In this episode, Todd interviews Rebecca Cassava, the CEO and co-founder of Dealmaker, a platform often described as “Shopify for the capital markets.” Dealmaker enables founders to raise capital online by creating a digital storefront for selling shares and then driving investor traffic—essentially transforming private investment into a frictionless e-commerce experience. Rebecca shares how Dealmaker has become a powerful engine for community-driven capital raising, enabling companies to raise anywhere from a few hundred thousand dollars to tens of millions, including high-profile success stories like Boxabl. She explains how community investors—thousands of small checks rather than a few large institutional backers—create stronger engagement, brand loyalty, and greater control for founders. Rebecca and Todd dive into the realities of raising capital, the psychological barriers founders face, and how to determine if this type of raise is appropriate. They also discuss scaling a technology company, the need for organizational structure, the impact of implementing the Scaling Up framework (including the one-page strategic plan), and why even the best founders need coaches and advisors. For founders stuck in growth plateaus or scared to raise capital, Rebecca offers insight into how community funding provides control, clarity, and the resources needed to scale—without giving away power or compromising vision.