U

Private Reading

The Untaxables

For internal use only

STRUCTURE
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The Untaxables — Private Reading

Four stories about structured wealth.

Self-Made Wealth. Structured Forever.

01Elliot 02The Manager 03Fund A & B 04The Race
01

Elliot is 45. He runs a fund. He has been running it for eleven years and it has performed. He is not reckless. He is not naive. He understands risk better than most people in any room he enters.

But next quarter he is deploying $6.7 million into a single position. The thesis is sound. The diligence is complete. The conviction is real.

He has done this before. And he knows that no matter how good the thesis is, a $6.7 million bet carries tail risk. If the position goes wrong — if the thesis is right but the timing is wrong, if there is a macro dislocation, if the world moves sideways in a way that has nothing to do with his analysis — his income in retirement is affected.

This is the part most managers don't talk about. The bet might be right. The structure might still cost them.

What the structure does

Alongside the deployment, Elliot commits $115,000 a year for five years. $575,000 total. The bank funds the balance of the full $4.25 million premium. His existing assets serve as collateral — they don't move, they don't get liquidated. The bank is covered from day one.

The structure has no relationship to the performance of the position. It participates in market upside with a floor of zero on the downside. It never goes backward. When the position has a bad year — the structure doesn't.

If the position wins — Elliot wins twice. If the position loses — the structure still pays $176,743 a year from age 59. Untaxable. Every year. For the rest of his life.

What leverage changed

Before bank-backed leverage existed, the logic worked anyway. A manager who understood the structure would have committed the full $4,250,000 out of pocket. Same income. Same outcome. Still the right move. Today it costs $575,000.

Without leverage
~3.3×
$4,250,000 out of pocket
Still the right move
With bank-backed leverage
~24×
$575,000 total — $115K/yr × 5
Same outcome. 86% less capital.
Annual carry$115,000/yr × 5 yrs
Total commitment$575,000
Total structure cost (bank-funded)$4,250,000
Untaxable income from age 59$176,743/yr
Total outcome at 88$14,048,759
For every $0.04 committed$1 returned
The position might be right. The structure is certain.
$575,000 in. $176,743/yr untaxable from 59. $14M at 88.

The position may win or lose. The structure has already decided.
02

There is a category of capital that almost every manager ignores.

Not the growth capital — that's working. Not the deal flow, the fund, the positions. That money has a job.

The ignored capital is the preserved capital. The money sitting in treasuries, fixed income, taxable money market accounts. The money that feels safe. The money that is waiting.

It is waiting to unwind ugly.

What preserved capital actually costs you

Every dollar of yield from a taxable account is ordinary income. Every distribution at retirement is taxed. Every dollar transferred at death is subject to estate tax at 40%.

You worked to accumulate it. Someone else decided how it leaves.

Now consider what happens when you take a sleeve of that preserved capital — just a sleeve — and put it somewhere that actually works.

$450,000. Twenty years. $13.3 million accessible.

A bank-backed structure. $90,000 a year for five years — $450,000 total. The bank funds the balance. Existing assets serve as collateral. At 65 — approximately $13.3 million is accessible. Not a liquidation. Not a taxable event. A war chest that built itself while everything else was working.

Annual carry$90,000/yr × 5 yrs
Total commitment$450,000
Cash value at 65$15,643,537
85% accessible at 65~$13,300,000
Total outcome at 88$28,947,727
For every $0.02 committed$1 returned
Without leverage
~4.6×
$6,300,000 out of pocket
Full premium — still the right move
With bank-backed leverage
~64×
$450,000 total — $90K/yr × 5
Same outcome. 93% less capital.
Shouldn't all preserved capital go somewhere that actually works?
$450,000 in. $13.3M accessible at 65. $28.9M at 88.

Not growth. Not preserved. Structured.
03

Fund A runs long/short equity. Disciplined. Consistent. Their LPs are satisfied.

So Fund A allocates $50 million into Fund B. Different strategy. Different sector. Different return drivers. This is the kind of allocation sophisticated managers make every day.

The $50 million leaves Fund A's control. It is now in Fund B's hands.

The allocation is sound. But what protects it?

The question most managers never ask

If Fund B has a catastrophic year — a strategy failure, a key-man event, a dislocation that hits their specific exposure — Fund A's $50 million is impaired. Most managers hedge the market. Almost nobody hedges the allocation itself.

The structure placed alongside the allocation

Fund A commits $4 million alongside the $50M. The bank funds the balance. The structure has no relationship to Fund B's strategy, sector, or the macro forces driving Fund B's returns.

If Fund B wins — the structure pays untaxable income and delivers a clean legacy transfer.

If Fund B loses — the structure still pays untaxable income and delivers a clean legacy transfer.

Fund B allocation$50M
Annual carry$800,000/yr × 5 yrs
Total commitment$4,000,000
Untaxable income from age 59$1,307,396/yr
Total outcome at 88$105,175,421
Correlation to Fund BZero
Without leverage
~3×
$31,500,000 out of pocket
To protect $50M — still worth every dollar
With bank-backed leverage
~26×
$4,000,000 total — $800K/yr × 5
Same outcome. 87% less capital.
The best hedge isn't against the market. It's against the assumption that the allocation will work.
The $50M into Fund B was a good decision.
The structure placed alongside it was a better one.
04

Everyone in the paddock knows the story.

A two-time NASCAR champion. Five indexed universal life policies purchased between 2018 and 2022. $10.4 million in premiums over seven years — one policy alone required $1.5 million a year for five years. No bank. No leverage. No independent intermediary between the agent and the carrier.

The pitch: pay a million dollars a year for five years, withdraw $800,000 a year from age 52, tax-free, for life.

What was actually designed: a $44.5 million death benefit on a single policy — inflated far beyond what was necessary — which generated the maximum possible agent commission and triggered catastrophic cost-of-insurance charges. The cash value was directed into a fixed account earning 1.5%, not the indexed account, so during strong market years the cash didn't participate in any of the upside. The cost of insuring a $44.5 million death benefit consumed what was left. When a sixth premium notice arrived on what was supposed to be a five-year plan, an independent firm evaluated the portfolio. The policies would lapse in sixteen months. $8.5 million gone.

Not on the track. In the design.

The driver's wife went public. The story traveled through every garage in every series.

But cautionary tales teach the wrong lesson.

The lesson wasn't "don't structure." It was "don't let an agent design it."

Every failure traces to one root cause: no independent intermediary between the agent and the carrier. When the agent controls the design, the design serves the agent. The death benefit was inflated to $44.5 million — the maximum commission target — when an equivalent structure would have required $32 million or less. That inflated death benefit triggered cost-of-insurance charges that consumed the cash value from one side. Cash was then directed into a 1.5% fixed account rather than the indexed account, ensuring it couldn't grow enough from the other side to recover. Either choice alone would have been damaging. Together, they were fatal.

The five-pay funding schedule wasn't the problem. Getting money into a policy quickly — maximizing early cash value, creating a short funding commitment, building a structure that can stand on its own — is sound design. What killed this policy was what the money was buying and where it was going once it arrived.

An intermediary operates differently. They sit between the agent and multiple carriers and banks simultaneously — and that competition is the mechanism. When the design has to survive comparison across every carrier in the market, inflating the death benefit to maximize a single carrier's commission toggle stops being an option. When the bank is evaluating the structure alongside the policy, the cash has to be in the indexed account — not the fixed account — or the leverage math doesn't work. The intermediary's compensation comes from the outcome, not from maximizing one carrier's product. The competition does what a single-carrier relationship never can.

The structure itself was sound. What failed was the architecture.

He died at 41. The policy was already gone.

Kyle Busch died in May 2026 at 41 years old. The original five Pacific Life policies — the ones the family paid $10.4 million into — had already lapsed or been surrendered before his death. The cash value was gone. The $44.5 million death benefit was gone with it. The family received coverage only from the replacement policies that an independent specialist had arranged during the litigation.

This is the part that turns a bad investment story into something else entirely. Life insurance has one job. It did not do that job — not because the concept failed, but because the design guaranteed the policy could not survive to the claim. The inflated death benefit created cost-of-insurance charges the cash value could never outrun. The fixed account ensured the cash couldn't grow to compensate. The policy was designed to produce a commission. It was not designed to still be standing when someone died.

A properly designed policy — minimum death benefit, indexed account, cash value actually building — does not lapse that way. The cash is the floor. As long as cash is accumulating, the policy stays in force. That is not a feature. That is the point.

What $10.4M properly designed should have produced.

Here is the part that matters most: the $800,000 a year promise wasn't an impossible number. A properly funded $10.4 million policy — minimum death benefit, indexed account, independent intermediary — produces somewhere between $430,000 and $800,000 a year in untaxable income depending on design. The structure works. The promise was in the right ballpark. What failed was how the money was deployed once it arrived.

The death benefit on a properly designed $10.4 million policy should have been sized at the minimum required under 7702 — roughly $31 to $35 million. That is the threshold that maximizes cash value efficiency: the lowest coverage that keeps the policy compliant, so that cost-of-insurance charges are minimized and the premium dollar does the most compounding work. The forensic analysis of the actual policy found that with any other carrier at the same $44.5 million death benefit, the target premium would have been $500,000 to $600,000 — not $1.5 million per policy. Pacific Life's compensation structure allowed the agent to push the target premium to $1.5 million. That difference flowed directly to the agent. It did not flow to Kyle.

$10.4 million in premiums, properly designed: approximately $430,000 to $480,000 a year in untaxable income. Death benefit of $31 to $35 million — properly sized, not inflated. Cash compounding in the indexed account, not the fixed account. An outcome at 88 of approximately $34 million. A policy that builds, not collapses.

With bank-backed leverage, that same $10.4 million in total structure cost requires $277,333 a year for five years — $1.39 million out of pocket. The bank funds the remaining $9 million. The outcome is the same. The client commits 13 cents of every dollar the wrong structure cost.

Total premiums paid$10,400,000
Death benefit on paper$44,500,000
Death benefit at death — policies had lapsed$0 from those policies
Net loss alleged$8,500,000
Properly designed — DB at death age 41~$35M — actually paid to family
With leverage — net to family at age 41~$22M on only $1.39M committed
Properly designed — DB if lived to age 88~$200M (cash value compounds to $190M)
Annual income from age 59 if he'd lived$700,000 – $1,000,000/yr untaxable
Could a properly designed policy lapse?No — cash value is the floor
Wrong design$10.4M in → $0 to family (lapsed)
Right design · no leverage$10.4M in → $35M to family
Right design · leveraged$1.39M in → $22M to family
What actually happened
−$8.5M
$10.4M in · fixed account · inflated DB · lapsing
No intermediary. No leverage. No floor on cost of insurance.
What the right structure delivers
~25×
$1.39M total · $432,500/yr untaxable · $34M at 88
Indexed account. Independent design. 87% less capital.
The speed is on the track. The structure behind the team is what determines whether the business outlasts the driver.
$10.4 million in. $8.5 million gone. $44.5 million on paper. Zero at death — the policies had already lapsed.

A properly designed policy at that same premium: approximately $35 million to the family at age 41. Actually paid. Income tax free. Outside the estate. Still standing when it was needed. With leverage, $22 million net to Samantha on $1.39 million committed.

If he'd lived to 88: the cash value compounds to approximately $190 million. The death benefit follows it — roughly $200 million. The death benefit in a properly designed policy is not fixed. It grows with every year the structure runs. That is the point of minimum sizing — all the premium goes to work, and work compounds.

The $800,000 a year they were promised wasn't an impossible number. The design made it impossible. And it made the death benefit impossible too — because a policy designed around commission cannot survive long enough to pay either one.
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Non-NY states onlyMaleStandard rate class or betterAges 20–70
$M
Leverage assumption
Conservative is the illustrated default. Actual scenarios may vary. Some cases exceed both estimates significantly.
Total outcome at 88
untaxable legacy + income
Estimated annual income from 59
untaxable — every year
Your annual carry
per year × 5 years
The difference leverage makes
Without leverage
Full premium out of pocket
Still the right move
With bank-backed leverage
Committed capital only
Same outcome
For the analytically curious
Annualized IRR (untaxable)
Taxable equivalent at 37%
Estimated structure cost
Illustration only. All figures are estimates. Non-NY state, Male, Standard rate class or better, age as entered. Not financial, legal, or tax advice. Results are not guaranteed.

The Untaxables — Self-Made Wealth. Structured Forever.

You built it without a blueprint.
Structure it the same way.