Samuel Harnisch, CFA, CFP®️

❌ Banned from TikTok #FreeSamuel
📈 Invest smarter
💰 Reduce taxes
🏠 Build & protect your family’s legacy

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

The first stock I ever bought gave me a 4x return.

The greatest restaurant on the planet was founded in Denver, Colorado.

When I was being recruited, one of the selling points for DU was that the original Chipotle was right across the street from campus.

To those who say money can’t buy happiness… they’ve never had a burrito after a long workout or practice.

Then the E. coli outbreak hit.
The stock dropped nearly 50%.

So when I started investing, guess what I bought?

Chipotle.

Before I knew it, I was up 300%.

I sold it because, at the time, that seemed like an unbelievable return (and it kind of was).

The entire investment thesis was based on one thing:

I liked their burritos.

And honestly, that’s how a lot of people invest:

• No real plan
• No process
• Just feelings and stories

Today, my approach is completely different.

When I discovered quantitative and systematic approaches to investing, it just clicked.

That’s where the name QFS comes from: Quantitative Financial Strategies.

The burritos are still great.

But I don’t build portfolios based on what tastes good anymore.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

Should you tax-loss harvest a stock you love?

This is a genuinely hard question for stock‑pickers.

Let’s say you’re incredibly bullish on a company.

The stock is down.

You could:

• Sell it
• Capture the loss
• Wait 30+ days to avoid the wash-sale rule
• Then buy it back

But what if it rallies during that 30‑day window and you miss the rebound?

This is the problem with picking individual stocks.

You’re attached to the stock.

As a systematic investor, I don’t care about any individual stock.

We’re long (and short) hundreds of securities at any given time.

There is no emotion involved. Just math.

We:

• Buy stocks with characteristics we believe are attractive
• Short ones with unfavorable characteristics

Then we layer taxes on top of that process and ask:

“What portfolio maximizes expected after-tax wealth?”

Sometimes that means harvesting a loss.

Sometimes it doesn’t.

A stock may be down significantly and still be such an attractive opportunity that the model chooses not to sell it.

Other times there may be multiple securities with similar expected returns, allowing us to harvest a loss while maintaining nearly identical exposure.

If you’re still doing bottom‑up stock‑picking in a taxable account, the “harvest vs hold” question is almost impossible to solve cleanly.

If you treat stocks as inputs to a model instead of your identity, you can optimize for what actually matters:

The after‑tax return of the whole portfolio, not whether you nailed one ticker.

If you want your tax‑loss harvesting to be part of a coherent, systematic process instead of a bunch of one‑off, emotional decisions, that’s exactly what we build. The link to book a brief call is in my profile.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

I had a call with a guy who sold his business for ~$17M in CA two months ago.

No tax planning.

Now he’s staring at a massive tax bill and asking what we can do.

At this point in the year, we’re limited.

We can do some bunching of charitable donations, tax‑loss harvesting, and maybe real estate depreciation if he has REPS.

These can help a little bit, but there is still going to be a meaningful tax bill.

Real tax planning happens before you sell the business, not after.

If you start 12–24 months before an exit, you can look at:

• Entity structure and deal structure
• Timing of the sale (December vs January matters)
• Pairing gains with long/short loss harvesting
• Charitable structures
• Installment sales
• Real estate / REPS / depreciation

Once the sale is done and the clock is ticking on the tax year, a lot of the biggest levers are gone.

But we can still build a tax‑aware portfolio for the proceeds going forward.

The damage from this exit is largely done.

The next one (or the next decade of investing) doesn’t have to be that way.

If you’re thinking about selling a business in the next 1–3 years and don’t have a real tax plan yet, that’s your cue.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

This is why I invested in SpaceX out of my Roth IRA.

Whenever I have the opportunity to invest in private equity, I’m very careful about where I hold it.

Let’s say (purely for illustration):
• You invest $100,000
• It grows to $500,000

Most people stop there and call it a 5x.
But that might not be true!

Because where you hold an investment can be almost as important as the investment itself.

Here’s the math on that $100K → $500K move:

Roth IRA

• Invest: $100,000
• Exit value: $500,000
• Tax owed: $0

You keep the full $500,000.
True result: 5x

Taxable Account (High-Tax State)

• Invest: $100,000
• Exit value: $500,000
• Gain: $400,000
• Tax bill: ~$148,000

You keep roughly $352,000.
Actual result: ~3.5x

Same investment. But wildly different after-tax outcomes.

This is why asset location is one of the most underappreciated decisions in wealth management.

This example reflects how I personally structured my own exposure. It’s not a recommendation to buy SpaceX (especially at the new valuation 😵).

But the principle holds:

Put your highest-upside opportunities in the most tax-sheltered accounts you have.

If you have a $5m+ portfolio and want to invest in things like Anthropic, Anduril, Stripe, OpenAI, etc. out of your Roth IRA, the link to book a call is in my profile.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

This is why I love investing in individual stocks

The ability to tax‑loss harvest losers gets all the attention…

But what about the winners?

By definition, you’ll own some of the best-performing stocks in the index you’re tracking.

So when it’s time to make charitable donations, we don’t donate cash.

We sort through the portfolio and identify the positions with the largest % unrealized gains.

Then we donate those shares instead.

You get to deduct the full fair market value of the position and get rid of that unrealized gain in your account.
(As long as you don’t exceed 30% of AGI & have held the position for > 1yr)

Running this through a Donor‑Advised Fund (DAF) makes it even cleaner:

• We transfer the shares directly into the DAF
• The client gets one tax receipt from the DAF sponsor
• Then they can recommend grants to any charities they want over time
• Charities receive simple checks, with no headache of processing stock donations

So the simple loop is:

Direct indexing → Own more individual names, harvest losses when they go against you

Charitable gifting from winners → Use the biggest gainers to fund your giving in a tax‑efficient way via a DAF

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

Most investors are unknowingly paying taxes they don’t have to.

If you hold bonds in a taxable account, every monthly distribution gets taxed as ordinary income – up to 37% federally. A third of it evaporates every year before you even see it.

A new class of ETF is changing that.

Rotational fixed income ETFs hold the same bond exposure you’d expect – but instead of paying out income every month, they rotate out of positions just before the ex‑dividend date, then rotate back in after.

The income never leaves the fund as a distribution. Instead, it accumulates as NAV appreciation.

When you eventually sell, that can be taxed as a long‑term capital gain (up to 20%) instead of ordinary income (up to 37%). That structural difference alone can be worth around 1% of annual tax alpha in many cases, in exchange for a small amount of tracking error.

For someone living off their portfolio, this matters enormously. You’re now choosing when to take the tax hit, instead of having it forced on you every month.

And it gets better.

When you combine this with an equity sleeve that’s actively harvesting tax losses, those losses can offset the capital gains from your bond “income.”

In other words, your effective tax rate on fixed income yield could be close to 0%.

The full stack might look like this:

1. Direct‑index S&P 500 → Track the index while tax‑loss harvesting individual stocks

2. Equity ETFs → Small‑cap US and international exposure through ETFs, with “backup” ETFs to harvest into

3. Rotational fixed income → Convert bond yield from ordinary income to capital gain treatment

4. Box spread loans → Access liquidity through cheap, tax‑deductible borrowing

This is what tax‑intelligent portfolio construction looks like in 2026.

Every layer of the portfolio is working to minimize the drag between your pre‑tax return and what you actually compound.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

San Francisco rents are up 22%.

Over the last few years, the consensus trade was:

• Leave San Francisco
• Work remotely
• Move to Austin, Miami, Nashville, etc.

But the companies creating the most value in AI are disproportionately concentrated in the Bay Area.

OpenAI.
Anthropic.
And hundreds of startups you’ve never heard of.

Those companies are creating wealth, hiring aggressively, and competing for a limited housing stock.

One of the most interesting opportunities today isn’t necessarily ground-up development.

It’s acquiring older housing stock, renovating it to modern standards, and delivering it back to market.

Local operators who understand neighborhood-by-neighborhood dynamics are uniquely positioned to capitalize on this trend.

That’s one of the reasons we’ve invested alongside Alex Wall at Echo Valley Real Estate

He is THE GUY when it comes to sub institutional real estate in San Francisco.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

We’ll be selling our shares in these companies after IPO - for tax-free gains.

We’ve been invested in SpaceX, OpenAI, and Anthropic for some time, and the growth has been exceptional.

When high-growth, pure-play companies go public, they often trade at silly prices as investors bid them up.

People buy stories.
They chase what’s hot.
Ignore valuation.

SpaceX is an incredible company.

That doesn’t automatically make it a great stock.

Your long-term return depends on two things:

• The earnings the business produces
• The price you pay for those earnings

I’m more than happy to sell our shares into those valuations and recycle the proceeds into opportunities that are more reasonably priced.

Normally, that kind of turnover would create significant tax drag.

But we generally hold these investments inside retirement accounts - preferably Roth IRAs.

That means when we sell after an IPO and redeploy the capital, the gains are tax-free inside a Roth and tax-deferred inside a traditional IRA.

If retirement account space is limited, you can still pair private equity with tax-aware long/short SMAs in taxable accounts to help offset gains and improve the overall tax picture.

So yes, I view these IPOs as exit liquidity.

And I’m all for it.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

When people ask what I think our best investment is, I usually say AirTrunk.

(And “best” to me is a risk-adjusted expected return profile)

This gigantic platform sits right at the intersection of two of the strongest themes:

1. AI infrastructure buildout

This is arguably the highest risk‑adjusted ROI place to be, because it doesn’t matter who wins the application layer.

A skilled, experienced team that can develop and operate data centers is invaluable to AI companies around the globe.

But what’s so critical is you HAVE to have access to large landbanks with power already secured, which Air Trunk does.

2. Emerging markets and high‑growth economies

AirTrunk develops and leases data centers across:

• Australia
• Hong Kong
• India
• Japan
• Malaysia
• Singapore
…and is expanding into Saudi Arabia.

These economies have large populations, rapid growth, and are earlier in their compute buildout compared to the U.S.

McKinsey projects that AI‑specific data center capacity in APAC is expected to surge ~3.5x by 2030.

In India alone, AirTrunk plans to invest more than $30B by 2030.

In addition to those themes, they also have the backing of Blackstone, which brings much more than just capital:

• Blackstone owns and operates QTS, the largest data center platform in the world
• QTS has been one of the best investments in Blackstone’s history
• They’re now applying the same expertise and playbook to APAC and beyond through the AirTrunk platform

For a lot of $10M+ portfolios that already have heavy US tech exposure, this is the kind of global, real‑asset, AI‑linked exposure we want in the mix.

If you’re curious how something like AirTrunk might fit into a diversified, tax‑aware portfolio, the link to book a brief call is in my profile.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

https://t.co/SHw4B0iZB6

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

Most wealthy families are borrowing the wrong way.

If you have a $5M+ portfolio and you’re using:

• Margin loans
• Securities-backed lines of credit (SBLOCs)
• Or selling appreciated stock to raise cash

…there may be a more efficient option.

One of the best-kept secrets in the family office space is the box spread loan.

At a high level:

• Borrow at rates typically close to the risk-free rate
• Lock in a fixed borrowing cost and term
• Avoid selling appreciated assets
• Create deductible capital losses

A few use cases I cover in my latest video:

• Creating liquidity from concentrated stock positions
• Funding real estate investments with significant depreciation
• Pairing financing with tax-aware investment strategies

Many investors spend years optimizing their portfolio but never optimize how they borrow.

That can be an expensive mistake.

I also take a shot at Tony Yang in this video, who seems to have a thing for MacBooks…

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

One of my favorite nuggets from the conference last week was how you can potentially push the QSBS exemption far beyond $15 million through effective basis planning.

This post assumes a basic understanding of QSBS and the latest exclusion limits, which are generally the greater of:

• $15 million of gain, or
• 10x your adjusted basis in the QSBS stock

Most founders end up relying on the $15 million exclusion because they started the company with very little basis. While trust planning can sometimes multiply the exclusion amount, it often comes with tradeoffs around control, flexibility, and complexity.

One strategy I heard discussed was starting the business as an LLC taxed as a partnership or sole proprietorship and converting to a C corporation before a major liquidity event.

The idea is that if owners have accumulated meaningful tax basis prior to conversion, the resulting QSBS stock may have a significantly larger basis than a founder who started a C corporation with only a nominal capital contribution.

Under the latest rules, corporations generally must have aggregate gross assets of $75 million or less at the time the stock is issued to qualify for QSBS treatment. That means the potential exclusion under the 10x basis rule can become extraordinarily large in the right circumstances.

The caveat is that basis planning is highly technical. The relevant number is generally tax basis, not fair market value, and there are numerous rules, limitations, and anti-abuse doctrines that can apply.

The longer I do this, the more I realize that estate, tax, and business attorneys are often the biggest needle movers when it comes to preserving wealth.

The tax savings from successful QSBS planning can be enormous.

I’m out of my depth here, so if this applies to you, talk with a qualified QSBS attorney. At a high level, examples of legitimate planning may include:

• Contributing cash to a new C corporation.
• Contributing assets with substantial tax basis under Section 351.
• Converting an LLC taxed as a partnership into a C corporation after accumulating meaningful basis.
• Structuring a conversion before a major liquidity event while satisfying the QSBS requirements.

Where practitioners get concerned is what is often referred to as “basis stuffing” - transactions designed primarily to inflate basis without a corresponding economic investment or business purpose. Examples may include:

• Circular cash movements.
• Temporary asset contributions.
ª Contributing assets unrelated to the business solely to increase basis.
• Last-minute transactions immediately preceding a sale.
• Transactions vulnerable to economic substance, step transaction, or other anti-abuse doctrines.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

Stocks always go up

Except for when there is war, revolution, extreme bubbles, or hyperinflation.

Germany in the 1920s - the stock market initially soared, but hyperinflation wiped out any real value.

Russia during the 1917 revolution - private property was nationalized and shareholders were essentially wiped out.

China during the 1949 revolution - private companies were nationalized and existing shareholders lost their claims.

Japan in 1989 - fell roughly 80% from the peak of the bubble, taking more than 30 years to regain its prior nominal peak (If you include dividends it isn’t nearly as bad).

Greece 2007–2016 - the Greek stock market fell over 90% during the sovereign debt crisis and many individual banks/companies were effectively wiped out.

China in 2007 - the Shanghai Composite Index dropped around 70% and is still below the 2007 high nearly two decades later.

United States 1929–1932 - Market fell roughly 85%-90%, thousands of banks failed, and unemployment exceeded 20%.

Stay diversified out there people. Especially if you’re in or nearing retirement.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

Here’s how you borrow money from the government for free.

If you can avoid, reduce, or defer taxes, it’s essentially an interest‑free loan from the government that you get to invest.

I call it synthetic (or phantom) equity.

Take the manufactured home community deals as an example.

For high earners we work with who have REPS, the year‑1 “return” from tax savings alone can, in some cases, exceed 60%.

Obviously, you should never make investments only for tax reasons.

But when sound assets come with real tax benefits, it completely changes the math.

On $1M invested, you might effectively create ~$600K of “new” equity via tax savings that you wouldn’t have had otherwise.

Whether it’s:

• Tax‑aware long/short
• Tax‑aware hedge funds
• Tax‑advantaged real estate

…we can tilt the odds in your favor by building more and more synthetic equity that would otherwise have been lost to taxes.

I always tell people: you’re doing the heavy lifting by having 7‑figure income – we’re just helping you keep more of it.

If you want to see how much synthetic equity you could realistically build over the next few years, the link to book a brief call is in my profile.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

†The interest rate and tax deduction savings interactive tool is for illustrative purposes only. Calculations assume interest rate savings equal to 2% of the loan amount and potential tax savings equal to 1% of the loan amount. Actual savings may vary based on market conditions, loan structure, tax circumstances, and individual client eligibility. Savings estimates are based on generalized assumptions and do not constitute tax, legal, or investment advice. Users should consult with their own financial or tax advisors to assess the applicability of any savings in their personal circumstances. This tool does not recommend or favor any specific investment and does not evaluate or compare a universe of alternative lending or investment options. Other financial solutions not analyzed here may offer similar or greater benefits.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

Had a great call yesterday with someone with a $15M portfolio.

His 3 main pain points:

1. Concentrated stock from a previous employer
2. Large W‑2 income from RSUs with his current employer
3. Looking at buying a house in CA and it’s insanely expensive

Solution #1

We walked through using a tax‑aware long/short strategy to wind down the concentrated position in a largely tax‑neutral way.

There’s nuance here: do you just let it ride while you harvest losses, or hedge with a collar so you don’t get crushed if it sells off?

Given his risk tolerance, we landed on collaring the position while we harvest losses over 1–2 years. That way the value of the stock is protected.

Solution #2

His portfolio has no exposure to diversifying hedge fund strategies.

By taking a tax‑aware approach to that sleeve, we can expect to realize ordinary deductions along the way. For high earners in CA, a $500K deduction could be worth ~$250K of tax savings annually.

That directly attacks the W‑2 / RSU problem.

Solution #3

Instead of just swallowing a big, expensive mortgage, we’re looking at a hybrid structure:

Take a traditional mortgage in the $750K–$1M range

• Federal mortgage interest deduction cap is $750K
• California cap is $1M

Borrow the rest against his portfolio via a box spread loan at ~4%

Result:

• Lower blended financing rate
• Maintain tax benefits across the entire debt stack

Along the way, we’ll be:

• Diversifying his retirement accounts into private equity, credit, and infrastructure

Planning for him to stop working in ~5 years, at which point:

• Tax‑aware real estate can create tax‑favored income to replace salary
• Ordinary deductions from hedge funds + RE can fuel Roth conversions, shrinking the future RMD problem

If you’re in a similar spot - big portfolio, big RSUs, big tax bills, and big life decisions coming up, this is exactly what we specialize in.

The link to book a brief call is in my profile.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

What happens when you combine NUA, 351 exchanges, and box spreads?

Let’s start with the situation.

Suppose someone has:

• $3M in a 401(k)
• $1.5M of which is employer stock
• A cost basis of only $200k in the stock

Many people would simply roll the entire account into an IRA and miss one of the most valuable tax planning opportunities available.

Instead, NUA (Net Unrealized Appreciation) may allow them to distribute the employer stock from the retirement plan and pay ordinary income tax on only the $200k basis.

The remaining $1.3M of appreciation can potentially receive long-term capital gains treatment when sold.

That’s a huge improvement, but now the clients owns a highly concentrated stock position in their brokerage account.

(Obviously you can use a tax-aware long/short strategy here as well, but I wanted to show an alternative for this post)

That’s where a Section 351 exchange can potentially help.

Rather than selling the stock and triggering capital gains, the shares may be contributed (along with other stocks and ETFs) into a newly launched ETF structure, allowing the investor to diversify while continuing to defer taxes.

Now we’ve solved the tax problem and the concentration problem.

The next challenge is liquidity.

Because the investor now owns a diversified portfolio, the position may be much better suited as collateral for a box spread loan.

Instead of selling assets and paying taxes, they can potentially borrow against the portfolio at attractive rates while continuing to defer the embedded gain.

In one case we’re working on, we’re taking it a step further.

The box spread loan proceeds are being invested into a tax-aware hedge fund that can realize ordinary deductions.

Those deductions can help offset the ordinary income created by the NUA basis adjustment today, and in future years can potentially be used to offset Roth conversions as we work to reduce the client’s IRA balance before RMDs begin.

This is why I find taxable investing so fascinating.

Most people look at:

• NUA
• Section 351 exchanges
• Box spreads
• Tax-aware hedge funds
• Roth conversions

as completely separate strategies.

The real magic happens when they’re coordinated together as part of a comprehensive financial plan.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

One of our AI investments I’m SUPER excited about right now.

There’s so much demand from businesses wanting to implement AI that Anthropic and our PE partner created a new business unit focused purely on deployment.

Within this business, applied AI engineers from Anthropic work directly with enterprise engineering teams to:

• Identify where Claude can have the most impact
• Build custom AI solutions
• Support and iterate with customers over the long term

The focus is mid‑sized companies across industries – each engagement shaped by the people closest to the work.

Some examples could be:

• Community banks
• Mid‑sized manufacturers
• Regional health systems

All of them stand to gain from AI, but most don’t have the in‑house resources to build and run frontier‑level deployments.

Rewiring the economy for AI is going to be one of the biggest value creators of the coming decades.

The problem is very few know how to translate AI into concrete workflows and models that maximize ROI.

This unit exists to close that multi‑trillion‑dollar gap between where businesses operate today and where they could be.

If you’re interested in exploring whether opportunities like this belong in your portfolio – and how to do it in a tax‑aware way – the link to book a brief call is in my profile.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

This is why financial planning and investment management should not be separated.

I’ve heard people say:

“Just pair tax‑inefficient investments with strategies that realize deductions and it all nets out.”

In theory, that sounds fine.

But in practice, it often misses the bigger picture.

Having an ordinary deduction in a portfolio does not automatically mean it’s optimal to stuff a taxable account full of ordinary‑income investments.

My typical order of operations:

• Use ordinary deductions against earned income
• When retired, use them against Roth conversions
• Only after IRAs are fully converted to Roth→ consider adding more taxable income in the brokerage account to pair with those deductions

Why?

Because every dollar of taxable income you unnecessarily create in the portfolio is one less dollar of earned income or Roth conversion you can offset.

And if someone really needs / wants income, there are plenty of tax‑efficient ways to do it:

• Real estate with depreciation
• Securitized affordable‑housing loans
• No‑distribution ETFs with capital gains treatment
• Traditional muni bonds, etc.

There’s rarely a good reason to introduce investments that increase your AGI just because you “have deductions.”

You simply cannot build an optimal investment portfolio without understanding the rest of the equation:

• Projected income over the next 3–5 years
• Stock‑based compensation
• Current IRA/401(k) balances
• Desired retirement date
• Cash‑flow and liquidity needs
• Estate and legacy goals

That’s why comprehensive planning and portfolio design have to be done together. Anything less is guesswork.

[Samuel Harnisch, CFA, CFP®️ @SamuelHarnisch]

Greatest conference of all time 😄

Two days completely dedicated to taxable investing. I was in heaven.

Key takeaways:

• Jeff Chang has a thing against CPAs and Minivans

• If you ask Meb Faber's AI anything make sure you tell it to be brief

• Vise I’m still confused

• Joe Giroux’s advice to those looking to access tax-aware long-short cheaply: DONT

• John Hill is really tall

• AQR Capital Management is still smarter than everyone

• Rob D. Arnott says the active component of passive investing is like Cathie Wood on crystal meth

• Tony Yang has a heart of gold

• Phil Huber what the heck are you even doing at a taxable investing conference?

• Andrew Berman and Nick Bruce are so put together I can’t think of anything to poke fun at

Can't thank @TaxAlphaInsider enough for all the work that went into putting it together. You my friend, are the tax-aware investing GOAT.