Getting past the “Cardinal Sins of Delegating” with Jonathan Swanson of Athena | E2218
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this episode of This Week in Startups, host Jason Calacanis sits down with Jonathan Swanson, founder of Athena and previously of Thumbtack. (02:02) Jonathan shares his journey from building a $500 million revenue marketplace for local services to creating a revolutionary executive assistant platform. (12:15) The conversation explores how Athena is transforming how busy executives and entrepreneurs manage their time by providing expertly trained remote assistants from around the world. (24:22) Jonathan discusses his unique management approach of working with six specialized assistants, the training methodology behind Athena Academy, and how proper delegation can unlock unprecedented productivity gains for founders and executives.
- Main Theme: The conversation centers on transforming time scarcity into time abundance through strategic delegation and expert-trained remote assistance, featuring insights from Jonathan's journey building two unicorn companies.
Speakers
Jason Calacanis
Host of This Week in Startups and founder of Launch, Jason is an angel investor with over 100 investments per year and operates the global Founder University program across the US, Japan, and Saudi Arabia. He was the first investor in both Thumbtack and Athena, and currently uses two Athena assistants to manage his operations across multiple time zones.
Jonathan Swanson
Founder of Athena and co-founder of Thumbtack, Jonathan previously worked in the White House West Wing alongside the president's executive assistants, which shaped his vision for high-quality delegation. Under his leadership, Thumbtack grew to approximately $500 million in revenue with hundreds of thousands of small business owners, while Athena has scaled from $40 million to over $100 million in run rate.
Key Takeaways
Start with One: "If You Don't Have an Assistant, You Are the Assistant"
Jonathan emphasizes that delegation should begin simply with a single assistant handling the most painful administrative tasks. (13:00) He recommends that hiring an assistant should be your first hire if you're building a company, and if you can't afford one, start with ChatGPT as your assistant. The key is removing cognitive load from passport renewals, scheduling, and inbox management. As you add more assistants, you move from just taking pain away to raising the horizon of your goals and accomplishments.
Delegation is an Investment That Requires Training and Feedback
Getting maximum value from delegation requires treating it as a skill that demands real investment of time and attention. (40:25) Jonathan explains that relationships with assistants compound over time, but only if you provide constant feedback and export your "personal algorithms" from your head to your assistant. He spent a decade developing his current system of six assistants, emphasizing that you must go "full time" and "all in" with lots of feedback to achieve success.
Create Detailed Checklists and Systems for Complex Tasks
The most effective delegation happens through detailed checklists and systematic approaches. (44:51) Jason references "The Checklist Manifesto" as essential reading, noting how checklists reduce mistakes in highly repetitive tasks and explain your thinking to assistants. Jonathan's example of planning dinner parties required specific parameters: 6-8 people, recently funded founders, specific messaging, and automated execution that eventually led to meeting his wife at one of these events.
Focus on Backstop Projects to Maximize Assistant Utilization
When assistants aren't handling urgent tasks, assign them "backstop projects" that provide ongoing value. (32:13) Jason describes having his assistants work weekends on big data projects, like organizing all his podcast appearances into searchable formats and researching competitors' sponsors. These projects support the sales team without requiring highly paid employees to do manual research work, creating systematic competitive advantages.
Reframe Delegation Guilt as Providing Opportunity
Many executives struggle with guilt about delegating tasks, but Jonathan reframes this mindset completely. (19:11) He argues that when you're not delegating, you're actually withholding good-paying jobs from people in developing countries who desperately want them. Athena hires people for the best-paying jobs of their lives, and these assistants are excited to work with founders and be part of their success stories. This perspective shift helps overcome the psychological barriers to effective delegation.
Statistics & Facts
- Athena receives 50,000 assistant applications per month and hires only the top 1% after extensive testing and training. (24:12) This selective process ensures only the highest quality assistants make it through their multi-week Athena Academy training program.
- Athena has grown from a $40 million run rate to over $100 million run rate since Jason's initial investment, demonstrating strong product-market fit in the executive assistance space. (26:46)
- Thumbtack has reached approximately $500 million in annual revenue and supports hundreds of thousands of small business owners, making it one of the most successful marketplace businesses. (02:41)
