management

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!

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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.

Masterclass Series: The Triathlon Rule of Deep Tech Startups

A swimming world champion, a cycling champion, and a marathon champion each tried their hand at a triathlon.

None of them even came close to the podium. All were easily defeated.

Why?

Because the swimming champion could not bike, nor could he run fast.

The cycling champion did not swim well.

The marathon runner was painfully slow in the water.

The winner?

It was someone who had been humbled by the swimming champion in the pool for years, finishing second in the world championships multiple times. He was an exceptional swimmer, yes. However, he could also bike fast and run hard. Not the best in any single discipline, but strong across all three. And that is what won him the race.

The takeaway:

To win in triathlon, you need to be competitive in all three disciplines.

The winner is often world class in one of them, but they must be very good if not great at the other two.

This is the same mistake many first time deep tech founders make.

They believe that superior technology alone is enough to win.

It is not.

While technology is crucial, and in fact it is table stakes and the foundation of innovation, it must be transformed into a usable product. If it does not solve a real problem in a way people can adopt and benefit from, its brilliance is wasted.

And even if you have built world class technology and a beautifully crafted product, you are still not done. Without effective commercialization, which includes distribution, pricing, sales, positioning, and partnerships, you will not reach the users or customers who need what you have built.

I wrote more about this in The Three Phases of Building a Great Tech Company: Technology, Product, and Commercialization. Each phase demands different skills. Each must be taken seriously.

Neglecting any one of them is like trying to win a triathlon without training for the bike or the run.

Just like a triathlete must train in all three disciplines, a founder must excel across all three pillars:

  • Great and defensible technology
  • An excellent product
  • Execution on commercialization

You need all three.

That is how you win the world championship.

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.

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.