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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/

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🏠 Home Inspections: The Good, The Bad, & The Ugly | It’s Like That Madison – Episode 9

Buying a home in Madison, Wisconsin? A home inspection can make or break your deal.

In Episode 9 of It’s Like That Madison, hosts Jannea Wood, Tiffany Tobias, and Katie Kolakowski break down everything you need to know about home inspections — from the routine fixes that shouldn’t scare you, to the red flags that absolutely should.

We’re talking:
✔️ What a home inspection actually covers
✔️ The difference between cosmetic issues and major structural concerns
✔️ What’s negotiable after an inspection
✔️ Common inspection findings in Madison-area homes
✔️ When to walk away
✔️ Real stories — the good, the bad… and yes, the ugly

Whether you're a first-time home buyer or a seasoned homeowner in Dane County, understanding the inspection process is critical in today’s market. We explain how to approach inspections strategically, protect your investment, and avoid unnecessary panic over minor items.

If you're buying a home in Madison WI — or thinking about it — this episode is a must-watch.

🎧 Available on YouTube, Apple Podcasts & Spotify
📍 Real estate insights + real talk, right here in Madison, Wisconsin

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 8 – What to Know When Buying Your First Home | It’s Like That Madison

It’s a new year, and if buying your first home is on your mind, you’re not alone. In Episode 8 of It’s Like That Madison, we break down everything first-time home buyers need to know before jumping into the market.

From understanding the first-time home buying process to navigating today’s Madison, Wisconsin real estate market, we cover what truly matters—and what doesn’t. We walk through how we work with first-time buyers, the steps we take to set our clients up for success, and the common mistakes we help buyers avoid.

A big topic this episode: Buyer Agency. What is it? Why does it matter? And do you really need to sign a buyer agency agreement before seeing a house?

We also share our personal first-time home buying experiences, real-world lessons learned, and current market insights—including a surprising fact about the average age of today’s first-time home buyer.

If you’re thinking about buying your first home in 2026 or just starting to explore the idea, this episode will help you feel informed, confident, and ready to take the next step.

🎧 Listen now on YouTube, Apple Podcasts, and Spotify
🏡 Topics include: first-time home buyer tips, buyer agency explained, Madison WI housing market, and what to expect when buying your first home

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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In Episode 7, It’s Like That Madison goes on the road to one of our favorite neighborhood spots—Table Wine in the heart of the Atwood neighborhood—for a conversation that blends real estate, local flavor, and a little fun.

Join hosts Jannea, Tiffany, and Katie alongside special guest Molly Moran, wine expert/owner of Table Wine, as we ask a question you didn’t know you needed answered:
If a style of house were a wine, what kind of wine would it be?

Together, we take eight popular Wisconsin house styles—from timeless classics to more modern favorites—and pair each one with a type of wine that matches its personality, vibe, and appeal. Along the way, we sip, taste, and talk through why certain homes feel bold, approachable, refined, or full of character—just like a great bottle of wine.

This episode is equal parts entertaining and insightful, offering a fresh perspective on architecture, design, and how we connect emotionally to the homes we love—all while supporting a fantastic local business.

Whether you’re a wine lover, a real estate enthusiast, or just here for a good conversation, this episode is guaranteed to be a fun pour.

🎧 Tune in, grab a glass, and join us at Table Wine for Episode 7.

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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Are you considering a move to Madison, Wisconsin? In this episode of It’s Like That Madison, we walk through the biggest pros, cons, and surprises of relocating to the Madison area.

What we cover in this episode:
• The reality of long Wisconsin winters
• Higher cost of living, rising rents, and home prices
• Property taxes - some of the highest in the Midwest
• The limitations of public transportation
• Madison’s strong job market & low unemployment
• The resilience of the local housing market
• Unique, charming neighborhoods and communities
• Endless fun things to do — outdoor activities, food, festivals & more

Whether you’re planning a move or just curious about Madison life, this episode gives you a clear, honest look at what to expect — and why so many people end up loving it here.

Catch our previous episodes for deep dives on nearby communities, fun things to do, and insider local tips. It’s Like That Madison — Real life. Real estate. Real Madison.

Don’t forget to like, subscribe, and hit the bell for new 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/

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Join us today for Its Like That Madison Episode 5 where we explore two Madison suburbs with Norwegian heritage, cute downtowns, fun activities, and beautiful county parks. We dive into average prices for homes in Stoughton and Mt. Horeb and whether you get more bang for your buck, their cultural and lifestyle offerings, and of course we have to give a shout out to a couple of the best haunted houses in the area for Halloween!

For our November episode, we'll be taking it on the road to a locally owned business for a fun conversation. Stay tuned to find out where!

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/