Topic: Email Whitelist

The hosts discuss technical difficulties with their newsletter delivery, blaming MailChimp and the general "broken" state of email. They claim that companies like Substack and MailChimp must pay large sums to be "whitelisted" by Google and Outlook. A mention of Start9, a company providing hardware for home-based self-hosting, highlights the difficulty of running independent email servers in an ecosystem controlled by Big Tech.

Listener Richard Gabriel reported difficulties in sending donation notes, which were blocked by server filters for "disallowed content." The hosts acknowledged that the current system for processing notes via PayPal and email is being revamped for the first quarter of 2023. They advised donors to avoid using profanity in notes to ensure they pass through automated spam and content filters.

The email industry is characterized as a "criminal enterprise" where large providers like Google and Yahoo effectively extort small businesses through whitelisting services. It is alleged that companies must pay significant fees to ensure their emails bypass spam filters and promotional tabs. The CEO of MailChimp is criticized for a perceived cavalier attitude toward these delivery challenges, leading to speculation that a premium "guaranteed delivery" tier is forthcoming.