PickUp - Sports Engagement Platform

In 2018, as sports betting began legalizing across the US, I co-founded PickUp to solve a fundamental problem: fans were hungry for deeper engagement, but media and businesses weren't meeting them there. Fan experiences were fragmented—conversations happened in one place, content consumption in another, and fan sentiment was lost in text message chains and walled gardens. We started with an iOS app for sports predictions, but quickly learned that distribution and user acquisition were major challenges. The real insight came when we recognized that sports publishers already had the audience we needed—they just lacked engagement tools to capture first-party data and monetize that engagement. We pivoted to build a WordPress plugin that converted fan conversations into quantifiable "props" (predictions) that could be embedded directly into articles. A writer covering "Will the Lakers make the 2021 Finals?" could add a PickUp prop right in the article. Fans would make their pick, verify with their mobile number, and immediately start earning points—no downloads or sign-up forms required. The platform was designed for distribution and scale. We built technology that extracted the most timely, relevant sports topics and transformed them into playable propositions distributed across the sports ecosystem. The fan-first approach meant simple, low-barrier entry that met fans wherever they already were, making adoption frictionless. The business model created a three-way value exchange: publishers got 1:55 average engagement time per article and deeper metrics, fans earned points they could redeem in our marketplace for rewards from brand partners, and sponsors got access to qualified, engaged users with quantifiable sentiment data. We successfully raised pre-seed and Series A funding and scaled to over 100 publisher partners, including Sports Illustrated, USA Today, The Lead, MMA Junkie, 49ers Hive, and Raptors Cage. We secured affiliate deals with DraftKings and formed strategic partnerships with major brands including PointsBet, Fanatics, NASCAR, Rogers, Comcast, and Xfinity. At our peak, the platform created 6,795 props that generated 582,275 picks across 8,563 articles, reaching 7.1M users. The metrics validated our thesis that embedded engagement tools could drive meaningful time-on-site and capture valuable first-party sentiment data. Scaling remotely during COVID presented unique challenges, but we adapted and continued growing our publisher network and brand partnerships. However, by 2022, the sports betting market had become increasingly saturated. Despite coming close to an acquisition, we ultimately couldn't close a deal and made the difficult decision to wind down operations. While PickUp didn't end with an exit, the four-year journey taught invaluable lessons about product-market fit, the importance of pivoting based on market feedback, and the challenges of timing in rapidly evolving markets. The experience of building and scaling a venture-backed startup from the ground up was transformative.