Wealth management for senior executives who change employers
John Montgomery
Daily emails. Sometimes great. Always honest.
The daily emails
A short email most weekdays. Money is the main subject. So are decisions, work, life, and whatever else is on my mind that morning.
They're written by John Montgomery, a financial advisor who's been at it for about 15 years. The day job is what gives the emails substance. The emails are what makes the day job interesting.
No paywall. Just emails. Sometimes great. Always honest.
Recent emails
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Juicy red fruit and American Football
September 3, 2026
The humble watermelon. Possibly my favorite of all the fruits. I was eating some for lunch yesterday and I thought… Where do watermelons come from? A quick Wikipedia page later… Apparently its origins are in Sudan and...
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Honest Abe and a weeping Jesus
August 26, 2026
A few years back I was reading this great little book by a fella named Andrew Peterson. Peterson's prolific. He's a singer-songwriter. He's written non-fiction. And he's probably most famous for his YA fantasy series....
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Dog runs and headboards
August 24, 2026
There's a meme floating around online… "You can just do things." Or something to that effect. It is a bit tiresome at times. And it's certainly been co-opted by hustle bros and the like. You know… hustle for hustle's ...
If you want to work with me directly
Some readers want help with their actual money, not just the daily writing. I take a few new clients each year. They're senior executives who move every few years and end up with pay scattered across three employers.
I grew up the son of a health system CEO. I watched my father carry the weight of an entire organization home every night, his own affairs always coming last. That's not a niche I picked off a spreadsheet, it's the world I came from, and it's still where I do my deepest work.
Here's the gap I fill. Most advisors manage the portfolio and never open a plan document. I read the plan documents. The elections, the vesting, the payout timing, the change-in-control language. I handle both sides.
If you've ever wondered, quietly, when you could actually be done... that's the question all of this exists to answer.
The front door
The 90-Day Compensation Review
For senior executives who have recently changed employers: I deliver a written analysis covering every retirement account, deferred compensation plan, and equity arrangement across your current and past employers.
Most of the decisions that cannot be undone happen in the first 90 days. This analysis is designed to be completed before those windows close.
Nobody has ever read these documents back to you. This is that.
$2,500 · delivered within three weeks of receiving your documents
- What each plan is worth today
- What elections or rollover windows have hard deadlines
- What your previous seat is still holding that belongs to you
- What a move in the wrong order would cost, permanently
- A 90-minute walkthrough session
If after reviewing the analysis you don't find it valuable, I won't invoice you.
Ongoing
The Personal CFO
Greater of $7,500 a year, or 1.5% on the first $1M and 1% above · everything included
- First 90 days: your complete written plan
- Your decision calendar, built and watched
- Every agreed move implemented, and your CPA and I on the same page
- At the end of year one you continue, or you walk with everything we built
Started with the Review? The $2,500 credits in full.
No products, no commissions. That's the whole model.