Getting past the “Cardinal Sins of Delegating” with Jonathan Swanson of Athena | E2218
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Getting past the “Cardinal Sins of Delegating” with Jonathan Swanson of Athena | E2218

E2218 • Dec 3, 2025 • 57 mins

Delegating is its own unique skill, requiring training and a real investment of time and attention. On TWiST, Jason chats for a full hour with the founder of one of his favorite startups, Athena, which trains online assistants and pairs them with busy founders and executives. (Jason has 2!) But getting the MOST out of your executive assistants is less obvious than it looks. Jonathan unpacks some of the secrets to “Black Diamond Delegating,” and how he manages to keep 6 different high-level helpers operating at once. Plus, Jason and Jonathan look back at the Open Angel Forum days, where Jason invested in Jonathan’s previous company, Thumbtack, praise the “Checklist Manifesto,” discuss the telltale signs you’ve achieved market pull, and lots more insights.

Key Points

  • Jonathan Swanson emphasized the transformative power of having a highly skilled executive assistant, inspired by his experience working alongside the President's executive assistants at the White House.
  • Athena's mission is to give people more of their most valuable resource, time, by providing them with top-tier human assistants empowered by AI technology.
  • The success of Athena is driven by a rigorous selection and training process for assistants, combined with a strong emphasis on teaching clients effective delegation techniques.
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