
Family Office Podcast: Billionaire & Centimillionaire Interviews & Investor Club Insights
The Family Office Podcast released 3-7 episodes a week of interview mandate interviews, private investor strategies, innovative investment structures, and wealth management related insights.
We use this podcast to interview billionaires, centimillionaires, investors, and family offices and help founders, entrepreneurs and investors scale their platforms and invest more effectively.If you are looking to grow your business, get sharper at investing and scale you are in the right place.
Our program provides investors with insights on setting up their own single family office, virtual family office, or selection of a multi-family office to help them manage their wealth.
We cover private equity, real estate, income investments, commercial real estate, hard money lending, private loans, and innovative structures such as performance-fee only and Co-GP investment opportunities.
The Family Office Club has over 7,500 registered investors and our online investor community has over 700 recorded investor mandates, with a normal 15 live events hosted a year with 6,500 participants at those live events.
To learn more please visit http://FamilyOffices.com or text (305) 333-1155
Family Office Podcast: Billionaire & Centimillionaire Interviews & Investor Club Insights
From Zero to $5 Billion: Journey of Reinvention in Luxury Real Estate
Join Richard C. Wilson as he sits down with Larry Connor, founder of The Connor Group, in this compelling Billionaire Fireside Chat. Larry shares his journey from humble beginnings in Ohio to building a thriving real estate investment firm with over $5 billion in assets across 18 markets.
In this candid conversation, Larry discusses:
Overcoming failures and the power of perseverance.
Building a performance-driven culture and empowering employees.
The importance of innovation and breaking industry norms.
Philanthropy and giving back through impactful initiatives.
Insights from his personal adventures to outer space and the deep sea.
Learn how Larry's unique mindset, focus on people and process, and relentless drive for excellence have propelled his success. Whether you're an investor, entrepreneur, or aspiring leader, this interview is packed with invaluable lessons.
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#BillionaireFiresideChat #LarryConnor #RealEstateInvesting #Entrepreneurship #Leadership #Innovation #FamilyOfficeClub #businesssuccess
Host: Great, welcome, Larry.
Larry Connor: Thank you.
Host: Appreciate you being here.
So, we did an interview virtually recently, and it went great—we appreciate that. Larry got started in 1991. He had a couple of partners and started 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 properties. He bought out his partners and created The Connor 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.
He’s one of the few people who has been both to outer space and the deep sea. And now, he’s been to a Family Office Super Summit. So, thanks for being here.
Larry Connor: Appreciate it, thank you.
Host: Yeah, what else would you add about your background? Maybe something about where you grew up, your family, or anything else that you think would be good for everyone to know before we get started on the questions.
Larry Connor: So, I was not a good student. I barely made it through high school. I lived in the stable high—I still do today, by the way. Plug for the Midwest, great area. I didn’t have to worry about touring campuses and colleges because my grades were so bad. But in the stable high, if you graduated from high school, there was one school—Ohio University—that had to take you. And literally, during 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.” And they were right. They had a 50% flunk-out rate in the first year.
I managed to get in there, stay in there, and turn things around. But if you asked me, “What was your background? Finance? Economics? Business?”—none of the above. I was an English major with a concentration in Shakespearean literature, which essentially qualifies me for nothing.
We've owned and separated eight different businesses—seven of them 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 Connor Group in 1991.
Host: Awesome. Yeah. Appreciate you sharing all that. That’s great—especially the part about being a bad student. You know, in childhood, the only grade you get on your value on planet Earth is basically, “What’s your grade in school?” Right? It was like school, sports, or Boy Scouts, etc. So, what was the turning point for massive increased momentum? Was there some moment when you started doing one thing or acquired one asset, and everything just took off?
Larry Connor: We believe that it’s a process. I think that process involved failure. When we started in ’91, my partners and I were not from the industry. We knew something about operating businesses, so we decided we weren’t going to pay attention to conventional systems, processes, norms, or beliefs—we would chart our own path. We did a lot of things right, but we also made a number of mistakes. We weren’t afraid to make mistakes—not reckless, but thoughtful. The difference was, from those failures, we owned them. We didn’t make any excuses. We learned from them, changed quickly, and just continued to get better and better. And that’s been a 32- or 33-year process.
In fact, today, it’s interesting—we did our first acquisitions in ’92, so this is our 32nd year. And in 2024, we have a mantra of “Change, Simplify, and Improve.” We have 90-plus different initiatives going on this year. Keep in mind our size—we’re about 440 associates. Some of these initiatives involve fixing mistakes we should have corrected five, six, or seven years ago, while others are new and innovative. We believe you have to reinvent yourself. If you want to be elite—if you want to be exceptional—you have to be different. Not just surface-level different, but disruptively different. For us, it's always a learning process.
Host: That’s awesome feedback. We meet a lot of people in this room each year, and if you’re saying the same thing as everyone else, I don’t know how you get a reply from anybody or get a partner engaged. That’s such good feedback for everyone here—investors and founders alike. What’s a million-dollar strategy that founders and investors here could take away from you today?
Larry Connor: I wouldn’t think about it in terms of a million dollars—that’s the hopeful outcome. I’d focus on the process. What I would do—and what we do—is take a hard look at results. We’re a real estate firm with about $5 billion in assets, but we also own a small boutique investment firm managing about $750 million—essentially just our money. We invest in public and private companies, and we have high expectations in everything we do.
So, if I were in your shoes, managing or creating wealth, I’d ask: “What results have I achieved historically? Are they what I want?” If you want to compound at 14% but are only compounding at 8%, you need to take a rigorous self-inventory. What are your beliefs, philosophies, and strategies? Why aren’t you hitting your targets? Then, I’d implement thoughtful, planful changes—probably in systems, processes, and analytics. If you have the right processes, the right people, and the right plan, the outcomes will generally take care of themselves.
Host: That makes sense. Back to your earlier comments about breaking the mold—I remember in our phone call, you mentioned how other people would hire a maintenance crew to handle six tickets a day, but you aimed for 20. Can you talk about how you break industry expectations and molds?
Larry Connor: We hire nobody from the industry. Not our site managers, sales teams, or service teams—nobody. Why? Because early on, we tried hiring industry veterans, and they either thought we were crazy or couldn’t change their habits and beliefs. So, we decided that wasn’t going to work.
By the way, this makes it much harder to find the right people, and we have to invest heavily in training—we spend millions on training every year. But if you want to be exceptional, you can’t be like everyone else. You have to be smart different.
For example, in the industry, maintenance workers typically handle six to ten service requests per day. Our technicians handle 20 to 25 per day. We measure this, ensure accountability, and invest in training, rewards, and recognition.
Host: That’s great. What’s a costly mistake you’ve learned the hard way that investors and founders here should avoid?
Larry Connor: We don’t have enough time! But here’s one: Hiring the wrong people. We believe 90% of your problems—and solutions—are people-related. The biggest mistake we see is when companies hire someone who lacks competency or commitment but hesitate to make a change. Identifying that problem early and taking action is crucial.
Host: Great insight. Lastly, do you want to talk about the culture book you’ve generously gifted everyone here?
Larry Connor: We believe culture is foundational. Any business is a team sport, not an individual one. Seven or eight years ago, someone suggested we create a book about our culture—not for publishing, but for our associates. We updated it a few years ago.
If you want to know who we are, read it. It’s a simple, 30-minute read. Culture isn’t just a mission statement on a wall—it’s lived through actions and decisions.