Seth Yakatan

Raising & Selling 📈 $1B+ Raised 💰 22 Companies Sold 🤝

Are you struggling to communicate your vision to the capital gatekeepers?

Are you exploring selling your business but don’t know anything about:
✘ Due diligence
✘ Term sheets
✘ Earnouts

Friend, you're lucky you found me...

I'm Seth Yakatan.

I have 30-odd years experience as a corporate finance professional.

My specialties are:
💰 Raising money
🤝 Selling companies

And I’m f**king good at it.

I’ve raised over $1B and sold 22 businesses.

My career has mostly been supporting small-cap and major corporations seeking capital to grow, or
to find strategic acquirers.

Most of these companies are in: 
— biotech
— cannabis
— pharmaceuticals
— DTC consumer goods

I’ve been on boards, taken companies public, gone up against multinational corporations, raised from VC and PE funds.

All of it. 
Many times over.
Whatever your problem is, I’ve seen it before.

But let me level with you:

What I REALLY love is helping people to get to the finish line.

Talking to entrepreneurs excites me.

But in my experience, entrepreneurs are mostly s**t at raising capital and selling companies.

** They just don’t understand investors **

And that’s where I come in.

Together, we workshop: 
✔ Your pitch
✔ Your deck
✔ Your strategy 

And help you raise the capital to GROW and SELL your business.

If you need this help—and almost every business does—send me a DM.

Like, now.

Don't lose another potential investor or acquirer with the wrong pitch.

Seth ✌️

Co-Founder

Merchant Bank / Advisory / Family Office

Give me $10 on Pump #6 and a case of THC Bevs!

WAIT WHAAAAAAT??

This is Circle K 2026 baby!


>> What’s Happening?

A Circle K franchisee in DFW started selling hemp-derived THC beverages.

This is the 1st major C-Store in Texas to stock THC drinks on shelf.

Lots of SKUs and get this…in-store tastings planned throughout 2026!


>> Why Does This Matter?

This ain’t a trial folks. This is mainstream retail entry.

Circle K is as mainstream as it gets. A roadstop brand with millions of daily customers.

Regulatory limbo? Who cares… make money when consumers buy drinks.


>> What I’m Watching

Can THC drinks outperform impulse staples like coffee and Red Bull?

How do Texas policymakers respond to non-dispensary THC sales?

Who’s next to join the party…Flying J??


The future of THC is in the cold box next to your protein shake.

No alternative text description for this image

Is this the FIRST MAJOR ON PREMISE shot fired for THC beverages??

WELCOME to the 2026 Stadium EXPERIENCE!

THC Drinks are coming soon to an ARENA NEAR YOU!


>> What’s Happening?

Chicago’s United Center just announced its serving hemp-derived THC drinks.

Concerts/Sporting events/Big shared moments.

In case you didn’t know, that’s alcohol’s home turf….

THC is showing up more and more, without asking ANYONE for permission.


>> Why Is This Important?

Booze vs. THC is not the point.

The point is THC is now competing for share of occasions.

Normalization comes from repetition in trusted environments.


>> What Am I Watching?

The first league, venue group, or national operator that treats THC beverages in the same way ?

Who puts up the first THC Beverage advert in a stadium? (Remember USC/ Cookies?)

What major sports/food/airport group jump in next ?


5 beers or 5 2MG THC Beverages??

Same night, VERY different morning

A long held belief just got UPENDED last week:

Vapes just eclipsed FLOWER in terms of sales in CA.

YUP. WILD.

So, ask YOURSELF why…


>> What Happened?

In CA, vape products overtook flower as the #1 seller in licensed dispensaries.

This is a HISTORIC first in the U.S. legal market.

In 2025, vapes pulled ahead, with higher monthly sales and widening share


>> Why Does This Matter?

Flower has been KING forever.

Economics, culture, product…it was Michael Jordan.

Now the consumer wallet has shifted its preferences.

And upended norms (hello Gen Z!)


>> What Am I Watching?

Is Gen Z the demand anchor we should be trying to reach?

Does margin in vapes continue if this trend sticks?

Does quality and testing MATTER, or is price #1?

How does this change the retail plan-o-gram??


Flower has to take off its crown, for now…

But let me be clear: I don’t think flower is losing its heritage or dominance, YET….

I do think that consumer choice and pricing show us how the market is shaping the future…

Little more love from the MJ BIZ scene...
Shout for Rectitude Partners LLC
and my man Nicholas Bowers

thanks to the squad at 

Fat Nugs Magazine
Puff Creative

for a great night....4 Grams...COMING!!!!!

Guess who just figured out how to crack the Show Me State:

My guys at Jeeter - a DreamFields Brand + Elevate.

Keep telling me cannabis is a commodity business….

Jeeter just walked into MO and reminded everyone what a REAL BRAND looks like.


>> What’s Happening?

Jeeter, the No. 1 pre-roll brand in the U.S., just launched in Missouri.

They hit the ground running with a smart partnership with my guys from Elevate (GREAT TEAM) and hit 70 %+ day-one coverage of doors

These guys are going to CRUSH.


>> Why Is This Important?

Brand dominance via culture, community and premium perception.

Missouri is a BEAST with 4-6 groups there KILLING IT and MAKING MONEY.

Jeeter + Elevate treated this one like a brand build, not just a SKU drop.


>> What I’m Watching

Does Jeeter’s lifestyle strategy expand average ticket or just front-load hype?

Can culture from places like California translate to Show-Me economics?

Does this push a pre-roll war in the Show Me State?


Missouri didn’t “get” Jeeter. Jeeter chose Missouri.

Pre-rolls are crowded. Brands aren’t.

Jeeter + Elevate = WINNING.

So did you REALLY think the ban was about hemp??

No no no.

It was about ALCOHOL.

And now the numbers are in:


>> Whats Happening?

Alcohol is done watching hemp from the sidelines.

In Q4 2025 a bunch of companies files highlight lobbying disclosures tied to intoxicating hemp:

Moët Hennessy
Bacardi
Diageo
Brown-Forman
The HEINEKEN Company
Sazerac Company

Hmm….read the tea leaves and follow the money.


>> Why Does This Matter?

Lobbying is balance-sheet-based muscle memory for alcohol.

They have been doing it since 1950 and they are GOOD at it.

Make no mistake, the alcohol industry is acknowledging something BIG:

THAT intoxicating hemp is already part of the adult-use landscape.


>> What I Am I Watching?

Which alcohol players move from lobbying to minority investments?

Or does alcohol flex harder to push hemp off the shelves?

Can cannabis incumbents realize they were out gunned (and outspent)?


Not sure how this plays out but I am going to crack 10mg bev and grab the popcorn!

The hemp ban is coming annnnnnnd it's going to be unenforceable. Full stop.

Everyone screaming "shutdown" is missing the point.

The math just does not math…

>> What's Happening?

Lawmakers have stuffed an effective intoxicating-hemp ban into federal language.

On paper, it tightens THC limits and nukes most hemp-derived products.

In reality, it hands enforcement to agencies that already can't enforce federal cannabis prohibition today.


>> Why Is This Important?

We already ran this experiment.

Cannabis has been federally illegal for decades and yet here we are with regulated markets in most states.

The federal government does not have the manpower, political appetite, or operational clarity to police every convenience store, DTC website, and warehouse in America.

A ban without enforceability isn't regulation ? Just funny…


>> What Am I Watching?

States quietly filling the vacuum with their own rules while Washington argues with itself.

Hemp operators adapting structures, formulations, and channels instead of disappearing.

Cannabis incumbents cheering a "win" that may actually strengthen the very gray market they hate.


You don't fix consumer demand with a memo and you can't kill markets with paperwork.

If lawmakers actually want control, safety, and tax revenue, there's only one answer:


Regulate it and LEGALIZE IT…


Don't pretend you banned it.


If this sounds familiar, it should. We've been here before….

Guess who’s messin’ with Texas?? Cann, that’s who.

Cann is fixin’ to dominate the Lone Star State.

Here’s what’s going down:


>> What’s Happening?

Cann secured Texas distribution with Spec’s.

Spec’s, for those that don’t know, is THE LARGEST beverage retailer in Texas.

Full SKU set in one of the biggest alc retail channels in the USA.


>> Why Is This Important?

This is not a test, a dispensary, one franchisee gone rogue, or a limited run.

THC drinks are moving via mainstream beverage infrastructure.

Spec’s has 200+ doors statewide.

Say what you want, I AM seeing a distribution shift...


>> What Am I Watching?

What other brands can howdy on down to distribution?

What other retailers jump on board now that we have Target, Circle K and Spec’s?

Is there movement on the regulatory side in Texas? (Remember a few months ago they tried to BAN HEMP??)


Want to make sure we give a big congrats to the Cann Team!

Jake B. and Nick Fasano 👏 👏

Feels like Danny Stepper and the LA Libations team left their fingerprints all over here, cause this ain’t my first rodeo…

Want to LEARN MORE? Get your spurs to The Beverage Forum April 2026.

Hang 10 and hit the dispo??

Adult use cannabis may be coming to the Aloha State…


>> What’s Happening?

Hawaii lawmakers filed legislation that would put rec cannabis to voters in November 2026.

If passed by a two-thirds vote in both chambers, Hawaii voters would be asked whether to amend the state constitution to legalize adult-use cannabis.


>> Why Does This Matter?

Ballot initiatives are cool but they are NOT a guarantee.

This was not brought forth by the electorate but by elected officials…

Not sure this get traction or mahalo…


>> What Am I Watching?

Do MSOs even bother modeling Hawaii as a near-term market?

Is capital ready to fund something in one of the worlds largest tourist economies?

Do voters notice they’re being asked to decide a policy?


Feel like another version of Pele’s curse.

Cannabis style…I will just grab a shaved ice.

Why can’t an MSO be successful in one of the BEST markets in the US?

Missouri is quietly becoming one of the most attractive cannabis markets in the country — WITHOUT the MSOs.

Go figure.


>> What’s Happening?

Curaleaf exited Missouri.

Not cut back. Not paused. EXITED.

And they are not alone. No major MSO has meaningful exposure to Missouri.

Yet MO is consistently ranking among the healthiest AU markets in the U.S…


>> Why Does This Matter?

Missouri breaks the MSO playbook.

Limited license structure, strong retail economics, rational competition.

Not race-to-the-bottom pricing.

This is the rare cannabis market where operators actually make money (REALLY).


>> What Am I Watching?

When do private equity and strategic buyers re-rate “boring” markets?

Does the next consolidation wave starts OUTSIDE the MSO universe?

Who comes out of this market as a winner?


Missouri didn’t fail the MSOs but the MSO model failed in Missouri.

Not every great market wants a national flag planted in it.

Sometimes the best markets are the ones Wall Street ignores.

Where do hemp beverages belong?

Well, what do we know:

1. They sure found a way to enter traditional distribution channels

2. Alcohol use is declining

3. Consumers are driving demand

With the hemp ban looming I'm not sure which way is UP.

So you tell me?

Thank you to my friend Peter Su, PBC-CP, CTP, CCBP, CRS, GRCP, GRCA, IDPP, CBE for having me on...

Why do you keep doing this LinkedIn thing ???

BECAUSE THE POWER OF PERSONAL BRANDING IS YOUR FUTURE.

Here's a case study:

Few years ago met Lisa Williams via LinkedIn.

She reached out.
We got to know each other
We have supported each others' collective journey.

Lisa Williams is: 
— A working mother
— An entrepreneur
— Who owns two businesses
— Keeps up with her content 
— And is a TOTAL badass!

About 2 years ago she purchased a product SHE believed in. 

Hello Again...Something to help female health, specifically menopause.

She started putting some videos on TikTok...

And guess what... last week SHE WENT VIRAL.

1,000,000 views
122,000 likes
5,000 comments
21,000 saves 
59,000 forwards

AND SO MANY SALES SHE COULD NOT KEEP UP.

NEVER QUIT. 
NEVER question if you should be posting.

And buy some Hello Again!

And check the video here: https://bit.ly/4qCX4sq

When you fail 3 times, why not try for a 4th??

That’s what PA is doing right now as the state makes its FOURTH attempt at a move to Adult Use.

Sure, why not??


>> What’s Happening?

My guy Shapiro gave his fourth budget address.

Increasing overall spending by 6% without broad-based tax hikes.

Oh and he put adult-use BACK on the table…AGAIN.


>> Why Does This Matter?

PA is surrounded by NJ/NY/MD/OH, all of which are pumping REC.

The budget conversation shows how much $ PA is leaving on the table staying medical.

How ELSE can you spend more and NOT tax the general public?


>> What Am I Watching?

This is now #4. Can it REALLY HAPPEN this time?

What will be the policy tradeoffs if this happens? Who loses?

Is THIS a state surrounded by AU finally admitting leakage is a tax policy?


Adult-use didn’t magically reappear…

It reappeared because PA needs the $$$.

Politics and budgets are not based on morality…

Bet your butt they are based on COLD HARD CASH.

And AU seems like a magical cash machine.

Everything's BIGGER in TEXAS? Well, Texas Original just bet the ranch.


>> What's Happening?

Texas Original just opened the largest medical cannabis facility in Texas.

They’re expanding cultivation and processing capacity to meet rising patient demand.

No change in law…no ballot initiative.

Just cash, concrete, steel, and CONFIDENCE.


>> Why Does This Matter?

Well son, you don't go build the largest facility inside one of the most restrictive medical programs in the country…

THIS is what early movers look like in medical states.

And might signal that regulators are comfortable enough to let serious operators scale.


>> What Am I Watching?

Does demand absorb this build?

Does the program allow for success?

Who’s the next operator is to break ground?


Texas ain't first.

It won't be loud.

But when it moves, it will move at TEXAS SCALE.


Cowboy UP y'all.

This will make some people uncomfortable.

Good. Read it anyway.


>> What's Happening?

A new study from the National Bureau of Economic Research suggests that legal marijuana access is associated with lower suicide rates among older adults.

Particularly once dispensaries actually open.

Not legalization on paper.

Real access. Real products. Real use.


>> Why is this Important?

Older adults deal with chronic pain, sleep issues, anxiety, isolation.

And guess what? They're also the group with the highest suicide risk.

When legal cannabis becomes available, suicide rates in this cohort go down.

Let's not pretend this is nothing while we happily prescribe opioids, SSRIs, and booze like Tic Tacs…


>> What Am I Watching?

How long policymakers keep saying cannabis has "no proven benefit" while data quietly stacks up.

Whether public-health conversations finally acknowledge harm reduction instead of moral panic.

Who actually cares about outcomes and who just cares about optics…


No one is saying cannabis is a cure.

But dismissing data because it challenges the norms is bad science and worse policy.

If legal access helps even a subset of people feel less pain, less despair, or a little more okay, maybe that's worth taking seriously.

Just a thought…

Montana, the Gold and Silver State, is going GREEN.

Montana’s cannabis market just put up a number…which I found very interesting.


>> What’s Happening?

AU retail in Montana threw up a record $327M in sales in 2025.

AU represents roughly 90 % of Montana purchases.

AND this growth came DESPITE falling retail prices per gram.


>> Why Does This Matter?

Pattern recognition: price compression + volume growth = real consumer demand.

Out of this, the state grabbed $60 million in tax revenue, underscoring how important this product can be.

Medical markets seems to vanish in the face of AU. Unclear how this moves in S3…


>> What Am I Watching?

Montana works because it’s not drowning in licenses or over-financialized.

Its relatively open licensing structure and modest population make it a unique case, but can it last?

It’s also a NO MSO Zone…proving that you don’t need MSOs for a sold adult-use market.

Low population, controlled rollout, limited speculation.


Markets like this don’t scale nationally, but they do expose what broke elsewhere.

Record sales are nice, but structural market health is the REAL story.

We’ll see what prevails here.

Best advice for a bad outcome: Let someone ELSE pick your dose.

Or worse still, let someone who knows NOTHING about dosing pick your dose…

Because that’s what’s going on


>> What’s Happening?

Food & Beverage put out an article on the “perfect dose” for HEMP Beverages.

At 2.5MG

2.5MG??

REALLLY???


>> Why Is This Important?

It reveals a gap between cannabis reality and every outside stakeholder.

2.5mg ain’t a “sweet spot”. It’s a training wheel AT BEST.

Alcohol didn’t scale on near-beer.

Cannabis won’t scale on microdoses dressed up as safety or wisdom.

Low-dose has a place. (THANK YOU Cann)

Calling it “THE PLACE” is telling me you don’t understand the market.


>> What Am I Watching?

How much mainstream “acceptance” does this get?

Is this the way Bev/Alc gets comfortable?? (You sure sell more cans at 2.5mg…)

How many consumers do not “feel” an effect at this level???


2.5mg is not the right dose.

If your entire thesis starts and ends there, you’re throwing darts blindfolded.

While congratulating yourself for hitting something, anything.

Think your business is HARD?

Try this:

1. Every state (and city) has a different set of rules

2. The Government taxes you at an exorbitant rate 

3.  Capital flow is weighted to larger and later-stage operators

4. There is very little capital to begin with...

Now tell me you product is not Federally legal...WELCOME TO C@NNABIS!!!!

Appreciate the love from Alex D. and the squad from The High Index for the spot!

Failing to raise capital in c@nnabis ?

Get yourself to where the decision makers gather in ONE ROOM
Hyped as always for another sesh with my folks from IgniteIt Cannabis
thats right...

I AM COMING DOWN THE PIKE...
February 10th, 2026
Westin Jersey City

I heard The Boss is playing a set....

Register HERE: https://bit.ly/49pHgUF

and use my CODE: SETH20

Patrick Lane Elliot Lane Javier Hasse

It’s NEVER a good idea to let government run a business.

Right??

Anoka, Minnesota is set to cut the ribbon on the Anoka Cannabis Company.

The first and ONLY city-managed dispensary in the U.S.

What could possibly go wrong??


>> What’s Happening?

A city running retail cannabis is like a turtle teaching people how to fly…

Bad idea for government to staff, regulate, and be accountable to voters.

This seems like a BIG departure from the usual “license it and pray” model.


>> Why Is This Important?

This city just decided licensing WASN’T enough.

Screw regulating private operators, Anoka wants to own the P&L too.

This is a fundamental shift for government FROM oversight TO asset control.


>> What Am I Watching?

How soon till every cash strapped municipality gets in the game?

Does this model work financially?

How does a city deal with illicit markets?

How long until they start growing weed and creating their own brand…??


Cannabis didn’t normalize…

It went on the city Balance Sheet.

Government is best which governs least, PERIOD.

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®

50% of people have no idea what tax bracket they're in.

And most think more taxes mean less income. WRONG.

It's not a flat rate. 

The US tax system works at a progressive rate. 

In other words, each level of income is taxed at different rates. 

As new income is included, it is taxed at a higher rate. 

BUT that doesn't mean all of the income is taxed at that rate. 

The highest tax rate is called the "marginal rate". 

The overall tax rate (taxes divided by taxable income) is called the "effective rate". 

Big difference!

undefined undefined

pashman-financial-llc

schooloffinances

Helping Founders and Executives Plan for Early Retirement and Exit

The worst financial advice I've seen online: 
 
- Renting is a waste of money 
- Pay all debt first before investing 
- Spend everything now cause YOLO 
- Index Universal Life is better than a 401(k) 
- Don't increase your income so you can avoid more taxes 
- Buy [insert expense] solely because you can write it off 
- Index funds are bad because they are boring 
- Use your credit card as your e-fund 
- Never buy or lease a new car 
- Invest your e-fund 
- 401(k)s are a scam 
- All debt is bad 
 
These can either be challenged, too extreme, or just plain wrong. 
 
What might work for one person might not for another. 

What are some bad ones you've heard?

LinkedIn:

"Hot Take:

(insert most obvious common sense take)"

Going from $1,000 to $1,000,000 will create happiness. 

Going from $9,001,000 to $10,000,000 won't. 

Same dollar increase. 

Massive difference in results.

Once you elevate from levels of normal finanical stress such as:

- Going past paycheck to paycheck
- Paying off all your high interest debt
- Funding your children's education goals
- Purchasing your first home

Getting money for the sake of money becomes meaningless. 

You have to shift yourself into the next stage by asking a question:

-> How is wealth letting you focus on your happiness?

Not, how is wealth creating happiness.

It supports what actually drives happiness, such as:

- Financial independence so you can focus on your passion projects
- Security, so you can allocate your attention to your family
- Philanthropy so you can give back to your community

Then once you cross that point, what does more wealth do?

Each person has their own inflection point they cross. 

For some people, it’s $1 million.
For others it’s $5 million.
But for many, it’s when they stop worrying about bills.

And slowly, more wealth becomes just a number.

I bet you'd take $1 million focusing on what makes you happy versus $100 million still trying to figure that out. 

You might not need more money.

You might just need a clearer purpose for it.

You don’t need a financial planner if you’re HNW.

You just need to do the following:

- Investment planning
- Portfolio construction
- Asset allocation modeling
- Rebalancing across taxable, tax-deferred, and tax-free accounts
- Tax-aware asset location
- Capital gains management
- Tax-loss harvesting (and not violating wash sale rules)
- Multi-year tax projections
- Roth conversion timing and sizing
- AMT modeling
- Net investment income tax planning
- Equity compensation analysis (RSUs, ISOs, NSOs, ESPPs)
- 83(b) election decision modeling
- ISO AMT exposure tracking
- Concentration risk analysis
- Diversification strategy for concentrated stock
- Trading windows and blackout period planning
- Liquidity planning for large tax events
- Cash flow modeling across good and bad years
- Emergency fund optimization
- Opportunity cost analysis of excess cash
- Life insurance needs analysis
- Disability insurance review
- Umbrella liability coverage review
- ACA subsidy modeling
- Medicare planning
- Early retirement feasibility modeling
- Sequence-of-returns risk management
- Withdrawal strategy optimization
- Tax-efficient withdrawal order
- Guardrails vs fixed spending analysis
- Social Security claiming strategy
- Survivor benefit analysis
- Longevity risk modeling
- Estate planning coordination
- Beneficiary review across all accounts
- Annual exclusion tracking
- Lifetime exemption modeling
- Charitable giving strategy
- Entity structure planning considerations
- Reasonable compensation analysis
- Backdoor and Mega Backdoor Roth execution
- Exit planning scenarios
- Real estate analysis 
- Rent vs sell decision analysis
- 1031 exchange considerations
- Stress testing everything above
- Updating all of this every year
- And not panicking during market drawdowns
- And explaining it clearly to your spouse
- And actually implementing it correctly
- And staying compliant

Good luck!

"W2 employees never become millionaires."

Bulls***. I've consulted with 100s entering early retirement. 

Many were W2 employees, never actually owning a business. 

Or at least use it as a primary means of accomplishing millionaire status

They've crossed that point using the following methods:

- High savings rate towards stocks and real estate
- Equity compensation (More commonly via ISOs)

Owning a business is a massive opportunity to get there. 

And we've seen people retire early thanks to it too.

But it's not the ONLY method to create wealth.

Gotta pick that path that aligns with you.

But what do they all share in common?

Not sitting on the sidelines. 

They let investing take action. 

You earned hard for your paycheck. 

Now make it work harder for you.

Capital gains taxes can be your biggest ally or your worst enemy.

Here’s everything you need to know how they can affect your tax bill:

What is a Capital Gain?

It’s a tax applied when you sell an asset for a profit.

These assets can include:

-Stocks
-Crypto
-Real estate
-Businesses
-Personal property

There are two types of capital gains:

Short Term (STCG):

-> Assets held less than 1 year
-> Taxed as ordinary income

Long Term (LTCG):

-> Assets held more than 1 year
-> Taxed at preferential capital gains rates, separate from income taxes

Here’s a breakdown of the federal long-term capital gains rates for 2026:

Single:

-0%: $0–$49,450
-15%: $49,451–$545,500
-20%: $545,501+

Married Filing Jointly:

-0%: $0–$98,900
-15%: $98,901–$613,700
-20%: $613,701+

Relative to income brackets, you can see the immediate difference.

For Example (Single):

If you earned $200k and had $10k in STCG, it’s taxed as ordinary income.

Assuming a 32% marginal tax rate:

$10,000 × 32% = $3,200 in federal taxes

For $10k in LTCG, it’s taxed at the capital gains rate:

$10,000 × 15% = $1,500 in federal taxes

A huge difference!

But here’s where people mess this up:

Your capital gains rate depends on your total taxable income.

“Taxable income” is your adjusted gross income (AGI) minus below-the-line deductions (standard or itemized).

Which means those ranges include both your income AND your capital gains.

Example #1: Single, $50,000 Income, $10,000 LTCG

Total taxable income: $60,000
This puts all LTCG in the 15% bracket.
Tax:
$10,000 × 15% = $1,500 (Federal)

Example #2: Single, $30,000 Income, $10,000 LTCG

Total taxable income: $40,000
This falls entirely within the 0% bracket.
Tax:
$10,000 × 0% = $0 (Federal)

Example #3: Single, $30,000 Income, $20,000 LTCG

Total taxable income: $50,000
The income takes up the first $30,000.
Leaving $19,450 left in the 0% bracket.
$19,450 × 0% = $0

The remaining capital gains spill into the next bracket:
$550 × 15% = $82.50
-> Total LTCG tax: $82.50 (Federal)

This is why being strategic about when you realize capital gains matters.

By spreading gains over multiple years, you may take advantage of lower brackets.

Finally, remember:

Capital gains are not taxed inside tax-advantaged accounts
(e.g., 401(k)s, Roth IRAs).

That’s why most tax-loss harvesting opportunities live in taxable brokerage accounts.

Disclaimer: This is for financial education purposes only and not financial or tax advice.

A guy tweeted he put $50K in a Roth IRA.

Said it was one of the worst decisions he ever made.

And that’s great! A big reason:

Because if he contributed a total of $50k over the years, he could take out $50k of contributions penalty-free whenever he wanted.

“bUt yOu cAn’T tAkE oUt rEtIrEmEnT mOnEy dUdE”

Well…

This is actually a little secret hidden inside Roth IRAs.

Your earnings are distributed tax-free if certain conditions are met, most commonly being age 59½ and having held the account for at least 5 years.

But your contributions can be withdrawn at any time.

Roth withdrawals generally come out in this order:

1) Contributions 👉 can be taken out anytime
2) Conversions 👉 generally subject to a 5-year clock
3) Earnings 👉 usually require 59½ + 5 years

This means you don’t have to wait years to access your contributions.

However, once you take that money out, you permanently lose that Roth space, so this is best viewed as an emergency option, not a primary strategy.

But if you needed funds before 59½, you could access the contributions early.

Why is this a big deal?

It gives people pursuing financial independence a potential Plan B source of cash alongside other strategies.

So thank you, angry Twitter guy, for the lesson.

Note: Purely educational, not financial advice.

Shaq blew $1,000,000 in 30 minutes. 

But that mistake set him up for a $420,000,000 net worth. 

One of the best stories you'll hear. 

In Shaq's prime, he got his first endorsement deal.

The payment was worth around $1 million. 

Finally, he got paid! 

So he started with buying a car
$150,000 Mercedes

Then he bought his dad a car
$150,000 Mercedes (same model)

Then he bought jewelry.
Top tailored suits.
Nice stuff.

But of course, he didn't realize he still had payments to make

The taxes for the payout.
The fees for his agents.
And so on. 

Until he got a call from his accountant.

He told him he was $80,000 in the red! 

He describes this as the life-changing moment when his finances changed. 

Notice, it wasn't the moment he got all of his income. 
It was the moment he spent all of it. 

And soon he changed. 
And so did his habits.

Fast forward today, he has a $420 million net worth.

And he deployed his earnings in investments:

- Stocks
- Businesses
- Real estate

No matter where you are, everyone learns about money. 

And usually, the hard way is when it gets you. 

The art is not what you earn, but what you keep!

How are you keeping yours?

Them: We're looking to get a home.

Lender: How much were you looking to borrow?

Them: Well, how much can we?

Lender: 28% of your gross income. 

Them: Awesome. Let's do it. 

......

Them: We need help. How come it feels like we are stuck? We make really good income! 

Advisor: Let's take a look at your finances.

checks it*

Advisor: Well, I've found the problem. Your mortgage is 50% of your net income.

... 

Affording a down payment doesn't mean you can afford a property.

There's more to owning than just the price:

The costs you see. 

The costs you don't see. 

Don't lose sight of them.

Your child could get $1,000 free in a new account.

If your child was born 2025-2028, listen up:

Unofficially called the "Trump Account", here’s what we know so far:

- It’s a custodial Traditional IRA under section 408(a), with modifications
- Created for kids under age 18, with a valid SSN, when elected by a parent or grandparent
- Contribution limit = $5,000/year per child, adjusted for inflation after 2027
- Employers can also contribute up to $2,500 per child as part of a written plan
- Contributions are not tax-deductible
- Investments must track an index, have no leverage, and expense ratios under 0.1%
- Withdrawals not allowed until the child turns 18
- Contributions are treated as basis and not taxed again upon withdrawal
- Earnings are taxed as ordinary income
- 10% penalty applies to early withdrawals before age 59½ unless an exception under IRC Sec. 72 applies

But here is where the value is:

There’s also a pilot program starting in 2026:

Children born between 2025–2028 may be eligible for a $1,000 government-funded contribution if elected by their parents.

This account is new and the rules are still unfolding.

It shares similarities with other accounts like Traditional IRAs, 529s, and Roths, but has its own limitations and planning quirks.

The way to do this is by either:

1) Filing out Form 4547 here: https://trumpaccounts.gov./

2) Or filling out that same form with your tax preparer

These accounts are not expected to be funded before July 4th. 

If you file your 2025 return before that date without signing up on the website, you may have to wait until you file your 2026 return to receive the funds.

More to come as additional guidance is released!

Would you open one for your child?

If you're single on Valentines Day just remember your index funds still love you. 

Index and chill.

If your ESPP has a "look back", you're stting on a wealth hack. 

Here's the opportunity sitting in front of you. 

ESPPs are relatively simple. 

- You set aside your paycheck on a monthly basis for a period of time
- You buy your company stock at the end of the period
- Company let's you buy at a discount (usually 15%)
- The discount puts you at an immediate gain 

There some things to look out for like taxation, liquidity, and blackout periods to see how the ESPP works for you. 

But some have a provision called a "look back" period. 

The discount is applied either at the lower of the enrollment date or purchase date. 

For example:

If the enrollment price was $100 and $50 at the purchase price, the 15% is applied at the purchase price. 

If the enrollment price was $50 and $100 at the purchase price, the 15% is applied at the enrollment price. 

If the latter occurs you are looking at not only at 15% discount, but appreciation already of $50 between the $50 and $100! 

It's one of those great perks that can increase your wealth via your employer benefits. 

Don't discount the value of your company discount!

"I bought this stock cause Tik Tok guru 'StockMaster999' told me to"

Most people don’t actually know the tax status of their accounts.

Quick refresher 👇

Taxable Accounts:

- Individual Brokerage
- Joint Brokerage
- UTMA / UGMA

Pre-Tax Accounts:

- Traditional IRA
- SIMPLE IRA
- SEP IRA
- 403(b)
- 401(k)
- 457

Post-Tax Accounts:

- Roth IRA
- Roth 457
- Roth 401(k)
- Roth 403(b)
- Roth SEP IRA
- 529 (Could have a state deduction)

Triple-Tax:

- HSA (One of a kind)

Before worrying about returns?

Make sure you know how your money is taxed.

Which of these are you using?

Commissions coming with a 6 figure tax surprise?

Well, we commonly hear this misconception:

"My commissions are taxed at a higher rate!"

Not always. Why is it wrong?

Let's look at an example here.

Selling Sally works hard at her job.

She typically gets half in salary and half in commissions.

She’s hit her quota and is excited for those commissions to kick in.

But when she checks her paycheck, she notices something…

Her commissions were "taxed" at a lower rate than her salary.

At first, this seems great, more money in her bank account!

But then, tax season arrives.

After filing her taxes, her accountant lets her know she owes a massive tax bill!

Now she's frustrated that she has to write a big check and wonders:

Did something go wrong with her return?
Did she get taxed more than expected?
Did she get hit with some penalty?
Nope.

She owes more because her employer withheld less than she actually owed.

And that's the key word here: withheld.

Whenever you have monthly income like a salary, it’s considered “regular,” which gets taxed progressively like usual.

But whenever you have irregular income like:

Awards
Bonuses
Commissions
Equity Compensation
Or anything that doesn’t pay monthly
…it’s considered “supplemental.”

And these irregular forms of income are withheld at different flat rates by default.

For commissions, the default withholding is 22% for the first $1 million and 37% for any amount beyond that (Federal rate for 2025).

This is just withholding, not the actual tax owed.

Since Sally makes $500,000, her actual marginal tax rate is 35%.

But her commissions were only withheld at 22%, which wasn’t enough.

So instead of getting a refund, she ended up owing the difference at tax time.

She didn’t pay more for her commissions.

She just had less withheld than owed.

Big difference!

(Sally is a hypothetical example, but you get the point)

57% of workers are contributing to their 401(k). 

But most don't know if theirs is good. Here's what you should know:

The truth is that not all 401(k)s are treated equally. 

Some are good. 

While others are disappointing. 

But the account is not at fault: it's how it's structured. 

Employers create them how they see fit. 

So, what are the top areas to look at?

In my view:

- Whether they limit your contribution limits
- Do they offer a Roth option to you
- Do they offer a match to you
- Do they offer more than a target date
- Do they offer low-cost index options 
- Do they offer an after-tax option that you can convert

The more these boxes are checked off, the better. 

It's not about the account you have. 

It's how you use the account too! 

Do you have a 401(k)?

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

If you love visuals like this, you'll love the weekly money visual newsletter!

Be sure to be subscribed here:

https://lnkd.in/gJC9mTQH

You would need a 1,000% return on a $1,000 portfolio to have the same dollar-for-dollar return as a $100,000 portfolio with a 10% return.  
 
Read that again 👆 
 
It's much easier to accomplish the latter than the former.  
 
But it doesn't have to come simply from high returns.  
 
So if you don't have a 6 figure portfolio yet? 
 
Focus on your savings rate, not returns.

There’s a more tax-efficient way to own an index.

But is it worth it? Here’s a breakdown of direct indexing:

What is direct indexing?

It’s still passive investing.

But instead of owning an index fund, you own the individual stocks that make up the index.

Same market exposure.
Different implementation.

The goal isn’t higher returns.
The goal is tax efficiency.
Index funds are already very tax-efficient, especially ETFs.

But there’s one thing they can’t do:
They can’t pass individual stock losses to investors.

Losses inside a fund stay inside the fund.
With direct indexing, you own each stock directly.

That allows for:

Ongoing tax-loss harvesting
Offsetting capital gains
Deferring taxes while staying invested

Over time, this can increase after-tax wealth even if pre-tax returns are similar.

Some studies suggest direct indexing can add incremental after-tax value over long periods (often cited at 1%–2%), but results vary widely based on volatility, tax bracket, cash flows, and implementation.

Important tradeoffs to understand.
This strategy is not a free lunch.

Here’s what actually matters.

1) Cost

Most platforms charge roughly 0.10%–0.20%.
But additional costs may include:

Trading costs
Cash drag
Tracking error
Etc.

These reduce the net benefit and must be weighed against expected tax savings.

2) New money works best

Selling existing index funds to switch strategies often creates taxes that wipe out the benefit.

Direct indexing tends to work best with new dollars, such as:

Income
Liquidity events
Sale or acquisition proceeds
Using fresh capital avoids unnecessary tax friction.

3) Tax benefits depend on markets

The biggest advantage comes from harvesting losses, which requires volatility.

In prolonged bull markets:
Losses become harder to find
Unrealized gains accumulate

Tax benefits shift from harvesting losses to deferring gains, and eventually decline.

4) Wash sale coordination matters

Loss harvesting must be coordinated across taxable accounts, spousal accounts, and any index funds held elsewhere.

Poor coordination can reduce or eliminate the benefit.

5) You need an exit strategy

Deferred taxes eventually come due unless there’s a plan.

Is this money for retirement, charity, heirs (step-up in basis), or future liquidity?

Direct indexing works best when paired with broader tax and estate planning.

6) Benefits skew toward higher earners

The tax alpha is largest when tax rates and taxable balances are high.

For lower brackets or smaller portfolios, added cost and complexity may outweigh the benefit.

Bottom line

Direct indexing isn’t a magic upgrade.
It’s a tax optimization tool.

For the right investor, at the right time, with the right plan, it can add meaningful after-tax value.

For others, a low-cost index fund may be the better answer.

That’s why this should be a planning decision, not a product pitch.

If you’re exploring it, talk with a fee-only planner to see if it actually fits your situation.

taplio

The Battle

Seth Yakatan

Max Pashman, CFP®

Followers

Posts

Engagements

Likes

Performance ScoreSeth Yakatan's LinkedIn Performance

Performance ScoreMax Pashman, CFP®'s LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Seth Yakatan

Max Pashman, CFP®

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Seth Yakatan's LinkedIn Performance

Performance ScoreMax Pashman, CFP®'s LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreSeth Yakatan's LinkedIn Performance