Net Unrealized Appreciation | Episode 5

March 6, 2025

Most entrepreneurs believe once they achieve financial success or have the big exit, freedom, fulfillment, and happiness will follow.

It’s a trap.

And today’s guest learned that the hard way.

On today’s pod, I’m talking with Pablo Della, an 8-figure founder who went from growing up poor in Argentina to scaling his business into a major consumer brand.

From the outside, it looked like he had won.

But after the financial success came a deeper question: Now what?

In this conversation, Pablo shares what changed after the money stopped being the goal, and how he rebuilt his life around real freedom.

He’s also just launched a new show, Freedom Flip, where he and his co-host publicly challenge conventional thinking around money, identity, and achievement. Go give it a follow RIGHT HERE!

In this episode, you’ll learn:

Why Pablo believes that spending money on experiences generate a real return on happiness, time, and quality of life that goes beyond ROI.

How Pablo evaluates the true cost-benefit of flying private—and why the math looks different once you factor in time, energy, and opportunity cost.

Why Pablo believes inflation isn’t accidental, and how that belief shapes his long-term view on money, Bitcoin and wealth.

Transcript

0:08
This week’s episode will focus on a strategy of selecting specific lots for your NUA. This approach may be more challenging if you do not have access to all the lot details of company stock that are in your retirement plan.

0:17
Under this approach, you select older prior lots that may have a lower cost basis than more current lots.

0:24
Let’s say you have 5,000 shares of Company Stock A in your retirement plan, valued at $600,000, with a $300,000 cost basis.

0:31
The company has experienced a prolonged period of stock price declines, so recent shares have a higher cost basis.

0:39
At first glance, it probably does not make sense to elect an NUA on the full number of shares, as you would owe ordinary income taxes on the $300,000 of cost basis.

0:55
However, let’s look at a simple example and assume that there are three lots that make up the $300,000 cost basis:

Lot 1: 3,000 shares, cost basis of $50,000

Lot 2: 1,000 shares, cost basis of $100,000

Lot 3: 1,000 shares, cost basis of $150,000

1:19
In this example, if you could select only Lot 1 for your NUA and then roll over the remaining shares to an IRA, you would only pay ordinary income taxes on the $50,000 cost basis of Lot 1.

1:26
This equates to $16.67 per share for the cost basis, with a market value of $120 per share.

1:35
In this example, the NUA would be $310,000, which is the difference between the market value of $360,000 and the $50,000 cost basis.

1:43
That is not a bad trade-off for a little digging into what comprises your total cost basis.

1:51
Until our next episode, keep searching for opportunities to enhance your wealth.

Keep Learning

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