SSS #323: Best & Worst of 2025

Livin' La Vida Luna y Luca

How many times can one family have breakfast with Santa?

Best & Worst of 2025

As 2025 draws to a close, it's time to pause and reflect on the highs, lows, and everything in between. This past year was a whirlwind of growth, experiments, and a few (not so) hard lessons. Here's an unfiltered take on the best and worst of what shaped my 2025.

Let's dive in!

👍 Best Decision - New Home

We bought our first home this year. We've never really lived in a place with "extra space". Now we have an extra bedroom and bathroom. I did not realize how much I'd enjoy hosting friends and family from out of town.

The Jury is still out on all the maintenance and endless customizations, but I can confidently say I'm glad Dia pushed me into this decision... for now.

👎 Worst Decision - Investing in Philadelphia

I didn't make any new investments in Philadelphia in 2025, but the purchases I made in the 2 years prior spent all of 2025 proving to me the results will be mediocre at best.

👍 Best Investment - FZROX

I'm a simple man when it comes to investing. Most of our money is tied up in FZROX. It's up ~16% YTD.

I don't consider the development deals "investments" as they're more like widgets (COGS) in my business.

👎 Worst Investment - Crypto

My Coinbase account is only up 2.5% YTD. It was up ~40% in October. What the heck did Trump say again?

👍 Best Purchase - REconvene

I went all the way to Santa Monica, CA to attend my first real estate conference since 2019.

I liked it so much I already booked my ticket for 2026.

👎 Worst Purchase -

I don't really buy things, so I'm struggling to think of any one thing for this category.

I will say, however, that anytime we've tried to save money by buying a sub-par version of something, we instantly regretted it.

What's the saying? "They don't make 'em like they used to..."

So cliché, but so true. Nothing is built to last anymore.

👍 Best Book(s) 📚

These 2 books are oddly connected. Andre Agassi's dad worked for Kirk Kerkorian as a Captain in one of his casinos. Andre's middle name is Kirk.

👎 Worst Book

The Courage to Be Disliked: The Japanese Phenomenon That Shows You How to Change Your Life and Achieve Real Happiness

I really wanted to like this book, but I couldn't get into the format. It's written as a conversation between a wise old man and a young, naive student.

It was kind of like reading a script of a really boring movie. I'm sure there were some gems, but I put the book down after 2 or 3 chapters.

👍 Best Podcast - Costco by Acquired

If you love Costco and have 3 hours to spare, LISTEN TO THIS PODCAST! I loved learning about the history of Costco. The first half of the podcast was about the decades leading up to Costco's founding. They spent less than 15 minutes on Costco's business as it stands today.

They went SUPER deep into the weeds. Fascinating stuff, truly.

👎 Worst Podcast - Money For Couples by Ramit

I really like Ramit, and I wanted to like his new podcast, but I had to tap out after a few episodes. Ramit is a saint. The restraint, patience, and empathy he shows to these couples who make countless "mistakes" with their money is incredible to watch.

With that said, I will not be listening anymore.

👍 Best Advice - Say No to Good Ideas

Steve Jobs said:

People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I’m actually as proud of the things we haven’t done as the things I have done. Innovation is saying ‘no’ to 1,000 things.

My business took off like a rocket ship after I said, "No" to everything else.

👎 Worst Advice - Slow Down

We see my parents every Sunday. There was a season where it seemed like every time they asked me about work, I was telling them about another potential acquisition.

One day, my mom suggested I slow down...

I did not listen. 😅

👍 Best Experiment - Walking More

10K Steps / Day in June '25 was difficult, but I think I'm going to make 10k/day a thing in 2026. Walking is just so enjoyable and easy.

👎 Worst Experiment - Direct Mail in NY

I tried to expand my direct mail marketing efforts in NY and fell flat on my face. I spent ~$10K on mail, and the phone barely rang. I half-heartedly sent 1 offer.

Acquiring leads through direct mail is getting trickier and more expensive. I have no business trying to do it from such a distance.

👍 Best Habit - Personal Finance Tracking

We've been using Copilot for years now, but I still saw a meaningful change in the way we spent money in 2025. I'll likely do a full breakdown of how we spent our money in a few weeks, so stay tuned for that.

👎 Worst Habit - Social Media

Thankfully, I've never had TikTok, and I removed IG from my phone a while ago.

More recently, I got rid of X and YouTube as well. There's no more social media apps on my phone.

It got to the point where I would pull out my phone to check X while I was filling my water cup. WTF?! 🤦🏽‍♂️

The goal is to keep all social media apps off my phone for all of 2026. Let's see how it goes.

✌🏽 Wrapped

As I wrap up the year, one truth shines: growth comes from bold risks, learning from flops, and smart pivots. 2025's highs fueled my focus, while the lows taught humility. After doubling down on winners (like FZROX) and cutting distractions (social media), I'm ready for 2026. 💪🏽

What are some of your takeaways from 2025?

Hit reply and LMK!

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