Darrow Wealth Management

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Darrow Wealth Management Asset Management & Financial Planning. Specialty in Sudden Wealth Events. Wealth management = asset management + financial planning). Fee Only. Fiduciary.

Registered Investment Advisor. While we maintain a diverse client base, we specialize in working with individuals experiencing a sudden wealth event from stock options, sale of a business, or an inheritance. Learn more about working with a CERTIFIED FINANCIAL PLANNER™ professional at our website. Offices in Boston, MA and Needham, MA. Working with investors across the United States. https://darrowwealthmanagement.com/contact/

Expecting a big payout from selling a business, stock, or a home? If you have ties to Massachusetts, the 4% Millionaire ...
10/15/2026

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.

The Massachusetts 'millionaires' tax will ensnare taxpayers who exceed $1M in income after selling a home, business, stock options and other windfalls.

Should you sell your business?Most owners start with the price.What will a buyer pay? What's the business worth?But if t...
10/09/2026

Should you sell your business?

Most owners start with the price.

What will a buyer pay? What's the business worth?

But if the sale has to fund the rest of your life, there's a better first question:

How much do you actually need?

70% of business owners say they need to sell to retire, according to a 2023 Exit Planning Institute study.

Yet the purchase price and what you walk away with are two very different numbers.

Here's a simplified example from our latest article:

$20 million purchase price
Minus $4 million rolled into the buyer
Minus $1.5 million in escrow
Minus a $2 million earnout (not guaranteed)
= $12.5 million cash at closing

After estimated federal taxes, about $9.5 million is left to work with.

That's less than half the headline price.

And it's before attorney fees, banker or broker fees, state taxes, and working capital adjustments.

So what can that support?

In our illustration, a $10 million portfolio supported about $470,000 a year over a 25-year retirement, or $325,000 a year over 45 years. (Before taxes, in today's dollars. For illustrative purposes only.)

There's another piece owners often miss.

The business may be paying for part of your life today. Cars, insurance, whole family on the phone plan.

Waiting has its own risk, too. Half of business exits are forced by one of the five Ds: death, disability, divorce, distress, or disagreement.

The best time to sell is on your own timeline.

In the full article, Kristin McKenna, CFP®, President of Darrow Wealth Management, explains how to find your number, what the purchase price doesn't show, and how to lower your risk if you're not ready to sell yet.

Thinking about selling your business? Before you weigh any offer, figure out what you spend, what you'd keep after taxes and deal terms, and whether it's enough.

Trump IRAs are here. Kids born 2025-2028 receive a one-time $1,000 federal contribution, and families can add up to $5,0...
10/06/2026

Trump IRAs are here. Kids born 2025-2028 receive a one-time $1,000 federal contribution, and families can add up to $5,000/year per child with no earned income requirement.

Trump accounts are special new IRAs for kids. Learn the rules and how they differ from 529 plans, custodial Roth IRAs, and UGMA accounts for kids' savings.

Sudden wealth can be…complicated. Guilt over money you don't feel you earned, pressure to live a certain way, the awkwar...
09/23/2026

Sudden wealth can be…complicated. Guilt over money you don't feel you earned, pressure to live a certain way, the awkwardness of being the only one in your circle who suddenly has a lot more zeros than everyone else.

There's even a name for it: sudden wealth syndrome.

Our new guide covers what it is, and the dos and don'ts of handling a windfall.

The dos and don'ts of sudden wealth from a financial advisor and how to avoid sudden wealth syndrome after a windfall.

RSUs and stock options are very different forms of equity compensation, from upside and taxes to risk and planning. Here...
09/18/2026

RSUs and stock options are very different forms of equity compensation, from upside and taxes to risk and planning. Here's a detailed comparison on RSU vs stock options.

RSUs vs stock options: key differences in taxes, control, risk vs upside, and which form of equity is better at startups or public companies.

The Anthropic IPO is set to end SpaceX's brief reign as the biggest IPO in history. For employees, turning paper profits...
09/16/2026

The Anthropic IPO is set to end SpaceX's brief reign as the biggest IPO in history. For employees, turning paper profits into tangible wealth is the main challenge. Here’s our pre-IPO playbook for Anthropic employees, covering the tax treatment of RSUs and options, the lockup, and how to build a sales and diversification plan around your goals instead of anchoring to share prices.

Summary: Pre-IPO Equity Planning for Anthropic Employees Anthropic employees should prepare for an IPO in 2026, as time-vested double-trigger RSUs will be

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 a...
09/14/2026

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.

Trump accounts are special new IRAs for kids. Learn the rules and how they differ from 529 plans, custodial Roth IRAs, and UGMA accounts for kids' savings.

Need money from your account but don't want to pay taxes? A securities-backed line of credit (SBLOC) lets you borrow aga...
07/27/2026

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.

Borrowing against your stock portfolio can free up cash without selling appreciated shares. Here's how a securities-backed line of credit works, and the risks.

If you quit, odds are nothing will happen to your 401(k) unless you initiate it. But if you’ve switched jobs and haven’t...
07/24/2026

If you quit, odds are nothing will happen to your 401(k) unless you initiate it. But if you’ve switched jobs and haven’t touched your old 401(k), consider your options.

If you quit, odds are nothing will happen to your 401(k) unless you initiate it. If you've switched jobs and haven't taken your old 401(k) with you,

The first 90 days after a liquidity event is not the time for major decisions. Use this time to confirm what you have, e...
06/29/2026

The first 90 days after a liquidity event is not the time for major decisions.

Use this time to confirm what you have, estimate your tax bill, keep cash safe, review concentration risk, and organize the key financial details that will shape the next stage of planning.

Here's a checklist for immediate actions to take in the first 90 days after a liquidity event.

Post-liquidity checklist: what to do in the first 90 days after a liquidity event. 7 steps to get organized, manage taxes, protect cash, and outline goals.

Address

200 Reservoir Street, Suite 303
Needham, MA
02494

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm

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