Podcast Summary: "Getting Past the Cardinal Sins of Delegating" with Jonathan Swanson of Athena | This Week in Startups, E2218

Host: Jason Calacanis
Guests: Jonathan Swanson (Athena, Thumbtack), Alex Wilhelm
Date: December 4, 2025
Episode Theme:
Exploring the transformative power of delegation, the evolution of executive assistance, and building scalable processes for founders and startups. Jonathan Swanson shares his journey from co-founding Thumbtack to starting Athena, a company aiming to give leaders “the most valuable asset—time.” The discussion covers lessons on delegation, the intersection of human and AI-powered assistance, and actionable strategies for founders.

Main Themes & Purpose

• Delegation as Foundational to High-Impact Founders: Jonathan Swanson discusses breaking past common delegation mistakes (“cardinal sins”), using assistants to reclaim time, and his startup Athena’s mission to deliver world-class executive support.
• Evolution from Thumbtack to Athena: Reflections on the early funding struggles, UX insights, and Thumbtack’s path to becoming a trusted platform; inference for scaling and building lasting businesses.
• Human + AI Future: How Athena is designing human-powered assistance augmented by next-gen AI tools—and why the “human touch” remains central.

Key Discussion Points & Insights

Early Startup Days & The Value of Angel Investors

• Jonathan Swanson’s Thumbtack Journey

  • Met Jason 12 years ago; Jason catalyzed Thumbtack’s angel round.

    “You catalyzed the whole round. JCAL first investor in. … Now it's doing around half a billion of revenue, very profitable, growing nicely.” — Jonathan Swanson [02:19]

  • Early days were tough—few angels, founders sometimes had to pay to pitch. Jason’s “Open Angel Forum” broke the mold.

    “At that time, the angels there were like maybe a dozen in each of the major cities … It was really hard to figure out who they were, but they were charging founders $5,000…” — Jason Calacanis [02:52]

• Importance of Early Product Thoughts

  • Initial Thumbtack was a directory—a safe, trusted alternative to Craigslist.
  • Delighting users with “extra touches” in UX was a key differentiator.

    “Adding that extra touch can add some magic to the experience.” — Jason Calacanis [06:53]

• Office Stories & Growth Pains

  • Startup “house” offices, humble beginnings—a progression to proper offices and big investors (Sequoia).

Scaling & Raising Ambitions

• Sequoia’s Influence
  • Having investors like Sequoia shifts founder ambitions significantly.

    “Having an investor like that select you … it just raises your ambitions. You're like, let's not go for 100 million in revenue, let's go for 10 billion.” — Jonathan Swanson [08:45]

  • Shift from building to flip (“2-year exit”) to building generational, lasting companies.

Transition to Athena & The Mission of Reclaiming Time

• Origin Story & Inspiration

  • Inspiration from working with White House EAs; sought to bring top-tier assistance to more people.

    “What if I had a team of assistants like the President has? … She [first assistant] really transformed what I was capable of doing … helped me make friends, helped me meet my wife.” — Jonathan Swanson [00:00, 11:05]

  • “Time is the most valuable asset in the world. … Athena’s mission is to give people more of that most valuable resource.” [11:05]

• How Athena Works

  • Athena matches clients with highly vetted, well-trained assistants (primarily in the Philippines, but expanding globally), supported by advanced AI tools.
  • The mission: Let ambitious people “move from time constraint to time abundance.”

• Who Should Use an Assistant & How

  • “If you don’t have an assistant, you ARE the assistant.”

    “Everyone should start with one. … First assistant takes the pain away—passport renewals, scheduling, inbox.” — Jonathan Swanson [12:53]

  • As a team of assistants grows, so does the founder’s “time horizon” and capacity to dream.

    “I only achieved [time abundance] when I had a chief of staff and six. … There is someone handling every part of my life.” — Jonathan Swanson [12:53]

Cost, Structure & ROI: An Investor Perspective

• Cost and Value Proposition

  • Athena assistants currently $3,000/month each.
  • In the Valley, EAs cost $100–$150K/year—often with high turnover.

    “Previously in the Valley, an EA is 100 to $150,000 a year … Athena trains them. Athena matches them… If it’s not a fit, they replace them.” — Jason Calacanis [14:23]

  • 95–99% of tasks can be done remote.

• High Leverage Delegation

  • Example: Restaurant and travel research done thoroughly by assistants; frees founders from menial details.
  • “Cardinal sins of delegation”:
    1. Believing it’s faster to do it yourself (short-term true, long-term false).
    2. Feeling guilty about delegating (“You’re withholding a good-paying job…”).

    “When you're not delegating, you're actually withholding a good paying job to someone in the developing world…” — Jonathan Swanson [18:32]

Athena’s Human+AI Model & Training

• Will AI Replace Human Assistants?

  “Humans are good UX … but behind the human, there are machine assistants we’re building that will automate more and more. … Like Tesla: progressive automation, always a ‘steering wheel’ for some time.” — Jonathan Swanson [21:14]

  • Athena is at “lane assist” (day one); AI can review, augment, and accelerate work, enabling each assistant to scale up their output.
  • Eventually, software may double productivity of all assistants—but always with a strong human interface.

• Training & Selection

  • 50,000 applications/month; only top 1% selected.
  • Four-story training centers; in-person & multi-week programs, led by former business school leaders.
  • Assistants can earn an accredited MBA degree through Athena Academy.
  • Athena invests heavily in AI adoption.

    “I got word from our partner at OpenAI … they said Athena was the fastest ramp of any enterprise they’ve worked with and the highest utilization per employee.” — Jonathan Swanson [25:42]

  • Secret plan: Eventually productize workflow software to offer as SaaS for all global assistants. [25:46]

Growth, Scaling, and Operational Challenges

• Company Growth

  • Bootstrapped to $40M run rate; now >$100M and growing.

    “We’ve exceeded $100 million run rate. … Expect to continue that growth into next year.” — Jonathan Swanson [26:27]

  • Podcast shoutouts and referrals create spikes in demand—once led to assistant shortages and waitlists.

• Expanding Global Supply

  • Athena now sources and trains assistants globally (Philippines, Kenya, Guatemala…); “supply side” investments to prepare for massive scale (up to 500 new assistants/month). [28:39]

Startup Risks, Turnarounds & Near-Misses

• Thumbtack’s “Google Death Penalty” Anecdote
  • Site was completely delisted from Google—a near-company-ending event.

    “Traffic has gone to zero. … Google thought that we had done something inappropriate … the Google death penalty … not that you’re deranked, you don’t exist.” — Jonathan Swanson [29:15]

  • Company rallied, fixed issues, proved their case to Google, and recovered.

    “You just lock arms and you’re like, we’re gonna do it.” — Jonathan Swanson [30:21]

Advanced Delegation Tactics & Practical Output

• Maximizing Value from Assistants

  • Make a list of tasks you dislike; start delegating those.
  • Assistants are “backstops” for ongoing projects—e.g., research, data-cleaning, sales pipeline checks.
    • Example: Collect stories for a parent’s birthday, organize family activities, set up sustained engagements (e.g., 10 weeks of pickleball for bonding).

    “It took me 10 seconds to come up with… going through my dad's Facebook to ask for memories; going to take my assistant six weeks to execute.” — Jonathan Swanson [33:55]

• Measuring ROI & The Importance of Process

  • Use checklists to minimize mistakes; clients must invest time onboarding and giving feedback for compounding results.

    “Checklists really reduce mistakes … If you make a checklist for your Athena assistants … chances of you making a mistake in highly repetitive tasks goes down in a massive way.” — Jason Calacanis [44:39]

  • Best clients are “maniacs” about systematizing delegation—partnership thrives on both sides.

Product Market Fit and Scaling Ethos

• Defining Product-Market Fit

  • When the market “has you by the nostrils” and growth is pulled by demand/referral, not just sales effort.

    “You have product market fit when it feels like the market has you by the nostrils and it's just pulling you.” — Jonathan Swanson [37:55]

  • Early Athena: signed up 1,000 users in 24 hours—market validated with no paid marketing.

• Qualities of Ideal Customers

  • Not everyone is suited for Athena; willingness to delegate and engage in the feedback loop is essential.
  • 10–15% of prospects disqualified if not ready to invest in the relationship/process.

Security, Compliance, & Doing Things the “Right Way”

• Enterprise-Grade Security

  • Athena handles compliance by setting up legal entities and local employment, providing laptops/MDM, and integrating with corporate stacks.

• Market Comparisons

  • If running on a budget, founders can use Upwork, Fiverr, etc.—with caveats. Athena adds value by managing the complexity, vetting, training, and compliance.

    “We vet 400 people for everyone we hire.” — Jonathan Swanson [54:04]

Notable Quotes & Memorable Moments

• On Time:

  “The most valuable asset in the world. It’s not gold or bitcoin or Nvidia clusters. It’s time.” — Jonathan Swanson [11:05]

• Delegation as Leverage:

  “If you don’t have an assistant, you ARE the assistant.” — Jonathan Swanson [12:53]

• On Finding Product/Market Fit:

  “You have product market fit when it feels like the market has you by the nostrils and it’s just pulling you.” — Jonathan Swanson [37:55]

• On Overcoming Crisis:

  “Traffic has gone to zero. … Google death penalty … you just lock arms and you’re like, we’re gonna do it.” — Jonathan Swanson [29:15-30:21]

• On Delegation Guilt:

  “When you’re not delegating, you’re actually withholding a good paying job to someone in the developing world who desperately wants it.” — Jonathan Swanson [18:32]

• On AI’s Role:

  “Humans are good UX … The client's in front, but behind the human, there are machine assistants we're building.” — Jonathan Swanson [21:14]

• On Process:

  “Checklists really reduce mistakes … for your Athena assistants … the chances of you making a mistake in highly repetitive tasks goes down in a massive way.” — Jason Calacanis [44:39]

Timestamps for Important Segments

• [02:19] – How Jason’s investment catalyzed Thumbtack’s growth
• [06:53] – The importance of delight & trust in product experience
• [08:45] – How Sequoia changed the company’s ambition
• [11:05] – Athena’s mission and the value of world-class assistants
• [12:53] – Moving from time constraint to “time abundance” with assistants
• [14:23] – Cost, recruiting, and why Athena is game-changing
• [18:32] – Guilt in delegation and the “cardinal sins”
• [21:14] – The future: Human assistants augmented by AI
• [25:42] – Athena’s AI ramp, training, and future software product
• [26:27] – Athena’s current run rate and referral-driven growth
• [29:15] – Thumbtack’s existential Google crisis
• [33:55] – Real-life advanced delegation: Personal projects, family activities, gifts
• [37:55] – How to recognize true product-market fit
• [44:39] – The power of systems, playbooks, and checklists
• [54:04] – The reality of hiring in global/frontier markets vs. Athena’s full-service model

Tone & Energy

• The conversation is lively, candid, and packed with practical founder advice and war stories. Jason brings enthusiasm and real-world experience as an investor/founder, Jonathan is analytical and humble, with an operator’s perspective. They riff on lessons, swap tales, and keep the advice actionable and relatable.

Final Takeaways

• Best-in-class delegation is about investing in relationships and systems. Assistants—when well-selected, well-trained, and well-managed—can be transformative for founder productivity and life satisfaction.
• AI will amplify, not replace, great human assistants—the Athena model is about augmentation, not substitution.
• Systems, feedback, and deliberate onboarding are key—the best outcomes come from commitment on both sides of the assistant-client relationship.
• Building “generational” companies requires relentless focus–on team, delegation, and raising your own ambitions.
• For founders: The secret to scaling yourself may be as simple (and as complex) as letting go, trusting others, and building your own “playbooks” for leverage.

Memorable Closing Exchange

Jason: "I love you, brother."
Jonathan: "Love you. Thank you so much. Appreciate the support."
[56:46]

For Founders & Operators

If you want to reclaim your time and do more of what matters, consider how delegation—and the systems to support it—can unlock your next level. Whether through Athena or your own methods, the essential lesson is: You get what you put in.

Listen to the full episode for additional practical stories, advanced tips, and the full measure of this high-energy conversation.