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.

Reflections on the closed company Hola! Dating app

I'll discuss my fuckups as an entrepreneur and CEO. All of them refer to the dating app Hola!, which I co-founded and starred in.

Spring 2021 was when we started. Two techies and two non-techies created a dating app. Pokemon Go and Tinder were combined.

Online dating is a business, and it takes two weeks from a like to a date. We questioned online dating app users if they met anyone offline last year.

75% replied yes, 50% sometimes, 25% usually.

Offline dating is popular, yet people have concerns.

• Men are reluctant to make mistakes in front of others.

• Women are curious about the background of everyone who approaches them.

We designed unique mechanics that let people date after a match. No endless chitchat. Women would be safe while men felt like cowboys.

I wish to emphasize three faults that lead to founders' estrangement.

This detachment ultimately led to us shutting down the company.

The wrong technology stack

Situation

Instead of generating a faster MVP and designing an app in a universal stack for iOS and Android, I argued we should pilot the app separately for iOS and Android. Technical founders' expertise made this possible.

Self-reflection

Mistaken strategy. We lost time and resources developing two apps at once. We chose iOS since it's more profitable. Apple took us out after the release, citing Guideline 4.3 Spam. After 4 months, we had nothing. We had a long way to go to get the app on Android and the Store.

I suggested creating a uniform platform for the company's growth. This makes parallel product development easier. The strategist's lack of experience and knowledge made it a piece of crap.

What would I have changed if I could?

We should have designed an Android universal stack. I expected Apple to have issues with a dating app.

Our approach should have been to launch something and subsequently improve it, but prejudice won.

The lesson

Discuss the IT stack with your CTO. It saves time and money. Choose the easiest MVP method.

2. A tardy search for investments

Situation

Though the universe and other founders encouraged me to locate investors first, I started pitching when we almost had an app.

When angels arrived, it was time to close. The app was banned, war broke out, I left the country, and the other co-founders stayed. We had no savings.

Self-reflection

I loved interviewing users. I'm proud of having done 1,000 interviews. I wanted to understand people's pain points and improve the product.

Interview results no longer affected the product. I was terrified to start pitching. I filled out accelerator applications and redid my presentation. You must go through that so you won't be terrified later.

What would I have changed if I could?

Get an external or internal mentor to help me with my first pitch as soon as possible. I'd be supported if criticized. He'd cheer with me if there was enthusiasm.

In 99% of cases, I'm comfortable jumping into the unknown, but there are exceptions. The mentor's encouragement would have prompted me to act sooner.

The lesson

Begin fundraising immediately. Months may pass. Show investors your pre-MVP project. Draw inferences from feedback.

3. Role ambiguity

Situation

My technical co-founders were also part-time lead developers, which produced communication issues. As co-founders, we communicated well and recognized the problems. Stakes, vesting, target markets, and approach were agreed upon.

We were behind schedule. Technical debt and strategic gap grew.

Bi-daily and weekly reviews didn't help. Each time, there were explanations. Inside, I was freaking out.

Self-reflection

I am a fairly easy person to talk to. I always try to stick to agreements; otherwise, my head gets stuffed with unnecessary information, interpretations, and emotions.

Sit down -> talk -> decide -> do -> evaluate the results. Repeat it.

If I don't get detailed comments, I start ruining everyone's mood. If there's a systematic violation of agreements without a good justification, I won't join the project or I'll end the collaboration.

What would I have done otherwise?

This is where it’s scariest to draw conclusions. Probably the most logical thing would have been not to start the project as we started it. But that was already a completely different project. So I would not have done anything differently and would have failed again.

But I drew conclusions for the future.

The lesson

First-time founders should find an adviser or team coach for a strategic session. It helps split the roles and responsibilities.

Yes, salary details ought to be mentioned in job postings. Recruiters and candidates both agree, so why doesn't it happen?

The short answer is “Unfortunately, it’s not the Recruiter’s decision”. The longer answer is well… A LOT.

Starting in November 2022, NYC employers must include salary ranges in job postings. It should have started in May, but companies balked.

I'm thrilled about salary transparency. This decision will promote fair, inclusive, and equitable hiring practices, and I'm sure other states will follow suit. Good news!

Candidates, recruiters, and ED&I practitioners have advocated for pay transparency for years. Why the opposition?

Let's quickly review why companies have trouble sharing salary bands.

💰 Pay Parity

Many companies and leaders still oppose pay parity. Yes, even in 2022.

💰 Pay Equity

Many companies believe in pay parity and have reviewed their internal processes and systems to ensure equality.

However, Pay Equity affects who gets roles/promotions/salary raises/bonuses and when. Enter the pay gap!

💰Pay Transparency and its impact on Talent Retention

Sharing salary bands with external candidates (and the world) means current employees will have access to that information, which is one of the main reasons companies don't share salary data.

If a company has Pay Parity and Pay Equity issues, they probably have a Pay Transparency policy as well.

Sharing salary information with external candidates without ensuring current employees understand their own salary bands and how promotions/raises are decided could impact talent retention strategies.

This information should help clarify recent conversations.

AI images are like funhouse mirrors.

Google's AI Blog introduced the puppy-slug in the summer of 2015.

Puppy-slug isn't a single image or character. "Puppy-slug" refers to Google's DeepDream's unsettling psychedelia. This tool uses convolutional neural networks to train models to recognize dataset entities. If researchers feed the model millions of dog pictures, the network will learn to recognize a dog.

DeepDream used neural networks to analyze and classify image data as well as generate its own images. DeepDream's early examples were created by training a convolutional network on dog images and asking it to add "dog-ness" to other images. The models analyzed images to find dog-like pixels and modified surrounding pixels to highlight them.

Puppy-slugs and other DeepDream images are ugly. Even when they don't trigger my trypophobia, they give me vertigo when my mind tries to reconcile familiar features and forms in unnatural, physically impossible arrangements. I feel like I've been poisoned by a forbidden mushroom or a noxious toad. I'm a Lovecraft character going mad from extradimensional exposure. They're gross!

Is this really how AIs see the world? This is possibly an even more unsettling topic that DeepDream raises than the blatant abjection of the images.

When these photographs originally circulated online, many friends were startled and scandalized. People imagined a computer's imagination would be literal, accurate, and boring. We didn't expect vivid hallucinations and organic-looking formations.

DeepDream's images didn't really show the machines' imaginations, at least not in the way that scared some people. DeepDream displays data visualizations. DeepDream reveals the "black box" of convolutional network training.

Some of these images look scary because the models don't "know" anything, at least not in the way we do.

These images are the result of advanced algorithms and calculators that compare pixel values. They can spot and reproduce trends from training data, but can't interpret it. If so, they'd know dogs have two eyes and one face per head. If machines can think creatively, they're keeping it quiet.

You could be forgiven for thinking otherwise, given OpenAI's Dall-impressive E's results. From a technological perspective, it's incredible.

Arthur C. Clarke once said, "Any sufficiently advanced technology is indistinguishable from magic." Dall-magic E's requires a lot of math, computer science, processing power, and research. OpenAI did a great job, and we should applaud them.

Dall-E and similar tools match words and phrases to image data to train generative models. Matching text to images requires sorting and defining the images. Untold millions of low-wage data entry workers, content creators optimizing images for SEO, and anyone who has used a Captcha to access a website make these decisions. These people could live and die without receiving credit for their work, even though the project wouldn't exist without them.

This technique produces images that are less like paintings and more like mirrors that reflect our own beliefs and ideals back at us, albeit via a very complex prism. Due to the limitations and biases that these models portray, we must exercise caution when viewing these images.

The issue was succinctly articulated by artist Mimi Onuoha in her piece "On Algorithmic Violence":

As we continue to see the rise of algorithms being used for civic, social, and cultural decision-making, it becomes that much more important that we name the reality that we are seeing. Not because it is exceptional, but because it is ubiquitous. Not because it creates new inequities, but because it has the power to cloak and amplify existing ones. Not because it is on the horizon, but because it is already here.

Successful workers don't talk this way.

"I know it's unprofessional, but I can't stop." — Author Sandy Hall

Do you realize your unprofessionalism? Do you care? Self-awareness?

Everyone can improve their unprofessionalism. Some workplace phrases and words shouldn't be said.

People often say out loud what they're thinking. They show insecurity, incompetence, and disrespect.

"Think before you speak," goes the saying.

Some of these phrases are "okay" in certain situations, but you'll lose colleagues' respect if you use them often.

Your word choice. Your tone. Your intentions. They matter.

Choose your words carefully to build work relationships and earn peer respect. You should build positive relationships with coworkers and clients.

These 10 phrases are unprofessional. 

1. That Meeting Really Sucked

Wow! Were you there? You should be responsible if you attended. You can influence every conversation.

Alternatives

Improve the meeting instead of complaining afterward. Make it more meaningful and productive.

2. Not Sure if You Saw My Last Email

Referencing a previous email irritates people. Email follow-up can be difficult. Most people get tons of emails a day, so it may have been buried, forgotten, or low priority.

Alternatives

It's okay to follow up, but be direct, short, and let the recipient "save face"

3. Any Phrase About Sex, Politics, and Religion

Discussing sex, politics, and religion at work is foolish. If you discuss these topics, you could face harassment lawsuits.

Alternatives

Keep quiet about these contentious issues. Don't touch them.

4. I Know What I’m Talking About

Adding this won't persuade others. Research, facts, and topic mastery are key to persuasion. If you're knowledgeable, you don't need to say this.

Alternatives

Please don’t say it at all. Justify your knowledge.

5. Per Our Conversation

This phrase sounds like legal language. You seem to be documenting something legally. Cold, stern, and distant. "As discussed" sounds inauthentic.

Alternatives

It was great talking with you earlier; here's what I said.

6. Curse-Word Phrases

Swearing at work is unprofessional. You never know who's listening, so be careful. A child may be at work or on a Zoom or Teams call. Workplace cursing is unacceptable.

Alternatives

Avoid adult-only words.

7. I Hope This Email Finds You Well

This is a unique way to wish someone well. This phrase isn't as sincere as the traditional one. When you talk about the email, you're impersonal.

Alternatives

Genuinely care for others.

8. I Am Really Stressed

Happy, strong, stress-managing coworkers are valued. Manage your own stress. Exercise, sleep, and eat better.

Alternatives

Everyone has stress, so manage it. Don't talk about your stress.

9. I Have Too Much to Do

You seem incompetent. People think you can't say "no" or have poor time management. If you use this phrase, you're telling others you may need to change careers.

Alternatives

Don't complain about your workload; just manage it.

10. Bad Closing Salutations

"Warmly," "best," "regards," and "warm wishes" are common email closings. This conclusion sounds impersonal. Why use "warmly" for finance's payment status?

Alternatives

Personalize the closing greeting to the message and recipient. Use "see you tomorrow" or "talk soon" as closings.

Bringing It All Together

These 10 phrases are unprofessional at work. That meeting sucked, not sure if you saw my last email, and sex, politics, and religion phrases.

Also, "I know what I'm talking about" and any curse words. Also, avoid phrases like I hope this email finds you well, I'm stressed, and I have too much to do.

Successful workers communicate positively and foster professionalism. Don't waste chances to build strong work relationships by being unprofessional.

“Unprofessionalism damages the business reputation and tarnishes the trust of society.” — Pearl Zhu, an American author

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