leadership

Geopolitics Now Matters to Every CEO

In October, at our Two Small Fish Ventures AGM, I had the chance to sit down with Benjamin Bergen for a fireside chat. At the time, he was still leading the Council of Canadian Innovators. None of us knew he would soon become the new CEO of the CVCA. Looking back, the timing could not have been better.

I have known Benjamin for many years. When I was CEO of Wattpad, I worked closely with him through CCI, which played an important role in advocating for Canadian scaleups. That experience gave me a front row view of how policy, talent mobility, capital, and global markets intersect. I did not expect that perspective to become even more useful on the investor side, but today it is proving to be exactly that.

At Two Small Fish, our portfolio founders often hear us talk about our full cycle view of company building. We have built companies, operated them at global scale, navigated regulatory and geopolitical realities, and now invest across deep tech. We have seen the journey from the very first product decision all the way to commercialization. That experience matters today because geopolitics is no longer something happening far away. It is showing up directly in the work of founders.

The World Has Changed Irreversibly

Founders do not necessarily always think about politics, especially geopolitics. I certainly did not in my early days as a founder. But over the past year, the global environment has shifted in ways that affect talent, capital, customers, supply chains, and data. These forces are becoming part of the operating conditions for every innovative company.

At the AGM, Benjamin and I spent time unpacking what this new reality looks like.

  • Talent We spoke about the growing brain drain and how global mobility is changing. The tightening of the H1B program in the United States has created a ripple effect across the entire talent ecosystem. Early stage companies are rethinking where they build teams, and immigration policy is becoming a strategic consideration rather than an afterthought.
  • Capital The rise of protectionism and shifting global alliances are affecting how and where capital can move. The changing dynamics among the United States, China, and Canada raise new questions for both founders and investors. Some are beginning to view geographic diversification as a practical response to political uncertainty.
  • Customers National preference policies such as Buy Canadian and Buy American are becoming more common. These policies may begin as political statements, but they influence real procurement and partnership decisions. For founders, gaining early customers is no longer just about product and timing. There is a political dimension that needs to be understood.
  • Infrastructure and Defense We also talked about how export controls and security requirements are expanding. Technologies that once seemed purely commercial are now viewed through a strategic lens. Even young companies are discovering that they may be operating in areas that governments consider sensitive.
  • Supply Chains Global supply chains have shown their fragility in areas such as semiconductors, rare earth materials, and energy. These vulnerabilities create friction but also open new opportunities for companies building more resilient and regional alternatives.
  • Data Sovereignty Data localization and national data governance rules continue to spread. More countries want their data stored and processed within their borders. For companies operating internationally, this introduces new architectural and operational decisions much earlier in the journey.

Benjamin also shared how CCI’s new advisory group, Signa Strategies, is helping founders navigate exactly these types of challenges. It felt like a natural evolution of the work he has been doing for years.

As our conversation wrapped up, I was reminded how valuable it is to have seen this ecosystem from both sides. As a founder, I saw how talent, markets, and policy could quietly redirect a company’s path. Through CCI, I saw how national priorities and regulation shape the environment innovators work in. These experiences feel especially relevant now. The geopolitical questions that once appeared at the edges are moving closer to the center.

This is the environment founders are building in today. And with our full cycle experience, we hope to help them navigate it with clarity, context, and confidence.

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.

Reflections from the Impact 2025 Summit

I had the opportunity to join a panel at the Impact 2025 Summit in Calgary, moderated by Raissa Espiritu, with Janet Bannister and Paul Godman. Ironically, none of us are labelled as impact investors, and I explained on stage why Two Small Fish Ventures does what we do.

At Two Small Fish Ventures, we’ve never called ourselves an impact fund. That’s not because we’re indifferent to impact; in fact, it’s core to what we do. Our focus is on deep tech, the next frontier of computing, where innovation can create meaningful, long-term change. Specifically, we invest in five key areas: Vertical AI Platforms, Physical AI, AI Infrastructure, Advanced Computing Hardware, and Smart Energy.

We care deeply about scientific advancement, and more importantly, about turning those breakthroughs into real-world impact. That’s how meaningful progress happens.

Eva is our General Partner, and both of us are immigrants. Diversity isn’t a marketing point for us; it’s part of who we are. It naturally shows up in our portfolio: about half of our companies have at least one female founder, and many come from underrepresented backgrounds. That said, uncompromisingly, we back amazing deep tech founders who are turning their creations into world-class companies.

It’s actually rare that we talk about topics like women investing or investing in underrepresented groups in isolation. Not because we don’t care, quite the opposite. The fact that Eva is one of the few female GPs leading a venture fund, and that we’re both immigrants, already says a lot. Our actions speak volumes. We walk the walk and talk the talk.

We need to deliver results. Period. Our competition isn’t other venture funds; it’s every other investment opportunity available in the market. If we can’t perform at the highest level — top decile in everything we do — we can’t sustain our mission. Delivering some of the best results in the industry enables us to do what we love and make an impact.

That’s why I believe impact and performance are not opposites. The most powerful kind of impact happens when companies succeed, when they become world-class companies. Strong returns and meaningful impact can, and should, reinforce each other.

I also talked about the importance of choosing the right vehicle for the right purpose. When we made a 2 million dollar donation to the University of Toronto to establish the Commercialization Catalyst Prize, it wasn’t about investing. It was about supporting a different kind of impact — helping scientists and engineers turn their research into innovations that can reach the world. Not every kind of impact should come from the same tool.

At the end of the day, labels matter less than intent and execution. We don’t need to call ourselves an impact fund to make a difference. Our goal is simple: to back bold deep tech founders using science and technology to build a better future and to do it with excellence.

A big thank you to Raissa, George Damian, Sylvia Wang, and the entire Platform Calgary team for putting together such a thoughtful and well-run event.

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.

Masterclass Series: The Rule of 3 and 10 — Lessons I Wish I Learned Earlier

One of the most powerful frameworks I’ve come across is the Rule of 3 and 10, coined by Hiroshi Mikitani-san, founder and CEO of Rakuten. The idea is simple: every time a company triples in size, everything breaks.

As Rakuten grew from a handful of people into a global business, Mikitani-san noticed a clear pattern. At each stage — 1 to 3 people, 3 to 10, 10 to 30, 30 to 100, 100 to 300, and beyond — what worked before suddenly stopped working. And by everything, it really does mean everything: payroll, meetings, communication, budgeting, sales, even the org chart. The challenge is that many leaders blow right through these milestones without realizing what’s happening until it’s already broken.

What I Wish I Knew

I’ve been part of many really fast-growing companies — first as an employee, and later as a co-founder in two of them. And I can tell you, this rule is 100% true.

At Wattpad, I didn’t fully internalize it until we were approaching 100 people. By then, we had already missed natural breaking points where we could have rebuilt earlier. That lag made scaling harder than it needed to be.

Looking back, the stages feel something like this:

  • At 3 people, you’re a tight-knit unit where everyone knows everything.
  • At 10, you need to change how you communicate just to stay aligned.
  • At 30, the days of everyone reporting to the CEO are long gone — a first layer of leaders emerges.
  • At 100, there are layers of layers of leaders, and even well-designed systems need rethinking.
  • At 300, you’re running a completely different company than the one you started.
  • At 1,000, it feels like a mini-society with its own subcultures, bureaucracy, and politics — alignment becomes the hardest problem of all.

The Employee’s View

Before becoming an entrepreneur, I lived through this as an employee too. The breaking points are just as visible from the inside.

As companies scale, it gets harder to push things through. Meetings multiply, but decisions slow. Bystander problems appear — more people in the room, but fewer actually taking ownership. From the employee’s perspective, it feels frustrating and inefficient. But it’s not about capability; it’s about systems that no longer fit the size of the company.

Why This Matters

In the moment, it can feel like failure. But it isn’t. It’s simply that scale changes everything.

The good news: these challenges are solvable. Every growing company has faced them. The bad news: if you only react after things break, you’ll always be catching up instead of leading.

My Takeaway

If you’re building a fast-growing company, expect everything to break at 3, 10, 30, 100, 300, 1,000… and plan for it.

Don’t see it as failure. See it as evolution. Each breakdown is proof you’ve unlocked a new stage of growth. The chaos is part of the privilege — it means you’re building something worth scaling.

If I could go back and tell my younger CEO self one thing, it would be this: anticipate the breaks before they happen. Build a culture that embraces reinvention at every stage. You’ll save yourself and your team a lot of unnecessary pain — and you’ll enjoy the ride more.

P.S. The banner is using Ideogram Character to generate. It rocks!

P.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.

A Thought for Asian Heritage Month

I recently spent a few weeks in Asia, visiting Tokyo, Hong Kong, Singapore, and Taiwan before returning to Toronto. Eva joined me for the first part of the journey, while I spent time in Singapore on my own, a city I’ve visited numerous times before. In Taiwan, I was accompanied by Albert, who was born there and still has family ties in the region.

This was by far my longest trip in quite some time. These destinations represent some of the world’s most developed economies, with GDP per capita levels comparable to or exceeding those in North America. Singapore, for instance, has a per capita GDP of around 90,000 USD, roughly 50 percent higher than the United States’ 66,000 USD.

Conversations and Perspectives

Coincidentally, my visit aligned with Liberation Day. Needless to say, it sparked many fascinating conversations, including the so-called “penguin tariffs,” whether AI is already smarter than certain politicians, and everything in between. Around that time, I also came across a perspective that stood out. While tariffs were initially expected to threaten Asian economies, many locals believed they had ended up affecting the United States more. Businesses in the Asia Pacific region had begun diversifying away from reliance on the US market years ago. As a result, they now have more leverage, and the direct impact of tariffs has been relatively limited. The broader concern was the possibility of a global recession.

Tech Energy in the Region

Across all four regions, I witnessed growing momentum in tech entrepreneurship. I had the chance to speak at tech conferences, lead masterclasses, take part in fireside chats, and encourage high school students to consider entrepreneurship as a path worth exploring.

Why It’s Happening

Why is this happening? These regions have strong technical capabilities. Taiwan, for example, manufactures about 90 percent of the world’s most advanced chips, and its capabilities are unmatched by any other country. Singapore, on the other hand, excels in semiconductor fabrication and biotechnology, and its presence in AI and computing infrastructure continues to grow.

Understanding the Cultural Landscape

At the same time, the cultural differences between East and West remain clear. The East tends to emphasize social harmony, collective behaviour, and conformity. The West often puts more weight on individual expression and free spirit.

Even small things reflect these differences. Take jaywalking. In Tokyo and Singapore, it is rare. People stare at you if you do it. In contrast, after jaywalking was recently legalized in New York City, I actually felt social pressure to jaywalk. Not doing so made me feel out of place.

Why Culture Matters in Business

For companies working across borders, recognizing these kinds of cultural nuances is not optional. It is essential. A one-size-fits-all approach often leads to missteps.

The Bicultural Perspective

Having been raised in Asia and now living in Canada for decades, I’ve come to appreciate the value of navigating both worlds. That dual perspective has become a quiet but important asset in both my personal and professional life. It is not a liability.

As I often say:

“Bamboo is neutral. If it’s used as a ceiling, it becomes a barrier. But if it’s used as a pole for jumping, one can leap incredibly high. Biculturalism is a powerful asset. If you leverage it in the right context, it can become your unfair advantage.”

Biculturalism, when used with intention, becomes a meaningful advantage. It helps you understand nuance, communicate across different environments, and approach global opportunities with more adaptability.

Looking Ahead

In an increasingly interconnected world, going global is no longer just a choice. During Asian Heritage Month, this feels especially relevant. Let’s celebrate not only our roots but also the advantages that come from navigating multiple worlds.

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.

Perhaps My Title Should Be…Yoda?

Yesterday was Star Wars Day — aka “May the Fourth be with you” — and it got me thinking, so I put together this blog post.

You might notice my title is “Operating Partner,” not “General Partner,” “Managing Partner,” or “Board Partner.” That’s intentional because I spend most of my time working directly with portfolio CEOs.

The Operating Partner role has its roots in private equity. Historically, Operating Partners are often former CEOs or COOs who use their experience to guide leadership teams, improve operational execution, and drive results, ultimately increasing the value of portfolio companies.

As far as I know, I’m the only former scale-up CEO in Canada who plays this role in an early-stage VC. At least, ChatGPT and Perplexity couldn’t find anyone else! Even in the U.S., this is very rare.

That said, I’ve always felt the “Operating Partner” title is a bit misleading. Unlike many private equity Operating Partners, I don’t step into full-time or part-time leadership roles within portfolio companies. I don’t give advice or directives either. Instead, I help CEOs solve their own problems rather than solving problems for them.

My single objective is to help portfolio CEOs improve the quality of their decisions by leveraging my experience.

Why? Most CEOs don’t need to be told what to do—they already know. Telling a CEO to grow their KPIs faster or hire great people is useless.

No CEO intentionally grows slower or hires bad people!

The real challenge for CEOs isn’t the what—it’s the how. This is where I come in, helping them navigate the how: strategic thinking, future-proofing, and decision-making that drive tangible progress, while staying alert to blind spots that could undermine success.

Hiring is an example. Many venture firms have talent partners who assist portfolio companies with recruitment. These partners, often from recruitment backgrounds, are excellent at sourcing candidates once roles are defined. However, they usually lack deep business context and may not fully understand the culture of the companies they’re supporting. This can result in untargeted candidates who don’t fit. I experienced this issue firsthand when I was a CEO.

That’s why I strongly favour internal recruiters who have an intimate understanding of the business and culture. Even so, recruiters typically get involved after roles are clearly defined. Before that, to design the organization, we need someone who has visibility into the broader perspective of the business. Only one person truly has it: the CEO. Besides, CEOS usually can’t ask their leaders about organizational design for obvious reasons.

That’s where I step in—well before recruiters are involved. I act as a sounding board for organizational design, considering not just immediate hiring needs but also how roles and teams will evolve over time. What level of talent should they hire now? When will this position need to level up? What downstream implications will these decisions have?

By addressing these questions early, I help ensure hiring decisions are aligned with the company’s long-term strategy and culture.

Of course, hiring is just one area where I provide support. Design future-proof stock option plans? Manage internal and external communication challenges? Interact with strategic conglomerates? Navigate inbound acquisition offers? Resolve leadership dysfunction? Handle unreasonable investors? Make board meetings more effective? Fend off super aggressive competitors or internet giants?

And yes, one of the most frequent requests I get is: “Can you help me with my pitch deck?”

Bring them on!

I’ve faced these challenges firsthand multiple times, and when CEOs bring them to me, I’m ready to share my war scars.

At the minimum, I help narrow the options from “I don’t know how” to a set of multiple choices. I don’t make decisions for CEOs; I help them make better ones. They are ultimately responsible for their decisions, and I see my role as a guide, not a decision-maker.

Being the CEO of a fast-scaling company is an enormous challenge that people should not underestimate—the level of experience, capacity, intensity, and mental strength that one needs to cope with. That’s why it is the loneliest job. Empathy is not enough. The best help I ever got was from a more experienced CEO than me at the time — someone who had walked the road ahead — and now it’s my turn to pay it forward. It is payback time for me.

The more I think about it, the less “Operating Partner” seems to fit. I don’t step into the spotlight or take over operations. My role is more like Yoda—helping Skywalker fight the battles while staying behind the scenes.

So perhaps my title shouldn’t be Operating Partner after all. Maybe it should just be… Yoda.

May the Force be with you!

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.

Masterclass Series: Use This Framework to Move Fast and Make High-Quality Decisions

In many companies, the bottleneck isn’t necessarily in the execution of decisions. The real bottleneck is the excessive time people waste making decisions.

When I was Wattpad’s CEO, everyone in the company knew I had a simple 2×2 framework to empower the whole team to make fast, high-quality decisions – all by themselves!

The essence of this framework comes down to two questions:

• Is this decision reversible?

• Is this decision consequential?

These two factors create four types of decisions:

1. Reversible and inconsequential

2. Reversible and consequential

3. Irreversible and inconsequential

4. Irreversible and consequential

Examples of Each Type

1. Reversible and Inconsequential

This actually makes up the bulk of decisions in a company:

• Internal Slack messages? Delete them if you don’t like them.

• Marketing team’s benign social media copy? Remove the post if it doesn’t work.

• Small typo like the one in the above image? Yes, I purposely left the typo there. I look sloppy, but I could silently replace it with a better one when I have time.

• Small bugs in the product? If a bug fix causes other problems, revert the changes.

The list goes on. The trick is to empower each person in the company to make these decisions independently. I reinforced the same message to the Wattpad team over and over again:

From the most junior interns to the most senior leaders—you’re empowered to make the call all by yourself.

No boss to ask. No approval process. Just do it!

The company moves fast when most decisions don’t require a meeting!

2. Irreversible and Inconsequential

Here’s an example:

At one point, we ran out of space at Wattpad’s Toronto HQ and needed overflow space. We found a small office—just a few hundred square feet with a couple of meeting rooms—in the building right next door. The location was perfect, but the space itself? Just okay.

The problem was the lease—it was relatively long. Once we signed, we couldn’t back out. That limited our flexibility (irreversible), but we knew that if we needed more room, we could always find another expansion space. The cost was small in the grand scheme of things (inconsequential).

Given our growth, there was little downside to signing the lease. So we moved fast, signed the deal, and moved on to the next item on the to-do list.

For this type of decision, you can still move fast. Just be careful—double-check the lease for any hidden “gotchas.” It’s not about if we sign or not. We will sign, but we just want to make sure the bases are covered before we do.

You’d be surprised how much time people waste on indecision. Just make the call and do the due diligence!

3. Reversible and Consequential

A perfect example? A big product release.

Sonos’ poorly executed product release is a great case study. (See my blog post Masterclass Series: Complete Redesign That Actually Works for all the details.)

When done properly, product releases can be very consequential but still reversible. At Wattpad, we released high-risk software all the time—but always with a way to roll back if things didn’t work.

We knew how to press the undo button!

For these kinds of decisions, move fast and make the call—but monitor the outcome and always be ready to press undo.

Important: How to Increase the Quality of These Decisions

For both Irreversible and Inconsequential decisions and Reversible and Consequential decisions, always ask:

Is there any way to make this decision more reversible or less consequential?

If you can tweak the decision to minimize fallout—no matter how small—do it. It will save time and stress down the road.

4. Irreversible and Consequential

Many of these are leadership-team-level or CEO-level decisions.

They’re rare but also the hardest to make. They require a lot of context, consideration, and, sometimes, choosing between two bad options. Occasionally, you get a good one and choose between a few great choices.

The ultimate example for me?

Whether to take the company public, maintain the status quo and keep going, or accept an acquisition offer.

You all know the decision I made.

Sometimes, knowing which quadrant a decision falls into is an art. But imagine if we didn’t have this framework—slow decision-making would have ground the company to a halt.

The key to moving fast isn’t just execution—it’s deciding fast, too.

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.


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.

The Three Phases of Building a Great Tech Company: Technology, Product, and Commercialization

There are three distinct phases in the journey of building a great tech company: technology, product, and commercialization. These phases are sequential yet interconnected and sometimes overlap. Needless to say, mastering each is critical to the company’s eventual success. However, it’s important to recognize their differences.

• Building technology is about founders creating what they love. It’s driven by passion and expertise and often leads to groundbreaking innovations.

• Building a product is about creating something others love to use. This is where usability and solving real problems come into focus.

• Commercialization is about building something people will pay for and driving revenue. This phase transforms users into paying customers or finds someone else to pay for it, such as advertisers.

These phases are related but distinct. Great technology doesn’t guarantee anyone will use it, and a widely-used product doesn’t always lead to revenue. I’ve seen many technologists create incredible technologies no one adopts, as well as popular products that fail to commercialize effectively (though it’s rare for a product with tens of millions of users to fail entirely).

For deep tech companies, these phases often have minimal overlap and unfold sequentially. The technology might take years to develop before a usable product emerges, and commercialization may come even later.

In contrast, shallow tech B2B SaaS products often see complete overlap between the phases. For example, a subscription model is typically apparent from the outset, and the tech, product, and commercialization phases blend seamlessly.

Wattpad is also a good example of how these phases can play out differently. Initially, we built our technology and product hand in hand, creating a platform loved by millions of users. However, its commercialization—whether through ads, subscriptions, or movies, the three revenue models we had—was deliberately delayed. Many people assumed we didn’t know how to make money without understanding this counterintuitive approach (but of course, we purposely kept some of our strategies under wraps). This approach allowed us to use “free” as a potent weapon to dominate—and eliminate—our competitors in a winner-takes-all strategy. Operating for years with minimal revenue was clearly the right decision for the market dynamics and our long-term goals. More on this in a separate blog post.

Given this variability, asking, “What is your revenue?” must be thoughtful and context-specific. For some companies, the absence of revenue may be an intentional and brilliant strategy. For others, insufficient revenue could signal serious trouble. It all depends on the company’s stage, strategy, and goals. Understanding the sequence, timing, and specific needs of a business model is crucial for both investors and entrepreneurs. Zero revenue could be a blessing in the right context. On the other hand, pushing for revenue growth—let alone the wrong type of revenue growth—can be fatal, a scenario we’ve seen many times.

At Two Small Fish Ventures, we are very thoughtful and experienced investors. We understand that starting to generate revenue—or choosing not to generate revenue—at the right time is one of the secrets to success that very few people have mastered. We practise what we preach. Over the past two years, all but one of TSF’s investments have been pre-revenue.

No revenue? No problem. In fact, that’s great. Bring them on!

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: Unrecognizable Every Two Years

In 2006, Wattpad started as a simple mobile reading app, mainly for classic books. Fifteen years later, it evolved into a global, AI-powered, multi-platform entertainment company with numerous blockbusters before being acquired.

As you can imagine, my role as CEO at the start of Wattpad—when it was just the co-founders and a few hundred users—was drastically different from leading a team of hundreds of employees and overseeing a platform with 100 million users.

A Typical Entrepreneur’s Evolution

In the early years, the founders focused solely on building a product and finding product-market fit, with little thought given to the business side. At this stage, the CEO is the engineer writing code, the product manager, and the product visionary, all rolled into one.

As traction builds and product-market-fit comes into sight, the CEO’s role begins to shift. Suddenly, hiring becomes a priority, and managing people and operations takes center stage. The CEO goes from being a product builder to a hiring and people manager who leads a small, close-knit team and handles the operations that come with it.

Fast forward another phase, and the company is growing even faster. Now, the CEO is no longer just a manager but the manager of managers, responsible for hiring leaders who can build and lead their own teams. Communication becomes an even more critical skill, as the CEO now leads a much larger team—many of whom don’t frequently interact with the CEO. Business models become increasingly crucial, and new tasks, like fundraising, take on greater importance.

As growth continues, the CEO’s role shifts yet again, this time to hiring leaders of leaders—or even leaders of leaders of leaders. Now, the CEO is juggling closing million-dollar sales with key customers, navigating strategic partnerships, working with the CFO to manage finances at scale, media interviews, building the brand, international expansion, raising capital from large institutional investors, and, of course, leading hundreds or thousands of employees. The skill set required here is worlds apart from that of the early days of coding and prototyping.

Entrepreneurship Is Constant Reinvention

Each phase of a company’s growth requires a radically different skill set: moving from building the idea to scaling a product, building the team, leading a large organization, and eventually creating a profitable business. The entrepreneur evolves from crafting the “secret sauce” to building a factory to mass-produce it.

I have yet to meet an entrepreneur who possessed all these skills from the start. The journey demands constant learning—whether it’s coding, product design, finances, fundraising, marketing, sales, or leadership.

I can testify to this: there were numerous times when I thought the company was a well-oiled machine. Six months later, things would feel like they were falling apart. It wasn’t because I had messed up, but because the environment had changed drastically in such a short time. I had to keep upping my game to keep pace with the company. I am completely different from—and better than—the version of myself a decade ago—and not just once, but many times over.

As an entrepreneur, be prepared. As your company scales, you’re effectively getting a new job every few months. This journey is thrilling and challenging, and filled with lifelong learning and self-improvement.

The Biggest Takeaway

And yet, the most important product you’re building isn’t your company’s product. It isn’t even the company—it’s yourself.

If, every two years, you’re not almost unrecognizable from your former self, you’re not growing fast enough, and you will be left behind by your own fast-growing company.

This takeaway isn’t just for CEOs. It applies to anyone working at a fast-scaling company and to anyone with a growth mindset. If you get this right, everything else will follow, and you’ll be in good shape. From my experience, this is one of the most crucial mindset-building tools you can have.

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.

Contrarian Series: Contrarian Bets

In the early 2010s, when Wattpad began raising capital from Silicon Valley, Valley VCs didn’t ask me ‘if’ I would move the company or open a second office there; they asked ‘when.’ They argued that Toronto lacked great product people and scale-up leaders, although we had top engineering talent. At that time, it was common for Valley VCs to ask non-Valley companies to move to the Valley as a condition for funding.

But I told them, ‘I won’t move.’

While their argument had a point, Valley VCs failed to see my “big-fish-small-pond” advantages. I don’t need to hire a million great people. After raising one of the largest funding rounds by a Canadian-based company at the time, I was absolutely sure we could hire “enough” great people to help us build a world-class company based in one of the most populous metropolises in North America called Toronto. Paradoxically, it could even work to our advantage. As one of Toronto’s biggest fish, we could hire the best. I couldn’t say the same thing if we moved to the Valley. Besides, building a company culture with a single office location was much easier.

It was a contrarian bet that few people saw, but it was so obvious to me. In hindsight, it was clear that it was the right call.

It all worked well until it didn’t. While the Toronto ecosystem went from strength to strength during the 2010s, it also meant that the talent competition became very fierce towards the end of the decade. The small pond became a much bigger pond, and there were a lot of big fish in it, including many Valley-based companies setting up shops here.

The tipping point for me was when someone bought the old building next to Wattpad HQ. Initially, we had no idea who wanted to turn it into an office tower until Google announced that it would hire a few thousand people. Where? Right next to Wattpad HQ.

My first-mover advantage has eroded. I had to figure out a new plan to regain my big-fish-small-pond advantage.

My solution was to establish a second HQ in a less populous city with a thriving tech ecosystem and an abundance of post-secondary institutions, where we could be the big fish again and have enough talent to enable us to continue to grow rapidly. It had to be a Canadian city because I wanted a few existing Wattpad employees to relocate there to help us “seed” the culture. It was far harder for me to pull it off if it was cross-border.

I toured around the country. I was impressed by what I saw. There were a handful of cities that met our criteria. I knew we could make it work.

At that time, I was already very familiar with Halifax, having been involved in the local ecosystem for a while. While there, I took advantage of the opportunity to grab dinner with Jevon McDonald, whom I had known for a few years. Nothing compares to talking to a local guru.

Jevon gave me the rundown of all the nuances I couldn’t find on Google search. But when I asked him to name one thing that he didn’t like about Halifax, this was our conversation:

Jevon: “I have a few employees in San Francisco. Going there is very painful as I have to catch a 5am flight to connect through Toronto first.”

Me: “So, there is no direct flight from Halifax to SF?”

“Nope.”

“Great!”

“What?!”

It’s a short flight between Toronto and Halifax. There are numerous daily flights between the two cities, so day trips are super easy. However, the lack of direct flights to the Valley means Valley-based companies won’t show up any time soon. An unfair disadvantage became my unfair advantage. The lack of direct flights became my talent moat.

The rest is history. Wattpad established its second HQ in Halifax. We hired a lot of fantastic people there. I have been the biggest champion of Atlantic Canada ever since, as I have encouraged other Toronto-based companies to do the same.

It was another contrarian bet that few people saw, but it was so obvious to me. It was the right call.

These are just a couple of examples. There were many more that Wattpad did, like establishing a movie studio or investing in something unproven called AI more than a decade ago.

Similarly, some of our best investments in Two Small Fish Ventures, such as Sheertex or BenchSci, had a very tough time raising capital early on because very few people saw what we saw.

Of course, I am not suggesting that one should be contrarian for the sake of being contrarian. But when a contrarian bet results in a first-mover advantage in a big opportunity that no one else saw, that will almost always generate an amazing outcome with outsized returns.

Don’t tell anyone.

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.

International Women’s Day

When Eva and I were on stage yesterday at Entrepreneurship Week at the University of Toronto, moderator Bianca Bharti from BetaKit asked us:

“Given we are celebrating women and raising awareness about related issues this week, what do you want to tell the audience here today?”

Here is what I said. When I was Wattpad’s CEO, we didn’t just talk about diversity or run flashy programs just to make us look good. Instead, we invested in it. We allocated real resources, dollars, and people’s time to create a truly diverse and inclusive culture at Wattpad.

The business reason was simple – half the world’s population is female. If we want to properly capture this market, do you really think a bunch of male guys in the room can figure this out?

The end result is that we achieved gender parity at BOTH the employee level and the leadership team level. However, the numbers don’t tell the whole story. Anyone who worked for Wattpad can testify that we have created a truly inclusive culture.

Personally, I would consider this one of our biggest achievements.

But that was only the first chapter of the story. At Two Small Fish Ventures, we carry the same DNA. It was mostly Eva’s work, as I only started to be more involved in recent years. Through inspiration, advocacy, and mentorship, we achieved 50% female founders in our portfolio. In fact, many of our rocket ships are female-led.

Our job is not done yet. Together, we can change how the world operates.

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.

The Second Act, the Third Act and the Fourth Act

One of the three things that CEOs only do is to “make sure there is enough cash in the bank” (see job #3 here). Although CFOs may be responsible for much of the heavy lifting, keep in mind that CEOs’ job #1 is to communicate vision and strategies to all stakeholders, which certainly includes potential and existing investors. It is very hard to raise capital to build a great company without great storytelling skills, something almost all great CEOs possess.

Clearly communicating a bold vision is especially important for early-stage venture-backed companies. These companies are usually pre-revenue, pre-product-market-fit, and definitely pre-scaling. From the VCs’ perspective, they invest not only in where the company is today, but also where the company would be, could be, and should be. In many cases, investors buy into the company’s second, third, and fourth acts in the future, as very few great companies are one-trick ponies.

SRTX is the perfect example. Last week, we went to the grand opening of their mega-factory in Montreal. To my knowledge, it is now the largest textile factory in Canada. The pictures and videos don’t do justice to the massive scale of this facility.

This is especially impressive when you know that 180 days ago, when they took over the facility, the roof was leaking, there were no walls, and there was no electricity. The SRTX team moved mountains, rock by rock and at lightning speed, to get the factory ready for production. 

I wish I could share some pictures inside the factory. Unfortunately, I can’t share their secret sauce. If you really want to have an insider view, you have to become an investor 😉

It took 7 years from its inception for SRTX to begin evolving into a fully verticalized behemoth through innovations in advanced material, hardware, and software to deliver traceability, sustainability, durability, and cost advantages, which is now giving them an “unbreakable” advantage – pun fully intended!

Today, millions of Sheertex unbreakable pantyhose are sold. They became THE best-selling pantyhose, unbreakable or otherwise, in North America, not bad for a 15-person company based in Bracebridge, Ontario, a town with a 15,000 population and a 2-hour drive north of Toronto when Two Small Fish Ventures invested!

Now, they are ready to license the IPs of their rip-resistant technology to other textile companies. That’s their second act. Watertex, one of the world’s most hydrophobic polymers that is engineered for unparalleled water resistance for use in, say, swimwear, is their third act. There are other IPs that are in the works. I would call them their fourth act.

But please don’t use the word pivot here. Pivot implies ‘nothing works, let’s try something else.’  Since the early days, Katherine was very clear that selling pantyhose online was the necessary first act to give her the economy of scale before she could begin her second act, third act, and fourth act. What we see today is exactly how she articulated her bold vision when we invested in the seed round five years ago. We bought into her vision, joined the journey, and now, what she told us is becoming a reality. We wouldn’t have invested in a company that was merely selling pantyhose online, even if millions were being sold.

The power couple, Katherine Homuth and Zak Homuth, are not your typical founders. SRTX is rewriting the rules of textiles through innovations. I can’t wait to watch the second, third, and fourth acts unfold right before our eyes from my front-row seat.

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.

Founding CEOs vs. Professional CEOs

Silicon Valley’s founder CEO worship definitely has its merits. As a CEO backed by many valley VCs, I have immersed myself in that view for decades (e.g., Ben Horowitz’s Why We Prefer Founding CEOs). I get it, I understand where it comes from, and I do mostly agree. That’s why TSFV backs founding CEOs almost 100% exclusively.

Great founding CEOs tend to have all three traits: 1) Comprehensive knowledge of the entire company (including knowledge of every employee, product, technology decision, customer data, and the strengths and weaknesses of both the code base and the organization), 2) moral authority, and 3) total commitment to the long-term, while professional CEOs often don’t.

On the other hand, being a great CEO is more than just starting a company. It’s a super stressful job that nobody can learn overnight, and running a company with hundreds or thousands of employees is definitely a different ball game than being a founding CEO of a five-person company. However, founders who can’t scale with the company can’t stay in the captain’s chair forever.

If the two jobs are so different, why do we still prefer founding CEOs, even though many are learning on the job? Because it gives the company the best chance to become ultra-successful.

Typically, a company goes through four stages of growth. I call it the “4S’s”:

  • Start: where everything begins, with just the co-founders and a tiny team.
  • Sprout: achieving product-market fit, with the CEO calling most of the shots in a mostly informal setting.
  • Scale: rapid growth, hiring functional leaders, building depth, and starting to establish business processes. This is often where founder CEOs, especially first-time founder CEOs, stumble as they might lack experience in hiring and leading large teams.
  • Success: achieving a major milestone like an IPO or a massive liquidity event.

But the growth of a company isn’t a waterfall. An innovation company can’t stop innovating once its (first!) product has achieved product-market fit and cannot simply switch gears overnight to focus on business optimization. The most successful companies aren’t one-trick ponies; they need second and third acts long after their first product takes off.

Based on my own experience and my observation of hundreds of CEOs’ personal growth, I can confidently say that it’s far easier for a founding CEO to learn leadership than for a professional hire to become innovative and visionary. When the company hits scale-up mode, a founding CEO’s leadership needs to be solid, but any gaps can be filled by hiring strong leaders. Most founders can successfully make this jump.

On the flip side, pushing someone to be innovative and visionary is much harder, as is finding a team of leaders who can fill that gap for a professional CEO. That’s why it’s tougher for professional CEOs to succeed, though it’s not impossible. It is also possible to hire an “entrepreneurial” professional CEO, although they are rare gems.

However, this is all pretty generalized. Generalization tends to default to pattern recognition without thoughtful consideration of the specificity of the company’s situation. The ideal scenario is a founding CEO leading all the way, but sometimes, if a professional CEO is the only option, that’s what we have to work with.

The good news for TSFV’s portfolio CEOs is that you’ve got a founding CEO who’s been through it all – me! These days, I spend a lot of time helping founding CEOs fast-track their learning to operate more effectively on the job. For our professional CEOs, I offer guidance to help them think and act more like founders. Helping our portfolio CEOs is the best use of my time to ensure our portfolio companies’ success. It is also extremely high-leveraged because sometimes, even a 30-minute conversation with me can help change the trajectory of a company. After all, if our CEOs aren’t successful, it’s nearly impossible for our portfolio companies to be successful, isn’t 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.

Masterclass Series: Lead by Only Doing What You Can Uniquely Do

As a refresher, a CEO does only three things:

  • Sets the overall vision and strategy of the company and communicates it to all stakeholders.
  • Recruits, hires, and retains the very best talent for the company.
  • Ensures there is always enough cash in the bank.

These responsibilities might seem straightforward, but they encompass a vast array of tasks and decisions.

For instance, ensuring there is always enough cash in the bank could imply that a CEO needs to double as a CFO, but clearly, CEOs should not be CFOs. Similarly, hiring the very best talent could include all people functions, but of course, it should not.

In other words, even with just three things, CEOs will never run out of things to do. So how should they prioritize?

One guiding principle is that CEOs should only do things that they can uniquely do. Let someone else take care of the heavy lifting.

When Wattpad started to scale, this mindset shift really helped me prioritize. This problem is much more common than you may think. Based on my observations, I would even say that at some point, most inexperienced CEOs spend too little time on things that they can uniquely do. Failing to do so, the problem could manifest itself as people in the company chronically waiting on you before they can take their next actions on projects. You lose all the leverage you have in hiring a team.

You already paid them so much money to do the job for you. Don’t do their job for them!!!!

Although this lesson is mostly for CEOs, the same principle also applies to other leaders and managers. There is a bucket called ‘only you can do.’ Note that this bucket is not called ‘I can do it better‘ because who can do a better job or who can do it faster is not the issue here. Resisting the temptation to take on a task when your team can (should!) handle it can greatly help you improve your productivity and turn you into a much more effective leader.

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: What a CEO does

I’m a 3x entrepreneur. I was the CTO of my first company, which failed. I was the CEO of my second one, which was acquired when it was still very tiny.

Wattpad was my third and last company, but it was my first one as a scale-up CEO. It was a very different beast. The learning curve for me was extremely steep.

Thankfully, I was very privileged to have many world-class VCs and their firms invested in Wattpad. Being surrounded by world-class investors and their network not only helped me surmount that learning curve but also helped TSFV become a much better VC firm. More on that in a different post.

One of these firms is Union Square Ventures. The first and most important thing I learned from USV’s Fred Wilson is, “What does a CEO do?”

A CEO does only three things:

  • Sets the overall vision and strategy of the company and communicates it to all stakeholders.
  • Recruits, hires, and retains the very best talent for the company.
  • Ensures there is always enough cash in the bank.

A CEO should delegate all other tasks to his or her team.

In my experience, it’s rare to find great CEOs and consequently, great companies, not getting these three things right. Conversely, dysfunctional companies usually get at least one of these three things really wrong.

I frequently talked about these three things with my team at Wattpad. My leadership team and all the employees knew what to expect and could hold me accountable. And they did.

So much is packed into these three things. They are deceptively simple, and yet they are extremely nuanced. There’s enough material here for a book! So, expect multiple blog posts in the future on this topic.

However, this post alone is already a great guiding post for any CEO whose company has achieved (or is beyond) product-market fit, or the team is ready to scale, say, roughly 10 people, and even for companies of much larger size.

This post is the foundation of CEOs’ leadership, and everything flows from here. I learned it, I lived it, and I can testify that this is the first thing that any CEO must get right and keep getting right throughout their tenure.

And that’s precisely why this is the inaugural post in the Two Small Fish Ventures Masterclass Series.

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.

Allen’s Thoughts 2.0

One of the most unusual practices I used as CEO was writing an internal blog called “Allen’s Thoughts” on Wattpad every day. My preferred form of communication is the written word, a key reason behind co-founding Wattpad.

Although it might sound time-consuming – and it is – blogging helped me tremendously in clarifying my thinking. More importantly, context matters. The 30-60 minutes I spent each day aligned and interacted with hundreds of employees, arguably making it the most effective activity in terms of leveraging time. Here’s what I explained on Allen’s Thoughts about why I needed to do this:

“Wattpad is an incredibly complex company. We are a tech company, a media company, a book publisher, an advertising company, an influencer network, an AI company, a movie studio, a social network, a community, and also an entertainment company that makes people happy.

What links us together is our common vision, mission, values, and culture. Allen’s Thoughts is less about the numbers and company updates, which you can get on Slack, email, Google Docs, or other channels. This blog is more about sharing the context, the whys, and the intangibles in a narrative that helps you navigate that complexity so that you can make the best possible decisions and do your best job.

This blog is one of my unique superpowers that connects everyone.”

I started Allen’s Thoughts in 2013 and stopped daily blogging after stepping down in May 2022. My final post, “IT’S THE FINAL CURTAIN CALL. A NEW STORY BEGINS,” was shared publicly on allensthoughts.com.

Do I miss it? Absolutely, yes. However, after writing half a million words, I became too mentally exhausted.

After a long break, I am fully recharged and ready to reactivate my public blog. Although the Wattpad story is well-documented, many challenges and triumphs weren’t shared externally. These backstories are valuable case studies in business, leadership, entrepreneurship, venture capital and even time management. Re-reading my old posts, I realized they are a startup treasure trove, offering insights from scaling from two co-founders to a scaleup with hundreds of employees and 100 million users. I plan to share these lessons, along with many new topics.

Of course, I will also share my perspective on the startup investment landscape, our investment thesis, and our areas of focus – i.e., AI, protocols, and sustainable computing – among other topics.

This material will be part of our “School of Fish” Masterclass Series, more on this later.

I don’t plan to write daily. Frequency is not the most important aspect; it’s more about when inspiration strikes. My goal is to share high-quality, high-leverage, and impactful content. I will use Allen Thoughts to think things through “in public,” writing for my own enjoyment and hoping it benefits many others. After a hiatus, I’m eager, hungry, and excited to do it again!

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.

Delrina, ATI, Wattpad and Sheertex

The stories behind this picture we took in Muskoka a few weeks ago captured four incredible world-dominating startups.

From left to right: Sally Daub, Zak Homuth, Katherine Homuth, Eva Lau, Allen Lau, Dennis Bennie


Eva and I started our careers at Delrina in the ’90s. Delrina was a fledgling startup with a modest team of just over 20 when she joined. When I joined nine months later, it reached nearly 100 people. Less than four years later, when Dennis Bennie, the CEO and co-founder, brokered a half-a-billion-dollar deal with Symantec, the company employed just under 800 people and became one of the world’s top 10 PC software companies. With over 90% of the market share, Delrina’s products were so dominant that we crushed all our competitors. Truly legendary. 

Post-acquisition, Eva went to work for ATI, where she crossed paths with Sally Daub, then served as its General Counsel. ATI and its chief rival Nvidia emerged as the two world’s leading graphics chip players. In 2006, ATI was acquired by AMD for $5.4 billion. The transaction is one of the largest Canadian tech acquisitions. Probably still in the top three to date.

I’ll be succinct about Wattpad—it’s a story many are familiar with. We pioneered mobile reading, user-generated fiction, AI-and-audience-backed movies and many areas that resulted in billions of story uploads in over 50 languages, numerous world’s most-watched movies and 100 million users in virtually every corner of this planet.

Katherine and Zak Homuth’s Sheertex needs no introduction. In seven short years since its founding in Muskoka, the company became a world-famous household name and synonymous with unbreakable pantyhose. Three years ago, it took over the largest hosiery factory in Canada. To keep up with the demand, it is now moving into a space in Montreal three times larger. There is still so much headroom for growth.

These four Canadian companies are all world-dominating category creators.

As a passenger on the rocket ship, being the captain of the rocket ship and funding the rocket ship are three different skills. And yet, they’re intertwined, each amplifying the other. If you have never been on a rocket ship, it would be hard to imagine what a rocket ship looks like and spot the next one.

Eva and I have been immensely fortunate to wear multiple hats as employees, founders, and investors in many rocket ships. The timeless adage rings true: Surround yourself with the best. If you aim to be the best, work for the best and work with the best will help you learn from the best.

Goodbye 2010s, Hello 2020s

As we enter the final hours of the 2010s, to reflect and look forward I would like to share a couple of very contrasting collages. One was taken this year. The other was taken exactly 10 years ago.

Wattpad grew ~100x in virtually every single dimension – number of employees, the size of the office, number of users, number of stories shared but more importantly the positive impact on the Wattpad communities, our employees, our city and millions of lives we touched.

Two Small Fish Ventures grew from a side project to a VC firm with tens of rocket ships in the portfolio.

Most importantly, although the size of my family has not grown 100x (thank God!), my two little girls + an amazing lady has become two amazing young ladies + an even more amazing lady. They are the most influential on the most influential. They are the best and unquantifiable.

Look forward to 100x our impact on 100x more people in the 2020s!

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.

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.

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.