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

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Dec 4, 2025

Jonathan Swanson, Founder and CEO of Athena, shares insights on delegating effectively to reclaim time for busy executives. He discusses transitioning from Thumbtack to Athena, emphasizing the importance of pairing human assistants with AI support. Jonathan reveals the concept of 'Black Diamond Delegating' and the gains from managing multiple specialized executive assistants. They explore the significance of checklists and playbooks in maximizing productivity, and Jonathan offers tips for hiring assistants, even starting with DIY options like ChatGPT.

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ANECDOTE

First Assistant Changed Everything

Jonathan hired his first assistant in the Philippines while building Thumbtack and it transformed his capacity to scale the business.
That assistant helped him grow professionally and personally, including helping him meet his wife.

ADVICE

Start With One Assistant

Start with one assistant and treat them as your first hire to remove cognitive load from admin tasks.
Use ChatGPT as a temporary assistant if you lack cash until you can afford a human EA.

INSIGHT

Delegation Creates Time And Opportunity

Delegation friction often comes from doing a task yourself because it's faster once, but that blocks leverage.
Withholding tasks also withholds paid jobs from people in developing countries, reframing delegation as opportunity.

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Today’s show:

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.

Timestamps:

(01:53) We’re joined by Jonathan Swanson from one of JCal’s fav startups, Athena!(02:02) Jason and Jonathan first met during the Open Angel Forum, when Jonathan was working on Thumbtack(06:44) Finding the “little touches” that can help make an app more delightful(9:47) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(12:05) The shift from Thumbtack to Athena was all about time(12:52) How Jonathan delegates to 6 exec assistants at once(14:22) Pricing Athena’s EAs: Jason runs the numbers(15:09) Why Athena made Jason believe in hiring assistants again(18:15) Getting past the “Cardinal Sins of Delegation”(19:38) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.(20:48) Will AI ever be able to replace Athena assistants?(23:41) Inside how Athena finds and trains assistants from around the world(27:01) How JCal became an Athena Ambassador… and almost crashed the system!(30:55) Gusto - Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at https://www.gusto.com/twist(32:11) The magic of having assistants work on “backstop projects” and creative tasks(37:14) How to know when you have achieved market pull(40:05) Why getting the most out of delegating takes real investment and training(44:36) More praise for the Checklist Manifesto(46:26) Jonathan gives us a peek at what “Black Diamond Delegation” looks like(52:14) Jason’s early experiences hiring overseas assistants, from the Mahalo days*Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcp*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: https://www.linkedin.com/in/alexwilhelm/*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis/*Thank you to our partners:(9:47) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(19:38) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.(30:55) Gusto - Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at https://www.gusto.com/twist