It's Like That Madison, WI

About It's Like That Madison, WI

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.

Publisher

It's Like That Madison, WI

Category

education · leisure · society & culture

Language

en

Explicit

No

First episode

5 Aug 2025

Latest episode

30 Sept 2026

Latest episodes

15 episodes in the feed.

1. 

   30 Sept 2026

   Episode 15: The Dating Game ... Madison Suburbs Edition

   Send us Fan Mail The Dating Game… Madison Suburbs Edition! 🏡❤️ What happens when a Madison-area homebuyer has to choose their perfect suburb without knowing which suburb they’re choosing? In this episode of It’s Like That Madison, we’re putting a real estate twist on the classic Dating Game. Our buyer meets three mystery Madison suburbs and asks each “contestant” questions about lifestyle, personality, housing, things to do, and what makes them a great match. The catch? The suburbs don’t reve...

2. 

   11 Sept 2026

   Episode 14: Exploring Waunakee & Sun Prairie

   Send us Fan Mail 🎙️ Episode 14: Exploring Waunakee & Sun Prairie, Wisconsin Thinking about living outside Madison but still want easy access to everything the city has to offer? In Episode 14 of It’s Like That Madison, we’re heading just outside the city to explore two of Dane County’s most popular communities: Waunakee and Sun Prairie. Join Realtors Jannea Wood, Tiffany Tobias, and Katie Kolakowski as we compare what it’s like to live in Waunakee vs. Sun Prairie — from housing and home p...

3. 

   31 Jul 2026

   Episode 13: If Madison Neighborhoods Were Dogs

   Send us Fan Mail If Madison neighborhoods were dogs... what breed would they be? In Episode 13 of It's Like That Madison, Jannea Wood, Tiffany Tobias, and Katie Kolakowski put a playful twist on exploring Madison by matching some of the city's best-known neighborhoods with the dog breeds that capture their personalities. The hosts reveal their picks for: • SASY (Schenk-Atwood-Starkweather-Yahara) • Vilas / Dudgeon-Monroe • Meadowood / Raymond • Cherokee / Sherman Park ...

4. 

   6 Jun 2026

   Episode 12: So You Thinking About Investment Properties?

   Send us Fan Mail 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...

5. 

   22 Apr 2026

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

   Send us Fan Mail 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 compet...

6. 

   20 Mar 2026

   Episode 10: How It All Started + Celebrating 10 Episodes! I It's Like That Madison Podcast

   Send us Fan Mail 🎉 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 w...

7. 

   28 Feb 2026

   Episode 9: Home Inspections - The Good, The Bad, & The Ugly

   Send us Fan Mail 🏠 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...

8. 

   28 Jan 2026

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

   Send us Fan Mail 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 wor...

9. 

   21 Dec 2025

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

   Send us Fan Mail 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 pop...

10. 

    21 Nov 2025

    Episode 6: Moving to Madison Wisconsin: What You Need to Know - Pros, Cons, and Cost of Living

    Send us Fan Mail 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...

11. 

    3 Oct 2025

    Episode 5: A Closer Look at Stoughton & Mt. Horeb - Charming Downtowns, County Parks, & Haunted Houses!

    Send us Fan Mail 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 t...

12. 

    6 Sept 2025

    Episode 4: Real Life Real Estate versus Reality TV Real Estate

    Send us Fan Mail 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 heri...

13. 

    13 Aug 2025

    Episode 3: Madison Food Scene & When Is The Best Time to Sell?

    Send us Fan Mail 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 re...

14. 

    6 Aug 2025

    Episode 2: Fun Things To Do In The Summer Around Madison

    Send us Fan Mail 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 ...

15. 

    5 Aug 2025

    Episode 1: Real Estate: Dogs, Dogs, (some cats) and more Dogs.

    Send us Fan Mail 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 discus...

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

4.0 / 5

4 ratings

Spotify

5.0 / 5

1 ratings