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.

A fascinating business conversation.

This week at Web Summit, I had mentor hour.

Mentor hour connects startups with experienced entrepreneurs.

The YC-selected founder who mentored me had grown his company to $100 million in 18 months.

I had 45 minutes to question him.

I've compiled this.

Context

Founder's name is Zack.

After working in private equity, Zack opted to acquire an MBA.

Surrounded by entrepreneurs at a prominent school, he decided to become one himself.

Unsure how to proceed, he bet on two horses.

On one side, he received an offer from folks who needed help running their startup owing to lack of time. On the other hand, he had an idea for a SaaS to start himself.

He just needed to validate it.

Validating

Since Zack's proposal helped companies, he contacted university entrepreneurs for comments.

He contacted university founders.

Once he knew he'd correctly identified the problem and that people were willing to pay to address it, he started developing.

He earned $100k in a university entrepreneurship competition.

His plan was evident by then.

The other startup's founders saw his potential and granted him $400k to launch his own SaaS.

Hiring

He started looking for a tech co-founder because he lacked IT skills.

He interviewed dozens and picked the finest.

As he didn't want to wait for his program to be ready, he contacted hundreds of potential clients and got 15 letters of intent promising they'd join up when it was available.

YC accepted him by then.

He had enough positive signals to raise.

Raising

He didn't say how many VCs he called, but he indicated 50 were interested.

He jammed meetings into two weeks to generate pressure and encourage them to invest.

Seed raise: $11 million.

Selling

His objective was to contact as many entrepreneurs as possible to promote his product.

He first contacted startups by scraping CrunchBase data.

Once he had more money, he started targeting companies with ZoomInfo.

His VC urged him not to hire salespeople until he closed 50 clients himself.

He closed 100 and hired a CRO through a headhunter.

Scaling

Three persons started the business.

1. He primarily works in sales.

2. Coding the product was done by his co-founder.

3. Another person performing operational duties.

He regretted recruiting the third co-founder, who was ineffective (could have hired an employee instead).

He wanted his company to be big, so he hired two young marketing people from a competing company.

After validating several marketing channels, he chose PR.

$100 Million and under

He developed a sales team and now employs 30 individuals.

He raised a $100 million Series A.

Additionally, he stated

• He’s been rejected a lot. Like, a lot.

• Two great books to read: Steve Jobs by Isaacson, and Why Startups Fail by Tom Eisenmann.

• The best skill to learn for non-tech founders is “telling stories”, which means sales. A founder’s main job is to convince: co-founders, employees, investors, and customers. Learn code, or learn sales.

Conclusion

I often read about these stories but hardly take them seriously.

Zack was amazing.

Three things about him stand out:

1. His vision. He possessed a certain amount of fire.

2. His vitality. The man had a lot of enthusiasm and spoke quickly and decisively. He takes no chances and pushes the envelope in all he does.

3. His Rolex.

He didn't do all this in 18 months.

Not really.

He couldn't launch his company without private equity experience.

These accounts disregard entrepreneurs' original knowledge.

Hormozi will tell you how he founded Gym Launch, but he won't tell you how he had a gym first, how he worked at uni to pay for his gym, or how he went to the gym and learnt about fitness, which gave him the idea to open his own.

Nobody knows nothing. If you scale quickly, it's probable because you gained information early.

Lincoln said, "Give me six hours to chop down a tree, and I'll spend four sharpening the axe."

Sharper axes cut trees faster.

People-first update.

Every Google upgrade causes website owners to panic.

Some have just recovered from previous algorithm tweaks and resumed content development.

If you follow Google's Webmaster rules, you shouldn't fear its adjustments.

Everyone has a view of them. Miscommunication and confusion result.

Now, for some (hopefully) exciting news.

Google tweeted on August 18, 2022 about a fresh content update.

This change is another Google effort to remove low-quality, repetitive, and AI-generated content.

The algorithm generates and analyzes search results, not humans.

Google spends a lot to teach its algorithm what searchers want. Intent isn't always clear.

Google's content update aims to:

“… ensure people see more original, helpful content written by people, for people, in search results.”

Isn't it a noble goal?

However, what does it mean for content creators and website owners?

How can you ensure you’re creating content that will be successful after the updates roll out?

Let's first define people-first content.

What does "people-first-content" mean?

If asked, I'd say information written to answer queries and solve problems.

Like others, I read it from the term.

Content creators and marketers disagree. They need more information to follow recommendations.

Google gives explicit instructions for creating people-first content.

According to Google, if you answer yes to the following questions, you have a people-first attitude.

1. Do you have customers who might find your content useful if they contacted you directly?

2. Does your content show the breadth of your knowledge?

3. Do you have a niche or a focus for your website?

4. After reading your content, will readers learn something new to aid them in achieving their goals?

5. Are readers happy after reading your content?

6. Have you been adhering to Google's fundamental updates and product reviews?

As an SEO writer, I'm not scared.

I’ve been following these rules consciously while creating content for my website. That’s why it’s been steadily growing despite me publishing just one or two stories a month.

If you avoid AI-generated text and redundant, shallow material, your website won't suffer.

If you use unscrupulous methods to boost your website's traffic, including link buying or keyword stuffing, stop. Google is getting smarter and will find and punish your site eventually.

For those who say, “SEO is no longer working,” I dedicated the whole paragraph below.

This does not imply that SEO is obsolete.

Google:

“People-first content creators focus on creating satisfying content, while also utilizing SEO best practices to bring searchers additional value.”

The official helpful content update page lists two people-first content components:

• meeting user needs

• best practices for SEO

Always read official guidelines, not unsolicited suggestions.

SEO will work till search engines die.

How to use the update

Google said the changes will arrive in August 2022.

They pledged to post updates on Google's search ranking updates page.

Google also tweets this info. If you haven't followed it already, I recommend it.

Ranking adjustments could take two weeks and will affect English searches internationally initially.

Google affirmed plans to extend to other languages.

If you own a website, monitor your rankings and traffic to see if it's affected.

Generative AI hype: some thoughts

The sudden surge in "generative AI" startups and projects feels like the inverse of the recent "web3" boom. Both came from hyped-up pots. But while web3 hyped idealistic tech and an easy way to make money, generative AI hypes unsettling tech and questions whether it can be used to make money.

Web3 is technology looking for problems to solve, while generative AI is technology creating almost too many solutions. Web3 has been evangelists trying to solve old problems with new technology. As Generative AI evolves, users are resolving old problems in stunning new ways.

It's a jab at web3, but it's true. Web3's hype, including crypto, was unhealthy. Always expected a tech crash and shakeout. Tech that won't look like "web3" but will enhance "web2"

But that doesn't mean AI hype is healthy. There'll be plenty of bullshit here, too. As moths to a flame, hype attracts charlatans. Again, the difference is the different starting point. People want to use it. Try it.

With the beta launch of Dall-E 2 earlier this year, a new class of consumer product took off. Midjourney followed suit (despite having to jump through the Discord server hoops). Twelve more generative art projects. Lensa, Prisma Labs' generative AI self-portrait project, may have topped the hype (a startup which has actually been going after this general space for quite a while). This week, ChatGPT went off-topic.

This has a "fake-it-till-you-make-it" vibe. We give these projects too much credit because they create easy illusions. This also unlocks new forms of creativity. And faith in new possibilities.

As a user, it's thrilling. We're just getting started. These projects are not only fun to play with, but each week brings a new breakthrough. As an investor, it's all happening so fast, with so much hype (and ethical and societal questions), that no one knows how it will turn out. Web3's demand won't be the issue. Too much demand may cause servers to melt down, sending costs soaring. Companies will try to mix rapidly evolving tech to meet user demand and create businesses. Frustratingly difficult.

Anyway, I wanted an excuse to post some Lensa selfies.

These are really weird. I recognize them as me or a version of me, but I have no memory of them being taken. It's surreal, out-of-body. Uncanny Valley.

Unlimited everything for $19 monthly!?

Even with pretty words, no one wants to read an ugly email.

• Not Gen Z

• Not Millennials

• Not Gen X

• Not Boomers

I am a minimalist.

I like Mozart. I like avos. I love Apple.

When I hear seamlessly, effortlessly, or Apple's new adverb fluidly, my toes curl.

No email marketing tool gave me that feeling.

As a marketing consultant helping high-growth brands create marketing that doesn't feel like marketing, I've worked with every email marketing platform imaginable, including that naughty monkey and the expensive platform whose sales teams don't stop calling.

Most email marketing platforms are flawed.

1. They are overpriced.

2. They use dreadful templates.

3. They employ a poor visual designer.

4. The user experience there is awful.

5. Too many useless buttons are present. (Similar to the TV remote!)

I may have finally found the perfect email marketing tool. It creates strong flows. It helps me focus on storytelling.

It’s called Flodesk.

It’s effortless. It’s seamless. It’s fluid.

Here’s why it excites me.

Unlimited everything for $19 per month

Sends unlimited. Emails unlimited. Signups unlimited.

Most email platforms penalize success.

Pay for performance?

• $87 for 10k contacts

• $605 for 100K contacts

• $1,300+ for 200K contacts

In the 1990s, this made sense, but not now. It reminds me of when ISPs capped internet usage at 5 GB per month.

Flodesk made unlimited email for a low price a reality. Affordable, attractive email marketing isn't just for big companies.

Flodesk doesn't penalize you for growing your list. Price stays the same as lists grow.

Flodesk plans cost $38 per month, but I'll give you a 30-day trial for $19.

Amazingly strong flows

Foster different people's flows.

Email marketing isn't one-size-fits-all.

Different times require different emails.

People don't open emails because they're irrelevant, in my experience. A colder audience needs a nurturing sequence.

Flodesk automates your email funnels so top-funnel prospects fall in love with your brand and values before mid- and bottom-funnel email flows nudge them to take action.

I wish I could save more custom audience fields to further customize the experience.

Dynamic editor

Easy. Effortless.

Flodesk's editor is Apple-like.

You understand how it works almost instantly.

Like many Apple products, it's intentionally limited. No distractions. You can focus on emotional email writing.

Flodesk's inability to add inline HTML to emails is my biggest issue with larger projects. I wish I could upload HTML emails.

Simple sign-up procedures

Dream up joining.

I like how easy it is to create conversion-focused landing pages. Linkly lets you easily create 5 landing pages and A/B test messaging.

I like that you can use signup forms to ask people what they're interested in so they get relevant emails instead of mindless mass emails nobody opens.

I love how easy it is to embed in-line on a website.

Wonderful designer templates

Beautiful, connecting emails.

Flodesk has calm email templates. My designer's eye felt at rest when I received plain text emails with big impacts.

As a typography nerd, I love Flodesk's handpicked designer fonts. It gives emails a designer feel that is hard to replicate on other platforms without coding and custom font licenses.

Small adjustments can have a big impact

Details matter.

Flodesk remembers your brand colors. Flodesk automatically adds your logo and social handles to emails after signup.

Flodesk uses Zapier. This lets you send emails based on a user's action.

A bad live chat can trigger a series of emails to win back a customer.

Flodesk isn't for everyone.

Flodesk is great for Apple users like me.