About Us

A "rapscallion" is a rogue. But they are daring, fun and lovable. The word derives from "rascal." Here at Rapscallion, we like to think of them as the best kind of rule-breakers and game-changers.

Our team and the entrepreneurs we back are a gang of lovable misfits, bandits with a purpose, buccaneers, outlaws, privateers, scallywags, iconoclasts, and rogues looking to steal customers' hearts.

Taxonomy diagram

The Taxonomy of Rule Breaking

At Rapscallion, we have a taxonomy of rule breaking. There are accidental rule-breakers and intentional rule-breakers. On the intentional side, there are "cheaters" and "game changers." Cheaters break rules and try to hide it. Game changers operate with transparency.

They often change our understanding of the rule. They may push boundaries but they do so legally and ethically. Many game changers have mastered the fundamentals of their game so well that they play at a level we didn't think was possible, inspiring new ways of understanding the core techniques and contours of the game. Still others, change our understanding of what it means to "win." The best game changers, change our understanding of the goal of their game. They deepen our understanding of the "why" of their businesses.

Playful entrepreneur illustration

What Makes a Rapscallion?

So for us, "rapscallions" are curious, contrarian, and willing to challenge assumptions. They are people who have mastered their craft so well that they know how to change the game. They help us feel a bigger "why" that pulls at our hearts and minds.

They are disciplined entrepreneurs with a dash of rogue.

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Fun and Funny

We love the idea of funding rapscallions in part because they are fun and funny. Laughter is a core value for us. There is a lot to stress about when building a business. Heck, there's a lot to stress about in the future of technology and society.

We're committed to working toward an unstintingly positive future for all and looking for laughter along the way.

Let's put the fun back in funding.