Starting Over in Real Estate: What Would I Do Differently?

I am no longer in my twenties, in fact, I am now in my forties! Real estate has been wonderful to me and I am very fortunate but that does not mean I did everything the right way. I have no regrets and everything I have done made me who I am today, but there are some things I would do differently knowing what I know now. I started as a real estate agent, helped my dad flip houses, then became an REO agent, bought rentals, took over everything, and ramped up the flipping business. Then I started an online business, YouTube, social media, etc. It has been a ton of fun and real estate has allowed me to pursue many of my dreams like owning multiple exotic cars. If I were to start it all over again there are some things I could do that would have sped up the process!

What was my attitude like when I was in my early 20s?

When I was 22, I was interested in having fun and I assumed I would find a way to make a lot of money. The problem was I never made a plan or thought about exactly how I would do it. I thought I would stumble upon some awesome idea or something would magically happen. For some reason, that magic never happened!

I was also afraid to set goals when I was younger. In the back of my mind, I thought if I set goals then I might not reach them. I didn’t want to be a failure and not reach those goals, so I took the easy way out and did not create any goals. I told myself that I didn’t need goals, because I could succeed without them, and all those people saying you have to have goals to succeed don’t know what they are talking about. In fact, it was me that had no idea what I was talking about and I was making excuses. In 2007 I started unknowingly making goals for my real estate business. I got tired of doing “okay”. I wanted to do much better than okay.

After I started thinking about how many deals I needed to sell to make the money I wanted to make I became frustrated because it seemed like such a huge number. I needed to sell 100 houses a year to make really good money in real estate! (This was in the early 2000s and prices were much lower than they are today in my area.) I could never do that, that was ridiculous! I wrote out a letter explaining how unfair the world was being and ironically I created a plan that I was not even planning on making.

Was I investing in real estate in my early 20s?

When I was 23 I bought a house, but I didn’t think a lot about the process. I knew buying a house was supposed to be a good investment and I wanted to buy the coolest house within my budget. I was not married, I did not have a lot of expenses, and I ended up buying a $190,000 house. The house was not that great of a deal, because the real estate market was very strong and there were few foreclosures (I also was not aware of the many other ways to get deals back then). I always made my payments on that house until the day I sold it 7 years after I bought it. I also put about $10,000 of work into the house (plus sweat equity) to update it and keep up on maintenance. I ended up selling the house for less than I bought it for thanks to a declining market and paying top dollar for the house when I bought it. That was not a very good investment!

I am not mad I bought the house as it did teach me a lot and I loved that house! I was also not paying rent. While I sold it for less than I bought it for, I paid down the principal and it was worth it to me. Looking back on that house now, I could have done so much better picking a house, and with my overall real estate strategy. I was not buying rentals either, which I wish I would have done much sooner.

How did I learn to set goals?

A short while after I wrote out how many deals I would have to do to reach my monetary goals, a BPO (broker price opinion) company asked if I could do a BPO for them. I had no idea what a BPO was, but I researched it and I agreed. A BPO is a valuation performed by a real estate agent that typically gives a value to a bank for a distressed property, refinance, or to remove mortgage insurance. After doing the BPO I did more research and found that BPOs can lead to REO listings and being an REO listing agent seemed like the career I wanted in real estate.  REO agents don’t deal with typical buyers and sellers, they deal with banks and the good REO agents sell a lot of houses. Fast forward a couple of years, and I was selling well over 100 houses a year, completing almost 1,000 BPOs a year and I was able to save enough money to start investing in rental properties.

It may seem random that someone called me out of the blue to complete a BPO and that lead to my REO career. However, after seeing how many houses I had to sell to reach my financial goals, I started thinking about how I could sell that many houses. I started looking into different marketing techniques, I started researching different facets of real estate. Instead of letting things happen, I started to make them happen and when that BPO opportunity came along I jumped on it. In the past, I may have told the company “sorry I don’t do BPOs” and never thought about it again.

I was 27 or 28 when this happened. If I had been setting goals and working hard on myself at an earlier age I know I would have been making much more money and be much happier with my career and myself at a much younger age.

How I would buy real estate and invest differently if I was 22

When I buy houses now, I always buy houses below market value. I buy foreclosures, short sales, estate sales, or regular sales that are cheap for one reason or another. The second house I bought was a foreclosure and I ended up selling it three years later and making almost $100,000 profit. I also started to invest in rental properties after I bought my second house, which I should have done much sooner. I bought my first rental at about the age of 30 and I own 182k square feet of rentals now, but I would have been so much better off buying rentals sooner. As the saying goes:

Don’t wait to buy real estate, buy real estate and wait!

Rental properties

If I were 22 again, I would use a completely different strategy than I do now to buy rental properties. For most investors, it takes at least 20% down to purchase an investment property and that makes it tough to buy rental properties. If you can buy a rental property as an owner-occupant, to begin with, and then rent the home out after a year, you can buy an investment property with much less money. If I could do it all over again, I would buy a house that would make a great rental and was a great deal at the same time. I would live in the house for a year and fix it up while I lived there. After the one year was up (most banks require an owner occupant to live in a house for at least a year), I would rent out the house. I would then buy another house that would be a great rental and repeat the process over and over. With no wife or kids, it is not too difficult to buy houses frequently and move every year. Now that I have a wife and three kids this would be a very unpleasant experience.

My book, Buying into Success, goes over this exact process.

Flipping houses

I was involved in flipping with my dad when I was younger but not as involved as I could have been. I was helping paint houses, and do minor repairs. I mowed the yards, checked on them, and once in a while helped with the numbers. I was not figuring out how to find better deals or any of the tougher side of the business. Later on, I was able to improve our business by learning these things and looking for more opportunities to expand. I wish I would have been more proactive at a younger age!

I also could have implemented the live-in flip. That is where you buy a house, live in it for 2 years, and then sell, hopefully for a profit. If you make money the profit is usually tax-free thanks to IRS tax rules. When I was going through the great recession and housing crash I could have been buying live-in flips if the rentals seemed too risky or the numbers were not working well.


I also did not read much or learn much about real estate outside of what I learned in the business. I learned a lot in the business but I was not creating my own strategy. I should have been reading, researching, and learning as much as possible about real estate investing. I did this in my late 20s, but not early on.

I was born to be an entrepreneur

I loved real estate because I never had a real boss or schedule. I was born to be an entrepreneur:

  • I never liked people telling me what to do, so I do not get along with bosses very well.
  • I don’t like working a regular schedule. I love to mix things up and do different things.
  • I like having control of my work and what is going on in my life.
  • I can’t stand when I see people do things the wrong way and I cannot fix it.

When I started out in real estate, I was not much of an entrepreneur. I followed my father’s footsteps and did what he did to make money in real estate. It worked out okay, but I did not have control of the business and I was not creating anything. It took me a long time, but I took over the business and bought out my father in 2013.  After taking over, I took another huge step in my real estate career. Having complete control is an awesome thing and my business has taken off.

I started a blog, a YouTube channel, I wrote books, I created social media accounts, and even coaching products. I have created multiple businesses and I should have been doing that from the very beginning. If I did not like my situation or wanted to change how things were done, I should have gone out on my own and made those changes happen. I think having my dad helped me a ton and he taught me a ton, but he was also a safety net of sorts as well. If I had gone out on my own much sooner I think I would have been more successful much sooner as well.

Many people wonder how I can handle so many things at once, but the great thing about being an entrepreneur is you don’t do it all yourself. Once you build a foundation and start having success, you can hire people to help with the business. The bigger team you have, the less work you have to do yourself and the more time you can spend with your family, while still making a great living. If I was 22 again, I would start on my own and create my business as soon as possible.

Find your passion

I was not passionate about selling houses as a real estate agent to regular buyers and sellers. I love houses, I love cars, I love sports, but being a regular agent was not something I loved. I think that showed in how much effort I put into it. When I discovered what I loved to do: flip houses, get great deals, create content, start businesses, my career took off! Finding your passion makes work not work. It makes it fun and something you want to do. I wish I would have spent more time finding my passion at a younger age.

If you are curious if real estate is for you, I created a quick and easy course to teach you all about the different types of real estate and what is involved in each of them.

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There are many things I would do differently if I was 22 again, but I can’t go back in time and I am perfectly happy where I am now. I continue to build a business, look for new opportunities, have as much fun as possible, and spend as much time with my family as I can. If you are 22, 32, 42, 52, 62, 72, or older you will get as much out of life as you are willing to put into it. You don’t have to be young to create a business, start making goals or start living the life you always wanted. If you don’t ever plan or set those goals, it will be very tough to live the life you want.

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11 thoughts on “Starting Over in Real Estate: What Would I Do Differently?”

  1. Hi Mark, thanks for all of the info. To take advantage of the owner occupied strategy don’t you have to have W-2 income? If you are a realtor ( as I am) how can I show steady income in which to get an owner occupied loan on a home?

  2. Love this post! It’s funny, I was actually thinking about asking you this exact question a couple days ago- I’m 19 so my real estate journey is just beginning but I’ve been eager to get started for a few years now. I (and I’m sure many others) love that you are so transparent and don’t just try to sell a $500 course in every post!! Keep it up 👍🏼

  3. Thanks for this article Mark! Would you also start an LLC to invest in multifamily early in, or buy in your own name?


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