Caelen King discusses various monetization strategies for web applications, including software licensing, white labeling, subscriptions, and different types of advertising models. Software licensing can be difficult to scale and negotiate recurring revenue. White labeling puts the developer more in control but remains complex. Subscriptions provide recurring revenue but are vulnerable to churn. Different advertising models like pay-per-click, pay-per-impression, and pay-per-action each have pros and cons in terms of risk, reward, and customer traffic patterns. The best approach may be a hybrid of subscriptions and pay-per-lead.