Luke Matthews

Co-Founder | Lifestyle Blogger |  Content Marketer | Storyteller 

I teach you how to write with AI (and win LinkedIn)

Building in public on LinkedIn™ is risky for you. 

You aren't a 20-something Instagram model or a 33-year-old drop shipping bro bragging about 6 figures from Bali. 

You have a real business and a real reputation to uphold. 

You want to take advantage of more opportunities through visibility on social media, but you know there are privacy risks that come with that.... 

Most AI models take your data and sell it. 
Most social media platforms take your data and sell it.
Most marketers don't understand this, which can expose your company.

That's where I come in. 

I've been marketing for over 10 years on social media, built over 250k followers across all platforms, and I've ghostwritten for some of the biggest personal brands in the world. 

But beyond that, I value privacy and staying hidden. 

It takes skill to build a personal brand that not only generates revenue for your company but also remains secure and private. 

I help you build on social media and maintain your privacy using secure AI systems and world-class ghostwriting. 

Sound interesting?

Don't message here on LinkedIn.

Email me instead and use subject "𝗜 𝘄𝗮𝗻𝘁 𝘁𝗼 𝗯𝘂𝗶𝗹𝗱 𝘀𝗲𝗰𝘂𝗿𝗲𝗹𝘆"

luke@wizardofoddmarketing.com

--

Want to learn how to use AI safely?

Follow me and subscribe to my email list to learn how to use AI tools safely and securely without exposing your data and private life to the world. You can subscribe by clicking any link in my profile as they all go to my newsletter on Substack.

Founder - Lead Wizard & Ghostwriter

Linkedin & Twitter Ghostwriting Services for CEOs, Influencers, and Tech companies. 
Reach your audience with a sprinkle of magic, the power of explosive copywriting, and let the WIZARD OF odd MARKETING help make your biz a LOT  less boring.

I have been banned over 10x on LinkedIn. 

The brutal truth is the system ain’t fair…

In business and in life those willing to cater to the system (and exploit you) end up profiting from it. 

Social media has made this reality worse. 

It’s not about how skilled you are.
It’s about how skilled you can talk. 

(& it’s about who u know aka how good you are at kissing up to leaders and using errr befriending them on your climb to a seat at the table)

I decided this rat race wasn’t for me. 

So I’m playing a different game now. 

Rebuilding in the shadows. 
Learning new skills. 
Making new friends…

Friends that are hackers, rebels and the anonymous geniuses defending digital freedom…

Because look, complaining about broken systems accomplished nothing…

Action wins. 

PS Hi LinkedIn. Who’s still here?

2 posts in a week whoa 🤓

Luke M

I used to spend 8 hours a day engaging on LinkedIn. 

In 2025 I spent less than 30 minutes a day... 

So why change?

Well for starters I shut down a lot of things this year. I ghosted the platform for months, I shut down my old businesses and went into the shadows to consider a rebuild. 

But last year a lot changed on the platform.

Commenting alone is now far less effective for growth.

There are too many AI comments.
There are too many thought leader ads.
There are too many virtual assistants focused on ROI.

The odds of your comment alone being seen, considered and replied to simply went down a lot. 

So here's what I have been doing in Q4:

I comment for 15 minutes a day.
I make sure each comment is interesting.
I follow up the comment with a simple DM. 

(oh and yes I remove all my comments, posts and footprint 30-60 days after with a pretty cool AI tool.... DM if your curious why I do this!) 

No you wont get a ton of reach or follower growth this way!

But you will start conversations....

PS Have you changed your strategy in 2025?

It's easy to get 1000 likes a post (like I used too)

Here's how to be a LinkedIn influencer: 

1. Talk about LinkedIn. 
2. Be good looking and post pictures.
3. Write short, broad content. 
4. Spend all day commenting. 
5. Do this for 90 days. 

OR 

69. Pay a team to do it all for you. 

But here's the truth about this blueprint. 

You missed the window when this was possible for anyone. It's too late now on LinkedIn to do this organically. The market has changed, agencies don't work as well, organic is dying and this actually isn't the best strategy unless you want to pretend the old system still works. 

The better way? 

Cut the dopamine. Pick a niche. Speak to that niche. 
Accept less reach. Accept slower growth. 

But reach a very targetd audience. 

In summary...

You need a real skill and a real niche to focus on.

The generic LinkedIn growth expert is playing an old game to take your hard earned money by fooling you with cheap dopamine. 

You will never become them. 

You don't need a personal brand.

You just need to be an expert with a real skill and a specific niche.

PS Who bought cool AI tools for Black Friday?

I now separate work and my personal life.

But not for balance... I do it for privacy.

If you wanna work 16 hours a day and find joy in that then I see no reason at all to say that's unhealthy. 

So this post isn't about encouraging balance.

I mean, I'm the guy who posted 3x a day and spent 8 hours+ a day commenting and connecting on LinkedIn for years who now has a cartoon profile pic, posts 1x a week and barely comments...

I enjoy the unhinged and unbalanced life.

More fun. More purpose. More stories.

And yet I've worked hard to seperate personal and business in 2025.

That's meant shutting down a lot of social media accounts, AI tools, services, clients and ways that I show up on the internet. 

I use Linux for personal stuff.
But Windows for work. 

I use a rebuilt android OS for personal stuff.
And only use an IPhone hardened for work.

I still post on LinkedIn for work. 
But I removed all pics and stories connected to my life.

I could go on and on...

But for me, seperating work and my personal life hasn't been about balance. It's been about privacy and being more intentional with my time, my words and my efforts... 

I believe the internet is no longer a place for authenticity. 

It's simply a place to do commerce. 

So look, do you but if your password is the same for your bank and your LinkedIn account....

Maybe it's time for an audit of yourself eh peasant? 

🧙‍♂️

I only log in to LinkedIn on Windows. 

I use Linux for my personal data and files...

Running more than one operating system on your computer is called multi-booting. 

This summer as I began to purge myself of big tech I realized that I couldn't full exit the system yet... 

Even though I concluded that:

Using Google search is a privacy risk.

Using ChatGPT is a privacy risk.

Using Cloud AI is a risk...

Publishing content connected to your full name, actual face, phone number and home IP address is also a privacy risk…

I also realized I couldn't cut the last 1% of these data stealing big tech tools and programs...

This is where taking back your privacy requires effort.

So I decided to learn how to sandbox my work/private life online environments.

Sandboxing is when you run apps/programs in a secure, isolated framework to restrict those tools access to the rest of your systems files and resources.

Basically I wanted to figure out how to isolate tools like LinkedIn so they don't have access to my other files and life.

This takes some skill, but deleting 100% of everything just wasn't possible for me yet. 

It's a constant game of learning but I think it's worth learning how to shield your personal data and sandbox your work life, personal life and daily life environments from each other.

Otherwise you are at the mercy of data leaks, hackers, corrupt big tech and government policies…

Personally I think it’s worth the effort to learn and seperate tools, systems and resources.

What about u?

PS Yes I know Windows is getting worse... But Mac? EW

Do you share your live location with social media apps? 

I do not. Here's a quick why/why not list... 

✅ Positives to location sharing:

It's convenient (easy to meet up & connect)
It's social proof (events, hotspots, clout)
It gives you steak recommendations. 

✖️ Negatives to location sharing: 

It creates movement patterns for 1000s to study.
It allows your data to be harvested more easily.
It establishes a physical digital footprint.

I have always been careful to not share my live location.

I analyze every photo or post written and consider what kind of footprint I'm leaving behind. 

Am I paranoid? 

Perhaps... But this elder-millennial is gonna keep walking the line between using tech and disappearing into the shadows..

PS Sharing any photos adds to your risk. 

This photo has clues in it. 

Where do you think this photo was taken?

The gatekeepers are losing their grip.

For years, "world-class" meant big budgets, big teams, and exclusive tools. You had to be part of the club.

That era is over.

AI has kicked the door down. A new report from Artlist, based on insights from 6,500 creators, calls this "The third wave of democratization."

What does that mean?

It means anyone with a laptop can now produce studio-quality work. It means a couple of skilled individuals can take on companies in the hundreds. It means the playing field is wide open for anyone willing to learn.

Of course, when anyone can make anything look perfect, the game changes.

It's no longer just about technical skill. It's about taste. Vision. Strategic thinking.

As the report says, direction now matters more than ever. AI handles the production, but only you can choose the ideas that move people. Your choices are what set you apart.

This is why I find AI so appealing. It's not about replacing humans; it's about empowering the ones that choose to accept the new game. It is the great redistributing. An opportunity for anyone willing to learn, not just those with deep pockets.

The little guy has a chance. The rebel. The creator with a dream. The expert with a real skill.....

I think that's pretty cool.

PS if you want to read more about the state of AI check out the AI Trend Report 2026 from Artlist (who sponsored this post).

https://lnkd.in/gf7e8aXE

Brand partnership • Scale your business privately with AI.

How to pay $0 with 9 private AI tools.

(I replaced my tech stack with these brands)

This summer I quit using most AI tools that required overpriced monthly subscriptions/credits and stored my data in their clouds. 

So I had to replace 99% of my tools. 

From $500 to less than $25 a month.

Here's my list:

Notion >Crypt(.)ee for note taking and ideas.
Airtable > AppFlowy for content management.
G-Suite > Proton for secure email and file hosting.
ChatGPT > Okara for private open source AI. 
Loom > Cap so I can record my screen with video.
Perplexity > DeepSeek with Ollama for research.
Canva > Penpot for self hosting creative assets.
Manus > Venice for AI research purposes.
Slack > Signal cz I don't need all the fluff.

So yeah this list is a lot longer.

But I know your attention span is short.

I'm still getting used to some of these new tools.

(and I paid for Proton Premium too btw)

The truth is, it's inconvenient. 
I was used to my tool stack. 

Learning new software and setups is a challenge.

But avoiding subscriptions the best I can and maintaining max control of my data is my decision maker.

PS Yes I left out the self-hosting tools and process...

(I gotta make you follow for more somehow right?)

Financial planning and education (without the jargon) I Creating blueprints for high-earning sales executives and business owners

I left the financial industry because I saw a problem.

People wanted to work with a planner, but they ended up becoming a number on a spreadsheet.

I had to leave to start something new.

And now?

I'm a fee-only planner who helps salespeople & equity compensated employees under 45 give a purpose to their paycheck.

I left the large financial institutions to start my own independent company. I did it so people could pay for real planning and not just an agenda to sell a hidden product. 

As a true fiduciary, Pashman Financial, LLC was built on that promise by focusing on you and you only.

🔵 Why people hire me? 

Well, people have come to me with the following problems:

- They want peace of mind with their money
- Their old advisor barely communicates with them
- They want an answer tailored to them, not from Google
- They felt pressured to buy a product that wasn't a right fit
- They are great at making money but struggle to keep it
- They want a simple plan that's easy to understand
- They want someone to hold them accountable
- They want someone they can trust

🔵 What are my services?

I help identify your goals, craft a financial blueprint that lays out action items to hit them, and monitor your progress. 

💵 Cash Flow Management  
📈 Equity Compensation
🏡 Real Estate Planning
📊 Investment Planning
📍 Retirement Planning
🛡 Insurance Planning
📚 Education Planning
💲 Tax Management
💳 Debt Repayment
📃 Estate Planning

🔵 Who do I serve?

Age: Individuals and families between 30-50 years old
Target: Sales pros, tech employees, other millennial families
Location: Virtually anywhere in the U.S.

But I love working with people that are driven to make a change. So even if you don’t fit these criteria, feel free to reach out. Your personality is everything. 

🔵 Why I'm different?

1) My model is primarily a flat fee service. No time trap. 

2) I do not require you to hand over your investments nor require a minimum to work with. Managing your assets is optional and I'll still assist you if you do it yourself. My focus is ongoing financial planning. 

3) I focus on how to increase your cash flow, not just your assets. I work with you to ensure your systems are set and consistently educate you on how your finances work. I get paid to truly keep you accountable over time.

You can find my pricing in my "featured" section on the website. 

Stop delaying action. Shoot me a message to schedule a complimentary intro.

Max Pashman, CFP®

Renting is not a waste of money 
Renting is not a waste of money
Renting is not a waste of money
Renting is not a waste of money
Renting is not a waste of money

It isn’t always “throwing money away”.

In fact, it’s an option that offers flexibility.

It’s avoiding being locked into a mortgage you’re not financially or emotionally ready for.

People underestimate how costly the wrong home purchase can be.

Better to stretch on rent than get trapped by a mortgage you can’t afford.

pashman-financial-llc

schooloffinances

JSESSIONID

li_at

Talks about #money, #wealth, #investing, #personalfinance, and #financialplanning

Helping Founders and Executives Plan for Early Retirement and Exit

Your employer offers you a $200,000 salary. 

But also offers a $200,000 bonus with it.

When you get the bonus, it's taxed just like your salary. 

Except it's withheld completely different from it. 

One question you should always ask:

What will you do with the bonus?

Option 1: Spend it
Option 2: Save it in cash
Option 3: Invest in your company's stock
Option 4: Invest it into your portfolio

No matter what happens, that bonus gets taxed when it vests. 

And if you haven't figured it out by now, I'm not talking about a bonus.

Welcome to planning around Restricted Stock Units (RSUs) 101

90% of parents plan to invest for their kids, but are clueless where. 
 
Here are the full details of common accounts to consider:
 
#1 529 Plan 
 
Usually the first option people think of when planning for their kids. 
 
This is the traditional go-to if you know your kid is going to college. 
 
The reason being is that it provides tax advantages specifically for educational needs. 
 
Pros of 529: 
 
-Earnings are tax-free when used for qualified educational expenses 
-Can front load up to 5x normal contributions 
($19,000 X 5 = $95,000 per contributor) 
-May offer a state deduction depending on the state 
 
Cons of 529: 
 
-If not used for education, earnings are taxed + hit with a 10% tax penalty 
-Limited investments options available 
-Expense ratios could be high 
 
 
#2 UTMA / UGMA 
 
Don't think the funds will be used for college? 
 
One of the most popular alternatives is a UTMA / UGMA. 
 
It can be a good way to provide a nest egg for the future. 
 
Pros of UTMA/UGMA: 
 
-A vehicle that could be used to teach your kids about personal finance 
-Can be used for any purpose and not just their education 
-Exempted from paying a gift tax up to $19,000 / year 
 
Cons of UTMA/UGMA: 
 
-Hurts financial aid as a kids asset and is subject to kiddie taxes 
-Contributions are irrevocable (cannot be taken back) 
-Funds MUST be given to kids when they are 18-21 depending on the state 
 
#3 Custodial Roth IRA 
 
Who doesn’t love a Roth? 
 
Now you can provide one for your child. 
 
This is a unique way to build tax-free money that’s partially accessible penalty-free before retirement. 
 
(Partially is the key word here) 
 
Pros of Custodial Roth IRA: 
 
-Not included in the financial aid calculation 
-Access to contributions are penalty free 
-Earnings are penalty free and/or tax free if requirements are met 
 
Cons of Custodial IRA: 
 
-Restrictions on earnings withdrawals 
-Retirement is a very low priority for an 18 year 
-Full control is given to the child by 18/21 (like a UTMA / UGMA) 
- Child must also earn income to contribute
 
#4 Brokerage (Under Parent's Name)
 
While it doesn’t have many tax benefits, it offers flexibility. 
 
You may not know what to do with your kid's future, so this provides options open to you. 
 
This also gives you control over how to invest and when to gift. 
 
Pros of Brokerage: 
 
-Flexibility around managing and investing 
-No penalties for withdrawals 
-Capital gains tax treatment 
 
Cons of Brokerage: 
 
-No deductions 
-Dividends and trades are taxable in the year received & realized 
-Could be subject to kiddie tax if funds gifted before their adulthood 
 
What works for you will depend on your situation. 

Choose the accounts that fit for your kids! 

- - - - - - - - - - - - -

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Be sure to be subscribed to receive the new one this week:

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Major changes are coming to your finances in 2026. 

Here's everything you need to know:

Every year, the IRS adjusts contribution limits to keep pace with inflation, but 2026 is shaping up to bring some of the most notable increases in recent memory. If you're planning ahead for retirement, these updates matter.

→ Workplace Retirement Plans (401(k), 403(b), 457)

2025: $23,500
2026: $24,500

Catch-Up (50+): increasing from $7,500 to $8,000 (up to $11,250 depending on income)

→ Traditional & Roth IRA

2025: $7,000
2026: $7,500

Catch-Up (50+): increasing from $1,000 to $1,100

→ SIMPLE IRA

2025: $16,500
2026: $17,000

Catch-Up: increasing from $3,500 to $4,000 (up to $5,250 depending on income)

→ Health Savings Account (HSA)

2025:
• Individual: $4,300
• Family: $8,550

2026:
• Individual: $4,400
• Family: $8,750

Catch-Up (55+): remains $1,000

→ What this means for you

Higher contribution limits create more room to lower taxable income, increase long-term investment potential, and accelerate progress toward retirement. 

Even incremental annual increases compound significantly over time.

If you want 2026 to be a year where you maximize your financial opportunities, start planning now.

If you need help building a contribution strategy that aligns with your goals, reach out and let’s talk.

I've fallen off the wagon a bit on LinkedIn.

Less time on here. Less engaging.

Ironically, my impressions have never been better.

But the truth is that I need time to cool down a bit. 

Some people love to flex how often they show up on here or how much they engage. 

When you are a solo business owner, your time just needs to be recharged. 

It's just my simple way of not making my way to a burnout. 

Regardless, I can't wait to go back on full go in a couple of weeks. 

I've never been more optimistic about what LinkedIn can provide in 2026 and beyond. 

Let's keep it going folks!

If I were a DIY investor, these are the platforms I'd be using:

- Banking: Chase
- Investing Platform: Fidelity / Vanguard
- HYSA: Betterment / Wealthfront / Marcus
- Bill Management: Rocket Money
- CC Comparison: Points Guy
- Tracking Progress: Monarch
- Estate Planning: Trust&Will.com
- Life Insurance: Ladder Life
- Donations: Daffy.org
- Budgeting: YNAB

None of these companies paid me to write this. 

I genuinely like the areas that help DIY investors here. 

One area I did not include: retirement software. 

I personally believe that without the right expertise, this is the hardest to execute on your own.

Despite all the things you can do on your own, I think getting a second set of eyes for areas like retirement planning, equity compensation, tax planning, and exit planning needs the expertise of an advisor.

Which tools do you use?

If you can’t manage $1,000, you can’t manage $100,000. 
If you can’t manage $1,000, you can’t manage $100,000. 
If you can’t manage $1,000, you can’t manage $100,000. 
If you can’t manage $1,000, you can’t manage $100,000. 
If you can’t manage $1,000, you can’t manage $100,000. 
 
More money doesn’t equal more financial intelligence. 
 
Learn to do it yourself or hire a fiduciary to help you.

Your friend sells iPhones for $1,000.

You decide to buy an iPhone from your friend.

Your friend says to you:

"Hey you're my friend so I'll give you a 15% discount and let you buy it for $850."

You buy the iPhone for $850.

Because of the high demand for these iPhones, this iPhone has the potential to increase its value or lower it.

And people right now are willing to buy them for $1,000.

You have two choices:

Option 1) Hold on the iPhone and see it's value go up or down

Option 2) Sell it immediately and pocket that $150 profit

All of which depends on a couple of factors:

- Your financial situation
- Your desired exposure
- Your risk appetite
- Blackout periods

And if you haven't figured it out by now, I'm not talking about iPhones.

Welcome to Employee Stock Purchase Plans (ESPP) 101.

52% of families are unprepared for an unplanned expense. 
 
Here's how you can better prepare for it:

Create a safety net in your plan.

AKA an emergency fund. 
 
Doing so for three reasons:
 
-> Access to short-term funds 
-> Avoid tapping into long-term funds 
-> To prevent you from taking on more debt 
 
The chart you see is one that I put together. 
 
I love to incorporate multiple variables to identify the right number. 
 
These are just some examples. 
 
And just my personal take on what I've seen. 
 
You may only need 3 months, but you want 12 months for peace of mind. 
 
The point is that while the 3-6 month rule is a good benchmark, it's also flexible. 
 
Choose the amount that fits your profile. 
 
It's an insurance policy for your goals.

People spend roughly $200 a plate for a Thanksgiving dinner. If they took that $100 and invested it in the market over 30 years you would have made nah I’m just kidding have a great Thanksgiving everyone!

You have Chat GPT for find your answers.
You have Perplexity to find your answers.
You have Gemini to find you answers. 

Yet, you haven't made changes.

Or worse, left wondering what you need to change now. 

Things like:

- Set up automated investing systems
- Build a savings plan for your next home
- Make a debt payoff plan you can stick to
- Build a real equity plan (RSUs, ISOs, ESPPs)
- Create a tax plan for bonuses and RSU vests
- Build a simple spending plan that actually works
- Optimize your account order (taxable, 401k, Roth, HSA)
- Review insurance needs without selling you insurance
- Optimize self-employed taxes and retirement plans
- Run long-term projections for major decisions
- Turn vague financial goals into real numbers
- Review your full financial picture for gaps
- Set up a smart charitable giving strategy
- Create an early retirement roadmap

In other, words you haven't taken action... yet.

We're entering an interesting era of paralysis by analysis. 

We're getting more well informed about our finances thanks to AI.

But the lack of action continues to remain with humans. 

Let's make 2026 our goal to it implement together.

It takes a human to know a human after all.

When you need help, DM me.

"Let's circle back after the holidays"

1st Follow Up: I meant after Christmas

Next Follow Up: Sorry I really meant after Valentines Day

Next Follow Up: Yeah I meant my CPA's tax holiday season

Next Follow Up: Oh whoops I'm on Holiday for the entire summer

Next Follow Up: Scary the year went by! Speaking of which, I meant after Halloween

Next Follow Up: Who are you? Oh yeah. Let's circle back after the holidays.

Don't go into a food coma with your money. 
 
Here's what most miss about finances: 
 
It's not about the fancy stuff. 
 
Investing is awesome. 
So are the investments. 
And so are the vehicles. 
 
But individually, they mean nothing. 
 
The combination of them does. 
 
Things that should be considered: 
 
- Why you have them? 
- How do they work with one another? 
- What role they play with your goals? 
- Where does you money work?] 
- When do you need it? 
 
By having the right plan, you can put a purpose to your paycheck. 
 
You wouldn't wing a Thanksgiving dinner. 
 
Neither should you with your finances.

Happy Thanksgiving!

SpaceX is rumored to IPO at a $1.5 trillion valuation.

While great for employees, it could also be a tax nightmare. 

Take Timmy, for example.

He got 10,000 ISOs back when the company was tiny.

Strike price? 10 cents a share.

Meaning he could buy everything for just $1,000
(10,000 × $0.10)

Fast forward.

SpaceX becomes one of the most valuable private companies in the world.
The latest 409A valuation hits $200/share.

So on paper?

Timmy’s options are worth $2 million.
($200 × 10,000)

He hasn’t exercised yet.

Then, like many employees do, he accepts another job.

And suddenly, the countdown starts.

Most companies give you 90 days after leaving to exercise ISOs before they turn into NSOs.

So Timmy rushes.

He exercises everything in December 2025.

Pays the $1,000 strike price.
No regular tax due at exercise.
He now owns the shares.

Feels amazing.

Until tax season.

Timmy discovers he owes over $500,000 in AMT.

Because AMT treats the bargain he got:

($200 FMV – $0.10 strike) × 10,000 = $1.999 million as income for AMT purposes.

Here’s where SpaceX employees could run into the same problem:

Even if SpaceX IPOs in 2026?

You still can’t sell right away.

Because:

- Newly public companies have insider lockup/blackout periods
- Employees often can’t sell for 6 months or more after IPO
- Pre-IPO shares may have transfer restrictions
- Early investors usually get liquidity before employees

So imagine Timmy:

- He exercised in December to beat termination deadlines.
- He triggered a huge AMT bill on paper gains.
- The IPO happens in 2026, great!
- But he’s still locked up and cannot sell.

Meaning:

The AMT bill is due in April 2026

The shares still aren’t liquid.

He might not be able to sell until late 2026 or even 2027.

This turns from a dream to a nightmare.

This exact sequence has happened before at other rocket-ship startups.

Let’s pause:

Timmy is not a real person.
(This is a hypothetical scenario after all)

But problems like this?
Not made up either.

And it’s preventable.

Here’s what Timmy could have done:

- Run an AMT forecast before exercising
- Exercise earlier when the valuation was far lower
- Exercise gradually instead of all at once
- Plan for liquidity timing around IPO + blackout periods
- Keep cash on hand for any AMT exposure
- Or choose not to exercise at all

And one more nuance:

Even if you owe AMT, you may recover some through the AMT credit, but only if the stock eventually sells for a gain.

If the price drops before he can sell?

The AMT is gone forever.

That’s why ISO planning matters.

Equity can be life-changing.

Or financially devastating.

The difference isn’t the IPO.

It’s the strategy leading up to it.

So if you’re at SpaceX, or any pre-IPO company, run the numbers before exercising.

Don’t end up like Timmy.

90% of employees with RSUs can’t explain how they work.

Here’s the simple version you actually need.
 
Restricted Stock Units (RSU) are equity offered by an employer to an employee. 
 
No upfront financial commitment is required from the employee. 
 
Meaning they pay nothing out of pocket for them. 
 
But rather it’s viewed as a “promise”. 
 
So how do they receive them? 
 
A vesting schedule is attached to one of these requirements. 
 
1. Time served at the company 
2. Performance related 
3. Combo of both 
 
It usually has a 4 year graded vesting period starting a year from the grant date. 
 
After 1 year 25% is vested, then 25% is added after every year. 
 
Example: You have 1,000 shares that has a 4-year vesting period 
 
In this case, 250 will be vested after the first year, 250 for the second year, and the same for the third & fourth year. 
 
So as this happens, how do RSUs get taxed? 
 
Because the employer gives this to employee like a bonus, the RSU is treated as compensation. 
 
Therefore, the entire face amount is treated as income. 
 
This event occurs only when the RSU has been vested. 
 
Example: The amount vested 1,000 stock for $10 FMV? 
 
1,000 X $10 = $10,000 
 
When this vests, this amount is treated as taxable income. 
 
But you receive this in stock, not in dollars. 
 
So how are taxes withheld here? 
 
Employers commonly sell some of the stock it in an effort to withhold the taxes. 
 
For example: 
 
Let’s say 2,500 of stock was vested at $100 = $250,000 
 
Suppose in this example 22% is withheld. 
 
Of the 2500, 550 of them would be sold immediately to withhold the taxes. 
 
Leaving the employee with 1,950 stock after. 
 
If the employer immediately sells at vesting, no additional taxes are due from those stocks. 
 
However, you’ll need to track this because employers might not withhold the correct amount for you. 
 
Monitor this as it vests. 
 
What about your stock after? 
 
When you receive your stock, the price at the time of vesting is the new cost basis. 
 
From that point onwards, the stock is has capital gains treatment. 
 
So should you keep it or not? 
 
This is concentrated stock, which is a risk in itself. 
 
This will depend on your risk tolerance and desired exposure to one company. 
 
Selling some or all may make sense and reinvest in a diversified portfolio. 
 
It all comes down to your preference!

Today: Shirt worth $100

Black Friday next week: “50% OFF! Now $100!”

 What a steal.

If you sell your RSUs, this one mistake can cost you thousands.

Before you sell, always check your cost basis. For example:

You receive company stock at vest
→ Share price at vest: $40

Later, you sell
→ Share price at sale: $100

What should happen:

Cost basis = $40
Sale price = $100
Taxable gain = $60

But what I’ve seen happen way too often:

Cost basis shows $0

So the IRS thinks:

Sale price = $100
Taxable gain = $100

That means:

You’re paying taxes on gains you never actually made

Higher capital gains = Higher tax bill!

The good news:

This is usually a reporting issue.

It can often be corrected before (or even after) the sale.

But only if you catch it.

Before selling any RSUs, ESPP, or stock awards:

- Check the cost basis
- Confirm it matches the vest price
- Fix errors before you hit sell

Because paying extra taxes for no reason is a mistake you don’t need to make.

Educational only. Not tax advice.

If an advisor is suggesting you take out an insurance policy for a minor to fund college, here’s some advice:




RUN.

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