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Investing for the Long-Term: Lessons from 40 Years’ Experience in Real Estate

We have had guests from all over the real estate, business, and investing world here on The Executive REI Show. And they’ve taught us so much about the fundamentals of real estate, how to maximize investments, and advice for newcomers to this space.

Ken Holman
Ken Holman

But we recently had a special guest come on, someone who has a personal connection to the show: Ken Holman—my dad! He’s also the Founder and President of the Overland Group!
Ken has over 40 years of experience in the real estate investing world, from management to development to construction. He provides some hands-on advice that he learned from weathering several recessions and downturns, providing us with some lessons to take forward on the real estate journey.


Ken’s Journey

Ken and Michael have worked together with the Overland Group for about five years. But Ken’s journey in real estate investing started long before that. After graduating with an MBA, Ken started working at a small financial consultancy agency, specifically with the syndication real estate arm.

After five years there, he went out on his own to start in real estate management. From there, he went to law school—not to practice, but to gain a greater understand about the legal side of real estate. Ken also moved into development and construction, wanting to work with every section of the real estate pipeline.

Today, Ken is the founder, owner, and president of the Overland Group, which is a vertically integrated real estate company made up of Overland Advisors, Overland Capital, Overland Construction, and others. He also founded NAREA (National Association of Real Estate Advisors) to help and educate real estate agents improve their skills and qualifications.

Owning Multiple Companies

So, Ken is involved in a lot of companies. And some might ask: why? What is the benefit of owning an investment, development, and construction company?

For Ken, it’s simple: you must understand the whole pipeline of the real estate industry. Just think about the relationship between developers and construction—it can quite often be contentious. Even though they are working together, there are expectations on either side that are not met and can sour the relationship. So, knowing both sides of the experience can make you more effective and participate in higher-quality projects.

For those who want to take their business to the next level, consider building new verticals in your company. This can help you:

  • Increase understanding of all aspects of the business (management, development, construction, investing).
  • Improve your relationships between diverse types of professionals.
  • Create complimentary verticals that can help your business grow and expand.

While there are various aspects to real estate investing, it is a holistic practice. Ken shows us that it is beneficial to learn as much as you can about all aspects to find real estate investing success.

Lessons Through 40 Years of Experience

Few investors have been in the real estate game for so many years. In his 40+ years, Ken has seen a number of downturns and recessions. And, through each one, he came out the other side learning something and being able to grow and improve.

Two of the biggest changes in the industry over the last 40 years are:

  • Market conditions like inflation and interest rates. This is always shifting and moving, which means that real estate investors need to double down on the basics, find good deals, and understand the fundamentals of real estate to weather any storm.
  • Market availability. In the past it was easier to find something at a decent price, buy it and fix it up and then sell higher because of the value-add. Prices are higher now and these opportunities for a value-add model are more difficult. This means investors need to be creative and in-tune to new opportunities.

But despite all the changes over the years, Ken emphasizes one thing that makes all the difference: focusing on relationships. So many things about real estate has changed, but that is not. It is more important than ever to build solid relationships within the industry and expand your professional network to achieve better deals and open more opportunities.

Where Are We Heading?

Despite the historic and ongoing changes, the fundamentals of real estate stay the same. Ken’s perspective is that there is no better investment than real estate because of these key features:

  • You can safeguard your capital in real estate.
  • Real estate creates cashflow.
  • Investing in real estate provides you some level of control over your investments.

Given that real estate is such a worthwhile investment, Ken advises people to focus on the fundamentals. In every deal, make sure that you are not overleveraging yourself. Make sure you understand the basics and don’t take unnecessary risks. In doing this, investors can come out the other side of a recession with their investments safe.

Ken is concerned about the rising inflation and cost of materials of present day. However, this is nothing new: recessions and market dips happen. So, make sound decisions and stay the course through volatile market conditions.

Part of making sound decisions is choosing the right asset type. Ken favors mixed-use properties that combine residential and commercial spaces. He also shared an old saying, “invest in land—they aren’t making any more of it” as a foundation to his strategy to purchase and develop new land.


We could talk with Ken for hours about all his advice from 40+ years in real estate. But a lot of his advice boils down to something super simple: learn everything you can about real estate investing, prioritize relationships, and then focus on making sound deals with the fundamentals of real estate.

Make sure to check out Ken’s interview episode on the podcast HERE. And if you want to connect with him personally, feel free to send him an email at

Michael Holman

Michael Holman

Michael has extensive financial and operational experience. He is a licensed Certified Public Accountant and has a Masters of Accountancy from Brigham Young University. Before working at Overland Group, Michael worked at Ernst & Young on some of the largest real estate and technology companies in Utah.
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