Twin brothers Donte and Dominic Morris of Oakland, California entered the proverbial tank seeking a $100,000 investment for five percent equity in their startup, HoopMaps. HoopMaps is a mobile app with a pretty simple goal: Helping you find pickup basketball games near you. After a quick introduction from the twins and an equally brief game of basketball with Mark Cuban and guest shark Derek Jeter, they got down to business.

The Morrises explained that, to date, they had 50,000 registered users on HoopMaps, with the average daily user figure being around 10,000. Though they had a relatively strong user base for the early stage they were at, the sharks were all incredibly skeptical of how the app could make money. The twins had a paid subscription tier in mind for that but didn’t have any good answers as to what benefits that paid tier could offer that would convert free users over to spending money, only offering up the idea of premium user-only games. If the subscriptions didn’t pan out, they planned to monetize the app via advertising and brand partnerships.

Lori Greiner, Kevin O’Leary, Barbara Corcoran, Jeter, and Cuban all opted out in that order, mainly over concerns about monetization. On their way out, O’Leary told them to focus more on return on investment in future investor pitches, while Jeter suggested that they find basketball prospects to endorse the app in exchange for equity in the company.

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