Real crypto expertise in a financial advisor shows up in the hard, unglamorous parts: tracking cost basis across wallets, handling the tax on staking and sales, keeping a concentrated position from swamping the rest of the plan, and making sure the coins can actually be found and passed on. “We can help with crypto” on a website says none of that. The questions below separate an advisor who has done the work from one who has added the word.
It’s rare, whatever the websites say
Mentions of crypto are common. Verified working depth is not. In our study of fee-only firm websites, crypto tied for the least common specialty firms backed with a quote on their own site.
That doesn’t mean only 1% of advisors can help. It means you should expect to ask, not assume.
The four places expertise shows up
Cost basis
Every sale needs a basis, and crypto makes it hard: coins move between exchanges and wallets, and exchanges often can’t see what you paid elsewhere. Since January 1, 2025, the IRS expects basis to be tracked wallet by wallet rather than pooled, and Revenue Procedure 2024-28 set out how to assign existing basis to each wallet. Brokers now report sales on Form 1099-DA. An expert can tell you how they’d reconcile your history and which records they’d need.
Income and taxes
Crypto is property for US tax purposes, so selling, swapping or spending it can be a taxable sale. Staking rewards are income when you gain control of them (Revenue Ruling 2023-14), and selling them later is a second event. Lending, liquidity pools and airdrops each have their own wrinkles. Expect an advisor to know where the guidance is settled, where it isn’t, and when to bring in a tax professional who handles digital assets.
Concentration
A position that has grown to a large share of your net worth is a planning problem whatever the asset. The questions are the same ones an advisor asks about concentrated company stock: how much you can afford to lose, how to diversify without a tax hit all at once, and what the rest of the plan looks like if the price halves.
Custody and inheritance
Coins that no one can access are gone. A plan should say where the keys or accounts are, who can reach them if you’re incapacitated, and how they pass under your will or trust without exposing them in the meantime. This is where many plans with crypto fall down.
Questions that separate depth from branding
| Ask | A good answer includes |
|---|---|
| How would you reconcile my basis across exchanges and wallets? | The records they’d need, the method, and the 2025 wallet-by-wallet change |
| How are my staking rewards taxed, and when? | Income at fair market value on receipt; a separate gain or loss on sale |
| How does this position change the rest of my plan? | Its share of your net worth, and a diversification path with the tax cost |
| What happens to these coins if I die tomorrow? | Access, documentation, and how they pass under your estate plan |
| Where would you bring in someone else? | A tax preparer or attorney who works with digital assets |
Depth shows up quickly in these answers. Branding doesn’t survive the second question.
Integration is the point
A crypto-only conversation isn’t the goal. The value is in how digital assets fit with everything else: the tax-aware drawdown plan, retirement accounts, charitable giving, the estate plan. An advisor who treats crypto as a separate bucket is missing the reason you’re hiring them.