Happy New Year.

Crazy to think it’s already 2026. It’s been nice to spend some time the last week of the year to decompress with family and friends. My wife and I spent last weekend in northwoods Wisconsin with her family for Christmas; chatting around the fire, riding snowmobiles, playing Euchre. Then we came back to Chicago to spend New Year’s Eve with friends at a piano bar (a lovely dichotomy).

And as 2025 closes I have mixed feelings. It was both a huge exciting year and a bit of a disappointment. I sold my first business Uptrends.ai in May, launched my second venture Babbl Labs in June, raised $$$ from VC’s, brought on seasoned advisors, and closed our first partnership deal worth >$30K in December, all while teaching startup night classes online via ILT Academy. It was our first full year in Chicago, we made great new friends, I moved into coworking office, the city really feels like home.

It sounds great, and it is. I remind myself that I really am proud of it. But it also isn’t quite what I’d hoped for. While the Uptrends sale is signed, the technical handoff is still ongoing and it feels unlikely we’ll make much from it (other than a little street cred). For Babbl Labs, we came up $100K short of our fundraising goal, haven’t been able to close the big hedge funds deals we thought would be our big ticket, and have under 6 months runway in the bank. Feels a bit like my back is against the wall heading into the new year. There’s a heads and a tails to every tale.

As I look a head, I wonder if I’m putting too much stake in my business. Or maybe my expectations just weren’t quite realistic. My business is my entire life today, so of course when things are off course your mental state pays more for it. I think about friends with cushy consulting jobs, salary, benefits, and 3 weeks paid leave; it sounds like a nice reprieve but I know deep down it’s not what I want. What I want more than anything is to build a sustainable business.

But maybe a new hobby or side hustle would be nice – a creative outlet to take some pressure off my all-encompassing business. I think that’s one of my resolutions for 2026. The rest of my goals this year are the typical ones. Be healthier, get wealthier, become wiser. I really want to learn how to wake up to my first alarm every morning. I want to be able to bench 205lb + squat 315lb + deadlift 405lb by the end of the year. I want to get rid of my TV and read more books.

Maybe I will join a band or try painting or pottery. Or maybe a digital hobby that can make me extra income, something like an Instagram meme account or something I’m good at like writing or designing landing pages or doing GTM engineering for startups. Overall I guess I’d like to be more curious this year. Spend more time learning and trying and meeting new friends and diversifying my talents while I’m still in my twenties.

And speaking of diversifying, I also want to get a financial advisor and set the table for us to settle down and buy a house by 2030. That sounds nice, though I’m quite sure where we’d look yet (2030 feels so far away today).

So for now cheers to 2026 — to curiosity, to growth, to growing up, to trying, to missing, to setting big expectations anyways. To sharing and to caring. If there is one thing I hope for anyone reading this, is that you will take care too this year.

Take care,
Ramsey