#099 Jonathan Swanson: Scaling Thumbtack, 10x Delegation, and Designing an Ideal Life

Jonathan discusses his hero Marcus Aurelius and how stoic philosophy shaped his ability to operate under extreme pressure. He shares the story of Thumbtack being completely de-indexed by Google, losing all traffic overnight, and how maintaining mental composure during crisis became a defining capability.

• •Marcus Aurelius wrote 'Meditations' while running the Roman Empire at war - ultimate example of mental strength under pressure
• •Thumbtack crisis: woke up to zero traffic, Google had de-indexed the entire site, had to onboard 30 new employees while managing the emergency
• •Crisis moments reveal capability - being 'backed in the corner' forces you to discover what you're truly capable of
• •Stoic mindset: 'I got a wife that loves me, kids, and a good mind - everything's gonna be okay' regardless of business outcomes

Jonathan explains how Athena started as a simple income-generating side project when he became Thumbtack chairman, tweeted about it, got 1,000 signups overnight, and evolved through multiple vision iterations. The company went from 'best human assistants' to 'human + AI' after early access to GPT-4 capabilities.

• •Started Athena solely to generate personal income while holding Thumbtack equity pre-liquidity
• •Put up a website in one day, tweeted it out, got 1,000 signups immediately - 'well shit, I gotta hire a thousand assistants'
• •Brought in CEO who had built 25,000-person teams in The Philippines, scaled from $2M to $100M run rate
• •Vision evolved: best human assistants → + delegation training → + AI integration after ChatGPT moment
• •Current vision: 'Best human assistants powered by best AI' - humans as UX layer, AI handling automation behind the scenes

Jonathan describes the radical pivot when a friend on OpenAI's red team showed him pre-ChatGPT capabilities. He hired a PhD to tutor him on LLMs, then made the decision to raise venture capital for the first time and rebuild Athena around AI rather than play defense.

• •Got early access to GPT-4 capabilities through friend on OpenAI red team - 'jaw dropping' results months before public launch
• •Hired PhD in machine learning that summer to get educated on what was coming
• •Decision point: play defense and get disrupted, or play offense and ride the wave - 'offense is way more fun'
• •Previously bootstrapped with personal capital, raised first VC round to fund AI transformation
• •Building OS-level monitoring that watches assistants work to train AI agents - creating unique data moat

Jonathan breaks down the framework for selecting countries to expand into: developing economies with great education systems, English fluency, large youth populations seeking opportunity, and existing BPO infrastructure to hire leadership from.

• •Key criteria: developing countries with great talent, affordable rates vs US, highly educated population, English as primary language
• •Look for 'swelling youth population' with talented people seeking jobs - mission to bring global opportunity
• •Need existing credible businesses in the space to hire experienced leadership (like Shopify effect in Canada)
• •Culture matters: high trust, respectful, hardworking, caring disposition - assistants are 'caretakers'
• •Expanded from The Philippines to Kenya and Guatemala, building physical training centers and local entities

Athena's customer base evolved from Jonathan's personal network to startup founders (100,000 venture-backed startups, still 10x growth potential), then to SMBs (30 million potential customers), and now piloting with Fortune 500 companies that have thousands of internal assistants.

• •Started by emailing friends, naturally led to startup founders since most friends were in tech
• •100,000 venture-backed startups in US, Athena at ~1% penetration, still 10x to go in that segment
• •SMB is next big segment: 30 million businesses, maybe 10 million could use assistants (dental clinics, construction, etc.)
• •Enterprise pilots with companies like AIG and JPMorgan that have 1,000-5,000 internal assistants
• •Enterprise opportunity: bring assistants to directors/managers who don't have them today due to cost

Jonathan reveals his personal setup of 6 specialized EAs: one for work/email/inbox, one for finances/investments, one for home/maintenance, one for kids/travel, plus a chief of staff EA managing the entire team. He shares the journey from Midwest farm background to this level of leverage.

• •6 EAs broken down by domain: work, finances (P&L, angel investments), home (maintenance, booking pros), kids/travel, plus chief of staff
• •Started at White House working next to president's EA - set extremely high bar for what EA partnership could be
• •First hire was on Upwork in The Philippines - encourages people to start there if budget-constrained
• •Began with basics (inbox, calendar, travel) then experimented weekly with new things
• •One EA helped organize weekly dinner parties that led to meeting his wife Catherine and making best friends

Jonathan shares two standout delegation stories: having an EA execute a 6-week project to remove all plastic/toxins from his house after hearing a podcast, and creating a custom 80th birthday book for his dad by DMing hundreds of Facebook friends for stories.

• •Heard Shanna Swan podcast on testosterone/fertility, sent EA to watch, read book, create spreadsheet of 50 recommendations
• •EA worked with house cleaner to find/remove all items, order replacements - 6 week project he'd never do alone
• •Dad's 80th birthday gift: EA going through all Facebook friends, DMing for memorable stories, compiling into book
• •Gift delegation paradox: seems impersonal but enables impossibly meaningful gestures that show deep care
• •Key insight: delegation enables generosity and ambition that wouldn't exist otherwise

Jonathan explains the counterintuitive insight that ambition doesn't drive delegation - delegation creates ambition. As cognitive load lifts, people raise their sights and discover they can accomplish far more than they previously imagined possible.

• •Common misconception: you have unlimited ambition, then hire assistants to execute it
• •Reality: causation is reversed - as you get leverage, cognitive load lifts and ambition expands
• •People's ambition is 'hemmed in by what they think is possible based on tasks on their list'
• •At Thumbtack during intense periods: 'buried, can't possibly take on something new, just trying to figure out today'
• •With leverage: 'woah, I have time to do more things - I could give more generous gifts, start a new business, be more ambitious'

Jonathan breaks down tactical frameworks for effective delegation: the J-curve of upfront investment, voice-based delegation for 3x bandwidth, and the progression from task to project to goal to process-based delegation. He emphasizes the compounding power of long-term EA relationships.

• •The J-curve: literally faster to do it yourself the first time, but not the 100th time - must invest through the dip
• •Voice-based delegation is 3x faster than typing, works while walking/driving/working out, naturally provides more context
• •Delegation progression: specific tasks → projects (bundles of tasks) → goals → process-based (export your algorithm)
• •Process-based example: don't just say 'plan dinner party' - export the full algorithm of who, why, how you think about it
• •Compounding is everything: one EA for over a decade, 'like my little sister now,' seen all ups and downs, in inbox during $100M term sheets and lawsuits

Jonathan identifies the three main limiting beliefs that prevent effective delegation: not believing extreme leverage is possible, feeling guilty about having someone focused on you, and the 'cardinal sin' of thinking it's faster to do it yourself.

• •Limiting belief #1: don't believe it's possible to have 'time abundance' or 100 hours in a day
• •Limiting belief #2: guilt about having someone focused on you - flip it: you're providing a great job to someone who desperately wants it
• •The cardinal sin: 'faster and better to do it myself' - it's TRUE but only the first time, not the 100th
• •Mistake: not investing for long term, trying assistants for a few months then switching - compounding requires commitment
• •Best assistants work for best clients - it's a partnership that requires mutual investment and experimentation

Jonathan shares how EAs are integrated into family life, including the 'Black Diamond' delegation of having a Philippines-based assistant monitor baby monitors at night, reducing nighttime wake-ups by 90%. This idea later inspired the startup Harbor.

• •EAs are 'part of the family, part of the crew' - one assistant came to help set up summer house in mountains
• •Catherine's idea: have Philippines assistant watch baby monitors at night instead of parents
• •90% of wake-ups don't need intervention - kids cry briefly and go back to sleep
• •Assistant calls parents for the 10% that need intervention - 'like an auntie who is part of the family'
• •This delegation inspired Kevin to start Harbor, a company doing this with nurses/doctors involved

Jonathan's ultimate vision: by 2050, everyone will have a human assistant managing thousands of machine assistants. Inspired by a billionaire with a 50-person personal team, where spending 24 hours to save the principal 1 minute is considered worthwhile.

• •Met billionaire investor with personal team of 50, including 8 Princeton-hired executive assistants
• •Team philosophy: if we can spend 24 hours to save principal 1 minute for investments/family/interests, it's worth it
• •2050 vision: not everyone will be billionaire, but everyone will have human assistant powered by Athena
• •That human will manage thousands of machine assistants running errands, checking, remembering everything
• •Result: 'start five new businesses, spend more time with family' - radical expansion of optionality in how to live life