Hi all. Coming with some questions primarily and clearly about my taxes over the coming few years. I've tried to be supremely clear, while also providing a lot of detail. I tried posting this in places related to financial independence, namely daily or weekly threads. No such luck getting any responses. Perhaps this community would be more interested in providing a POV based on the context. Not sure. Any-who, trying again to get some info from the internet!
I'm hoping to get some feedback on my upcoming equity situation. I'm going to keep this matter-of-fact and just the facts, until the end. I'll acknowledge up front that I have struck gold in my current position, and I'm very thankful for that. I also diligently saved for more than a decade in my earlier career, and so I have a lot to show for that on the net worth front. But, now, onto my problems.
I’m looking for a sanity check on my equity + tax strategy over the next ~4–5 years. I’ve done a fair amount of reading (Carta AMT calculator, IRS material, various posts), but I’d appreciate real-world perspective from people who’ve navigated ISO + RSU + AMT overlap.
It seems like I'm going to end up in AMT in April '27. Similarly, I expect to probably hit AMT for most of the years I'd be exercising. RSUs will significantly increase ordinary income in 2027 and beyond, which complicates any ISO exercise timing, I think?
Overall, it kinda feels I'm going to be liquidity constrained due to tax timing for the next 4-5 years! Every year I'll see a TON of money coming in on the exercise / LTCG / RSU fronts, but I'll need to be holding a ton of liquid cash in order to pay AMT bills.
Net worth (approx)
- $40k SGOV (cash equivalent)
- $20k cash (SPAXX)
- $50k taxable brokerage
- $35k HSA
- $90k Roth IRA
- $550k 401k
- ~$350k mortgage on ~$650–750k home @ 4.09%
- No other debt
Income
- $200k–$230k base + bonus
- Broad index investing strategy
- No advisor currently
Equity
- ~2,500 total ISOs
- 25% (~600 options) vesting in Q2 2026, then quarterly
- ~1,200 RSUs
- 25% vesting in Q1 2027, then quarterly
- Strike ~$13
- Current FMV ~$450–$480
Life Desires
- FIRE in ~5 years
- Minimize total tax over time (not necessarily year-by-year optimization)
- Avoid catastrophic AMT surprises
- Maintain liquidity / not be forced to sell at bad times
Questions
- Does it make sense to fully exercise ISOs in 2026, or is that too aggressive?
- How do people typically manage ISO exercise when RSUs overlap (do they deliberately stagger to “smooth AMT”)?
- Is a CPA or financial advisor actually necessary here, or is this manageable DIY with planning tools?
- Am I underestimating AMT risk in RSU-heavy years?
- Any general structural mistakes in this plan?