S Brian Smith 🪜

I free founders from ops, sales, & management | Founder @ Strategy Ladders | Coached 1000s of B2B and Agency owners | Stop struggling, start enjoying business ownership 🏖️

Most founders of 7-figure B2B service companies reach a plateau where "strategy" isn't the problem—execution is. After years of consulting on the "how," my team and I shifted exclusively to building and running these high-growth engines for you.

Strategy is often used as a shield to avoid the hard, grinding work required to scale. Scaling to 8 figures requires two things: Great Lead Flow and an Excellent Team to execute it. Without these, your strategy is just a dream.

We have traded playbooks for performance, focusing on three specific levers:


➡️ Cold Email (B2B Labs) We deploy enterprise-grade outbound infrastructure that in-house teams can't match.

Scale: 10,000+ emails per week without risking sender reputation.

Performance: 40%+ open rates and $17.5M+ in revenue directly attributed to outbound.

Targeting: Hyper-targeted lists verified to ensure you only speak to high-intent prospects.


➡️ Google Ads (B2B Labs) Capture buyers actively searching for your solutions right now.

High Intent: Focus on decision-maker search targeting and aggressive negative keyword strategies.

Speed: Immediate visibility for high-intent keywords without waiting for SEO.

➡️ Modern Recruiting (Talent Labs) Hire faster and better without traditional placement fees or job-board spam.

Speed: We deliver an exceptional candidate shortlist in 7–14 days.

Vetting: Every candidate is screened for skill, motivation, and culture fit.

➡️ A Selective Approach to Consulting I still provide 1:1 consulting, but only for founders who can prove they have, or are able to build, the team and lead flow necessary to scale. People are no longer willing to pay for strategy without execution. And I’m no longer willing to provide it.

Build your engine: www.strategyladders.com

Founder & Head of Strategy

The Strategy Ladder Program delivers MASSIVE results to agencies, consultancies, and service businesses.

If your business is 25-85 employees, partially or fully remote, and you're stuck trying to "level-up," I will transform it with you.

The Strategy Ladder System will get you UNSTUCK. You'll develop a bullet-proof strategy that grows with your business, streamlines operations, scales your revenue, and sets your business up to continue to grow without you.

The Strategy Ladder System doesn't just change your business. It will transform YOU. You'll undergo a mental reset that frees you from the anxiety and beliefs that tie you to the day-to-day in your business. You're the leader of your business - if you don't change, your business never will.

The Strategy Ladder System has worked for over 400 entrepreneurs, delivering & implementing strategies that have:

💥 Scaled an agency from $150k to $4mil ARR in 10 months

💥 Increased a digital marketing agency’s productivity levels by over 450%, dramatically increasing profitability

💥 Streamlined a SaaS product’s roadmap, reducing development costs by 45% while increasing execution speed by over 25%.

💥 Developed and executing a repositioning strategy that landed a web development agency a long-term contract with a Fortune 100 company

💥 Repositioned of an app development agency that grew recurring revenue from 2% to over 50% of total revenue within three month

💥 Built a sales organization of 65 sales people in two years

💥 Orchestrated & executed a legal & and business strategy that lead to a sale of key assets of a SaaS platform for a significant premium over the market value of the company

Elon Musk Didn’t Build Tesla. He Built a Story.

🔹 2004: Musk invests in Tesla but isn’t a founder. In 2009, he sues the actual founders until they’re legally forced to call him one.

🔹 2013: He announces Hyperloop, claiming it will revolutionize transportation. Over a decade later, nothing exists. He later admits it was just a stunt to stop California’s high-speed rail project.

🔹 2016: He promises full self-driving Teslas by 2017. In 2019, he claims 1 million robotaxis will be on the road by 2020. It’s now 2025—still waiting.

🔹 2014: Tesla showcases battery swap technology, claiming it will allow instant recharging. Never happens—but they get millions in government subsidies anyway.

🔹 2020: Musk personally vows to fix the Flint water crisis. That didn’t happen either.

And yet, people still believe him.
Because story beats reality.

🚀 His companies miss deadlines by years (or forever), but investors stay excited.
 🚀 He fakes demos and sells visions, and people line up to give him money.
 🚀 He turns PR disasters into proof of his genius.

For founders, here’s the takeaway 👇

Execution matters, but narrative moves markets.

You can have the best delivery in the world, but if you don’t own the story, someone else will.

Story beats reality. Musk understands that better than anyone.

Now, the real question: do you?

Do you agree that story trumps reality? Or do you realize it's true but it makes you ick... 

Drop your take below. ⬇️


✌️🧡🌮

Plug & Play Growth Engines to get you to 8 Figures | Cold Email ($17.5M+ Generated) | Google Ads | Elite LATAM Recruiting (7-14 Day Shortlists). Strategy is dead ☠️ execution is everything 🚀

Most founders don’t validate offers. They decorate them.

Most founders “test” a new offer like this:

- Rewrite the website
- Post 12 times on LinkedIn
- Debate the pricing for 3 weeks
- Call it “market research”

That’s not testing.

That’s hiding.

If you're not actually getting in front of customers.
It's just a "wait and see" approach.

Cold email is one of the fastest ways to test a new offer in the real world.

New messaging. New ICP. New angle.
In-market feedback in days, not quarters.

Why cold email is the perfect offer test

Because it forces the only questions that matter:

- Do they care? (opens + replies)
- Do they understand it? (clarifying questions vs “sounds cool”)
- Do they want it now? (calls booked + urgency)
- Is the price insane? (pushback, negotiation, ghosting)

3 real examples

1) New ICP test (same service)
You run a dev shop. You want to shift from “anyone who needs code” to Series A B2B SaaS with messy onboarding.

Email 50 heads of product.

If 10 reply with “this is literally our problem” - you’ve got something.
If 0 reply - it’s not the ICP. Or your hook sucks. Either way you know fast.

2) New angle test (same ICP)
You sell paid media. You’re torn between:

“lower CAC”
“fix lead quality”
“speed to pipeline”

Run 3 mini-campaigns: same ICP, different promise, 100 prospects each.

Whichever gets the highest *positive reply rate* wins.
Not likes. Not vibes. Not your opinion.

3) New offer test (new packaging)
Instead of “retainer”, you pitch a 14-day Sprint:

Audit + plan
1 campaign shipped
KPI targets
fixed fee

If prospects say “love the sprint, what’s next?” you’ve got a wedge into the longer engagement.

How to test an offer in 7 days

Day 1: Pick ONE variable
Don’t change everything at once.
Choose one:

- ICP
- Pain
- Promise
- Offer format (sprint vs retainer)
- Price point

Day 2: Build a tight list (200-500 people)
Specific beats big.
Example:
“VP Ops at 50-300 person logistics companies using NetSuite”
not “ops leaders”

Day 3: Write 3 hooks
Each hook is one sharp “they care about this” claim.

Examples:

“Most agencies don’t have a lead problem. They have a follow-up + capacity problem.”
“Your funnel isn’t broken. You’re multiplying zero.”
“You’re one resignation away from chaos - and you feel it.”

Day 4-6: Send 50-150/day
Keep volume clean. Track replies manually if you have to.

Day 7: Read replies like a scientist
Categorize every reply into:

- Yes / interested
- Not now
- Wrong person
- We do this already
- Confused
- Hostile

Then adjust ONE thing and run it again.

What “good” looks like (simple scorecard)

- If you can’t get 1-3% positive replies, your offer isn’t landing (or your list is trash).
- If you get replies but no calls, your CTA or proof is weak.
- If you get calls but no closes, your offer/price/positioning needs tightening.

Cold email isn’t just lead gen.

It’s a lab.

You can find out what the market wants… while everyone else is “building the funnel.”


✌️🧡🌮

Mexico is a war zone... only if you believe the news.

I've lived in Mexico for 5+ years. I'm a US Citizen and permanent resident of Mexico.

It is 1450% safer here as a US citizen than ANY major US city (more below). The citizens & police are friendlier and more helpful.

Every single US citizen who visits me is shocked at how safe they feel here, walking the city, especially at night.

What you are seeing on the news = PROPAGANDA.

Mexican news sources and some of my well connected friends all confirmed the involvement of US special forces in the "removal" of El Mencho.

The US is involved.

The timing is not an accident.

Just take a look at the USD vs Mexican Peso graph.

The US has been losing purchasing power since January.

Mexico is preparing for the World Cup.

The US has a strong history of disrupting the economies to the south of them. 

Recall 1997... Cuba's hospitality industry was fast growing and Cuban "dissidents" (aka absolutely not CIA 🙄) launched a 💣 campaign against Cuban hotels.

What you're hearing about in Mexico is no different.

Mexico has taken a slower approach of disrupting the cartels.

Why?

If you cut off the head of the snake, many smaller ones appear.

But they aren't organized. What you're seeing now will disappate.

What the US news isn't telling you?

The cartel members are clearing out civilians before creating chaos.

It's well known - there are severe consequences for harming a civilian. It rarely happens.

Here's the stats that the US isn't telling you:

78% of firearms seized in Mexico come from the US.

Over 90% of the drugs that flow through Mexico are consumed by US consumers.

There's been a 75% reduction encounters with drug runners at the US boarder due to the crackdown in Mexico.

So what's the real problem?

It's not Mexico.

It's the US fueling the violence... violence that largely, if not entirely, spares civilians.

More stats:

< 0.1% - The percentage of tourists & expats who experience violent crime in Mexico.

1.45% - The percentage of people in the US who experience violent crime in the US.

You are statistically 14.5 times more likely to be a victim of violent crime as a US Citizen in the US.

Don't believe what you are reading or seeing in the news and social media.

Sensationalism draws eyeballs. The truth is far less interesting.

What you're witnessing is an attempted assassination... of the Mexican economy.

Come at me in the comments güey 👊

Viva 🇲🇽

If you think your $1,000/month “EA” is going to unlock your calendar and scale your business…

You’re LARPing as a CEO instead of leading.
You didn’t hire an Executive Assistant.

You hired a Virtual Assistant with a fancier title and a broken job description.

And now you’re wondering why you’re still stuck reviewing your own travel itinerary, juggling Slack messages, and chasing your tail in ops hell.

Let’s fix that.

🧠 First, understand the difference:

Virtual Assistant (VA):

• Task-taker
• Needs clear instructions
• Good at executing a known to-do list
• Will take 2–5x longer to do a task you could do in your sleep
• Great for clearing clutter
• A clone hire (not a growth one)

Executive Assistant (EA):

• Strategic partner
• Anticipates needs you didn’t vocalize yet
• Handles ambiguity
• Adapts to your working style and makes you sharper
• Enables you to operate in your zone of genius
• A force multiplier, not a checklist completer

If you’re hiring an EA and getting VA output…
That’s disappointment on a payroll. Don’t call it delegation.

Many founders fail at this because they’ve never had a real EA before.

🛠️ So how do you fix it?


Step 1️⃣ : Stop being vague.

Write a real role description.

→ Is this person handling your inbox or planning investor roadshows?
→ Do they need to coordinate between departments or just book travel?


Step 2️⃣: Hire for initiative, not obedience.

A good EA doesn’t wait for permission. They preempt chaos and build order.


Step 3️⃣: Pay what the role is worth.

You want a $100K partner to run point on your calendar, communications, and priorities?

Then don’t shop for bargain-bin help with champagne expectations.


Step 4️⃣: Give them context, not just commands.

Your EA needs to know your rhythm, your goals, your blind spots.
The best don’t just manage your tasks, they manage your attention.

Founders: You don’t need more hours.
You need more clarity.
And the right assistant is the unlock for both.

Start treating the EA role like a leadership hire not a tactical afterthought.


👉 Ready to hire an Executive Assistant who will transform your work and life?

We have pre-vetted, highly experienced, Executive Assistants ready to go. 

Our matching process delivers EA's that are primed for success in your organization and our on-going support and guarantee ensures you get results that matter to you.

DM me to get started.


✌️🧡🌮

I built a business I am proud of, but I stopped doing the work I was made to do: the work I love most and do best.

I have spent too much time building the machine and not enough time doing the work that lights me up.

For over a decade, I worked 1:1 with entrepreneurs and high performers to help them overcome the biggest challenges in their lives and businesses.

Mental blocks. 

The mindset shifts required to reach the next level.

Relationship challenges.

Understanding themselves more deeply and how that version of them can make the greatest impact in the world.

Developing and trusting intuition.

Learning how to stop playing checkers and start playing chess. In life and in business.

And, of course, business strategy.

I love that work.

And I am really, really damn good at it.

But truthfully, I got caught up in building Strategy Ladders.

I still run Strategy Ladders, and I am proud of what we have built.

But somewhere along the way, I hired consultants and coaches to work with clients, got a little too much ivory tower syndrome, and became overly focused on running the business instead of doing the work that truly lights me up.

It is time to change that.

I am taking on 3 private 1:1 clients for the next 3 months.

This work is about massively shifting your mindset, breaking through barriers, and putting you on a faster path toward the life and results you know you are capable of.

Nothing is off limits.

Business is always part of the conversation, but business is rarely the full story.

Your business is a mirror. It shows us where to look.

I have walked clients through partnership breakups, births, deaths, PR crises, divorces, business sales, and the mindset shifts required to navigate all of it powerfully.

If you are ready to face challenge with deeper energy, sharper thinking, and a new level of self-trust, now is the time.

DM me.

Or comment SHIFT below.


✌️💛🌮

If your leads doubled next month, would you grow or crash?

Most $2.5M to $25M service businesses are brittle in one of two ways.

They can sell, but delivery breaks.
Every new deal creates chaos, churn, and margin leaks.

Or they can deliver, but pipeline breaks.
The team gets quiet. The founder starts “testing ideas” again.

Scaling is not vibes.
It is boring math.

Predictable demand.
Execution capacity.

Quick doubling test:

Can you create 10 new sales conversations every week on purpose?
If your best operator quit tomorrow, do you still ship on time?

If either answer is no, that’s the bottleneck.
Not your website.
Not your brand.
Not your “strategy.”

What breaks first in your business if demand doubles in 30 days?

Most founders at $2.5M to $25M think they have a growth problem.

They're wrong.

They have a clarity problem.

They can’t answer 2 questions clearly:

1. What is our ONE growth constraint right now?
2. What is the next 30-day move that fixes it?

So they default to motion:

New web site.
New service line.
New hire.
New software.
New “strategy.”

None of that is strategy.

Here’s the fast diagnostic I use:

If you had to grow 30% in the next 90 days, what breaks first?

A) Demand (not enough qualified conversations)
B) Conversion (calls happen but they don’t close)
C) Delivery (you can sell it but can’t ship it cleanly)

Most teams are stuck because they try to solve all three at once.
That’s how you get expensive and average.

The play is boring and effective:

Pick the constraint.
Run one lever hard for 30 days.
Measure strictly.
Then stack the next lever.

👉 If you’re A (Demand):

Cold email is still the fastest way to manufacture qualified conversations on purpose.

👉 If you’re C (Delivery):

You need execution capacity and redundancy so growth doesn’t feel like a hostage situation.

A strong LATAM team is the highest value move I see for that.

Now the big one....

👉 If you’re B (Conversion):

You don’t have a lead problem. You have a “this isn’t an obvious yes” problem.

Two fastest fixes:
1. Increase lead intent

Paid ads can work here if you already know:

who you serve
what you sell
what you charge
what “good fit” looks like

Not because ads are magic.
Because they let you buy attention from people already searching.

2. Improve the offer and positioning

Most founders try to “sell harder” on calls.
The real win is making the offer easier to buy.

The tell:
If prospects say “sounds good, I need to think” you have ambiguity, not objections.

My favorite way to fix this fast:
Use cold email as a positioning lab.

Test:

niche language
pain language
outcome language
proof angles
pricing anchors

Until replies and booked calls spike.

👉 What’s your main constraint right now (A / B / C)? 


(don't worry, Shark got some steak 🥩)



✌️🧡🌮

A bee does not waste its time trying to convince a fly that honey is better than 💩💩💩.

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!

Helping Founders and Executives Plan for Early Retirement and Exit

You could skip your annual $7,500 vacation with your family.

Instead, you could contribute to a Roth IRA.

At an average 7% return, over 30 years, that $7,500 annual could grow to about $708,000.

By skipping it, you’d be closer to your retirement.

But there’s one problem.

You traded moments with your family for a bigger portfolio.

Your children will be yours forever.

But they also won’t be kids forever.

For some families, prioritizing these moments matters more.

Because what good is a retirement if it means sacrificing the life you care about along the way?

Most people focus on return on investment (ROI).

We try to focus on something else.

Return on life.

ROL.

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pashman-financial-llc

schooloffinances

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?

Your RSUs are income not investments
Your RSUs are income not investments
Your RSUs are income not investments
Your RSUs are income not investments
Your RSUs are income not investments

There's a reason it has "compensation" in equity compensation. 

It's because they are treated just like your cash. 

Don't believe me?

When they vest, check out your W2. 

It's listed right there next to your salary (your cash compensation).

They may be withheld differently, but it's taxed just the same as income when it comes to tax season.

If you leave it as is, sure it's equity that be treated as an investment. 

But the moment you get it? May as well be just like your cash compensation.

So if you don't know what to do, answer one question instead:

"If this was cash instead of equity, what would you do with it"?

Would you save it?
Would you spend it?
Would you invest it?
If you invested, where?

Your answer really dictates how you should reallocate it.

Especially based on...drum roll please*.... your goals! 

You're already taxed on it when it's fully vested.

Your choice of what to do from there.

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.

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.

"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.

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!

Most have no clue what a write-off does.

Here's a quick breakdown of what it is:

A write-off is merely a deduction.

So use the example:

→ You get a $20,000 expense to write off
 → If your income starts at $200,000?
 → It gets lowered to $180,000
 → So what does that mean?

Here's what it does not mean:

IT DOES NOT MEAN $20,000 LESS TAXES.

A deduction does one thing:
Reduces income taxable.

In this case, a single person in 2025:
(Using only federal taxes in this example)

→ The entire $20,000 is in the 32% bracket
 → The amount taxed? $6,400 federal
 → So with the taxes saved?
 → You netted - $13,600

So yes, you saved more in taxes.

But you still spent money in the end.

It's not a dollar-for-dollar save.

It's a reduction in income taxed.

Big difference!

Note: Post is purely educational and not financial or tax advice*

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?

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.

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.

40% of business owners aren’t sure they picked the right entity.

Here's what you need to know about entity structure:

When choosing a tax entity, you gotta choose with what aligns with you.

Some of the characteristics include:

→ What legal protection is provided
→ Is the income earned a pass-through
→ Are there self-employment taxes 
→ How much admin is there
→ What are the tax impacts 
→ Is there double taxation
→ How much does it cost

And so on. 

Consulting with the combo between a CPA and CFP is a great way to make sure you are on the right path here!

What kind of business do you currently have?

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

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Be sure to be subscribed here:

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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 feel like I've seen these phases with early reitrees:

Stage 1: They fire their advisor cause they don't like performance or service
Stage 2: They do it themself and are happy with it
Stage 3: The more they research, the more they realize there's more to just investing
Stage 4: They keep getting conflicting answers to from thousands of voices online, but unsure which applies to them
Stage 5: They hire a financial planner for a second-hand opinion 

And guess what?

That new advisor is not the person trying to sell them some fancy product or performance.

It's the advisor who:

- Looks at their whole picture
- A structure to implement it
- Has an incentive to do so

I love it when people are able to handle finances on their own. 

But once you need some help?

You know where to find us.

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?

If the recent 4,000 employees laid off by Block caught your attention, this is your wake-up call to revisit your emergency fund. 

Not your retirement accounts.
Not your brokerage accounts.
Not your company equity.

Your cash. 

Yeah, the boring cash loses to inflation over the long run.

But in the short run:

- Easily accessible
- Removed from market volatility
- Not taxed when withdrawn or liquidated

How much to fund is how you answer this question:

"How long can I reasonably live off my essential expenses?"

Just understand this about the stock market. 

It carries a risk of losing money, no matter how long you park it for.

But the longer you have it, the chances of that are cut significantly.

Not "eliminated", but the risk of losing money is statistically lower. 

That risk is put on full max if you need it now. 

The S&P 500 is not a viable fund in the near term. 

The asset that remains fixed near term is. 

Adjust accordingly!

The top 10 issues I commonly see tech employees make:

- Overlapping near identical index funds
- No strategy to maximize profit from their ESPP
- Contributing to a Roth IRA over the income limits
- Treating RSUs explicitly as investments, not as income
- Completing a Backdoor Roth while having pre-tax funds in IRA
- Maxing out their 401(k) all at once without having a "true up" provision
- Exercising ISOs too soon after leaving their company
- Treating their Roth IRA contributions as their e-fund
- Overcontributing to a 401(k) due to job changes
- Not taking advantage of their 401(k) match

What are some mistakes you've been seeing?

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