Retail Real Estate Investing Blog | RockStep Capital

The Monumental Way To Keep Real Estate Alive For Generations

Written by Andy Weiner | Jul 14, 2025 4:31:34 PM

If there’s one thing that’s made the biggest difference in my career, it’s mentorship. Not school, not luck, not timing. Mentorship.

Real estate is a relationship-driven business. Always has been. And when you’re just getting started, you don’t even know what you don’t know. Mentors help you see around corners, avoid the landmines, and make better decisions. Looking back, I can say without hesitation that the lessons I learned from my mentors were foundational, not just in deals, but in how I lead, think, and operate today.

Two Kinds Of Mentorship, Both Equally Important

Over the years, I’ve come to think of mentorship in two distinct ways: Mentoring individuals who work within the RockStep Capital team, and giving advice and guidance to individuals who are outside of our company. And I like to mentor people from both of these categories.

Internally, it’s about knowledge-sharing, building up our team, and making sure we don’t operate in silos. Collaboration is part of our DNA at RockStep, and mentorship plays a big role in that. On the other hand, when mentoring people, it’s about giving back and helping others navigate the industry, especially when they’re just starting out.

When it comes to mentorship external to RockStep, I tend to mentor people who need help with career guidance. I’m currently mentoring someone who graduated from college a couple of years ago and is trying to figure out how to proceed in real estate. 

For me, if someone’s curious and motivated, I’ll make the time.

Real Estate Isn't Easy To Understand, But Mentors Bridge That Gap

A lot of people still don’t fully grasp what the real estate industry includes. They hear "real estate" and immediately think about residential or brokerage. But commercial real estate is a wide and complex field, and is often something many people haven’t been exposed to.

That’s where mentorship becomes powerful. It helps demystify the business and gives people a real sense of what the career paths look like.

There are leasing, property management, finance, acquisitions, underwriting, construction management…I mean, these are just a handful of the different professions within the industry. And those are just within one sector. The number of paths you can take is significant, but only if someone shows you they exist and gives you practical advice on where to begin. 

If you’re new to the industry and trying to figure out where you belong, start by asking:

  • Do I want to work in retail, multifamily, office, or industrial real estate?
  • What roles appeal to me—leasing, asset management, acquisitions, development?
  • Who in my network is already doing this work, and how can I learn from them?

Those are questions mentorship can help answer much faster than trial and error.

The Mentors Who Helped Shape My Life And Career

I didn’t get here alone. The people who took the time to guide me early in my journey made all the difference.

One of my closest friends was instrumental when I transitioned from the family business into shopping center investments. He had been doing it for 12 years prior in his own company, and he agreed to mentor me and train me. So for the first six to eight years of my real estate career, he was very actively working with me. He provided guidance on how to structure an acquisition, how to structure a lease, how to work with the big retailers, and also how to learn about risk and risk mitigation.

Another major influence was my father. I worked with him from 1984 to 1997, for a total of 13 years, at the family-run business Weiner Stores. Through that, I learned a lot about business. Most notably, I was able to learn how retail works and how all the components of retail work together (store management, real estate, leasing, finance, logistics, systems, HR). That early exposure to the full picture of how a business runs helped shape how I lead today.

And then there was a controller who worked with the RockStep team for many years and was hands-down one of the most insightful people I’ve ever worked with. He had amazing judgment about risk, about people, about how to do things, and how to resolve problems. He was funny. He was great with people. He was an A+ expert in that, which is one of our most foundational RockSteps. I learned as much about human dynamics from him as I did about numbers.

Broader Lessons That Went Beyond Real Estate

Not all mentorship comes from real estate professionals. Some of the most profound lessons came from people whose backgrounds were entirely different.

One mentor, a PhD from India, taught me to think in systems. I learned a lot from him about life and how to deal with systems, as well as how to maximize efficiency. He helped manage logistics and supply chains and was one of the smartest, kindest people I’ve ever worked with. I even traveled to visit him and his family in Madurai, and that trip changed how I see the world.

Another mentor, a former district manager, helped me understand the deeper context of inequality and discrimination in America. He grew up in southern Louisiana during the time of the Jim Crow laws, and I learned a great deal from him about business, about people, and about integrity. He taught me to listen more closely and lead with empathy.

And one of my uncles gave me a geopolitical education like no other. I learned a lot about how politics works, how geopolitics works, how to deal with difficult people, and how the world at large works. These weren’t just life lessons. They were leadership lessons.

What Makes A Great Mentor?

I get asked this a lot, and the answer is simple. 

A great leader is somebody who's willing to speak straight, willing to take the time, and share the lessons learned. 

That’s it.

You don’t need to be a polished public speaker or have a fancy title. You just need to care, to be honest, and to show up consistently. That’s what made my mentors great. And that’s what I try to offer in return.

Mentorship As Succession Planning

There’s a practical side to all of this, too. Mentorship is how you build organizational strength. It’s how you prepare your company to grow beyond you.

At RockStep, everybody is responsible for succession planning in their own departments. As we grow (and we are growing now and about to grow even more), the importance of contributing to the formation and accomplishment of your department’s goals is massive.

I won’t be in my role forever. And the way I see it, if I haven’t trained people to take over, then I’ve failed as a leader. That applies to every department and every person in a leadership role. Mentorship isn’t optional; it’s essential.

Our Responsibility To The Real Estate Industry

This is bigger than RockStep. As industry veterans, we have a responsibility to open the door for the next generation.

We have an obligation to give back and to build more people in our industry. That’s why I mentor people who aren’t even part of our company. It’s why I support industry groups like ICSC that are trying to bring more young professionals into the field.

I have seen that overall, people just don’t understand the retail real estate industry. And if they can spend some time in it, they can get to like it and know how good of an industry it is.

What I Hope My Legacy Will Be 

I’ve done a lot of deals in my life. I’ve bought and sold more properties than I can count. But when it’s all said and done, that’s not what I want to be remembered for.

I would like to have my legacy at RockStep Capital to be that I mentored people both in the industry and within RockStep.

If people can look back and say I helped them grow, think more clearly, or find their path in this industry, then I’ll know I did something that mattered.