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6 Tax Tips for Professional Influencers

If you earn income as an influencer promoting products or services on platforms such as Instagram, TikTok, and Facebook, then you need to understand your tax obligations in order to keep in good standing with the IRS.

May 21, 2023


Democrats released six years of Donald Trump’s income-tax returns on Friday, providing further insight into the former president’s tax situation.

December 30, 2022 

Powerball Lottery Jackpot Swells to $1.2 Billion​

There have been nearly 40 drawings since August without a winner and the potential payout is getting bigger.

November 1, 2022

2022 Best Cities for Freelancers

The pandemic has created more opportunities for remote, self-directed and freelance work than ever. Today, around 10 million Americans say they’re working for themselves in some capacity.

2022 Best Cities for Freelancers

The pandemic has created more opportunities for remote, self-directed and freelance work than ever. Today, around 10 million Americans say they’re working for themselves in some capacity.

How to Pay Taxes as a Freelancer: Tips for Tax Season

Tax season is right around the corner. So how do freelancers pay taxes? Before the Monday, April 18th deadline rolls around, OutVoice has compiled some helpful advice from tax professionals to help freelancers navigate the ins and outs of doing their taxes.

Venmo, Cash App And Zelle Now Required To Report Transactions Over $600 To IRS And Users Are Upset

A new tax law that took effect at the start of 2022 is not being welcomed by users of mobile payment services. The new provision only affects businesses that accept payment cards or use third-party network settlement organizations for payment of goods and services, according to the Internal Revenue Service.

January 12, 2022 

How to Quit the 9-5 Grind and Not Go Totally Bankrupt

Have you thought of starting your own business or freelancing? Learn the ins and outs of freelancing: taxes, budgeting, hiring and more!

January 11, 2022 

IRS tells payment apps to report business transactions over $600

In 2022, mobile payment apps like Venmo, PayPal, Cash App and Zelle are required to report business transactions totaling more than $600 per year to the IRS. What does this mean for businesses?

January 7, 2022

Qualified Business Income Deduction Could Cut Your Tax Bill by 20 Percent, Business Know-How

The qualified business income (QBI) deduction can save owners of businesses whose income passes through to their personal returns up to 20% on their taxes. Find out how this pass-through deduction works here.

May 12, 2021

NYC Video Podcast

For this week’s episode, we interview Jonathan Medows, a certified public accountant (CPA) who lives and works here in New York City. Jonathan has worked with freelancers for many years and has seen it all when it comes to tax preparation & filings for freelancers.

March 29, 2021

Three Untapped Niches of Opportunity for Your Firm in 2021, Insightful Accountant

Dentistry. Construction. Real estate. Working with clients in these industry verticals can provide your firm with incremental growth. While these niches are certainly solid areas to explore as you look toward increasing your firm’s profitability next year, it’s also worth considering some of the markets where the competition is considerably less in order to get ahead of the curve when it comes to capitalizing on their profit potential.

December 16, 2020

6 Things Every Freelancer Should Know About Money, According to an Accountant, Apartment Therapy

The pandemic has changed the way Americans work. According to research from Stanford University, 23 percent of the United States labor force now works remotely full-time, while another 33 percent aren’t working at all due to the impact of the lockdown recession. And more and more people have pursued freelance work, whether it be as contractors, consultants, or business owners themselves.

November 7, 2020

Employee or Contractor: How DOL’s Proposed Rule Could Impact Self-Employment Status, Zen Business

The Department of Labor has proposed a new self-employment worker classification rule that could impact the status of independent contractors. Here are important “economic reality” tests to know about.

September 25, 2020

How to Get Organized for Next Year’s Tax Season Now

If you filed your taxes last week, congrats: The worst is over. Doing your own independent contractor taxes can feel messy, overwhelming, and, yes, taxing. But it doesn’t have to be that way. The trick is to be prepared ahead of the due date. “It’s not just about banging out a tax return,” Jonathan Medows, MBA, a certified public accountant licensed in New York, New Jersey, and Maryland. “It’s about sound tax and financial planning. That’s just not something you whip up on April 14.”

July 22, 2020

Self-Employed? Here’s What You Need to Know About PPP & EIDL Loans

If you are self-employed and were able to get a loan under the Payroll Protection Program (PPP) or you received an Economic Injury Disaster Loan (EIDL) to offset the financial impact of COVID-19, it is important to understand how they may impact your taxes and how any potential loan forgiveness works.

July 3, 2020

How to file for an extension on your taxes

The IRS has made clear it’s not extending the tax filing deadline past July 15. But if you still need more time to get your return in, filing for an extension is quick and straightforward.

July 4, 2020

How to Do Your Taxes as a Freelancer

In case you hadn’t heard, this year’s tax filing deadline was moved from April 15 to July 15. Many freelancers get overwhelmed at the idea of sifting through their receipts, invoices, and 1099 forms for the year. But tackling it head-on (and maybe hiring a certified public accountant) could save you buckets of money.

March 20,2020

Changes in tax law you should know about for 2019

The IRS is heading into its busiest week of the tax season, with millions of Americans expected to file their federal income tax returns. While the changes in tax law for this year aren’t as significant as they were for the 2018 tax year, which followed the biggest overhaul in a generation, there are some changes people should be aware of. Here’s what changed for the 2019 tax year.

February 17, 2020

The SECURE Act is Changing Retirement Saving Plans for Business Owners and Employees

The SECURE Act, which was passed in December of 2019, enacted new tax laws that affect both employer-sponsored retirement plans and individual retirement plans. Find out how these changes may impact you and your business.

January 13, 2020

Why you should file your taxes as early as possible

The IRS this week started accepting tax returns for the 2019 tax year. So when should you file your taxes? As early as possible, most accountants say.

February 7, 2020

How Tax Reform Changes Alimony and Lawsuit Tax Obligations

The Tax Cuts and Jobs Act made significant changes to the deductibility of alimony and personal lawsuit recoveries, which could have a big impact on tax liability for freelancers who divorce or are involved in personal lawsuits. Here’s what you need to know.

March 7, 2019

Average tax refund is now slightly higher than last year

Americans’ tax refunds are no longer shrinking. The latest data released by the Internal Revenue Service show that the average tax refund issued through the third week of February was $3,143. That’s slightly higher than the average refund at this time last year, which was $3,103.

February 28, 2019

Qualified Business Income Deduction Could Cut Your Tax Bill by 20 Percent

The qualified business income (QBI) deduction can save owners of businesses whose income passes through to their personal returns up to 20% on their taxes. Find out how this pass-through deduction works here.

January 19, 2019

How to tell if you’re winning or losing under new tax law

Some Americans are getting an unwelcome surprise this tax season, with refunds down about 9 percent so far this year. Getting less money back, not to mention having to write a check to the IRS, can sting, especially if a taxpayer was expecting the usual windfall.

February 22, 2019

Is The Pass-Through For You? A Primer On The New Deduction For Freelancers

Tax season is never a dull moment for freelancers. And this year brings a particularly notable new wrinkle: the 20 percent pass-through deduction for small businesses that was included in the 2017 tax reform bill. Like many tax rules, this deduction is a little more complex than it sounds at first. So before you get your hopes up, let’s take a closer look at the potential savings for writers for hire.

February 4, 2019

Shutdown causing chaos at IRS — and may delay tax refunds

Americans are used to procrastinating when it comes to filing their taxes. This year, tax season is expected to see an even bigger delay — thanks to the government shutdown.

January 7, 2019

How to survive in the gig economy

Just how many of us are part of the gig economy now? Turns out, it’s kind of hard to pin down. Despite the long-held belief that it’s eclipsing traditional 9-to-5 work, new Bureau of Labor Statistics data suggests the number of alternative workers—those who earn their living outside of a traditional full-time job—make up just over 10% of total employment.

June 26, 2018

3 Ways to Thrive Financially in the Gig Economy

Just how many of us are part of the gig economy now? Turns out, it’s kind of hard to pin down. Despite the long-held belief that it’s eclipsing traditional 9-to-5 work, new Bureau of Labor Statistics data suggests the number of alternative workers—those who earn their living outside of a traditional full-time job—make up just over 10 percent of total employment.

June 12, 2018


Tax day has come and gone but tax preparers are now swapping stories about the craziest deductions they were asked to include. Jonathan Medows, CPA has heard a few unusual ones in his time. Here are a few.

April 19, 2018


Tax day has arrived. Here’s how the recent federal tax reform bill has changed the equation for some workers, according to Jonathan Medows, CPA.

April 17, 2018

Freelance life incurs burden at tax time

Tax time is usually a difficult period for freelancers when it comes to compliance, but there is some good news this year. Many freelancers say they would rather line up at the DMV or get a root canal than do their taxes, according to a study by FreshBooks, which offers accounting services and surveys self-employed professionals.

April 8, 2018

Thinking of freelancing? Here's what the new tax law does for you

The idea of striking out on your own after being a salaried working stiff for years can be enticing. And it’s all the more so now that the tax overhaul created a 20% deduction for those running their own business. But there’s a lot to consider when figuring out whether you really would do better financially by being self-employed. Ask yourself these questions before quitting your day job.

March 27, 2018

How to Handle Your Freelance Taxes Like a Professional

If you’ve been keeping careful records all year and have no fear of forms, you may feel pretty relaxed this time of year. But if this is the first time you’re putting taxes together for your freelance work, you may be dreading April. To help you get through this tax season and in the future, consider the following tips.

March 7, 2018

New sales tax rules for online sellers

Online sales tax is one of those nagging but important administrative details online sellers have to contend with to stay in legal compliance. For a long time, collecting sales tax was fairly simple for e-commerce sellers: just collect sales tax from buyers in any state where you have “nexus” (a location or other business presence.)

March 13, 2018

How to File Your Taxes for Free

When tax season comes around, a filed tax return is one of the few things you won’t have to pay for.

February 3, 2018

How Taxes Are Changing for Freelancers

The tax reform passed by Congress hasn’t taken effect yet, but freelancers will be among the first to feel its repercussions.

January 30, 2018

What You Need to Know About Filing Your Taxes

Jonathan Medows, of Medows CPA, PLLC, answers questions about what to do now to prepare for the new tax bill.

December 27, 2017

How do you save for retirement as a freelancer?

The freelance workforce is expanding and with that growth comes an increased need for retirement plans that fundamentally differ from the employer-sponsored 401(k) savings model.

June 7, 2017

Estimated Tax Fail? Help is Here!

Self-employed freelancers have a special place in the eyes of the IRS—one that makes them susceptible to higher levels of scrutiny than your average W-2 worker, especially during tax season. With your financial situation laid bare on your tax return, it’s impossible to avoid the ever-watchful eyes of IRS agents, so if you’ve done something like inadvertently not paid estimated taxes for a year or more—otherwise known as an #EstimatedTaxFail—it’s safe to assume that you’ll soon be receiving tersely worded tax notices from the IRS. If you do, don’t despair, but don’t delay your response either.

June 1, 2017

Best Tax Blogs: Top Industry Experts

If you’ve ever tried to make sense of the tax code on your own – while you’re filing your taxes or as you figure out how much of your income you should withhold each year – then you know the feeling of a tax headache. The wording can be difficult, and interpreting it correctly can make anyone feel pain in their noggin.

March 30, 2017

How to Handle Your Freelance Taxes Like a Professional

If you’ve been keeping careful records all year and have no fear of forms, you may feel pretty relaxed this time of year. But if this is the first time you’re putting taxes together for your freelance work, you may be dreading April. To help you get through this tax season and in the future, consider the following tips.

March 7, 2018

The skinny about freelance money: How to get comfortable with income, taxes and expenses

Money. Taxes. Finances. Are you cringing yet? Well, it doesn’t have to be that complicated. Here’s a guide for first-time freelancers.

January 24, 2017

Be A Millionaire Next Year by Michael Berg

You may not be a millionaire now or in six months, but you can become one if you change your mindset and adopt proven financial strategies that have helped countless others become true millionaires.

Money, money, money: How to decide on the right rate to charge as a new freelancer

How much money should you charge? Here’s how to get to a number everyone’s happy with.

December 26, 2016

Freelancing Sweeps the Globe: Are You Ready to Dive In?, Currency Fair

The benefits of a freelancing career are seemingly endless: You get to be your own boss, you get to work in a field that you love or that you are great at (ideally both), and, with enough work, you can make a great living wage from anywhere in the world (that has an internet connection).

July 20, 2016

Asking for a Friend: How Do I Stop Harassment Without Involving the Police in a Gentrifying Neighborhood?

Help! My boyfriend won’t pay his taxes. It’s been six years since he had a full-time job, and ever since he went freelance in 2010, he has not been able to complete his 1099s.

May 5, 2016

Today Isn't the Tax Deadline, But Treat It That Way

Just because April 15 isn’t the tax deadline this year, it doesn’t mean this weekend is an excuse to procrastinate.

April 15, 2016

What it Takes to Create Engaging Content in a “Boring” Industry

Cute kittens. Mouthwatering cupcakes. Some small businesses and organizations have it easy. But what if your business is focused on something a little less tempting — like, say, tax and accounting resources?

April 13, 2016

Common Mistakes Freelancers Make During Tax Time

As the great recession gave rise to the gig economy, CPAs say they are seeing more and more people embrace the concept of freelancing.

March 15, 2016

Telework Tax Laws: How To File As A Freelancer

With the growth of the freelance (or “gig”) economy, more and more people are answering new and different types of questions as they prepare to pay Uncle Sam. Tax issues challenge all types of freelancers and self-employed workers—from those working full-time for themselves to those just picking up small gigs here and there throughout the year.

March 15, 2016

For Small Businesses and Entrepreneurs Some Welcome Clarity

Small-business owners, who often consider taxes among their biggest concerns, didn’t get major new tax breaks this year. But they have gotten something else: greater clarity about deductions and credits, which should help their planning for 2016.

February 19, 2016

It's Officially Tax Season: Get Organized And Get Filing

If you didn’t start making year-end tax plans before December 31, it might be worth your while to start gathering up all your documents now and getting organized. The Internal Revenue Service began accepting tax returns on Tuesday, though technically you could have prepared a return on paper or through tax software and submitted it earlier. However, the IRS wouldn’t accept them until January 19.

January 20, 2016

5 Ways Freelancers Need to Prepare for Tax Season

Let’s be honest: a lot of us are probably not thinking too much about April 2016. Some of us may still be breathing a sigh of relief after hitting the October 15 extension deadline for last year’s taxes! But taking the time to think about taxes now will save you a lot of time and trouble next spring—and that’s time you could spend completing client assignments and earning money.

October 15, 2015

How To Make It In The Gig Economy: 4 Tips For Freelancers

The informal motto of the on-demand economy has a nice ring to it: “Be your own boss.” But if you want to scrape together a living by driving for Uber, delivering groceries for Instacart or buying rich people coffee at Postmates, the struggle can make Sisyphus’ gig seem cushy. Working as an independent contractor — as opposed to being an employee — puts you at a significant disadvantage when the tax man comes calling. You’re also likely to miss out on more affordable health care coverage. But if a few whiffs of the gig economy’s intoxicating aroma has you hooked, here are some tips.

October 1, 2015

5 Reasons a 529 College Savings Plan Is the Best Baby Shower Gift

Those tiny clothes and pint-sized pairs of shoes are undeniably adorable, but odds are expectant parents will receive more than a few pieces to build their baby’s wee wardrobe. So, financially savvy friends and family members should consider contributing to a 529 college savings plan that will be meaningful long after a baby’s done with diapers and dolls.

September 23, 2015

The 4 Big Mistakes Freelancers Make When Filing Their Taxes

Freelancing — it’s great until April 15 comes around and you haven’t got the money to pay the IRS. Or almost as bad, remembering to pay up but getting hit with penalties for not filing quarterly.

September 15, 2015

Ask an Expert: NY capital gains tax if I live in Florida?

After 40 years in my Upper East Side apartment, I received a buyout this year from a firm that wants to develop the property. I was told this was a long-term capital gain. However, I moved to Florida earlier this year. Do I still have to pay New York State capital gains taxes on the buyout if I’ve been a Florida resident for more than half a year?

September 15, 2015

Dear John: Trump’s racial talk is a slippery slope

I was reading my favorite paper this morning (New York Post, of course!) and read with interest the 529 plan advice for the young man enlisting in the Marines. The distribution in excess of earnings would be taxable, as your column reported. However, an important piece of information was left out. There is a potential 10 percent penalty on taxable distributions.

July 17, 2015

Ask a Freelancer: What Are Some Obscure Tax Deductions I Can Use to My Advantage?

Taxes are due next week, but I hope there’s still time for you to take my biggest piece of advice: Don’t do your taxes yourself. Instead, work with a CPA. In 2014, I thought I could do my freelance taxes myself, and ended up requesting a tax extension so I could work with a CPA and make sure my taxes—and my deductions—were correct.

Contently, April 7 2015

Everything Freelancers Need to Know for Tax Season

Sara Horowitz, the founder and executive director of Freelancers Union and the co-author of The Freelancer’s Bible: Everything You Need to Know to Have the Career of Your Dreams – On Your Terms (Workman Publishing Company, 2012), says the tax system hasn’t kept up with the growing numbers of workers getting 1099s. She and Jonathan Medows, at Medows CPA, PLLC, answer freelancers’ questions about preparing their taxes.

March 20th, 2015

How NYC owners and renters can save money on their taxes

Living in New York City is expensive and as the April 15th tax filing deadline approaches—it’s a good idea to consider ways you can save money through deductions and credits. Your savings will vary depending on whether you are a freelancer or salaried employee, and rent or own—and if you own, whether or not you have a mortgage.

March, 2015

8 Things Freelancers Should Know About Filing Their Taxes

Last week we invited CPA Jonathan Medows for a live Q&A to answer all your questions about taxes for freelancers. Here’s what we learned.

February 26, 2015

Thinking of Striking Out Alone? Here's How Much it Costs to be a Freelancer

Andrea Bertola Shaw left the security of a full-time job in marketing and design to become a freelance web developer. She wanted to “live the freelance life” while giving time to her low-paying hobby as an off-Broadway theater director.

October 30, 2014

Is It Possible For Freelancers To Ever Retire?, Fast Company

Not long after quitting my office job to work for myself full-time, I ran into an acquaintance on the street. In her early sixties, she’d been working as a freelancer her whole career. I excitedly shared my news with her, expecting congratulations. Instead she shot me a grim look. “After freelancing my whole life,” she said, “I don’t have a dime saved. I have no idea how I’ll ever retire.”

October 18, 2014

The Long Game: 3 Retirement Options for Freelancers

Last year, TD Ameritrade’s Self-Employment and Retirement Survey revealed that over a quarter of self-employed professionals in the U.S. weren’t saving anything for retirement. For salaried employees, that number drops to 10 percent.

June 20, 2014

The Changing Grand Street Co-ops: Join The Lo-Down For a Panel Talk at the Manny Cantor Center June 2

The Grand Street Cooperatives, boasting 4500 apartments and consuming a large amount of real estate from the East River to Essex Street, loom large on the Lower East Side. If you don’t live in one of four mid-century developments built by the trade unions, the co-ops might seem like a mystifying world. Coming up Monday, June 2, we’re partnering with the Manny Cantor Center at the Educational Alliance for a panel discussion looking at the ways in which the co-ops are changing today.

May 21, 2014

How Airbnb Makes Tax Day So Much Worse

Freelancers’ finances are trying in the best of times, but recently the cash-strapped artists turned novice hoteliers, who rent their spare rooms or even couches to travelers on Airbnb, are experiencing another obstacle.

April 15, 2014

Last-minute tax tips for freelancers

I finished my 2013 tax return yesterday and sent it to my accountant to review – which could explain why I’m walking around today feeling about 1,000 pounds lighter.

April 7, 2014

6 Common Tax Deductions For The Self-Employed

If you’re self-employed, like if you’re a freelancer or independent contractor, one question is likely top of mind at tax time: How can I reduce my self-employment taxes?

March 18, 2014

Developer Offers Free Practice Management System to Tax Firms

TaxWorkFlow, LLC announced today that it will provide its TaxWorkFlow practice management software free to tax professionals this tax season. The offer will be available to 100 tax firms on a first-come, first-served basis and will include a complete version of the software with instructional support to ensure that the system is implemented smoothly.

January 15, 2014

New Year’s Business Resolutions for 2014

Yup, it’s 2014 already! And since sharing a resolution or goal with others often helps with the achievement of that goal, it’s now a tradition to ask our fantastic contributor network of business owners, experts, advisors and entrepreneurs to share their own New Year’s business Resolutions for 2014. Let their resolutions give you inspiration for your own business success and goals this year. Their answers are presented below in no particular order.

January 9, 2014

Tricky Tax Questions for American Expats with Online Businesses

Question: I am an American, self-employed, selling expensive cosmetics on the Internet. I moved to Berlin in late 2012.

January 2, 2014

Southern Baptist Leadership Unconcerned About Clergy Abuse Of Tax Break For Housing

The Southern Baptist Convention (SBC) was quick to denounce Judge Barbara Crabb’s ruling that excluding cash housing allowances to clergy from taxable income is a violation of the First Amendment establishment clause. SBC, as the second largest denomination in the country, is probably the one with the most skin in the game, since they have more clergy serving congregations, than the first largest denomination – Roman Catholicism.

November 27, 2013

Ruling on Clergy Tax Benefit Poses Challenges

Last Friday, a federal judge in Wisconsin struck down an IRS provision that allows clergy members to receive part of their pay as an untaxed “housing allowance.” The judge ruled it unconstitutional because it, “provides a benefit to religious persons and no one else, even though doing so is not necessary to alleviate a special burden on religious exercise.”

November 26, 2013

Operate a small U.S. company remotely overseas

Epoch Times reporter Qin Fei compiled a report) In the past 3 months, Paul McTaggart (Paul McTaggart) has been operating his dental service agency Dental Departures in Bangkok . In the previous 10 months, he managed this small business with only 3 employees and one million dollars in several cities in Mexico. Dental Departures introduced the American people and other Canadians to 27 countries going to the dentist, the dentist is expensive because the United States and Canada, and some countries dental services are cheaper. 

November 19, 2013 (English Translation)

Run Your Business from Overseas Instead of the Local Echo Chamber

For the past three months, Paul McTaggart has run Dental Departures from Bangkok. In the 10 months before that, he operated…

October 14, 2013

Sequester Budget Cuts Mean Losses at Army Bases, in Schools in NY, NJ, Conn.

The White House has detailed the potential fallout in each state from automatic budget cuts set to take effect at week’s end, and the losses in the tri-state include Department of Defense furloughs, along with school funding and public safety cuts.

February 25, 2013

Dodging the tax man: Self-employed Brooklyn freelancers hide out during tax season

Always use cash. Keep bank accounts practically empty. Use fake mailing addresses. That’s how Brooklyn freelancers with five-figure tax bills live off-the-grid dodging the Internal Revenue Service.

February 11, 2013

My LES: Jonathan Medows, The Lo-down

I am a CPA and the Managing Member of MEDOWS CPA, PLLC. We are a Lower East Side based firm (Grand St & Columbia St) and we expanded and moved to our current location in January 2012. My work focuses on tax planning, tax preparation, tax controversies, business planning and structuring. Our clients are freelancers, small businesses and individuals with moderate to complex tax returns.

October 22, 2012

Odd bulge in Weiner tax form

Anthony Weiner likes to do things big — especially when it comes to his tax deductions. The disgraced former congressman’s 2010 tax return shows he took $40,521 in unspecified itemized deductions on an income of $156,117. “It’s definitely a very large deduction,” said Manhattan CPA Jonathan Medows.

June 19, 2011

5 Questions I’ve Never Been Asked: Jonathan Medows

On Aug. 14, 2003, during the hours before a blackout crippled almost half the U.S., I was working at home. I’d taken a vacation day because I needed to file my taxes, and I’d done a perfectly awful job during previous year or so keeping up with that important task, mostly owing to a period of unemployment in 2000 and 2001 and freelancing for a living.

January 6, 2010

New York City CPA Jonathan Medows specializes in helping small business owners and freelancers cope with the economic crisis.

May 12, 2009