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.

Open to ideas or acquisitions

Failure is an unavoidable aspect of life, yet many recoil at the word.

I've worked on unrelated startup projects. This is a list of products I developed (often as the tech lead or co-founder) and why they failed to launch.

Chess Bet (Betting)

As a chess player who plays 5 games a day and has an ELO rating of 2100, I tried to design a chess engine to rival stockfish and Houdini.

While constructing my chess engine, my cofounder asked me about building a p2p chess betting app. Chess Bet. There couldn't be a better time.

Two people in different locations could play a staked game. The winner got 90% of the bet and we got 10%. The business strategy was clear, but our mini-launch was unusual.

People started employing the same cheat engines I mentioned, causing user churn and defaming our product.

It was the first programming problem I couldn't solve after building a cheat detection system based on player move strengths and prior games. Chess.com, the most famous online chess software, still suffers from this.

We decided to pivot because we needed an expensive betting license.

We relaunched as Chess MVP after deciding to focus on chess learning. A platform for teachers to create chess puzzles and teach content. Several chess students used our product, but the target market was too tiny.

We chose to quit rather than persevere or pivot.

BodaCare (Insure Tech)

‘BodaBoda’ in Swahili means Motorcycle. My Dad approached me in 2019 (when I was working for a health tech business) about establishing an Insurtech/fintech solution for motorbike riders to pay for insurance using SNPL.

We teamed up with an underwriter to market motorcycle insurance. Once they had enough premiums, they'd get an insurance sticker in the mail. We made it better by splitting the cover in two, making it more reasonable for motorcyclists struggling with lump-sum premiums.

Lack of capital and changing customer behavior forced us to close, with 100 motorcyclists paying 0.5 USD every day. Our unit econ didn't make sense, and CAC and retention capital only dug us deeper.

Circle (Social Networking)

Having learned from both product failures, I began to understand what worked and what didn't. While reading through Instagram, an idea struck me.

Suppose social media weren't virtual.

Imagine meeting someone on your way home. Like-minded person

People were excited about social occasions after covid restrictions were eased. Anything to escape. I just built a university student-popular experiences startup. Again, there couldn't be a better time.

I started the Android app. I launched it on Google Beta and oh my! 200 people joined in two days.

It works by signaling if people are in a given place and allowing users to IM in hopes of meeting up in near real-time. Playstore couldn't deploy the app despite its success in beta for unknown reasons. I appealed unsuccessfully.

My infrastructure quickly lost users because I lacked funding.

In conclusion

This essay contains many failures, some of which might have been avoided and others not, but they were crucial learning points in my startup path.

If you liked any idea, I have the source code on Github.

Happy reading until then!

I've been pondering product strategy and how to articulate it. Frameworks helped guide our thinking.

If your teams aren't working together or there's no clear path to victory, your product strategy may not be well-articulated or communicated (if you have one).

Before diving into a product strategy's details, it's important to understand its role in the bigger picture — the pieces that move your organization forward.

the overall picture

A product strategy is crucial, in my opinion. It's part of a successful product or business. It's the showpiece.

To simplify, we'll discuss four main components:

1. Vision

2. Product Management

3. Goals

4. Roadmap

Vision

Your company's mission? Your company/product in 35 years? Which headlines?

The vision defines everything your organization will do in the long term. It shows how your company impacted the world. It's your organization's rallying cry.

An ambitious but realistic vision is needed.

Without a clear vision, your product strategy may be inconsistent.

Product Management

Our main subject. Product strategy connects everything. It fulfills the vision.

In Part 2, we'll discuss product strategy.

Goals

This component can be goals, objectives, key results, targets, milestones, or whatever goal-tracking framework works best for your organization.

These product strategy metrics will help your team prioritize strategies and roadmaps.

Your company's goals should be unified. This fuels success.

Roadmap

The roadmap is your product strategy's timeline. It provides a prioritized view of your team's upcoming deliverables.

A roadmap is time-bound and includes measurable goals for your company. Your team's steps and capabilities for executing product strategy.

If your team has trouble prioritizing or defining a roadmap, your product strategy or vision is likely unclear.

Formulation of a Product Strategy

Now that we've discussed where your product strategy fits in the big picture, let's look at a framework.

A product strategy should include challenges, an approach, and actions.

Challenges

First, analyze the problems/situations you're solving. It can be customer- or company-focused.

The analysis should explain the problems and why they're important. Try to simplify the situation and identify critical aspects.

Some questions:

• What issues are we attempting to resolve?

• What obstacles—internal or otherwise—are we attempting to overcome?

• What is the opportunity, and why should we pursue it, in your opinion?

Decided Method

Second, describe your approach. This can be a set of company policies for handling the challenge. It's the overall approach to the first part's analysis.

The approach can be your company's bets, the solutions you've found, or how you'll solve the problems you've identified.

Again, these questions can help:

• What is the value that we hope to offer to our clients?

• Which market are we focusing on first?

• What makes us stand out? Our benefit over rivals?

Actions

Third, identify actions that result from your approach. Second-part actions should be these.

Coordinate these actions. You may need to add products or features to your roadmap, acquire new capabilities through partnerships, or launch new marketing campaigns. Whatever fits your challenges and strategy.

Final questions:

• What skills do we need to develop or obtain?

• What is the chosen remedy? What are the main outputs?

• What else ought to be added to our road map?

Put everything together

… and iterate!

Strategy isn't one-and-done. Changes occur. Economies change. Competitors emerge. Customer expectations change.

One unexpected event can make strategies obsolete quickly. Muscle it. Review, evaluate, and course-correct your strategies with your teams. Quarterly works. In a new or unstable industry, more often.

The brand-new USB Rubber Ducky is much riskier than before.

With its own programming language, the well-liked hacking tool may now pwn you.

With a vengeance, the USB Rubber Ducky is back.

This year's Def Con hacking conference saw the release of a new version of the well-liked hacking tool, and its author, Darren Kitchen, was on hand to explain it. We put a few of the new features to the test and discovered that the most recent version is riskier than ever.

WHAT IS IT?

The USB Rubber Ducky seems to the untrained eye to be an ordinary USB flash drive. However, when you connect it to a computer, the computer recognizes it as a USB keyboard and will accept keystroke commands from the device exactly like a person would type them in.

Kitchen explained to me, "It takes use of the trust model built in, where computers have been taught to trust a human, in that anything it types is trusted to the same degree as the user is trusted. And a computer is aware that clicks and keystrokes are how people generally connect with it.

Over ten years ago, the first Rubber Ducky was published, quickly becoming a hacker favorite (it was even featured in a Mr. Robot scene). Since then, there have been a number of small upgrades, but the most recent Rubber Ducky takes a giant step ahead with a number of new features that significantly increase its flexibility and capability.

WHERE IS ITS USE?

The options are nearly unlimited with the proper strategy.

The Rubber Ducky has already been used to launch attacks including making a phony Windows pop-up window to collect a user's login information or tricking Chrome into sending all saved passwords to an attacker's web server. However, these attacks lacked the adaptability to operate across platforms and had to be specifically designed for particular operating systems and software versions.

The nuances of DuckyScript 3.0 are described in a new manual. 

The most recent Rubber Ducky seeks to get around these restrictions. The DuckyScript programming language, which is used to construct the commands that the Rubber Ducky will enter into a target machine, receives a significant improvement with it. DuckyScript 3.0 is a feature-rich language that allows users to write functions, store variables, and apply logic flow controls, in contrast to earlier versions that were primarily limited to scripting keystroke sequences (i.e., if this... then that).

This implies that, for instance, the new Ducky can check to see if it is hooked into a Windows or Mac computer and then conditionally run code specific to each one, or it can disable itself if it has been attached to the incorrect target. In order to provide a more human effect, it can also generate pseudorandom numbers and utilize them to add a configurable delay between keystrokes.

The ability to steal data from a target computer by encoding it in binary code and transferring it through the signals intended to instruct a keyboard when the CapsLock or NumLock LEDs should light up is perhaps its most astounding feature. By using this technique, a hacker may plug it in for a brief period of time, excuse themselves by saying, "Sorry, I think that USB drive is faulty," and then take it away with all the credentials stored on it.

HOW SERIOUS IS THE RISK?

In other words, it may be a significant one, but because physical device access is required, the majority of people aren't at risk of being a target.

The 500 or so new Rubber Duckies that Hak5 brought to Def Con, according to Kitchen, were his company's most popular item at the convention, and they were all gone on the first day. It's safe to suppose that hundreds of hackers already possess one, and demand is likely to persist for some time.

Additionally, it has an online development toolkit that can be used to create attack payloads, compile them, and then load them onto the target device. A "payload hub" part of the website makes it simple for hackers to share what they've generated, and the Hak5 Discord is also busy with conversation and helpful advice. This makes it simple for users of the product to connect with a larger community.

It's too expensive for most individuals to distribute in volume, so unless your favorite cafe is renowned for being a hangout among vulnerable targets, it's doubtful that someone will leave a few of them there. To that end, if you intend to plug in a USB device that you discovered outside in a public area, pause to consider your decision.

WOULD IT WORK FOR ME?

Although the device is quite straightforward to use, there are a few things that could cause you trouble if you have no prior expertise writing or debugging code. For a while, during testing on a Mac, I was unable to get the Ducky to press the F4 key to activate the launchpad, but after forcing it to identify itself using an alternative Apple keyboard device ID, the problem was resolved.

From there, I was able to create a script that, when the Ducky was plugged in, would instantly run Chrome, open a new browser tab, and then immediately close it once more without requiring any action from the laptop user. Not bad for only a few hours of testing, and something that could be readily changed to perform duties other than reading technology news.