taxes

TFP #057: Navigating Your E-Trade Account: A Guide For Procore Employees

I get a lot of questions about trying to understand your equity at E-Trade, which is fair. It’s very confusing. Words like potential value, current value, total value - it’s not super clear. And some views are helpful, and some aren’t.

So candidly, I don’t use the website until it’s time to sell or exercise. When I work with clients, I have them send me this CSV (you can get it by logging in to E-Trade, then select your Stock plan, go to "holdings", then "view by status", "download", "download expanded".)

Today I want to walk you through what I look for and the flow I go through. At a high level, this report tells me 3 really important things about your equity.

  1. What you have already

  2. What you are able to exercise

  3. What is unvested

TFP #055: 9 Ways To Manage Your Company Stock

There’s only 3 ways to approach your company stock:

  • Sell none of it

  • Sell some of it

  • Sell all of it

But there can be variations - particularly if you are looking to sell some.

Let’s run through 9 of the most common ways to manage your company stock, and we’ll include an example for each one.

For simplicity’s sake, let’s say you hold 10,000 shares of XYZ company, and XYZ company currently trades at $50 / share.

Which means you currently have $500,000 worth of XYZ stock.

TFP #053: Don't Tip The IRS

Read Time: 3 minutes

Welcome to the 53rd edition of the Tech Financial Planning (TFP) newsletter.

If you have company stock, please, please, pretty please, make sure you report the correct cost basis.

It can be the difference between owing $7,000 and owing $10 (aka tipping the IRS).

I was chatting with someone earlier this week on LinkedIn and they were doing their taxes in TurboTax and they were surprised with how much taxes they still owed.

TFP #051: Should You Participate In Your Company’s Tender Offer?

Read Time: 5 minutes

Welcome to the 51st edition of the Tech Financial Planning (TFP) newsletter.

When you work at a private company, the big dream for most is that your company goes IPO one day.

And while IPOs often grab headlines, it’s not the only way that you can turn your private company stock into cash.

The past few months we’ve helped several clients at two different private companies evaluate tender offers.

Tender offers are “a structured liquidity event that typically allows multiple sellers (including employees and early investors) to sell their shares either to another investor, a group of investors, or back to the company at a predetermined price. 

In other words, it’s a potential way for employees to sell their shares for cash while the company is still private”

TFP #049: How We Work With Clients

Read Time: 2 Minutes

Welcome to the 49th edition of the Tech Financial Planning (TFP) newsletter.

My typical client looks like this:

  • Tech employee with equity comp

  • Household income of $350k+ (potentially more once you factor in equity comp)

  • Good chance current / former Procore

  • Usually 1-2 kids (or planning on it) and probably a dog

  • High cost of living

  • Looking for someone to help them navigate all the complex planning that comes up.

Here are the 6 areas we cover for clients.

TFP #047: It's Ok To Pay Taxes

Read Time: 4.5 Minutes

Welcome to the 47th edition of the Tech Financial Planning (TFP) newsletter

Everyone feels like they are paying too much in taxes.

A common pain point: 

“We are getting killed in taxes. 

We make $300k-$500k+ as a W2 household and we routinely pay 5 to 6 figures in taxes every year. 

What can we do?

Unfortunately, there’s no magic wand that you can waive to make your taxes go away.

Spoiler alert: sometimes it’s ok to bite the bullet and pay the taxes.

Because saving (or deferring) taxes almost always comes at some sort of cost.

It’s usually costs you one of two things

  1. Access

  2. Less money in your pocket today

TFP #043: How Is Financial Planning Different For Tech Employees?

Read Time: 5 Minutes

Welcome to the 43rd edition of the Tech Financial Planning (TFP) Newsletter.

What on earth is financial planning, and how is it unique for people in tech?

Or put more simply, what is it that we actually do with clients?

In this newsletter we’ll break down what financial planning is, both broadly and for our clients, and some ways we’ve helped clients this year.

TFP #040: 5 Ideas to Save Taxes With Your RSUs

Read Time: 4 minutes

Welcome to the 40th edition of the Tech Financial Planning (TFP) newsletter.

If you work at a public tech company, RSUs can represent a significant portion of your total compensation

While you can’t control the timing of when your RSUs are taxed, there are ways to use your RSUs to lower your total tax bill.

Either now or in the future.

In this newsletter we’ll break down 5 possible ways to use your RSUs to reduce taxes, run through an example, and importantly, consider when you don’t want to use these strategies.

TFP #039: 5 Money Myths

Read Time: 5 minutes

Welcome to the 39th edition of the Tech Financial Planning (TFP) newsletter.

Over the past few years of working with tech professionals, I’ve discovered a number of myths and half-truths that people believe.

And more importantly, they are driving people’s behavior around money.

In this newsletter, we’ll break down 5 common myths I have heard and why they aren’t true.

TFP #036: 2 Questions To Ask Yourself When Your RSUs Vest

Read Time: 5 minutes

Welcome to the 36th edition of the Tech Financial Planning (TFP) newsletter.

If you receive RSUs, you’ll need to decide what you will do when your shares vest.

Otherwise you may be sitting on a ticking (tax and financial) time bomb.

In this newsletter we’ll break down the 2 questions you should be asking yourself when your RSUs vest, plus 2 planning examples based on client scenarios we’ve worked through.

TFP #031: A Framework For Your Equity Comp

Welcome to the 31st edition of the Tech Financial Planning (TFP) newsletter.

If you Google “what to do with my equity compensation” you get 823 million results!

How the heck are you supposed to make a good, wise, financial decision?

Particularly if you are new to equity comp or have more complex situations? 

In this newsletter we’ll break down a framework for making decisions for your equity comp and review 3 specific scenarios with some real life examples.

TFP #029: 6 Financial Planning Mistakes Tech Professionals Make

Read Time: 3 minutes

Welcome to the 29th edition of the Tech Financial Planning (TFP) newsletter.

Over the past 3 years I’ve met with hundreds of tech professionals, and I’ve seen 6 common financial planning mistakes.

These can cost thousands or even millions of dollars.

In this newsletter, we will explore 6 common financial planning mistakes tech professionals make and some possible ways to avoid them.

TFP #022: Avoiding The "Double Tax" On Your Equity Comp

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.

TFP #014: A Year End "Hack" To Diversify Your Company Stock

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.

TFP #013: A Tale Of Two Strategies

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

TFP #010: 3 Steps To Fixing A New Client's Plan

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.