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

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

This Week in Startups · Dec 4, 2025

Thumbtack & Athena founder Jonathan Swanson on building unicorns, the power of delegation, and leveraging human + AI assistants to achieve time abundance.

Reframe Delegation Guilt as Creating Opportunity for Others

Founders often feel guilty delegating tasks they could do themselves. A powerful mental shift is to see delegation not as offloading work, but as providing a desirable, well-paying job to someone in the developing world who is eager for the opportunity.

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

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

This Week in Startups·3 months ago

Successful Service Businesses Must Teach Clients How to Use Them Effectively

Athena discovered that providing a world-class assistant wasn't enough; they also had to educate clients on the skill of delegation. This highlights that for complex services, investing in client training is as crucial as the service itself for ensuring customer success.

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

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

This Week in Startups·3 months ago

Use Assistants to Systematically Engineer Personal and Family Experiences

Beyond professional tasks, assistants can systematically achieve personal goals, from making friends by organizing recurring dinner parties to building family bonds through planned activities. This transforms an assistant from a productivity tool into a life-design partner.

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

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

This Week in Startups·3 months ago

Top-Tier VCs like Sequoia Elevate Ambition, Not Just Provide Capital

VCs at the highest level don't just write checks; they fundamentally reset a founder's aspirations. By placing a startup in the lineage of giants like Google and Oracle, they shift the goal from building a big business to creating a generational company.

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

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

This Week in Startups·3 months ago

The "Cardinal Sin of Delegation" is Believing It's Faster to Do It Yourself

It is almost always faster and better to do a task yourself once. However, this is a trap. The "cardinal sin" is failing to invest the extra upfront effort to delegate and train someone, which unlocks compounded time savings and prevents you from ever having to do that task again.

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

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

This Week in Startups·3 months ago

True Product-Market Fit Is When Customers Become Your Sales Team

You've achieved product-market fit when the market pulls you forward, characterized by growth driven entirely by organic referrals. If your customers are so passionate that they do the selling for you, you've moved beyond just a good idea.

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

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

This Week in Startups·3 months ago

AI Will Augment Human Workers Like Autopilot, Not Immediately Replace the Driver

The integration of AI into human-led services will mirror Tesla's approach to self-driving. Humans will remain the primary interface (the "steering wheel"), while AI progressively automates backend tasks, enhancing capability rather than eliminating the human role entirely in the near term.

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

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

This Week in Startups·3 months ago

A Near-Death Business Experience Can Become a Company's Defining Moment

Thumbtack's "Google death penalty"—being completely de-indexed—was a crisis that could have killed the company. Co-founder Jonathan Swanson reframes this intense period as a favorite experience because it forged team unity and resilience, proving that existential threats can become powerful, positive catalysts.

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

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

This Week in Startups·3 months ago