S Brian Smith 🪜

Strategy Ladders

At Strategy Ladders, we specialize in driving explosive growth for agencies, consultancies, and B2B service businesses.

Our mission: help founders like you scale from 7 figures to 8 figures and beyond, unlocking your business's full potential.

We work with founders ready to accelerate growth, overcome operational bottlenecks, and build a business that can scale rapidly and sustainably. If your business isn’t achieving 200% year-over-year growth, it’s time to rethink your strategy.

The Strategy Ladder System is designed to do just that. It’s a proven framework that delivers a bulletproof strategy tailored to your business’s unique needs. Our system streamlines operations, drives revenue, and positions your business for sustained, long-term growth.

But we don’t just stop at strategy. We execute.

Our team of 8-figure founders and industry experts ensures every aspect of your business is optimized for scalability. From marketing and sales to operations and leadership, we cover it all—making sure your business is set to thrive as it grows.

Our results speak for themselves. We’ve helped over 1,000 entrepreneurs achieve remarkable success, including:

💥 Scaling an agency from $150k to $4M ARR in just 10 months

💥 Boosting a digital marketing agency’s productivity by 450%, dramatically increasing profitability

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

💥 Repositioning a web development agency to secure a long-term contract with a Fortune 100 company

💥 Growing an app development agency’s recurring revenue from 2% to over 50% of total revenue in three months

💥 Building a sales organization of 65 people in two years

💥 Orchestrating the sale of key SaaS platform assets at a significant premium over market value

If you’re serious about scaling to 8 figures and beyond, let’s connect. We’re here to provide the expertise and execution you need to achieve exponential growth.

Founder & CEO

I host Strategy Ladders, a no-nonsense podcast delivering real-world insights on scaling, optimizing, and thriving as a founder of an agency or B2B service company.

With 17+ years in the field, my team and I tackle core challenges in B2B sales, leadership, and business growth to help owners overcome bottlenecks and build high-performing teams. Think of it as having an outsourced co-founder in your corner, sharing tactical strategies on everything from digital marketing to operations—minus the fluff. Ready to put your business back to work for you? Follow us now!

Available on YouTube, Spotify, Apple Podcasts, Google Podcasts and Amazon 🎙️

Podcast Host

Trivr Eats, Inc

Advisor

S. Brian Smith Group, LLC

"Simply put, Brian has an innate ability to cut through all the bullshit/programming/stories and help one identify and achieve their goals. Working with him has made me more successful in business and has had an overwhelmingly positive impact on my personal life." - Serial Founder & Investor

"S. Brian Smith changed my perspective on life. In fact, he just changed my life - full stop. I’m a better person because of the work we’ve done and I will continue to grow because of the way he has taught me to think." - Entrepreneur, Founder, Executive

"Brian's ability to, not only think outside of the box, but to help me approach various situations from multiple angles is simply, genius. His approach is methodical, authentic, and most importantly, leads to tangible results." - Fortune 500 Executive

"S. Brian Smith is the best damn coach I have ever worked with." - Entrepreneur

Business & Mindset Super Coach to Entrepreneurs

Forbes Coaches Council

Founding Member

Institute of Coaching, McLean/Harvard Medical School

The Institute of Coaching, McLean/Harvard Medical School advances research and education in coaching by bringing together leaders in the field to accelerate research progress and disseminate coaching's best practices.

Fellow

Unicorn Puff

Unicorn Puff is a brain trust of experienced entrepreneurs who help B2B agencies grow. We work with B2B service agencies who are ready to grow. If you’re stuck in one of these spots, we’ll help you take your agency to the next level:
- Founders who are focused on sales, rather than building the business
- Revenue growth has stalled or plateaued
- Despite outbound efforts, most of your sales come from referrals

Chief Executive Officer

Have2Have.it

Chief Marketing Officer / Chief Strategy Officer

Soldsie

Social Kapture

Chief Strategy Officer (CSO)

The Founders Organization

Conceived, built, and operated a paid membership group with 1500 founders throughout North America. Responsible for organizing and executing events in 35 cities throughout North America and large activations at SXSW.

COO / Head of Strategy

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

Are you a founder of a B2B service business or agency generating $2.5 million to $25 million in revenue?

You've tasted success, but you know there's more potential.

You believe your business can reach 8 figures and beyond, but...

😒 You’re the primary strategist for clients.  
😧 You lack a high-level operations leader.  
😖 You’re the main revenue driver.  

You’re exactly who we help.

Imagine a business that thrives without you. A business where your team drives growth, not just maintains it. A business that gives you freedom—not more stress.

❌ Your team struggles to run the business without you.  
❌ Your growth isn’t on track to meet your goals.  
❌ Your team is solid but not equipped to scale to the next level.

It doesn’t have to be this way.

At Strategy Ladders, we’re not just another option—we’re the only serious option for founders ready to scale their 7-figure business to new heights. Our team is unparalleled—every strategy advisor is an 8-figure founder who’s been in your shoes, scaled their businesses, and knows how to help you achieve explosive growth.

Our program provides direct access to a handpicked team of world-class experts in marketing, sales, operations, project management, finance, HR, and more. These aren’t just consultants—they’re industry leaders who’ve built, scaled, and exited businesses like yours.

With Strategy Ladders, you’ll do more than scale from 7 figures to 8 figures—you’ll transform your role in the business. You’ll step out of the daily grind and into true business ownership, where your business works for you, not the other way around.

Here’s what we deliver:

✅ A growth system that injects rocket fuel into your business 🚀  
✅ Strategies that make your business work for you, not the other way around 💎  
✅ Freedom from being irreplaceable ⛓  
✅ A clear path to becoming an owner, not just an operator 💪  
✅ Maximizing the value of your business 💰

Our results speak for themselves:  
"Working with Strategy Ladders has transformed my business and my outlook on life. Their expertise and insight are unparalleled."

"Thanks to Strategy Ladders, I went from 60-hour workweeks to 40, with a clear plan to reduce further. Their guidance is worth every investment."

If you’re ready for exponential growth and a real transformation in your business and life, let’s talk.

One final note: We’re not here to make you corporate. We challenge the status quo, and we will challenge YOU to achieve greatness.

🪜 Visit www.strategyladders.com to schedule a call and discover how we can elevate your business to the next level.

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

Pashman Financial LLC

I help sales reps and equity compensated employees to make sure they don't spend their entire commission check in the Bahamas. Putting tailored plans together to put a purpose behind their paychecks. You worked hard for your commission check. Now make it work as hard as you did to earn it.

Made the shift from fee-based to fee-only in an effort to better serve clients.

Financial Planner (Fee Only)

One Wealth Management Financial & Insurance Services

•Examining client's expenses, income, insurance coverage, financial objectives, tax status, risk tolerance, or other information needed to develop a financial plan.
•Answering client questions about financial plans and strategies and giving financial advice.
•Advising strategies for clients in investment planning, insurance coverage, cash management and other areas to help them reach financial objectives.
•Reviewing client accounts and plans on a regular basis to understand if life or economic changes, situational concerns, or financial performance necessitate changes in their plan.
•Analyzing financial data received from clients to develop strategies for meeting clients' financial goals.
•Preparing or interpreting financial document summaries, investment performance reports and income projections for clients.
•Implementing financial plans or referring clients to professionals who can help them.
•Managing and updating client portfolios.

Financial Advisor

Northwestern Mutual

General Support:
– Transcribing and/or processing dictation , processing correspondence, maintaining client case files, and filing performance reports, account forms, and other advisory paperwork
– Maintaining annual review notes and mailing annual review letters to clients;
– Monitoring and stocking marketing materials for Signature advisory programs
– Monitoring industry trends and research
Proposal and Case Preparation:
– Prospecting on behalf of the employing WMA for new clients
– Preparing and modifying PPA/PNA’s and investment/advisory proposals
– Preparing investment policy statement, needs-based analysis, or financial plan
– Recommending fund portfolio options.
Processing Accounts:
– Preparing and processing all paperwork needed for investment/advisory accounts;
– Monitoring, processing, and following up on asset transfers and on initial and subsequent funding of advisory accounts;
– Implementing initial and subsequent asset allocation trades
– Identifying need for switch letter and mailing appropriate forms to clients; discussing potential rollover opportunities from other retirement plans for variable and mutual funds
– Monitoring holdings for program eligibility and administering advisory accounts.
Advisory Client Meetings:
– Meeting with advisory clients for fact finding and conducting existing advisory client reviews
– Completing risk tolerance (personal profile) questionnaire with client
– Participating in client meetings for financial or investment plan development or presentation
Client Service:
– Corresponding with clients to handle advisory-related service issues
– Contacting clients on behalf of the Wealth Management Advisor for the purpose of developing advisory plan
– Formulating advisory product solutions to/for a client or explaining advisory products or advisory performance
– Accepting redemptions/withdrawals from clients and communicating instructions to home office;
– Discussing tax consequences, costs, and advisory fees

Associate Financial Advisor

Investor Relations Partners

-Investor relations and financial communications created to assist clients address valuation. 
-Development of earnings communications, press releases, corporate presentations, financial strategies, professional profiles, fact sheets, annual/quarterly shareholder reports, investor targeting , perception studies, investor conferences, and media relations.
-Always cooperating and involved with assistance during unexpected shocks/crises with management and provides next-step strategic approaches.
-Contacts top publications nationwide to arrange interview with client in order to increase exposure and market valuation on Wall Street

Investor Relations Representative

Julep Bar

-Provide appropriate music for a specific nightlife audience
-Promotion and organization of events through social media
-Responsible for lighting configuration, sound check, and preparing equipment for the venue
-Assistance with booking artists and popular figures

Event Planning Assistant

Cedars-Sinai

- Responsible for transferring and organizing 20 years worth of cases
- Lead research, planning and development of comprehensive digital programs
- Work with a social media team to develop and manage ongoing media marketing plans for  campaign
- Participated in research through Spinal Journal
- Proficient with syndicated research and social media monitoring tools with ability to use these tools to inform ad and campaign design.

Assistant

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.

Helping Founders and Executives Plan for Early Retirement and Exit

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*

pashman-financial-llc

schooloffinances

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Sales Navigator

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

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

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!

"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.

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.

Make too much income for a Roth IRA? 
 
Here's how to get around it (legally) 
 
First, what's the problem? 
 
The Roth IRA is a great vehicle for tax-free growth. 
 
But there are income limitations. 
 
For 2025, those limitations are as follows: 
 
$150,000 for single filers 
$236,000 for married filing jointly 
$0 married filing separately
 
Make above these amounts? 
 
They get phased out or entirely ineligible. 
 
So what to do? 
 
Instead, you could contribute to the Traditional IRA. 
 
But are you contributing to a 401k? 
 
Those deductions might also phase out! 
 
This seems like a lose-lose scenario. 
 
But it opens for an opportunity. 
 
The good news is that you can use the IRA to fund a Roth IRA. 
 
This is known as a Backdoor Roth IRA. 
 
Here's what you could do: 

FIRST: Move all existing IRA money into an employer plan like a 401k. 
 
1) Open a Traditional IRA & Roth IRA 
2) Fund the Traditional IRA 
3) Do NOT invest the funds 
4) Initiate a Roth Conversion into the New Roth IRA 
5) Elect not to withhold taxes 
6) Invest in the Roth IRA 
7) File Form 8606 to show non-deduction in Traditional IRA 
 
This process is why having a Roth 401k is pretty handy: you can make any contribution with no income limitations. 

Remember, this is purely educational and is shown here for simplicity.
 
This is not financial or tax advice, so please consult with a financial and tax professional first.
 
But the door is open for tax-free money!

You've gotta find the right key.

Note: This is purely educational and not financial or tax advice. Seek a professional before acting on any of the information.

Helping Founders and Executives Plan What’s Next After Their Exit

Today: Shirt worth $100

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

 What a steal.

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.

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.

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!

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.

We’ve been raised on broken financial advice: 
 
- Don’t buy $5 coffee 
- Keep everything in the bank 
- Don’t be reckless with any investments 
 
Instead should be this: 
 
- Buy what you value 
- Allocate your money based on your goals 
- Take risks that are aligned with who you are 
 
There’s a reason they put the word “personal” in front of finance. 
 
It’s supposed to be tailored to YOU.  
 
Do what works for you.

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.

Dear LinkedIn,

Show everyone's impression count. 

Sincerely, 
Literally Everyone

64% of adults fear outliving their money more than death.

But most haven't heard the 4% Rule. Here's how it works:

It was a rule created to help retirees determine the amount they can take out.

It was intended to give people a guideline on what to aim for. 

The rule is pretty straightforward. 

In the first year, take out 4% of the portfolio. 

Then adjust that dollar amount for inflation annually after. 

It was originally tested with a couple of parameters:

- For a 65 year old (25-30 year retirement)
- Allocation with 50% stocks / 50% bonds
- Tested in a worst-case scenario

Using historical data, the rule was determined to give retirees a safe number to stick with. 

Is it completely flawless?

Not entirely. 

Many things can have an impact like:

- Inflation
- Economy moving forward
- Your unexpected variables to your situation

This is why the 4% rule is more of a reference than a final say. 

But it is a great guideline for a quick calculation to see your number. 

In reality, you will need a financial planner to help you out here. 

You need to evaluate variables such as:

- The timing of your retirement
- How long your retirement will be
- How your portfolio will be allocated 
- What other sources of income do you have
- What is the economy in your first year 
- What other goals will impact it
- And much, much more

When you need a quick number, you can use this freely.

But when you need the answer to work for you?

Seek a consultation from a financial planner. 

We're here to help when you're ready!


And if you want to see more helpful visuals like this, check out the newsletter with more details behind how they can help you.

Check it out here:

https://lnkd.in/gJC9mTQH

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?

taplio

The Battle

S Brian Smith 🪜

Max Pashman, CFP®

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taplio

The Battle

S Brian Smith 🪜

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);}Max Pashman, CFP®'s LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreMax Pashman, CFP®'s LinkedIn Performance