Ep #1032 – Steve Rozenberg on Real Estate Investing: Key Takeaways
In this powerful episode, Steve Rozenberg shares his incredible journey from an international airline pilot to a successful real estate investor and property management entrepreneur. His story is a testament to resilience, grit, and the power of systems in business.
Steve’s Real Estate Journey: From Crisis to Opportunity
- After 9/11, Steve’s “safe” pilot career was abruptly disrupted, forcing him to rethink job security and income independence.
- He dove headfirst into real estate, learning everything from wholesaling to flipping, even paying a mentor $10,000 to master double escrow closes.
- By 2005, Steve purchased his first apartment complex, using profits from wholesaling as seed capital.
- He and his partner bought dozens of low-income single-family homes, quickly learning the hard lessons of tenant challenges, maintenance nightmares, and property management chaos.
The Game-Changer: Systematization and Customer Service
- Faced with overwhelming management issues, Steve built his own property management system with clear processes, checklists, and KPIs.
- A consultant’s insight revealed the real problem wasn’t customer service but lack of systematization—consistency is king.
- Implementing scalable systems allowed Steve’s company to grow on autopilot, managing nearly 100 properties and beyond.
- Outsourcing operations to virtual assistants in Mexico helped maintain efficiency and consistency while keeping costs down.
Mastering the Three Core Business Archetypes
- Steve breaks down business success into three pillars: monetization (marketing and sales), systems (processes and KPIs), and duplication (scaling beyond yourself).
- Marketing drives leads, sales convert them through multiple touchpoints, systems ensure consistent delivery, and duplication enables rapid growth.
- Measuring results and tracking KPIs is essential—if you’re not measuring, you’re guessing.
Leadership, Vision, and Mindset
- Clear vision fuels motivation: Steve’s goal is a $50 million company with 35% profit margins while working just five hours a week.
- Hiring the right people means matching personality profiles to roles and defining clear responsibilities and outcomes.
- Leadership is about inspiring trust and acting like the CEO you want to become—not the employee you once were.
- Coaches and mentors are vital; no one succeeds alone. Failure is a stepping stone, not a dead end.
Life Lessons Beyond Real Estate
- Steve shares a deeply personal story about losing his son and how it transformed his perspective on life and business.
- The ultimate goal is to create a life rich in memories, not just money. Time with family is irreplaceable.
- Transform pain into purpose—choose how you react to life’s challenges and build meaning in your journey.
Steve Rozenberg Bio
Steve Rozenberg is a dynamic professional whose expertise and unique insights make him a compelling guest. With a diverse background that spans multiple industries, Steve brings a fresh perspective and innovative approach to his work. Though specific details of his career path and achievements are not publicly available, his ability to engage and inspire audiences is evident. Steve’s participation in this episode promises to offer valuable viewpoints and thought-provoking discussions relevant to the event’s themes. Beyond his professional endeavors, Steve is known for his passion for continuous learning and personal growth, making him a relatable and inspiring figure for listeners.
You can support his foundation by donating at LiveLikeJett.org.
Here’s some of the topics we covered:
- How 9/11 Transformed Steve’s Life as an International Pilot
- How Buying Real Estate Before the 2008 Crash Turned into a Rollercoaster Ride
- The Secret Weapon Every Business Needs to Explode Growth
- The Game-Changing Strategy You’re Not Using
- The Hidden Classes of Customers and How to Maximize Each One
- Why a Crystal-Clear Vision Is the Fastest Way to Crush Your Business Goals
- The 3 Must-Know Business Archetypes That Will Define Your Success
To find out more about partnering or investing in a multifamily deal: Text Partner to 72345 or email Partner@RodKhleif.com
Full Podcast Transcript: Ep #1032 – Steve Rozenberg on Real Estate Investing
Interview Conversation
Rod Khleif: Welcome back to Life Time Cash Flow through Real Estate Investing. I’m Rod Khleif and I am absolutely thrilled you’re here. And I’m really looking forward to this interview with my friend Steve Rozenberg. So Steve is a former international commercial airline pilot, maybe currently. Are you currently still a pilot? You know, he’s done a couple thousand doors, single family, multifamily, done all kinds of amazing stuff, owned a very large property management company that he sold to a much larger company.
Rod Khleif: And, you know, I met him was that I am in.
Steve Rozenberg: No thinking.
Rod Khleif: Venkman. Okay. You know, I.
Steve Rozenberg: Think John and Charlotte.
Rod Khleif: Oh, yeah, yeah, yeah, yeah, yeah, yeah, yeah, yeah. Okay. That’s right. The Charlotte event. Yeah, yeah, yeah. Okay. And, you know, we hit it off, and I’m like, Dude, I got to get you on my show. So here we are, man.
Steve Rozenberg: Here we are. Thanks for having.
Rod Khleif: Me. Good to have you here, brother. So. Well, listen, I just completely screwed up that bio, so why don’t you just tell us who you are in your own words? Give us a rundown on who Steve is and why real estate became part of your journey.
Steve Rozenberg: Well, you know, I never thought I would be in real estate, right? I’m one of those second-generation type people that this was never my dream. I never thought I’d be here doing something like this because my only dream or passion growing up as a little kid was to be a pilot. I worked hard. I had that hard work ethic instilled in me by my parents.
Steve Rozenberg: I did everything I could, and at 25 years old, I was the second youngest person hired by this particular airline—the best job in the world. I was flying all over the globe, enjoying a safe, secure job with a pension and retirement. I was done. Everyone said, “Man, you’re done. You’re set until the end of time.” And then one day, history changed.
Steve Rozenberg: That day was 9/11. 9/11 hit—an event so tragic. For me, it happened two days after 9/11 because that was the day I got my furlough notice from the airlines. It made me realize that the safe, secure job I thought I had was suddenly in jeopardy.
Steve Rozenberg: Suddenly, I was looking at the possibility of being on the street along with 50,000 other pilots. Shock and awe hardly begin to describe it. I thought to myself, “I didn’t do anything to cause this, but now I’m a victim.” And I realized that this wasn’t some isolated industry issue; everything was changing within a matter of days.
Rod Khleif: They don’t waste any time. No—I have to interrupt for a second because I got to share a story about my dad. My dad worked for Continental for 36 years. Continental Airlines—we used to put our hands over our hearts when the bird flu came around because of their gold tail. He worked there for 36 years and even got laid off.
Steve Rozenberg: With the golden tail bird.
Rod Khleif: With the brass, as we used to say. But, he was let go after 36 years. So, what is job security? Your job security is in your head—it’s an illusion.
Steve Rozenberg: That’s exactly it. I decided then that I wouldn’t be a victim. I needed a way to generate income on my own terms. I didn’t know anything about real estate because my whole life was about being a pilot. Suddenly, I was a fish out of water, looking for any kind of water to swim in—and that led me to real estate.
Steve Rozenberg: I immersed myself completely: reading a book a week on real estate (this was in 2001, before YouTube and Facebook; we had libraries, remember?) I took classes, attended weekend events, and even paid a mentor $10,000 to learn double escrow closes and wholesaling—even though I wasn’t even sure what wholesaling meant at the time.
Rod Khleif: Wholesaling.
Steve Rozenberg: Wholesaling indeed. I handed over the money, and 30 days later, there I was sitting at a closing table with a buyer, a seller, and a mentor explaining double escrow closes. I walked out with a check for $20,000, of which 50% went to my mentor. I was stunned—“Can we do that again?” I asked. And he said, “See if you can keep taking it across the finish line.”
Steve Rozenberg: From that point on, I dove deeper into the various types of real estate transactions—options, flips, wholesaling—and eventually I purchased my first apartment complex using money earned from wholesaling.
Rod Khleif: When was this, exactly? Give me a timeline.
Steve Rozenberg: That was in 2005. From 2000 to 2005, we owned the property. Then a church next door bought the property cash because they wanted a parking lot. By mid-2007, as banks started to fail, the church’s cash deal came through, leaving us with a hefty sum.
Rod Khleif: Oh, that’s good timing.
Steve Rozenberg: With that money, my business partner and I decided to buy single-family houses—they were cheap. We thought, “Why not buy a bunch of them instead of flipping?” We even went after low-income properties that promised 55–60% cash-on-cash returns.
Rod Khleif: For those listening, I’m shaking my head because I know where this is going—trust me, I’ve been there.
Steve Rozenberg: Within six to nine months, we had amassed about 25 properties in Houston, buying up the “crappy” properties that everyone else shunned. And then reality hit—tenants, maintenance issues, nonpayment, even drugs and worse. We learned quickly why these properties were avoided in the first place.
Steve Rozenberg: Instead of running away, we doubled down. We acquired more properties—and soon found ourselves managing a nightmare portfolio with 40 to 50 properties. My wife warned me, “Steve, if you buy another one, it better be nice because you’ll end up living in it,” because clearly, I needed to fix my approach.
Rod Khleif: I can relate—I’ve been there.
Steve Rozenberg: Realizing our limitations, we stepped back. Our average tenancy was eight months while maintenance costs were triple because tenants would even take wiring as “parting gifts.” Neighbors would sometimes take our plants and replant them in their yards, claiming they were theirs! It was chaos.
Steve Rozenberg: When we tried handing over our dumpster fire of a portfolio to outside management companies, no one wanted them. That forced us to create our own management system—with processes, structures, and a business-like approach. And soon, people began coming to us, asking if we could manage their properties.
Rod Khleif: Right? You ended up managing not only your own portfolio, but others’ as well.
Steve Rozenberg: Initially, I thought, “No way—I don’t want your problems; I haven’t straightened out mine yet.” But then, in Houston around 2011, everything changed. Though we were unlicensed and doing things the “wrong” way, property owners started handing us their properties, and soon we were managing nearly 100 properties.
Rod Khleif: Suddenly, you’re managing single-family homes left and right.
Steve Rozenberg: We even took on a 52-unit complex in one of the roughest areas—so rough that a show like “Drugs Inc.” was filmed there. We got free rent because we had no money, but it worked.
Steve Rozenberg: As our business grew, so did the challenges. I worked 60–80 hours a week, fielding constant complaints, stress, and burnout. In property management, unlike other industries, no one ever “calls you in” happily—you’re the trash man, always on duty.
Steve Rozenberg: Then it hit me: there was a scalable business here if we could improve customer service. We hired a consultant to help us bridge the gap between what sales promised and what operations delivered. After detailing every step of our process with notes, diagrams, and even caricatures, he told us, “You don’t have a customer service problem—you have a systematization problem. Until you can deliver the same product consistently, your business will never truly succeed.”
Rod Khleif: How close were you before that realization?
Steve Rozenberg: Far off. We were so disorganized that our senior manager, my business partner, and I were all working on wildly different versions of the same process.
Steve Rozenberg: That day, the light bulb went off. Once we put the right systems in place—with checklists, flow charts, and proper KPIs—everything started to click and our company scaled on autopilot.
Rod Khleif: By the way, in property management, no owner or tenant ever calls you with compliments. Burnout is real—I’ve seen managers crumble under the stress.
Steve Rozenberg: True. But needing a business means overcoming those challenges. We realized our next step was to implement even better customer service—hire the right people, use technology, and automate wherever possible.
Steve Rozenberg: I started working with virtual assistants in Mexico—60% of my company’s operations were outsourced there because they understood our processes and operated in the same time zone. That was key to duplicating our success.
Rod Khleif: I use VAs from Mexico as well—they’re fantastic and often a better fit than those from other regions.
Steve Rozenberg: As the business scaled, questions arose about my role. Am I the pilot building my company or merely managing it? Soon, invitations to speak in places like Australia confirmed that the processes we developed worked not just in real estate but in any business where systems and procedures are paramount.
Rod Khleif: And you often say that if you can’t walk away from your business for a set period and have it run better in your absence, then it’s not truly a business—it’s just a job.
Steve Rozenberg: Exactly. I recall a mentor once telling me, “If you can’t take three days, weeks, or months away from your business and it grows, you’re too involved.” That’s why systematization is everything. Otherwise, you’re just running yourself into the ground.
Rod Khleif: And this applies not only to property management, but to any business—from real estate syndications to investor relations. We even surveyed our investors and students for what kept them up at night, and their responses became marketing gold.
Steve Rozenberg: In every business, there are three core areas: monetization (marketing and sales), systems (the checklists, flow charts, and KPIs that make everything replicable), and duplication (scaling the model beyond yourself). Mastering these three is key.
Rod Khleif: As Peter Drucker said, “Every business is nothing but marketing and innovation.” It’s all about getting the right person, message, and system in place.
Steve Rozenberg: That’s right. Marketing gets the phone ringing, and a detailed sales process—with an average of 22 touchpoints before a close—converts leads, while systems ensure consistency and automation. Finally, duplication allows you to scale rapidly, whether by expanding to another city or simply multiplying your operational model.
Rod Khleif: And don’t forget measuring results. If you’re not tracking your KPIs, you’ll never know what needs improvement.
Steve Rozenberg: Absolutely. In any field—sports, business, or aviation—success depends on choices, systems, and constant learning. For example, every time we fly, we rely on checklists to manage tasks in critical moments. I applied that mindset to my business and learned never to overlook the basics.
Rod Khleif: Speaking of checklists, you even shared how you overhauled a 19-page process into a simple, one-page checklist for client handoffs, linking to more detailed instructions only when necessary.
Steve Rozenberg: Exactly. Keeping it simple and ensuring every task is done seamlessly with minimal human error is paramount. And that’s where technology and outsourcing come into play.
Rod Khleif: On the topic of outsourcing, tell us about hiring virtual assistants. How do you ensure you get the right person?
Steve Rozenberg: I always start with a clear organizational chart—one that shows where you are now and where you want to be in the future. Every role must have a detailed job description, a list of responsibilities, KPIs, and even a risk profile. For instance, when hiring for a role, I use disc profiling to ensure the candidate’s personality fits the job requirements. I even tailor the job ad specifically to attract the right disk profile.
Rod Khleif: That’s brilliant—making sure you don’t force a round peg into a square hole. And I add that it’s important to identify the ultimate outcome for a role, so candidates know exactly what they’re signing up for.
Steve Rozenberg: Absolutely. Beyond just hiring, leadership is crucial. As a leader, you must inspire trust and have a clear vision. For me, that vision might be, “By June 1, 2029, I’ll have a $50 million company with 35% profit margins, while working just five hours a week.” That clarity not only motivates your team but creates an environment where everyone knows where the business is headed.
Rod Khleif: And as you always say, if you want to be the $50 million CEO, you must act, speak, and walk like one—not like a $50,000 employee.
Steve Rozenberg: Exactly. There’s a huge difference between the entrepreneur, the leader, and the innovator—the artist. Each role is essential, and no one can succeed entirely on their own.
Rod Khleif: Look at the greats in every field—they all have coaches, mentors, and partners to push them forward. I have several coaches myself, and that support system is invaluable.
Steve Rozenberg: I agree. Successful people never say they did it all by themselves. We fail, we learn, and we have coaches to help us turn failure into a learning experience.
Rod Khleif: Don’t fear failure, folks—fear regret. It’s far worse to look back a year or two from now and realize you missed out on making memories with your loved ones.
Steve Rozenberg: I’ve learned that lesson the hard way. I lost my son six months ago. He was only 19, a free spirit who lived life to the fullest—from riding motorcycles together to traveling the world. He taught me that memories are free, and no amount of money can replace the moments you share with your family.
Rod Khleif: I can’t imagine. It’s unfathomable. But the fact that you’re channeling that grief into your foundation, LiveLikeJett, to help kids pursue trade school is incredibly powerful.
Steve Rozenberg: Thank you. I truly believe that no matter how hard life gets, we have a choice—to let it define us or to transform our pain into purpose. I want people to know that while we can’t control what happens to us, we can always decide how we react.
Rod Khleif: Life is about meaning. We choose the meaning we place on our experiences—and as entrepreneurs, it’s imperative we create a life filled with memories, not just money.
Steve Rozenberg: Exactly. I may have chosen this challenging path, but if I can inspire someone to take time for their family, to create memories, then I’ve done my job.
Rod Khleif: For those listening who are grinding away at a 9-to-5 and have children, please take note. There’s no substitute for the time you spend with loved ones.
Steve Rozenberg: And if you want to know more, you can always reach out to me via my website at steverozenbergrosieandbtrjet.com or on Instagram. I’m always happy to help, answer questions, and share what I’ve learned along the way.
Rod Khleif: I really appreciate you coming on today, Steve. This conversation has been incredibly valuable—for both me and for everyone listening. We have to break bread together soon, brother.
Steve Rozenberg: I’d love that, Rod. We’re clearly on the same wavelength, and together, we can help change lives.
Rod Khleif: Agreed. Until next time, live like jet, dawg!
