Andrew Wilkinson
@awilkinson
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Co-founder of Tiny w/ @_Sparling_ . We own @Dribbble , @Letterboxd , @AeroPress , and other wonderful companies. Funding science and journalism at Tiny Foundation.
Victoria, Canada
Joined July 2006
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I've started a newsletter.
It's really simple:
Once a week, I'll send you a few recommendations.
Things I'm thinking about. Products I love. Articles I'm reading. Twitter accounts to follow.
That's it.
If you're interested in getting it, click here: …
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Someone has literally recreated Photoshop feature for feature, for free, in the browser 🤯
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Elon Musk fired 6,500 employees at Twitter.
A little birdie told me it's down to:
- 2 designers
- 6 iOS developers
- 20 web developers
- Around 1,400 sales and operations people
How is it possible that we are still using this website?
Two words:
Parkinson's Law.
Have you…
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This is a story about how I lost $10,000,000 by doing something stupid.
Ten. Million. Dollars.
Literally up in smoke. Money bonfire.
That’s enough to retire with $250,000+ in annual income.
Here’s what happened…
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"Here's the number I used to win the lottery"
–Entrepreneurs giving advice
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What
@elonmusk
just did with Twitter ads is brilliant.
He just made every major creator on the platform a financial beneficiary.
When Twitter sells ads, the community gets a slice.
Alignment of incentives.
Same thing with paid subscriptions.
When creators get paid, Twitter…
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Shit on
@elonmusk
all you want, but he has The Now Habit.
As soon as he has an idea, he takes action towards making it happen.
This is inherently chaotic, but for better or worse, it's likely a big part of why he's so successful.
Rapid action, iteration, and experimentation.
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How to win at business:
Hire smart people.
Pay them well.
Leave them alone.
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I read a book that blew my mind a little and I can’t stop telling people about it.
It explains why so many people dedicate their lives to achieving things that make them miserable.
This might sound crazy, but an unseen force is pushing you towards empty and unfulfilling goals…
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On Aug 1, I woke up and didn’t want to get out of bed.
I felt…blank. Hollowed out. I’d felt this way for months.
I couldn’t enjoy anything.
I didn’t care about work.
I didn’t want to talk to anyone.
I wasn’t necessarily depressed. Objectively life was amazing...
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A friend said something crazy to me the other day:
"You have 18 summers to enjoy with your kids. That's it."
By the time your kids turn 18, you have spent 70%+ of the total time you will spend with them. After that, it's a wild card (they are busy, you are old).
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Working 8 hrs a day in a normal company with $100k a year salary = $48/hr
Working 16 hrs a day at Goldman/McKinsey with $200k a year salary = $48/hr
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I started my company 16 years, 3 months, and 5 days ago.
Today, it went public.
But let's rewind for a second...
5,939 days ago, I was a barista at a small cafe called
@2percentJazz2
, in Victoria, Canada.
I made $6.50 an hour.
Two guys, Chris and Jeff, started coming into…
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Most successful people are just a walking anxiety disorder harnessed for productivity.
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10 years ago, I was working 12 hour days running a single business.
10 years later, my business partner Chris and I live the life of retirees.
Yet:
We now own 20 majority owned businesses.
With over 400 employees.
And 80 minority investments.
Plus a bakery and hotel.
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The year is 1996 and you own a newspaper. The internet just came out, but you don’t really get it.
Which businesses are similar in 2023 with GPT3 + AI looming?
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It's strange, the more money I make, the nicer people are to me.
Especially investment bankers, realtors, and stock brokers.
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Our brains are designed for:
- 1 to 3 tasks per day 🔥💧🦌
- A social group of less than 50 👨👩👧👦
- Most time spent silent in nature doing a task 🌲🌲🌲
- No awareness of anything happening outside of 5 square kilometers 🧭
No wonder we’re all miserable.
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As a CEO, your job is actually to do nothing.
CEOs who actually perform duties within their companies are failing.
Your job is to set strategy and culture, delegate, and incentivize.
Same goes for executives. You are just more focused mini-CEOs, who report up.
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Things that don’t matter right now:
- Clothes
- Shoes
- Watches
- Jewelry
- Cars
What’s the new status symbol during a lockdown?
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Earlier this year, I had a productivity breakthrough...
I used to spend $25k-$100k building an app over 3-6 months. It was frustrating, expensive, and slow.
Then I started using NoCode tools like Webflow, Bubble, Zapier and AirTable...
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“You don’t have to attend every argument you’re invited to”
–Charlie Munger
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Best ways to get in touch with me:
1. Text
2. Email
3. Twitter DM
4. Write a note on my car windshield in dust
5. Message in a bottle
6. Morse code using laser pointer
...
105. LinkedIn message
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“If I can be optimistic at 99, almost dead, surely the rest of you can handle a little inflation.”
–Charlie Munger
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Remember when people used to fly for 5 hours, stay in a hotel overnight, and spend $2,000 for a 1 hour meeting instead of doing a Zoom?
It truly wasn’t a better time.
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So many people think they want to retire...
But freedom is better:
The freedom to say no.
To cancel appointments.
To ignore your inbox.
To take random days off.
To put your phone away.
To wrap your day at 2pm.
To go for walks.
To play with your kids.
The ultimate.
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The best way to learn is to walk around sticking forks in electrical sockets and adjusting accordingly.
This one hurt. A lot.
I'll try to keep sharing my screw ups as they happen.
Follow me at
@awilkinson
.
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At Tiny, I've hired CEOs for 60+ companies and interviewed hundreds of others.
After over a decade of trial and error (and I mean BIG errors), here’s our hiring process:
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The best investors do nothing 99% of the time.
They sit on their hands, sometimes for years, preparing.
Reading, thinking, analyzing.
Then, when the right opportunity comes along, they strike with conviction.
It sounds easy. It’s not.
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I turned 35 today 🎈
40-50 year olds of Twitter:
What are the things you regret not doing more at my age?
What are the things you cherish most in retrospect and are glad you did at my age?
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I was sad to learn that Charlie Munger died today at age 99.
What a life.
He would likely roll his eyes and argue that none of us should be too surprised, based on the actuarial tables, but we’ve lost one of the 20th century’s greatest investors and businessmen.
Chris and I…
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"Here's the numbers I used to win the lottery" –Entrepreneurs giving advice
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According to Bloomberg, Adam Neumann took $800-$1B off the table at WeWork.
The total market cap of WeWork is now $395M.
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There are four types of entrepreneurs:
1. Innovators - the person who invents the burrito 🌯
2. Remixers - the person who creates Chipotle 🌶
3. Scalers - the person who scales it to 100+ locations 🏢
4. Optimizers - the person who dials in margins and process 🔧
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8. If you’re competing on features, it never stops and is an ever-increasing line item.
9. Good product with great marketing beats amazing product with no marketing.
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Every day, for over a year, the only thing I listened to on my drive to work was this speech.
It changed my life.
I still use its lessons every single day.
We made an abridged video version of it, to help spread the word:
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"A man always has two reasons for doing anything: a good reason and the real reason."
–J. P. Morgan
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In this instance, I learned a lot.
The key takeaways are:
1. If you are in a competitive VC-funded space, it’s foolish to compete without raising money. Don't bring a knife to a gun fight.
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How to run a profitable company:
Revenue
- Expenses
———————
= Profit
IMPORTANT NOTE: Make sure expenses are lower than revenue.
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Someone should build a GPT3 powered podcast summarizer.
“Summarize the latest episode of HubermanLab”
And have it spit out key points and takeaways.
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Another example of pricing insanity:
Every day you will buy a coffee that you pee out 3 hrs later for $5.
Then a few hours later, you’ll complain about how $5/mo for Slack—the way you do your work, which makes you thousands a month—is too expensive.
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How are those Bored Apes and Punks working out for everyone?
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2. The best product doesn’t always win, and product is not a longterm competitive advantage.
3. If a tree falls in the forest and nobody is around to hear it, it didn’t fall.
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A tale of two business valuations:
Profitable Family Owned Business
- Growing 10% per year
- 20 year history
- $250,000 annual profit
Valuation: $750k to $1.5MM
20-Year-Old Kid with Startup Idea
- Doesn't exist yet
- No experience
- No profit or rev
Valuation: $4-6MM
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In 2013 I got a call from
@stewart
.
His gaming startup, Glitch, had failed.
He seemed gutted. They had burned through millions and laid off their entire staff.
He had an idea he wanted us to help with.
A last ditch effort to get his investors money back...
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The line between "busy person who writes really short emails" and "huge asshole" is very small.
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I just got back from 10 days in New Zealand 🇳🇿
And I think I'm in love.
I fell asleep on the plane from Vancouver and woke up groggy and out of it 10 hours later.
I was confused.
It was as if the plane had diverted back to British Columbia, except everyone had a mild stroke…
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"If you stand at a bus stop, eventually you'll catch a bus. But if you run from bus stop to bus stop, you may never catch a bus."
–Howard Marks
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"The big money is not in the buying or selling, but in the waiting."
–Charlie Munger
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There are four types of entrepreneurs:
1. People who try, give up, and get a job 🤦
2. People who get overwhelmed or comfortable, and stop growing ⚖️ (lifestyle)
3. People who grow steadily, year after year 📈 (compounders)
4. People who blitzscale 🚀(venture) ...
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For every Jeff Bezos, who succeeded...
There are 1,000 Jeff BOZOS who tried and failed spectacularly.
Unfortunately, they don't write books and go on podcasts to talk about the experience.
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In 2019, I set out to do something simple:
Recreate the local newspaper in digital form, by creating a simple daily newsletter focused on Victoria, Canada, my home town 📰
I hired a journalist and we started sending out a quick summary of what’s happening every day at 7AM...
Despite being a journalism school dropout, I've always loved the news.
Every morning for the past decade, I've read all the big papers (NYT, WSJ, FT) and been blown away by their investigative reporting.
Then I'd pickup our local newspaper, The Times Colonist, and feel sad...
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Something I’ve learned after almost twenty years in business:
Behind the scenes, every company is an unmitigated hair on fire disaster at most times.
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Has anyone copied the Costco model for restaurants?
Food sold at cost.
Employees paid well.
Memberships = profit.
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I'm working on a fun little Gmail plug-in side project...
It's an email firewall:
1. Filters out newsletters/noisy crap emails
2. Screens first time senders (similar to Hey)
3. Delivers emails a few times a day on a set schedule vs. 24/7 (like DnD)
Who wants to beta test?
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Asking a busy person if you can hop on a call and pick their brain is like asking someone you barely know to help you move.
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I love how VCs criticize founders who derisk by giving themselves a market salary or taking secondary, yet none of them are willing to give up their 2% management fee.
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Nothing has moved the needle for my personal happiness aside from:
👨👩👦 Kids
🧘 Gratitude/meditation
😴 Sleep
🏃 Exercise
💵 Making over $100k/year (zero happiness increase after that)
Everything else is a bottomless pit of achievement, yearning, and mimetic desire.
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Most product-focused CEOs think that if you build it, they will come ⚾️
In reality, if a tree falls in a forest and there's nobody around to hear it....nobody hears it 🌲🌲🌲
Marketing matters.
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Got to meet Michael Dell (
@MichaelDell
) in Austin yesterday.
Fun Fact: In 2021, his business made $777,000,000 in free cashflow per month.
And he owns 52% of it.
That makes him worth around $53.4 billion dollars, and one of the wealthiest people in the world.
Despite all…
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The more I speak to old people and learn about various people's lives, the one north star that seems to appear is:
Have kids.
As many as possible.
Make sure you have enough money to feed them.
Then be a good parent so they want to hang out with you when you're old.
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When you have an idea:
Immediately make a logo.
Build a simple website.
Make it real.
Give it tangible momentum
Skateboard🛹 -> Bike 🚲 -> Car 🚗
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No, I do not want to "hop on a call" to discuss something that we could write via email in 5-10 minutes 😭
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1/ Most entrepreneurs start with one goal in mind:
FREEDOM.
If you truly value freedom, you should have one goal for your first company:
Something that can produce $100-$200k of personal income.
It can be boring and doesn't have to scale.
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Real estate agents are one of the most egregious examples of misaligned incentives:
“It’s just 2.5%”
If I came to you and said “hi I’d like $25,000 for unlocking a few doors over a few weeks” you’d tell me to pound sand.
But a few % sounds like nothing so people go for it...
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I think
@elonmusk
had no choice but to remove the CEO and CFO of Twitter.
Here's why:
Investors who have never run a company think of businesses as spreadsheets.
But businesses aren’t spreadsheets.
They are groups of people.
And people are complicated...
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90% of creating strong friendships is just being consistent.
Carving out time. Saying yes. Not flaking.
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I think that failure is the best teacher.
But better than failing is getting to learn by reading about my failures in a tweet instead of losing $10MM yourself.
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If you want to become a pro soccer player, you go play soccer every waking hour.
In the same vein, if you want to get good at business, you need to DO BUSINESS, not sit in a classroom for 4 years reading about business.
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Overheard in New York:
“He’s making $13 million a year now, which is real money in Chicago”
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5. Running a SaaS business without deeply understanding churn, LTV, CAC etc, is like flying a plane without instrumentation—really stupid and dangerous.
6. Failure sneaks up on you slowly, then all at once.
7. R&D is EXPENSIVE. Especially when competing with venture.
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The goal of an entrepreneur should be to do nothing but route opportunities to the right people on your team.
Build a system and make yourself a human router 🚏
When I get stressed at work, it’s because I’ve failed to build a system and have tasks I can’t route to someone.
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I’ve spent 24 hours with the Apple Vision Pro.
I’ll start by saying this: I am the ultimate Apple fanboy.
Going back decades, no matter what Apple releases, I’ve been all in, to the point where my friends make fun of me for it.
Even when Apple ships something objectively bad,…
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It took me 15 years to learn this, but here’s how to hire people:
Hire someone who has done the exact task you need completed for another company, ideally at a slightly larger scale.
Make sure they jive with your team/not a jerk.
Not someone with potential
It’s that simple.
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Pretty much every entrepreneur I've talked to, no matter how simple and wonderful their business is, thinks it's the worst, most stressful dumpster fire, that could go out of business at any moment.
Everything is hard behind the scenes.
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It is INSANE how much sleep dictates my take on the whole situation.
Yesterday: 5-6 hrs of poor sleep. EXTREMELY anxious, projecting disaster all day.
Today: 8 hrs. Excited to dig into work, grab the wheel, and figure this out.
Sleep defines everything.
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Most people think Joe Rogan just did the deal of a lifetime with Spotify.
I think he got ripped off like a hapless farmer selling his oil rights for pennies on the dollar 🔥🛢️🔥💸💸💸
Here's why:
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Can somebody please steal this business idea from me and let me invest?
Every three months I wonder:
“Why hasn’t anyone done this yet?!”
Here's the idea...
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What’s an easier path to wealth?
PATH 1: VENTURE STARTUP
- 95% chance of $0
- Tiny personal income while building startup until IPO/scale
- Massive dilution (most founders end up owning 5-15%). $1BN market cap = $50-$150MM for founder.
OR...
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Can somebody summarize why it is logical to buy Bitcoin—other than speculation—in 1-3 sentences?
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10. Bootstrapping works best in uncompetitive spaces/niches or if you have an unfair advantage (a personal brand, unique customer acquisition channel, etc).
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There's an old saying:
Measure twice, cut once.
Too many entrepreneurs misunderstand this...
They measure 8 times, then never cut.
Analysis paralysis.
Cutting without measuring is better than never cutting at at all.
Perfect is the enemy of good.
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This x 10,000.
The number one mistake people make is thinking too big on their first business.
They try to start the next SpaceX when they should be starting a paving company.
Something boring that gets you the money to start the next SpaceX later.
Build the launch pad…
If you aren’t rich, every single business you start needs to be cashflow positive within two months.
If it isn’t, go get a job working for somebody who knows how to make money or a rich person with a big idea.
Sounds silly but this is why most people fail. Poor early decisions.
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A huge thank you to all of the people who worked on Flow over the past decade, I owe you all, big time.
I'm so sorry it didn't work out the way we had hoped and the responsibility falls squarely on my shoulders:
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“Work will settle down soon”
—Me, every day for the past 15 years
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Saying you want to "learn to code" to get into tech/start a startup is like saying "I want to learn how to lay bricks" when you're interested in becoming a real estate developer.
You don't need to learn to code. You need to understand how it all fits together.
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Victoria, where I live, is always beautiful, but with no pollution it’s just insane:
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Finding I’m generally happier during quarantine, especially on weekends.
No debate about how to spend the day.
No FOMO going to bed at 9 on a Friday.
Forced to cook at home, hang with family, and go on walks.
Longer flow states and less background noise anxiety...
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There is an insane amount of opportunity in understanding finance but speaking like a normal person and making it simple.
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We launched a business called Buyer...
It’s negotiation as a service.
Buying software? An office lease? A furniture order?
CC Buyer. They negotiate the best price for you.
They just saved Tiny $20k—just by asking for a discount.
I love this business!
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It’s a huge competitive advantage to just speak in normal, non-douchey terms with founders.
PE firms: “We are a $1.5BN mid market 10-year fund focused growth fund specializing in B2B SMB”
Us: “We own a bunch of profitable internet businesses. We’d like to buy your company.”
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“For most people, college was the last time it was normal to just randomly run into people.
As you get older, you drive to work, see the same people every day, then go home. But the best things happen when people are running into each other and sharing ideas.”
–Tony Hsieh
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The best entrepreneurs I know have one thing in common: As soon as they think of a great idea, they take one step toward making it a reality.
Coming up with a name.
Designing a logo.
Sketching it out.
Something.
So many great ideas are lost to analysis paralysis.
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I'm pretty confident that:
In 5-10 years, nobody will be aware of crypto 🪙
It will be long forgotten by everyone other than hardcore developers...
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After wearing a continuous glucose monitor for 1+ years, this is what I've learned🩸
- My mood/cravings are 100% tied to blood glucose. Low glucose = irritability. High glucose = sugar cravings.
- Sleep quality is 100% dependent on whether I have high overnight glucose...
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Nice clothes make you LOOK successful, but I’ve found in reality the most successful people I know dress the worst.
They don’t care. They aren’t trying to impress anyone.
It’s the sales people who dress well. The people who need something from you.
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