President @DarrowWealth. Senior Contributor @Forbes. 2023 InvestmentNews 40 Under 40. Stock options & sudden wealth & cats. Disclosure: https://xitter.cf/t.co/Z4rvjDsnHG
Boston, MA
Joined July 2015
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An employee tender offer lets you control the timing of your liquidity and the price. For private company employees, it's worth considering. darrowwealthmanagement.com/b…
Expecting a big payout from selling a business, stock, or a home? If you have ties to Massachusetts, the 4% Millionaire surtax could impact you, even if you're not a resident. Before a major liquidity event, consider your options for tax planning. darrowwealthmanagement.com/b…
🚨 Anthropic IPO: reportedly on the table for employees: required 10b5-1 sales plan, IPO trading window & unusually long lockup. All this means the big decisions get made early.
My latest for Forbes 👇
forbes.com/sites/kristinmcke…
What to be laser-focused on right now:
• RSU tax bomb at IPO
• Whether to exercise options now
• Your baseline number for a sales plan
• Lockup rules and possible 10b5-1 requirements
• Find an advisory team experienced with managing equity in IPOs & major liquidity events
I put together a pre-IPO playbook for #Anthropic employees: tax treatment of RSUs and options, lockup, AMT on ISOs, and how to build a sales and diversification plan around your goals instead of anchoring to share prices darrowwealthmanagement.com/b…
Parents: Did you know you could add up to $5k/year to a Trump Account for your kids, with no earned income rules? It's an IRA, so not a substitute for a 529 plan, but a great wealth building tool for some families.
forbes.com/sites/kristinmcke…
Need money from your account but don't want to pay taxes? A securities-backed line of credit (SBLOC) lets you borrow against a taxable account instead of selling your positions.
Here's how portfolio loans work and when to sell instead. forbes.com/sites/kristinmcke…
The first 90 days after a liquidity event aren't about making decisions—they're about NOT making them. Confirm what's actually cash. Figure out taxes. Understand concentration risk. Organize THEN plan. My 7-step post-liquidity checklist 👇darrowwealthmanagement.com/b…
Friends don't let friends make these post-IPO mistakes:
⛔ No plan before the lock-up release
💰 Letting taxes (not goals) drive selling
⚓ Anchoring to the IPO price
📉 Underestimating risk
My latest for Forbes 👇 forbes.com/sites/kristinmcke…
Most entrepreneurs are so focused on the GROSS sale price they overlook what they'll actually NET after taxes when selling their business. Here are the key tax implications every business owner needs to understand pre-exit. forbes.com/sites/kristinmcke…
Where should you put extra cash after a 401(k)? There are 3 main options: a brokerage account, IRA, or Roth IRA. TLDR: a taxable account is usually the best option for high earners. darrowwealthmanagement.com/b…
SpaceX Lockup Release Windows:
- 20% post-Q2 earnings
- 10% if stock closes 30%+ above IPO in 5 of 10 consecutive days before first earnings call
- 5 time-based: 7% each at day 70, 90, 105, 120, and 135
- 28% post-Q3 earnings
- 180 days: lockup ends
darrowwealthmanagement.com/b…
After a major liquidity event, parents with young kids should consider superfunding 529 college savings plans. forbes.com/sites/kristinmcke…
Wish you did more tax planning last year? That means it's a good time to start thinking about 2026! darrowwealthmanagement.com/b…
Beware of the AMT tax trap when exercising incentive stock options! Timing tax bills with liquidity is key at startups or ahead of an #IPO
Turbocharge your tax-loss harvesting strategy with direct indexing. Here's when it could add the most tax alpha. forbes.com/sites/kristinmcke…
I'm not a fan of non-deductible IRA contributions. Most people forget to track/report basis or lose records they must keep forever. But the REVERSE rollover can clean it up, saving you from paying tax twice. Here's how it works. forbes.com/sites/kristinmcke…
Since Congress has ignored my pleas to stop overhauling the tax code, I've done some of the heavy lifting for you. Here's several of the biggest changes in 2026, including the bad news for high earners.
forbes.com/sites/kristinmcke…
