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Paysquad

Consumer Tech

Operating Website

Post-pitch story

Paysquad pitched a group-payments app built around a familiar frustration: getting friends to actually pay you back. Whether it is rent, a group trip, or a shared gift, Paysquad lets one person front the cost and collect from the group, with the app chasing the stragglers so you do not have to. The founders pitched it as social finance for a generation that splits everything. On the show, Paysquad did not land a deal — the investors worried about competition from the big payment apps and the difficulty of building a consumer finance habit. But the founders kept going. Since the episode, Paysquad has reportedly raised about $500,000 from other investors and continues to operate, pushing its group-payments product to users. It is a tough market — Venmo, Cash App, and Zelle loom large — but Paysquad's focus on the group-collection moment gives it a specific job to do rather than trying to be a general wallet. For fans of the show, Paysquad is a classic example of a no-deal company that did not take the panel's pass as the final word.

Founders

The trail

  1. Original pitch

    Sep 16, 2026 · Season 16

    #187 Paysquad: Buy Now, Pay Together

    Episode link
  2. Outcome · today

    Operating

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Sources