Real Estate Investing Basics

The Top 3 Things I Wish I’d Done Differently as a New Real Estate Investor

Expertise: Landlording & Rental Properties, Real Estate Investing Basics
20 Articles Written
Man sitting in a car and adjusting rearview mirror, car interior

You know that saying that goes, “If only I had known then what I know now”? Well, that statement is front and center for most real estate investors—especially me.

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Maybe you wish you had vetted a partner better, but instead they ended up not working out and you lost money. Or maybe you wish you had gotten a home inspection on a duplex that ended up having faulty electrical.

Here are three specific things I wish I had done from the start of my investing journey.

Looking Back, I Wish I Would Have…

1. Utilized property management software from day one.

You’ve likely heard of at least a few: Appfolio, Buildium, and Tenant Cloud, for instance. These tools are nearly a one-stop shop for anything you need to do in your real estate rental business.

For example, these tools can:

  • Request, accept, and track rental payments
  • Request and track maintenance requests
  • Hold everything from receipts to leases
  • Push out rental ads to various platforms like Zillow, etc.
  • Be used for accounting
  • And so much more!

Sad businessman leaning on glass

Unfortunately, I did not start out using one of these platforms. Instead, I use four or five different stand alone tools that do not integrate well with each other.

I track all my rent payments on an Excel spreadsheet (I know, I know…). All my leases are generated via HelloSign. My accounting usually consists of an all-out binge session 24 hours before it’s due.

Related: 3 Invaluable Lessons Learned From 30 Years of Investing

I am currently trying to integrate all of my information into a platform. I can tell you, for sure, it is much harder doing it now than it would have been setting it up from the very start.

Lesson: Pick a platform and go with it. Use that platform as your main hub for all of your rental real estate activities. It pays to be organized in the long-run.

2. Found and utilized private money.

I have funded and purchased all of my deals by myself. I have a decent 9 to 5 and have purchased one property a year, more or less. I know you can get super creative and maybe get one or more properties for no- or low-money down. However, it would be a heck of a lot easier if you had someone who was able to fund or help fund your deals.

Being a newbie does not normally lend well to your credibility; therefore, maybe you do need a deal or two under your belt before you start pitching to your rich uncle a real estate idea that you have.

Either way, if you had someone who could provide capital, you could scale your business much faster.

For example, right now, I just picked up another three family via creative means. In the past, I have used hard money, and anything you budgeted for on the rehab was reimbursed to you. This time, it is all on me! Any surprises on the rehab are all on me.

Man sit on the Bench looking out a sunset over grassy field

Unless you have deep pockets, this process can get dicey; your bank account can really start to sweat. It sure would be nice to have someone backing you up—even if you owed them a fairly healthy interest rate or a good chunk of equity.

Lesson: Head out to your local real estate meetup. Start talking to people, and tell everyone what you are doing. You just never know who has some money they are looking to invest.

3. Done a marketing campaign to capture off-market deals.

Here is something I had never done up until about one week ago. Our first cold call campaign yielded incredible results. We called around 400 property owners; around eight of them are interested in selling their properties. It looks like one to three of them might be great deals.

Related: Life-Changing Lessons From 9 Awesome Real Estate Books

We hired a virtual assistant and discussed with them exactly what we were doing and what we expected from them. They made the calls and passed along the results. Any warm leads we had, we personally followed up via a second more detailed call or meeting.

What if I had done this from the start? There are probably countless deals that never made it on the MLS that I could have found using this strategy. Even if I did not have the means to actually buy them, I could have wholesaled them or partnered with a wholesaler to sell them.

Lesson: Deal flow is crucial. There are countless possibilities as to what can be done with a good deal. If you truly have a good deal, more than likely, someone will help you buy it or someone will buy it from you. As you may know, as soon as you have that equitable interest in the property, a lot of options start opening up for you.

The Bottom Line

Overall, mistakes are okay to make as long as you learn from them. I have made plenty of them—including not doing any of these three things from the beginning. If you are starting out your real estate journey now, please do these three things. You will thank me down the road when you are behind the wheel of your well-oiled real estate machine.


What firsthand or secondhand lessons have you learned that can make beginners’ lives easier? 

Share in a comment below!

Ryan Deasy, of Deasy Property Group and RentReddy, is a long-distance landlord currently residing in Houston, Texas. Originally from Connecticut, Ryan has employed various strategies and studied unique niches in order to grow and manage his portfolio. In 2012, Ryan purchased his first duplex. Little did he know, he had stumbled into house hacking and, from there, never looked back. In 2016, he moved to Houston and left all of his rentals behind with no property manager. Through many trials and tribulations, he discovered the best way to manage his portfolio was, simply, by himself at a distance. After employing rock solid systems and an all-encompassing team, he has been able to scale his portfolio without missing a beat. Not only is his entire portfolio managed from out-of-state but it is also comprised entirely of rent-by-the-room arrangements. With the appropriate systems and teams in place, Ryan has taken a group of small multifamily rental properties and made them into an exceedingly profitable income source.
    Chris Gerstner from Plano, TX
    Replied over 1 year ago
    Ryan, Thanks for the great article! I'm just starting out after lots of learning and completely agree on #1. Great software can make a great difference. I'll have to keep my mind and ears open for private money opportunities also. #3 is completely new to me! I love the idea of cold calling. I would venture a guess that it is very underutilized as most people would shy away from it. There probably are a lot of great deals getting covered in postcards and still no response. Any recommendations on how to gather the list? Thanks again!
    Ryan Deasy Rental Property Investor from New Britain, CT
    Replied over 1 year ago
    hey chris, thanks for reading! see my comment below on the list. thanks so much.
    Buddy Shively
    Replied over 1 year ago
    Ryan--Thank you for taking the time to share your experience. I just signed up with Bigger Pockets last week and can't believe how much there is to learn. To echo Chris, do you have any tips on gathering a list of leads besides documenting the houses that might be of interest and tracking the owner down on the County Assessor's GIS platform? All the best!
    Ryan Deasy Rental Property Investor from New Britain, CT
    Replied over 1 year ago
    hey Buddy, thanks for commenting! check out my answer below.
    Tanveer Mostafa from Toronto, Canada
    Replied over 1 year ago
    Hi Ryan, great article and very well written! I had a question about your third point, how did you find a list of property owners to contact?
    Ryan Deasy Rental Property Investor from New Britain, CT
    Replied over 1 year ago
    hi Tanveer! thanks for checking out my article. please see my answer below.
    Natelya G. Rental Property Investor from Macon, GA
    Replied over 1 year ago
    #1 is crucial!! I chose a platform but my husband wanted to change and I had to explain how hatd it is...just do good research, choose one and stick with it.
    Ryan Deasy Rental Property Investor from New Britain, CT
    Replied over 1 year ago
    Natelya, thanks for reading! yes you are right. it is crucial...and very hard to change. i am with you 100%.
    Ryan Deasy Rental Property Investor from New Britain, CT
    Replied over 1 year ago
    Hi everyone, thank you so much for reading and the comments. i have someone building my list. however, it appears (i just did a search) that there are a whole bunch online platforms that can help you. i just messed around with and it seemed to be useuful!
    Colter Doty
    Replied over 1 year ago
    Great article! I’m a brokerage owner of an agency in Dallas, Tx and this is the next step for my real estate business. Some great points in here.
    Max Wexler from Minnetonka
    Replied over 1 year ago
    Ryan, Great advice! As I am looking for my first property in Minneapolis, I will use your advice as a guideline.
    Travis Henderson Investor from Manchester
    Replied over 1 year ago
    Great article
    Siva Sivakumar from East Longmeadow, Massachusetts
    Replied over 1 year ago
    nice advice, thanks