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Profile of a Female Investor: Samantha Osborne


I think it's smart to communicate to people about your goals and love of real estate. People then know that you are educated and interested in the topic and that can eliminate barriers to financing.

Samantha Osborne

Caveat before I start this blog: there’s nothing inherently special about being a female investor but since they remain a minority in the space, it’s important to spotlight them.

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Incredibly reductive picture of Samantha:

Works in digital marketing, has a very cute dog named Izzie, is introverted and goal-oriented.


Overview of Investments

  • Michigan

  • 1st property (sold after 3 years)

  • duplex (long term rents)

  • single family home (short term rents)

  • Church (in development)

  • Colorado

  • Denver - Primary home (house hacking)

  • Colorado Springs (Single Family House, furnished, long term rental)

Tell me about your investments..


My real estate journey started when I was 24. I bought my first house in Michigan and sold it after 3 years. I then moved to Denver, where I rented for a year with my now-husband. I decided after a year in Denver that I didn’t want to pay rent anymore, so we used the money off the Michigan sale for a downpayment for a house in south Denver. When we bought in Denver, we rented out to a friend because we liked the idea of someone paying out part of our mortgage (house hacking).


Our next buy was in Michigan. We had property management there, and they were more affordable, so cash flow was good, but now our goal has shifted from cash flow to long-term equity and investment.


After we finished that, we bought another one, rehabbed from top to bottom. Like Chip and Joanna Gaines. Not sure if I’d still do that again. Took 6 months. We did short-term rentals on that. Liked that because it helped me combine two things I like: hospitality and real estate. It’s been very, very successful. More than we anticipated.


While we were finishing that up, a church came up for sale. We were excited to the location, close to the beach and we knew how well our Aibnb had done, so we got that property rezoned. It’s sectioned up into 4 units and then maybe two condos in the parking lot and that will kick off Memorial Day,


Our next (and most recent purchase) was the Colorado Springs house.


Tell me more about the Colorado Springs' house.

It's a single family house. Purchasing through the pandemic was easier for us than we thought it would be. We made an offer without even seeing it after seeing video.

Something that was interesting for people to know is that the property was priced where it should be without issues, but there were significant issues in the basement with water. I think a lot of people would have run there, but we used it as an opportunity to be creative about sale and purchase. Tried to quote out how much it will cost to contract. What will it cost to demo. We came out pretty far ahead.


Who are you renting it to?

  • We put it up for rent and we had 5 grad students that were interested. We had other people. But what made them most appealing was that it was July 2020, we didn’t know about job stability, so having 5 people on the lease with their parents co-signing with credit checks made us more confident about maintaining that property. They ended up signing. We knew they were moving back into the state from out of state. Since moving during the pandemic is not fun, we asked them if they were interested in us furnishing it. They were elated. That was great for us because it actually financed furnishing the whole house. It also was good for them because they didn’t have to pay for a bunch fo stuff they didn’t necessarily need after that.

Has investing gotten easier for you?

The more you invest and the more you talk to other people, it gets easier. My biggest thing as far as a checklist is looking at potential rates, short or midterm income for the month. Low end, high end and check vacancy rates. At end of year, I can see our benchmark for a low year, high year and if we’re not hitting x amount for low end, then this is no longer a profitable property.


How do you manage the fear of investing?

  • If you think through them and can talk through them and say what is or what are my three biggest fears, I find if you write it down and you have the solution in front of you, you kind of let it go.

Covid is a good example fo things going sideways. How did it look like as an investor?

With our Michigan short-term rental, we had a bunch of bookings last March through the Spring. In February, we were talking about not being able to keep up. The week after everything was canceled, a month and a half out.

  • There were so many people that needed somewhere to stay during an uncertain time that we had thought about. For example, there was a young woman out of NY, who wanted to come back and see her family but wanted to quarantine for two weeks before seeing them. At that time, it was kind of scary as an Airbnb super host, we didn’t know the precautions we needed to take, how it was transmitted, or how to clean.

  • She came for a month and it worked out great. She came back and asked to rent it out for 6 months. We declined to do that because the numbers didn’t make sense any more.

Any changes to your investment strategy post-pandemic?

  • Pre-pandemic, I worked remotely for 3 years. It was a huge eye opener for me. I worked in MI but lived in Denver. I realized not every job can be done remotely or online, but a lot can be and can done way. I kept saying to my husband, “I’m not sure why they keep building all these office buildings or being tied to somewhere they don’t want to live.

  • Colorado, the sunshine and mountains are not going anywhere, whether that’s a short term, mid term or long term.

  • Re long-term equity, depends on where you are at with your lifestyle or job or how eager you are to get out of it. That might not be for everyone, when I looked at cash flow, I saw it as this can replace my paycheck and it will be so much easier. Now looking at cash flow on properties in Michigan, it’s a little more than in Colorado, but you know when we go to pull a HELOC or refinance, the amount of equity, we gain in one year or three years in Colorado is 50x what we might make in MI off of cashflow in 10 years. It made more sense to us.

Any other advice?

  • I think it's smart to communicate to people about your goals and love of real estate, people know that you are educated and interested in the topic, eliminates barriers to financing. Encourage people to talk about these things with people they trust and put it out there to their circle.

  • I don’t regret even difficult tenant or difficult property, because it was worth it. It’s just sort of like what did we learn and what’s next?


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