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.

Writing for readers:

14 years of daily writing.

I post practically everything on social media. I authored hundreds of articles, thousands of tweets, and numerous volumes to almost no one.

Tens of thousands of readers regularly praise me.

I despised writing. I'm stuck now.

I've learned what readers like and what doesn't.

Here are some essential guidelines for writing with impact:

Readers won't understand your work if you can't.

Though obvious, this slipped me up. Share your truths.

Stories engage human brains.

Showing the journey of a person from worm to butterfly inspires the human spirit.

Overthinking hinders powerful writing.

The best ideas come from inner understanding in between thoughts.

Avoid writing to find it. Write.

Writing a masterpiece isn't motivating.

Write for five minutes to simplify. Step-by-step, entertaining, easy steps.

Good writing requires a willingness to make mistakes.

So write loads of garbage that you can edit into a good piece.

Courageous writing.

A courageous story will move readers. Personal experience is best.

Go where few dare.

Templates, outlines, and boundaries help.

Limitations enhance writing.

Excellent writing is straightforward and readable, removing all the unnecessary fat.

Use five words instead of nine.

Use ordinary words instead of uncommon ones.

Readers desire relatability.

Too much perfection will turn it off.

Write to solve an issue if you can't think of anything to write.

Instead, read to inspire. Best authors read.

Every tweet, thread, and novel must have a central idea.

What's its point?

This can make writing confusing.

️ Don't direct your reader.

Readers quit reading. Demonstrate, describe, and relate.

Even if no one responds, have fun. If you hate writing it, the reader will too.

A top-down company plan facilitates decision-making and impresses investors.

A startup business plan starts with the product, the target customers, how to reach them, and how to grow the business.

Bottom-up is terrific unless venture investors fund it.

If it can prove how it can exceed $100M in sales, investors will invest. If not, the business may be wonderful, but it's not venture capital-investable.

As a rule, venture investors only fund firms that expect to reach $100M within 5 years.

Investors get nothing until an acquisition or IPO. To make up for 90% of failed investments and still generate 20% annual returns, portfolio successes must exit with a 25x return. A $20M-valued company must be acquired for $500M or more.

This requires $100M in sales (or being on a nearly vertical trajectory to get there). The company has 5 years to attain that milestone and create the requisite ROI.

This motivates venture investors (venture funds and angel investors) to hunt for $100M firms within 5 years. When you pitch investors, you outline how you'll achieve that aim.

I'm wary of pitches after seeing a million hockey sticks predicting $5M to $100M in year 5 that never materialized. Doubtful.

Startups fail because they don't have enough clients, not because they don't produce a great product. That jump from $5M to $100M never happens. The company reaches $5M or $10M, growing at 10% or 20% per year.  That's great, but not enough for a $500 million deal.

Once it becomes clear the company won’t reach orbit, investors write it off as a loss. When a corporation runs out of money, it's shut down or sold in a fire sale. The company can survive if expenses are trimmed to match revenues, but investors lose everything.

When I hear a pitch, I'm not looking for bright income projections but a viable plan to achieve them. Answer these questions in your pitch.

• Is the market size sufficient to generate $100 million in revenue?

• Will the initial beachhead market serve as a springboard to the larger market or as quicksand that hinders progress?

• What marketing plan will bring in $100 million in revenue? Is the market diffuse and will cost millions of dollars in advertising, or is it one, focused market that can be tackled with a team of salespeople?

• Will the business be able to bridge the gap from a small but fervent set of early adopters to a larger user base and avoid lock-in with their current solution?

• Will the team be able to manage a $100 million company with hundreds of people, or will hypergrowth force the organization to collapse into chaos?

• Once the company starts stealing market share from the industry giants, how will it deter copycats?

The requirement to reach $100M may be onerous, but it provides a context for difficult decisions: What should the product be? Where should we concentrate? who should we hire? Every strategic choice must consider how to reach $100M in 5 years.

Focusing on $100M streamlines investor pitches. Instead of explaining everything, focus on how you'll attain $100M.

As an investor, I know I'll lose my money if the startup doesn't reach this milestone, so the revenue prediction is the first thing I look at in a pitch deck.

Reaching the $100M goal needs to be the first thing the entrepreneur thinks about when putting together the business plan, the central story of the pitch, and the criteria for every important decision the company makes.

Unleash the power of the Option key ⌥

#1 Open a link in the Private tab first.

Previously, if I needed to open a Safari link in a private window, I would:

• copied the URL with the right click command,

• choose File > New Private Window to open a private window, and

• clicked return after pasting the URL.

I've found a more straightforward way.

Right-clicking a link shows this, right?

Hold option (⌥) for:

Click Open Link in New Private Window while holding.

Finished!

#2. Instead of searching for specific characters, try this

You may use unicode for business or school. Most people Google them when they need them.

That is lengthy!

You can type some special characters just by pressing ⌥ and a key.

For instance

• ⌥+2 -> ™ (Trademark)
• ⌥+0 -> ° (Degree)
• ⌥+G -> © (Copyright)
• ⌥+= -> ≠ (Not equal to)
• ⌥+< -> ≤ (Less than or equal to)
• ⌥+> -> ≥ (Greater then or equal to)
• ⌥+/ -> ÷ (Different symbol for division)

#3 Activate Do Not Disturb silently.

Do Not Disturb when sharing my screen is awkward for me (because people may think Im trying to hide some secret notifications).

Here's another method.

Hold ⌥ and click on Time (at the extreme right on the menu-bar).

Now, DND is activated (secretly!). To turn it off, do it again.

Note: This works only for DND focus.

#4. Resize a window starting from its center

Although this is rarely useful, it is still a hidden trick.

When you resize a window, the opposite edge or corner is used as the pivot, right?

However, if you want to resize it with its center as the pivot, hold while doing so.

#5. Yes, Cut-Paste is available on Macs as well (though it is slightly different).

I call it copy-move rather than cut-paste. This is how it works.

Carry it out.

Choose a file (by clicking on it), then copy it (⌘+C).

Go to a new location on your Mac. Do you use ⌘+V to paste it? However, to move it, press ⌘+⌥+V.

This removes the file from its original location and copies it here. And it works exactly like cut-and-paste on Windows.

#6. Instantly expand all folders

Set your Mac's folders to List view.

Assume you have one folder with multiple subfolders, each of which contains multiple files. And you wanted to look at every single file that was over there.

How would you do?

You're used to clicking the ⌄ glyph near the folder and each subfolder to expand them all, right? Instead, hold down ⌥ while clicking ⌄ on the parent folder.

This is what happens next.

Everything expands.

View/Copy a file's path as an added bonus

If you want to see the path of a file in Finder, select it and hold ⌥, and you'll see it at the bottom for a moment.

To copy its path, right-click on the folder and hold down ⌥ to see this

Click on Copy <"folder name"> as Pathname to do it.

#7 "Save As"

I was irritated by the lack of "Save As" in Pages when I first got a Mac (after 15 years of being a Windows guy).

It was necessary for me to save the file as a new file, in a different location, with a different name, or both.

Unfortunately, I couldn't do it on a Mac.

However, I recently discovered that it appears when you hold ⌥ when in the File menu.

Yay!

He’s not the President. Stop treating him like one.

Elon Musk tweeted from Qatar, where he was watching the World Cup Final with Jared Kushner.

Musk's subsequent Tweets were as normal, basic, and bland as anyone's from a World Cup Final: It's depressing to see the world's richest man looking at his phone during a grand ceremony. Rich guy goes to rich guy event didn't seem important.

Before Musk posted his should-I-step-down-at-Twitter poll, CNN ran a long segment asking if it was hypocritical for him to reveal his real-time location after defending his (very dumb) suspension of several journalists for (supposedly) revealing his assassination coordinates by linking to a site that tracks Musks private jet. It was hard to ignore CNN's hypocrisy: It covered Musk as Twitter CEO like President Trump. EVERY TRUMP STORY WAS BASED ON HIM SAYING X, THEN DOING Y. Trump would do something horrific, lie about it, then pretend it was fine, then condemn a political rival who did the same thing, be called hypocritical, and so on. It lasted four years. Exhausting.

It made sense because Trump was the President of the United States. The press's main purpose is to relentlessly cover and question the president.

It's strange to say this out. Twitter isn't America. Elon Musk isn't a president. He maintains a money-losing social media service to harass and mock people he doesn't like. Treating Musk like Trump, as if he should be held accountable like Trump, shows a startling lack of perspective. Some journalists treat Twitter like a country.

The compulsive, desperate way many journalists utilize the site suggests as much. Twitter isn't the town square, despite popular belief. It's a place for obsessives to meet and converse. Journalists say they're breaking news. Their careers depend on it. They can argue it's a public service. Nope. It's a place lonely people go to speak all day. Twitter. So do journalists, Trump, and Musk. Acting as if it has a greater purpose, as if it's impossible to break news without it, or as if the republic is in peril is ludicrous. Only 23% of Americans are on Twitter, while 25% account for 97% of Tweets. I'd think a large portion of that 25% are journalists (or attention addicts) chatting to other journalists. Their loudness makes Twitter seem more important than it is. Nope. It's another stupid website. They were there before Twitter; they will be there after Twitter. It’s just a website. We can all get off it if we want. Most of us aren’t even on it in the first place.

Musk is a website-owner. No world leader. He's not as accountable as Trump was. Musk is cable news's primary character now that Trump isn't (at least for now). Becoming a TV news anchor isn't as significant as being president. Elon Musk isn't as important as we all pretend, and Twitter isn't even close. Twitter is a dumb website, Elon Musk is a rich guy going through a midlife crisis, and cable news is lazy because its leaders thought the entire world was on Twitter and are now freaking out that their playground is being disturbed.

I’ve said before that you need to leave Twitter, now. But even if you’re still on it, we need to stop pretending it matters more than it does. It’s a site for lonely attention addicts, from the man who runs it to the journalists who can’t let go of it. It’s not a town square. It’s not a country. It’s not even a successful website. Let’s stop pretending any of it’s real. It’s not.