Key Takeaways:
- H&R Block’s ‘Make It Legit’ Contest gives three gig workers free business formation, tax assistance, and a professional marketing makeover, including a custom logo and commercial.
- A major IRS rule change now requires gig workers earning $5,000 or more via third-party platforms to report income, greatly lowering the previous $20,000 threshold.
- By structuring as a business, gig workers can access deductions, tax credits, and financial tools that reduce their tax burden and improve profitability.
The gig economy, or the labor market of temporary, flexible jobs, is booming, but many independent workers don’t realize they’re already small business owners in the eyes of the IRS.
H&R Block, in partnership with ad agency Oglivy, has launched the “Make It Legit” contest, offering three winners professional business services and marketing support to help them take their gig to the next level.
Open for entries until May 4, 2025, the nationwide contest isn’t just a competition — it’s a platform designed to empower independent workers.
The three winners will receive free business formation services, year-round tax expertise, and customized branding, including a new logo, brand colors, and a professionally produced commercial.
In a press release, Wendy Fitch, vice president of brand, content, and insights at H&R Block, emphasized the importance of gig workers recognizing their status as business owners.
“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.”
This initiative comes at a crucial time, as a recent IRS rule change requires gig workers and casual sellers using third-party payment apps to report earnings of $5,000 or more, significantly lower than the previous $20,000 threshold.
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According to a January 2025 H&R Block study by Morning Consult, nearly half of gig workers were unaware of the change, and 50% still didn’t fully understand it even after learning about it.
Without proper business structuring, many gig workers are missing out on valuable deductions and tax credits, limiting their income potential.
To highlight the impact of the contest, H&R Block partnered with three unique content creators who have transformed their creative passions into thriving small businesses:
- @PicklePete112 - A bagpiper who performs in a pickle costume at events and businesses.
- @DeadGregs - A culinary historian reviving forgotten historical recipes through engaging content.
- @InspireByTyler - A 3D artist who creates intricate paintings using synthetic hair as a medium.
These entrepreneurs received full branding makeovers, tax support, and professional commercials spotlighting their unique hustles.
How Every Gig Can Go Legit
H&R Block released the “Make It Legit” commercial in partnership with Pickle Pete.
In the 60-second ad, Pickle Pete leans into his unique brand, playing the bagpipes in his signature pickle suit while embracing the classic small business commercial style.
With a professional logo, tagline, and dramatic voiceover, the ad playfully reinforces the idea that even the most unconventional gigs deserve to be taken seriously.
The ad wraps up with a call to action, inviting gig workers to enter the contest for a chance to “Make It Legit.”
@picklepete112 If you received a 1099 in the mail this year, the IRS sees you as a small business—and @H&R Block wants to help you start looking like one. It's why they made me this small business commercial, and why they're giving away a few more to some lucky gig workers. Wanna look legit and give your gig an upgrade? #hrbpartner ♬ original sound - Pickle Pete
The gig economy is evolving, and with stricter tax regulations, workers must shift their mindset from side hustlers to small business owners. Those who embrace this change by formalizing their business can unlock significant financial benefits.
This includes access to small business tax deductions, funding opportunities, and brand credibility.
Previously, H&R Block's "Responsibility Island" reunion episode uses humor and a Tinder collaboration to make tax season more relatable and engaging for younger audiences.
Meanwhile, a study by DesignRush reveals that digital marketing agencies across the U.S. could see significant savings from the proposed 2025 corporate tax reform.
