top of page

Our start in real estate, year 1:

We are just now starting our social media, website, and blog, but we are almost 2 years into our real estate investing journey. With COVID and a new baby, we haven't been as connected with family and friends as usual. I'm going to use the next couple blog posts to give an update on how we got started in real estate and how things have developed over the past couple years.

Shorewood, WI

Technically, our real estate journey began when we bought our first house near Milwaukee in 2016. We knew at the time that our budget would allow for either a small but updated starter home that we would soon outgrow, or a larger home that needed some work. We opted for the larger home that needed some work. It was well maintained but didn't appear to have many cosmetic updates in the past 30 years. Over the 4+ years that we lived there, we slowly updated the house room by room. We didn't know it at the time, but it essentially ended up being a live-in flip.

One room at a time, we took on projects that we hadn't done before. We extensively researched each one online, watched YouTube videos, and read how-to posts and blogs. We did a lot of painting, refinished the hardwood floors, replaced fixtures, built custom built-ins and floating shelves, installed a tile backsplash, replaced all of the appliances, put up a composite fence, laid a paver patio, and much more. We also hired subcontractors for things like new granite countertops, carpet for the stairs, and installing a new gas fireplace. Not every project went perfectly, but we learned a lot with each one that we did. We also accumulated a lot of tools so that we could do them all again... go ahead... ask Holly about the number of tools that I have collected. Below are some before and after pictures from our Shorewood home.

In December of 2019, I accepted a work from home position (like Holly had done 2 years earlier) and we were no longer tied to Milwaukee for work. We decided to sell our home and move to southwest Michigan.

Saint Joseph, MI

We closed on our house in Saint Joseph, MI in March of 2020. We were concerned that our closing might not happen because it was less than a week after the world seemed to shut down. We were excited to be close to Holly's family and enjoy all that the Lake Michigan beach town has to offer in the spring and summer months. In 2020, that was not to be.

Instead, we were quarantining in a new city without any real opportunity to meet new friends, neighbors, or even to see the family members that we were now so close to. We were very lucky to have a larger house with even more space to spread out since we almost never left home. However, as weird as it may sound, we missed the projects. Our house in Michigan was much newer and much more turn-key. There were little things to be done, but not many big projects like we had in Shorewood. Our renovations had become our night and weekend hobby over the past 4 years. Like many others during this time, we struggled with being cooped up in the house for weeks at a time, and in a way it would've been nice for us to have some projects to work on to keep us busy.

As summer turned to fall, Holly came to me with an idea. We had been setting aside a good portion of our paychecks each month into invest into the stock market. We have a massive amount of student loan debt that we will never pay off making our income-based monthly payments. Someday (10 or 15 years from now) the balance will be forgiven as taxable income. This will require us to have over $150,000 on hand just to cover the taxes on the debt that is forgiven. I will make another post at another time about our student loan paydown strategy, but we knew that we had to be saving up for this. Her idea was to use some of that investing money that we had saved to buy an investment property. It could either be a flip or a rental, but it would likely outperform our returns in the stock market and it would give us somewhere to go and something to do. We had plenty of time to put in some sweat equity and the real estate market had taken a dip so the timing seemed right.

While we had talked about having rental properties casually in the past, anyone that knows us well knows that we don't take decisions like this lightly. We built out spreadsheets with multiple tabs and scenarios to project our returns. We started to learn as much as we could about investing in real estate, and we started following listings in our area (for sale and for rent) daily. Ultimately, we decided to go for it.

After analyzing some properties in our market, we found one that fit our criteria. It was below our budget, in a great area, had good bones, but required a good deal of cosmetic renovations. We put in an offer and after some back and forth, it was accepted. We closed in November of 2020 and our investing journey had begun. Looking back, we didn't have the level of knowledge that we should have at that time. We still had a lot to learn. But while we continued to read books and listen to podcasts about real estate investing, we learned more by actually jumping in and doing it ourselves than we ever could have from just learning from others. The decisions that we made on that first property weren't perfect, but instead of looking at them as successes or failures, we looked at them as successes or learning opportunities. Mistakes that we made were things that we would know how to do better on the next one.

Our renovation started in November and finished in May. We painted the house inside and out and replaced all of the flooring, door knobs, hinges, and fixtures. In the kitchen, we replaced the mismatched appliances, added quartz countertops, and added a backsplash. In the bathroom we tiled the floor and shower and replaced the vanity, mirror, and fixtures. Below are a few before and after pictures of this property.

As we progressed through the renovation, we started to realize that we didn't know anything about the next step in the process. We didn't know how to find and screen tenants, how to write a lease, or how to be successful landlords.

As healthcare providers, we were lucky to get our COVID vaccines in January and February. In the end of February (exactly 14 days after our second dose), we took a trip to Hawaii which was both amazing and strange because of how empty it still was. On that trip, Holly and I both read "The Book on Managing Rental Properties" by Brandon and Heather Turner.

This book was a game changer for both of us. It provided a mind-blowing amount of information on a number of topics that we hadn't spent any time thinking about. It taught the importance of treating property management as a business and not a hobby, and how to create systems and processes to more efficiently manage properties and tenants. We starting thinking about how to collect rent, how to manage maintenance requests, property management software, book-keeping, building a forms repository, getting a business phone line and PO box, developing a website, asset protection, and a whole lot more. In a matter of days, we went from only thinking like a contractor to also thinking like a property manager. We were making progress on the path to thinking like a well-rounded real estate investor.

After having a couple days to process all of this new information on a different side of the business, Holly and I went to our favorite coffee shop on Maui and sat and had a long morning talk overlooking the ocean. We had a decision to make.

Option 1:

  • Grow our portfolio slowly

  • Take a more DIY approach to managing our properties to keep our expenses as low as possible

  • Look to add more efficiencies if and when we felt that we had enough properties to warrant it

Option 2:

  • Commit to real estate investing more aggressively over the coming years

  • Spend the money, time, and effort now to put systems in place that are overkill for only 1 property, but will allow us to scale within those system and not have to reinvent the wheel each time we outgrow our current systems

It wasn't an easy decision. We were looking at monthly expenses of about $240 to setup all of the software, subscriptions, and systems to help us optimally manage our business. Our 1 house was set to have about $510 cashflow per month after all expenses and reserves, which would be reduced almost in half to about $270 after all of these business expenses. But on the flipside, the faster you scale, the more these expenses are spread out across your portfolio. Each time you add a property, your cashflow goes up on all of your other properties. Most of the expenses are fixed so when you get to even 5 properties, this $240 comes down to less than $50 per property per month. Again, we decided to go for it. We settled on option 2 and committed to growing our portfolio. We didn't know how we would do it yet, but as we would later find out, when you have the correct mindset things come together in ways that you don't always see coming.

After Hawaii, we were both finishing our renovation and setting up all of the components needed to run our property management business. It ended up working out well for us that an unexpected situation resulted in a family member renting our property from June through August. By September, our property management company was ready and we listed our first rental property on Zillow. I will spare you all of the details, but our process couldn't have worked any better. We found an incredible, well qualified tenant, and on October 1, 2021 we handed over the keys to our first rental property knowing that it was in good hands.

From our initial search for our first rental property to the start of our first lease took almost exactly 1 year. During this time, we did a full renovation, built our property management business, and put together the systems and structure that would allow us to scale. Most importantly, we made the commitment to keep moving full steam ahead. Even with that mindset, we had no idea what was in store for us in year 2...

22 views0 comments

Recent Posts

See All


bottom of page