I studied 20K tweets, 26 Medium articles, 18 newsletters, and Andrew’s new book to unearth these lessons
Andrew Wilkinson is one of a kind.
He’s the founder of MetaLab, a web design agency that’s worked with Calvin Klein, Uber, and Slack. He’s also the co-founder of Tiny — a publicly-listed company that buys “wonderful businesses”.
These companies and investments recently made Andrew a billionaire.
And they’ve helped him live out his “definition of success”:
For someone who’s amassed such a fortune, it might be tempting to think he’s unrelatable; that there’s nothing we can learn from him.
But that’s simply not true.
You see, Andrew has been posting online since 2007, and trawling through his old tweets shows that as a 21-year-old, he was posting the same old sh*t that we once did:
“I just farted while listening to headphones in a cafe.”
And three years into building MetaLab — aged 23 — Andrew was drowning in work:
So how did he turn things around?
I’m not here to embarrass Andrew. Far from it. He’s someone I deeply admire, and after studying all of his tweets, Medium articles, newsletters, and his new book, I’ve come to revere his style even more.
I wanted to learn:
- How he lands new clients
- How he builds profitable companies
- Nuggets of wisdom he’s shared since 2007
Let’s go!*
*A quick note about my research methods
This research process — from start to finish — has taken me about 60 days.
(Around 60 hours.)
- I used Twitter’s advanced search feature to look through all of Andrew’s tweets. (I’m calling it Twitter rather than X.) I then read his Medium articles, newsletter posts, and his new book.
- I pulled the most interesting tweets and quotes into Notion.
- Finally, I sorted all these posts in a Google Doc.
Lesson #1: Getting started in business
During school, Andrew teamed up with “three fellow fifteen-year-old nerds” to turn an Apple products review blog called Macteens into a money-printing machine. He sold ads and attended MacWorld conferences. He even interviewed Steve Jobs.
Andrew then studied journalism at college, but he quickly dropped out:
“I started realizing that being a journalist in 2004/2005 was not the life for me. I didn’t want to go work at a newspaper; it felt like learning how to develop photos when digital cameras came out.”
He moved back home.
The problem was he needed to pay his parents $500/month of rent, and he was broke. So he picked up a job as a barista. He enjoyed it for a while, but the excitement began to wear off:
“I started to hate the sound of my alarm. I hated riding the bus to work at 5am. I was bored out of my mind when I had to mop the floors and count the till. And given my meager pay, I barely had any cash left over once I paid rent to my parents.”
For a while, nothing changed.
Andrew read books, mopped, and made coffee.
However, an experience with two customers encouraged him to try something new:
“[…] There were these two guys that would come in every single day. They’d roll in, looking like they just got out of bed […] They were probably five years older than me — so like 24–25 — and they would just sit on their laptops all day, drinking espresso after espresso.
“One day, I asked them, ‘What do you guys do? Don’t you have jobs?’ And they go, ‘Oh, we’re web designers. We just walk into random businesses, ask if they have a website, and then say we’ll make one for $500.’
“So that day, I was like forget this. I don’t want to make the espresso. I want to be drinking the espresso. I want to be these guys. So I bought a book on web design, and a couple of days later, I walked into a place and sold the guy a website.
“Within a couple of weeks, I’d quit my job.”
“[…] I walked into a place and sold the guy a website. Within a couple of weeks, I’d quit my job.”
This isn’t as crazy as it sounds.
Andrew had web design experience because of Macteens, so he knew some basic stuff. “It wasn’t rocket science to me.”
Before long, Andrew was taking on bigger projects, and one client asked him if he could do some JavaScript work.
“I just say yes.
“I don’t know anything about JavaScript, but I’m like I can figure it out, so I frantically try and learn JavaScript — and I can’t.
“So I go to my friend […] who’s in computer science, and I say, ‘Hey, how much would you charge me to do this JavaScript work?’ And he says, ‘I’ll do it for $500.’
“I think I’m going to get negotiated down by this client, so I say to the client ‘It’ll be $1,000.’ And they say, ‘Okay, sounds good.’ In that moment, I was like ‘Oh my god, I just made $500 and I did absolutely no work.’
“That’s a crazy transition going from self-employed person selling your time to being someone who can sell other people’s time.”
Andrew continued down this path.
And over time, he built his web design agency, MetaLab.
(More on this shortly.)
Takeaways
- Follow your curiosity. A chat with two web designers changed Andrew’s life forever.
- Have the balls to ask. The cold approach still works. There’s no harm in trying.
- Just say yes. You can figure stuff out as you go.
Lesson #2: How to build a profitable business
Projects and money came pouring in.
By this point, Andrew had gone all-in on web design:
“[…] I immediately quit the coffee shop and moved out of my parents’ house, which was not the most responsible decision, since I had a new apartment lease and no consistent income.
“But it was meant to be irresponsible.
“I knew the pressure of a lease would light a bonfire under my ass — I had to make it work.”
One of the first things he did to “legitimize” himself was build a website for his agency.
He settled on the name MetaLab:
“[…] I created a page featuring my ‘team’ of professional designers and developers […] Of course, I didn’t actually have a team, so I asked a few of my programmer friends if I could use their pictures on the site. I told them if I actually won a job, I’d hire them for the project.
“Once enough people said yes, I started sending out cold emails, soliciting work for my huge design agency, MetaLab.”
It wasn’t smooth sailing.
We’ve already seen from one of Andrew’s early tweets that he was working all sorts of hours to finish projects.
In this Inc. article, he goes deeper:
“The first couple of years were just disastrous chaos.
“I would wake up every day in a panic, and all of my problems had to be resolved within four to eight hours; this critical person is about to leave, we’re about to lose this client, this person isn’t paying us- and then multiply that by five because pretty soon I was running five or six businesses.
“We didn’t know what we were doing and actually didn’t know how good our business was. We thought it was normal to have 50 or 60 percent profit margins and to double every year because we had never looked at a conventional business.”
“We thought it was normal to have 50 or 60 percent profit margins and to double every year […]”
So what does Andrew look for these days when sizing up business opportunities?
He’s already hinted at the first thing…
#1: High margins
He goes into more detail in this Medium article:
“If a shoe costs $20, Nike doesn’t sell it for $14. They sell it for $400. We have to get back to this world of having pretty reasonable discipline on business models and understanding that many of these gross-margin businesses will never, never break even or become profitable.”
If a business doesn’t have high margins, Andrew throws his hands up.
Take Deliveroo:
In this tweet, Andrew puts it even more simply:
#2: Focus
Like many companies, MetaLab briefly lost its way:
“[…] we made the decision to start selling strategy as a reaction to what other people were doing. We hired some strategists who had worked at big agencies and started adding strategy phases to each new project.
“Unfortunately, none of it was faithful to what we do. The best businesses do one thing well, and at MetaLab, we build stuff.”
Eventually, after a string of pissed-off clients, Andrew brought MetaLab back to what it does best: making stuff.
#3: Low-hanging fruit
This doesn’t mean the big stuff doesn’t matter to customers.
“[…] sometimes you just need a brighter OPEN sign in your window, or to clean the mildew off your awning.
“Try giving yourself an afternoon to go back to the basics and pick some low-hanging fruit. There’s nothing quite like making $50,000 for 5 minutes of work.”
#4: Questions to ask
Before MetaLab kicks off a new project, they ask the following questions:
“What problem is the client trying to solve?
How does their product solve that problem?
Who is the target customer?
How is it different from other products in the same space?
What do they stand for? What are their core values?
What kind of pain points are existing users experiencing?
What are existing users loving about it?
In one sentence, how will we know we’ve been successful?”
Then, there are ten metrics the CEO tracks every week.
Quick side note: Andrew hires CEOs to run his companies. This podcast explains how he does it.
Tracking these metrics helps the CEO to quickly figure out where they’re slipping up and where they need to focus their attention:
“Team Utilization: Do people have enough work?
30/60/90 Day Team Utilization: Do we have enough work coming up?
Client Net Promoter Score: Are our clients happy?
Team Net Promoter Score: Is our team happy?
New Business Pipeline: How much potential new work do we have?
Cash in Bank: How many months can we run without additional cash?
Accounts Receivable: How much do people owe us?
Accounts Payable: How much do we owe other people?
Collection Effectiveness: Are people paying us on time?
Profit Margin: Are we making money and running efficiently?”
Takeaways
- The internet is the ultimate playing field. Anyone who has the skills and puts in the work can make it big. So don’t be afraid to look big.
- If you want to build a profitable business, look for opportunities with high-profit margins. You want to play business on “easier” mode — not hard mode.
- Ask lots of questions and track data. “You can’t manage what you can’t measure” — Peter Drucker, management expert
Lesson #3: How to build awesome products
Some of Andrew and his team’s most successful products have come from scratching their own itches.
Take when MetaLab needed a better invoicing app:
“While we found a ton of web-based invoicing apps, none of them offered a solid estimates feature […]
“I contracted a local Rails developer for a couple of hours a day, and started building a simple app to help us send and track our estimates.
“Over the next eight months, we baked in invoicing and time tracking, and before long, Ballpark was born.”
And what’s the secret to building a great product that everyone talks about, like Slack?
It’s the stuff you might not think about.
The small details; the feeling a great product gives you.
“Like a well-built home, great software focuses on giving its users hundreds of small, satisfying interactions.
“A great transition in a mobile app gives us the same feeling we get from using a well-made door handle on a solid oak door. You may not be able to put your finger on it, but man, does the house ever feel well built.
“Slack is really fun to use. It feels like a well-built house.”
Takeaways
- Scratch your own itches. If you have a genuine business need for something, other people might too.
- Focus on the details. They make all the difference.
- Hire outside help if you need it. If you want to build an app but don’t know how to code, you’ve got two options: 1) Learn how to code with the help of a teacher, or 2) Hire someone who can.
#4: How to build a team
When Andrew started MetaLab in 2006, the idea of handing anything off seemed “insane”.
But hiring people is the “best business decision” he’s ever made.
“It’s freed me up to build incredible products, let me focus on the stuff that I love, and given me the opportunity to work on projects that would have been impossible without the help of a great team.”
So how do you build a brilliant team?
Of course, you have to hire well, but more importantly, you have to “let people put out their own fires”:
“When I started hiring contractors to help with my workload, I made a critical mistake: If their first mockup wasn’t great, or a client got unhappy, I’d immediately step in and put out the fire.
“You need to let things blow up in people’s faces. Let them make mistakes. If one of your employees misses a deadline, force them to talk to the client directly.
“If you’re the middle-man jumping into the fray whenever anything goes amiss, you’ll be stuck micro-managing everyone. Step back and let people clean up their own messes and they’ll make the necessary course corrections on their own.
“Your team will respect you for it, and you’ll save yourself tons of headaches.”
When Andrew first started MetaLab, he admits that he “sucked at hiring people.” He’d hire someone because he liked them, not because they had the right skills or experience.
So for the first couple of years Andrew had employees, MetaLab’s work actually got worse instead of better.
“I was terrified that I was going to ruin the company, and I fantasized about a simpler time when it was just me doing everything myself.”
Over time, he figured it out.
He got better at hiring people, he built processes, and he learned how to train people properly.
Crucially, he hired people to do the stuff he hated.
“I felt guilty about it. It felt like cheating. But over the years, I’ve realized that my so-called laziness is actually a huge advantage.
“Entrepreneurship is really just a fancy word for delegation. It’s a continuous process of removing yourself from the equation step-by-step and empowering your team to do the things that they do best.”
Want to know one of Andrew’s best sources for finding exceptional talent?
Posting on Twitter.
He’s been sourcing talent from his network since 2009:
Here’s a more recent example from 2019.
Notice how he stokes engagement by asking his network to recommend people:
Finally, how do you know if someone’s going to be a good fit at your company?
Andrew gives two great pieces of advice.
The first is his “litmus test”:
The second is this interview question:
Takeaways
- Hire people to do the stuff you hate. You might enjoy my outsourcing course if you’re not sure how to do this.
- Let people make mistakes. You’ll be forever micro-managing if you don’t.
- Lean on your network. If you need someone to fill a position, ask people you know. They might be able to help.
#5: How to land new clients & make connections
Andrew encourages entrepreneurs to start where they want to end up.
For example,
“[…] if you want to be a big design agency, start building on that idea from day one.
“Too many designers convince themselves that they need to work locally, bill out at a low hourly rate, and sell a range of services (“We do catalogues, websites, wedding photography, copywriting and more!”)
“This is a bullet train to nowhere. Do exactly the type of work that you want to be doing from day one.”
To this end, Andrew says you should design your website for your ideal client.
What’s important to them?
What do they want to see?
“Remember, potential clients have no prior knowledge of who you are, where you live, or where you’ve worked. And frankly, it doesn’t matter. You need to provide 3 key pieces of information:
“What you do: One to two sentences, maximum. What you do. Who you do it for.
“Your work: Only show off your best stuff. If you only have three good pieces, show three pieces.
“Contact us: A way to get in touch.”
But what if you can’t find paying clients?
Andrew says you should do projects for free — your own creations or otherwise — and “ruthlessly publicize them”:
“See a Fortune 500 company in need of a facelift? A celebrity with an ugly blog? There’s your chance to shine.
“Pro bono jobs may not put money in the bank, but they’ll look great in your portfolio, get your name out there, and become an invaluable source of income in the future.
“More importantly, they’ll prove that you’re capable of doing great work — even if you weren’t paid to do it (and most clients won’t know that anyway).”
So how else does Andrew make connections for his businesses?
He talks about other businesses/people on Twitter.
Take this tweet from 2009 (Andrew was around 23 years old at the time):
Then there’s this tweet which celebrates the success of another entrepreneur:
Andrew even admits he’s using this strategy to get on people’s radar.
Here’s how he thinks about it:
It seems Elon himself might be next in his scope:
Andrew also used to attend lots of conferences.
In this newsletter, he explains that when his business was barely scraping by, he spent “almost $20,000 to attend the TED conference”.
He knows it sounds “insanely irresponsible”, but Andrew claims it was one of his “best investments of all time”.
Why?
“[…] just being in that room would unlock my career.
“After years of attending, when people needed an app or website designed, they went ‘Oh! What about Andrew, that guy from TED!’”
“I eventually landed a huge amount of work. MetaLab even ended up building TED Connect, TED’s own app for conference attendees. Not by selling or schmoozing. Just by making friends — many of whom I’m still close with today.”
Takeaways
- Build your portfolio. If this means doing work pro bono (i.e. for free), it’s often worth doing it — at least if you’re new. You can use testimonials and previous work in your pitches.
- “Ruthlessly publicize” your work. My client outreach method can help you with this. (See step #3 in this article.)
- Put yourself in places where lady luck can land on you. Conferences can be great for this.
#6: How to build a following on Twitter
Andrew has been posting on Twitter for a very long time.
And he posts a lot.
Lots of his early posts were about movies and podcasts. Take this one from 2007 (Andrew was ~21 years old):
It wasn’t until 2013 that some of Andrew’s posts started to get more engagement and his following took off:
It has to be said he’s a funny guy, too!
Here are two of my favourite tweets. One is about posts on Instagram. The other is about ways to get in touch with Andrew:
Then come the life lessons.
Obviously, these posts have come later in Andrew’s career, now that he’s successful.
Here’s one about unethical people:
Here’s another about spending time with kids:
He also asks interesting questions to his followers.
More engagement = more visibility
Take this one about regrets:
Sometimes, he’ll post interesting quotes.
Here’s one of my favourites from Kevin Kelly:
And although he’ll sometimes post things that seem obvious, they hit harder somehow.
Billionaire status can do that:
Sometimes, Andrew will post things that deliberately stir the pot.
Take this post about Web3:
He’s also not afraid to call out companies.
Notice how he takes a dig at Facebook in this 2019 tweet:
But he doesn’t always get it right.
It seems he underestimated Instagram back in 2010:
And in more recent times, Andrew has honed his storytelling skills.
Here’s a great example. It’s basically a post about Andrew stepping down as the CEO of Tiny.
Notice how his post hooks you in:
Takeaways
- Let your personality shine. There’s a good chance that if you find something interesting, other people will too. Nothing is off-limits.
- Andrew’s been posting on Twitter since 2007. And his posts only really started taking off eight years later.
- Life lessons carry more weight when you’ve actually achieved something. People listen to “somebodies” — not “nobodies”. Do cool sh*t and then talk about it.
#7: Do stuff your own way
Andrew has been steadfast in his business-building values.
One of these is he doesn’t subscribe to the whole “hustle at all costs” culture — at least not for his teams.
Here’s a passage he wrote in 2014 about MetaLab:
“At MetaLab, everyone is responsible for their own schedule. No bunk beds in the office or ramen-fueled overnight programming melees. We usually clock between four and six hours a day, and most of us don’t even get to the office before noon. We believe in working smart, not hard, and having lives outside the office.”
Andrew also doesn’t like taking money from investors.
Here’s how he described venture money back in 2015:
“The siren call for many entrepreneurs isn’t money, it’s freedom. The freedom to chart your own path, the freedom to build what you want with the people you love.
“Taking money, building a board, and raising rounds takes away that freedom little by little.
“When you take venture money, you work for your investors, not yourself. You’re committing to grow fast to dominate your market and get your investors their cash back in the form of an exit or going public as soon as possible.”
Finally, despite all his financial success, Andrew’s goal with work is surprisingly simple.
Here’s how he talked about it in 2017:
“Last year, my business partner Chris and I sat down to think about what we wanted to achieve at Tiny. We thought up all sorts of lofty goals, but when we really got down to it, our true goal was actually pretty simple.
“We wanted to do something many successful business people seem to struggle with: we wanted to actually enjoy our time at work.”
Takeaways:
- You don’t have to stay in hustle mode forever. Andrew hustled for years. It got him to where he is. However, he now prioritises sleep, relationships, and other healthy habits.
- Resist taking on VC money. (Honestly, this isn’t something most creators have to worry about.)
- Think about your “anti-goals”. It’s often easier to figure out what you don’t want than what you do want. Start with this and work backwards.
Takeaways
It’s been a joy studying Andrew over the last two months.
If I had to boil down everything I’ve learned about this successful entrepreneur, it would be this:
- Build businesses with high margins and scale. This could be digital products, online courses, memberships — whatever. As creators, we’re blessed that online businesses have scale baked in.
- Put in the time to build your skills and build trust with your audience. Andrew has been building in public and consistently posting on Twitter since 2007. That’s 17 years. Take a moment to let that sink in.
- Share thought-provoking, emotive content. If you share the same pithy one-liners as everybody else, you’ll blend in. Be more than background noise. Stand out.
- If something makes you laugh, share it! Other people will probably find it funny, too — and it’ll bring you closer to them.
- Celebrate people who are doing cool sh*t! Karma will pay you back.