Exclusive Video Interview with Larry Connor

“People work for people, not companies. Leaders must inspire and motivate their teams.”
Larry Connor, the founder and Managing Partner of The Connor Group, a $5 Billion+ in assets under management real estate investment firm, is not your typical business leader. His success, as you will hear from the interview, is not just about his values, but also his unique way of thinking about scaling and his bold rejection of industry norms. His approach challenges what people think is even possible, inspiring us to think outside the box.

Larry has ventured to the deepest parts of the ocean and into space, taken a hot air balloon up to 38,139 feet, and set a world record by jumping off while raising over $1 million for charity. He has also indulged in mountain climbing, rafting, and various forms of racing. In my recent interview with Larry, we didn’t dig to much into these adventures, but I loved the interview. His dynamic nature and insightful advice kept me engaged throughout.

Richard C. Wilson: Great, welcome Larry.

Larry Connor: Thank you.

Richard C. Wilson: Appreciate you being here. So we did an interview virtually recently and it went great, and we appreciate that. Larry got started in 1991 with a couple of partners in the real estate space. He had only one investor when he got started. He owned nothing, was running on borrowed time, and the only thing he had was an idea to bring a completely different model to the business of apartments and multi-family. He bought out his partners and created the Conner Group in 2003. Today, they’re a thriving real estate investment firm specializing in luxury apartment communities with over $5 billion in assets across 18 different markets. Larry is one of the few people who’s been to outer space as well as the deep sea. And now, he’s been to a family office super summit. Thanks for being here.

Larry Connor: Appreciate it, thank you.

Richard C. Wilson: Yeah, what else would you add about your background? Anything related to where you grew up, family, or anything like that that you think would be good for everyone to know before we get started?

Larry Connor: So, I was not a good student. I barely made it through high school. I lived in the Midwest, great area, and didn’t have to worry about touring campuses and colleges because my grades were so bad. In the stable high school, if you graduated from high school, there was one school—Ohio University—that had to take you. Literally, at orientation, they said, “Look to your right, look to your left. One or both of those people won’t be here at the end of the year.” They had a 50% flunk-out rate in the first year. So I managed to get in there and stay in. If you ask about my background, finance, economics, business—none of the above. I was an English major with a concentration in Shakespearean literature, which qualifies me for nothing. We’ve owned and separated eight different businesses—seven of them were very successful. One, a computer business, was a failure, but we learned from all of those. We’ve actually owned three technology companies, and I came out of the computer industry when we started the Conner Group in 1991.

Richard C. Wilson: Awesome. Appreciate you sharing that. That’s great, especially the part about being a bad student. You know, as kids, it’s almost like the only grade you get on your value on planet Earth is your grade in school, right?

Larry Connor: Exactly.

Richard C. Wilson: So, what was the turning point for massive increased momentum? Was there a specific moment where once you acquired that one asset or did that one thing, everything just took off?

Larry Connor: We believe that it’s a process. The process was one of failure. When we started in ’91, neither my partners nor I were from the industry. We knew about operating businesses, and so we said, “We’re just not going to pay attention to conventional systems, processes, norms, and beliefs. We’ll chart our own path.” We did a lot of things right, but made a number of mistakes. We weren’t afraid to make mistakes—not reckless, but we weren’t afraid of making them. The difference was, from those failures, we owned them. We didn’t make excuses. We learned from them, changed quickly, and just continued to get better. That’s been a 32-33 year process. In fact, we did our first acquisitions in ’92. In 2024, we have a mantra of change, simplify, and improve. We have 90+ different initiatives going on this year. Some are things we should have changed five or six years ago, and others are new and innovative. We believe in reinventing yourself and being different, not just surface-differently, but disruptive-differently. For us, it’s always a learning process.

Richard C. Wilson: That’s great feedback. Many people here in the room meet a lot of people each year, and if you’re saying the same thing as everyone else, I don’t know how you can get a reply or engage a partner. That’s fantastic feedback for everyone here to hear, whether on the investor or founder side. What’s a million-dollar strategy that founders and investors could take away from today’s discussion?

Larry Connor: I wouldn’t think about a million dollars; that’s the hoped-for outcome. I’d think more about the process. What I would do—what we do, by the way, we have a real estate firm with about $5 billion in assets, and we also own an investment firm managing about $750 million—I’d think about the results I’ve historically achieved. Are they what I want? For example, if you’d like to compound at 14% but are only compounding at 8%, I’d go back and really do a self-inventory. What are my beliefs, philosophies, strategies, and why aren’t I getting the results? I’d then make thoughtful, planful changes in systems, processes, analytics, etc. In our experience, if you do the right processes with the right people and the right plan, the outcomes will generally take care of themselves.

Richard C. Wilson: Interesting. The founders of Home Depot set out to have a thousand stores before they even had one. Some people say you need a clear vision and just work your butt off to make it happen. But for you, back in 1991, did you have huge goals, or were you just focused on knocking out what’s right in front of you, taking it one step at a time?

Larry Connor: No, we just started down the path. We wanted to be successful. We knew we couldn’t do it alone. We always believed in people, plans, and culture. We focused on our operating business. Real estate for us, by the way, is a differentiator. Technically, we’re in the real estate business, but we consider ourselves professional operators of operating businesses that happen to be apartment communities. We run them like businesses. We also believe we’re pretty good investors, and we focused on performance, putting the investor first. A lot of people say they do that, but if you look at how they structure deals, it’s not truly performance-oriented. Ours are. If we don’t deliver, we get nothing because we deserve nothing. With that mindset, after 32 years, our average annual IRR return to investors after fees is over 30%. In the last five years, it’s around 38%. We’ve done 241 acquisitions over that period and lost money on eight.

Richard C. Wilson: So, back to your earlier point about breaking the mold. I remember you mentioned how other people would hire maintenance crews to handle six tickets a day, but you aimed for 20 tickets a day. You broke assumptions like that across the business. Can you expand on that?

Larry Connor: We hire no one from the industry. Our site people, managers, sales, and service staff—no one. We tried hiring a few people early on, but they thought we were crazy and couldn’t change their habits. So we stopped. It’s harder to find the right people, but we invest millions annually in training. If you want to be exceptional, you can’t be like everyone else. You’ve got to be smart and different. For example, in the industry, workers typically handle six to 10 tickets per day. Our technicians handle 20 to 25 per day. We focus on accountability, teaching, and recognizing achievement.

Richard C. Wilson: What’s a costly mistake you’ve learned the hard way that could help investors and founders here avoid it?

Larry Connor: We’ve all tried hard to hire the right people. We believe that 90% of your problems are people problems, and 90% of your solutions come from people. The mistake we made, and many others make, is not recognizing quickly enough when someone isn’t right for the role. If they lack competence or commitment, honestly identifying that as a problem and making a change is better for both the person and the business in the long run.

Richard C. Wilson: Do you want to talk about the culture book that you’ve generously gifted to everyone here, its importance, and how you use it?

Larry Connor: We believe culture is foundational. If you gather a group of people who share the same commitments and philosophies, and aim high, you can do the impossible. About seven or eight years ago, someone suggested we write a book about our culture. We didn’t do it to publish it, but for our associates. We updated it a few years ago. If you read it, you’ll understand who we are. Culture isn’t about mission statements or plaques on the wall—it’s about actions and deeds.

Richard C. Wilson: Some say billionaires just get lucky. What would you say to that?

Larry Connor: It doesn’t work that way. There’s no shortcut to success. You can get lucky, but what lasts long-term is rooted in people, grit, and perseverance.

Richard C. Wilson: You’ve been quoted as saying we have a fundamental responsibility to share wealth. Why is that important?

Larry Connor: We believe in sharing wealth. If you’ve been fortunate and successful, you have the opportunity and the obligation to give back. We do that through various programs for kids and communities, particularly underserved ones. We’ve invested in revolutionary programs like the first private school in Ohio focused on under-resourced kids, and we’re looking to expand it nationally. Over the next 10 years, we’ll invest around $800 million in philanthropic initiatives.

Richard C. Wilson: You’ve done remarkable things, including going to outer space and the deep sea. How have personal endeavors like that influenced your business?

Larry Connor: We only pursue these challenges if there’s a purpose, and they must be safe and successful. The lessons learned in these ventures carry over to business. Blazing new trails—whether in investing or business—means stepping outside your comfort zone. It’s not easy, but it gets easier with time.

Richard C. Wilson: What personal values or mindset do you think have helped you scale and execute at a high level?

Larry Connor: It’s not about how much money you have—it’s about the four P’s: People, Plan, Processes, and Perseverance. If you have the right people, a solid plan, effective processes, and the perseverance to see it through, your chances of success are high.

Richard C. Wilson: What’s the best advice you can give someone who wants to build a high-performing business?

Larry Connor: Aim high. You’ll make mistakes along the way, but the key is to not stop. If you do it right, you’ll be rewarded, and if you don’t give up, you’ll eventually get where you want to go.

Richard C. Wilson: Larry, this has been incredible, thank you so much for sharing your insights and wisdom. Appreciate it.

Larry Connor: My pleasure. Thank you for having me.

Here are my top 6 takeaways that I noted, but please stream the whole video above to see why I found it so valuable.

  1. You have to be innovative – disrupt the industry – be wildly different and focus on what others say is impossible.
  2. Hire for values and personality – do not hire people in your industry; expect 2-3x what others expect from your staff.
  3. Only do what is safe and successful – be willing to take calculated risk, not stupid risk.
  4. Do not ever compromise on team members, no B players – surround yourself only with people who are excellent, innovative, proactive and whose values align with yours.
  5. Do exciting, adventurous things – be willing to expand your brain, body, and health to grow professionally and personally.
  6. There is so much opportunity due to poorly run assets – The Connor Group runs real estate like it is a business, and it pays people on results/profit not on revenue; the company can’t find experienced real estate people who fit the demands of his company and culture.

Richard C. Wilson: Hello, everybody. Richard C. Wilson here. Today, we have an exciting interview with Larry Connor, founder of the Connor Group, known for building billions of dollars in real estate assets, particularly in apartment buildings and multifamily real estate. Larry, welcome to the interview!

Larry Connor: Thank you, Richard. It’s great to be here.

Richard C. Wilson: To start, could you give us some background on how you founded the Connor Group and a bit about your personal journey?

Larry Connor: Sure. We started the Connor Group in 1992. Before that, I was involved in the computer industry and had some investing experience on the side. Unfortunately, our computer company failed after nine years, which was a tough but valuable learning experience. We decided to enter the real estate industry with a new perspective, focusing on luxury apartment communities. Currently, we have properties in 18 cities across the U.S. and about $5 billion in assets. Our approach is to treat these apartment communities as operating businesses rather than passive investments, which has been our core strategy for over 30 years.

Richard C. Wilson: That’s impressive. Competing with institutional buyers at your scale must be challenging. How does your operational expertise give you an edge?

Larry Connor: Institutional owners typically maintain properties well but outsource management. They get paid based on the top line, whereas we focus on improving the bottom line through exceptional resident service. Our approach allows us to capitalize on the operational inefficiencies left by these institutional owners, providing us with significant opportunities to enhance performance.

Richard C. Wilson: What was a turning point in your career?

Larry Connor: In 1990, we had a computer company based in Orlando, Florida. We became the second-largest reseller of local area networks in the state but eventually went out of business due to margin pressures and capital constraints. At 40, with a family to support, we had to start over. We took the lessons from that failure and applied them to real estate, focusing on hiring for cultural fit and adopting a fresh perspective.

Richard C. Wilson: For someone just starting in real estate today, what advice would you offer?

Larry Connor: Success relies on the four P’s: getting the right people, having a plan, building processes, and maintaining perseverance. Financial resources are secondary to these foundational elements. Whether you’re entering real estate or any other industry, these principles are crucial.

Richard C. Wilson: What’s a common mistake you see people making that they could easily avoid?

Larry Connor: A common mistake is focusing on short-term gains rather than long-term strategy. Managing for immediate results without a comprehensive plan is not a winning approach. A long-term vision is essential for sustained success.

Richard C. Wilson: You mentioned not hiring from within the real estate industry. Why is that?

Larry Connor: We find that industry veterans often have different expectations and productivity standards that don’t align with our approach. To be exceptional, we need to be dramatically different. Hiring from outside the industry brings a fresh perspective and better aligns with our values and standards.

Richard C. Wilson: How do you build and manage a high-performance team?

Larry Connor: People work for people, not companies. Leaders must inspire and motivate their teams, set high expectations, measure accountability, and invest in their development. Talented individuals thrive when challenged and supported. We don’t tolerate mediocrity; we strive for excellence and continuous improvement.

Richard C. Wilson: If an employee isn’t meeting expectations, do you focus on improving them or consider letting them go?

Larry Connor: We invest in coaching and development, but we maintain high standards. If someone doesn’t meet those standards despite thorough evaluation and support, we don’t compromise on performance. It’s about ensuring that everyone on the team is aligned with our goals and values.

Richard C. Wilson: You’ve achieved remarkable things, including space travel and deep-sea exploration. How do these personal adventures influence your business?

Larry Connor: These adventures require rigorous preparation and perseverance, qualities that are essential in business as well. Stretching your limits and challenging yourself helps develop resilience and innovation. It’s about pushing boundaries and learning from those experiences, which in turn benefits your professional endeavors.

Richard C. Wilson: If you were mentoring someone on building a high-performance business, what additional advice would you offer?

Larry Connor: Focus on passion and purpose rather than just financial gain. If you find something you’re passionate about and align it with your values, success is more likely to follow. Purpose-driven work provides an edge that others can’t easily compete with.

Richard C. Wilson: Thank you, Larry. This has been a fantastic conversation. I’m sure our audience will find your insights incredibly valuable.

Larry Connor: Thank you, Richard. It’s been a pleasure.