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:

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.

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.

Need a calculator? Start here:

https://twitter.com/881486490/status/1803413088537882896

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.

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.

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.

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.

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.

"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.

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.

From 22 to 27 I participated in over 300 meetings with HNW/UHNW clients at a comprehensive firm with $4B AUM.

What I saw and heard changed my view of life and money forever.

Here's the good, the bad, and the sometimes very ugly of humans and money (with 15 observations): Death, disability, divorce, sudden money, multi-generational wealth, sibling rivalry, entitlement, philanthropy, legacy.

These are just a few things you would have been exposed to in my seat.

I'm going to go out on a limb here.

This may be the only thread you need to read about buying a house in 2025.

I spent the time laying everything out with practical tools, screenshots, and explanations for everything (in plain English): This is not another "rent vs. buy" thread.

This is a "tell me what I need to know if and when I buy" thread.

My wife and I rented for 10 years before buying.

Do what's right for your life and your finances.

→ You live in Austin & rent for $8K.
→ You are building a $2.1M new construction in Park City.
→ You want to buy a place in TX & settle back there ~2027.
→ You have a 2-year-old and a 2nd on the way.

How do you even start to approach this?

REAL financial planning: You make $750K+ per year in total cash compensation and have $3M+ liquid after-tax investments with more coming in the form of liquidity events and trust distributions.

You're also partially compensated with a crypto token which is highly volatile.

I've worked directly with the wealthy and ultra-wealthy daily for 11 years

➜ Coast-to-coast
➜ 22 to 98 years old
➜ $1,000,000 - $300,000,000 net worth

Here are 10 things I've learned about humans and money: 1. There are kind, hard-working, values-based people ~everywhere~.

I've lived in 7 different states and currently serve clients in 16 states.

There are also assholes everywhere.

Stereotyping based on any measurable demographic is a mostly useless exercise.

I've been using @Canva to drop visuals that speak to key concepts in financial planning, investing, tax, & equity

Understanding certain financial concepts just might help you end up with the life you imagined (and the net worth to match)

Here's my latest batch of 10 designs: @canva 1. Time Horizon and Holding Period Return

We may not know what college looks like in the future...

...but there's no way I'm allowing my family to be caught flat-footed when it comes to the cost of my daughter's education

Here's what you need to know about 529 education savings plans: 1. No one knows exactly what secondary education will look like in 10-20 years
2. There IS such a thing as "over-funding" a 529
3. Yes, you can simply cash flow the cost if you have the means
4. Yes, there are other ways of saving for this goal like an after-tax brokerage

You've worked hard to earn your stock options & RSUs.

They are now sitting at a nice value on your balance sheet, but you don't know if you can sell them.

Here's what startup founders and employees should know: First, if you hold shares in a private company -- you often can’t sell your stock without the company’s permission

Many late-stage companies want to protect their cap table

Also, if you're at a Series A-C startup, there will very rarely be any buyers in the open market anyway

Most people approach buying their first home without doing any prep work or knowing how it works

We saved for years, strategized, and surrounded ourselves with an amazing team to ultimately outbid all other offers with confidence

Let's rundown everything you need to know: First, your maximum home budget should always be a reflection of your financial situation, cash flow, and other goals (including life goals and geographic moves)

Not just the maximum amount a lender is willing to provide via pre-qualification

Imagine a $10,000,000 wire hitting your checking account at 30 years old

For some -- this could be the beginning of a downward spiral into chaos & terrible financial decisions

For others -- this is the start of a dream life where they never have to worry about $$ ever again: "Brian" joined a tech startup as a very early developer

10+ years later, the company is worth billions and there's finally a outlet for liquidity

The NFL just made a game-changing move 1 week before it kicks off the '24-'25 season

They will finally allow Private Equity firms to buy ownership stakes in teams

--Why is the league finally opening up to PE?
--What is private equity?
--What does it mean for the league? This week NFL owners voted to allow select private equity firms to invest up to 10% in a team

The vote passed with 31 of 32 owners in favor (Bengals voted "no")

2 in 3 U.S. retirees say the country is in a retirement crisis (66%), and about 40% worry they will outlive their savings —

— 1 in 5 already have...

I served retirees and pre-retirees with between $1M - $10M for 7 years

These are 10 of the top retirement mistakes to avoid: There's a reason that a large portion of wealth management serves retirees

There are so many ways to add value with financial planning, portfolio management, and tax planning

Just to name a few: