From Engineer to Empire Builder: Grace Gudenkauf’s Journey to 20+ Units

WIIRE podcast
By The Hospitable Team

In this episode of the Hospitable Hosts podcast, we're excited to welcome Grace Gudenkauf, a real estate investor who quit her engineering job in 2021 to build a thriving rental business. Grace owns and self-manages over 25 units across multiple states, including short-term, mid-term, and long-term rentals. She is also a co-founder of Women Invest in Real Estate (WIIRE), a community for aspiring and existing female real estate investors.

Grace shares her incredible journey, from taking the plunge to building a team and empowering others through her book and community.

Tune in to the full episode of the Hospitable Hosts podcast to discover how Grace has built an impressive career in real estate and become a master of remote management.


Do you prefer to read the highlights? We've got a summary of the key takeaways below.

Why Real Estate Investing?

At the beginning of the conversation, Grace admits that she took a leap of faith when she quit her stable engineering job and decided to work full-time in real estate. She always knew she wanted to own a business but never knew what it would be.

"And so when real estate came to me, I started delving into it in 2020, 2021. I was also supposed to move to California for my job in the middle of COVID. I took a good hard look at my life, and I was like, I think this is the best time it's ever gonna be to take a risk. I looked at my worst-case scenario and decided I could handle that. So let's do it."

Growing Rental Portfolio

Grace started as a DIY investor in her backyard. Now, she owns and self-manages 25+ properties in Eastern Iowa while living in Tucson, Arizona. She uses the BRRRR method to expand her real estate portfolio efficiently.

Grace operates short-term, mid-term, and long-term rentals. She wasn't sure whether mid-term rentals would work in her market, so initially, she tried just one unit that was empty when she bought it.

"I spent $3,000 on that one to see if this furnished rental would work. And it did; I got bombarded with requests. So then I did the next one. And I just kept doing that and had a pulse on the demand I felt from Furnished Finder and Airbnb until I had 12 or 13 midterm rentals."

Self-Managing Vs. Hiring a Third-Party Manager

Grace admits that self-managing was rather emotional when she first started. "You've bought this super expensive asset that could change your life. And you have somebody living there who might not respect it or have their emotions involved," she explains. So, Grace had to learn to have systems and boundaries, see red flags, and tackle minor issues before they escalate.

Grace thinks everybody should learn to self-manage so they're not "dependent on a third-party manager who takes 10 % and makes your rentals their last priority." She learned a lot by doing it herself, and although she decided to hire a manager internally to help her self-manage, she won't hire a third-party property manager in the future. "I think that real estate is an incredible asset, and you should be the number one person in charge and the number one person caring about your property at all times," she underlines.

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Tech Stack That Grace Uses

Grace says Hospitable was the first platform she used to manage turnovers, cleaners, and tasks when she started running mid-term rentals 3 years ago. She's also using Tenant Cloud to manage her long-term rentals regarding maintenance, communication, and applications.

"I'm a big proponent of being the CEO of your business, the CEO of your portfolio. You need to look at things like QuickBooks, Google Drive, and other pieces of technology that keep your business systemized and organized so that you can focus on making money in your business," Grace recommends.

Helping Women Invest In Real Estate

Grace is passionate about empowering other women to achieve financial freedom through building a real estate business that matches their lifestyle. With Amelia McGee, a full-time real estate investor, Grace created the WIIRE community for women investors who want to "live a life by their own design." Grace and Amelia are also co-authors of the book The Self-Managing Landlord.

"But WIIRE is special because we never started it as a business," Grace reveals.—"We started it as I'm doing real estate. I want to meet other people doing real estate who are young and passionate, doing these cool things and taking life by, you know, the horns and creating a lifestyle that they want to live. And it slowly morphed into an actual business. Now we have team members across the US, hundreds of people in our WIIRE community, but it remains committed to helping women learn real estate."

Listen to the full episode of the Hospitable Hosts podcast to get inspired by Grace's journey in real estate investing, from quitting her corporate job to becoming the CEO of her business and building a thriving community for female investors.  

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