Native AI challengers can win against incumbents by targeting "sticky hero problems" that business owners face, rather than focusing on individual users who select their tools. By solving these complex, high-impact issues—often associated with tasks performed by inefficient workers dubbed "Cousin Richie"—AI can demonstrate its value and displace existing systems. Emphasizing the potential of conversational interfaces and the ability to handle messy workflows positions AI as a vital component in modern business operations.