#tax-loss-harvesting

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#tax-optimization #tax-aware-investing #wealth-management #concentrated-stock #direct-and-custom-indexing
Venture
from24/7 Wall St.
3 days ago

I Have 90% of My Net Worth in One Stock. How Do I Diversify Without a Massive Tax Bill?

Clients increasingly request tax-aware diversification, especially when concentrated stock positions create large embedded gains and tax friction.
Retirement
from24/7 Wall St.
3 days ago

The Tax-Loss Harvest That Cost a 66-Year-Old Retiree $2,400 in Wash-Sale Penalties She Never Saw Coming

A wash-sale rule can disallow IRA tax-loss harvesting when substantially identical shares are repurchased within 30 days via DRIP, reducing expected tax savings and compounding.
Retirement
from24/7 Wall St.
4 days ago

The $40,000 Tax Move That Comes After Your 401(k) Hits Its Limit

Direct indexing replaces an S&P 500 ETF with constituent-level holdings to harvest taxable losses while maintaining index exposure.
Retirement
from24/7 Wall St.
6 days ago

How Tech Executives Convert RSU Vests Into $700,000 of Tax-Free 401(k) Retirement Income

Default sell-to-cover on RSU vesting leaves concentrated employer stock, creating concentration risk without reducing ordinary income tax owed on vest day.
Cryptocurrency
fromBitcoin Magazine
1 week ago

Strategy (MSTR) Buys $43 Million More Bitcoin After Saylor Defends Potential BTC Sales

Strategy bought 535 bitcoin for about $43 million, increasing holdings to 818,869 BTC while maintaining a net-accumulation stance amid fair-value accounting losses.
from24/7 Wall St.
2 months ago

Stacked Up Some Massive Capital Gains? 3 Ways to Take Some Chips Off The Table Tax-Efficiently

The key to selling underperforming holdings at a loss and using those losses to cancel out capital gains on a dollar-for-dollar basis is to bring one's capital gains level down as close as possible to zero. Additionally, it's possible to use $3,000 of capital losses per year to offset other ordinary income, so there's the potential here with such a strategy to actually lower one's overall tax burden by selling the right securities at the correct time.
Miscellaneous
Business
from24/7 Wall St.
4 months ago

It's the Final Countdown: 3 Stocks to Buy Before We Wrap Up 2025

Rebalance before year-end, diversify across investment styles, and consider buying Alphabet and Restaurant Brands to improve long-term risk-adjusted returns.
Retirement
fromAbove the Law
5 months ago

5 Year-End Tax Moves That Could Save Lawyers Thousands In Retirement - Above the Law

Use year-end tax moves—estimate taxable income, harvest losses, optimize retirement accounts, gift strategically, and coordinate tax and investment planning to reduce 2025 taxes.
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