CoreWeave is public. The lockup is gone. Now comes the diversification problem.

What's publicly known

Where CoreWeave employees stand in mid-2026

If you joined CoreWeave pre-IPO, you're now roughly 15 months post-listing. The immediate drama — IPO-day RSU settlement, the lockup countdown, the first quarterly estimated payment — is behind you. The current planning landscape looks like this:

1. IPO-era RSU lots have crossed the one-year mark. RSUs that settled at the IPO (or in the first days of public trading) had a basis at or near the $40 IPO price. Any shares still held from that batch have now been held for more than one year, which means gains on those shares qualify for long-term capital gains rates — not ordinary income. That's a meaningful difference at the income levels most CoreWeave employees face.
2. Ongoing vests are ordinary income at market price. RSUs that vested after the IPO settled at the market price on vest date — that's ordinary income, withheld at the IRS supplemental rate (22% federal). For most senior technical employees, the real marginal rate is 35–37%. The gap is real and accumulates over every vest.
3. The stock has been volatile. From $40 at IPO, CRWV ran to roughly $184 and then pulled back toward $100. Employees who are still holding large positions have seen both the upside and the reversal. That volatility is precisely what makes systematic diversification valuable — and what makes "I'll wait for it to go back up" a plan that has cost a lot of equity holders a lot of money before.
4. ESPP shares are approaching tax inflection points. If you enrolled in the 2025 ESPP near the IPO, the two-year holding period from the offering date likely extends through early-to-mid 2027 for most participants. Shares sold before that date (or before the one-year-from-purchase mark) are a disqualifying disposition: the 15% discount and any gain are taxed as ordinary income. Shares held through both thresholds get the more favorable qualifying treatment. Check your plan documents for the exact calendar.

The three tax treatments on your CRWV shares

Most CoreWeave employees now hold shares in multiple buckets with different cost bases and holding periods. Understanding which is which changes the order you sell in:

• IPO-settlement RSUs (basis ~$40, held >1 year). Gain on these shares — if you sell now at, say, $100 — is approximately $60/share of long-term capital gain. At a 20% federal LTCG rate plus 3.8% NIIT, plus state (California is 13.3% and taxes LTCG as ordinary income), the effective rate is meaningful but substantially better than ordinary income rates. These are your most tax-advantaged shares.
• Post-IPO RSU vests (basis = vest-day price). These settled at whatever market price existed on the day they vested — anywhere from the $40s to the $180s depending on when your vest dates fell. The ordinary income tax was (or should have been) paid at vesting. Gain above the vest-day price, once held a year, becomes LTCG. But if the stock dropped after a vest date, you may have a loss — sell those lots to harvest it.
• ESPP shares (basis = discounted purchase price). ESPP basis mechanics are complex: in a qualifying disposition, part of the discount is ordinary income and the rest is LTCG. In a disqualifying disposition, the full discount plus gain is ordinary income. Don't sell ESPP shares without understanding which side of the calendar you're on. The plan document and your broker's cost-basis records are the reference.

Our concentration calculator models a multi-year glidepath by lot, showing net proceeds after estimated federal LTCG, NIIT, and state tax. Use it to stress-test different diversification speeds against your target allocation.

Key decisions for CoreWeave employees in 2026

1. Set a concentration target, then work backward. "CRWV as a percentage of net worth" is the number that matters. Most equity-comp specialists suggest something like 5–15% in any single position for a long-term plan. If CoreWeave is currently 60% of your net worth, that's a glidepath question — not a binary sell/hold question. Run the numbers in the concentration calculator.
2. Sell your highest-basis lots first — unless they're underwater. When you sell, your broker will default to FIFO unless you specify lots. For CoreWeave employees, this likely means defaulting to your oldest (low-basis IPO-era) lots — creating the largest taxable gain. Actively selecting lots (highest basis first, or underwater lots for tax-loss harvesting) materially changes the after-tax outcome. This requires an account with lot-level visibility and intentional sell orders.
3. Harvest losses on post-IPO vests that settled high. If any of your RSUs vested when CRWV was trading above $150 and the stock is now below that, those lots may carry unrealized losses. Selling them offsets gains elsewhere — including on appreciated IPO-era lots or other positions. The 30-day wash-sale rule applies if you're repurchasing CRWV.
4. Model estimated tax quarterly. RSU vests each quarter = ordinary income each quarter. If your withholding is running at 22% supplemental federal and your bracket is 37%, you owe the difference by the next quarterly payment date. One large vest in Q1 means an April payment is due — not next April. An advisor can help you calculate the right safe-harbor amount.
5. Think about charitable giving for the most appreciated lots. IPO-era CRWV shares with a $40 basis now hold a large embedded gain. Donating shares directly to a donor-advised fund (DAF) or public charity lets you deduct the full fair-market value, avoid the capital gains tax, and still redirect the proceeds charitably. For employees in high brackets with philanthropic intentions, this is worth modeling before selling.

Ready to map out your CRWV glidepath?

Get matched with a fee-only fiduciary who works post-IPO equity — lot selection, LTCG vs. ordinary income trade-offs, ESPP timing, quarterly estimates, and a diversification plan that fits your whole picture. Free, no obligation.