How Andrew Runs A $180M/Year Business by delegating...

1. How to make yourself more ‘lucky’ in business.

One of my favourite maxims is “Relationships run the world”. This is as true in life as it is in business.

Think about what happened over the past few days, I guarantee that the high ‘ups’ you experienced involve someone else.

Business is no different.

You cannot create a hundred million dollar company doing everything yourself. You need to assemble an army.

Most people view luck as something that they cannot influence. “It just happens”.

But that’s wrong. Andrew figured this out. You can become ‘more lucky’ through designing systems to increase your luck surface area. 

So how can you create systems that increase the chance of luck happening to you?

The first step is to increase your luck surface area.

• Create a friendship funnel

• Do interesting work (and talk/write about it)

• Connect others and provide value to your network 

One great way Andrew does this is by building funnels for people to ‘buy’ into him.

He has his Twitter, newsletter, his book, podcasts that he goes on, and his own podcast.

This all gives potential opportunities for people to:

• Get to know Andrew,

• learn what he's about, and

• Decide if they want to work with him or sell their company to him. 

The essence of all of this is that one of the biggest (and most mispriced) opportunities for your business is focusing on relationships. 

By doing business in a world-class way with world-class people, Andrew's reputation spread, when Andrew flew from Canada to New Zealand for an unrelated to work conference, Andrew tweeted to his audience asking who follows him that lives in Auckland. 

Because Andrew had spent years building a reputation online and putting himself out there, Matt Buchanan, founder of Letterbox reached out. They had coffee. 

As they were speaking, Matt mentioned that at the time Letterbox had over 12 million users – the number caught Andrew totally off guard. Matt did not seem excited as he had been running the business for 10+ years and was telling Andrew about his plans to do something else.

Maybe I could buy the business Andrew thought, so he said

“What’s your craziest number?” “What do you want to happen?” 

Within a few days, whilst Andrew was about to fly away at the airport they negotiated and signed the deal. 

Andrew told me:

That is the formula. That is the hack, putting yourself out there. You cannot connect the dots or people looking forwards. 

So how do you create systems to do this for yourself?

1. Have a founder-newsletter 

2. Have a weekly founder-forum

3. Host (ideally) annual conferences.

Firstly, Andrew has a newsletter where weekly he sends an email to over 40,000 people. That’s 40,000+ potential investments, business opportunities and friends.

Tyler Denk, Founder of beehiiv has a weekly newsletter he sends to over 80,000+ people detailing how he’s building his company. He’s raised over $50M within weeks because of him writing that newsletter.

By having a founder-presence online, you’re able to increase your luck surface area.

Secondly, Andrew is part of several founder forums and groups. If you’re able to join these groups, or host one yourself where monthly you have sessions together. Do it.

You’ll start to learn a ton, even from people you wouldn’t expect to learn from. Andrew has been in a group with someone who runs a popsicle company, a puzzle company and a map-software company. And has learned from each one of them – he's been in groups like this for over 20 years.

Thirdly, now granted this is a bit harder to do, is run conferences or events. The AI note-taking company granola does this very well – they run weekly events at their office. Hosting talks with other founders, other PM’s, designers, engineers etc.

This makes their office the go-to hot spot for early stage tech employees. If you facilitate genuine relationships, the value is attributed to you, increasing your surface area of luck again.

2. How to run a $180M business for 20 years without being miserable

Andrew made millions in his early 20s. The dream, right? Except he felt empty. He had reached the top only to realise that the mountain he was on was lonely and not at all what he had imagined.

If you play games you don’t care about. You win prizes you don’t care about either.

Before starting a business, before joining a company, before taking on a new role or venture – ask yourself; “If taken to the extreme, do I like how this looks?”. It sounds simple but it’s really important. Then map this with what you are exceptional at, and what your anti-goals are.

In 2013, when Andrew was running 5 companies and making millions but “hated his life”.  He tried desperately to become a better manager.

That’s a hard realization, but uber-important. Because once Andrew had a good understanding of the problems he enjoys solving, the responsibilities and burdens he enjoys carrying. He could better organise his work around them.

Soon after this, Andrew started setting “anti-goals” for his life and work. 

I don’t want to miss dinners with my family.

I don't want any meetings I dread having. to look forward to every meeting I have.

I don’t want to do business with anyone that gives me the creeps.

I don’t want to be forced to travel to client meetings.

Guess what? Those are solvable problems. When Andrew hired a sales-rep at MetaLab, he looked for someone who loved travelling to clients for work (an anti-goal of his). Sometimes you just need to write out your anti-goals and structurally try to eliminate them. 

“All I want to know is where I’m going to die so I don’t go there”

- Charlie Munger

3.  How to promote and hire the right person at your company

Since starting the Tiny holding company, the company has;

• 35 Majority-owned businesses 

• Incubated 11 businesses,

• Made over 90 minority investments 

• Has over 900 employees.

The motto of Tiny becoming the “buyer they wish they could have sold to” means Tiny has to be very careful when acquiring companies.

One of the most important things in business is setting the incentives and making sure you hire the right people. This is even more so true for the CEO of a company. 

In this short section we’ll learn how Andrew and Tiny think about hiring CEO’s and hiring.

Andrew believes the most important thing is knowing what success looks like in the role. Let’s say you're hiring someone for a real-estate project, you may not understand all of the engineering but over time you start to understand what the right type of engineer looks like and how to tell if they’re competent. 

That’s the skill set Andrew says he has developed that is most impactful in business. 

So what are some frameworks you can steal to identify the folks who would be the right people in the role you want to fill? Here are 3 frameworks Andrew uses:

The Baby Sitter Question

Would you let them babysit your kids? If not, and you get bad feelings that this person is not-trustworthy. Immediately discard that candidate – no matter what.

Experience running the same business

Has this person run a similar business (or the same) at 2-3x the scale? Importantly no bigger than that, since large company people struggle running smaller companies and vice-versa.

Andrew likes to have someone come in and look at the role and think immediately “I know exactly how to grow this”.

Strategic Alignment

Andrew wants to be nodding along when asking the candidate what the strategy is. He says;

This isn’t a bullet-proof playbook, but hopefully these frameworks are useful for when you’re considering the next hire you need to make.

I built a Chrome extension that auto-likes tweets from VCs. It landed me 14 intro calls and 3 angel checks. One of them called me a “product genius.” I stole the whole idea from a Hacker News comment.
- anonymous