Personal CFO to top performers in tech & business @ Quadrant Capital • Ethics/Tax @ UCLA PFP • Planning. Equity Compensation. Investing. Tax. • Tweets≠Advice
Jul 8 • 26 tweets • 4 min read
Figma is going public 2 years after the failed Adobe acquisition.
If you work at a pre-IPO company, this thread is for you.
What to know about RSUs, options, lockups, taxes, and strategy...using Figma as a case study. ↓ ↓ ↓ 1. A quick refresher: What is an IPO?
An IPO (Initial Public Offering) is when a private company lists its shares on a public stock exchange (like the Nasdaq or NYSE).
This allows public investors to buy shares (and gives employees a potential path to liquidity).
Jul 3 • 16 tweets • 2 min read
I work with founders, startup employees, business owners, & professionals who have 7-8 figures of equity or investments.
They've worked for years or decades to get where they are.
I've compiled their stories for months and laid out the commonalities here ↓ ↓ ↓
Every week, I meet with people who’ve worked hard, taken risks, and now face a new challenge:
Managing and preserving significant wealth.
They are all around us (and much younger than you think)...
Jul 1 • 26 tweets • 3 min read
Meta just hired a dozen AI legends to help run their Superintelligence program.
Assume they’re each making $10M/year TC.
What do you do if you suddenly make that kind of money?
When I first read the headline, this is where my brain went immediately ↓ ↓ ↓
Everyone thinks they have money figured out until $10M TC shows up on their offer letter.
Let’s break down what someone earning $10M/year should do to protect, preserve, and grow wealth.
Jun 30 • 23 tweets • 4 min read
You are a founder who is in the process of being acquired.
Straightforward situation, but significant proceeds and potential capital gains implications.
You estimate that your potential tax from the transaction could approach $900,000 (no QSBS eligibility). ↓ ↓ ↓
This thread aims to provide a general overview of how capital gains tax works.
Capital gains are profits realized when you sell an asset, such as a stock, bond, or piece of real estate, for more than you paid for it.
Capital gains may be categorized as short-term or long-term.
Jun 24 • 24 tweets • 3 min read
Everyone thinks they have money figured out until a $10,000,000 wire lands in their checking account.
Imagine joining a startup as a very early developer on a small team.
Ten-plus years later, the company was worth over $60B, and your equity was worth $17M. ↓ ↓ ↓
During a company-sponsored tender offer, someone in this position decides to cash out 85% of their equity.
That results in a $10 million windfall...after tax and exercise.
Oh, and you're only 30 years old.
Life changes forever. And naturally, three main questions emerge:
Jun 23 • 21 tweets • 5 min read
What should people consider when they receive a job offer with equity?
But you also have to UNDERSTAND how equity works. Bookmark this if you want to know more about equity than anyone you know ↓ ↓ ↓
One of the least commonly understood aspects of startups is equity.
Your comp is made up of several factors: salary, benefits, bonuses, and equity.
Equity *can be*your largest driver of comp.
(Note that I didn't say *will be*. The majority of equity = $0.)
Jun 22 • 26 tweets • 3 min read
It’s estimated that there are approximately 29.2M "forgotten" 401(k)s holding as much as $1.65T.
Changing jobs is stressful, & dealing with the admin of retirement plans gets pushed to the back burner.
So what can you do with an old 401(k)? And how does it work? ↓ ↓ ↓
In many situations, it can be beneficial to roll over a former employer retirement plan (e.g., 401(k), 403(b), 401(a), 457(b), TSP) into an IRA or a new employer’s plan.
However, this is not always the best decision for everyone.
Jun 21 • 20 tweets • 3 min read
Imagine having 25K options & 6K common shares of a public company.
At a current price of ~$295/sh, that’s $8.5M of equity value.
Most of it was received when the 409A was $22/sh (!).
It's been a heck of a ride since going public, and it might be time to take profits ↓ ↓ ↓
When the largest U.S. cryptocurrency exchange went public in a direct listing in 2021, the reference price was set at $250 per share.
Jun 20 • 21 tweets • 3 min read
An early-stage employee at Blue Apron was granted Incentive Stock Options (ISOs) when the company was just getting off the ground.
Years later, the strategy around their equity compensation didn’t play out as expected.
Their IPO was a disaster for equity holders. ↓ ↓ ↓
This is a cautionary tale about how timing, taxes, and market realities can impact the value of stock options.
Much has been said about the potential upside of startup equity.
But outcomes vary widely:
Jun 18 • 36 tweets • 5 min read
When "I don't know what I don't know" could cost you hundreds of thousands (or millions) in missed tax savings.
I'm talking about Qualified Small Business Stock (QSBS).
QSBS can mean tax-free capital gains from the sale of stock, up to $10. million. dollars. ↓ ↓ ↓
If you think this is a fantasy tax loophole and never happens in real life, think again.
(It’s actually somewhat common among founders and early employees of tech startups.)
Jun 13 • 19 tweets • 4 min read
2/3 of U.S. retirees say the country is in a retirement crisis
40% worry they will outlive their savings. 1 in 5 already have.
I exclusively served retirees with between $1M - $20M for the first half of my career.
These are 10 of the top retirement mistakes to avoid ↓ ↓ ↓
There's a reason that a large portion of wealth management serves retirees.
Sure, they tend to have the most money.
But there are a ton of ways to add value with financial planning, portfolio management, and tax planning.
Just to list a few....
Jun 12 • 22 tweets • 4 min read
Most people think losses = automatic tax write-off.
Regardless of income level, active vs. passive, W-2 vs. 1099, etc.
The IRS plays by a different set of rules.
Here's what you need to know about writing off losses against income to save on your taxes: ↓ ↓ ↓
If you are a W-2 employee and think "how can I offset as much of this ordinary income as possible"?
The truth is, there are only certain ways to do that.
Jun 11 • 27 tweets • 5 min read
30% of employees & execs at public companies are compensated with company stock.
Many of them ignore it & leave a material amount of $$ on the table.
I serve employees at $META, $NVDA, $ACHR, $AMZN, $PD, $Z, $TEAM, and $GOOG.
Here's how we master their stock awards ↓ ↓ ↓
Advising on equity compensation should be full-spectrum.
It's not just "how much should I hold/sell".
Equity can be a material portion of a TC package, which needs a comprehensive plan for managing it.
Jun 10 • 35 tweets • 5 min read
Want to buy a house in 2025/2026?
This thread has all you need to get started.
I spent the time laying everything out with practical tools, screenshots, and explanations for everything ↓ ↓ ↓
This is not another "rent vs. buy" thread.
This is a "tell me what I need to know if and when I buy" thread.
I serve a client base that's unlike most in the entire wealth management space.
--45 clients.
--$100,000,000+ in managed liquid assets.
--Average age of 38.
Here are 10 life & money themes that I see with high-performing millennials (some might surprise you) ↓ ↓ ↓
1. Financial Uncertainty and Planning
Anxiety about long-term security, home buying or relocating, raving for children’s education, retirement investment choices
Rising cost of living, financial literacy challenges, market instability.
Jun 3 • 21 tweets • 4 min read
You make $500K, $1M, even $5M/year. Your net worth has multiple commas.
But here’s the uncomfortable truth:
High income and/or High net worth ≠ bulletproof finances.
Here are 10 blind spots I've found in almost every high performer I've met (with resources to fix them):
1. Overconcentration in a single asset.
Notice I didn't say concentration (a powerful way to grow wealth quickly).
But not all concentration is a success story.
Ask early employees at Blue Apron how their IPO went.
May 30 • 21 tweets • 7 min read
I'm going to go out on a limb here.
This may be the only thread you need to read about understanding equity awards in a private or public company.
I spent the time laying everything out with 19 custom Canva visuals I made to communicate key concepts:
I work with employees and founders throughout public & private tech.
Even with years of nonstop equity consulting, I learn new things constantly.
Each equity package is unique & liquidity events are extremely specific.
Let's dig in.
Mar 20 • 24 tweets • 5 min read
Having a high-income W-2 job is one of the least tax-efficient ways to make a living.
Salary, bonuses, RSUs, & commissions are all taxed the same.
("Ordinary Income" -- the most difficult to offset.)
Here are 10 legitimate ways you can reduce taxes as a high-performing W-2:
^^This is one of the most common questions I get asked by clients & prospective clients:
"We make $400K - $1M in combined W-2. We're getting crushed on taxes. Is there anything we can do? Most people say there isn't."
In some ways, this is true. In some ways, it isn't.
Mar 14 • 28 tweets • 8 min read
Business ownership can be a massive cheat code to building and sustaining wealth.
I’ve been helping business owners and founders with comprehensive wealth management and tax strategy for 11 years.
Here are 25 slides from a recent presentation that I'm releasing for free:
First -- if you get value from this (or any of my content), consider throwing me a follow / like / comment.
I post daily with 100% original personal finance content.
This account helps me grow my business, and supporting my content helps get it in front of great fit clients.
Mar 13 • 25 tweets • 4 min read
"Charles" worked for a startup that was acquired by $META.
His total package was ~$4.5M (big cash now, front-loaded Meta RSUs, & escrow holdback).
QSBS, vesting, estimated taxes, concentration risk -- not fun for a creative director to navigate.
Here's how we tackled things:
Charles is a talented creative director in LA with a young family...and financial planning admittedly isn't his thing.
The acquisition was life changing -- AND Meta's stock price has ripped over 200% since the acquisition.
Heck of a break for him.
Mar 10 • 24 tweets • 8 min read
Understanding taxes could mean hundreds of thousands in added lifetime net worth.
Once it clicks, you never forget it.
I do in-depth tax planning and have taught income tax planning for 5+ years.
Here's how I communicate key concepts in tax (with custom slides for each):
First -- if you get value from this (or any of my past content), consider throwing me a follow / like / comment.
I post daily with 100% original personal finance content.
This account helps me grow and supporting my content helps get it in front of great fit clients.