Insights
Insights
Clear-eyed analysis of self-directed retirement investing — the opportunities, the rules, and the fine print — written for investors and the sponsors who serve them.
Checkbook control in practice: speed, and what it costs
The IRA-owned LLC puts transaction speed in your hands — along with every compliance decision the custodian used to stand between you and. Here’s the honest ledger.
Read →SEP, SIMPLE, or Solo 401(k): choosing the small-business plan
Three plans, three philosophies: maximum simplicity, employee inclusion, or maximum capacity. The right one falls out of four questions about your business.
Read →Naming a trust as your IRA beneficiary
Sometimes the right heir is a trust — for control, for protection, for a minor. The tax rules will honor the choice, but only if the trust is built to be seen through.
Read →Moving alternative assets into a trust
Signing the trust was the easy day. A trust only controls what it holds — and retitling private assets into it is a project with a different checklist per asset.
Read →After the raise: servicing retirement-account investors
Winning IRA money is a sales problem. Keeping it clean is an operations problem — and the sponsors who master the second one raise easier the next time.
Read →What qualified custody means for a fund manager
LP interests, capital calls, side letters, K-1s: private funds are operationally unlike anything else an account holds — and custody built for securities tickets shows it.
Read →The HSA shoebox strategy
The least-known HSA rule is the most powerful one: there is no deadline to reimburse yourself. Pay cash today, keep the receipt, and let the account compound for decades.
Read →Leaving a job: the COBRA decision
COBRA is a right, not a default. Sixty days of decision window buy you time to compare three paths — and the right answer depends on math most people never run.
Read →The limited-purpose FSA: the pairing most HSA savers miss
HSA rules forbid pairing with a general FSA — so most HSA owners skip FSAs entirely. There’s a version built precisely for them, and it’s money on the table.
Read →Taking RMDs when the account is illiquid
Required minimum distributions don’t care that your IRA’s money is inside a building. Plan the cash — or plan the in-kind alternative — before the deadline plans for you.
Read →Solo 401(k) or self-directed IRA: which chassis for alternatives?
Self-employed investors get a choice of vehicle for alternative assets. The right answer turns on contributions, loans, and one tax acronym.
Read →How to vet a sponsor before you direct your IRA
Your custodian executes the investment you choose; it doesn’t vet the people behind it. That job is yours — and it’s more checkable than most investors think.
Read →What owning real estate inside an IRA actually involves
The concept takes one sentence: your IRA buys a property. The execution has rules at every step — and the rules are where the tax advantages live or die.
Read →Lending from a self-directed IRA
Promissory notes turn a retirement account into the bank. The economics are simple; being a good bank is the part that takes discipline.
Read →Titling: the paperwork detail that breaks transactions
Self-directed deals rarely die on economics. They die at the signature block — when an asset is titled to the wrong owner. Get the name right and everything else gets easier.
Read →What a qualified custodian actually does
“Your IRA needs a custodian” is one of the least-explained sentences in retirement investing. Here is the job description — and, just as important, what is not in it.
Read →Fair market value: the number your IRA must report every year
Public securities price themselves. The private assets in a self-directed IRA don’t — and the annual valuation isn’t optional.
Read →Beneficiaries and the illiquid account
Naming a beneficiary takes two minutes. Inheriting an account full of real estate or private funds takes considerably longer — unless the owner planned for it.
Read →Five questions before you move a self-directed IRA
Transfers between custodians are routine — for cash and stocks. When the account holds private assets, the move deserves a pre-flight check.
Read →What a self-directed IRA really is — and the myth it isn’t
The account doesn’t invest for you. That single fact explains most of the mistakes people make with it.
Read →The alternatives boom, explained
Money is migrating from the public markets to the private ones. Here is what “alternatives” actually means — and what it costs.
Read →The rules that bite: what a self-directed IRA can’t do
The prohibited-transaction rules are short, old, and unforgiving. They cause more self-directed disasters than bad investments do.
Read →Beyond stocks and bonds: the self-directed menu
A field guide to what a self-directed IRA can hold — and the specific risks that ride along with each.
Read →The tax that can follow your IRA
A tax-advantaged account is not always a tax-free one. Two rules — UBIT and UDFI — can hand your IRA a bill.
Read →How sponsors raise capital from retirement accounts
Trillions of dollars sit in retirement accounts. For issuers, self-directed IRAs are a channel to reach them — with rules attached.
Read →For founders: tapping retirement capital without tripping the wires
Retirement savings can fund a business. Do it the wrong way and you can disqualify the account — or worse.
Read →Six year-end moves that make every retirement dollar count
As December closes, a short checklist can lower this year’s tax bill and set up the next. Here are six moves worth the hour.
Read →The high-deductible bargain
A bigger deductible buys you a smaller premium and a tax shelter. Whether that trade pays depends on arithmetic most people never do.
Read →HSA or FSA? The difference is ownership
They look alike on the enrollment screen. One is an account you own for life. The other is an arrangement that expires.
Read →What your FSA actually covers
The eligible-expense list is broader than most employees assume and narrower than they hope. Both errors cost money.
Read →The December scramble
Use-it-or-lose-it is a real rule with real exceptions. Knowing which one your plan uses is worth several hundred dollars.
Read →The election you can’t change — until you can
Benefits elections are locked for the plan year. Federal rules carve out a list of life events that unlock them, and the window is short.
Read →The number that changed dependent care
For two decades the dependent care FSA limit sat at $5,000. In 2026 it is $7,500 — and the planning math is no longer marginal.
Read →Five ways employees leave benefits money on the table
The benefits package is compensation. Most workers accept a fraction of it, and the shortfall compounds.
Read →The retirement account hiding in your health plan
An HSA is taxed three times less than anything else in the code. Used correctly, it is not a health account at all.
Read →Educational only. This page is general information, not individualized investment, legal, or tax advice. Rules depend on your account type, transaction, tax year, and circumstances — consult a qualified professional.