After 30 Years of Real Estate Investing, THIS is What I Would Do Differently

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A younger person recently asked me, “After 30 years of real estate investing, what would you do differently?”

It’s a pretty good question, and it really made me think. At first, I was thinking like Frank Sinatra that I wouldn’t change a thing because “I did it my way.”

I quickly woke up and realized that’s nonsense; there are plenty of things I would have done differently. So, here goes.

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I Regret Not Starting My Real Estate Business Earlier

When I first started out, I thought I needed to work several jobs and save my own money to do my real estate deals, and I was only focused on buy and hold properties.

What I didn’t realize at the time was that this was a get-rich-slow strategy. I had been too busy making other people rich — everyone from builders and developers to apartment owners and real estate brokers. At the time, I was still a painting contractor and a real estate agent.

One of my biggest regrets is that I waited so long to quit my day job (although I do still keep my real estate license) and go into real estate investing full-time. I would’ve started my “I buy houses” business much earlier. I would’ve done more wholesaling and flips. And I would’ve utilized hard money for my deals earlier on in my investing career.

Related: Why I Don’t Regret Saying “Yes” to Opportunity & Quitting My 9-5 (Despite Challenges)

I Regret Not Delegating Tasks Sooner

Besides saving my own money, I tried to do just about everything else myself, including finding the deal, fixing the property, being the real estate agent, being the property manager, being the bookkeeper, and so on and so forth.

I micromanaged everything, instead of focusing on what I was good at, what I was passionate about, and what I could make money on (you know, the real economic drivers that pertained to me).

I can’t tell you how many times I was cleaning out a house or standing in line at Home Depot asking myself, why am I doing this?

It was a big hurdle for me to hire someone to do something that I knew I could do or something that I had done in the past. In my mind, no one could do it as well for as cheaply as I could myself. It took me a while to realize that you don’t have to do everything perfectly; you just have to do it good enough. I know now how ridiculous I was, and looking back, it was a big mistake not to delegate more.

If I focused on taking action to replace myself, I could have spent that extra time networking more, marketing more, and building my money list (which is just as important as a buyers list).

Today, I have a property manager in place, and I don’t do any maintenance at all. It’s the best decision I’ve ever made! It just took a while for me to concentrate on where I really made my money — finding deals — instead of on the little ways to save money by trying to do everything myself.

I Regret Not Using Leverage in a Bigger Way

Besides taking too long to find a mentor or coach and doing everything myself, the next big regret I have was not using OPM (Other People’s Money) and self-directed IRA accounts sooner and in a bigger way.

Sometimes, I think we’re afraid of success, especially if it means we have to take on debt. Maybe we’re even fearful of growth because we don’t know if we’ll be able to keep it going, and we think of all the “what ifs.” That was the case for me, at least.

I absolutely could have used more leverage, whether that was with private money starting out or with private placements later on.

When it comes to using leverage, though, one of the biggest considerations is do you have enough deals to keep the money at play?

Basically, there are three pillars to operating a successful investment or business venture: capital, scalability, and product. Oftentimes, there is a constant battle among these for balance. You’ll go through phases when you have more money than deals or not enough money when the deals are everywhere.

By the time I was 40, I had started buying bank-owned properties, and then eventually, I began buying notes. It took me way too long to figure out that a lot of good deals come from the banks, but I had learned about the opportunity as a real estate agent selling those deals to other investors.

Related: Here’s the Biggest Mistake I Made Starting Out in Real Estate: What’s Yours?

When I started buying notes from the banks, I realized that they had more deals than I had money, and I started to become less and less concerned with deal flow. I wish I had learned about buying bank-owned properties and notes earlier, as the availability of deals would’ve enabled me to leverage more money.

This all being said, raising capital was one of the best skills I ever learned. This became more and more evident after I started using private placements to raise capital for commercial real estate and later on for notes. If you take care of your investors and you do things right, you’ll have the use of their capital for years and years to come.

So, let me ask some of the more experienced folks on BP: What would you have done differently with your real estate investing?

Let me know with a comment!

About Author

Dave Van Horn

Dave Van Horn is President at PPR The Note Co. - an operating entity that manages several funds that buy/sell/hold residential mortgages, both performing and delinquent. Dave has been in the Real Estate business for 25 years, starting out as a Realtor and contractor and moving onto everything from fix and flips to Raising Private Money.

35 Comments

  1. Catrina Brooks on

    Dave, thanks for that post. It was very helpful. I would like to begin investing in notes. Where can I receive the most accurate and thorough education in your opinion?

    • Dave Van Horn

      Catrina,

      I think the answer to your question depends on the type of note investing you wish to pursue, your time commitment, as well as what you’re willing to spend on education. Are you looking to invest in residential or commercial notes? Institutional notes or private? 1st or 2nds? Do you want to be a passive investor or an active investor?

      And in terms of education are you looking for free information, to buy a book, a course, or an in-depth mentoring program? The answer could mean the price ranges from $0 to $50K. And also what is your time commitment for study as well as working in the business?

      No matter the answer, for starters you can check out the note forums here on BP, they’re a great resource for getting started. And more specifically, if you’re looking to learn about the institutional space (with 1st or 2nd residential mortgages) I have a free e-book that I can send you on the subject if you DM me.

      Hope this helps.

      Best,
      Dave

  2. cheryl c.

    Nice article Dave! I wish that I had scaled to apts and commercial years ago. I can add a few costly mistakes over my 30yrs:

    Failure to conduct proper background checks on tenants.

    Failure to properly vet contractors.

    Over-improving rentals and replacing things too soon (I like nice things – but my rentals don’t need them!).

    ok, I said it…now if I could only forget it!

    • Dave Van Horn

      Hi Cheryl,

      Great points! I made the same mistakes, luckily I was fortunate enough to come from a contracting and property management background that helped me learn some of these things early on in the process. Knowing the solutions to many of these problems can only be gained through experience.

      Glad to see you’re over that hump!

      Best,
      Dave

  3. Curt Smith

    Catrina, I’m not tossing water on your quest, a quest for knowledge is worth it regardless of the outcome. I have much more knowledge than I plan on applying.

    My point is to mention that post Dodd Frank buying non performing notes has gotten insanely complicated. Foreclosing/ deed in lieu has not changed, but the main tactic for the NPN note invester usually is to bring the note back to performing, this is where Dodd frank comes into play. I suggest you study under someone in your area who is buying notes to study under. Non performing or even performing notes is no longer a solo sport.

    • Dave Van Horn

      Hi Curt,

      It’s true – any business can become more complicated with more regulation, but with that being said, it’s important to mention that working NPN’s isn’t the only aspect to the note industry. For example, if one wishes to own NPN’s and avoid issues that could arise from Dodd-Frank, they could simply place non-performing notes with a licensed servicer or they could simply deal with performing notes, that could also be placed with a said servicer.

      I also want to point out that there is much more to the industry than just Non-perfomring and performing institutional notes. There are a lot of great opportunities out there for those of all experience levels (Lending Club being a great low cost example). Not knowing Catrina’s preference, I don’t want to discourage anyone from the extremely vast world of note investing.

      Best,
      Dave

  4. Dawn Anastasi

    I think getting private funds is one of the most complicated things in real estate investing. And yet, having to use just your own funds is very limiting. I think I could have done double the deals I have already done if I wasn’t limited to not using private money.

    • Dave Van Horn

      Hi Dawn,

      I agree. A friend of mine has an older brother who is extremely successful in the world of real estate, and he asked me when I started out, “How many deals could you do if the money was free? If you had an unlimited source of capital?” At the time I didn’t have an answer but looking back I realized how many deals I was essentially turning away because of money.

      When I was Realtor, working specifically for investors, I realized the discrepancy. I was selling around 75 properties a year to investor friends and buying around 5 to 10 properties a year for my own portfolio. That’s when I realized my number, without a team, that I could reach with unlimited capital. It was definitely one of the biggest “ah-ha” moments for me, which is a big reason why I chose to share it here on BP.

      Best,
      Dave

  5. Logan A.

    Dave, I know everybody’s situation is different, but generally-speaking, would you recommend investing in notes to a 27-year-old with only $50k in his Roth? I’ve been out of stocks in my Roth for about a year and am trying to figure out what to do with it. It doesn’t seem like I have enough in there to really do anything with decent yields. Any advice is welcome. Thanks.

    • Dave Van Horn

      Hi Logan,

      You’re never too young to start buying notes! In your case, you have a couple options:

      1.) You could afford a few performing 2nd notes or a performing 1st for under $50K. (Of course this option requires some education, so if you DM me I could send you a copy of our Performing Note Guide)
      2.) You could lend this $50K to other Real Estate Investors (that you either meet locally or here on BP) and create notes for them to do their rehabs that are secured to the property they’re renovating.
      3.) You could also buy unsecured notes (for as little as $25/each) on LendingClub.com. I personally average over a 10% return and I’ve found it to be relatively safe. Especially because you can spread out your risk buying a piece of multiple low cost notes from people with high credit scores.

      Best,
      Dave

  6. Jerry W.

    Dave, an excellent article as usual. I appreciate you sharing your knowledge with us. I would love to get into note investing but have very little available cash. I have bought into 2 notes from people I know personally. I do have one question. Can you just walk into a bank and buy notes from them? Without going through a broker or finding private lenders where do you find and buy notes at?

    • Dave Van Horn

      Hi Jerry,

      I’ve heard of people directly contacting banks outright, but I’ve never done it. At our level we now deal directly with large banks and their trade desks, but for a beginner I would recommend either buying from a broker, loan exchange/servicer/fund, or from other investors (which can be done online or in person).

      Reliable brokers and individual note investors can be tough to find, but you could start at local REIA meetings or online (LinkedIn is a great resource for this – I run a group called Distressed 2nd Mortgages Group that you’re welcome to join). Loan exchanges/servicers/funds can also be found online and don’t always require a personal connection, FCI Exchange is one example.

      Hope this helps.

      Best,
      Dave

    • Dave Van Horn

      Hi Jacob,

      That’s a good question. I learned the business through other REO agent colleagues and friends of mine, so I’ve never read one.

      I’m sure there are some reputable books out there. This would be a great question to pose to the BP forums.

      Best,
      Dave

  7. Jim Arnett

    So Dave, as a note investor I have been using my IRA LLC for the past several years. I have always wanted to consider private money. But the few hard money lenders I know want 10 to 20 % interest. Are there much lower interest rates available out there?

    • Dave Van Horn

      Hi Jim,

      Sure there is, the trick is to educate potential investors who aren’t traditional Hard Money Lenders. There are plenty of people out there who are happy making 6 to 8%.

      And the Hard Money is only such a high rate because it’s usually lent as short term money. And it’s important to remember it might be 10 to 20% the first time around but that rate can usually be negotiated down over time especially the longer you have a profitable relationship with that lender.

      Best,
      Dave

  8. Marcia Maynard

    Thank you for sharing your experience. After 20 years, I’m asking the same question. Our goals are different than yours, and my husband and I love our careers outside of real estate, but it does make it more difficult to do well in real estate when less focused on it.

    I would do these things differently:
    1. Seek OPK (Other People’s Knowledge) sooner.
    2. Get serious about investing in real estate sooner.
    2. Let go of wrong assumptions.
    3. Learn more about the possibilities.
    4. Be wary of the naysayers.
    5. Surround myself with positive people, doing positive things with their lives, for the right reasons.
    6. Trust in God, trust in myself, and trust in my husband more (my life and business partner).
    7. Create a strong team and delegate more.
    8. Review and reflect more often.

    • Dave Van Horn

      Great points Marcia! A lot of these were big ones for me as well. I think it all starts with one’s philosophy. Having a more positive outlook and an ability to listen to/learn from others (as well as yourself in terms of reflection) definitely shapes that.

      The one thing I’d add is the importance of a mentor. Even before finding someone in person, it’s important to study others who are successful and influential in your business. To this day I still listen to Jim Rohn, who was someone I admired greatly when starting out and shaped my philosophy.

      Best,
      Dave

      • Marcia Maynard

        I agree, mentorship in all aspects of our lives can be beneficial. Our local rental association has a mentor program. When I joined I was assigned a mentor and later I chose an additional mentor from the group, because I saw the benefit of having more than one mentor. There is a benefit to learning from people with different perspectives. Over the years, as I became more experienced as a landlord, I became a mentor to others who joined the association. Ten people have been matched up with me as their mentor. I reached out to all ten, but only two call me for help, guidance and/or a sharing of ideas. It has been mutually beneficial, as I learn from them as well! The mentor need not be local. Bigger Pocket members have become mentors to me as well… and I to others. It’s important to identify one’s goals and needs, reach out to others, and hold out one’s own hand as well.

  9. Douglas Skipworth

    Awesome post, Dave!

    In answer to your question about what I would have done differently, I completely agree with you. The #1 thing I regret is not starting earlier. If I had started the first time someone told me about real estate, I would be in a totally different place today.

    That said, I love the quote about the planting a tree.

    When’s the best time to plant a tree? 25 years ago. When’s the second best time? Today!

    I also wish I had used some conventional Fannie Mae investor loans before I went directly to the commercial banks and started borrowing. The long-term fixed rate money from Fannie would have helped me build a nice portfolio of higher-end properties instead of focusing on B- properties at first.

    Lastly, I wish I had met Jim Rohn and other mentors like him 20 years ago. I did not realize the tremendous importance of surrounding myself with great ideas and great attitudes. I’m just so thankful I’ve got them (and the greater BiggerPockets community) now!

  10. Alan Mackenthun

    I started looking at residential real estate investment seriously in the early 2000’s. Unfortunately, when I did the math on potential deals, I couldn’t find any cash flow. When the market crashed, that changed and we started buying. I wish we could have been more aggressive at that time. If we’d gotten in sooner, we’d have had more experience and we’d likely have been able to be more aggressive, but it would have been an expensive lesson and we might then have been soured on the strategy. Getting started during the savings and load crisis of the late 80’s would have been great, but we weren’t in position to do so then so we’ll wait for deals as they come and when the next crisis hits we’ll be aggressive.

    • Dave Van Horn

      Hi Alan,

      You’re right about being ready to strike while the iron is hot, but it’s also important to remember there are other markets and profits to be had at any time. For instance, when the Real Estate market crashed in ’08 I personally would have been in a rut (and maybe still would be in a rut) if I stuck with traditional hard property investing. That was when I moved to notes and formed a business that created synergy between the two sides of Real Estate and invest in markets nationwide.

      And it doesn’t always have to be a different form of investing, I have friends who live in California that refuse to own buy and hold Real Estate because the lack of cashflow. So they shifted markets and looked to places like Texas, Arizona, Nevada, etc. Wherever the deals are to be had.

      Best,
      Dave

  11. Charles Morgan

    Delegate? Does that mean paying someone to do something you can do better? LOL.
    Yes that is one of my downfalls currently but I am learning as the cudgel hits my head over and over. (And as my knees protest when I get out of bed in the morning).
    Seriously I do enjoy the feeling of seeing my own work bring back to life a neglected property but that’s not the quickest way to get rich. Great article!

  12. Nancy Emineth

    Hello Dave,

    Your article and regret comments are very helpful. These areas of investing should be considered if the goal is to achieve a certain level of success at an earlier stage without delay.
    Personally, I benefit from your wisdom and knowledge.

    Thank you for keeping us focus and engaged in the profession.

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