The Chicago coffee scene is HOT. My favorites to date.
- Big Shoulders Redeye
- Sawada Tokyo Style
- Discourse
- Metric
What am I missing and need to know.
Here’s something incredible about Chicago.
The food continues to be top tier and I’ve gotten reservations with little stress.
The best restaurant I enjoyed last week was Carmines.
A great discovery in Chicago…
The exclusive Sip & Guzzle pop up suite at the Four Seasons. Enjoyed the debut weekend concept bringing unique drinks from the #1 bar in North America to the city through March 2027.
Mile High Cocktail Club was memorable.
You won’t believe this.
It was another picturesque and glorious fall day in Chicago.
Fortunately it looks like the week ahead is more of the same. Elite city!
Spectacular Sunday for my first Open House Chicago. Here are my highlights.
- Chicago Architecture Center
- Chicago Loop Synagogue
- Columbia Yacht Club
- Federal Reserve Bank of Chicago / Money Museun
So far it’s a 10/10 schedule. Ask me anything.
What a feeling waking up early on a Fall Saturday morning to see an iconic skyline downtown.
Perfect weather. Beautiful buildings. Crisp air.
Chicago has elite vibes.
Chicago, what if I told you...
The happy wife happy life program has two exciting reservations this weekend.
- NY pop up arrives with a view
- Lebanese gastronomy
What if you told me what restaurants they are. Can you do it. 👀
The local Chicago coffee scene is a great exploration.
- Metric
- Hexe
- Discourse
- Sawada
- McDonalds
Still new yet these recent discoveries deserve the mention and a return visit. Ask me anything.
Underrated life advice: The bathroom tells you so much about the space you are in. The good and the bad. A clean wash room says so much without saying anything. A dirty wash room says everything giving you every reason to ask more questions.
Here’s something incredible about Chicago.
My Friday venture takes me downtown.
There’s literally a river running through the heart of the city. 🤯
I'm documenting this whole chapter in my free newsletter: the Chicago spots worth your time, the career rebuild, and what I'm learning along the way.
investrly.substack.com
Working from places like this is part of how I'm rebuilding my career in Chicago.
I write about all of it, from the spots to the moves, in my free newsletter.
investrly.substack.com
Incredibly I got married three weekends ago.
Incredible how fast the best moments in your life can become faded memories.
Thankful this moment with these men is immortalized in time.
The single greatest truth in life Is you can just do stuff. Everyone whose gotten anywhere had to start somewhere.
Some of the best local Chicago coffee shops are dropping in for the launch.
- Metric
- Hexe
- Hawa
- Sawada
- Sakrid
- Noble Fat
- Side Practice
Chicago is both hot and cold. You choose.













