return to historical norms: higher cap rates, normalized rent growth.
• "We think all of that is over. We think it all changes and you go back to what we would call a more historically normalized market." (Larry Connor, 15:57)
• Historically exceptional returns (30%+ IRR after fees) likely won’t repeat; future expectations are more moderate (20–25% range).

6. The “Down the Fairway” Acquisition Model

(17:32–19:44)

• Ideal deal:
  • Suburban location, <=325 units
  • Great floor plans and school districts
  • Amenity and operational upside
• Internal proprietary grading system evaluates properties.
• The Connor Group is not a long-term holder; targets 24–36 month hold periods, with value created and monetized through sale or refinance.
  • "We're going to buy this $85 million business... improve customer satisfaction... and then in 24 to 36 months we're going to do a capital event." (Larry Connor, 18:57)

7. Debt Strategy Tailored to Hold Period

(20:15–21:43)

• Prefers short-term bank debt (matched to hold period), hedged with rate caps or swaps. Fixed agency debt is less optimal due to shorter hold times.
  • "The optionality that term and cap structure gives you is so incredibly valuable." (Host, 21:32)

8. Talent & Culture: Recruiting from Outside the Industry

(22:30–23:20)

• The Connor Group’s operating model requires extensive training and cultural alignment; managers undergo 5-month onboarding.
• Fast pace and high achievement are core; most hires have no prior industry experience.

9. Multifamily Investing: The Active Business, Not a Passive Investment

(23:30–24:17)

• Major misconception: Multifamily is “passive.” In Connor's eyes, each asset is an operating business, requiring active management and engagement—not third-party management and a “set it and forget it” approach.

Philosophy of Risk, Challenge & Purpose

(24:17–25:21)

• Connor's approach to adventure (space, deep sea, extreme sports) mirrors his business strategy: Only pursue endeavors that are both challenging and purposeful, and never accept unmanaged or unacceptable risk.
  • “We won’t do anything unless it’s challenging and has a purpose… we have to be able to manage this risk... we will not take any unacceptable risk.” (Larry Connor, 24:42)

Most Meaningful Endeavors

(25:35–27:35)

1. Connor Group Kids & Community: Pioneering non-denominational private school for under-resourced youth in Ohio, now a model under national consideration.
2. Building The Connor Group: Scaling a company from scratch, delivering substantial benefits to team members (70 partners through sweat equity) and investors.
3. Pursuing the Impossible: Willingness to attempt radically ambitious projects and overcome uncertainty.

Education, Philanthropy & Impact

(27:35–29:26)

• Advocates for revolutionary—not evolutionary—change in American education, particularly for under-resourced children.
• Experiments with AI-powered individualized tutoring to improve learning outcomes, showing initial promise.
  • "It's Simply a matter of the right people, the right plans and the right funding." (Larry Connor, 28:22)

[Notable Segment] Connor’s Space & Adventure Stories

Axiom Mission 1 (International Space Station Pilot, 2022)

(30:06–32:43)

• First all-private civilian mission to the ISS; Connor served as pilot aboard SpaceX Crew Dragon.
  • "It's a SpaceX Crew Dragon capsule, really automated... SpaceX is a phenomenally talented company with all kinds of safety measures built in." (Larry Connor, 30:26)
• Unexpected 7-day extension, with free time spent calling friends and colleagues from the ISS—surprising and delighting recipients.

High-Altitude Balloon Skydive Record

(32:43–35:42)

• Detailed behind-the-scenes look: Largest US-built hot air balloon, piloted to 38,000 feet over Roswell, NM, before skydiving as a team.
• Faced critical equipment failure (oxygen mask froze) at peak altitude, resolved through training and composure.
  • “If you can't breathe, about your only option would be to jump off of the gondola and hope you got down to altitude...” (Larry Connor, 34:04)
  • “...You gotta stay calm. Let's figure this out.” (Larry Connor, 35:25)

Final Advice for Listeners

(36:21–36:42)

• "Aim high. Do not self-limit. You and your mind are capable of much more than you think you are. You will never outperform your own self-image." (Larry Connor, 36:23)

Memorable Quotes

• On Failure:
  "You learn a lot more through failure than you do success." (Larry Connor, 02:17)

• On Resident Satisfaction:
  "You're far better off retaining residents than making a transactional business." (Larry Connor, 05:36)

• On Value Creation:
  "The biggest value add play is operations." (Larry Connor, 11:35)

• On Risk:
  "We will not take any unacceptable risk." (Larry Connor, 24:58)

• On Possibility:
  "You will never outperform your own self-image." (Larry Connor, 36:38)

Notable Timestamps

• 01:41 – Larry’s background and transition to real estate
• 04:45 – Timeless fundamentals vs. what’s changed in multifamily
• 08:04 – Hard-dollar math of tenant retention
• 11:35 – “Operational value-add” vs. physical upgrades
• 13:06 – Lessons from multiple cycles; embracing change, simplicity
• 15:57 – Market outlook: normalization after boom years
• 18:57 – “Down the fairway” property profile & investment thesis
• 22:30 – Recruiting, culture, building talent in an unconventional way
• 23:30 – Misconceptions about passive investing in multifamily
• 24:42 – Philosophy of risk and purpose in business and adventure
• 25:35 – Philanthropy and educational innovation
• 30:06 – Story: Calling from the International Space Station
• 32:43 – Story: Record-setting balloon skydive and dealing with danger
• 36:23 – Final advice: “Aim high. Do not self-limit.”

Conclusion

Larry Connor’s journey offers a blueprint for building enduring success in multifamily real estate—rooted in operational discipline, people-first culture, and an unwavering commitment to positive impact. The episode delivers both concrete real estate wisdom and larger lessons on risk, resilience, and leadership, capped by high-stakes adventures and extraordinary acts of philanthropy.

For further information about The Connor Group or their philanthropic initiatives, visit their official website or the Greater Dayton School site.