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The Propeller – Step Up Basis is better than 10,000 steps a day! – 6-8-2025

Investing / Financial Independence: Step Up Basis

Bob made a very expensive tax mistake.

Doctors told Bob that he only has a year to live…

What did Bob do?

He decided to gift a house to his only son before passing away.

The house is worth $2,000,000 that he acquired back in 1970 for $50,000 in an expensive suburb of California.

The son decided to sell the house and paid ~$430,000 of federal taxes.

$430,000 that could have been $0 instead…

How?

When you gift a property to someone, they receive a “carryover basis.” It basically means the same price the original owner purchased it for.

So, the basis of that house was $50,000, and the son had to pay capital gains tax of 23.8% on the difference between the sale price ($2M) and the basis.

BUT, this is where a step-up basis could’ve come into play.

Assets (house, stock/ETF shares held in a brokerage account, etc.) that you own inside an estate (essentially not in an irrevocable trust) receive a step-up basis to their fair market value (FMV) at the time of the decedent’s death per the IRC Section 1014. 

In this case, if Bob held that house in his own name, passed away, and his son received the house, he would’ve gotten a step-up in basis to the current value, or $2M.

At the time of the sale, if sold for $2M, he would pay $0 in federal taxes (state tax might apply).

That’s ~$430,000 of savings.

“But who cares, Bob is dead anyways?”

While that’s true, many parents still want to ensure that their children don’t have to pay half a million in taxes.

 

Specifics

The step-up in basis can be a bit nuanced, depending on how the assets are held and titled.

First, the step-up in basis typically adjusts to the market value, unless an election is made to use a value 6 months after the date of death (some rules apply).

The step-up in basis also doesn’t apply to assets held in an irrevocable trust (but we will discuss some strategies there) or to assets held in qualified retirement accounts (IRA, 401(k), etc)

In a community property state, the basis steps up whenever a spouse dies. You will typically need to complete a form to receive this step-up in a brokerage account. For example, Fidelity has a “Cost Basis Update – Date of Death Step-Up” form.

For assets held in joint tenancy, the step-up applies only to the deceased partner’s share. For example, Bob and Jenice have a house worth $300,000 with a $50,000 basis. After Bob passes away, Jenice will have a $175,000 basis in the house (($300,000 – $50,000) / 2 + $50,000).

 

Additional tax planning opportunities:

1. Living on the right assets

Bob, age 75, has 2 accounts: a traditional 401(k) worth $500,000 and a brokerage account worth $500,000. Bob’s diagnosis isn’t good.

From a tax planning perspective, it might make a lot more sense to withdraw, say, $50,000 per year to live off (of which $20,000 is RMDs) from the 401(k) and pass down the brokerage account to his beneficiaries.

This is because the brokerage account likely has a lot of gains (Bob bought many stocks in his 30s–40s) that could be stepped up. But a more in-depth analysis might be needed if Bob has a lot of income and is in a high marginal tax bracket.

 

2. Selling the right lots

Say Bob has a $500,000 brokerage account. Some of the stock purchases have a low basis (meaning a lot of capital gains), and some of the stock purchases have a high basis (low capital gains).

It’s best to sell stocks with a high basis (low capital gains tax) and pass down the low basis stocks to the beneficiaries.

 

3. Taking loans

Depending on the portfolio size, it could make sense to take out a loan instead of paying capital gains.

 

4. Irrevocable trust planning

Assets inside an irrevocable trust don’t get a step-up in basis, as they are considered outside of an estate. But there is a potential planning opportunity by using the swap power.

Typically, irrevocable trusts hold assets with a low basis. These trusts often include the “swap power,” or the ability to exchange assets in an irrevocable trust with other assets of equivalent value.

Say a wealthy individual has $1M of cash and $1M of stocks held in an irrevocable trust (with $50,000 of basis). He could swap that cash, get the stocks out of the irrevocable trust, and the beneficiary could receive a step-up in basis.

Of course, not everyone would have sufficient assets to exchange, but it could be a good way to save money on taxes in the right circumstances.

 

5. Donations

There are some families that are charitably inclined. Say Bob has $1M in an IRA and $1M in a taxable brokerage account. His kids are doing great financially.

Bob wants to give away $1M to a charity. In his situation, giving away $1M from the IRA is better tax-wise than giving $1M from the brokerage account, since the step-up basis will apply to the beneficiaries, resulting in less taxes when they sell.

 

Planning matters. These mistakes can cost thousands of dollars in unnecessary taxes.

 

Father's Day gifts for every budget

Tech: Protect Your Privacy: Why You Should Consider Incogni.com

In today’s hyper-connected world, your personal data is everywhere – scattered across dozens (if not hundreds) of databases, most of which you’ve never heard of. As a tech and finance writer, I believe protecting your personal information is just as important as protecting your money. That’s where Incogni.com comes in – the most powerful, automated service designed to help you remove your private information from the web.

Think of it as a digital cleanup crew working tirelessly to pull your data off people search sites and shady data brokers who profit from selling your identity, habits, and even location history.

Top 5 Reasons to Use Incogni.com

1. Data Privacy Is a Financial Risk

Your personal data isn’t just a privacy issue – it’s a financial liability. Data brokers sell your information to advertisers, spammers, and potentially cybercriminals. The more data out there, the easier it is for scammers to impersonate you or commit identity theft.

2. It’s Automated and Hands-Free

Incogni does the heavy lifting for you. Instead of sending manual requests to dozens of data brokers (which is time-consuming and confusing), Incogni automates the process using privacy laws like GDPR and CCPA to force companies to delete your data.

3. You Stay Off the Radar

Regular removals keep your data off the market. Even if your information resurfaces, Incogni continues to monitor and resubmit requests. This ongoing service means you’re not just wiping your digital footprints once – you’re keeping them off for good.

4. Increased Peace of Mind

Knowing that your name, home address, family members, and purchase habits aren’t floating around the internet is powerful. Especially in an era of constant data breaches and phishing scams, digital peace of mind is priceless.

5. Helps Build a Minimalist Digital Identity

As a fan of financial minimalism and tech efficiency, I love the concept of digital minimalism – keeping your digital presence lean and intentional. Incogni helps you reduce your digital surface area, making you less vulnerable and more in control.

In a world where everything is trackable and sellable, you need to take control of your digital identity. Whether you’re an entrepreneur, investor, or everyday internet user, keeping your information private is no longer optional – it’s essential.

Incogni.com is a smart tool that takes the hassle out of staying private. For a small investment, you get big protection. It’s like antivirus for your identity—and just as necessary.

I’ve been working with Incogi to bring special offers to the readers of The Propeller.  Simply us this link to get access to special offers – Incogni Special Offer for Readers of The Propeller

Stay safe. Stay smart. Stay incognito. 

Entrepreneurship: Creativity Loves Constraints

Back in the 1950’s – Dr. Seuss was on fire. 

He wrote Cat in the Hat and How the Grinch Stole Christmas. 

He started to get a reputation for his style of short, silly words. Cat in the Hat only used ~236 total words. 

His publisher, Bennett Cerf, decided to up the ante – he challenged Dr. Seuss to a bet:

Write a children’s book using only 50 unique words. 

Challenge accepted.

 

Not only did Dr. Seuss win the bet, but the book (Green Eggs & Ham) became his best-selling book of all time. (8M+ copies sold)

Sometimes The Constraints Pick YOU

When Steven Spielberg was filming “Jaws” – he ran into a massive constraint.

  • Attempt #1 – use real sharks (production team said NO)

  • Attempt #2 – build a mechanical shark ($250,000 … and it broke 3 times because of the water)

So they were done. How do you film a shark movie without the killer shark?

They were about to pause production, when Spielberg had an idea: Embrace the constraint.

How can I make a terrifying shark without ever showing it on camera?

Answer: 

  • Triple down on the music and lighting

  • Shoot the movie from the shark’s POV – so you never see the shark 

  • Only show the shark fin (a swimmer’s nightmare)

The result? A Smash hit with about $500M in initial box office sales on a $7M budget.

As Spielberg later admitted: “If the mechanical sharks had worked, Jaws probably would’ve been a worse movie.”

The Takeaway

If you listen to people like David Goggins, you learn a counter-intuitive insight: self discipline is what unlocks personal freedom. 

Similarly – constraints are what unleash creativity. 

“Creativity starts when you cut a zero from your budget.” — Jaime Lerner

“The enemy of art is the absence of limitation.” — Orson Wells

Even I use this principle. I find ways every week to take large topics and present them to all of you as a bite size post.

“Think outside the box” is a phrase I use often, but maybe it is wrong. What great entrepreneurs do is put themselves into a tight box to do their best work. 

 
 
Quote of the Week

“Do something every day that scares you a little.”

— Eleanor Roosevelt

Creativity thrives when we step out of our comfort zones. By regularly challenging ourselves, we open our minds to new perspectives and possibilities.

But let’s be real — nobody’s expecting you to go skydiving every day. Start small…
Order a dish you can’t pronounce at a restaurant
Strike up a conversation with a stranger
Take a different route home
These mini-adventures rewire your brain, making it more adaptable and receptive to new ideas. And who knows? That stranger you talked to might just inspire your next big project.
Remember, creativity isn’t some mystical force that strikes a chosen few. It’s a muscle that grows stronger with use. So flex it daily, in ways big and small. Your next breakthrough might be just around the corner.
 

Don’t forget Fathers Day is coming next week!

 

This is re-published from the weekly email sent by Leonard Mack entitled The Propeller.  To subscribe, visit https://www.LeonardMack.com/subscribe and read it every Sunday evening.

 

This intellectual nourishment is intended for informational purposes only. One should not construe anything herein as being legal, tax, investment, financial, or other advice.

 

My rule is this – I have no advice to give, only experience to share. I have no interest in being a guru or telling people what they should do. Rather, I share my own experience because there is no right or wrong. Your mileage may vary.