Lesson #1 - You need your “bread and butter”

The biggest mistake I’ve seen (and made myself in the past) was hiring an assistant, and then every day feeling stressed that I need to “give them something to do” otherwise they’re sitting idle - like a taxi driver waiting outside with the meter running. 

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That’s why it was critical to find my “bread and butter” (B&B).

The ideal B&B is something that: 

• Repeats daily
• Does not require creativity or specialized skills
• Doesn’t require your input (so you can be offline and it still gets done)

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For a lot of CEO types, this is calendar/scheduling. For me, I try not to have too many meetings, so my bread & butter was email.

Before my email system sucked. 

• Either I’d spend 2-3 hours a day just playing email catchup
• Or I was inconsistent with email, and then the most important stuff would fall through the cracks

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So what we did was set up an email triage system.

• Assistant screens every email and separates things into: 
• Action items 
• Needs reply
• Read later
• If you’re interested (random stuff that might be of interest)
• Other

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For many emails, she would draft a reply, and leave it there. I can just hit send, or make a quick edit (it’s crazy how much easier things are when you’re editing vs. drafting a blank page).

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I spend 30 minutes on email twice a day. Once at noon, and once in the evening after kids go to bed. It’s easy, and I’m not missing out on important info or opportunities. 

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This one task alone saves me 2+ hours per day (10 hours a week). If she did nothing else, this would already be worth it for me. 

Lesson #2 - Remember the goal

The goal of having a personal assistant is so that you can spend more time in your zone of genius. 

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I’ll say that again. 

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The goal is to have you spend more time in your zone of genius. 

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For me, that’s creating content or investing. My podcast gets nearly 30M downloads per year. And we invest ~$10M per year into startups. Every work-hour I spend not doing content or investing is an hour poorly spent. 

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Outside of work, I want to spend time with my family.  When my assistant saves me 2-4 hours a week on errands, that’s time I can spend with them at the park, or taking them out for a sneaky pre-dinner ice cream run. 

Lesson #3 - It's cheaper than you think. It's only $10,000 a year.

There are a bunch of companies to help you find virtual personal assistants. 

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Most of them are charging you way too much.

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Most of them try to charge you a “monthly fee”, like $3,000 per month usually. 

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That'd be $36,000.

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That's not bad, but there's a problem: the assistant only gets $800-$1,000 of the $3,000 (25-30%).

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That means you’re being marked up 3X+ every single month. 

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That’s why I started using Shepherd. They do the exact same thing, but on a headhunter model.

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So they only charge you ONE time for the placement, and then on an ongoing monthly basis, you just pay your assistant directly the actual cost.*

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It’s a way better model. And it means you should only be spending $10,000 a year for your assistant.

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*Disclosure: I’ve made several hires through them, and liked it so much I emailed Marshall the owner and ended up investing in the company.

Lesson #4 - Security is important

When I first decided to hire an assistant, all I could think about was the worst case scenario.

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That scenario: I give access to my email, my bank account, and all my socials to someone I’ve never met, on the other side of the world, and they steal everything.

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While I think that’s like waking up in the middle of the night worried that I forgot to turn in my homework, it still scared the shit out of me.

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So I set up a firewall to prevent this. I call it "The Great Wall of Shaan".

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Basically, she has full access to communication, but not my finances. It only takes 3-4 steps to put this into practice.

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For example, for expenses, I created a virtual card on Ramp that has strict spending limits and notifies my phone for every purchase. 

And for banking, I created a separate email for financial stuff, so any password resets can only be done through a separate inbox she doesn’t have access to.

I put all the security steps in the system you can grab right now.

Lesson #6 - It’s actually possible to be the man I've always wanted to be 

The most thoughtful person I’ve ever seen is my buddy, Ramon. He’s so thoughtful, it almost pisses me off. Like dude, why do you have to be so nice, now I feel guilty I’m not nice enough back! 

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Ramon will remember your kids birthdays and send them gifts. If he hears you’re learning taekwondo for a hobby, he’ll swing by the library and pick up “Taekwondo for dummies” and drop it off at your house.

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He’s the kinda guy who remembers that your wife is vegan, and buys a separate vegan cupcake so she can have that during someone else’s birthday party. 

Ideally, I would be more like Ramon. But let’s be real. I’m not that guy. So the next best thing was telling my assistant that I want to be like Ramon. So she made a calendar of everyone’s birthdays and work anniversaries, and I gave her a budget to buy gifts or come up with ideas to make them feel special. 

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In the past month alone, Drea has:

• Bought my mom & mother-in-law a great mother’s day massage off Groupon
• Planned a whole trip to Disneyland for me and my family
• Sent every new employee at my company a welcome package  
• Organized a monthly dinner with other founders who live near me that I want to keep in touch with

Lesson #7 - Do the Math

Let’s say you get paid $100,000 per year running your business.

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Let’s assume you work 40 hours a week, so every hour is worth $50.

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An assistant in the Philippines will cost you about $800/mo.

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All you have to save is 16 hours per month (or 4 hours per week) to be ROI positive. Here’s the number of “hours saved” you need to break even on your investment. 

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So just purely from an “hourly rate” POV, most CEOs/business owners only need to save 4-8 hours a month to make this worth it.

And then you re-invest those hours growing your business, which grows your annual income. AND you spend more time doing stuff you love, vs. stuff you have to do. 

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Win-win-win.