Most families of multigenerational wealth allocate a portion of their balance sheet to venture capital. However, whether to allocate is only the first decision. The harder ones are how much, where the opportunities come from, and how each deal is evaluated. We are grateful to Mark Meyerdirk, co-founder of Collaborative Capital, for joining us to work through some of these questions. Mark has spent four decades as a securities attorney forming and counseling growing companies, and close to a decade introducing venture capital opportunities to some of Kansas City’s most successful families. Since 2017, his club has placed close to $90 million in roughly thirty companies, applying a clear standard: no company presents unless a member has already invested, the company must have revenue or contracts in hand, and the member who brings the deal answers on the record for their own stake. This episode looks at venture capital with eyes wide open: most companies never return investors’ capital, the horizon runs a decade or more, and the path to exit is rarely straight. We discuss how deals reach families, how valuations are tested, why patient capital is a requirement rather than a virtue, and how to size each position so that a loss leaves the plan intact.