Unexpected Success

Shopify CEO and co-founder Tobias Lutke. Shopify is worth $48 billion.

World-renowned entrepreneur Tobi

Tobi never expected his first online snowboard business to become a multimillion-dollar software corporation.

Tobi founded Shopify to establish a 20-person company.

The publicly traded corporation employs over 10,000 people.

Here's Tobi Lutke's incredible story.

Elon Musk tweeted his admiration for the Shopify creator.

30-October-2019.

Musk praised Shopify founder Tobi Lutke on Twitter.

Happened:

Explore this programmer's journey.

What difficulties did Tobi experience as a young child?

Germany raised Tobi.

Tobi's parents realized he was smart but had trouble learning as a toddler.

Tobi was learning disabled.

Tobi struggled with school tests.

Tobi's learning impairments were undiagnosed.

Tobi struggled to read as a dyslexic.

Tobi also found school boring.

Germany's curriculum didn't inspire Tobi's curiosity.

“The curriculum in Germany was taught like here are all the solutions you might find useful later in life, spending very little time talking about the problem…If I don’t understand the problem I’m trying to solve, it’s very hard for me to learn about a solution to a problem.”

Studying computer programming

After tenth grade, Tobi decided school wasn't for him and joined a German apprenticeship program.

This curriculum taught Tobi software engineering.

He was an apprentice in a small Siemens subsidiary team.

Tobi worked with rebellious Siemens employees.

Team members impressed Tobi.

Tobi joined the team for this reason.

Tobi was pleased to get paid to write programming all day.

His life could not have been better.

Devoted to snowboarding

Tobi loved snowboarding.

He drove 5 hours to ski at his folks' house.

His friends traveled to the US to snowboard when he was older.

However, the cheap dollar conversion rate led them to Canada.

2000.

Tobi originally decided to snowboard instead than ski.

Snowboarding captivated him in Canada.

On the trip to Canada, Tobi encounters his wife.

Tobi meets his wife Fiona McKean on his first Canadian ski trip.

They maintained in touch after the trip.

Fiona moved to Germany after graduating.

Tobi was a startup coder.

Fiona found work in Germany.

Her work included editing, writing, and academics.

“We lived together for 10 months and then she told me that she need to go back for the master's program.”

With Fiona, Tobi immigrated to Canada.

Fiona invites Tobi.

Tobi agreed to move to Canada.

Programming helped Tobi move in with his girlfriend.

Tobi was an excellent programmer, therefore what he did in Germany could be done anywhere.

He worked remotely for his German employer in Canada.

Tobi struggled with remote work.

Due to poor communication.

No slack, so he used email.

Programmers had trouble emailing.

Tobi's startup was developing a browser.

After the dot-com crash, individuals left that startup.

It ended.

Tobi didn't intend to work for any major corporations.

Tobi left his startup.

He believed he had important skills for any huge corporation.

He refused to join a huge corporation.

Because of Siemens.

Tobi learned to write professional code and about himself while working at Siemens in Germany.

Siemens culture was odd.

Employees were distrustful.

Siemens' rigorous dress code implies that the corporation doesn't trust employees' attire.

It wasn't Tobi's place.

“There was so much bad with it that it just felt wrong…20-year-old Tobi would not have a career there.”

Focused only on snowboarding

Tobi lived in Ottawa with his girlfriend.

Canada is frigid in winter.

Ottawa's winters last.

Almost half a year.

Tobi wanted to do something worthwhile now.

So he snowboarded.

Tobi began snowboarding seriously.

He sought every snowboarding knowledge.

He researched the greatest snowboarding gear first.

He created big spreadsheets for snowboard-making technologies.

Tobi grew interested in selling snowboards while researching.

He intended to sell snowboards online.

He had no choice but to start his own company.

A small local company offered Tobi a job.

Interested.

He must sign papers to join the local company.

He needed a work permit when he signed the documents.

Tobi had no work permit.

He was allowed to stay in Canada while applying for permanent residency.

“I wasn’t illegal in the country, but my state didn’t give me a work permit. I talked to a lawyer and he told me it’s going to take a while until I get a permanent residency.”

Tobi's lawyer told him he cannot get a work visa without permanent residence.

His lawyer said something else intriguing.

Tobis lawyer advised him to start a business.

Tobi declined this local company's job offer because of this.

Tobi considered opening an internet store with his technical skills.

He sold snowboards online.

“I was thinking of setting up an online store software because I figured that would exist and use it as a way to sell snowboards…make money while snowboarding and hopefully have a good life.”

What brought Tobi and his co-founder together, and how did he support Tobi?

Tobi lived with his girlfriend's parents.

In Ottawa, Tobi encounters Scott Lake.

Scott was Tobis girlfriend's family friend and worked for Tobi's future employer.

Scott and Tobi snowboarded.

Tobi pitched Scott his snowboard sales software idea.

Scott liked the idea.

They planned a business together.

“I was looking after the technology and Scott was dealing with the business side…It was Scott who ended up developing relationships with vendors and doing all the business set-up.”

Issues they ran into when attempting to launch their business online

Neither could afford a long-term lease.

That prompted their online business idea.

They would open a store.

Tobi anticipated opening an internet store in a week.

Tobi seeks open-source software.

Most existing software was pricey.

Tobi and Scott couldn't afford pricey software.

“In 2004, I was sitting in front of my computer absolutely stunned realising that we hadn’t figured out how to create software for online stores.”

They required software to:

• to upload snowboard images to the website.

• people to look up the types of snowboards that were offered on the website. There must be a search feature in the software.

• Online users transmit payments, and the merchant must receive them.

• notifying vendors of the recently received order.

No online selling software existed at the time.

Online credit card payments were difficult.

How did they advance the software while keeping expenses down?

Tobi and Scott needed money to start selling snowboards.

Tobi and Scott funded their firm with savings.

“We both put money into the company…I think the capital we had was around CAD 20,000(Canadian Dollars).”

Despite investing their savings.

They minimized costs.

They tried to conserve.

No office rental.

They worked in several coffee shops.

Tobi lived rent-free at his girlfriend's parents.

He installed software in coffee cafes.

How were the software issues handled?

Tobi found no online snowboard sales software.

Two choices remained:

1. Change your mind and try something else.

2. Use his programming expertise to produce something that will aid in the expansion of this company.

Tobi knew he was the sole programmer working on such a project from the start.

“I had this realisation that I’m going to be the only programmer who has ever worked on this, so I don’t have to choose something that lots of people know. I can choose just the best tool for the job…There is been this programming language called Ruby which I just absolutely loved ”

Ruby was open-source and only had Japanese documentation.

Latin is the source code.

Tobi used Ruby twice.

He assumed he could pick the tool this time.

Why not build with Ruby?

How did they find their first time operating a business?

Tobi writes applications in Ruby.

He wrote the initial software version in 2.5 months.

Tobi and Scott founded Snowdevil to sell snowboards.

Tobi coded for 16 hours a day.

His lifestyle was unhealthy.

He enjoyed pizza and coke.

“I would never recommend this to anyone, but at the time there was nothing more interesting to me in the world.”

Their initial purchase and encounter with it

Tobi worked in cafes then.

“I was working in a coffee shop at this time and I remember everything about that day…At some time, while I was writing the software, I had to type the email that the software would send to tell me about the order.”

Tobi recalls everything.

He checked the order on his laptop at the coffee shop.

Pennsylvanian ordered snowboard.

Tobi walked home and called Scott. Tobi told Scott their first order.

They loved the order.

How were people made aware about Snowdevil?

2004 was very different.

Tobi and Scott attempted simple website advertising.

Google AdWords was new.

Ad clicks cost 20 cents.

Online snowboard stores were scarce at the time.

Google ads propelled the snowdevil brand.

Snowdevil prospered.

They swiftly recouped their original investment in the snowboard business because to its high profit margin.

Tobi and Scott struggled with inventories.

“Snowboards had really good profit margins…Our biggest problem was keeping inventory and getting it back…We were out of stock all the time.”

Selling snowboards returned their investment and saved them money.

They did not appoint a business manager.

They accomplished everything alone.

Sales dipped in the spring, but something magical happened.

Spring sales plummeted.

They considered stocking different boards.

They naturally wanted to add boards and grow the business.

However, magic occurred.

Tobi coded and improved software while running Snowdevil.

He modified software constantly. He wanted speedier software.

He experimented to make the software more resilient.

Tobi received emails requesting the Snowdevil license.

They intended to create something similar.

“I didn’t stop programming, I was just like Ok now let me try things, let me make it faster and try different approaches…Increasingly I got people sending me emails and asking me If I would like to licence snowdevil to them. People wanted to start something similar.”

Software or skateboards, your choice

Scott and Tobi had to choose a hobby in 2005.

They might sell alternative boards or use software.

The software was a no-brainer from demand.

Daniel Weinand is invited to join Tobi's business.

Tobis German best friend is Daniel.

Tobi and Scott chose to use the software.

Tobi and Scott kept the software service.

Tobi called Daniel to invite him to Canada to collaborate.

Scott and Tobi had quit snowboarding until then.

How was Shopify launched, and whence did the name come from?

The three chose Shopify.

Named from two words.

First:

• Shop

Final part:

• Simplify

Shopify

Shopify's crew has always had one goal:

• creating software that would make it simple and easy for people to launch online storefronts.

Launched Shopify after raising money for the first time.

Shopify began fundraising in 2005.

First, they borrowed from family and friends.

They needed roughly $200k to run the company efficiently.

$200k was a lot then.

When questioned why they require so much money. Tobi told them to trust him with their goals. The team raised seed money from family and friends.

Shopify.com has a landing page. A demo of their goal was on the landing page.

In 2006, Shopify had about 4,000 emails.

Shopify rented an Ottawa office.

“We sent a blast of emails…Some people signed up just to try it out, which was exciting.”

How things developed after Scott left the company

Shopify co-founder Scott Lake left in 2008.

Scott was CEO.

“He(Scott) realized at some point that where the software industry was going, most of the people who were the CEOs were actually the highly technical person on the founding team.”

Scott leaving the company worried Tobi.

Tobis worried about finding a new CEO.

To Tobi:

A great VC will have the network to identify the perfect CEO for your firm.

Tobi started visiting Silicon Valley to meet with venture capitalists to recruit a CEO.

Initially visiting Silicon Valley

Tobi came to Silicon Valley to start a 20-person company.

This company creates eCommerce store software.

Tobi never wanted a big corporation. He desired a fulfilling existence.

“I stayed in a hostel in the Bay Area. I had one roommate who was also a computer programmer. I bought a bicycle on Craiglist. I was there for a week, but ended up staying two and a half weeks.”

Tobi arrived unprepared.

When venture capitalists asked him business questions.

He answered few queries.

Tobi didn't comprehend VC meetings' terminology.

He wrote the terms down and looked them up.

Some were fascinated after he couldn't answer all these queries.

“I ended up getting the kind of term sheets people dream about…All the offers were conditional on moving our company to Silicon Valley.”

Canada received Tobi.

He wanted to consult his team before deciding. Shopify had five employees at the time.

2008.

A global recession greeted Tobi in Canada. The recession hurt the market.

His term sheets were useless.

The economic downturn in the world provided Shopify with a fantastic opportunity.

The global recession caused significant job losses.

Fired employees had several ideas.

They wanted online stores.

Entrepreneurship was desired. They wanted to quit work.

People took risks and tried new things during the global slump.

Shopify subscribers skyrocketed during the recession.

“In 2009, the company reached neutral cash flow for the first time…We were in a position to think about long-term investments, such as infrastructure projects.”

Then, Tobi Lutke became CEO.

How did Tobi perform as the company's CEO?

“I wasn’t good. My team was very patient with me, but I had a lot to learn…It’s a very subtle job.”

2009–2010.

Tobi limited the company's potential.

He deliberately restrained company growth.

Tobi had one costly problem:

• Whether Shopify is a venture or a lifestyle business.

The company's annual revenue approached $1 million.

Tobi battled with the firm and himself despite good revenue.

His wife was supportive, but the responsibility was crushing him.

“It’s a crushing responsibility…People had families and kids…I just couldn’t believe what was going on…My father-in-law gave me money to cover the payroll and it was his life-saving.”

Throughout this trip, everyone supported Tobi.

They believed it.

$7 million in donations received

Tobi couldn't decide if this was a lifestyle or a business.

Shopify struggled with marketing then.

Later, Tobi tried 5 marketing methods.

He told himself that if any marketing method greatly increased their growth, he would call it a venture, otherwise a lifestyle.

The Shopify crew brainstormed and voted on marketing concepts.

Tested.

“Every single idea worked…We did Adwords, published a book on the concept, sponsored a podcast and all the ones we tracked worked.”

To Silicon Valley once more

Shopify marketing concepts worked once.

Tobi returned to Silicon Valley to pitch investors.

He raised $7 million, valuing Shopify at $25 million.

All investors had board seats.

“I find it very helpful…I always had a fantastic relationship with everyone who’s invested in my company…I told them straight that I am not going to pretend I know things, I want you to help me.”

Tobi developed skills via running Shopify.

Shopify had 20 employees.

Leaving his wife's parents' home

Tobi left his wife's parents in 2014.

Tobi had a child.

Shopify has 80,000 customers and 300 staff in 2013.

Public offering in 2015

Shopify investors went public in 2015.

Shopify powers 4.1 million e-Commerce sites.

Shopify stores are 65% US-based.

It is currently valued at $48 billion.

From a simple landing where we tested our MVP to a platform that distributes 20,000 codes per month, we learned a lot.

Starting point

Kwotet was my first startup. Everyone might post book quotes online.

I wanted a change.

Kwotet lacked attention, thus I felt stuck. After experiencing the trials of starting Kwotet, I thought of developing a waitlist service, but I required a strong co-founder.

I knew Dries from school, but we weren't close. He was an entrepreneurial programmer who worked a lot outside school. I needed this.

We brainstormed throughout school hours. We developed features to put us first. We worked until 3 am to launch this product.

Putting in the hours is KEY when building a startup

The instant that we lost our spark

In Belgium, college seniors do their internship in their last semester.

As we both made the decision to pick a quite challenging company, little time was left for Lancero.

Eventually, we lost interest. We lost the spark…

The only logical choice was to find someone with the same spark we started with to acquire Lancero.

And we did @ MicroAcquire.

Sell before your product dies. Make sure to profit from all the gains.

What did we do following the sale?

Not far from selling Lancero I lost my dad. I was about to start a new company. It was focused on positivity. I got none left at the time.

We still didn’t let go of the dream of becoming full-time entrepreneurs. As Dries launched the amazing company Plunk, and I’m still in the discovering stages of my next journey!

Dream!

You’re an entrepreneur if:

• You're imaginative.

• You enjoy disassembling and reassembling things.

• You're adept at making new friends.

• YOU HAVE DREAMS.

You don’t need to believe me if I tell you “everything is possible”… I wouldn't believe it myself if anyone told me this 2 years ago.

Until I started doing, living my dreams.

Niches are rich, as the adage goes.

Micro SaaS requires a great micro-niche; otherwise, it's merely plain old SaaS with a large audience.

Instead of targeting broad markets with few identifying qualities, specialise down to a micro-niche. How would you target these users?

Better go tiny. You'll locate and engage new consumers more readily and serve them better with a customized solution.

Imagine you're a real estate lawyer looking for a case management solution. Because it's so specific to you, you'd be lured to this link:

instead of below:

Next, locate mini SaaS niches that could work for you. You're not yet looking at the problems/solutions in these areas, merely shortlisting them.

The market should be growing, not shrinking

We shouldn't design apps for a declining niche. We intend to target stable or growing niches for the next 5 to 10 years.

If it's a developing market, you may be able to claim a stake early. You must balance this strategy with safer, longer-established niches (accountancy, law, health, etc).

First Micro SaaS apps I designed were for Merch By Amazon creators, a burgeoning niche. I found this niche when searching for passive income.

Graphic designers and entrepreneurs post their art to Amazon to sell on clothes. When Amazon sells their design, they get a royalty. Since 2015, this platform and specialty have grown dramatically.

Amazon doesn't publicize the amount of creators on the platform, but it's possible to approximate by looking at Facebook groups, Reddit channels, etc.

I could see the community growing week by week, with new members joining. Merch was an up-and-coming niche, and designers made money when their designs sold. All I had to do was create tools that let designers focus on making bestselling designs.

Look at the Google Trends graph below to see how this niche has evolved and when I released my apps and resigned my job.

Are the users able to afford the tools?

Who's your average user? Consumer or business? Is your solution budgeted?

If they're students, you'll struggle to convince them to subscribe to your study-system app (ahead of video games and beer).

Let's imagine you designed a Shopify plugin that emails customers when a product is restocked. If your plugin just needs 5 product sales a month to justify its cost, everyone wins (just be mindful that one day Shopify could potentially re-create your plugins functionality within its core offering making your app redundant ).

Do specialized users buy tools? If so, that's comforting. If not, you'd better have a compelling value proposition for your end customer if you're the first.

This should include how much time or money your program can save or make the user.

Are you able to understand the Micro SaaS market?

Ideally, you're already familiar about the industry/niche. Maybe you're fixing a challenge from your day job or freelance work.

If not, evaluate how long it would take to learn the niche's users. Health & Fitness is easier to relate to and understand than hedge fund derivatives trading.

Competing in these complex (and profitable) fields might offer you an edge.

B2C, B2M, or B2B?

Consider your user base's demographics. Will you target businesses, consumers, or both? Let's examine the different consumer types:

• B2B refers to business-to-business transactions where customers are other businesses. UpVoty, Plutio, Slingshot, Salesforce, Atlassian, and Hubspot are a few examples of SaaS, ranging from Micro SaaS to SaaS.

• Business to Consumer (B2C), in which your clients are people who buy things. For instance, Duolingo, Canva, and Nomad List.

• For instance, my tool KDP Wizard has a mixed user base of publishing enterprises and also entrepreneurial consumers selling low-content books on Amazon. This is a case of business to many (B2M), where your users are a mixture of businesses and consumers. There is a large SaaS called Dropbox that offers both personal and business plans.

Targeting a B2B vs. B2C niche is very different. The sales cycle differs.

• A B2B sales staff must make cold calls to potential clients' companies. Long sales, legal, and contractual conversations are typically required for each business to get the go-ahead. The cost of obtaining a new customer is substantially more than it is for B2C, despite the fact that the recurring fees are significantly higher.

• Since there is typically only one individual making the purchasing decision, B2C signups are virtually always self-service with reduced recurring fees. Since there is typically no outbound sales staff in B2C, acquisition costs are significantly lower than in B2B.

User Characteristics for B2B vs. B2C

Consider where your niche's users congregate if you don't already have a presence there.

B2B users frequent LinkedIn and Twitter. B2C users are on Facebook/Instagram/Reddit/Twitter, etc.

Churn is higher in B2C because consumers haven't gone through all the hoops of a B2B sale. Consumers are more unpredictable than businesses since they let their bank cards exceed limitations or don't update them when they expire.

With a B2B solution, there's a contractual arrangement and the firm will pay the subscription as long as they need it.

Depending on how you feel about the above (sales team vs. income vs. churn vs. targeting), you'll know which niches to pursue.

You ought to respect potential customers.

Would you hang out with customers?

You'll connect with users at conferences (in-person or virtual), webinars, seminars, screenshares, Facebook groups, emails, support calls, support tickets, etc.

If talking to a niche's user base makes you shudder, you're in for a tough road. Whether they're demanding or dull, avoid them if possible.

Merch users are mostly graphic designers, side hustlers, and entrepreneurs. These laid-back users embrace technologies that assist develop their Merch business.

I discovered there was only one annual conference for this specialty, held in Seattle, USA. I decided to organize a conference for UK/European Merch designers, despite never having done so before.

Hosting a conference for over 80 people was stressful, and it turned out to be much bigger than expected, with attendees from the US, Europe, and the UK.

I met many specialized users, built relationships, gained trust, and picked their brains in person. Many of the attendees were already Merch Wizard users, so hearing their feedback and ideas for future features was invaluable.

focused and specific

Instead of building for a generic, hard-to-reach market, target a specific group.

I liken it to fishing in a little, hidden pond. This small pond has only one species of fish, so you learn what bait it likes. Contrast that with trawling for hours to catch as many fish as possible, even if some aren't what you want.

In the case management scenario, it's difficult to target leads because several niches could use the app. Where do your potential customers hang out? Your generic solution: No.

It's easier to join a community of Real Estate Lawyers and see if your software can answer their pain points.

My Success with Micro SaaS

In my case, my Micro SaaS apps have been my chrome extensions. Since I launched them, they've earned me an average $10k MRR, allowing me to quit my lousy full-time job years ago.

I sold my apps after scaling them for a life-changing lump amount. Since then, I've helped unfulfilled software developers escape the 9-5 through Micro SaaS.

Whether it's a profitable side hustle or a liferaft to quit their job and become their own Micro SaaS boss.

Having built my apps to the point where I could quit my job, then scaled and sold them, I feel I can share my skills with software developers worldwide.

Read my free guide on self-funded SaaS to discover more about Micro SaaS, or download your own copy. 12 chapters cover everything from Idea to Exit.

Watch my YouTube video to learn how to construct a Micro SaaS app in 10 steps.

I've spent the last 10 years of my career mastering time management. I've tried different approaches and followed multiple people and sources. My knowledge is summarized.

Great people, including entrepreneurs, master time management. I learned time management in college. I was studying Computer Science and Finance and leading Tanzanian students in Bangalore, India. I had 24 hours per day to do this and enjoy campus. I graduated and received several awards. I've learned to maximize my time. These tips and tools help me finish quickly.

Eisenhower-Box

I don't remember when I read the article. James Clear, one of my favorite bloggers, introduced me to the Eisenhower Box, which I've used for years. Eliminate waste to master time management. By grouping your activities by importance and urgency, the tool helps you prioritize what matters and drop what doesn't. If it's urgent, do it. Delegate if it's urgent but not necessary. If it's important but not urgent, reschedule it; otherwise, drop it. I integrated the tool with Trello to manage my daily tasks. Since 2007, I've done this.

James Clear's article mentions Eisenhower Box.

Essentialism rules

Greg McKeown's book Essentialism introduced me to disciplined pursuit of less. I once wrote about this. I wasn't sure what my career's real opportunities and distractions were. A non-essentialist thinks everything is essential; you want to be everything to everyone, and your life lacks satisfaction. Poor time management starts it all. Reading and applying this book will change your life.

Essential vs non-essential

Life Calendar

Most of us make corporate calendars. Peter Njonjo, founder of Twiga Foods, said he manages time by putting life activities in his core calendars. It includes family retreats, weddings, and other events. He joked that his wife always complained to him to avoid becoming a calendar item. It's key. "Time Masters" manages life's four burners, not just work and corporate life. There's no "work-life balance"; it's life.

Health, Family, Work, and Friends.

The Brutal No

In a culture where people want to look good, saying "NO" to a favor request seems rude. In reality, the crime is breaking a promise. "Time Masters" have mastered "NO".  More "YES" means less time, and more "NO" means more time for tasks and priorities. Brutal No doesn't mean being mean to your coworkers; it means explaining kindly and professionally that you have other priorities.

To-Do vs. MITs

Most people are productive with a routine to-do list. You can't be effective by just checking boxes on a To-do list. When was the last time you completed all of your daily tasks? Never. You must replace the to-do list with Most Important Tasks (MITs). MITs allow you to focus on the most important tasks on your list. You feel progress and accomplishment when you finish these tasks. MITs don't include ad-hoc emails, meetings, etc.

Journal Mapped

Most people don't journal or plan their day in the developing South. I've learned to plan my day in my journal over time. I have multiple sections on one page: MITs (things I want to accomplish that day), Other Activities (stuff I can postpone), Life (health, faith, and family issues), and Pop-Ups (things that just pop up). I leave the next page blank for notes. I reflected on the blocks to identify areas to improve the next day. You will have bad days, but at least you'll realize it was due to poor time management.

Buy time/delegate

Time or money? When you make enough money, you lose time to make more. The smart buy "Time." I resisted buying other people's time for years. I regret not hiring an assistant sooner. Learn to buy time from others and pay for time-consuming tasks. Sometimes you think you're saving money by doing things yourself, but you're actually losing money.

This post is a summary. See the full post here.

I read 53 novels last year and hope to do so again.

Books are best if you love learning. You get a range of perspectives, unlike podcasts and YouTube channels where you get the same ones.

Book quality varies. I've read useless books. Most books teach me something.

These 9 novels have changed my outlook in recent years. They've made me rethink what I believed or introduced me to a fresh perspective that changed my worldview.

You can order these books yourself. Or, read my summaries to learn what I've synthesized.

Enjoy!

Fooled By Randomness

Nassim Taleb worked as a Wall Street analyst. He used options trading to bet on unlikely events like stock market crashes.

Using financial models, investors predict stock prices. The models assume constant, predictable company growth.

These models base their assumptions on historical data, so they assume the future will be like the past.

Fooled By Randomness argues that the future won't be like the past. We often see impossible market crashes like 2008's housing market collapse. The world changes too quickly to use historical data: by the time we understand how it works, it's changed.

Most people don't live to see history unfold. We think our childhood world will last forever. That goes double for stable societies like the U.S., which hasn't seen major turbulence in anyone's lifetime.

Fooled By Randomness taught me to expect the unexpected. The world is deceptive and rarely works as we expect. You can't always trust your past successes or what you've learned.

Antifragile

More Taleb. Some things, like the restaurant industry and the human body, improve under conditions of volatility and turbulence.

We didn't have a word for this counterintuitive concept until Taleb wrote Antifragile. The human body (which responds to some stressors, like exercise, by getting stronger) and the restaurant industry both benefit long-term from disorder (when economic turbulence happens, bad restaurants go out of business, improving the industry as a whole).

Many human systems are designed to minimize short-term variance because humans don't understand it. By eliminating short-term variation, we increase the likelihood of a major disaster.

Once, we put out every forest fire we found. Then, dead wood piled up in forests, causing catastrophic fires.

We don't like price changes, so politicians prop up markets with stimulus packages and printing money. This leads to a bigger crash later. Two years ago, we printed a ton of money for stimulus checks, and now we have double-digit inflation.

Antifragile taught me how important Plan B is. A system with one or two major weaknesses will fail. Make large systems redundant, foolproof, and change-responsive.

Reality is broken

We dread work. Work is tedious. Right?

Wrong. Work gives many people purpose. People are happiest when working. (That's why some are workaholics.)

Factory work saps your soul, office work is boring, and working for a large company you don't believe in and that operates unethically isn't satisfying.

Jane McGonigal says in Reality Is Broken that meaningful work makes us happy. People love games because they simulate good work. McGonigal says work should be more fun.

Some think they'd be happy on a private island sipping cocktails all day. That's not true. Without anything to do, most people would be bored. Unemployed people are miserable. Many retirees die within 2 years, much more than expected.

Instead of complaining, find meaningful work. If you don't like your job, it's because you're in the wrong environment. Find the right setting.

The Lean Startup

Before the airplane was invented, Harvard scientists researched flying machines. Who knew two North Carolina weirdos would beat them?

The Wright Brothers' plane design was key. Harvard researchers were mostly theoretical, designing an airplane on paper and trying to make it fly in theory. They'd build it, test it, and it wouldn't fly.

The Wright Brothers were different. They'd build a cheap plane, test it, and it'd crash. Then they'd learn from their mistakes, build another plane, and it'd crash.

They repeated this until they fixed all the problems and one of their planes stayed aloft.

Mistakes are considered bad. On the African savannah, one mistake meant death. Even today, if you make a costly mistake at work, you'll be fired as a scapegoat. Most people avoid failing.

In reality, making mistakes is the best way to learn.

Eric Reis offers an unintuitive recipe in The Lean Startup: come up with a hypothesis, test it, and fail. Then, try again with a new hypothesis. Keep trying, learning from each failure.

This is a great startup strategy. Startups are new businesses. Startups face uncertainty. Run lots of low-cost experiments to fail, learn, and succeed.

Don't fear failing. Low-cost failure is good because you learn more from it than you lose. As long as your worst-case scenario is acceptable, risk-taking is good.

The Sovereign Individual

Today, nation-states rule the world. The UN recognizes 195 countries, and they claim almost all land outside of Antarctica.

We agree. For the past 2,000 years, much of the world's territory was ungoverned.

Why today? Because technology has created incentives for nation-states for most of the past 500 years. The logic of violence favors nation-states, according to James Dale Davidson, author of the Sovereign Individual. Governments have a lot to gain by conquering as much territory as possible, so they do.

Not always. During the Dark Ages, Europe was fragmented and had few central governments. Partly because of armor. With armor, a sword, and a horse, you couldn't be stopped. Large states were hard to form because they rely on the threat of violence.

When gunpowder became popular in Europe, violence changed. In a world with guns, assembling large armies and conquest are cheaper.

James Dale Davidson says the internet will make nation-states obsolete. Most of the world's wealth will be online and in people's heads, making capital mobile.

Nation-states rely on predatory taxation of the rich to fund large militaries and welfare programs.

When capital is mobile, people can live anywhere in the world, Davidson says, making predatory taxation impossible. They're not bound by their job, land, or factory location. Wherever they're treated best.

Davidson says that over the next century, nation-states will collapse because they won't have enough money to operate as they do now. He imagines a world of small city-states, like Italy before 1900. (or Singapore today).

We've already seen some movement toward a more Sovereign Individual-like world. The pandemic proved large-scale remote work is possible, freeing workers from their location. Many cities and countries offer remote workers incentives to relocate.

Many Western businesspeople live in tax havens, and more people are renouncing their US citizenship due to high taxes. Increasing globalization has led to poor economic conditions and resentment among average people in the West, which is why politicians like Trump and Sanders rose to popularity with angry rhetoric, even though Obama rose to popularity with a more hopeful message.

The Sovereign Individual convinced me that the future will be different than Nassim Taleb's. Large countries like the U.S. will likely lose influence in the coming decades, while Portugal, Singapore, and Turkey will rise. If the trend toward less freedom continues, people may flee the West en masse.

So a traditional life of college, a big firm job, hard work, and corporate advancement may not be wise. Young people should learn as much as possible and develop flexible skills to adapt to the future.

Sapiens

Sapiens is a history of humanity, from proto-humans in Ethiopia to our internet society today, with some future speculation.

Sapiens views humans (and Homo sapiens) as a unique species on Earth. We were animals 100,000 years ago. We're slowly becoming gods, able to affect the climate, travel to every corner of the Earth (and the Moon), build weapons that can kill us all, and wipe out thousands of species.

Sapiens examines what makes Homo sapiens unique. Humans can believe in myths like religion, money, and human-made entities like countries and LLCs.

These myths facilitate large-scale cooperation. Ants from the same colony can cooperate. Any two humans can trade, though. Even if they're not genetically related, large groups can bond over religion and nationality.

Combine that with intelligence, and you have a species capable of amazing feats.

Sapiens may make your head explode because it looks at the world without presupposing values, unlike most books. It questions things that aren't usually questioned and says provocative things.

It also shows how human history works. It may help you understand and predict the world. Maybe.

The 4-hour Workweek

Things can be done better.

Tradition, laziness, bad bosses, or incentive structures cause complacency. If you're willing to make changes and not settle for the status quo, you can do whatever you do better and achieve more in less time.

The Four-Hour Work Week advocates this. Tim Ferriss explains how he made more sales in 2 hours than his 8-hour-a-day colleagues.

By firing 2 of his most annoying customers and empowering his customer service reps to make more decisions, he was able to leave his business and travel to Europe.

Ferriss shows how to escape your 9-to-5, outsource your life, develop a business that feeds you with little time, and go on mini-retirement adventures abroad.

Don't accept the status quo. Instead, level up. Find a way to improve your results. And try new things.

Why Nations Fail

Nogales, Arizona and Mexico were once one town. The US/Mexico border was arbitrarily drawn.

Both towns have similar cultures and populations. Nogales, Arizona is well-developed and has a high standard of living. Nogales, Mexico is underdeveloped and has a low standard of living. Whoa!

Why Nations Fail explains how government-created institutions affect country development. Strong property rights, capitalism, and non-corrupt governments promote development. Countries without capitalism, strong property rights, or corrupt governments don't develop.

Successful countries must also embrace creative destruction. They must offer ordinary citizens a way to improve their lot by creating value for others, not reducing them to slaves, serfs, or peasants. Authors say that ordinary people could get rich on trading expeditions in 11th-century Venice.

East and West Germany and North and South Korea have different economies because their citizens are motivated differently. It explains why Chile, China, and Singapore grow so quickly after becoming market economies.

People have spent a lot of money on third-world poverty. According to Why Nations Fail, education and infrastructure aren't the answer. Developing nations must adopt free-market economic policies.

Elon Musk

Elon Musk is the world's richest man, but that’s not a good way to describe him. Elon Musk is the world's richest man, which is like calling Steve Jobs a turtleneck-wearer or Benjamin Franklin a printer.

Elon Musk does cool sci-fi stuff to help humanity avoid existential threats.

Oil will run out. We've delayed this by developing better extraction methods. We only have so much nonrenewable oil.

Our society is doomed if it depends on oil. Elon Musk invested heavily in Tesla and SolarCity to speed the shift to renewable energy.

Musk worries about AI: we'll build machines smarter than us. We won't be able to stop these machines if something goes wrong, just like cows can't fight humans. Neuralink: we need to be smarter to compete with AI when the time comes.

If Earth becomes uninhabitable, we need a backup plan. Asteroid or nuclear war could strike Earth at any moment. We may not have much time to react if it happens in a few days. We must build a new civilization while times are good and resources are plentiful.

Short-term problems dominate our politics, but long-term issues are more important. Long-term problems can cause mass casualties and homelessness. Musk demonstrates how to think long-term.

The main reason people are impressed by Elon Musk, and why Ashlee Vances' biography influenced me so much, is that he does impossible things.

Electric cars were once considered unprofitable, but Tesla has made them mainstream. SpaceX is the world's largest private space company.

People lack imagination and dismiss ununderstood ideas as impossible. Humanity is about pushing limits. Don't worry if your dreams seem impossible. Try it.

Thanks for reading.

VeeFriends is one NFT project I'm sure will last.

I believe in blockchain technology and JPEGs, aka NFTs. NFTs aren't JPEGs. It's not as it seems.

Gary Vaynerchuk is leading the pack with his new NFT project VeeFriends, I wrote a year ago. I was spot-on. It's the most innovative project I've seen.

Since its minting in May 2021, it has given its holders enormous value, most notably the first edition of VeeCon, a multi-day superconference featuring iconic and emerging leaders in NFTs and Popular Culture. First-of-its-kind NFT-ticketed Web3 conference to build friendships, share ideas, and learn together.

VeeFriends holders got free VeeCon NFT tickets. Attendees heard iconic keynote speeches, innovative talks, panels, and Q&A sessions.

It was a unique conference that most of us, including me, are looking forward to in 2023. The lineup was epic, and it allowed many to network in new ways. Really memorable learning. Here are a couple of gratitude posts from the attendees.

VeeFriends Series 2

This article explains VeeFriends if you're still confused.

GaryVee's hand-drawn doodles have evolved into wonderful characters. The characters' poses and backgrounds bring the VeeFriends IP to life.

Yes, this is the second edition of VeeFriends, and at current prices, it's one of the best NFT opportunities in years. If you have the funds and risk appetite to invest in NFTs, VeeFriends Series 2 is worth every penny. Even if you can't invest, learn from their journey.

1. Art Is the Start

Many critics say VeeFriends artwork is below average and not by GaryVee. Art is often the key to future success.

Let's look at one of the first Mickey Mouse drawings. No one would have guessed that this would become one of the most beloved animated short film characters. In Walt Before Mickey, Walt Disney's original mouse Mortimer was less refined.

First came a mouse...

These sketches evolved into Steamboat Willie, Disney's first animated short film.

Fred Moore redesigned the character artwork into what we saw in cartoons as kids. Mickey Mouse's history is here.

Looking at how different cartoon characters have evolved and gained popularity over decades, I believe Series 2 characters like Self-Aware Hare, Kind Kudu, and Patient Pig can do the same.

GaryVee captures this journey on the blockchain and lets early supporters become part of history. Time will tell if it rivals Disney, Pokemon, or Star Wars. Gary has been vocal about this vision.

2. VeeFriends is Intellectual Property for the Coming Generations

Most of us grew up watching cartoons, playing with toys, cards, and video games. Our interactions with fictional characters and the stories we hear shape us.

GaryVee is slowly curating an experience for the next generation with animated videos, card games, merchandise, toys, and more.

VeeFriends UNO, a collaboration with Mattel Creations, features 17 VeeFriends characters.

VeeFriends and Zerocool recently released Trading Cards featuring all 268 Series 1 characters and 15 new ones. Another way to build VeeFriends' collectibles brand.

At Veecon, all the characters were collectible toys. Something will soon emerge.

Kids and adults alike enjoy the YouTube channel's animated shorts and VeeFriends Tunes. Here's a song by the holder's Optimistic Otter-loving daughter.

This VeeFriends story is only the beginning. I'm looking forward to animated short film series, coloring books, streetwear, candy, toys, physical collectibles, and other forms of VeeFriends IP.

3. Veefriends will always provide utilities

Smart contracts can be updated at any time and authenticated on a ledger.

VeeFriends Series 2 gives no promise of any utility whatsoever. GaryVee released no project roadmap. In the first few months after launch, many owners of specific characters or scenes received utilities.

Every benefit or perk you receive helps promote the VeeFriends brand.

Recent partnerships are listed below.

• MaryRuth's Multivitamin Gummies

• Productive Puffin holders from VeeFriends x Primitive

• Pickleball Scene & Clown Holders Only

Pickleball & Competitive Clown Exclusive experience, anteater multivitamin gummies, and Puffin x Primitive merch

Considering the price of NFTs, it may not seem like much. It's just the beginning; you never know what the future holds. No other NFT project offers such diverse, ongoing benefits.

4. Garyvee's team is ready

Gary Vaynerchuk's team and record are undisputed. He's a serial entrepreneur and the Chairman & CEO of VaynerX, which includes VaynerMedia, VaynerCommerce, One37pm, and The Sasha Group.

Gary founded VaynerSports, Resy, and Empathy Wines. He's a Candy Digital Board Member, VCR Group Co-Founder, ArtOfficial Co-Founder, and VeeFriends Creator & CEO. Gary was recently named one of Fortune's Top 50 NFT Influencers.

Gary Vayenerchuk aka GaryVee

Gary documents his daily life as a CEO on social media, which has 34 million followers and 272 million monthly views. GaryVee Audio Experience is a top podcast. He's a five-time New York Times best-seller and sought-after speaker.

Gary can observe consumer behavior to predict trends. He understood these trends early and pioneered them.

• 1997 — Realized e-potential commerce's and started winelibrary.com. In five years, he grew his father's wine business from $3M to $60M.

• 2006 — Realized content marketing's potential and started Wine Library on YouTube. TV

• 2009 — Estimated social media's potential (Web2) and invested in Facebook, Twitter, and Tumblr.

• 2014: Ethereum and Bitcoin investments

• 2021 — Believed in NFTs and Web3 enough to launch VeeFriends

GaryVee isn't all of VeeFriends. Andy Krainak, Dave DeRosa, Adam Ripps, Tyler Dowdle, and others work tirelessly to make VeeFriends a success.

GaryVee has said he'll let other businesses fail but not VeeFriends. We're just beginning his 40-year vision.

I have more confidence than ever in a company with a strong foundation and team.

5. Humans die, but characters live forever

What if GaryVee dies or can't work?

A writer's books can immortalize them. As long as their books exist, their words are immortal. Socrates, Hemingway, Aristotle, Twain, Fitzgerald, and others have become immortal.

Everyone knows Vincent Van Gogh's The Starry Night.

We all love reading and watching Peter Parker, Thor, or Jessica Jones. Their behavior inspires us. Stan Lee's message and stories live on despite his death.

GaryVee represents VeeFriends. Creating characters to communicate ensures that the message reaches even those who don't listen.

Gary wants his values and messages to be omnipresent in 268 characters. Messengers die, but their messages live on.

Gary envisions VeeFriends creating timeless stories and experiences. Ten years from now, maybe every kid will sing Patient Pig.

6. I love the intent.

Gary planned to create Workplace Warriors three years ago when he began designing Patient Panda, Accountable Ant, and Empathy elephant. The project stalled. When NFTs came along, he knew.

Gary wanted to create characters with traits he values, such as accountability, empathy, patience, kindness, and self-awareness. He wants future generations to find these traits cool. He hopes one or more of his characters will become pop culture icons.

These emotional skills aren't taught in schools or colleges, but they're crucial for business and life success. I love that someone is teaching this at scale.

In the end, intent matters.

Humans Are Collectors

Buy and collect things to communicate. Since the 1700s. Medieval people formed communities around hidden metals and stones. Many people still collect stamps and coins, and luxury and fashion are multi-trillion dollar industries. We're collectors.

The early 2020s NFTs will be remembered in the future. VeeFriends will define a cultural and technological shift in this era. VeeFriends Series 1 is the original hand-drawn art, but it's expensive. VeeFriends Series 2 is a once-in-a-lifetime opportunity at $1,000.

If you are new to NFTs, check out How to Buy a Non Fungible Token (NFT) For Beginners

This is a non-commercial article. Not financial or legal advice. Information isn't always accurate. Before making important financial decisions, consult a pro or do your own research.

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