Essays – Positive Tenacity

Abstractions and Why Details Still Matter

Today, I came across an interview with Jerry Seinfield that left an impression on me. One paragraph in particular stood out:

If you’re efficient, you’re doing it the wrong way. The right way is the hard way. The show was successful because I micromanaged it—every word, every line, every take, every edit, every casting. That’s my way of life.
Jerry Seinfield

This reminded me of an essay by Joel Spolsky. In our work, we encounter many professionals who excel at “abstractions,” or what some might call “strategic” thinking. I must admit, I enjoy these abstractions. The process of moving up the layers of abstraction can be intellectually satisfying and enlightening.

This is not limited to professional work, but also extends to academia, where physicists are still searching for the Grand Unified Theory. We find patterns everywhere; our brains are pattern recognition & recall machines. We encode discrete experiences into abstract models so we can efficiently recall and apply them to our lives for swift decisions and actions. The right models can provide useful insights and even forecast the future to a certain degree.

However, just like an AI model that is versatile can still lose the exact details of the reality, high-level abstraction models can prevent us from being effective “where the rubber meets the road” especially when it comes to building your startup.

Most of these abstractions may not prove useful when faced with the question, “So what are we going to do here?” when supplied with the messy context of reality. Even worse, when someone is fixated on their model, reality itself may no longer be of interest to them.

As builders, we must recognize that while deriving insights and models will be useful for the future, we must also understand the constraints and context of the reality in which we operate to be effective. The only way to make a difference is to execute based on the cold, harsh reality and problem-solve, sometimes at the lowest level of detail.

I will end with a small story shared by Vic Gundotra, former VP at Google, about one of his experiences working with Steve Jobs, titled “Icon Ambulance.”:

One Sunday morning, January 6th, 2008 I was attending religious services when my cell phone vibrated. As discreetly as possible, I checked the phone and noticed that my phone said “Caller ID unknown”. I choose to ignore.

After services, as I was walking to my car with my family, I checked my cell phone messages. The message left was from Steve Jobs. “Vic, can you call me at home? I have something urgent to discuss” it said.

Before I even reached my car, I called Steve Jobs back. I was responsible for all mobile applications at Google, and in that role, had regular dealings with Steve. It was one of the perks of the job.

“Hey Steve – this is Vic”, I said. “I’m sorry I didn’t answer your call earlier. I was in religious services, and the caller ID said unknown, so I didn’t pick up”.

Steve laughed. He said, “Vic, unless the Caller ID said ‘GOD’, you should never pick up during services”.

I laughed nervously. After all, while it was customary for Steve to call during the week upset about something, it was unusual for him to call me on Sunday and ask me to call his home. I wondered what was so important?

“So Vic, we have an urgent issue, one that I need addressed right away. I’ve already assigned someone from my team to help you, and I hope you can fix this tomorrow” said Steve.

“I’ve been looking at the Google logo on the iPhone and I’m not happy with the icon. The second O in Google doesn’t have the right yellow gradient. It’s just wrong and I’m going to have Greg fix it tomorrow. Is that okay with you?”

Of course this was okay with me. A few minutes later on that Sunday I received an email from Steve with the subject “Icon Ambulance”. The email directed me to work with Greg Christie to fix the icon.

Since I was 11 years old and fell in love with an Apple II, I have dozens of stories to tell about Apple products. They have been a part of my life for decades. Even when I worked for 15 years for Bill Gates at Microsoft, I had a huge admiration for Steve and what Apple had produced.

But in the end, when I think about leadership, passion and attention to detail, I think back to the call I received from Steve Jobs on a Sunday morning in January. It was a lesson I’ll never forget. CEOs should care about details. Even shades of yellow. On a Sunday.

To one of the greatest leaders I’ve ever met, my prayers and hopes are with you Steve.

– Vic (his original post is no longer available due to Google+ being discontinued for consumer/personal users)

The Level 5 Ownership

Leaders are often called upon to resolve conflicts and problems. During this process, we all experience varying degrees of ownership from the people involved. The level of ownership significantly affects how we problem-solve with these individuals and the effectiveness of our efforts.

However, ownership is a concept that is often talked about but less understood. Below are five levels of ownership that will help leaders understand the differences.

Level 1: Lack of ownership

Response: “This is not my fault. I did what I was told to do.”

At this level, the person involved will actively distance themselves from the issue, fearing criticism or negative reflections on their performance review. The effort is focused on rationalizing their actions and explaining to others how they were not part of the problem.

The problem with this approach is that while the person may believe they are “safe” by doing this, it creates more doubt in others, especially among team members. It also results in a significant loss of social capital and reflects poorly on their character.

Level 2: Owning intent

Response: “My intent was good, so even if my actions weren’t ideal, I’m not responsible as it came from good intentions.”

This level is typically seen among young adults who have experienced social conflicts and have learned that they will be held accountable for problems. Conveying good intent is important to justify their positions and seemingly wrongdoings.

The problem is that even if the intent was good, if the actions do not align with the intent, people will ultimately remember the decisions and actions. Unless corrective actions are taken in the future, social capital will be lost at this level.

Level 3: Owning actions

Response: “My intent and actions were good, so even if the outcome isn’t good, I did my best, so I’m not responsible, as results were out of my hands.”

This level is commonly seen among working professionals where their managers hold them accountable for activities and “deliverables.” In business cultures that value hard work, focus on target dates, and celebrate launches, this may seem normal and harmless.

The problem is that even if the individual believes they did everything right, if they do not deliver on the outcomes, all recognitions of the actions taken can feel like patting each other on the back. The learning at this level is often limited to “we just have to try harder next time” or blaming the “environment” for missing the target.

Level 4: Owning outcomes

Response: “Although my intent and actions were good, the outcome wasn’t, therefore I am responsible.”

This level is sometimes seen among experienced professionals and seasoned leaders. They realize that owning actions is not enough and that they must ultimately deliver on their outcomes. They track the results as often as possible and course-correct their actions in real-time to change the trajectory of their results. They understand that unless they meet or exceed their outcomes, it is only a matter of time before they are held accountable or replaced.

The only minor issue at this level is that even if the individual succeeds, if their team still misses their goals, they are not winning as a whole.

Level 5: Owning collective outcomes

Response: “Although my intent, actions, and outcome I was personally responsible for were good, our team failed to deliver on the mission, so I ultimately feel responsible for our team. I believe there were ways I could have done things differently or even better to help our team succeed.”

This level is a rare quality even among seasoned leaders. They not only own their personal outcomes and the team they manage, but they expand their responsibility to their peers and the organization they are part of. They understand that unless their team and organization win, they are not truly winning. As a result, they mobilize their resources and efforts beyond their current roles and responsibilities to help elevate the people and teams around them.

At this level, the person takes ownership of not only their own actions and outcomes, but also the collective success of their team and organization. They are willing to go above and beyond to help their team and organization succeed and are not afraid to take on additional responsibility to make it happen.

What’s next?

Understanding these five levels of ownership will help leaders identify where they and their team members fall and make the necessary changes to improve. By moving up the levels of ownership, leaders will be able to take on more responsibility and drive better results for themselves, their teams, and their organizations.

Remember, owning the problem does not mean that you are solely responsible for fixing it. It means that you are willing to take on the challenge and do what it takes to find a solution, even if it means seeking help from others. Taking ownership allows you to be proactive in addressing issues, rather than reacting to them after the fact.

Leaders who embrace ownership create a culture of accountability and responsibility, leading to better outcomes and a more cohesive team. So the next time you face a problem, ask yourself: what level of ownership am I taking?

On Motivation

Someone recently asked me “how can I motivate my team member when the market is down and the value of their stock options may not grow as quickly?” I initially tried to answer the question by focusing on the odds of startup valuation still growing faster than other asset classes, and other non-linear & intrinsic value of social capital accumulated at startups that may introduce new opportunities later in life. But I didn’t find my answers satisfying at all. I thought about why.

Over time, experience has taught me that more often than not, defining the right problem to solve is far more important than the solution itself. Perfect solution to a wrong problem is just plain wasteful.

So how can one motivate their team member when things are getting tough? What are the mechanics behind motivation that can give us insights into finding the right solution to the problem?

Entrepreneur’s Flywheel

Flywheel is a relatively straightforward concept to understand, but still worth reading this book for more practical tips when you’re drafting your flywheels.

Below is an example of a high-level flywheel crafted for entrepreneurs. The inner loop is when founders start a company themselves to solve a big problem and create value.

Managing Time Horizons

I recently came across the clearest definition of a bubble in an asset class:

“When investors have different goals and time horizons—and they do in every asset class— prices that look ridiculous to one person can make sense to another…

Bubbles form when the momentum of short-term returns attract enough money that the makeup of investors shifts from mostly long term to mostly short term. That process feeds on itself. As traders push up short-term returns, they attract even more traders. Before long, the dominant market price-setters with the most authority are those with shorter time horizons.

Bubbles aren’t so much about valuations rising. That’s just a symptom of something else: time horizons shrinking as more short-term traders enter the playing field.”
The Psychology of Money (by Morgan Housel)

What was particularly impressive about this framework was that it can be applied to any forms of investment — including people. When you have a “different” time horizon when working with someone, your behaviors will change.

Thinking Second-order Effects

💡 I was going to write a longer piece on this topic, but found this article to be helpful.

One of the key elements of being better in leadership, strategy, and organizational changes is being able to think and anticipate second-order effects.

When you want to roll out programs, systematic changes, (re)budgeting, headcount planning, introducing new processes, thinking beyond the first intended first-order, being able to navigate second-order effects will be critical in how successful those initiatives will be. Most outcomes will be lagging and have lasting/trickling effect throughout the organization, so the quality of the decision and the thoughtfulness matters a lot to save a lot of people’s time, effort, and pain.

A Guide to Scaling Yourself

How to keep your head above water

I was having lunch with a friend today, and we were discussing how does someone know when a person is scaling or not. Who will scale as the company grow and what stops someone from scaling further?

Some companies have early members scaling beautifully as the organization grows, while some don’t. A lot of smooth scaling happens typically when the company is growing organically and the growth rate is relatively modest (< 50% YoY). When a company is growing > 50% YoY, and in some cases, doubling or more, it becomes incredibly difficult for people to keep up with the scale of the company, as humans grow linearly, yet companies grow exponentially.

Below are a few questions to ask yourself to check if you are scaling with the growth needed and some tips and strategies to continue on the fast growth trajectory.

1. Am I “going horizontal?”

I came across the concept of “Going Horizontal” during 10xCEO program and we discussed extensively on how to make sure the executive team is continuing to scale at the right capacity level for the growth needs of the company.

The team internally might already be “over capacity” if the company’s growth rate is modest and the team is experienced. But if the needs for the leadership capacity emerging from growth out weigh the current capacity, then it will hurt the growth rate and the potential upside of the company as long as the leadership team is not fully built to handle the needs.

VPC Framework in Management

Balancing between Value, Price, and Cost

I first learned the VPC Framework (VPC: Value-Price-Cost) back in 2006 and the simplicity of the framework made an impression on me. I still revisit a few times a year to think about where our company is in the position within the framework and how we are investing our resources.

The concept is quite simple. Let’s start with the definition:

Value: This is the value your offering is creating and delivering to customers.
Price: This is the price you charge and customers pay for to acquire or use your offering.
Cost: This is the cost of creating and delivering your offering to the customer.

The differences between these elements create the benefits:

It’s okay to be not liked on demo day.

Y Combinator W16 Demo Day Story

Below is a post I wrote in August 2019 within Y Combinator community (which luckily received 300+ upvotes 🙇‍♂️). Now that I get a pretty steady stream of inquiries about fundraising and accelerator/demo days, I thought it might be helpful to repost here in public format. Hope it brings hope to a few.

Hi S19 founders,

Now that the demo day has officially begun, I just want to share our experience at SendBird (W16), so that perhaps some of you guys can relate.

I’ll admit upfront: We were not the hot company of the demo day. No where near. We didn’t get the overly enthusiastic emails from investors piling up in our inbox.

I thought we were doing okay during the batch, but on the demo day, the ones that got the most amount of ‘likes’ and ‘quickest raises’ were not necessarily the ones we thought did the best during the batch. Some companies raised a lot of money almost on the day of the demo day, while most of us felt like we were punched in our stomach, grasping for air.

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Level 1: Lack of ownership

Level 2: Owning intent

Level 3: Owning actions

Level 4: Owning outcomes

Level 5: Owning collective outcomes

What’s next?

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1. Am I “going horizontal?”

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