May is Asian Heritage Month in North America, which makes it a good time to talk about the bamboo ceiling.
You cannot turn left and turn right at the same time. Eastern and Western value systems are optimized for different paths to outcomes. One is optimized for harmony. The other is optimized for constructive tension.
Neither is right or wrong. But they can be incompatible. The bamboo ceiling can be the visible symptom of that incompatibility. But I don’t think it is always the root cause.
The deeper issue is often discomfort avoidance. And that is not uniquely Asian. Discomfort avoidance is human nature. It is just more pronounced when you are navigating incompatible systems.
I was born and raised in the East and have spent my entire adulthood in the West. The breakthrough came when I became more comfortable with discomfort. It unleashed the full potential of what I could do. I started doing things I never thought I could do as a young adult.
That is when my cultural bilingualism became an unfair advantage rather than a limitation.
Disagreement became contribution. “No” became something to explore. Speaking up became leadership. Growth, leadership, and influence live on the other side of discomfort.
I wrote more on this in my latest Substack post here.
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.
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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.
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.
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!
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.
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.
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.
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.
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.
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.
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.
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.
