Darrow Wealth Management

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.

Understanding The Tax Implications Of Selling Your Business Maximize after-tax proceeds when selling your business through deal structuring, proactive tax and liquidity planning, and the right advisory team.

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.

Where to Save After Maxing Out Your 401(k) | Darrow Wealth Management Where to put money after maxing out a 401(k): brokerage account, traditional or Roth IRA. For high earners, a brokerage account is typically the best option.

"How much do I need to retire?"

It's one of the most common questions we hear — and the honest answer is: it depends on how much you plan to spend.

This article focuses on how much you might need to retire at 60. There's no single magic number, but we’ll walk you through the math — including Monte Carlo simulations across hypothetical portfolios between $2M to $15M to illustrate what different asset levels might support in annual spending.

Retiring at 60 isn't wildly early, but it does come with some unique challenges: you're still 2 years away from Social Security eligibility, 5 years from Medicare, and hopefully, decades away from the end of your retirement. For a healthy 60-year-old couple, there's a 74% chance at least one of them lives to 90.

Here are some key factors that contribute to determining how much is enough:

✅ Spending assumptions (which matter more than savings targets)
✅ Sequence-of-returns risk
✅ Bridging the healthcare gap before Medicare at 65
✅ Assets in taxable accounts for early retirement flexibility
✅ Monte Carlo risk simulations for a more realistic picture than straight-line calculators

Read the full breakdown here:

How Much Do I Need to Retire Comfortably At 60? | Darrow Wealth Management How much money do you need to retire at 60? Spending is the main driver determining whether a comfortable early retirement is attainable.

With companies like SpaceX, OpenAI, and Anthropic expected to go public, 2026 is shaping up to be a landmark year for IPOs — and for employees with stock options and equity on the line. 📈

One thing we always tell clients: you only get one shot at this. The planning you do (or don't do) around a liquidity event can meaningfully affect how much of your equity becomes lasting wealth.

Our Kristin McKenna, CFP® put together a pre-IPO financial planning checklist for Forbes that covers what employees should be thinking about before their company goes public:

💡 Understanding your equity type and what it means for taxes

⌛ Exercise timing and AMT exposure

💲 Cash flow planning for the costs of exercising and timing of tax payments

🔒 Lock-up period strategy

📊 Start building a diversification plan before the window opens

🤝 Assembling your advisory team early

✅ Read the full checklist:

Pre-IPO Financial Planning Checklist For Employees Pre-IPO employees can use this checklist to organize equity, plan exercises and taxes, evaluate tender offers, diversify concentrated stock and prepare for an IPO.

What is direct indexing — and why are high-net-worth investors using it to generate tax alpha? It comes down to harvesting losses at the individual stock level. Kristin McKenna explains the mechanics and ideal conditions for this strategy.

Tax-Loss Harvesting Through Direct Indexing The S&P 500's performance often diverges from that of its constituents. Direct indexing takes advantage of this by harvesting losses stocks with losses.

#1 Tax Planning Tip for Employees with Equity: Before selling in an IPO or tender offer, find out if your shares qualify to be 100% tax-free (up to $10M or $15M) using the Qualified Small Business Stock (QSBS) tax exemption.

Qualified Small Business Stock: QSBS Tax Exemption for Startup Shares | Darrow Wealth Management Qualified small business stock can save millions in taxes. Find out if your stock or options qualify a QSBS gain exclusion under Section 1202.

Everything you need to know about your restricted stock units (RSUs)

Restricted Stock Units: Taxes, Vesting and Key RSU Facts | Darrow Wealth Management What are restricted stock units? How RSUs are taxed, single/double-trigger vesting for public & private company employees, RSUs vs restricted stock, options & PSUs.

Wish you did more tax planning last year? That means it's a good time to start thinking about 2026!

What You Need to Know About Capital Gains Tax | Darrow Wealth Management Reducing tax on capital gains tax in 2026: how short-term and long-term capital gains tax rates work and capital gains tax versus income tax.

How to reduce tax by donating highly appreciated stock.

How to Donate Stock to Charity: Donor-Advised Funds | Darrow Wealth Management Donating stock and appreciated assets to charity with a donor-advised fund. Tax benefits and rules for deducting gifts of stock to charity.

2026 looks like it's finally going to be the year for IPOs!

If you have startup equity, the biggest mistake you can make is missing out on Qualified Small Business Stock (QSBS).

💰 What’s at Stake: $10M in capital gains can be 100% federal tax-free (possibly state too)

❌ Myth: "My company is too big now"

✅ Fact: It only matters what the company was worth when the stock was issued to you. This is important – if you were granted stock options but didn’t exercise in time, no QSBS for you

Quick QSBS Check: ✅ U.S. C-Corp? ✅ Assets

Qualified Small Business Stock: QSBS Tax Exemption for Startup Shares | Darrow Wealth Management Qualified small business stock can save millions in taxes. Find out if your stock or options qualify a QSBS gain exclusion under Section 1202.