Sideshift launched as a local jobs marketplace at the University of Wisconsin-Madison. To get the supply side (students), the founders physically broke into dorms in the mornings, posing as faculty to distribute flyers. For the demand side (businesses), they knocked door-to-door on local bars and restaurants to pitch them as early adopters. This guerrilla campus approach netted around 3,000 students and ~20 businesses in Madison. They then scaled this exact playbook across Big 10 and SEC campuses — Michigan, Iowa, Georgia, Texas, Ohio State, Indiana — spending roughly 10 days at each campus doing the same land-and-grab: dorm flyers in the morning, business door-knocking during the day. After six months of this, they had around 10,000 students on the platform but almost no meaningful revenue from businesses.
Sideshift
UGC marketplace connecting brands with zero-follower creators for high-volume organic content
8 moves, in order
- Pre launch / MVP (2023)Physical flyering and door to door
Broke into university dorms posing as faculty to hand out flyers to students, while knocking on local business doors during the day to sign up bars and restaurants as early employers on the local jobs marketplace.
~3,000 students and ~20 businesses in MadisonUsers 3.0k users - Post graduation expansion (Summer 2024)Physical campus expansion
Went full-time after graduating and ran the same dorm-flyer + door-to-door playbook across ~8 other Big 10 and SEC campuses (Michigan, Iowa, Georgia, Texas, Ohio State, Indiana, etc.), spending ~10 days per campus.
~10,000 students on platform total; businesses still not paying meaningfully (~$10/month max)Users 10k users - Pivot discovery (~1 year before interview)Organic product usage tech twitter
Noticed Tech Twitter / indie hackers were organically using the student marketplace to hire college students for UGC content — without being prompted. The team observed this usage pattern in platform analytics and decided to lean into it rather than force the local jobs model.
Identified new use case that became the pivot; early UGC brands started shaping V2 of the product - UGC pivot / V2 buildProduct iteration on organic demand
Re-engineered creator profiles (from student job profiles to creator profiles showing top videos, posts, and experience), built proper brand tooling, and opened the platform beyond college students to creators of all types. Started actively recruiting UGC-oriented brands like Brex, Suno, Pixart, Paramount Pictures.
Platform repositioned as UGC marketplace; ~800 active paying brand customers eventually - Growth / scaling UGC (Last summer before interview)Owned ugc campaigns on tiktok
Nick personally posted 4x per day across 5 TikTok accounts (20+ posts/day) to understand and prove the UGC model firsthand. Got a video with ~5M views within 3 weeks. Then used Sideshift's own creator network to run large UGC programs promoting Sideshift itself, generating 50–60M views/month from their own campaigns.
First viral video hit ~5M views in ~3 weeks; own programs now drive 50–60M views/month, creating a growth flywheel - B2B sales scalingWord of mouth and referrals
Gave every customer a personal Slack channel, shared Nick's personal phone number with all customers, and maintained 1:1 relationships. This generated strong word-of-mouth and referral loops — customers who didn't convert would still refer others. Inbound became 80% of sales vs. 20% outbound.
80% of sales are inbound; ~800 active brand customers; $8M ARRUsers 800 users - Product expansion / operating systemProduct led retention
Expanded beyond creator recruitment to build a full operating system for brands: analytics, creator management, messaging, payouts, legal, tax, and 1099s — making Sideshift a one-stop shop so brands never need to leave the platform.
Brands running programs of 5–100 creators entirely within Sideshift; case studies include Voodoo (0→90M views in 1 month), All In Motion/Target (25M views in first month), Yapper (80M views/month) - Creator supply growthUgc creator acquisition via owned ugc
Ran large UGC programs using Sideshift's own top creators to promote the creator-side value proposition (earn $20–35K/month posting content). Mobile app built around gamification and training to convert everyday people into creators.
700,000 zero-based creators on the platformUsers 700k users
None explicitly stated — no prior audience or niche network. The main structural advantage was being enrolled students at a large university, which gave them organic access to the supply side (college students) and proximity to local campus businesses. Co-founder Drew provided rare early technical depth for a non-technical founding team.
organic_ugc_tiktok
The local jobs marketplace V1 never achieved meaningful revenue — top subscription was $10/month and the math showed it would take ~7 years to reach $1M ARR. Door-to-door expansion across college campuses for 6 months failed to produce a viable business. Local business owners were not paying or retaining on the platform.
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