It's Like That Madison, WI

It's Like That Madison, WI
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Welcome to It’s Like That Madison, the podcast that dives deep into Madison, Wisconsin’s real estate scene, lifestyle, and community stories. Hosted by local Realtor Jannea Wood and Tiffany Tobias of Stark Company Realtors, and Katie Kolakowski of City RE, each episode explores what it’s really like to live, work, and play in and around Dane County.From buying your first home to uncovering the best neighborhoods, restaurants, parks, and hidden gems, we blend expert insights with local flair. You’ll hear about market trends, homebuyer tips, lifestyle features, and candid conversations with the people shaping Madison’s vibrant community.Whether you’re a Madison local, a future homeowner, or just love learning about what makes this city tick, you’ll find real talk, laughter, and plenty of Midwest charm here.

Episodes

  1. Home Inspections - The Good, The Bad, & The Ugly

    3D AGO

    Home Inspections - The Good, The Bad, & The Ugly

    Send a text 🏠 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/

    22 min
  2. Episode 8 – What to Know When Buying Your First Home | It’s Like That Madison

    JAN 28

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

    Send a text 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/

    38 min
  3. Episode 7: If a House Style Were a Wine… What Kind of Wine Would It Be? 🍷🏡

    12/21/2025

    Episode 7: If a House Style Were a Wine… What Kind of Wine Would It Be? 🍷🏡

    Send a text 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/

    31 min

  4. 11/21/2025

    Moving to Madison Wisconsin: What You Need to Know - Pros, Cons, and Cost of Living

    Send a text 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/

    25 min

  5. 10/03/2025

    A Closer Look at Stoughton & Mt. Horeb - Charming Downtowns, County Parks, & Haunted Houses!

    Send a text 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/

    32 min

  6. 09/06/2025

    Real Life Real Estate versus Reality TV Real Estate

    Send a text Join us today for episode 4 where we look at real life real estate vs those reality real estate shows we all know and love. Do you really only look at 3 houses? Do you get a 150% return on a home improvement? Do we fight all the time with other agents? Tune in and find out. Email us if you want a copy of the NAR Remodeling Impact Report or the Cost v Value Report mentioned in this podcast. Next up on episode 5 in October - exploring the two Madison suburbs with Norwegian heritage, cute downtowns, and beautiful county parks. We'll dive into average prices and whether you get more bang for your buck, cultural and lifestyle offering, and of course we have to give a shout out to a couple of the best haunted houses in the area for Halloween! 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/

    28 min

  7. 08/13/2025

    Madison Food Scene & When Is The Best Time to Sell?

    Send a text Join us today for episode 3 where we answer the question: "When is the best time to sell?" & highlight one of the reasons that makes Madison such a great place to live - it's amazing food scene. Can eating out be considered a hobby? We think so.  We dive into cool outdoor dining options, those you can get to by boat, and of course a Summer favorite - ice cream! With so many choices, it's hard to decide, but Destination Madison put together a great list to use as a resource: https://www.visitmadison.com/blog/stories/post/your-guide-to-streateries-and-outdoor-dining-in-madison/ Next up on episode 4 - real life real estate vs those reality real estate shows we all know and love. Do you really only look at 3 houses? Do you get a 150% return on a home improvement? Do we fight all the time with other agents? Tune in and find out. 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/

    24 min

  8. 08/06/2025

    Fun Things To Do In The Summer Around Madison

    Send a text Join us today for episode 2 where we discuss appraisal vs assessment and pre-approval vs pre-qualification. Then stick around and listen as we talk about all the things you can do in and around Madison during nice weather.  We dive into some of our favorite activities which include all the places music is available, gardens to explore, hiking and biking trails, kayaking and burgers, and even log rolling! Next, join us for episode 3 where we discuss the question "when is the best time to list my home?" and get into one of the many reasons Madison is such a great place to live - it's amazing food scene. Hosted by: Jannea Wood and Tiffany Tobias of Stark Company Realtors  and Katie Kolakowski of City RE 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/

    21 min

  9. 08/05/2025

    Real Estate: Dogs, Dogs, (some cats) and more Dogs.

    Send a text Join us today for episode 1 where we talk about current market trends in Madison, Wisconsin real estate. What kind of percentage over list prices are our sellers seeing.  We also dive further into our one of our favorite topics - dogs. What we are seeing from our buyers when looking at the features that they want for their dogs and cats when purchasing a home.  Have you ever heard of the word barkitecture. You will today Next, join us for episode two where we discuss appraisal versus assessment and discuss some of our favorite things to do in Madison, Wisconsin in the summer. Hosted by: Jannea Wood and Tiffany Tobias of Stark Company Realtors  and Katie Kolakowski of City RE 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/

    19 min
  • 9 Episodes

Ratings & Reviews

3
out of 5
2 Ratings

About

Welcome to It’s Like That Madison, the podcast that dives deep into Madison, Wisconsin’s real estate scene, lifestyle, and community stories. Hosted by local Realtor Jannea Wood and Tiffany Tobias of Stark Company Realtors, and Katie Kolakowski of City RE, each episode explores what it’s really like to live, work, and play in and around Dane County.From buying your first home to uncovering the best neighborhoods, restaurants, parks, and hidden gems, we blend expert insights with local flair. You’ll hear about market trends, homebuyer tips, lifestyle features, and candid conversations with the people shaping Madison’s vibrant community.Whether you’re a Madison local, a future homeowner, or just love learning about what makes this city tick, you’ll find real talk, laughter, and plenty of Midwest charm here.

Information

  • Creator
    It's Like That Madison, WI
  • Years Active
    2025 - 2026
  • Episodes
    9
  • Rating
    Clean
  • Copyright
    © 2026 It's Like That Madison, WI
  • Show Website
    It's Like That Madison, WI