• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
MagazineInvest

Investment Strategies That Will Pay Off Next Tax Season

By
Erik Sherman
Erik Sherman
Down Arrow Button Icon
By
Erik Sherman
Erik Sherman
Down Arrow Button Icon
April 19, 2019, 8:00 AM ET

Tax Day has come and gone, along with appreciable amounts of your money. Given the huge changes enacted under the Tax Cuts and Jobs Act of 2017, tax pros were still trying to figure out what worked (and what didn’t) right up to the filing deadline. To decode the code, we talked to top tax experts to find strategies you can implement now—that just might pay big dividends next April.

Revisit REITs

Pass-through businesses like partnerships, LLPs, and sole proprietorships are the big tax-change winners. If they meet certain standards, they get to deduct 20% of their profits before calculating taxes. “It was intended for small businesses, but it also applies to REITs [real estate investment trusts] if they have the right structure,” says Cal Brown, a financial adviser with Savant Capital Management. With REITs looking at lower tax bills, that can mean more profit to divvy up among investors like you.

Go Local

Many have been hampered by the 2017 tax changes’ $10,000 limitations on state and local tax (SALT) deductions. One way to save on state taxes? Move some of your portfolio to Treasuries and municipal bonds issued in your state, which would be tax exempt at the state level, says Eric ­Bronnenkant, head of tax at online financial adviser Betterment. The savings may outweigh the additional interest you’d earn on taxable higher-yield bonds.

Ask to Pay Commissions

In recent years, that advice would have sounded crazy, as clients gravitated toward fee-based advisers. However, with the deduction for adviser fees gone, paying commissions might make sense, says Paul Gevertzman, a partner at accounting firm Anchin Block & Anchin. Say that your investments earn $10, and you get charged $2 in fees. “If they pay you the whole amount, and you pay an advisory fee [separately], that fee is taxable,” Gevertzman says. But commissions charged as you trade, and deducted from the money you net, don’t get taxed.

Get Educated

One group that will benefit in a big way from the 2017 changes are parents and grandparents of school-age kids, thanks to an expansion of 529 plans. In these state plans, earnings aren’t taxable, and when you take money out to pay for such things as tuition, room, board, and textbooks, there’s no tax implication either. Though 529s were originally designed as higher-ed savings vehicles, “in the new tax law, tax-free withdrawals are now allowed for private school, from elementary through high school,” Brown says. But be aware, gift tax exclusions (now $15,000 a year) may apply.

A version of this article appears in the May 2019 issue of Fortune with the headline “Pain-Proof Your Portfolio—for Next Time.”

About the Author
By Erik Sherman
See full bioRight Arrow Button Icon

Latest from the Magazine

MagazineWarren Buffett
Warren Buffett: Business titan and cover star
By Indrani SenDecember 7, 2025
6 days ago
MagazineMarkets
Why an AI bubble could mean chaos for stock markets—and how smart investors are protecting their portfolios
By Alyson ShontellDecember 3, 2025
10 days ago
MagazineMedia
CoComelon started as a YouTube show for toddlers. It’s now a $3 billion empire that even Disney can’t ignore
By Natalie JarveyDecember 3, 2025
10 days ago
MagazineFood and drink
A Chinese ice cream chain, powered by super-cheap cones, now has more outlets than McDonald’s
By Theodora YuDecember 3, 2025
10 days ago
AITikTok
China’s ByteDance could be forced to sell TikTok U.S., but its quiet lead in AI will help it survive—and maybe even thrive
By Nicholas GordonDecember 2, 2025
11 days ago
MagazineAnthropic
Anthropic is all in on ‘AI safety’—and that’s helping the $183 billion startup win over big business
By Jeremy KahnDecember 2, 2025
11 days ago

Most Popular

placeholder alt text
Economy
Tariffs are taxes and they were used to finance the federal government until the 1913 income tax. A top economist breaks it down
By Kent JonesDecember 12, 2025
22 hours ago
placeholder alt text
Success
Apple cofounder Ronald Wayne sold his 10% stake for $800 in 1976—today it’d be worth up to $400 billion
By Preston ForeDecember 12, 2025
18 hours ago
placeholder alt text
Success
40% of Stanford undergrads receive disability accommodations—but it’s become a college-wide phenomenon as Gen Z try to succeed in the current climate
By Preston ForeDecember 12, 2025
18 hours ago
placeholder alt text
Success
At 18, doctors gave him three hours to live. He played video games from his hospital bed—and now, he’s built a $10 million-a-year video game studio
By Preston ForeDecember 10, 2025
3 days ago
placeholder alt text
Economy
For the first time since Trump’s tariff rollout, import tax revenue has fallen, threatening his lofty plans to slash the $38 trillion national debt
By Sasha RogelbergDecember 12, 2025
14 hours ago
placeholder alt text
Economy
The Fed just ‘Trump-proofed’ itself with a unanimous move to preempt a potential leadership shake-up
By Jason MaDecember 12, 2025
12 hours ago
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

© 2025 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.