My view as I write this newsletter this morning… Eh, not bad. Where’s the grey skies and leafless trees?

We are down in Bonita Beach, Florida these two weeks our annual winter hiatus. As much as one can love a charming midwest city like Indianapolis, there comes a point when the winter lull sets in and you have had enough of biting cold, overcast skies, and colorless scenery.

It is around this time, the past 3 years, that we have packed our bags and come down to live, work, and play on the Gulf Coast of Florida. This week we are here for a total of 16 days, staying in 3 different Airbnb’s. Fortunately, we have extended family down here (they decided to escape the cold for forever and relocate), so it’s also a reunion of sorts.

I think more and more about rhythms, especially now that I am a father. As the writer of Ecclesiastes says…

We have embraced this fully. There is a time for everything. The year is bifurcated perfectly to do that — the seasons we experience in the Midwest (and in real estate).

So what are these rhythms, you might ask? We’ll it’s not perfect, but it’s supposed to go something like this:

January: I like to hit the pavement, embrace discomfort: cold showers, hit the gym, run outside in sub-0 temps, dry January. In fact, I did all of these things last month!

February: We retreat to Florida to see extended family, we are renewed in the warmth. I set strategical path for the year, while away. I think clearly about what the year is to mean.

March-April: I refocus and re-gear as I enter the busy-season of real estate in Indianapolis.

May: This is it. The best month in Indianapolis. We run the Indy Mini (13.1 miles) and go watch obscenely fast cars at the track on Memorial Day weekend. Summer is back!

June: This is peak month for biz. Lots of contracts & closings. Embracing that early Summer energy.

July: Summer lull sets in. It’s sticky, it’s uncomfortable, it’s hot. The State Fair comes to town — so you know it’s 90+ and humid. We escape a lot up north to Michigan this month… frigid lake waters… ah, yes.

August: Wind-down mode approaches. We escape for even longer stretches to Michigan, recovering from the hectic summer months of real estate.

September: A brief second humph of real estate transactions post-Labor day. Summers last stand. A glorious month in Indy.

October-November: This is the retreat inward, to family, back into the warmth of the home. Business falls in priorities — the wins have been collected this year — time to finish it up.

December: Christmastime! I’ll do a year-review with my partner, and we set goals for the next year. A month of reflection.

I’ll ask you… What are your rhythms?

As my coach reminded me last week — There are “push seasons” and “pull seasons”. We are not infinite beings, we are finite. We require rest, Sabbath, retreat, refocus, and renewal. Are you sprinkling these times in through the year to preserve your strength and stamina?

Florida was one of those states that actually saw a pretty potent correction in the last few years. Unlike in Indianapolis and most of the Midwest, Florida did see a massive spike in inventory (under 40K homes in early 2022 to over 180,000 in early 2025 (that’s 9x folks…!), coinciding with shrinking prices and unthinkable days on market. My grandparents listed their home in Naples for $900K. They sold it last month in the $500’s….

What goes up must go down? Not so much in the Midwest, like Indiana, but yes, quite common in the bubble markets like South Florida.

Florida is up for sale right now, although we are seeing things stabilize. Moderate rates and prices falling to reasonable levels helps…

I talked to a guy at the beach yesterday. He sold his condo last year (2025). The taxes, the insurance, and the HOA costs have all grown substantially. Hurricanes. These will eff your housing market up, let me tell you.

The market for insurance down here is changing fast. Will there be more innovated products? I hope so… Right now there’s a lot unknown. Recently there was a boom back to renting here. Why own when you can rent and not have the liability and overhead?

This is the beauty of the market. It corrects. Prices eased down, making it more sense for folks to buy. Florida is not going anywhere. 12 months of warmth and white sandy beaches is too valuable. And right now, if you’re looking to buy, now is the window: There are 8 listings for every 1 in 2022. This won’t last forever.

PS— We know some great agents down here. I’d love to make a referral if you’re looking to buy in any part of the country. Our network of rockstar agents is growing!

These are all hand-picked properties that myself or our team has off-market, pre-market or coming-soon!

If even slightly interested, shoot me a response and we can chat about the details of these!

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