• by Fern Siegel , April 7, 2025

H&R Block approached Ogilvy with a challenge: reach the 70 million gig workers now considered small businesses, per Statista, due to 1099-K tax changes.

The agency's answer is the Pickle Pete spot and a national contest.

"Many of these gig workers are also Gen Z content creators, so we collaborated with H&R Block on a social-first approach, and some unexpected influencer partners, to reach these important taxpayers," Doug Fallon and Steve Fogel, group executive creative directors, told Agency Daily. "If the IRS treats them as small businesses, we wanted to work with H&R Block to help them look like a small business, too.”

Given the recent tax changes, many independent workers using third-party payment apps or online marketplaces must now report earnings of $5,000 or more — down from the earlier $20,000. That change means casual sellers, side hustlers and gig workers are now considered small businesses. Yet a January 2025 H&R Block study conducted by Morning Consult found that nearly half of these people are unaware of their new tax situation.

Ogilvy teamed with three creative, niche-obsessed content creators who have turned their passions into businesses — and will need to file a 1099-K. The creators include @DeadGregs,  a recipe revivalist, @InspireByTyler, synthetic hair artist, and @PicklePete112, a bagpiping pickle, running on TikTok and Instagram, H&R Block's social channels and YouTube.

In addition, the tax prep service kicked off the Make It Legit contest, offering three gig workers the chance to win a professionally produced commercial, free business formation and custom-marketing materials through May 4.

“Gig workers often do not see themselves as legitimate business owners, even though they are taxed as such,” said Wendy Fitch, vice president of brand, content and insights at H&R Block. The contest's goal is to help gig workers “make it legit, so you can keep every dollar of your hard-earned income.”