H&R Block - "Pickle Pete"

New 1099-K earning threshold thrusts many side hustlers, gig workers and casual sellers into small business owner status

From bagpiping in a pickle suit to reviving lost recipes, gig workers like Pickle Pete and Dead Gregs are among the millions of taxpayers with revenue-generating side hustles who are fueling the rapidly growing gig economy and redefining what it means to be a small business owner. To showcase the talent and creativity of these gig workers—and motivate them to take their gig to the next level, H&R Block (NYSE: HRB), a leading provider of global tax preparation, financial products and small business solutions, today announced the “Make It Legit” contest.

Entries will be accepted until May 4 for the nationwide contest that is not just a competition, but a platform that will help three lucky gig workers “Make it Legit” by providing key professional business services and marketing support.

“Gig workers often do not see themselves as legitimate business owners, even though they are taxed as such. We believe that if you’re getting taxed like a legit business, you should look like one, too,” said Wendy Fitch, Vice President of Brand, Content, and Insights at H&R Block. “H&R Block has provided help and inspired confidence in its clients and communities for seven decades. This unique contest aims to inspire the more than 70 million individuals¹ who classify themselves as gig workers to make it legit, so you can keep every dollar of your hard-earned income.”

With the recent change in the 1099-K reporting threshold, independent workers using third-party payment apps or online marketplaces must now report earnings of $5,000 or more—down from the previous threshold of $20,000. The significant change to the threshold amount means casual sellers, side hustlers and gig workers are now considered small businesses.

A January 2025 H&R Block study conducted by Morning Consult found that nearly half of gig workers, side hustlers and online sellers were unaware of the 1099-K change. Even after learning about it, 50% still said they were not clear on the details as of the start of tax season.² While their creativity knows no bounds, many gig workers may be limiting their possibilities and their income because they are not receiving credits and deductions small businesses can claim, and are leaving money behind.

The three Make It Legit winners will receive free business formation service and access to one of H&R Block’s tax professionals for year-round tax expertise and to file next year’s taxes. Winners will also receive custom marketing materials—such as a new logo, brand colors, custom font and to top it off, their very own commercial shot by a live film crew. Eligible gig workers are encouraged to enter for a chance to win a Make It Legit kit by visiting MakeItLegitContest.com and can find full rules and regulations here.

“With 70 years of tax expertise under our belt, we’ve helped countless individuals transition to small business owners and navigate and capitalize on the unique tax codes related to their expertise,” said Fitch. “As the pioneer of the tax prep category, we’re helping other pioneers benefit from their passions and operate with confidence.”

Make It Legit Contest

To bring this initiative to life, H&R Block teamed up with the following three wildly creative content creators who have turned their unique passions into a legitimate business, by giving them the small business treatment complete with free business formation and tax prep services, in addition to a logo, tagline, and typeface:

1. @PicklePete112, a lively performer who puts a quirky spin on traditional bagpiping by playing in a pickle costume at local businesses and events
2. @DeadGregs, a culinary historian and content creator who specializes in reviving historical recipes, bringing forgotten dishes from past centuries back to life
3. @InspireByTyler, a talented 3-D artist known for creating intricate and bespoke paintings using synthetic hair as a medium

While bagpiping in a pickle suit might not seem like a small business, creators like Pickle Pete get taxed as one. H&R Block treated Pickle Pete to a full brand upgrade as well as his own small business commercial. The one-minute piece shines a spotlight on Pickle Pete’s passion, creativity, and his unique hustle—playing on all the tropes of the small business commercials we know and love. Pickle Pete’s film is live now on H&R Block’s social channels including Instagram and TikTok.

All eligible gig workers looking for the same small business treatment enjoyed by Pickle Pete, Dead Gregs and Inspire by Tyler, including their very own commercial, enter the Make It Legit contest today.

To learn more about H&R Block’s tax preparation services, many ways to file, and year-round financial support, visit hrblock.com. For media assets, visit hrblock.com/tax-center/newsroom and for helpful tips and information, follow H&R Block on TikTok, Instagram, and Facebook.

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¹ Statista: Number of freelancers in the United States from 2017 to 2028

² H&R Block 1099-K Study: Morning Consult Omnibus Results + OnePulse Results