W. Benjamin Long

[W. Benjamin Long @wbenjamin_1]

Special person Elon is.

[Mike Netter @nettermike]

This article was written by a 26 yr old college student by the name of Alyssa Ahlgren, who's in grad school for her MBA. What a GREAT perspecitve..👍🏽

My Generation Is Blind to the Prosperity Around Us!
I'm sitting in a small coffee shop near Nokomis (Florida) trying to think of what to write about. I scroll through my newsfeed on my phone looking at the latest headlines of presidential candidates calling for policies to "fix" the so-called injustices of capitalism. I put my phone down and continue to look around.

I see people talking freely, working on their MacBook's, ordering food they get in an instant, seeing cars go by outside, and it dawned on me. We live in the most privileged time in the most prosperous nation and we've become completely blind to it.

Vehicles, food, technology, freedom to associate with whom we choose.These things are so ingrained in our American way of life we don't give them a second thought.

We are so well off here in the United States that our poverty line begins 31 times above the global average. Thirty One Times!!!

Virtually no one in the United States is considered poor by global standards. Yet, in a time where we can order a product off Amazon with one click and have it at our doorstep the next day, we are unappreciative, unsatisfied, and ungrateful. ??

Our unappreciation is evident as the popularity of socialist policies among my generation continues to grow. Congresswoman Alexandria Ocasio-Cortez recently said to Newsweek talking about the millennial generation, "An entire generation, which is now becoming one of the largest electorates in America, came of age and never saw American prosperity."

Never saw American prosperity! Let that sink in.

When I first read that statement, I thought to myself, that was quite literally the most entitled and factually illiterate thing I've ever heard in my 26 years on this earth. Many young people agree with her, which is entirely misguided.

My generation is being indoctrinated by a mainstream narrative to actually believe we have never seen prosperity. I know this first hand, I went to college, let's just say I didn't have the popular opinion, but I digress.

Why then, with all of the overwhelming evidence around us, evidence that I can even see sitting at a coffee shop, do we not view this as prosperity? We have people who are dying to get into our country.

People around the world destitute and truly impoverished. Yet, we have a young generation convinced they've never seen prosperity, and as a result, we elect some politicians who are dead set on taking steps towards abolishing capitalism.

Why? The answer is this,?? my generation has only seen prosperity. We have no contrast. We didn't live in the great depression, or live through two world wars, the Korean War, The Vietnam War or we didn't see the rise and fall of socialism and communism.

We don't know what it's like to live without the internet, without cars, without smartphones. We don't have a lack of prosperity problem. We have an entitlement problem, an ungratefulness problem, and it's spreading like a plague."

[W. Benjamin Long @wbenjamin_1]

What a game! Bosh magic

[W. Benjamin Long @wbenjamin_1]

@TheChiefNerd Such a bad take. Maga doesn’t mean Trump turns a blind eye to all bad actors in the world. Peace through strength. Fully support the President here.

[Keith Ainsworth @AinsworthKeith]

The best explanation of the E Jean Carol case you’ll hear

[W. Benjamin Long @wbenjamin_1]

Legendary. Was at this game

[W. Benjamin Long @wbenjamin_1]

I still maintain: show me the data that makes it make sense. Don’t hide the data and counter opinions then guilt shame me into your rationality.

[W. Benjamin Long @wbenjamin_1]

@stoolgambling Bills

[hunter @hxxntrr]

Elon Musk hasn't sold a Tesla share in years and lives off $1 billion in personal loans

His Tesla stock keeps appreciating
The loans charge him 2-3% interest
The IRS never sees a single dollar of capital gains tax

This is exactly how the wealthiest people in America accumulate wealth without paying taxes and it's available to anyone with $100K+ in assets

The strategy is called "borrow against appreciated assets" or sometimes "buy borrow die." It's the single most powerful tax-minimization strategy used by ultra-wealthy individuals in America

Mechanics:

When you SELL an asset that has appreciated, you owe capital gains tax. Federal long-term capital gains rates: 0%, 15%, or 20% depending on income. Plus state capital gains in most states (CA: 13.3%; NY: 8.82%). Plus net investment income tax of 3.8% for higher earners (IRC Section 1411)

For someone like Elon Musk selling $1B in Tesla stock, the total tax bill would be approximately:

Federal capital gains at 20%: $200M
Net investment income tax at 3.8%: $38M
Texas state tax: $0 (Texas has no state income tax, this is why Elon moved there)

Total tax bill on selling $1B: $238M

When you BORROW against appreciated assets, you owe ZERO tax. Loan proceeds are not income under IRC Section 61. They never appear on your tax return. They never trigger a tax event

For Elon to access $1B in cash for spending purposes, the math is:

Sell $1B in Tesla stock: $762M in net proceeds after tax
OR
Borrow $1B against $1B in Tesla collateral at 2-3% interest: $1B in net proceeds tax-free

Selling costs him $238M in taxes
Borrowing costs him $20-30M/year in interest (or roughly $200-300M over a decade if held that long)

But the borrowing strategy has additional benefits:

Tesla stock continues to appreciate. Over 10 years, $1B in Tesla stock has historically appreciated to multiples of that. Selling locks in the gain at today's value. Borrowing keeps the upside

The interest paid on the loan is potentially tax-deductible if structured as an investment loan (IRC Section 163(d)). Effective after-tax cost can be reduced to 1-2%

The loan never has to be repaid during his lifetime. He can refinance it indefinitely. When he dies, his heirs inherit the stock at a "stepped-up basis" (IRC Section 1014). The accumulated capital gains die with him. The heirs sell the stock at the stepped-up basis, pay off the loan, and keep the entire upside tax-free

The wealth transfers from Elon to his heirs entirely tax-free if structured correctly. Estate tax is a separate question but is largely avoidable through proper trust structures

The ultra-wealthy version of this strategy:

Borrow against appreciated stock
Use the loan proceeds for consumption (homes, cars, art, business operations)
Never sell the underlying stock
Refinance the loan at maturity to extract more cash if the underlying has appreciated
Pass everything to heirs at death with stepped-up basis
Heirs sell with $0 in accumulated capital gains tax owed

This strategy is sometimes called "buy, borrow, die" by tax planners. It's the foundation of how billionaire wealth perpetuates across generations without significant taxation

Available products for this strategy:

Pledged Asset Line (Schwab): borrow up to 50-70% of portfolio value at SOFR + 1-2%
Securities Backed Line of Credit (Morgan Stanley, Goldman): similar terms, $1M+ minimum
Custom Lending Solutions (private banking): for $10M+ portfolios, rates can drop to 1-2%

The accessibility tier:

If you have $100K+ in investment assets at Schwab/Fidelity/Vanguard, you can open a Pledged Asset Line. Typical terms: borrow up to 50% of your portfolio value at SOFR + 1.5-3% (current rates roughly 6-8% all-in). No fixed monthly principal payments. Interest only or pay nothing as long as the loan stays below the maintenance threshold

For someone with $200K in stocks/ETFs:
Borrow $100K at 6.5%
Use the $100K for any purpose (real estate down payment, business operations, etc.)
Annual interest cost: $6,500
Tax savings vs selling stocks: roughly $20,000-$30,000 in deferred capital gains
Net benefit: $13,500-$23,500/year in tax savings during the borrowing period

For someone with $1M in stocks/ETFs:
Borrow $500K at 6.5%
Use the $500K for real estate purchases, business equity, etc
Annual interest cost: $32,500
Tax savings vs selling stocks: roughly $100,000-$150,000 in deferred capital gains
Net benefit: $67,500-$117,500/year

Comparison to the alternative:

If you sell $500K in long-term appreciated stock to access cash:
Federal capital gains at 15%: $75,000 owed
State capital gains (varies): $20,000-$40,000 owed
Net cash to you: $385,000-$405,000

If you borrow $500K against the same stock:
Net cash to you: $500,000
Tax owed: $0
Annual interest cost: $32,500

Even paying $32,500/year in interest, you're $90K-$110K ahead in year 1 and the gap grows because your stock keeps appreciating while you hold it

The compounding effect over 20 years:

Person A sells $100K of Tesla stock at 15% capital gains, takes $85K. Spends it
Person B borrows $100K against $100K of Tesla stock, takes $100K, spends it. Stock keeps growing at historical rate (let's say 20%/yr conservatively)

20 years later:
Person A: stock is gone. Whatever they bought with $85K is whatever it is
Person B: still owns the original $100K in Tesla, now worth $3.8M. Refinanced the loan multiple times. Currently owes maybe $200K against $3.8M in collateral. Net wealth on this position: $3.6M

Same starting position. Different decision. $3.5M+ difference in 20 years

Important caveats:

The strategy works only when underlying asset is appreciating
Margin call risk if asset value drops below maintenance threshold
Interest costs accumulate over time and eventually reduce the net benefit if rates rise enough
Some borrowing limits apply (typically max 50-70% of portfolio value)

The strategy is most powerful for:

Concentrated stock holdings in publicly traded companies (especially employee stock from tech companies, founder stock, ESOP grants)
Large diversified portfolios held in taxable brokerage accounts
Real estate equity (similar strategy via cash-out refinances)
Business equity (some forms of borrowing available against ownership stakes)

The strategy is least useful for:

Small portfolios under $50K (interest costs eat any benefit)
Retirement accounts (can't borrow against IRAs/401(k)s; some 401(k)s allow loans but limited to $50K)
Assets without an established lending market (collectibles, private real estate that's hard to finance)

The reason this isn't standard financial advice:

Most financial advisors are compensated based on assets under management. They make more money when you keep assets invested. They don't necessarily make money when you optimize for cash extraction. The strategy is genuinely good for sophisticated clients but doesn't fit the standard advisor compensation model

Banks DO know about this strategy. They actively market it to wealthy clients. The Pledged Asset Line and securities-backed line of credit products are billion-dollar businesses at every major brokerage. They're just not marketed to ordinary retail clients because the minimums and complexity make them inappropriate for mass market

The threshold for accessing this strategy:

$100K+ in liquid investment assets = entry-level access via Schwab/Fidelity
$1M+ = full access to most products and competitive rates
$10M+ = access to private banking rates of 1-2%
$100M+ = Elon-level rates of essentially 0% real cost after tax deduction and stock appreciation

At each tier, the math becomes more favorable. The richest Americans access this strategy at rates that mean borrowing $1B is essentially free relative to their portfolio appreciation

Most middle-class Americans never use this strategy because:

They don't know it exists
They don't have $100K+ in taxable investment accounts
They follow standard advice that says "live within your means and don't borrow"

The wealthiest Americans use it constantly because:

They have the assets
They understand the math
They follow advice from advisors who are sophisticated about tax optimization

The gap between the two groups isn't talent. It's understanding that the tax code is written to reward holding assets indefinitely and penalize selling them. Selling = taxable event. Holding + borrowing = no taxable event. The system rewards never realizing gains

Elon never sells Tesla. He never pays capital gains tax. The IRS doesn't collect a dollar from his accumulated wealth. The strategy is legal. It's mathematically optimal. And it's been written into the tax code since before any of us were born

You don't need to be Elon to use this strategy. You need $100K and a Schwab account

(we get business owners up to 250k in 0% interest business funding, link in bio)

[W. Benjamin Long @wbenjamin_1]

@AnnCoulter Spirit filed for bankruptcy protection in both Nov 2024 and Aug of 2025. I find your analysis incredibly short sighted. Who’s not worse off is the thousands of lives that stand to perish by nuclear armed Iran.

[W. Benjamin Long @wbenjamin_1]

Travesty to lose this wisdom.

[W. Benjamin Long @wbenjamin_1]

This is astonishing.