In this episode of May I Have Your Retention Please, I sit down with Drew Levin — the 23-year-old co-founder of Side Shift, one of the fastest-growing creator marketplaces in the U.S. Built for Gen Z, Side Shift connects student creators with brands, apps, and companies looking for distribution — and it’s doing it at scale.
In May alone, they hit the Top 50 on the App Store, pulled in 45,000 downloads, and had to pause marketing just to keep supply and demand balanced. Oh, and they’ve done it all bootstrapped.
But it didn’t start with virality. In fact, it started with something far less glamorous: handing out flyers from a Honda Civic on college campuses and pitching local bars. Drew walks us through how that hustle eventually evolved into a powerful growth engine and why their early cease-and-desist moment actually fueled the pivot.
We dig into:
- Why Drew and team used flyers, cold calls, and TikToks to onboard their first 14,000 users
- The exact viral video that brought in 20,000+ users overnight
- How they engineered a K-factor loop by bundling analytics into their platform
- Why being in New York changed everything — and why founders need to be near their users
- How Side Shift focuses on power users, not just more users — and why 20% of their creators drive 80% of the revenue
- The pros and cons of UGC at scale, the rise of AI-generated content, and why TikTok might eventually clamp down
- Why Side Shift is now one of Stripe’s fastest-growing companies globally
We also talk about:
- Why Drew believes revenue > fundraising, and why chasing a $100M business is often smarter than aiming for $1B
- The team's obsession with customer feedback, and why they still call almost every new user
- Tactical lessons on product-led growth, campaign performance metrics, and how to avoid “dead” marketplaces
- Hot takes on the future of AI content, TikTok saturation, and why founders need to make content themselves before outsourcing it
You’ll also hear:
- The internal metric that predicts long-term creator retention
- How Side Shift thinks about virality, saturation, and market equilibrium
- Drew’s take on why AI-generated UGC might eventually break TikTok
- A few spicy mentions (including cloning rumors) and how they’re protecting their creators
This isn’t a fluff story. It’s tactical, raw, and loaded with lessons for anyone building a consumer product in 2025 — especially those in marketplaces, social apps, or the creator economy. Whether you’re experimenting with TikTok, trying to hack your App Store rankings, or wondering how to scale without a budget, Drew’s story offers an honest and incredibly useful roadmap.
Quickfire at the end:
- Would he sell for $10M after tax? (spoiler: no)
- Favorite apps right now
- What app he checks first thing in the morning
- The philosophy that shapes how he and his co-founders operate
If you’re a founder building anything in consumer, creator economy, or mobile, this one’s for you. And if you’ve ever questioned whether TikTok is still worth it… you’ll have your answer by the end of this episode.
Listen now and subscribe for more no-fluff convos with the best consumer builders of 2025.
