World Class Delegation (from a Unicorn Founder)

How Jonathan Swanson is teaching founders to become time-billionaires

Would Elon Musk rather have another billion dollars or more time in his day?

The most successful founders don’t buy cars or clothes, they buy time. When you’re a founder you know that how you spend your time is your most valuable asset.

Most founders I talk to feel a sense of time-scarcity — there’s so much to do to build their startup and not enough time in the day to do it.

But Jonathan Swanson sees a different path. By mastering delegation, he’s been able to build and scale a unicorn (Thumbtack) and now his new startup, Athena, takes what he learned and helps anyone build up massive leverage to scale their time and become a time billionaire.

Once someone masters delegation they begin to think bigger — maybe they start a second business, a fund, or non-profit. Maybe they’re able to be more thoughtful with friends or family members. Overall, it unlocks a richer and fuller life that widens your ambition.

So I sat down with Jonathan this week to find out:

  • What’s the biggest mistake delegators make?

  • How can you become a better delegator?

  • What blocks most people from reaching “delegation nirvana”?

  • What are good examples of effective delegation?

PS: I also convinced him to offer a $1,500 discount on an assistant to readers.

Becoming a World-Class Delegator

The Biggest Mistake Delegators Make

The biggest mistake delegators make isn’t delegating the wrong things — it’s not delegating enough. Jonathan says the best delegators end up delegating more than 10x the amount of work that everyone else does.

More tedious tasks, more complex tasks, more consistently, and more often — it’s the sheer volume that makes the difference.

The best way to partner with your assistant is to simply give them a lot of projects and help them iterate towards delivering the right outputs.

In my experience, most founders underestimate what can be delegated. I’m guilty of this myself. But Jonathan made clear that the only way to get massive leverage is to experiment more and more with your assistant. Not every delegation will work but the more experiments you run the more success you will have.

That’s something he didn’t even think would be possible 2 years ago but now sees every day as more founders go through their delegation training program.

The Levels of Delegation

An easy way to become a better delegator is to identify what will unlock more leverage for yourself. Jonathan broke it down into 5 levels, with one more that he’s building at Athena.

#1 — Novice: Delegation by Task

Jonathan has seen thousands of delegators start their journey and, without help from Athena’s delegation training, this is where most people end up getting stuck.

They request their assistant to execute individual tasks, over and over. They delegate things as they come up, sort of like a stream of consciousness.

Example: “Find flowers for my friend’s birthday.”

#2 — Intermediate: Delegation by Project

This is where you start to give a bit more responsibility to your assistant as projects are larger and more complex than individual tasks.

There are three types of projects you can delegate:

  1. One-off → Similar to the Novice level but with more pieces. Ex: “Plan my friend’s birthday.”

  2. Recurring → A project that happens on a set interval. Ex: “Prepare a report of my personal finances on the 1st of each month.”

  3. Trigger-based → Projects that can happen on any interval, and are triggered by a specific thing. Ex: “Every time I fly to a new city [aka the trigger] plan and schedule an entrepreneur dinner.”

#3 — Advanced: Delegation by Process

What you have in your head as the expected outcome of assigning a project to an assistant is likely different than what they will execute. You simply have more context on what you want than you’ll have given them.

At the third stage you start to look at yourself and your personal preferences as a set of algorithms, and your goal is to describe and offload those algorithms to your assistant.

Rather than just asking your assistant to plan an entrepreneur dinner when you fly to a new city, you create an algorithm for them that constrains the problem they’re solving for.

For example, maybe the dinner must meet the following criteria:

  • 8-10 people (right size)

  • Attendees must have a certain number of employees or revenue, or be in a certain industry

This is a simple example, and the chances are you’ll need to make adjustments to the algorithm the first few times you have your assistant run it, but then they’ll be able to do it successfully forever.

#4 — Expert: Delegation by Goal

Most delegators never give their assistants context on their goals, they just assign them tasks or projects.

But to truly become an expert delegator and unlock time abundance you need to be more transparent and open up more to your assistant.

The two main benefits of this are that your assistant can:

  1. Deliver results and prioritize with your larger goals in mind

  2. Flag opportunities for new projects that align with your goals

Once you get this right your assistant goes from just executing to being able to start anticipating your needs. You no longer need to explain as many details of every project you assign them ahead of time.

#5 — Mastery: Clairvoyant Delegation

Jonathan says this is the nirvana of delegation, and that mediocre delegators think it doesn’t even exist.

At this stage you’re in perfect alignment with your assistant or, more likely, team of assistants — Jonathan has five spread across different areas of his work and non-work life.

You’re working only on tasks you’re uniquely suited to do, and your assistant(s) handle the rest. You trust them as much as a family member and they can discover and execute tasks without even needing to clear them with you first. Often the first time you hear about a project is when it’s been completed.

Reaching this level takes consistent work with an assistant over years, and Athena’s goal is to get delegators here faster than otherwise possible.

#6 — Automated Delegation

In order to delegate something today you need to describe the project, or your goals, to your assistants. There are different ways to do this:

  • Text/typing → Slowest

  • Voice → Fastest/easiest

  • Loom videos → Adds the most context

But what if AI could automatically identify tasks that were able to be delegated to your assistant, or automated by an AI assistant?

You’d go from needing to consciously delegate to letting your delegation run on autopilot, even if you’re not at the mastery level with a whole team of human assistants.

Athena’s vision is for each of your human-assistants to manage, maintain, and interact with many different digital assistants that observe what you prioritize and flag tasks that can be delegated. Your human assistant(s) will be empowered to do higher-level work, as well, with your digital assistants automating the more tedious tasks.

This will take time to develop but will ultimately unlock an entire new level of leverage — and makes it worth thinking of Athena in a different class than other companies in their space.

What Stops People from Delegating?

So… why doesn’t everyone reach the level of clairvoyant delegation? I asked Jonathan what the biggest blockers for people are along the journey.

#1 — Not Trading Speed for Leverage

The cardinal sin of delegation is thinking you can do it better or faster yourself.

Often you’re right — you can do it better or faster yourself this time — but you’re missing out on an opportunity to trade that small bit of initial time or quality for compounding leverage you can hold onto forever.

Focusing on your own ability to move the fastest or in the best way is the surest way to never get leverage.

#2 — Not Going All In With Your Assistant

The best assistants want to work full-time for one client that they can learn the ins and outs of working with over a long time horizon.

Changing your assistant frequently won’t allow for those compounding gains, and only working with a part-time assistant means the other person they’re working with could take them away from you at any time.

Put yourself in a position to build compounding leverage, not one where you need to start from scratch repeatedly.

#3 — Not Giving Enough Access

It’s scary to give access to your calendar, inbox, bank account, passwords, etc to an assistant you’ve never met in person.

But the more access you give, the more leverage you get.

This is an area where Athena adds a lot of value — they screen and vet the assistants they match you with so you don’t need to.

#4 — Feeling Guilty

For first-time delegators in particular, you may feel guilty giving long and tedious tasks or projects to your assistant.

But you shouldn’t.

Your assistant’s mission is to give you more leverage and take care of your needs. They’re excited to help because they’re excited for the role they have on your team.

That’s easy to forget but don’t let yourself.

#5 — Not Having Enough Ambition

Jonathan says that when people tell him they don’t know what to delegate it’s often because they aren’t thinking big or creatively enough with what to delegate.

The best delegators are often the most dissatisfied with the amount of leverage they have. They’ve trained themselves to always look for more — just like you train yourself for any habit, like going to the gym.

Delegation Examples

I spent too much time going through Athena’s free library of delegation playbooks, but Jonathan also generously offered up a whole list of his own examples for what founders can delegate. Here are some of my favorites:

  • Automating home management → Jonathan lived as nomad for a few years and loved living in hotels, so when he and his wife bought a house they wanted house to be run like a hotel. His assistant orders food, books services to maintain the house, keeps the fridge stocked, and co-ordinates cleanings.

  • Making new friends → Jonathan’s social circle outside of Thumbtack was limited while he was scaling the company so he asked his assistant to plan dinners at his apartment with entrepreneurs he didn’t know. He says he made most of his best friends this way.

  • Being a better boss → His assistant created flashcards with all 500 employees’ names from Thumbtack that he then memorized so he always knew someone’s name on their first day. Also his assistant would send thank you notes + celebratory notes to the half-dozen or so people every day who were having birthdays or work anniversaries.

  • Helping with hiring → Jonathan’s assistant has helped him recruit everything from a nanny to a board member.

  • Managing finances → Track expenses and investments and organize it into a monthly P&L Google Sheet.

  • Giving amazing gifts to family → For his mother-in-law’s 75th birthday, Jonathan’s assistant helped him collect 365 memories/messages from her friends and sent her one every day for a year.

There’s a lot more examples as well — the bottom line is that founders should try to build up leverage wherever possible. As it compounds it lets you accelerate your startup much faster than otherwise possible.

And with the tools Athena is building, I hope we’ll see many more people become delegation masters in the next few years.

(And don’t forget to snag the $1,500 discount on your assistant that I convinced Jonathan to offer to readers.)

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