This is the first issue of my monthly newsletter, originally sent to subscribers on May 27, 2026.
I’m going to be real with you
Today was my first day of my post-W2 life.
From the outside, the decision to leave is questionable at best. Voluntarily leaving a role with a lot of autonomy and influence, good pay and a principal title, at a well-respected company that is a leader in a hot space right now. And it’s a great place to work.
I’m going to miss my coworkers, many of whom have become real friends. I’m going to miss the intellectual stimulation of trying to influence a large engineering culture over time. I’m going to miss the dopamine hits of helping other engineers get unblocked. I’m going to miss laughing constantly while working together with people I respect. This company has been my main social outlet - Slack chats and Zoom calls my daily existence - for the past 8.5 years.
So why leave a company where I feel valued and respected, and where I genuinely enjoy working?
I’m keeping a promise that I made to myself in 2014.
From 2013-2015, I was obsessed with Mr. Money Mustache (MMM). Reading First Retire, Then Have Kids opened my mind to the possibility of “retiring” so early that I would be fully present for their entire lives. This became my driving WHY for Financial Independence, Retire Early (FIRE), a goal that I single-mindedly pursued for the next decade.
I achieved the “FI” part in 2021 when my company IPO’d. We had our first child in late 2023. However, “RE” didn’t come until 2026. With the IBM acquisition removing my ability to “slow travel” nomadically with my family, I’d finally run out of excuses for postponing.
What are we doing here?
This is where you come in. I don’t really know what’s next, other than I’ve committed to sharing my journey with you as I go. I’m hoping that you can help me figure it out. No pressure. 😊
Here’s what I know so far:
- I love helping people with personal finance and want more opportunities to do this.
- Investing has been my main hobby since 2015. It runs the gamut from deep value equities, to multifamily real estate, to niche small businesses.
- Last year, a business partner and I raised our first real estate syndication. Surprising myself, I really enjoyed the experience of reaching out to friends and coworkers on this deal. Turns out that it’s fun to make money together with people you like.
- Later last year, I helped a couple folks co-invest with me in a 30-year old hardscaping company acquisition. I may also help someone co-invest with me in a niche industrial manufacturing company acquisition that’s closing soon.
Besides… I’m going to be looking at deals for my own portfolio anyway. So why not share? Better yet, I’m structuring my investments so I can learn alongside the operators, so why not share these takeaways as well?
What would you like from me? What can I help with?
📚 What I’ve read recently
The Good Enough Job: Reclaiming Life from Work — Makes a good case that a lot of things we (white collar workers) like about work are actually bad for us (e.g., feeling like a family, excessive perks). But it basically encouraged worker apathy, which I struggle to accept.
The Golem and the Jinni — Fun mash-up of historical fiction, fantasy, and magical realism. It’s primarily set in modern day NYC with strong Jewish and Syrian influences (and flashbacks).
The Perfect Day Formula: How to Own the Day & Control Your Life — Written by the author of the Early To Rise blog, you can guess the main point: get up super early and do a bunch of work before anyone else is online. His personal schedule has 12 hour days: not exactly “control your life” inspiration. He does exercise mid-day though, to protect morning energy for his most important task; this is a takeaway I’m considering for my own life.
The Count of Monte Cristo — Amazing action-adventure novel. It’s got a fancy French title and is considered “literature,” but don’t let that stop you. It’s a rags-to-riches story of lost love and a long-plotted revenge.
The Preparation: How To Become Competent, Confident, and Dangerous — Skip over Doug Casey’s philosophical diatribes and just read the curriculum from Matt and Maxim Smith. It sounds like experiences I’d love to have even as an adult. I’m going to figure out how to fold this learning approach into my overall intentional life design.
The Explorer’s Gene: Why We Seek Big Challenges, New Flavors, and the Blank Spots on the Map – How Neuroscience and Behavioral Psychology Explain Our Primal Urge to Explore — 5 star review if you like neuroscience (Huberman-esque). The explore-exploit tension is a keep-worthy mental model. Practical advice to stop your hippocampus from shrinking.
Tiny Experiments: How to Live Freely in a Goal-Obsessed World — Not very engaging, but what I needed at this time. Helped me reorient as I go from “exploit” to “explore” — switch from trying to “start at end and work backward” and instead make a series of small bets to explore my options for now. It encourages “learning in public” which directly led me to making this monthly letter to you all.