The Insider: Grace Gudenkauf on Women Investing in Real Estate

Looking forward to ​@Grace Gudenkauf joining us for this one! Grace is an MTR expert - so if you’re considering switching to some MTR bookings in the upcoming slower season, get asking your questions now!

As a founder of Women Invest in Real Estate, what common barriers do you see holding women back from scaling their business, and how can they be broken?

How do you think the proposed 50 year loan might impact real-estate, and STR specifically?

Hi all I can’t wait until tomorrow. Go ahead and ask me anything and I will be ready to deep dive tomorrow with you all! 

Hi ​@Grace Gudenkauf! Fun to see you here! 

I own one property, it’s a vacation home in a popular vacation market, so I only do short-term rentals there. I’ve been interested in purchasing a property closer to my home, which isn’t a vacation market. Long-term doesn’t interest me, but I’d love to get into mid-term. 

• How would you recommend I analyze new properties to determine if it’s a wise investment? There are so many reputable tools out there for short-term like AirDNA, which even DSCR lenders would use to qualify you for a loan. But tools to analyze mid-term deals are less known; help us know where to start!
• Do you have experience with placing mid-term tenants through insurance companies? How do you approach an insurance company to get on “the list” and how do you optimize your property to be a good fit for those types of tenants?
• What other avenues are there to match with mid-term tenants, outside of Furnished Finder? What about universities? Temporary work placements? Etc?

Can’t wait to hear from you!

Hey ​@Grace Gudenkauf, I am humbled to get the opportunity to ask you a question. 

I just launched my first MTR on Airbnb and am working to also list it on Furnished Finder and Facebook Marketplace soon. I have my instant book off on Airbnb so I can screen my guests prior to booking. When booking guests leads from Facebook Marketplace and Furnished Finder, I want to ensure my guests have a secure platform to pay rent electronically and sign a rental agreement/lease electronically. 

1. How can I properly screen guests while having instant book on? I know about 60% of guests book with instant book and want to take this opportunity.
2. What do you recommend I use for payment and lease signing for Facebook Marketplace and Furnished Finder? I know Hospitable can help… should I get my own direct booking website via Hospitable to fit these 2 needs or use other platforms for payment and lease signing? Trying to utilize the most cost effective method since I only have 1 MTR and 1 STR.

Thank you in advance!

Jess

Welcome everyone to today’s Insider session! 💜

We’re thrilled to have ​@Grace Gudenkauf with us: a full-time investor and co-founder of Women Invest in Real Estate (WIIRE), where she helps women build confidence and financial freedom through real estate.

If you’ve ever thought about getting started in investing, scaling beyond one property, or balancing it all while self-managing, this is the perfect session for you. Grace has been there: from quitting her engineering job to building a 25+ unit portfolio, and she’s here for the next hour to share what worked, what didn’t, and what she’s learned along the way.

Drop your questions and jump into the conversation.

Let’s get started!

Great question. Representation is crucial because women tend to invest and run businesses in a much more conservative manner. Whether that’s a lack of access to capital, a lack of confidence due to not having representation in the industry or within real estate specifically, having less exposure to construction and hands-on projects in life in general. To break this it’s important to have a community that can help you move forward in your business, whether that is local or something online like this Hospitable community. Additionally, I would love to see more training for women in the space specifically about construction and trade skills.  

When the barrier to entry is lowered, such as a lower payment due to a 50 year amortization, a lot more buyers will enter the market which will drive up demand and therefore price. This means more people will be looking at buying homes, investing and doing STR. All of this creates competition. Another impact that will be seen is that principal pay down is much slower, meaning that owners are gaining equity more slowly. This means owners may have less flexibility for exit strategies such as selling or refinancing, both of which require equity to do so without losing money. 

A great hack potential MTR investors can use is to throw up a test listing on Furnished Finder to test out demand. For example back in 2022 when I did my first MTR I listed the property with unfurnished photos, but I made sure to explain that it would be furnished. I also borrowed a friends’s furnished photos to show the potential renters what type of furniture they could expect (Will it be old worn out furniture or new, stylish furnishings?). This was a lower risk way for me to test the response from the market. You could do this too, even if you do not own the property. Just make sure to quickly get back to anyone interested and either tell them it’s been rented or no longer available, we don’t want to leave anyone hanging!

Hello Grace!

I’ve been thinking about buying a small property and adding an ADU in the back. Any tips for financing out this build? Also would love any tips on making sure the math works before I commit!

Some other tips when it comes to analyzing MTRs are that utilities and vacancy are going to be your most important expenses to nail down. Always be conservative with vacancy- I use 10% minimum in my market, but it depends on your own strategy and market. Many utility companies have a feature which you can look up an address and see average utility costs of the last 12 months. Use it! Then you need to be able to accurately estimate the MTR rent. This is an art more than a science. Look at comps at Furnished Finder. How similar are they? Are the amenities the same? Pet friendly? How many guests does it sleep? Again, be conservative and make sure the property has multiple exit strategies if MTR tenants slow down. 

Hi Jess, congrats on your first MTR. Yes, I would use Hospitable. Since you already use it, it’s the most cost effective option. Their direct booking feature should be able to handle the payments and deposits. They also have integrations with screening platforms. Another option is to use a platform directed to long term rentals like TurboTenant. Many investors that do LTR and MTR will just use one software for both, but at the end of the day it’s whatever works best for you. 

You’ve built such a beautiful community to support women, can you tell us more about WIIRE? How can hosts join, and what can they expect to find there? I see you offer courses too, is there maybe a training focused on construction and trade skills for women in the works? :)

I am building a new construction triplex right now! Start by calling local builders to get a rough estimate of the price per square foot to build. A huge cost saver is if there are already utilities and an existing slab. I bought a property that needed torn down, new utilities and of course all new foundations. That was a VERY expensive part. So if there was a house you could find that had a pad already poured that could be very attractive. As far as financing, a small local bank will be your best friend. One of the best things I ever did was I got connected with a local bank 5 years ago when I started and I have been building that relationship ever since. They will be much more flexible with you once you prove you are an experienced, able borrower and investor. Plus they typically have much lower fees and work faster. 

Funny that you ask Petra! I was just at my new construction project this morning talking with a female concrete contractor who is just 22 years old. I was so intrigued learning about her and mentioned that at WIIRE we have been looking at hosting in person events to teach the basics of the trades so that we can feel confident as investors to run our projects, talk to contractors and estimate pricing. It isn’t planned yet but it is absolutely on our radar for a 2026 event!

And thank you for the kind words about WIIRE. Our mission is to empower women to become W2 optional through real estate investing so they can life a life of their own design. We do retreats across the US, and have an online community of 250+ members. Studies show that when women control wealth, they invest more heavily back into their neighborhood, their community and their families. Our mission isn’t just to help people build wealth, it’s to also teach women how to be ethical landlords that make our communities a better place. Our investors leave their neighborhoods better than they found them, empower their tenants, and provide safe and updated housing to their communities. The doors to WIIRE open a few times a year and will next be open in January :)

For screening guests, Airbnb does allow you to set requirements in order for guests to instant book. I will admit I do not have a perfect process for this, but what is most important is that you monitor it closely and pivot quickly when needed. For example if you want to give instant book a try, you could give yourself a specific time period to monitor and then decide at the end if you like it or need to pivot or implement a different system in order to get the right tenant. Good luck!

It definitely sounds like that course is on the horizon. I’m sharing the WIIRE link once again for those potentially interested in joining: https://www.womeninvestinrealestate.com/

I’m also curious, looking back, which investment decision or property taught you the most? And why?

Additionally, how do you evaluate whether a new property should be short-, mid-, or long-term?

I have done a lot of projects, and I have made a LOT of mistakes. The biggest thing that I have learned is that it is OK to sell properties as you and your business evolve. When I first got started I genuinely believed I would own every property my entire life. LOL! Now, I am slowly pruning my portfolio to keep the very best properties that are the least maintenance, with the best tenants. I am looking at slowly decreasing the average age of my portfolio too. I am selling off my older properties and reinvesting into new builds. When it comes to evaluating what strategy I want to use I am of course leaning heavily on what ROI it is going to give me, but I am also considering the return on my time and effort. This isn’t talked about enough. I am no longer willing to do things to make an extra $50/month like I was when I first started investing at 22. Instead I prefer passiveness over scrappiness. But it has taken 5 years to get here! One step at at time. 

You started investing in real estate relatively early. What sparked your interest / got you started?

A big thank-you, ​@Grace Gudenkauf, for taking your time today and sharing you story and insights! 💜

So, this thread will stay open until tomorrow at 12 PM ET, so feel free to add any last thoughts and follow up questions before it closes. 

Stay tuned for our next Insider spotlight, and if there’s someone you’d love to see featured, drop their name in the comments!

Thank you for the great questions, and good luck to you all! 

I always knew I wanted to own my own business. My boyfriend, now husband, used to listen to Bigger Pockets in college and he flipped a house when I was still in college. It got my gears turning and when I graduated I wanted to do something smart with my engineering income, and something that would get me through a boring midwestern winter. So we found the worst house we could find to DIY. It took 6 months and double the anticipated budget but somehow we were hooked. :)