lessons

Embrace Risks, Execute with an Edge and Seek the Asymmetrical Upside

On Friday, October 17, 2025, Chancellor Kathleen Taylor at York University conferred on Eva Lau the degree of Doctor of Laws, honoris causa.

I purposely avoided hearing her practice so I could experience it on stage for the first time, just like everyone else in the audience.

It turned out to be the right call. By taking the risk of not previewing it, I gained an asymmetrical upside! Ironically, these are the lessons she shared. Frankly, I wish someone had told me these lessons when I was in my twenties.

Please read her remark when you have a moment:

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Dean Zwick, faculty, honoured guests, proud families, and—most importantly—the graduating class of 2025: thank you. It is a profound honour to stand before you today.

First, I want to thank the school for recognizing my work in entrepreneurship and innovation and granting me this extraordinary honour.

I also want to thank my mom and my late father, whose leap of faith to immigrate to Canada opened the doors for me and my sister to build our lives here.

To my daughters—you’ve been my biggest motivators. You are the reason I push forward, because I want you to know your potential is uncapped. You can chart your own paths and build your own successes.

And to my husband, Allen: thank you for your love, support, and affirmations. You mean the world to me, and you make me a better person every day.

And to the graduating class—congratulations! Today is a celebration of your hard work, your determination, and your costly Red Bull habits. It is my greatest joy to share a few words with you. Since we are all business school graduates, let’s get straight to business. I want to share with you a strategy—a framework, at least for me—on how to calculate risk, how to execute with an edge, and how to maximize the upside, to a point that it can be transformational. That’s right, I am putting our education to work here. No group project required!

Lesson 1: Embrace Risk—But Know Your Bottom Line

In school, we learned about Risk Management in Finance. Identify the risks. Quantify them. Mitigate them. Protect value. Very neat, very rational.

But in life, risk doesn’t come with a spreadsheet. In life, managing risk means asking: how much am I truly willing to lose? Unless you define that, you can never truly take a risk.

When people read about the success of Wattpad, the story can look deceptively simple. We built the product. Users loved it. The product went viral. And ta-da! It became one of the most iconic internet platforms in the world, serving over 100 million users worldwide, sharing over 1 million new stories in 50 languages every day. We even have TV and movie products around the world. When the company was acquired in 2021, it was one of the most significant tech exits in Canadian history.

But the “ta-da” moment was actually years of sweat, doubt, and very small numbers. At the start in 2006, Wattpad didn’t just have few users—we had so few that our total ad revenue was…two dollars. Not two million. Not two thousand. Not twenty. Just two. And Allen and Ivan, the two cofounders, had to split it. I think one bought a coffee… the other just got the receipt.

Our family’s finances? Let’s just say “tough” doesn’t quite capture it. We were running low on savings and even had to leverage our house to keep everything going. Allen and I had many long kitchen-table talks. In the end, we decided we were willing to risk everything—even selling the house—if that’s what it took. But we drew a firm line: we were willing to go down to zero, but we were not willing to go into the negatives.

That’s what embracing risk looks like for an entrepreneur. It’s not about avoiding loss. It’s about defining your boundaries and then giving it everything you’ve got. Try your hardest to stay clear of the bottom line.

And when mobile computing took off with the launch of iphones and android devices, all that persistence paid off. Wattpad became the world’s number one story-sharing app on all app stores.

We took the same approach when exploring new frontiers at Wattpad—first with AI, then with entertainment. In 2012—long before “ChatGPT” became a household name—we became one of the first companies to deploy AI at scale on a commercial platform. It was a bold move, and yes, a risky one. Then in 2016, we leapt into film and TV production—an entirely different world for us. Both were high-stakes bets, but because we had clearly defined what we were willing to invest and what we were prepared to lose, we could take those risks with confidence.

So my first lesson: embrace risk. Define your bottom line so you can move forward without fear. Knowing your worst-case scenario gives you the freedom to take that leap of faith. In your case, living in your parents’ basement could be the worst-case scenario. But hey, you already know them well enough. I think you will survive.

Lesson 2: Leverage Your Uniqueness

Once you’ve defined your risk boundaries, the next step is execution. And here’s the secret: the best execution comes from knowing what makes us unique and leaning into it.

When I began my journey as a venture capitalist a decade ago, I knew I couldn’t just be another investor. What set me apart was lived experience: I had scaled a product from a few thousand users to tens of millions. I understood the fear, the pivots, and the sleepless nights—not from theory, but firsthand.

Before Wattpad, I worked in a semiconductor company, managing a product line that was competing with a startup at the time, called Nvidia. AMD later acquired the company for US$ 4 billion. That experience gave me the technical and operational lenses very few investors had.

And then there were my learnings from some of the best investors in the world—people who backed Twitter, Coinbase, Google, and even OpenAI. I had the opportunity to learn directly from them since they were also Wattpad investors.

All of that shaped my unique edge as a venture capitalist at Two Small Fish. With a distinct investment thesis, we became one of the few deep-tech investors in Canada, backing founders tackling hard technology problems with novel innovations. Today, I’m proud to say Two Small Fish is not only among the top-performing VC funds globally, but also a firm that founders love working with—because we do things differently.

That’s the second lesson: know our uniqueness and use it. Don’t downplay it. Don’t hide it. It’s our superpower.

Lesson 3: Chase Asymmetrical Upside

The third lesson is about aiming high. Really high. Chase the Asymmetrical Upside.

Entrepreneurship and innovation are not about making something just 10-20% better. They are about creating something 100 times, 1000 times better. Something transformational.

If you only focus on small, incremental gains, you might survive—but you won’t thrive when the next wave of disruption comes. But if you go after opportunities with asymmetrical upside—where the potential payoff is massive compared to the risk—you position yourself for breakthroughs.

Take Wattpad again. If we had only wanted to build a small reading app for a niche audience, that would have been fine. But by dreaming bigger—by imagining an AI-powered global entertainment company—the outcome was transformational.

And this applies to your careers too. You won’t change industries—or the world—by playing it safe. You have to reach for opportunities that feel a little terrifying, a little out of your league.

I like to remind young entrepreneurs: I have never seen a basketball player aim for the bottom of the net. They always aim above it. That’s how slam dunks happen.

So my third lesson: don’t settle for small steps. Chase the opportunities that stretch you, the ones that scare you, the ones that could redefine everything.

So, Class of 2025, to sum these up, I encourage you to:

  • Embrace risk. Define your boundaries. Know how much you’re willing to lose, and let that clarity free you.
  • Leverage your uniqueness. Don’t try to be a knockoff of someone else. Your unique mix of experiences, skills, and quirks is your competitive edge.
  • Chase asymmetrical upside. Don’t aim for incremental change. Aim for the slam dunk.

Your journey will not be a straight line. There will be pauses, setbacks, and zigzags. But each twist is part of the story that prepares you for the next leap forward.

So step into your future with courage. Take the risk! The world doesn’t need another safe bet—it needs bold leaders, innovative thinkers, and dreamers who are willing to take the shot.

Congratulations once again, Class of 2025. The future is yours—go and dunk it.

AI’s Real Revolution Is Just Beginning

Thank you to The Globe for publishing my op-ed about AI last week. In it, I draw parallels between the dot-com crash and the current AI boom—keeping in mind the old saying, “History doesn’t repeat itself, but it often rhymes.” The piece also explores how the atomic unit of this transformation is the ever-declining “cost of intelligence.” AI is the first technology in human history capable of learning, reasoning, creativity, cross-domain thinking, and decision-making. This fundamental shift will impact every sector, without exception, spurring the rise of new tech giants and inevitable casualties in the process. The key is knowing which land to grab!

The piece is now available below.

In the past month, everyone I spoke to has been talking about DeepSeek and Nvidia. Is Nvidia facing extinction? Have certain tech giants overspent on AI? Are we seeing a bubble about to burst, or just another public market overreaction? And what about traditional sectors, like industrials, that haven’t yet felt AI’s impact?

Let’s step back. We’ll revisit companies that soared or collapsed during the dot-com crash – and the lessons we can learn. As Mark Twain reputedly said, “History doesn’t repeat itself, but it often rhymes.”

The answer is that the reports of Nvidia’s demise are greatly exaggerated, though other companies face greater danger. At the same time, new opportunities are vast because this AI-driven shift could dwarf past tech disruptions.

Before 2000, the dot-com mania hit full speed. High-flying infrastructure players such as Global Crossing – once worth US$47-billion – provided backbone networks. Cisco delivered networking equipment, and Sun Microsystems built servers. However, amid the crash, Global Crossing went bankrupt in January, 2002. Cisco plummeted from more than US$500-billion in market cap to about $100-billion. Sun Microsystems sank from a US$200-billion market cap to under US$10-billion.

They failed or shrank for different reasons. Global Crossing needed huge investments before real revenue arrived. Cisco had decent unit economics but lost pricing power when open networking standards commoditized its gear. Sun Microsystems suffered when cheaper hardware and free, open-source software (such as Linux and Apache) undercut it, and commodity hardware plus cloud computing made its servers irrelevant.

However, these companies did not decline because they were infrastructure providers. They declined because they failed to identify the right business model before their capital ran out or were disrupted by alternatives, including open or free systems, despite having the first-mover advantage.

Meanwhile, other infrastructure players thrived. Amazon, seen mostly as an e-commerce site, earned 70 per cent of its operating profit from Amazon Web Services – hosting startups and big players such as Netflix. AWS eliminated the need to buy hardware and continually cut prices, especially in its earlier years, catalyzing a new wave of businesses and ultimately driving demand while increasing AWS’s revenue.

In hindsight, the dot-com boom was real – it simply took time for usage to catch up to the hype. By the late 2000s, mobile, social and cloud surged. Internet-native giants (Netflix, Google, etc.) grew quickly with products that truly fit the medium. Early front-runners such as Yahoo! and eBay faded. Keep in mind that Facebook was founded in 2004, well after the crash, and Apple shifted from iPods to the revolutionary iPhone in 2007, which further catalyzed the internet explosion. A first-mover advantage might not always pay off.

The first lesson we learned is that open systems disrupt and commoditize infrastructure. At that time, and we are seeing it again, an army of contributors drove open systems for free, allowing them to out-innovate proprietary solutions.

Companies that compete directly against open systems – note that Nvidia does not – are particularly vulnerable at the infrastructure layer when many open and free alternatives (such as those solely building LLMs without any applications) exist. DeepSeek, for example, was inevitable – this is how technology evolves.

Open standards, open source and other open systems dramatically lower costs, reduce barriers to AI adoption and undermine incumbents’ pricing power by offering free, high-quality alternatives. This “creative destruction” drives technological progress.

In other words, OpenAI is in a vulnerable position, as it resembles the software side of Sun Microsystems – competing with free alternatives such as Linux. It also requires significant capital to build out, yet its infrastructure is rapidly becoming commoditized, much like Global Crossing’s situation. On the other hand, Nvidia has a strong portfolio of proprietary technologies with few commoditized alternatives, making its position relatively secure. Nvidia is not the new Sun Microsystems or Cisco.

Most importantly, the disruption and commoditization of infrastructure also democratize AI innovation. Until recently, starting an AI company often required raising millions – if not tens of millions – just to get off the ground. That is already changing, as numerous fast-growing companies have started and scaled with minimal initial capital. This is leading to an explosion of innovative startups and further accelerating the flywheel.

The next lesson we learned is that the internet was the first technology in human history that was borderless, connected, ubiquitous, real-time, and free. Its atomic unit is connectivity. During its rise, “the cost of connectivity” steadily declined, while productivity gains from increased connectivity continued to expand demand. The flywheel turned faster and faster, forming a virtuous cycle.

Similarly, AI is the first technology in human history capable of learning, reasoning, creativity, cross-domain functions and decision-making. Crucially, AI’s influence is no longer confined to preprogrammed software running on computing devices; it now extends into all types of machines. Hardware and software, combined with collective learning, enable autonomous cars and other systems like robots to adapt intelligently in real time with little or no predefined instructions.

These breakthroughs are reaching sectors scarcely touched by the internet revolution, including manufacturing and energy. This goes beyond simple digitization; we are entering an era of autonomous operations and, ultimately, autonomous businesses, allowing humans to focus on higher-value tasks.

As with connectivity costs in the internet era, in this AI era, “the cost of intelligence” has been steadily declining. Meanwhile, the value derived from increased intelligence continues to grow, driving further demand – this mirrors how the internet played out and is already happening again for AI. The parallels between these two platform shifts suggest that massive economic value will be created or shifted from incumbents, opening substantial investment opportunities across early-stage ventures, growth-stage private markets and public investments.

Just as the early internet boom heavily focused on infrastructure, a significant amount of capital has been invested in enabling AI technologies. However, over time, economic value shifts from infrastructure to applications – just as it did with the internet.

This doesn’t mean there are no opportunities in AI infrastructure – far from it. Remember, more than half of Amazon’s profits come from AWS. Services, such as AWS, that provide access to AI, will continue to benefit as demand soars. Similarly, Nvidia will continue to benefit from the rising demand. However, many of today’s most-valuable companies – both public and private – are in the application layer or operate full-stack models.

Despite these advancements, this transformation won’t happen overnight, but it will likely unfold more quickly than the internet disruption – which took more than a decade – because many core technologies for rapid innovation are already in place.

AI revenues might appear modest today and don’t yet show up in the public markets. However, if we look closer, some AI-native startups are already growing at an unprecedented pace. The disruption isn’t a prediction; it’s already happening.

As Bill Gates once said, “Most people overestimate what they can achieve in one year and underestimate what they can achieve in ten years.”

The AI revolution is just beginning. The next decade will bring enormous opportunities – and a new wave of tech giants, alongside inevitable casualties.

It’s a land grab – you just need to know which land to seize!

P.S. If you enjoyed this blog post, please take a minute to like, comment, subscribe and share. Thank you for reading!

This blog is licensed under a Creative Commons Attribution 4.0 International License. You are free to copy, redistribute, remix, transform, and build upon the material for any purpose, even commercially, as long as appropriate credit is given.

Contrarian Series: Your TAM is Zero? We love it!

Note: One of the most common pieces of feedback we receive from entrepreneurs is that TSF partners don’t think, act, or speak like typical VCs. The Contrarian Series is meant to demystify this, so founders know more about us before pitching.

Just before New Year, I was speaking at the TBDC Venture Day Conference together with BetaKit CEO Siri Agrell and Serial Entrepreneur and former MP Frank Baylis.

When I said “Two Small Fish love Zero TAM businesses,” I said it so matter-of-factly that the crowd was taken aback. I even saw quite a few posts on social media that said, “I can’t believe Allen Lau said it!”

Of course, any business will need to go after a non-zero TAM eventually. But hear me out.

Here’s what I did at Wattpad: I never had a “total addressable market” slide in the early days. I just said, “There are five billion people who can read and write, and I want to capture them all!”

Even when we became a scaleup, I kept the same line. I just said, “There are billions of people who can read, write, or watch our movies, and I want to capture them all!”

Naturally, some VCs tried to box me into the “publishing tool” category or other buckets they deemed appropriate. But Wattpad didn’t really fit into anything that existed at the time. Trust me, I tried to find a box I would fit in too, but none felt natural.

Why? That’s because Wattpad was a category creator. And, of course, that meant our TAM was effectively zero.

In other words, we made our own TAM.

Many of our portfolio companies are also category creators, so their decks often don’t have a TAM slide either.

Yes, any venture-backed company eventually needs a large TAM. And, of course, I don’t mean to suggest that every startup needs to be a category creator.

That said, we’re perfectly fine—in fact, sometimes we even prefer—seeing a pitch deck without a TAM slide. By definition, category creators have first-mover advantages. More importantly, category creators in a large, winner-take-all market—especially those with strong moats—tend to be extremely valuable at scale and, hence, highly investable.

So, founders, if your company is poised to create a large category, skip the TAM slide when pitching to Two Small Fish. We love it!

P.S. Don’t forget, if you have an “exit strategy” slide in your pitch deck, please remove it before pitching to us. TYSM!

This blog is licensed under a Creative Commons Attribution 4.0 International License. You are free to copy, redistribute, remix, transform, and build upon the material for any purpose, even commercially, as long as appropriate credit is given.

How We Built a Truly Global Powerhouse with 100 Million Users

Most people don’t realize just how global Wattpad’s business is. Here are a few fun facts:

• Only 25% of our 100 million users are from North America, while 25% come from LATAM, 25% from Europe, and 25% from Asia.

• Of the 50 languages on Wattpad, the most popular isn’t English—it’s Spanish. Other widely used languages include Bahasa Indonesia (10 million users) and Tagalog (6 million users), with millions more reading and writing in Italian, French, German, Portuguese, Vietnamese, and many others.

• Not only have our print books (yes, we’re a book publisher too) been New York Times bestsellers, but they’ve also hit #1 in multiple countries, including Germany and Colombia.

• #1 on Netflix globally and other streaming platforms? We’ve done that many times—including the Spanish smash hit A Través De Mi Ventana (Through My Window), which we co-produced with Netflix. Many #1-rated TV shows worldwide are based on Wattpad stories—and we co-produce them.

• #1 at the box office? We’ve achieved that in multiple countries as well.

How did we build this?

A lot of things made this happen, but I’ll highlight a few. It started on day one. Here’s a screenshot of our website when we launched in 2006.

Notice that we already supported many key languages worldwide. Why? Because only about 400 million people speak English as their first language—that’s less than 5% of the world’s population.

And we were right! The first language that took off wasn’t something we predicted—it was Vietnamese. We couldn’t have guessed that!

When the first Android phone came out (the T-Mobile G1), we were one of the first to support it. At that time, the iPhone was primarily a high-GDP country phenomenon, while low-GDP countries were dominated by $30 Android phones. When I travelled to these regions, I frequently brought back bags of inexpensive phones so our team could test and ensure our app worked on low-end devices. This allowed us to dominate globally.

When we raised growth capital, we didn’t just seek funding from Silicon Valley investors—we broadened our investor base to include backers from other countries. This helped us learn the nuances of international expansion while gaining support from investors who understood these markets.

When we launched subscriptions, we recognized that a one-size-fits-all model wouldn’t work. Some countries preferred à la carte purchases over all-you-can-read models. So, we introduced our own virtual currency, allowing users to buy content à la carte.

When we expanded into movies and TV shows, we didn’t just partner with Hollywood studios—we forged partnerships with entertainment companies across five continents. This ensured Wattpad story adaptations could be seen everywhere.

And the list goes on.

None of this happened automagically. It took years of conscious, deliberate effort. But once we built the foundation, expanding into new countries became incremental. There’s no free lunch, but it’s also not rocket science—it got easier and easier as we grew.

We built a truly global powerhouse with 100 million users.

If we could do it, you can too.

Choosing between the U.S. and international expansion is a false dichotomy—you can do both. As the world shifts toward intangible assets, building a global business is easier than ever.

Keep in mind that while the U.S. is the largest economy, it only accounts for approximately 26% of the world’s GDP. To create true optionality, not expanding globally—especially beyond the U.S.—is not an option.

Our experience in building a successful global business also allows us to help our portfolio companies scale internationally. We’ve been through the challenges of global expansion firsthand, and we actively share these insights to support the next generation of world-changing companies. Reach out to us if you want to be part of it!

P.S. This blog is licensed under a Creative Commons Attribution 4.0 International License. You are free to copy, redistribute, remix, transform, and build upon the material for any purpose, even commercially, as long as appropriate credit is given.

Only Optionality Can Make Canada Strong and Free

The tariffs are coming. We all know this isn’t really about fentanyl—only 19 kg of the U.S.’s supply comes from Canada, while close to 10,000 kg was seized at the U.S. border.

Even if we solved this tiny issue, Trump would find something else—maybe he’d complain that the snow in NYC is due to cold air from Canada and slap us with another tariff.

Trump’s playbook is simple: weaponize everything at his disposal to get what he wants.

He’s imposing tariffs on everything from us. We can debate whether to slap tariffs on orange juice or hair dryers in response, but that won’t materially change the outcome. How we react now is just noise—he holds all the leverage anyway. Canada will suffer in the short term, no matter what.

But we shouldn’t let a crisis go to waste. This is a golden opportunity to fix systemic issues that were previously near impossible to address—like interprovincial trade barriers. Yet even fixing that won’t solve the root problem.

Stepping back, the real issue is one of the first principles of leadership: Optionality.

Having alternatives always provides leverage. This principle applies broadly—not just to negotiations, but also to fundraising, supplier relationships, operations, company survival, M&A, and beyond—including leading a country.

Trump understands leverage better than most. This isn’t just about negotiation—even if we reach a deal this time, any agreement with him isn’t worth the paper it’s written on.

As a country, we are far too dependent on the U.S., and Trump knows it. Only by addressing our lack of optionality can we deal with him—and future U.S. presidents—on equal footing.

There is no quick fix. Only a new, decisive, visionary Prime Minister can guide Canada out of this mess.

The only way forward is to leverage what we do best—energy, natural resources, AI, and more—to create true optionality. As the world shifts toward intangible assets, ironically, our proximity to the U.S. is becoming less of a hindrance to diversification.

We must control our own destiny. We cannot allow any single country—U.S. or otherwise—to hold us hostage.

Only optionality can make Canada strong and free.

P.S. This blog is licensed under a Creative Commons Attribution 4.0 International License. You are free to copy, redistribute, remix, transform, and build upon the material for any purpose, even commercially, as long as appropriate credit is given.

Masterclass Series: Complete Redesign That Actually Works

Sonos replaced its CEO last week. The company faced significant backlash after launching a redesigned app earlier last year that was plagued by bugs, missing features, and connectivity issues, frustrating customers and tarnishing its reputation. This also led to layoffs, poor sales, and a significant drop in stock price.

While I usually don’t comment on companies I’m not involved with, as a long-time Sonos user, I was very frustrated that the alarm feature I had been relying on to wake me up in the morning for well over a decade disappeared overnight. There were other issues, too.

Throughout my career, I have worked on numerous redesign projects. A fiasco like this is totally avoidable. Today, I am sharing a couple of internal blog posts I wrote for my team (when I was Wattpad’s CEO) about this topic. Of course, these are just examples of the general framework I used. In practice, there are many specific details in each redesign that I helped guide the team through, as frameworks like this are like a hammer. Even the best hammer in the world is still just a hammer. The devil is in the details of how you use it.

These internal blog posts are just some of the hammers and drills in my toolbox that I use to help our portfolio CEOs navigate trade-offs and move fast without breaking things.

Happy reading through a sample of my collection of half a million words!

Note: These two posts have been mildly edited to improve readability.

Blog Post #1 – Subject: Feature Backward Compatibility

I have gone through major technology platform redesigns many times in my career. One problem that arises every single time is backward compatibility.

The reason is easy to understand: users can interact with complex products (such as Wattpad) in a million different ways. There is no way the engineering team could anticipate all the permutations.

There are two common ways to solve this problem. First, run an extensive beta program. This is what big companies like Apple and Microsoft do when they update their operating systems. This approach is also a great way to push some of the responsibility to their app developers. Even with virtually unlimited resources, crowdsourcing from app developers is still a far better approach. However, running an extensive beta program takes a lot of time and resources. Most companies can’t afford to do that.

The other approach is to roll out the changes progressively and incrementally. It is very tempting to make all the big changes at once, roll them out in one shot, and roll the dice. However, I am almost certain that it will backfire. Not only is it a frustrating experience for both users and engineers, but it also makes the project schedule much less predictable and, in most cases, causes the project to take much longer than anticipated.

Next year, when we focus on our redesign to reduce tech debt, don’t forget to set aside some time budget for these edge conditions that are so easily overlooked. Also, think about how we can roll out the changes more incrementally to minimize the negative impact on our users.

Blog Post #2 – Subject: The Reversibility and Consequentiality Framework

The other day, I spoke to the CEO of another consumer internet company. In terms of the scale of its user base, this company is much smaller than Wattpad, but we are still talking about millions of users here.

Like us, this company has been around for over a decade. Not surprisingly, technical debt has been an ongoing concern. A few years ago, the team decided to completely redesign its platform from the ground up. The redesign was a multi-year effort, and the team finally pulled back the curtain a year ago. While it is working fine now, this CEO told me that it took a few months before they fixed all the issues and reimplemented all the “missing” features because many of their users were using the product in “interesting” ways that the new version did not support.

These problems are fairly common when redesigning a new system from the ground up. In practice, it is simply impossible to take all the permutations into account, no matter how carefully you plan. However, if we mess things up, our user base is so large that it might negatively impact (or ruin!) 100 million people’s lives in the worst-case scenario.

On the flip side, over-planning could burn through a lot of unnecessary cycles.

One way or another, we should not let these challenges deter us from moving forward or even slow us down because there are many ways to mitigate potential problems. In principle, ensuring that the rollout is reversible and inconsequential is key.

The former is easy to understand: Can we roll back when things go wrong? Do we have a kill switch when updating our mobile apps? These are best practices that we have already been using.

However, at times, these best practices might not be possible. Can we reduce the consequentiality when rolling out? If the iOS app were completely redesigned, could we do it in smaller chunks, parallel-run the new and old versions at the same time, or try the new version on 0.1% of our users first? If not, could we roll out the new app in a small country first?

Again, our objective is not to avoid any problem at all costs. Our objective is to minimize (but not eliminate) the negative impact when things go wrong—not if things go wrong. Although Wattpad going dark for 100 million people for an extended period of time is not acceptable, in the spirit of speed, it is perfectly okay if we have ways to hit reverse or reduce the impact to only a small percentage of our users. These are not rocket science, but they do require a bit more thoughtfulness because our user base is so large that we can’t simply roll the dice.

P.S. This blog is licensed under a Creative Commons Attribution 4.0 International License. You are free to copy, redistribute, remix, transform, and build upon the material for any purpose, even commercially, as long as appropriate credit is given.

Naysayer

Important: Before continuing, read SRTX‘s CEO Katherine Homuth’s posts first (here and here).

Hi Katherine,

I read your blog posts about your current challenges and future plans. Originally, I planned to reply to you privately, but in the end, I decided to share my response as an open letter on my blog.

First of all, if you think I’m going to give you any advice, you’d be mistaken.

Why? Because I don’t think I’m qualified. I have never built a company that reinvented the textile industry. Unless I have “been there, done that,” you shouldn’t listen to me — even though TSF has been an investor in SRTX since the early days.

That said, there are numerous similarities between SRTX and Wattpad. One lesson I learned might be useful to you.

Both SRTX and Wattpad set out to reinvent industries that had remained largely unchanged for the past century. Wattpad raised over $100M USD and lost millions per year to build the business’s foundation — overcoming the chicken-and-egg problem — before we could monetize profitably. That had been our strategy from day one, and it was hard to explain on a spreadsheet. From the outside, it looks like it’s all wins. From the inside, we don’t know if the next leap forward will be our last.

Sound familiar? Like you mentioned, SRTX also raised well over $100M USD and lost millions of dollars to build the foundation of the business — overcoming the chicken-and-egg problem — before you could monetize profitably. That’s been your strategy from day one, and it was hard to explain on a spreadsheet. From the outside, it looks like it’s all wins. From the inside, you don’t know if the next leap forward will be your last.

When an entrepreneur is building a transformative company in an unconventional way, they will inevitably attract a lot of naysayers. These naysayers are usually missing key context (which is fine, as you don’t have to convince everyone), give unsolicited bad advice (which is uncool but typical of armchair coaches trying to look smart), and fail to recognize that there’s more than one way to build a massively successful company.

Here’s an example.

A few months after Wattpad was acquired, someone said to me:

“Congrats on your acquisition. But you could have been more capital-efficient. Compared to most B2B SaaS companies, your exit value relative to capital raised was not as high as it could be.”

WTF? He might as well have said McDonald’s generates more revenue than you.

Of course, we all know the proper benchmark is to compare Wattpad to other consumer companies like Snap, Twitter, or Facebook. In fact, Wattpad was massively more capital efficient — both on a per-user basis and an exit-value basis — than most other consumer companies at similar or larger scales. In some cases, we were ahead by an order of magnitude.

I wasn’t angry, upset, or offended by this ignorance, naivety, or arrogance because, over the years, I’ve had to deal with many naysayers — even after Wattpad’s successful exit.

Here’s the important lesson I learned:

Naysayers will always naysay.

They want to make themselves look smart.

They want to feel superior to you.

They don’t want to admit they were wrong, so they continue to naysay.

Most people don’t believe in moonshots because they can’t do what you do.

If you can use them to fire yourself up, that’s great. If not, don’t even spend a millisecond on them. Your time and energy are better spent focusing on finding a handful of new investors who believe in your vision, growing a fanbase that loves your product, and scaling your company. These are what you have been doing. The results will speak for themselves.

If anything, SRTX has de-risked so much over the years. Millions of people are already buying your unbreakable tights. It’s the best-selling tight in North America — unbreakable or not. A lot of capital has been raised, enabling your mega factory to become a reality. Major B2B partnerships have been formed to scale. New products, beyond tights, are soon to launch.

You’re very close to the top of Mount Everest. Who cares about those people who don’t dare to leave base camp?

Best,

Allen

P.S. This blog is licensed under a Creative Commons Attribution 4.0 International License. You are free to copy, redistribute, remix, transform, and build upon the material for any purpose, even commercially, as long as appropriate credit is given.

Breaking the Silence: Embracing the Emotion of Speaking Up

The month of May is Asian Heritage Month, honouring the lives and contributions of people of Asian origin.

This year, I would like to talk about one common issue among Asians—speaking up, or the lack thereof.

How often do you stop yourself from saying what needs to be said?

One of the biggest cultural differences that could hold Asians back is our tendency not to speak up. Since I was a kid, my parents and grandparents conditioned us to keep our heads down. Focus on your work, and as long as you do good work, your work will speak for itself.

This is all fine, except that in Western culture, certain behaviours are perceived as the norm. Leaders are expected to be vocal and own the stage.

I have seen firsthand very capable Asian people not getting promoted because they don’t say much. I have seen investors criticizing Asian founders for not having a take-over-the-world demeanour. In one specific example, a founder was having trouble raising capital despite the company doing really well. An existing investor (also Asian) told me privately that the main reason was that this founder didn’t act like a typical American founder.

Ouch! I instantly knew what he meant.

Speaking from my own experience, it took me decades to overcome this issue. I can’t speak for other Asian cultures, but in Hong Kong, during the era when I was growing up, parents would put masking tape on a kid’s mouth if they spoke too much. My parents never did this to me because I rarely said anything. 🙂 Even today, I have to constantly push myself to speak up. On some occasions, I still err on the side of not speaking up enough because it is still very unnatural for me. Your culture stays with you for life.

I can’t tell you exactly how to overcome this issue. To a degree, it has to come from within. You have to find your own way. For me, I kept telling myself I needed to err on the side of speaking up too much. Trust me, even with that, the end result is that on many occasions I still find myself thinking I could have spoken up more, even today. So, imagine if I didn’t give myself a little nudge. It took years of practice to overcome my own emotions. Eventually, I got used to it. Well, most of the time.

However, I don’t mean to say that it is all on Asians’ shoulders to overcome this. Asian or not, great leaders have the responsibility to create a safe environment for everyone to speak up in the first place.

Humility and kindness are great traits in Asian culture. Keep them. It is also okay to push yourself to be more vocal. The barrier is totally breakable, especially one step at a time. You just have to keep pushing. After all, speaking up is not mutually exclusive with your heritage!

P.S. This blog is licensed under a Creative Commons Attribution 4.0 International License. You are free to copy, redistribute, remix, transform, and build upon the material for any purpose, even commercially, as long as appropriate credit is given.

Everything Starts Small

It’s a situation founders know well: the agonizing wait to see if the product/service they’ve launched will take off. The reality is, it takes months and even years to find product-market-fit. And once that happens, the struggle doesn’t really end because there’s always another, more complex problem to solve. It can begin with product-market-fit then morph into customer/user acquisition and engagement and then shift to monetization. For entrepreneurs, building a business can feel like a never-ending cycle of wait-and-see. 

When we launched Wattpad 13 years ago, my co-founder Ivan and I immediately started monetizing with ads. And when I say we “immediately monetized” the site, I really mean we earned $2 in monthly ad revenue a full year later. A minuscule amount. 

When we first launched our Android app, we saw about 10 downloads in the first month. Even in 2011 when Android really started to take off our download numbers were still puny. 

Today, we see more than 60,000 Android users sign up every day and half of our daily usage comes from Android users. Our monthly advertising revenue is in the hundreds of thousands of dollars. We’re no longer talking about trivial amounts. It’s been a long road that had to start somewhere. 

‘Everything starts small’ is a valuable mantra for any entrepreneur. Look at Spotify: When it first launched in the US in 2010 it had 100,000 paid subscribers. Today, Spotify’s number of paid subscribers is about to cross the 100 million mark.

Not too long ago, we launched Paid Stories and we also introduced a subscription model called Premium at Wattpad. The numbers are still small. But they won’t stay that way forever (especially since we’ve rolled out these programs globally). As long as we keep improving, keep optimizing and keep promoting — basically, if we continue to hustle and grind as all great entrepreneurs do — the numbers will go up.

But we can’t expect a silver bullet. No single feature or no single promo or no single country launch will 10x these numbers overnight. While it’s not impossible to find a 10x growth hack, the reality is that it’s probably better to find 100 little things to grow 10%.  

My fellow entrepreneurs, please remember: Tomorrow will be better than today. The day after tomorrow will be better than tomorrow. Everything starts small.

Strategic Partners Turn Your Vision Into Reality Faster Than You Can

A few months ago, Wattpad announced a partnership with Anvil Publishing in the Philippines. Together, we’re launching Bliss Books, a new Young Adult imprint that’ll bring some of the biggest Wattpad stories and authors to bookshelves across the country. 

The news means Wattpad can realize the vision I laid out in the Master Plan much, much faster. But really, speed is just one of the values a strategic partner brings to the table.

Anvil also has deeper insights into local purchasing habits and consumer behaviour than we do. The first part of the Master Plan is to “Discover more great stories,” and we do this by leveraging our Story DNA machine learning technology and a passionate community to find unique voices and amazing stories that are validated in Tagalog. With their local insights, Anvil can corroborate our insights using their local knowledge to guarantee a successful adaptation. 

The best strategic partners also have a reputation you can piggy-back off of. Another element of the Master Plan is ‘Turn these stories into great movies, TV shows, print books, etc.,” Anvil has a reputation for publishing high-quality books, and that’s exactly what we want to do. 

Anvil is the publishing arm of the National Book Store with hundreds of bookstores. It’s established presence means we – through NBS – have the ability to distribute Wattpad books to every practically every part of the country tying into another key part of the Master Plan to “Distribute and monetize content on and off Wattpad and earn money for storytellers.” 

The Philippines is one of Wattpad’s largest markets and a very important one since its home to some of our most passionate users. Plus, when you factor in the expertise and reach of Anvil, it was an easy decision to partner with this local company who can help us continue to celebrate and reward Filipino authors and their fans. 

Entrepreneurs: if you have the ability to form a partnership with another complementary company, seize it. The strategic upside is great and may help you realize your vision faster than you ever could alone.  

How to make meetings suck less

About a year ago I read an article about Jeff Bezos’ approach to meetings at Amazon that really resonated with me. Specifically, there were three things that make meetings more effective and efficient that really stood out to me.

  1. The Two-Pizza Team Rule – According to Jeff Bezos, Amazon tries to “create teams that are no larger than can be fed by two pizzas”
  2. No PowerPoint – “No PowerPoints are used inside of Amazon,” Bezos proudly declares. “Somebody for the meeting has prepared a six-page…narratively structured memo. It has real sentences, and topic sentences, and verbs, and nouns–it’s not just bullet points.”
  3. Start with Silence – “We read those memos, silently, during the meeting,” says Bezos. “It’s like a study hall. Everybody sits around the table, and we read silently, for usually about half an hour, however long it takes us to read the document. And then we discuss it.”

Like Bezos, I’m a big believer in small group meetings. Based on my experience, it’s too difficult to have a conversation that’s relevant to most if there are more than eight people in the room.

I don’t necessarily 100% agree with no PowerPoint, though. Yes, there are times when having a narrative works better, but in some cases, bullet points can be more effective. One can’t replace the other. Use the right tool at the right time for the right people.

What I found really interesting is the study hall format. Since learning about, I’ve tried it out in multiple meetings by allocating the first 5-10 minutes (not 30 minutes as Bezos suggests) so everyone can go through the document or deck and add their questions and comments in advance of the discussion. Here’s what I observed:

The Pros

  • It ensures everyone has read the materials and the context is fresh in people’s mind (and yes, I know meeting organizers can always send materials in advance as pre-reading, but people still have to carve out time in their schedule to get it done. This is especially difficult for people who attend lots of back-to-back meetings).
  • It provides dedicated time for pre-reading that is already built into the meeting (similar to the point above)
  • It helps reduce the amount of context switching so the quality of the conversation goes up noticeably because the context is so fresh in everyone’s mind.
  • The quality of the questions improves because people don’t have to multi-task in the meeting, i.e. listen, read, absorb AND ask at the same time.

The Cons

  • It means less time to talk, especially when meetings are only 30 minutes long (but IMO, we get this time back in a way because we might have wasted those 5-10 minutes getting attendees up to speed anyway).

As you can tell, I become a fan of the study hall format, and while I recognize it doesn’t work for every type of meeting, it’s helpful when teams need to be on the same page with specific background information. That’s when spending 5-10 minutes to make sure everyone is “in the zone” is well worth it.

Incorporating the Study Hall format to your next meeting gives you time: Time for understanding; Time for extended reflection; Time for focused thinking; All of which leads to better and more effective meetings.

Attitude > Skill

The Wattpad team is growing and we’re hiring for many roles. Recently, the team was in the position of having to choose between two highly qualified candidates for a single role (a great problem to have). One applicant had more experience or skill but the other one had a better attitude.

So who did we pick? Well here’s what I told the team:

“All things equal, always choose attitude over skill and experience. Skills can be learned, but it is hard to change one’s attitude.”

Of course, all candidates need to meet certain skill-based criteria, whatever that may be. It’s hard to hire someone in finance if ‘spreadsheet’ is an unfamiliar term. It doesn’t make sense to hire an engineer who has never written a line of code before. These are somewhat facetious examples and IRL the bar would be set much, much higher, but you get the point.

Hiring a person who may be less experienced but possess the right attitude can be a worthwhile investment and a risk worth taking if you believe you can get the candidate 80% up to speed in 3 months and 100% up to speed in 6 months.

With the right attitude one can overcome any obstacles, but when people have the wrong attitude, getting them to fit into the company can be mission impossible because of the inevitable cultural clashes and teamwork disruption. It can drag down the performance of the entire team. People with positive attitudes can solve problems proactively rather than reactively. While it’s hard to quantify, they can greatly increase business velocity and team performance.

Choosing attitude over skill is a guiding principle that I have been using for many years and has served me really well!

The next time a candidate walks through your door and doesn’t exactly have the right skills or experience, ask yourself if they have the right attitude.

Masterclass Series: CEO, It’s Your Decision. Don’t Dodge

When you work at a startup, seeking advice and gaining buy-in from the broader team can help you move faster … until it becomes a crutch.

Recently, I bumped into an entrepreneur I invested in. He’s making some changes to the direction of his company, and after explaining them to me, I pointed out some of the potential issues. He immediately asked me: “So, do you want me to revert to the old plan?”

It was the wrong question to ask.

I explained to him that it doesn’t matter what I want. As CEO, with all the context, he’s the only one who can make that decision. As an investor, I’m not thinking about his business 24/7, but he is. It’s his company, and it’s his decision what he does with it (and only his decision). Investors should share their experiences and opinions, but they shouldn’t make decisions that affect the business.

Not long after, I had an investor friend contact me about one of his portfolio companies that’s going through a pretty rough patch. My friend said: “The CEO now blames the board of directors for making the wrong decision.” My ears perked up. This was a red flag and I told my friend as such.

A company’s board of directors only has one decision to make: Hire and fire the CEO. Inexperienced CEOs have a tendency to defer difficult decisions to the board or even other people in the company. It’s not uncommon to hear a newbie (or unconfident) CEO say something like “My recommendation to the board is …” This isn’t helpful. All this does is enable inexperienced board members to jump in and make decisions out of context. It’s tragic, really.

Obviously, I’m not suggesting that there is no value to be gained from consulting with your board: Every CEO has blind spots and can benefit from another perspective. But in the end, what happens in the business is always the CEOs call.

And it doesn’t always have to be the CEO who holds the ultimate decision-making ability (nor should it). I remember speaking with a senior leader at Wattpad, and the person said: “I would advise we do this …” I quickly reminded this person that they are the head of the business unit and the only person accountable for it. It was an important decision with huge implications across the company, so of course, I expected this person would engage with the broader team to think through the different scenarios and make sure all the bases were covered, but at the end of the day, the person was the leader, not an advisor.

These three conversations illustrate one critical point. Whether you’re a co-founder, CEO, technical lead, department manager or even individual contributor, you are the presumed expert in your role, so don’t dodge making tough decisions. Remember: You are not an advisor to your own job.

Don’t Be a Parasite If You Want To Be A Disruptor

I spoke with an entrepreneur whose company is building a new, disruptive product for the education sector. One of the challenges he’s facing is that none of the company’s co-founders have worked in the education sector before. He wondered if he should hire someone with some relevant experience.

Another entrepreneur friend of mine is building a tool that is catered to the public sector. The company is struggling to scale as a business. The sales process is too slow. The product is becoming too specific for one sector.

In both cases when these entrepreneurs asked for my advice, I told them: Don’t be a parasite if you want to be a disruptor.

There are so many verticals out there that still have not been fully transformed by the Internet — education, public sector, book publishing, the list goes one. But it’s extremely hard to transform any industry if you have a lot of dependencies with the old systems. You can’t think out of the box. Your sales cycle is too long. And often you end up with a product or a service that is incremental at best rather than revolutionary.

Now, there’s nothing wrong with that. In fact, a lot of people have built great businesses by providing incremental solutions like consulting services to the government. But, if you want to build something truly transformative and net-native, then you have to stay as far away from the traditional systems as possible and draw closer to your end users or customers.

If you want to create something truly game-changing and be a disruptor, you can’t begin the journey as a parasite.

Embrace tension to move even faster

As a startup scales, it’s natural for tension to creep up among different teams who are working on disparate objectives. Either of these conversations sound familiar?

“Showing users more ads can help generate more revenue, but it could also hurt engagement. Do we optimize for revenue or engagement?”

“We have a limited budget. If we spend it on A, B, and C we won’t be able to pay for X, Y, Z. What should we choose?”

The best way entrepreneurs can embrace and then ease tension among their teams is to establish a set of principles. Principles can help teams avoid indecision and move fast.

In the example above about serving ads at the expense of user engagement for instance, if the team has previously established that ad experiments can’t impact engagement by more than X%, it becomes easier for them to test different combinations of ads to drive the most revenue without negatively impacting engagement.

Establishing principles streamlines decision making, eliminates unnecessary meetings and propels the company forward. Everyone knows what to do and understands how much (or how little) leeway the team has.

Of course, there will be times when you may not have a principle to fall back on. That’s when the teams representing the conflicting priorities need to escalate the matter further and involve an arbitrator. Most times decisions are reversible and having an arbitrator can resolve issues quickly. In the world of startups, a quick decision always trumps a slow decision (or worse, no decision at all).  

Tension is natural and a sign your company is growing. But as your business grows and becomes more complex, decisions aren’t as straightforward as they used to. Creating a set of ground rules that inform your team’s priorities and outcomes can help avoid unnecessary confusion and conflict.

The other thing managers should remember

When I first became a manager, one thing that was extremely difficult for me to get used to was delegation. When an employee gets promoted to manager, and even after they realize they now have a different and distinct role, it can be hard to let go of the day-to-day work.

Why? In many cases, the person who gets promoted to a leadership or a manager position is someone who is an awesome individual contributor. To be an awesome IC, you need to be very good at getting stuff done.

But as a leader or a manager, you need to focus on asking other people to get stuff done.

You need to make sure your team is working on the right stuff to achieve desired outcomes. As a manager, you can’t do the work of other ICs – it no longer in your job description.

This is counter-intuitive and crazy hard because it is the polar opposite of what awesome ICs know so well.

Speaking from experience, when a leader does the work of an IC it can be very demotivating and become counterproductive. On the other hand, when a manager delegates the work and trusts individuals to get the job done it can be very motivating.

As a leader, you should remember that it is far better for you to focus on figuring out what your ICs should do (and why), and let the ICs figure out how to get the job done (and then, do it).

The one thing new managers forget

I first started managing people when I was 26. Four years later, I was managing a team of 30 developers. On paper, I was fantastically successful; in reality I should have fired myself.

At the time, I thought that in order to lead a team of awesome developers, I had to be an even more awesome developer. I worked frantically to write more code than anyone else not realizing that I accepted a new job the moment I was promoted – and writing code wasn’t it.

It’s something that almost all new managers forget. Being a manager isn’t a glorified version of your old job: it’s a brand new and completely different role. It requires a different skill set and attitude. As a manager, your responsibility is to ensure your team works on the right things at the right pace to deliver the right outcomes.

In my 30s, without any management or leadership training under my belt, I didn’t have a clue how to direct such a sizeable team. As a newbie manager I made mistakes and added further complexity to an already chaotic organization. It was only years later when I truly realized how my lack of leadership contributed to the chaos. I still cringe thinking about it.

I’m not proud of those mistakes, but I learned a lot from them. My biggest takeaway was that being a manager isn’t about rolling up your sleeves and working alongside your team (although there are times when this matters); it’s about understanding where your organization wants to go and deploying your team and resources to get you there.

If you’re a new manager who’s still doing the same work as before, step back and delegate. And, congratulations on your new job.

Out with the old (product features)

The new year means a fresh start. With that in mind, I urge product managers, designers, engineers and developers – anyone who helps develop a product, really – to think critically about the features they are designing. Have you thought about what features you’ll say goodbye to in January? Because killing features now means better business velocity for the rest of 2019.

As a product and its codebase grows, it is not uncommon to see an increase in technical debt. This debt may be because usage of a feature has scaled beyond its original design (you can’t expect a Toyota Corolla to reach 300 km/h no matter how many turbochargers you add) or because a feature, and subsequently it’s code, is used in more ways than originally intended (like a lawn mower turned into a snow blower – it works, but it shouldn’t). Often, technical debt accumulates because old or infrequently-used features aren’t retired.

There is a cost of removing these old features, of course, but removing features is significantly cheaper in the long-run than maintaining relic code. When you support outdated or unused features you’re also allowing security, performance and backwards compatibility issues to arise.

I remember reading an article about Evernote that claimed 90% of their features (and they have thousands of them) are used by less than 1% of their users. Eventually, the company’s velocity grounded to a halt because every simple feature update required numerous discussions across the company before the change could be implemented.

So make no mistake, it is desirable and even essential to purge old product features. Here’s how in three steps:  

  1. First identify a feature that you think should be retired. Then measure the usage of that feature. The data won’t lie. If usage is low, proceed to step two.
  2. The numbers may not tell you the whole story. Talk to some of the old-timers who have more context than you and understand why the feature existed in the first place. In many cases, you’ll be surprised by the reasons.
  3. Decide to purge, modernize or maintain the status quo. Make a decision and then execute your action plan.

Years ago, I was part of a team that dedicated six months to find bugs and purge unused features. On the surface, it seemed we were spending an inordinate amount of time and effort ‘looking in the rear-view mirror’ and not working on things that took the product forward. In reality though, those six months pushed the product much, much further ahead. By the end of it the product ran faster, the UI was cleaner because many unused features were gone, and annoying glitches were finally addressed. The app went from 1-star to 5-star in a few months without adding anything new.

It’s a good reminder: Less is more. Simple is good.

A Fast and Easy Way to Ask for Introductions

At some point in your career, someone you know will a) ask for an introduction to someone else in your network, or b) offer to make an introduction to someone they feel you should know.

Email introductions can be a double-edged sword. On one hand, obviously, they can be incredibly useful. On the other hand, they can suck up a lot of time if not done properly.

The very worst email introductions automatically assume that the connection being made is appropriate and beneficial for the involved parties. But the truth is, unless you’ve explicitly asked in advance, this is just an assumption.

Here’s an example of an email I recently received:

Hey Allen,

I would like to introduce you to Cindy Lou (cc’ed). Cindy Lou is an expert in X, which you will find useful. I’m sure you would enjoy the meeting. I’ll let you two find the best time to meet next week!

Cheers,
Horton

The problem is, while Cindy Lou might be an expert in X, I don’t really care about X; it’s just not my thing. Naturally, I don’t want to spend even more time feigning interest in X. And I definitely don’t want to waste Cindy Lou’s time either. The other problem: Despite what Horton thinks, I’m mostly out of the office next month, so I can’t find a time to meet without a lot of calendar shuffling.

I used to accept blind introductions (and subsequent meetings) like these out of politeness. It was an ineffective use of my time – and theirs. Even when I dared to say no, I had to spend time crafting a firm yet polite email to decline the opportunity. Drafting the email didn’t take up nearly as much time as a meeting would, but it still took time out of my day that could be better spent on other challenges. Eventually, it became too much.

Nowadays, when people ask me to connect them with someone in my network, I make sure I have a double opt-in. This means I’ve asked for—and received—the permission of both parties before I send a note. Here’s what it looks like:

Pavel would like me to connect him with John.

I’ll ask Pavel to send me a new, well-written email with the request (Pavel should NOT include our previous conversation i.e., the original request). It could look something like this.

Hey Allen,

As discussed, it would be great if you could introduce me to John. Here is a summary of my ask: <insert awesome summary here>

Thanks in advance for your help.

Live long and prosper,
Pavel

Then, I would add a sentence or two before forwarding the note to John (without including Pavel). My addition would provide further context and could be something along the lines of: “I don’t know Pavel well, and I haven’t tried his products, but the elevator pitch sounds relevant to you” or “Pavel is brilliant and working on a super interesting project you might be interested in.” This context setting is important, but should only take 30 seconds of your time.

If John agrees to the introduction, then I add Pavel to the thread. If he says no, I’ll let Pavel know that as well.

Double opt-in email introductions work well for a number of reasons.

  1. The onus is on the person requesting the introduction to write an awesome email detailing why the connection is valuable. It’s not the facilitator’s responsibility to make the case.
  2. It avoids putting people in an awkward position of accepting a connection or meeting when there is zero interest in the product/service/pitch.
  3. It encourages frank dialogue. If a person wants to decline an introduction, chances are he/she is more likely to provide a candid reason in a private one-on-one email with a trusted connection. It allows the facilitator to filter the information appropriately while still providing a truthful explanation to the requester.
  4. It allows for brevity without sounding cold. Since the facilitator has established relationships with both parties, a to-the-point email doesn’t come off as arrogant or rude.

One more thing—please don’t write the email as though it came from me. Each person has a unique writing style and voice, and I have mine, too. You won’t be able to capture my voice exactly.

I make lots of introductions, and I am more than happy to do so. It’s great for community building. I hope the double opt-in method helps make introductions faster and a better experience for everyone!

The End of 8-Hour Days

Both my parents used to work for a bank. For them, the work day started at nine in the morning and ended at 5:00 pm sharp. Day in and day out, this was their routine. They never understood the concept of flexible hours. They questioned why I would bring “work” home. On the other hand, they were always amused that I never needed to take time off work to see the doctor or get the car fixed during office hours.

“Am I expected to work an 8-hour day?” I get this question from employees from time to time, but I believe this is the wrong question to ask. Employees are expected to get their work done, deliver on OKRs and contribute to a positive workplace culture. For the most part, I don’t (and neither should their direct manager) care where or how the work gets done. Of course, it goes without saying (but I’ll still say it), flexible work hours should never impact collaboration or attendance at critical meetings.

Startups are fast-paced, ever-changing environments filled with bright employees. They’re solving complex and fascinating problems and it’s all very exciting. Being a disruptor and part of a paradigm shift is thrilling and the work itself should compel employees to give 100%. Offering flexible hours instills trust in your team and gives employees a sense of ownership to execute on projects in the way that works for them.

That’s not to say there will be no instances when burning the midnight oil for a specific project or tight deadline is required. Make no mistake, there will be times when a critical security issue needs to be addressed after-hours or a client has an urgent need on the weekend. But there should also be opportunities to take it easy and spend a few weeks out of the country or deal with a family or health issue. It’s about flexibility.

Most startups offer flexible hours, and it makes sense. After all, tech is a creative industry unlike working at a bank or factory. As people head back to work after their relaxing summer vacations, my advice to founders and startup execs? Measure productivity by outcomes and results, not timecards.

Your Next Summer Challenge: A Digital Detox

I love gadgets. They surround me everywhere – in the office, in the car, at home. I’m always connected … except when I go completely off the grid.

Twice a year I unplug for 2-3 weeks. I turn off my data. I don’t reply to email. I stay off social media. I take a break from being an entrepreneur and focus on being a husband and a dad.

It’s during these weeks when I’m unplugged that I have an opportunity to reflect on the past challenges and think about future opportunities. Going off the grid gives me a sense of clarity and enables a freedom of thinking I can’t achieve when I’m constantly pulled in multiple digital directions.

Case in point: I recently spent three weeks in Asia with my family. While I’ve traveled throughout the region extensively for work, this was the first time I could experience cities like Taipei and Shanghai as a tourist. I got to enjoy a ride on the fastest train in the world, eat the most delicious food, and shop like the locals do. I observed, indulged and enjoyed without the need to constantly check my devices. And while I was technically off-the-grid and not working, my offline experiences provided me with inspirations I will take back to the office.   

Building a business is hard. Entrepreneurs have infinite to-do lists. They are constantly pushing ahead through one challenge to seize the next opportunity. While the line between work and personal life is becoming more blurry (especially when you’re scaling a startup), it’s critical that entrepreneurs carve time out of their hectic schedules and go offline. A digital detox – even for a short period of time – yields tremendous business and personal benefits.  

If you still have a summer vacation planned,  I challenge you to use your time to explore, discover and connect IRL.

The Evolution of an Entrepreneur

Years ago, a summer job gave me one of the most valuable lessons in entrepreneurship.

I needed tuition money for university so I got a job at a factory printing t-shirts. I witnessed firsthand how the owner juggled multiple and often diverse tasks in order to operate a successful business. Looking back, I was naive to think that a t-shirt printing company was just about printing t-shirts.

If you look at the journey of an entrepreneur, it all starts with an idea. But an idea is just that – a thought. Without execution, an idea is as good as yesterday’s newspaper. Only when execution follows an idea, can you determine if there’s product-market fit. If you achieve product-market fit – congratulations, that’s a major accomplishment! You can start a company to further iterate on the idea and cement your place in the market. But once you start a company, you have to turn it into a business.

I’ve personally gone through this journey three times. My first business failed, I sold the second one, and the third has become one of Canada’s most successful startups. My experiences failing and succeeding as an entrepreneur reinforced the lesson I learned that summer many years ago: As an entrepreneur, the best product you can build is yourself.

You will wear many hats throughout the entrepreneur journey. As your company grows, you play different roles in the company and you can expect to change ‘jobs’ every few months. Each new job requires a different skill set. You may start as the product designer, but soon you’ll lead a team as a manager, and then eventually you transition into a leadership role.  I have yet to meet a single person who, at the launch of their company, has every required skill. So welcome continuous learning and crave self-improvement.

Taking the time to build yourself as a well-rounded entrepreneur will pay dividends.