2021 Real Estate Investing Goals – Jenny Bayless
Jenny Bayless, Colorado Springs real estate investor and agent, discusses her 2021 real estate investing goals that she outlined in her chapter submission for the 2021 Colorado Real Estate Investing Guide set to publish in Q1 2021. Check out this episode to learn about Jenny’s strategy for goal setting, personal finances, real estate investing, and growing the Envision team down in the Springs.

When I first began investing in real estate, I had “shiny object syndrome” and it was very hard for me to hone in on a specific strategy or goal to work towards.  I found that the only way to beat shiny object syndrome for myself was to jump in and see what happened. 

As I gained more experience in investing and was able to refine the process in terms of recognizing what worked and what interested me, my big goals became quite clear!  With each passing year, I am able to more clearly define my investment goals for the near future, because I have laid the groundwork in prior years and I am ultimately working towards those big goals.

Three Learning Options!
  1. Listen to the podcast “#8: 2021 Real Estate Investing Goals – Jenny Bayless” on the Colorado Springs Real Estate Investing Podcast
  2. Watch the YouTube video (at the bottom.)
  3. Read the blog post. The blog post is Jenny’s chapter submission for the 2021 Colorado Real Estate Investing Guide. Get the in-depth conversation from the podcast or video.

My Rules for Real Estate Investment

To create my investment goals, I follow three general rules: I do not want to own an empire; making sure I don’t overextend myself; ensuring I have adequate cash reserves to cover all aspects of my life.  By keeping these rules in mind, I know my goals are not only attainable but will keep me comfortable, as well.  

  1. I do not want to own an empire.  When making decisions on which and how many properties to invest in, I keep in mind that my end goal is not to own as many properties as possible.  Instead, I want to own a portfolio of simple, cash flowing rental properties that will serve three main functions: cover all of my family’s living expenses; bring in some extra cash for some splurges; and provide a financial cushion to my daughter.
  2. Make sure I don’t overextend myself.  Investing in properties that allow us to remain financially comfortable (by not taking out too much leverage) is a relatively objective measure, but making sure we aren’t overextending ourselves in other ways can be trickier.  During the accumulation period of our rental investment career, my husband and I were both working full time jobs and spending most of our weekends painting, cleaning, and hauling trash from our BRRRR properties.  When we found ourselves trying to coordinate a window installation while on a ferry boat in New Zealand, we realized we were trying to do too much.  If we couldn’t relax while on vacation, we needed to take a step back and stop trying to do everything ourselves.
  3. Ensure adequate cash reserves for all aspects of life.  My requirement is to have six months’ worth of personal savings, as well as six months’ worth of rental property expenses that cover each and every rental property—no exceptions!  I keep all of these reserves in regular savings accounts: an emergency personal account, an emergency rental account, and a general savings account that I use for extras, such as vacations or large purchases.  Even though these accounts only earn a few cents in interest every month, it’s worth the tradeoff of knowing they are accessible and liquid should I need to use them.  I have noticed that as my portfolio and my family expand, I sleep better at night knowing I have cash in the bank to protect against hard times.

By using these rules, I am better able to frame my goals.

Personal Budgeting Goals

Fun fact: My husband and I have been tracking all of our expenses and our net worth together since before we were even married.  We enjoy looking back at our spending, earning, and savings trends to see how they’ve changed over the years.  I knew by my mid-20s that collecting a paycheck was not going to contribute to wealth.  However, it was not until we were 29 years old that we started really putting a lot of effort into real estate investing.

I firmly believe that you cannot invest successfully without first being in a good position financially (rules #2 and #3).  While I am a big fan of low cash down deals and refinancing to redeploy equity while accumulating properties, these tools should only be used to strengthen your position and never used out of necessity.  I attribute a lot of our financial strength to simply knowing where our cash inflow and outflow goes.  By tracking our monthly expenditures, we can easily identify areas in which we can reduce our spending without causing discomfort or constraining ourselves.  Keeping a close watch on our income, expenses, and net worth allows us to better plan our savings and decide how to turn those savings into income-producing assets, and use them for fun things, like vacations!  In addition to these savings, we also have retirement savings accounts from employment, as well as some stocks, which we treat as a “set it and forget it” situation.

My personal budgeting goal for 2021 is to continue tracking our income, expenses, and net worth as we have been doing.  This is the best way to avoid “lifestyle creep” and instead continue to make wise financial decisions.

2021 Real Estate Investing Goals

Between the Getting Started Guide and various Colorado Springs Real Estate Investing podcast episodes, you probably already have a good sense of my current portfolio and how it came to be.  Our present-day portfolio is the result of experimentation—we started out of state and then pivoted to Colorado Springs only; we began investing with hard money loans that came with pretty expensive terms and then were able to turn to private loans once we had a solid track record; we didn’t have a cohesive plan for fixing up our rehabs, but now we have a fantastic network of contractors.  After a lot of trial and error, we now have a good grasp of what we want in a rental property and how to get a property to that point. 

Over the years, we have refined our investing strategies in order to get to our current rental property portfolio.  For now, we are content with our strategy and holdings because they best fit our lifestyle.  At one point, my husband and I had 10 rental properties in Colorado Springs, but we sold 2 of them in order to fund our dream home.  Some people in the personal finance community may look at this as a foolish move, but we don’t regret it.  We were able to cash-in some of our hard work in order to put a good-sized down payment on our personal home, while still retaining our strong financial position.  As of the time of this writing, we own 8 rental properties in Colorado Springs and are in the process to close on our 9th this year. 

My 2021 real estate investing goal is pretty simple: I want to pick a property I currently own and pay off that loan.  Some people reading this might be cringing and asking, “Why on earth would you want to do that when you could deploy your equity into so much more?”, or “Interest rates are so low, why wouldn’t you want to borrow at those rates?” While there’s nothing wrong with those sentiments, I stick with rule #1: I am not setting out to own an empire.  We have always looked at our portfolio in two phases: accumulate the assets and then pay them off.  We have accumulated the properties that we want, so the next step is to simplify things and start to pay some mortgages down.

Real Estate Agent Goals

In 2020, I made a huge career move by resigning from my well-paying W-2 job that I held for a decade and transitioned to the world of self-employment by joining the Envision Advisors team.   I do not regret this transition for a second!

I flirted with the idea of leaving my stable W-2 job for a while, as I have the stability of my husband loving his W-2 job, and we built our real estate portfolio to accommodate such a move.  While I’d known it was time to move on for a while, it was hard to leave a good-paying, stable job.  The final push to leave came when my daughter was born, and I realized that I was fortunate enough to have the option to quit my prior job in exchange for the flexibility of being with her.  Making this decision also allows me to focus on helping others buy rental properties so that they can hopefully attain the same level of flexibility and freedom to achieve their goals, something I’m passionate about sharing.

I plan on helping the Envision Advisors team expand down to Colorado Springs, bringing to that market the same level of service and knowledge that our clients know to expect in Denver. 

When we started working in the Colorado Springs market in 2020, we weren’t sure what to expect in terms of client interest and speed of expansion.  Now that we have a general baseline from this year, these are my real estate agent/team goals for 2021:

  • Along with Chris, (sorry, Chris, but I am dragging you into this goal!), publish 52 Colorado Springs Real Estate Investing podcast episodes.
  • Quadruple the number of closed transactions in Colorado Springs from 2020 to 2021 for our clients.


2021 is gearing up to be a busy year with these goals in mind, but I am excited to work towards them.  Like many things in life, taking big steps now will provide the momentum needed to achieve even bigger goals in the years ahead.

Click here to check out the submissions page for information on how to submit your chapter.

Real Estate Investing in Colorado Springs

If you would like to learn more about real estate investing in Colorado Springs, start here. From there you can view the latest quarterly report on the Springs market or sign up for the Colorado Springs Deal Email List to get analyzed rental properties sent straight to your inbox.

The Colorado Springs Real Estate Investing Podcast

To learn more about the Colorado Springs rental market, check out the Colorado Springs Real Estate Investing podcast that I co-host with Chris Lopez. We analyze local deals and address topics that are important to Colorado Springs real estate investors.

YouTube Video: 2021 Real Estate Investing Goals – Jenny Bayless

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Jenny Bayless
Jenny Bayless is an investor-friendly agent with Envision Advisors, Colorado real estate investor, and the host of the Colorado Springs Real Estate Investing podcast.
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