In 2023, Canyon Pergande was a senior at the University of Wisconsin–Madison, pulling shifts at a college bar. He watched the place try to hire the way every local business still did: paper applications behind the counter, listings buried on Indeed, a university job portal nobody opened. The bar couldn't find students. Students couldn't find the bar.
Pergande and his UW-Madison classmate Nick Lawton kept circling the same thesis. Gen Z was surrounded by part-time work and had no decent way to reach it, and local businesses were fishing in the wrong ponds. Their fix was almost boringly simple: a two-sided marketplace that dropped college jobseekers and small businesses into the same feed, with one common application. The whole pitch, as they'd later put it, came down to putting a couple of extra dollars in Gen Z's pocket. This was the beginning of SideShift.
Fall 2023: Pergande and Lawton founded SideShift in Madison as a two-sided marketplace connecting college students with local businesses for part-time work.
November 2023: Closed its first funding round. Over time the company raised roughly $2.18M across three rounds, backed by investors including BullMont Capital and Madworks Accelerator.
Winter 2024: Joined the Madworks Accelerator's Winter 2024 cohort, an 11-week program that came with a $6,500 grant and the company's first real footing on legal and governance basics.
2024: Launched a mobile app and went door to door in college towns selling local businesses $20-a-month SaaS plans, grinding a few thousand students onto the platform one bar and coffee shop at a time.
Spring 2025: The business was, in the founders' own words, slowly dying, a failing model wrapped around an app that didn't work. The $20-a-month job board wasn't scaling, and the runway was thinning.
May 2025: Rather than fold, SideShift pivoted from college job board to UGC creator marketplace, turning its pool of hungry students into a content army brands could hire to produce short-form video at volume.
Late 2025: Shipped V2 of the app with Duolingo-style creator gamification (Bronze-to-elite tiers, XP per video), real-time earnings, and a built-in training course, then launched SideShift Bootcamp to manufacture creators instead of just recruiting them.
Today: 700,000+ creators, 1,500+ brands, 5B+ views in 90 days, and $100M+ paid out. Recent 30-day windows have seen 2,500+ creators earn $2M+ and over 1B views, with brands like Brex, Replit and GPTZero running campaigns and Remini clocking 20M installs in 60 days.
SideShift didn't find its billion-view business by inventing something new. It found it by looking again at what it already had. The dying job board's real asset was never the listings, it was a few thousand hungry Gen Z kids with phones and free time. The moment the founders stopped selling $20 SaaS plans and started renting that army out to brands, the same people became the product. A pivot isn't an admission you were wrong. It's proof you finally noticed what was already working.