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Thinking about buying an investment property but not sure where to start? Whether you're considering a rental property, duplex, short-term rental, or your first real estate investment, this episode is packed with practical advice to help you make informed decisions.

Join Jannea Wood, Tiffany Tobias, Katie Kolakowski, and special guest Sherry McKee, as they break down the fundamentals of real estate investing and discuss what every new investor should know before purchasing an investment property in Madison, Wisconsin and beyond.

🎙️ About It's Like That Madison
Hosted by local Realtors Jannea Wood, Tiffany Tobias, and Katie Kolakowski, It's Like That Madison explores real estate, neighborhoods, local businesses, lifestyle topics, and everything that makes Madison, Wisconsin such a great place to live.

📲 Follow, subscribe, and leave a review if you enjoy the show!

#InvestmentProperty #RealEstateInvesting #RentalProperty #MadisonWI #MadisonRealEstate #PassiveIncome #RealEstatePodcast #LandlordLife #HouseHacking #WisconsinRealEstate #RentalIncome #PropertyInvestment #ItsLikeThatMadison #DuplexInvesting #WealthBuilding

Jannea Wood, Stark Company Realtors: https://jwood.starkhomes.com/ Instagram

Tiffany Tobias, Stark Company Realtors: https://ttobias.starkhomes.com/

Katie Kolakowski, City RE: https://www.cityremadison.com/

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Episode 11: What Does a Realtor Actually Do for a Buyer?

Think Realtors just unlock doors and write offers? Think again.

In this episode of It’s Like That Madison, we break down what actually happens behind the scenes when you’re buying a home—and why having the right Realtor can make or break your experience.

From your very first consultation to the final closing table, we walk through every step of the buyer journey: building a strategy, navigating showings, crafting competitive offers, negotiating terms, managing inspections, and keeping everything on track when things get complicated (because they always do).

Whether you’re a first-time home buyer or you’ve been through the process before, this episode gives you a clear look at the value, expertise, and advocacy a Realtor brings—especially in a competitive market like Madison, WI.

If you’ve ever wondered what your agent is really doing behind the scenes… this one’s for you.

Jannea Wood, Stark Company Realtors: https://jwood.starkhomes.com/ Instagram

Tiffany Tobias, Stark Company Realtors: https://ttobias.starkhomes.com/

Katie Kolakowski, City RE: https://www.cityremadison.com/

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🎉 Episode 10: How It All Started + Celebrating 10 Episodes! | It’s Like That Madison Podcast 🎙️

We made it to Episode 10! 🎉 In this special milestone episode of It’s Like That Madison, hosts Jannea Wood, Tiffany Tobias, and Katie Kolakowski take a step back to celebrate the journey so far—and share how the podcast all began. And you get to meet Jeri who makes it all possible.

From the original idea to launching the first episode, we’re giving you a behind-the-scenes look at what inspired us to start a Madison-based real estate & lifestyle podcast, what we’ve learned along the way, and some of our favorite moments from the first 10 episodes.

If you’ve been following along, thank you for being part of this journey—and if you’re new here, this is the perfect episode to jump in and get to know us!

Whether you're interested in Madison real estate, local lifestyle, or just love a good behind-the-scenes story—this one’s for you.

📍 It’s Like That Madison is your go-to podcast for all things Madison, WI—real estate insights, local favorites, neighborhood highlights, and more.

👍 Don’t forget to like, subscribe, and follow along for future episodes!

Jannea Wood, Stark Company Realtors: https://jwood.starkhomes.com/ Instagram

Tiffany Tobias, Stark Company Realtors: https://ttobias.starkhomes.com/

Katie Kolakowski, City RE: https://www.cityremadison.com/