Podcast Summary: a16z Show

Episode Title: How the Best CEOs Delegate
Host: Andreessen Horowitz (A16z) partner
Guest: Jonathan Swanson (co-founder, Thumbtack & Athena)
Release Date: December 10, 2025

Overview

This episode explores the art and science of delegation as the fundamental superpower for CEOs and ambitious professionals. Jonathan Swanson, co-founder of Athena (a global assistant company) and Thumbtack, shares his evolution from working beside elite White House EAs to building teams with thousands of assistants and embracing the convergence of human and AI delegation. The conversation covers frameworks for maximizing leverage, practical delegation tactics, organizational culture, talent pipelines, and the critical mindset shift from personal output to compounding leverage—an indispensable guide for founders, operators, and anyone looking to scale their impact.

Key Discussion Points & Insights

1. The Philosophy and Practice of Delegation

• Delegation as a System for Living

  • Swanson describes delegation not as a perk, but as a necessary operating system for high achievement.
  • “If you don't have an assistant, you are the assistant. And you don't want to be the assistant.” – Jonathan Swanson [04:14]
  • Delegation unlocks ambition, compounding opportunities as you free up bandwidth.

• Democratizing Access

  • Top-tier executive support, once reserved for presidents or billionaires, can now be accessed for a fraction of the cost via services like Athena and AI.
  • “A couple decades ago, you had to be Mark Andreessen or Vinod Khosla to have a half dozen assistants and that cost you half a million dollars. Now with a company like Athena, for 3,000 bucks a month, you can have your own assistant.” – Jonathan Swanson [03:32]

2. How to Delegate Effectively

• Task vs. Algorithm Delegation

  • Entry-level delegation is by task (“help me plan a dinner”); advanced is by algorithm: systematically exporting preferences to enable repeatable, high-quality outcomes.
  • “The more advanced way to delegate is called delegate by algorithm, where you actually export your own internal preferences... Once the algorithm’s fully exported from your head, it’s just rinse and repeat.” – Jonathan Swanson [06:54]

• Principles & Frameworks

  • Cardinal Sin: Believing it’s faster/better to do it yourself.
    • “It takes more effort to delegate...But the only way you get leverage is by going through that work.” – Jonathan Swanson [08:28]
  • Compounding Relationships: Stick with assistants over the long term for compounding trust and productivity.
    • “It’s the compounding that creates incredible leverage. I've been working with Marnie for a decade...She knows everything about me.” [08:28]
  • Optimize for Future, Not Present: Don’t just solve immediate pain; delegate to unlock new possibilities.
  • Voice Over Text Delegation: Delegating by voice note radically increases speed and context.
    • “The best way to really delegate is using your voice...If you look at all the super delegators at Athena, they are all just delegating by voice all day long.” [09:36]
  • Specialization: Start with a generalist assistant, then split roles (work, home, finances, etc.) as complexity grows. Use chief of staff to orchestrate.

3. The Human-AI Continuum

• Gradual Automation:
  • Delegation will increasingly flow from humans to AI, just like the gradual evolution of self-driving cars.
  • Founders should begin with whatever they can afford—even $20/month AI tools (ChatGPT).
• Athena’s Vision:
  • Building assistants that proactively spot tasks (“watches your screen,” suggests delegations) without you voicing them.
    • “We've built an internal demo...it screenshots the screen, and when it identifies things you should be delegating...it automatically adds it to your assistant’s task list.” [10:10]
  • Long-term: combining best of human touch (empathy, context, proactive judgment) with AI’s recall, organization, and automation.

4. Overcoming Psychological Barriers

• Delegation is sometimes seen as indulgent, but withholding tasks limits both personal potential and the assistant’s opportunity.
  • “You not delegating and not giving leverage is holding you back, but it’s actually preventing you from creating a job for someone who’s excited to help you.” [14:01]
• The importance of accountability and coaching: Great executive assistants become confidantes and partners, offering both operational and emotional support.
  • “It's more than just accomplishing things. This was their closest confidant who saw behind the scenes on everything.” [16:57]

5. Time Management & Prioritization

• Intentionality with Time:
  • “What's the most valuable asset in the world? It's not gold or Bitcoin or Nvidia clusters. It's time.” [22:18]
  • Know your optimal mode—whether that's jam-packed meetings or unstructured dreaming time.
  • Regular retrospective calendar audits (inspired by Keith Rabois): ensure your schedule reflects your true priorities.
• Goals & Power Law Focus:
  • Focus on the single most impactful goal per quarter, rather than spreading effort thinly.
    • “There’s typically one thing every month or quarter that if you accomplish is worth more than everything else combined. And figuring out what that one thing is is what you should do.” [21:08]

6. Building and Scaling Teams

• Global Talent & Labor Arbitrage:
  • Leverage global talent (e.g. Filipino assistants) for maximum cost-effectiveness and service enthusiasm.
• Hiring Executives & Assistants:
  • The higher the role, the less you can trust interviews. Use references, ask for 360-degree reviews, and design project-based evaluations.
  • “The more senior they go, the better they are at interviewing...So you actually have to discard the interview more the more senior they go.” [28:18]
• Chief of Staff vs. EA:
  • EA is more administrative/support, Chief of Staff is more strategic/offensive, often a future founder. EAs are for long-term compounding, Chiefs of Staff are “high slope,” short tenure.

7. Lessons from Iconic Operators

• Limitless ambition is built, not innate; delegation makes ambition possible, not the other way around.
  • “As people get more leverage with Assistant, their ambition increases.” [41:01]
• The best operators challenge conventional scheduling structures, say ‘no’ frequently, and periodically reinvent their approach to time management.
  • “The thing I think you can learn from Mark and other people is just challenge the defaults occasionally.” [50:35]

8. Founder Mental Health & Psychological Resilience

• Repeated failure and near-death moments are to be expected; resilience is about staying in the game.
  • “There was lots of near misses where we almost died...and it was like, you just got to stay in the game and if you can stay in the game, you can eventually win.” [52:07]

Notable Quotes & Memorable Moments

• “If you don't have an assistant, you are the assistant.” – Jonathan Swanson [04:14]
• “The cardinal sin of delegation is that it will be faster or better to do it myself. And the reason it's a blocker is because it's true…but the only way you get leverage is by going through that work.” – Jonathan Swanson [08:28]
• “The most valuable asset in the world...is time. We can always raise another round or do another trade, but you can't raise another decade.” – Jonathan Swanson [22:18]
• “There’s typically one thing every month or quarter that if you accomplish is worth more than everything else combined. And figuring out what that one thing is, is what you should do.” – Jonathan Swanson [21:08]
• “As people get more leverage with Assistant, their ambition increases.” – Jonathan Swanson [41:01]
• “If you’re starting a business, you should hire an assistant. And if you've got 20 bucks a month, use ChatGPT...When you have the resources for $3,000 a month, then you should work with a company like Athena” – Jonathan Swanson [55:30]

Important Timestamps & Segments

| Timestamp | Segment Description | |-----------|-----------------------------------------------------------------| | 00:18 | Introduction to the future of democratized delegation | | 02:12 | Swanson’s delegation origin story & high standards from the White House | | 03:32 | How Athena makes high-level assistance accessible | | 04:14 | 'If you don't have an assistant, you are the assistant' maxim | | 06:54 | ‘Delegate by Algorithm’ in practice | | 08:28 | Overcoming the delegation blocker and compounding relationships | | 09:36 | Importance of delegating by voice for speed | | 10:10 | Preview of Athena’s proactive, AI-driven delegation | | 14:01 | Cultural fit and the moral argument for hiring assistants | | 21:08 | Power law prioritization and focusing on one key goal | | 22:18 | “Breaking the chains of time”: Time as the primary asset | | 28:18 | Hiring executives, reference checks, and project-based evaluation| | 33:34 | Co-founder relationship realities and lessons | | 37:34 | Chief of Staff vs. EA: differences and hiring criteria | | 41:01 | Delegation breeds, not follows, ambition | | 52:07 | Staying in the game: resilience and near-miss experiences | | 55:30 | Practical guide: Stepwise approach to hiring assistants |

Conclusion

Jonathan Swanson makes a compelling case that great delegation is both an organizational and personal superpower. Start small—with AI or affordable services—and relentlessly build systems, relationships, and self-discipline to compound your impact. Ultimately, the goal isn’t just to get more done, but to expand your ambition by removing self-imposed constraints on your time and energy.

This episode is a masterclass in the mindset, tactics, and cultural architecture that define elite CEOs and world-class organizations.

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