How the Best CEOs Delegate
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
Jonathan Swanson, founder of Thumbtack and CEO of Athena, sits down with a16z's Erik Torenberg to discuss his philosophy of building leverage through strategic delegation. (02:14) Swanson's journey began in the West Wing, where he witnessed world-class executive assistants in action, setting his bar for what delegation could accomplish. (02:42) Now running a 4,000-person company while investing and raising four kids, Swanson has built his entire career around the principle that "if you don't have an assistant, you are the assistant." (04:31)
- Core theme: The transformative power of delegation as a system for unlocking ambition and compounding productivity at scale
Speakers
Jonathan Swanson
Jonathan Swanson is the CEO and founder of Athena, the fast-growing platform that pairs ambitious people with world-class personal assistants. Previously, he co-founded and scaled Thumbtack into one of the major home services marketplaces over the past decade. His delegation philosophy was shaped by his early career working in the West Wing, where he observed the president's executive assistants and set his bar for what elite assistance could accomplish.
Erik Torenberg
Erik Torenberg is a General Partner at a16z (Andreessen Horowitz) and hosts conversations with founders and industry leaders. He focuses on investments and insights around the future of work, entrepreneurship, and technology platforms.
Key Takeaways
Start Delegating Immediately, Regardless of Budget
The cardinal sin of delegation is believing "it will be faster or better to do it myself." (08:53) While this is often true initially, it's the only way to build leverage. Swanson advocates starting with whatever budget you have - $20/month for ChatGPT, $10/hour for Upwork freelancers, or $3,000/month for professional services like Athena. The key is overcoming the activation energy required to teach someone else your processes, even if it's slower at first.
Delegate by Algorithm, Not by Task
Advanced delegation involves exporting your internal decision-making processes. (06:55) Instead of saying "help me plan this dinner party," create an algorithm: "I like 6-8 people, similar funding stages, similar employee counts." This allows your assistant to make decisions independently using your criteria, creating scalable systems that improve over time.
Ambition Grows with Leverage, Not Vice Versa
Swanson observed that "the more leverage I got, the more ambition I got, and it just compounded." (03:02) Contrary to popular belief, having assistance doesn't just support existing ambition - it actually unlocks new levels of ambition by freeing mental bandwidth from administrative tasks. This creates a positive feedback loop where delegation enables bigger thinking.
Voice Delegation is Superior to Text
The most effective delegation method is voice notes, allowing 2-3x faster communication than typing. (09:27) Swanson would walk between meetings at Thumbtack, voice-noting takeaways and follow-ups to assistants, ensuring work was delegated before the next meeting started. This prevents the accumulation of tasks that typically happens throughout the day.
Build Long-term Compounding Relationships
The second biggest delegation mistake is switching assistants every 6-12 months. (08:53) Swanson has worked with his primary assistant Marnie for a decade, creating deep institutional knowledge and trust. This compounding relationship enables increasingly sophisticated delegation, from basic calendar management to planning his wedding and helping with his children.
Statistics & Facts
- Athena receives 50,000 assistant applications per month and hires approximately 1 in 300 candidates, maintaining extremely high selection standards. (55:53)
- A couple decades ago, having half a dozen assistants cost around $500,000, but now through services like Athena, you can have your own assistant for $3,000 per month. (03:38)
- Swanson operates with half a dozen specialized assistants - one for work, one for home, one for kids/family/travel, and one for finances, with a chief of staff coordinating across all of them. (07:53)
