Newsletter
Read time: 5 minutes
Welcome to the 22nd edition of the Tech Financial Planning (TFP) newsletter.
As we enter tax season, there’s an easy mistake that can cost tech professionals big time.
The dreaded double tax on their stock compensation.
In this newsletter we’ll break down what the double tax is, how it happens, and how to avoid it.
Read time: 4 minutes
“To be a successful investor, you’ve got to be an optimist. You have to believe in the innovations that come from the human mind and the human spirit.”
Charles Schwab
As we come off a rough 2022 for markets, it’s easy to be pessimistic.
The headlines are almost all bad news
Experts predict a recession
Companies are laying people off
Inflation is still high
Home prices are dropping
And so forth.
I’d like to use this newsletter as a measured case for optimism.
First and foremost, I believe we live in the greatest time in human history.
“If you have no idea how much is enough, you’ll never be satisfied with what you have.”
-Ben Carlson
I met with an employee of a publicly traded tech company earlier this year.
Over the past few years, the value of their company stock soared, and at the beginning of this year it was worth over $6 million.
But their company stock has been crushed this year and they never sold.
The value of those shares today is less than $1 million.
Today’s newsletter is something my dad wrote over 10 years ago.
It’s a topic I’ve thought a lot about recently, both in my life and in the families I work with - how as we earn more, we spend more.
In financial planning, we call this lifestyle creep.
While my dad is in commercial real estate, a lot of the same lessons apply to people in tech.
I’ll let my dad take it from here.
Welcome to the 16th edition of the Tech Financial Planning (TFP) newsletter.
I wrote last week about my two favorite ways for tech employees to get free money.
One of them is your company ESPP, and this week is a great case study of how ESPP’s can work in your favor.
Procore employee’s just got a whopping 44.1% return on their most recent ESPP purchase
Let’s dive in
Welcome to the 15th edition of the Tech Financial Planning (TFP) newsletter.
In this week’s issue, I want to share my 2 favorite ways for tech professionals to get “free” money from their company.
No, this isn’t anything crazy, sketchy, or illegal.
In this newsletter, we’ll break down 401k matching and ESPP programs, and why these can be two of the biggest no-brainers for tech professionals.
Welcome to the 14th edition of the Tech Financial Planning (TFP) newsletter.
When you have a lot of company stock, you also usually have significant gains.
Which means if you sell, you will likely pay a lot in capital gains.
But done correctly, you can “hack” your way to diversification and little to no taxes.
In this newsletter, we will break down why you might consider selling more company stock by the end of the year and how to not get killed on taxes.
Welcome to the 13th edition of the Tech Financial Planning (TFP) Newsletter.
If you joined Procore in ~2016, received 100k stock options, and exercised them all, you would take home $3.77M after taxes if you sold everything today.
But if you waited until Procore was public to exercise and sell (for argument’s sake, let's also say today) you’d take home $2.87M – a difference of $896,680.
Let’s break it down.
In this newsletter we will break down why you might consider exercising your options before an exit, the potential tax savings, and the risks
Welcome to the 11th edition of the Tech Financial Planning (TFP) Newsletter.
Unsurprisingly, one of the top questions I’ve been asked this year is “should we make changes to the plan?”
With most investors getting hammered, people want to know what they should do.
In this newsletter, we will break down when you should make changes to your plan and when you shouldn't.
Welcome to the 11th edition of the Tech Financial Planning (TFP) Newsletter.
At this point, everyone is pretty aware that interest rates have gone up a ton this year.
There’s certainly been some downsides, like mortgage rates skyrocketing.
But one positive is that there is finally a chance to earn some money on your cash.
In this newsletter we will break down 3 opportunities for your cash, so you can make more money.
Welcome to the 10th edition of the Tech Financial Planning (TFP) Newsletter.
Back in August, I had a 1:1 call with a new client who reached out because she just got a new job with a big increase in total compensation.
Emily (not her real name), is a product marketer at a large tech company and is set to earn just over $400,000 this year.
In this newsletter we will break down the 3 challenges Emily was facing and how we solved them together.
Welcome to the 9th edition of the Tech Financial Planning (TFP) Newsletter
So you have a big chunk of money in your company stock.
Through hard work, good fortune, and some solid equity awards, you’ve built up a nice nest egg.
You’ve done well for yourself, so why should you sell (hint - the Titanic was supposed to be unsinkable)?
In this newsletter we will go over the real risk of concentrated positions, how to think about holding one, and some thoughts on selling.
Welcome to the 8th edition of the Tech Financial Planning (TFP) Newsletter.
It goes without saying, this hasn’t been a great year for the stock market.
Interest rates are up, investors are scared, and no one is really sure what the next few months hold.
Have we hit the bottom? Are we in a recession? What should we be doing?
In this newsletter we’ll cover why down markets are some of the best times to invest, some tangible steps you can take, and what not to do.
Welcome to the 7th edition of the Tech Financial Planning (TFP) Newsletter.
What are you working for?
And what are you saving & investing for?
These aren’t trick questions.
In this newsletter we will take a detour from our normal planning topics and focus on some ways of thinking about goals and dreams.
Welcome to the 6th edition of the Tech Financial Planning (TFP) Newsletter.
I was talking with someone on Linkedin and they were asking about getting RSUs at a private company.
How the heck does that work exactly?
Hello double-trigger RSUs
In this newsletter we will go over what double-trigger RSUs are, how they differ from “traditional” RSUs, and some important considerations.
So you just had some RSUs vest.
Should you sell and diversify or hold onto the stock (diamond hands - to the moon!)?
Enter the great financial planning mantra of “It depends.”
In this article we will go over some important considerations for your RSUs, some reasons you might diversify, and some reasons you might hold.
