Tech and Philosophy Need To Fix Their Relationship Problem

Originally posted here: https://stanfordreview.org/tech-and-philosophy-need-to-fix-their-relationship-problem/

Over the past few years, the tech industry has begun to fetishize the field of philosophy. Entrepreneurs like Peter ThielReid Hoffman, and Stewart Butterfield have begun to publicly credit philosophy as integral to their success. Thought leaders like Tim Ferriss have introduced Stoicism to engineers. As a result, enthusiasm for philosophy has quickly grown -- but without any targeted direction. The tech industry's newfound obsession with this previously dismissed field of academia is misguided and shallow.

While identifying the precise motivation behind the philosophy trend is difficult, it could likely stem from insecurity. As universities pump out more and more computer science majors, engineers and entrepreneurs may seek new intellectual pursuits to distinguish them from their peers. Philosophy may attract sheep for its grandiose nature. Quoting Kant is often seen as a signal of individualism and intellectualism. And to be one of the legendary polymaths is alluring; being well-versed in a variety of disciplines, including philosophy, offers a sort of social edge. While engineers’ newfound interest in philosophy might reflect a sincere desire to understand the principles behind their work, more likely it is an attempt to conform to the latest Silicon Valley trend.

Regardless of the motivation, many of Silicon Valley's endeavors to adopt philosophy fall flat. Consider the application of one of the earliest fields of personal ethics, Stoicism, which preaches living abstemiously. Despite a bevy of newly-christened tech worker “stoics,” it is difficult to find people in Silicon Valley who actually exercise this life mantra. With luxuries like avocado toast and Kombucha on tap, the perks provided by Silicon Valley companies don't exactly scream "minimalist." Companies that offer vast and various food options to their employees, almost to the point of endorsing gluttony, claim to promote productivity. However, enjoying these top perks is antithetical to the stoic life these engineers preach.

Perhaps attempts to apply Stoicism and other fields of philosophy have failed. But seriously contemplated philosophy should be crucial to the tech world. For example, engineers, like the rest of us, should constantly try to recognize their moral intuitions and question them. Consider the age-old mission of the archetypical Silicon Valley company: to "change the world." But how does one decide what is good for the world? Luckily, others have grappled with these queries. In fact, thinkers have spent millennia developing the field of ethics. Another Review writer similarly argued the importance of the study of ethics for engineering, asking for rigorous classes in ethics as part of computer science education. Beyond computer science education, however, without ethics, technologists cannot truly define what “good” they are trying to achieve. Ethics in engineering is much more useful for engineers to learn than Stoicism; whether you are personally happy is ultimately not as important as determining if the code you write could hurt society.

The oft-maligned Facebook is a prime example of the importance of ethical inquiry in the realm of tech. Worryingly, no community in history has reached a similar size to Facebook without a guiding set of philosophical principles. Many modern countries like the United States established guidelines like those in the Constitution and Declaration of Independence before experiencing significant growth. To determine the optimal creed for a community is challenging, and there is no obvious answer. Therefore each company must ask its own set of ethical questions, contingent on what it is endeavoring to build. It took the Facebook team nearly 14 years to conclude that not everything they were working on was, on the net, beneficial for the world. Many former early Facebook employees are only now recognizing that a failure to consider whether their products were ethical allowed issues like newsfeed addiction and misinformation to flourish. Consider the following example.

Many former Facebook executives have come forward about their opinions on the product that they helped make. Sean Parker, the first president of Facebook, recognized the issues of social media addiction that Facebook can play in our lives. Similarly, Chamath Palihapitiya, former Facebook VP of Growth, criticized Facebook for its misinformation problem, citing that “bad actors can now manipulate large swathes of people.” Since then, Zuckerberg has also concededthat Facebook, far from being an obvious good, presents real moral conundrums. His recent introspection and reflection set an example that engineers ought to emulate if they genuinely strive to change the world for the better. While tech behemoths like Facebook may help the economy and society, they must also be cognizant of their products’ potential negative consequences. And it is the responsibility of engineers, the architects of these products, to grapple with challenging ethical questions.

While advocating for the importance of philosophy might seem airy and idealistic, in fact, a single engineer with strong ethical principles can change the tides of a large company. In Silicon Valley, engineers are prized; in large tech companies, they are easily the most valued employees. Without them, tech companies’ product would not exist. Moreover, there have been countless instances in which engineers have been able to convince leadership to cancel a product on moral grounds.

For years, Google’s code of conduct included the motto “don’t be evil.” Although the slogan is vague, it has sometimes successfully encouraged engineers to stop and ponder the ethical and societal ramifications of the products they develop. Consider the following incident at Google, in which the chairman describes how an engineer prevented a product’s release.

"So what happens is, I'm sitting in this meeting, and we're having this debate about an advertising product. And one of the engineers pounds his fists on the table and says, that's evil. And then the whole conversation stops, everyone goes into conniptions, and eventually we stopped the project. So [the “don’t be evil policy”] did work."

This incident serves not to frame Google as a perfect company. Nevertheless, it illustrates the influence that engineers hold within Silicon Valley. Philosophy has often been a means for Silicon Valley to engage with the humanities shallowly, rather than to meaningfully change behavior. But the study of ethics should serve as a guide for engineers and entrepreneurs. Engineers should examine the products they are creating and lives they are living. Only then can they fairly claim that they are trying to change the world for good.

(Image Source)


Learning Lessons from Failure

I used to believe that learning from failure was futile. I believed this because I thought that failure could come from many reasons, so it was a wasted effort to try to determine any single reason for why it failed. 

I was influenced by this Peter Thiel quotation:

“I think failure is massively overrated. Most businesses fail for more than one reason. So when a business fails, you often don’t learn anything at all because the failure was overdetermined. [TF: Overdetermined: “To determine, account for, or cause (something) in more than one way or with more conditions than are necessary.”] You will think it failed for Reason 1, but it failed for Reasons 1 through 5. And so the next business you start will fail for Reason 2, and then for 3 and so on.”

Excerpt From: Timothy Ferriss. “Tools of Titans.” 

Now, I believe that both Peter and I are/were wrong for holding this point of view. (I still agree that most failure is overdetermined; it's unlikely that one particular thing caused a business to fail.)

Firstly, I'm going to argue that having a piece of knowledge is better than having no knowledge for starting a startup. 

1. the probability of succeeding in another startup conditioned on having a bit of learning from failure (not the full reason) is higher than the probability of succeeding in another startup with no takeaways from the failure. 

It just doesn't make sense that knowing about a particular situation to avoid (i.e. failure) would reduce the likelihood of success from the initial state of knowledge before failure at all. (Though I'd be very open to hearing arguments against this)

2. I would posit that it still is much better to learn the right way rather than learning from the wrong way. Historically, we have seen that there are more wrong ways to run a startup than right ways to run a startup.

Thoughts where I'm wrong? Leave in the comments :)


Test of competency

My friend Matt wrote a startup book. It's really good. One of the points that resonated with me deeply is this one:

"A large turning point is when a founder brings on a fantastic hire who can take vague intentions and wants ("Can you please do  _ / Our goal is to increase _ by X%"), and can consistently do more than you expect."

It's now my new favorite test for both myself and the people I work with.

Learnings from python challenge

This a list of learnings after my first accountability challenge (for simplicity):

  • Make sure you know what your schedule will look like before you start. Schoolwork had to take higher precedent, so I ended up cramming through most of the book
  • Ask for advice from others before you complete a challenge. The book that I used was a ton of fluff, and really could have been condensed into 50-75 pages of useful info.
  • I think accountability challenges work best on habits. It's kind of hard to set a challenge for something that has an uncertain amount of time to complete
  • They work. I think the social component is the biggest piece of it.

Life update: I'm really getting into rationality. Started this book, and hope to finish it by the end of the quarter. Looking forward to some writing on the subject.

8 Principles of Great Leadership


Originally published on 8 VC's blog

Inspired by our piece ‘A Deficit of Leadership’, two up-and-coming leaders in our community shared some of the most important principles of leadership below. We’re excited to see what’s next for Aneesh Pappu and Josh Singer.

As a founder, learning how to launch your startup is incredibly important. But as your project grows, you will have more and more people following your lead. Many founders are inexperienced at the art of leadership and lack the management principles necessary to build an enduring company. History ー even the history of Silicon Valley ー furnishes many illustrations of skillful leadership and of principles that every leader should adhere to.

Goal of a leader: The most important quality of a good leader is to empower those you lead to do their best.

Principle 1: Plan and prepare for situations that are under your control, but also recognize randomness and things out of your control.

As a leader, you have to recognize that many factors are out of your control. You must simultaneously plan for the future and prepare for randomness. Only the best master the art of adapting to black swan events with planning and prep.

Never confuse uncertainty with risk when making decisions. Risk is the range of possible outcomes for your action and their associated probabilities — it’s a feature of the external world. Uncertainty is not knowing the entire range of possible outcomes — it’s a feature of your mindset and knowledge base. Successful leaders are able to make ‘flexible’ plans which hedge against uncertainty.

“You need to try to do the impossible, to anticipate the unexpected. And when the unexpected happens, you should double the efforts to make order from the disorder it creates in your life. The motto I’m advocating is — Let chaos reign, then rein chaos. Does that mean that you shouldn’t plan? Not at all. You need to plan the way a fire department plans. It cannot anticipate fires, so it has to shape a flexible organization that is capable of responding to unpredictable events.” ー Andy Grove [1]

Principle 2: Self-awareness is one of the most important qualities of a world-class leader

Leadership is a particular exercise of power; it is predicated on one’s ability to influence others. In order to be a great leader, you must have a clear view of the ways you channel power and the magnitude of your intended actions. In addition, you should recognize your own deficiencies and take steps to account for those deficiencies.

Self-awareness grows exponentially more difficult as the size of your team and your responsibilities grow. Business successes reinforce your belief that you know what you are doing because those around you become more likely to defer to your authority. Unless you are maximally self-aware, you will be less likely to question your immediate thinking, which will ultimately lead to poor decision-making. Great leaders must avoid this debilitating cognitive bias.

Within Silicon Valley, the canonical example of such a self-awareness is the COO hire. Many great CEOs have realized their personal deficiencies and have brought in great COOs to complement those deficiencies [2]. Steve Jobs, when coming back to Apple in 1997, hired Tim Cook to allow Jobs focus on his strengths. Bill Gates hired Jon Shirley to help with operations, and Mark Zuckerberg brought in Sheryl Sandberg to help transition Facebook from a great product to a great business.

As we see more and more technical founders start companies, we will see more technical CEOs with bias towards engineering and product. It is crucial for CEOs to recognize their likely weakness in an area and plan accordingly to fill the gap.

Principle 3: Align the incentives of each and every member of your team

Each person on your team is human and therefore has incentives. It’s your duty as a leader to craft a system that aligns your follower’s incentives.

“To understand the true quality of people, you must look into their minds, and examine their pursuits and aversions.” — Marcus Aurelius

The first step is to determine your followers’ real desires. Then, you must lead them to their desires through efficient action, and clearly communicate to them that following you will lead them to fulfillment.

Incentives are complex; there is far more at play than simple profit-motive. Understand that people are human and have emotions such as dignity and pride. Don’t ever underestimate those emotions in decision-making and execution, and factor them into how you structure your organization and policies. These emotions play just as much a role as explicit incentives do.

Napoleon did this well. He took a band of weak soldiers and empowered them by appealing to their incentives. That band of soldiers then helped him build France into an empire.

“Soldiers, you are naked and ill fed… no fame is reflected upon you. I seek to lead you into the most fertile plains in the world… there you will find honor, glory and riches.” — Napoleon [3]

It’s important to design your structures such that human emotional incentives are taken into account. Not doing so can create negative unintended consequences. Ben Horowitz, CEO of LoudCloud and Opsware, discusses the importance of taking into account the natural incentive of wanting to be recognized and rewarded when designing promotion procedures. In The Hard Thing About Hard Things, he says, “Every time your company gives someone a promotion, everyone at that person’s organizational level evaluates the promotion and judges whether merit or political favors yielded it.” [4] Ensure that you structure your policies rigorously so that these second order effects of your decisions based on others’ emotions are known ahead of time.

There are many ways to apply this principle to modern-day Silicon Valley. For example, during salary negotiations, recognizing what an employee wants (whether more salary or equity) is key. Second, establishing a fair set of compensation principles will keep people’s dignity and pride safe.

Principle 4: Have trust in your team’s commitment to excellence

“Realize that many mistakes, even egregious ones, are the result of ignorance.” ー Marcus Aurelius

It’s important to have the mindset that your team is committed to excellence ー if you don’t believe this, then you’ve probably hired the wrong team. Having this mindset is key to navigating mistakes when they occur.

It’s inevitable that your team will make mistakes. As a leader, you must trust that mistakes come from a place of ignorance unless proven otherwise.

Trusting your team empowers them to do well. However the flip side is that it can cause your team to be overconfident in their abilities and consequently underestimate the likelihood that they have made a mistake. So, while trusting your team’s commitment to achieving top performance, you must take the responsibility to check in often enough to catch mistakes.

A great example of how to balance trust with verification is Andy Grove’s take on open door policies (i.e. ‘my door is always open if you have questions or run into trouble’). He pointed out that open door policies seldom work because people are not likely to bring up potential mistakes proactively [1]. A leader who remembers that people are naturally overconfident and prideful will instead take the onus upon themselves to check in at times when their team members could be failing.

Making these corrections in an educational manner (by reinforcing the team’s goals and explaining why correction is necessary) and not a punitive manner (by overly chastising or reprimanding) is integral to this principle. If you as a leader fully believe that mistakes are because of ignorance, you will see that there is no reason to be angry. Furthermore, creating a culture in which admitting error is OKーand is actually positive and neededーwill align individual incentives towards team success over personal gain or ‘saving face’.

Sheryl Sandberg, a great modern leader in Silicon Valley, is great at giving quality feedback. In an interview, Kim Scott, a previous employee, talks about how Sandberg had a way of giving critical feedback while simultaneously assuring employees that she fully trusted their ability. “Part of the reason Sheryl was able to say to me so bluntly, ‘You sounded stupid,’ was that I knew that she cared personally about me. She had done a thousand things that showed me that” [5]. This is a perfect example of believing in your team’s commitment to excellence.

Principle 5: Be appropriately optimistic

As a leader, it’s important to convey your belief and optimism in the team and the overall success of the company. Your followers benefit from this optimism because it increases their belief that their work will be meaningful. However, if you are too optimistic in terrible times, your team will 1) see through it and lose trust in you and the direction of the company and 2) won’t be personally motivated to fix the issues.

In The Hard Thing About Hard Things, Horowitz discusses the importance of optimism and the appropriate application of such optimism in leadership, for instance in the classic example of CEOs hiding bad news. He writes, “As the highest-ranking person in the company, I thought that I would be best able to handle bad news. The opposite was true: Nobody took bad news harder than I did. Engineers easily brushed off things that kept me awake all night… If things went horribly wrong, they could walk away, but I could not. As a consequence, the employees handled losses much better.” [4]

The key is to be optimistic about the future, but absolutely realistic about the present. You must “tell it like it is”, as Horowitz would say (see next principle).

A Silicon Valley analog is sharing the contextualized high points each week with your team. For example, if your company grows by 20% more than expected in a certain metric, share that with your team! However, the flip side of this can be seen when new rounds are raised. For many Silicon Valley companies, there’s overzealous celebration after a new round of fundraising has been finished. Although a good funding round is important, it by no means says that a company has made it or is doing ridiculously well; it just means that investors think highly of the company. Recognize that certain situations warrant a certain amount of optimism, and that you should convey that appropriate amount of optimism to your team.

Principle 6: Transparency is of utmost importance

Being transparent as a leader is necessary to the success of your team. Acting on this principle accomplishes the following:

It builds your team’s trust in you. Horowitz points out that “As a company grows, communication becomes its biggest challenge… if the employees fundamentally trust the CEO, then communications will be vastly more efficient than if they don’t. Telling things as they are is a critical part of building this trust.”

It establishes a culture of problem-solving rather than problem-hiding, which is crucial for team success. Horowitz points out that honesty creates “a culture that rewards — not punishes — people for getting problems into the open where they can be solved.” Also, getting problems out as soon as possible allows your company’s best minds to attack them. You didn’t hire good engineers so that you could stress out and try to solve the hard problems yourself.

It inspires your team. When you share more information with your organization/followers, you help catalyze a sense of ownership. As your followers get more and more information about the internals of a company, they psychologically attach themselves to the company and its future. And as a result of that attachment, they feel more inclined to ensure its success.

The highest form of inspiration is when your followers clearly understand both what to do and why.

For many Silicon Valley companies, transparency is one of the more defining aspects of a successful company culture. Many of the most successful companies have instituted a policy of nearly or completely universal access to the codebase and weekly Q&A’s with leadership.

Principle 7: When it’s time to execute, execute quickly and efficiently

“You may delay, but time will not, and lost time is never found again.” — Benjamin Franklin

You do a disservice to your followers when you procrastinate, and delaying your action conveys an uncertainty that will ripple throughout your following. When you are uncertain, evaluate. But when you make a decision, execute.

As a leader, especially within the fast-paced environment of Silicon Valley, you have a commitment to keeping your team successful. If a competitor builds a new feature that will put your team out of business, it’s your duty as a leader to take precautions to keep your team in the game. To be truly successful within Silicon Valley, you must learn to reconcile perfectionism and thoughtfulness with the will to execute.

Take Uber for example. Lyft was first to market in ride sharing with sedans when Uber still only had black car. Uber rolled around one month later (June to July 2012) and continually has done whatever it takes to beat Lyft, whether keeping up with price reductions or hiring city officials in order to expedite expanding there (i.e. New York).

Principle 8: Be the servant to each and every one of your followers

“The job of a manager is to support his or her staff, not vice versa and that begins by being among them.” ー Hewlett and Packard [6]

An effective leader prioritizes the wellbeing of his/her team members. If you aren’t there to help your team, what is your team there to do in the first place? Leadership is a bidirectional structure. Your followers need a leader to follow, and you need followers to lead. Your investment in them is an investment in yourself.

Acting on this principle does two things. First, it fosters your empathy for those on your team: to serve someone, you have to fully understand the problems they have. As a leader, resolving those problems is your most important job, and you must exemplify that your team’s culture is one of helping. Second, it motivates your followers to reach their potential, because your investment of time is a signal that they will grow.

One classic and often overlooked example is the importance of one on one meetings in any management structure. Andy Grove is most famously known for championing the importance of one-on-ones, asserting that any manager who doesn’t invest in one-on-ones for lack of time is making short term optimizations ー “Ninety minutes of your time can enhance the quality of your subordinate’s work for two weeks, or for some eighty-plus hours.” [1] Investing in the growth of the individual members of your team as a leader is your #1 priority and will yield the most returns.

“It is very important to grasp that… leadership is not just about humility and modesty. It is equally about ferocious resolve, an almost stoic determination to do whatever needs to be done to make the company great.” — Jim Collins in Good to Great [7]

Principles are fundamental beliefs; this set of principles represents strategies that leaders have historically proven to be successful. As a leader, your ultimate goal is to empower your team to do well. On you and your team’s journey to accomplish your mission, you will face a unique set of challenges specific to your goal that require unique methodology to tackle. To be a truly great leader, you must reconcile general principles, like the ones outlined, with your own methodology to overcome your distinct set of challenges.

— Josh Singer and Aneesh Pappu


  1. Grove, Andrew S. High Output Management. New York: Random House, 1983. Print.
  2. Blanding, Michael. “The 5 Strategy Rules of Bill Gates, Andy Grove, and Steve Jobs.” HBS Working Knowledge. Harvard Business School, 20 Apr. 2015. Web. Nov. 2017
  3. Napoleon Bonaparte, “Proclamations to French Troops in Italy (1796).” University of Pittsburgh. University of Pittsburgh, n.d. Web. Oct. 2016.
  4. Horowitz, Ben. The Hard Thing about Hard Things: Building a Business When There Are No Easy Answers. New York: Harper Business, 2014. Print.
  5. “Radical Candor — The Surprising Secret to Being a Good Boss.” First Round Review. First Round Review, n.d. Web. Oct. 2016.
  6. Malone, Michael S. Bill & Dave: How Hewlett and Packard Built the World’s Greatest Company. New York, NY: Portfolio, 2007. Print.
  7. Collins, James C. Good to Great: Why Some Companies Make the Leap … and Others Don’t. New York, NY: HarperBusiness, 2001. Print.


The key to a high output software engineering organization

After working on side projects and spending the summer at a tech company, I realized one of the most undervalued components of building things: flow.

What is flow?

Flow is that moment when you are so deep in whatever you’re working on, the periphery of the outside world blurs together. It’s such a satisfying state that it’s why many makers make things.

How do we hit flow? Many of us hit flow in different ways. Some find it through writing, others through running, and for nearly all engineers, we find it through building things. And when it hits, we are more productive than at any other time.

Flow can be stopped, too. Flow blockers include things like interruptions and mundane work. A flow blocker feels like that one person who walks in front of the screen at the climax of a movie.

What makes flow so important to an engineer is that when it’s hit, engineering turns from job to nirvana. Virtually any engineer can attest to the state of happiness that occurs when flow sets in. It’s like injecting yourself with a really potent drug. And that drug’s effects can be perpetuated by completing more work.

How do you help engineers reach flow, though? In my opinion, flow can be guaranteed for an engineer if three things are present: the ability to execute, the ability to test and see their progress, and the ability to have ownership in what they are working on.

Execution can be divided into two parts: being able to complete the work, and *being able to get the resources* to complete the work. When you are executing, you can complete work, and there’s little interruption or blockage. This lag isn’t to be confused with moments of thinking/difficulty. Rather it’s the unsolvable blocking or meetings that interrupt thought. If you start thinking like you won’t be able to execute or in the case of a meeting, you stop thinking at all, the anxiety will take over and block flow. And then there’s getting the resources to work. This is the ability to get whatever knowledge and resources are necessary to complete the work. Without this, execution can’t happen.

Testing and measuring progress is the second key. Seeing that console.log(“code hit here”); appear in the terminal buffer keeps you going [1]. It’s verification that you are executing correctly. A programmer’s logs are a lot like an airline pilot’s GPS. While in the air, a GPS can’t fly and land the plane for you. But it can tell you if you’re going in the right direction. When you’re coding, logs can’t write the code, but they can tell us if the code that we write is working. Logs give us immediate feedback and remove the uncertainty that can interrupt flow.

Ownership helps flow by giving purpose to tasks. Inherently, having ownership of a project psychologically attaches you to that project. And through that attachment, you feel the need to be an expert on your project. And to be an expert, you have to know what the goals of your project are better than anyone else. Rather than working on individual tasks, you (and your manager), establish the goals for the project. When a project has owners, it sets an agenda from the start, which makes it clear what needs to be executed. This clarity helps achieve the feeling of control over work, thus boosting performance and flow.

How engineering organizations can be conducive to flow

If you are an engineering manager/leader, I believe one of your top priorities is:

1. Helping new members of your team hit flow as soon as they can
2. Helping current members of your staff be in flow as much as possible when they work.

Enabling flow for developers both makes their job very rewarding for them and helps the output of your organization. As an engineering organization, there’s a variety of things you can do to help flow.

Both components of execution can be augmented. In regards to acquiring resources to execute, many organizations already have streamlined IT and plenty of snacks. Some great organizations have developer experience teams that create developer tools to boost productivity. However, any organization can do a better job providing access to information/resources for execution. Things like better wikis and more documentation play crucial roles in an engineer’s ability to execute and reach flow. Many engineering organizations trade off extra lines of code for proper documentation. In my opinion, quality documentation is crucial.

For many organizations, there are a lot of tools built in-house. Whenever an engineer has a question about these tools/code, they can’t google it. Rather, they either have to ask another developer (usually by email/slack) or look in a sometimes sparse, unorganized internal wiki site. And in these wikis, you may come across blank pages or four-year-old scribbles vaguely associated with your query.

In regards to actually doing the work, organizations can reduce the lag time to gain approval to execute on certain items and schedule meetings using maker time.

The ability to continually test the progress of your execution is a huge advantage in a software engineering organization. If you can compile and run your project and have access to a great logging system, the testing component of flow figures itself out. Knowing your code is functioning without having to deploy to production/staging server (depending on how your organization deploys), wait thirty minutes, and then look at the logs on a crummy interface makes the biggest difference. It all comes down to feeling control over the code. If engineering organizations put time into giving engineers significant resources to continually test their progress, engineers will feel more confident about the code they write and will be more likely to enter a state of flow.

Organizations can help give ownership in two ways: quantitatively and qualitatively. Using numbers can help engineers feel ownership. Metrics and percentages of impact can help engineers value their project. More subtly, though, an organization can qualitatively give ownership to engineers.

For example, I believe that a micro-service architecture rather than a big, monolithic codebase encourages ownership. That is, having the ability to have your own mini codebase, package it up into a complete, independent project, and name it to your pleasing provides increased ownership. It’s like the difference between working on a big boat and having your own boat. When you have your own boat, you name it proudly, furnish it using your styles, and protect with your life. And who doesn’t want their own boat?

Thanks to Dan Isaza, Chris Barber, Aneesh Pappu, Tony Bruess, Niko Alino, and Yonatan Oren for reading/listening to drafts of this.

[1] A log is a statement you write in code that gets printed to your screen when the program runs. Logs are used to see what a program is doing and to help see if certain pieces of the code are working.

Five things I wish I knew earlier about communication

We all underestimate the importance of communication. Communication is how we interact with the world. All we have are other people’s words to go off of in understanding what others are thinking, which is why it’s important to communicate the right sequence of words. I use the following five tactics as much as I can when communicating.

1. Using the right coordinating conjunctions

A coordinating conjunction is a word used to connect two ideas together. The coordinating conjunctions are “for, and, nor, but, or, yet, and, so”. I find that when conveying a point using the right coordinating conjunction can make the biggest difference.

For example, there’s the classic “use ‘and’ over ‘but’” tactic. Both words convey the same idea; however, “but” negatively implicates while “and” does not. See the difference here:

I went to the bank, but I forgot to pick up the checks.
I went to the bank, and I forgot to pick up the checks.

Both are nearly identical. However, the latter option helps you keep face as a communicator.

2. Powerless communication

When trying to have my ideas heard in small groups where someone is dominating, I use words like “maybe,” “might”, and even “um.” By adding these qualifiers, I communicate that I’m trying to help our group rather than trying to dominate it.

“We should consider this other strategy for the backend.”
“Maybe we should consider this other strategy for the backend?”

The latter sentence is much more favorable when proposing a new idea in small groups. For the record, this strategy isn’t applicable everywhere. For example, don’t use these words when giving a speech. However, do use them when you initially join a group and are trying to have your ideas heard.

3. Use the words “perceive”, “feel”, and “seems"

Three words that my friends recommended to me are the words “perceive,” “feel”, and “seems.” All these words signify that you are talking about your emotions, rather than what may be factual. Telling a roommate “I feel like you don’t care about the cleanliness of our home” rather than “you don’t care about the cleanliness of our home” makes it easier to have a dialogue. It’s impossible to argue with how you felt.

4. Signify you are listening

And listen more than you speak. Communicating is a two-way street, and effectively communicating is letting the other person know that you care about both directions. By asking particular questions like “why do you believe ___ to be true?” and “So you are saying that ___?” are great ways to both a) demonstrate that you are listening and b) understand the other person better.

5. Ask others for things you want, rather than what you don't want

When you are working with someone else, emphasize the things that you want from them, rather than what you don’t want. When you request things you don’t want, you’re negatively implicating your request, which makes it harder for the other person to do the thing you actually want. For example, a professor wants his/her students to know a concept. Rather than requesting the students not to use their laptops, he/she should ask that the students pay close attention to the following information.

Finding and Aligning Incentives

I see this type of post a lot on Facebook:

I look at this post, and think “What a cool offer, let’s see what this service is.” Then I decide to check out the product, and I realize that the person who posted the status gets an incentive when you sign up using their code/link. It happens a lot, but there’s something much more profound to incentives than free Uber credits and access to betas.

What are they

Incentives are things that motivate people. You can categorize most incentives as financial, moral, or natural incentives. Financial incentives fuel our desire for wealth; moral incentives appeal to our principles; natural incentives act on our emotions. An example of an incentive is a bonus or commission on a sale.

Many of our day-to-day decisions revolve around incentives. You may be more productive at work because a raise incentivizes you. Or you may go to your religious institution because you are incentivized to be morally aligned (or are perhaps socially). Incentives help make up who we are, so it’s important to have an understanding of how they work. And an awareness of incentives can help you understand why people do certain things.

Recognizing Incentives

By knowing your own internal and external incentives, you will be more self-aware. And if you know the internal and external motivations of the people around you, you will know why people do certain things.

Recognizing your incentives is relatively straightforward for financial and moral incentives. Just make a list of how you spend your time and money and work back from there to infer your incentives. It’s a little bit harder for natural incentives because it requires some understanding of your own psychology, but good indicators are your emotions (e.g. curiosity, anger).

Once you can recognize your incentives, you can start identifying other people’s incentives. It’s relatively easy to notice most other people’s incentives because they are probably similar to yours. [1] Knowing how to identify an incentive structure is much different than actively recognizing incentive structures in your life, though. It’s the difference between knowing how a bike works and how to ride a bike. If you want to actively recognize incentive structures, you have to practice it repeatedly. Some strategies for actively identifying incentive structures are asking “Why did ____ make that decision?” or “What is the goal of ___ in this deal?” After a few what’s and why’s, the incentives of a person/group are elucidated. But the real art is differentiating what the actual incentives are in a system from the seemingly true incentives.

Seemingly True Incentives

These sorts of incentive structures exist all around us, but they are sometimes hard to recognize because we assume incentive structures operate efficiently. An example of determining a true incentive structure is Medicare’s drug reimbursement policy for medication given in the office. In this system, it seems like a doctor’s motive is your health. But your doctor may be incentivized to prescribe you a higher costing drug than a generic drug (a drug with similar effects) because they make more money from the higher costing drug.

Online news (and a lot of news in general) is another example of a perverse/convoluted incentive structure. It seems as though the incentive of the news is to provide the best reporting. But in fact, it usually isn’t. Because clicks-throughs financially reward online content, many writers optimize for click bait. And most things that are optimized for clicks are not optimized for reporting the truth. Rather, it’s about fighting and capitalizing on our limited attention span. When you realize that the news sources you trust make money off clicks, you will have a better sense of what may be true and what may not be. [2]

Aligning Incentives

Although perverse incentive structures may make you distrusting of people, particular incentive structures can be quite productive.

Some of the best incentive structures to exist are in high-performing companies. For a company to be truly successful, many different incentives have to be aligned from the company’s inception to both fuel success and to reduce issues down the road.

Say you have four potential employees that all have different incentives. Employee #1 wants a lot of money. Employee #2 wishes to work on things that have high utility. Employee #3 intends to work with the best people. And Employee #4 desires to work on hard problems. In a company, you can align all these different incentives pretty easily. You can appeal to Employee #1’s desire for money by offering equity. You can appeal to Employee #2’s desire for utility by choosing the right problem for your company to work on. You can appeal to Employee #3’s incentive to work with the best people by offering recruiting bonuses to those in the company that source and recruit the best people. And you can appeal to Employee #4’s incentive to work on bold work by having a moonshots program and 20% projects. [3] All these seemingly different incentives can be aligned very well. And the more aligned the different incentives of a company, the more likely that company is to be successful.

On the other hand, a company can be an example of a structure with many misaligned incentives. For example, you may want to work on a hard, long-term problem, but your co-founder isn’t incentivized to work long term. A classic case of this is Ronald Wayne, a lesser-known co-founder of Apple, who left the company after two weeks. [4] Another example of misalignment is if your employees want to exit quickly, but as a founder, you want your business to go public. Many of Facebook’s first employees had incentives that didn’t align with Mark’s. When Mark decided not to sell Facebook in the early days, many of those initial employees decided to leave the company. [5] Just one misaligned incentive can put a company in gridlock, or even worse, cause these stressful situations to bubble up later on in the future.

If you’re trying to be an exceptional founder, a skill you may want to work on is identifying and aligning incentives. Just one misalignment can cause a potentially huge headache for your team down the road. But if you take some time initially to figure out what everyone is motivated by, you can build your incentive structure to avoid potential impasses and to foster your company’s growth.


Thanks to Josh Browder, Richard Chen, Aneesh Pappu, Yonatan Oren, and Chris Barber for reading drafts of this.

[1] In some situations, it can be difficult to know incentives that are intended to be discreet. Many would point to politicians as having more discreet incentive structures.

[2] Trust Me I’m Lying, from what I’ve heard, is an excellent book on how the media can operate perversely.

[3] Google X is an example of an initiative for moonshots. Many companies also implement 20% projects.

[4] https://www.washingtonpost.com/business/get-there/what-if-you-sold-10-percent-of-apple-in-1976/2016/04/15/9f64f4f4-00e3-11e6-9d36-33d198ea26c5_story.html

[5] http://www.themacro.com/articles/2016/08/mark-zuckerberg-future-interview/

How to read as much as you can (or at least how I do it)

In high school, I read blogs and long reads online. Freshman year, I read books instead. I noticed that I just couldn't read fast enough. So I built a workflow for reading/consuming as much content as possible. Disclaimer: I'm by no means a productivity guru or anything of the sort. It was just a big enough bother that I decided to create a system.

The System

I use five technologies to help me source & get through content: Twitter, Email, Instapaper, Audible, and my Kindle. 

Twitter helps me stay up to date on what's happening in the world as well as what is popular (that would otherwise be unpopular). For example, a random new VC may write a great post, but because I haven't subscribed to this VC, I wouldn't get it in my inbox. Twitter helps me find those sorts of reads. Then, I save to my Instapaper for reading in batches.

Email ensures that I have a one-stop shop for all the reads that I care about. Blog subscriptions and similar news sources (The Information) go there. I'll glance over them and decide how to categorize. Either I'll save it to Instapaper if it seems relevant, read as soon as I get it (if it's super relevant), or archive. I have to check my inbox regardless, so it eases the process. 

Audiobooks are usually for books that I want to read for a purpose other than personal development. For example, a new friend may recommend a book, and I want to show them that I care for their recommendations, so I'll download the book to Audible. These books are not high enough priority to dedicate reading time, but it's important to have the knowledge. For non-fiction, I'll listen to books at around 2-2.5 speed, and for fiction, I'll listen to at 1.25-1.5.

Kindle is for books that I place at the highest priority. If I'm reading a book on my Kindle, I'm probably highlighting and taking notes to instill what I learn and to review later. 

The benefit of all of these is methods is that I can study the content periodically. Instapaper allows me to highlight what's relevant and saves the highlights. Kindle highlights are exportable too. And for audiobooks, I'll go back and read a summary to cement the material.

I used to read everything either on my Kindle/Twitter, but I realize there's just too much good stuff out there. I needed to have a system to be more effective.

How to spend your time like an investor invests

I reason about the world using mental models. Simply put, a mental model is a tool for interpreting the world. [1]

As a college student, I make lots of decisions about how I spend my time. I want to have the highest returns on my decisions possible. I use my “asset allocation” mental model to help choose better time investments.

Asset Allocation

Asset allocation is an investment strategy that aims to balance risk and reward by apportioning a portfolio’s assets according to an individual’s goals, risk tolerance and investment horizon. [2]

Before deciding on what I should spend time on, I assess my options. I make time investments like how an investor would allocate assets. 
 
I categorize all the potential time investments as asset classes. As each asset class has a different risk level, each potential time investment does as well.

My portfolio

Fixed Interest

There are plenty of activities in college that have fixed return. Most college courses, for example, have fixed returns. If I invest my time into Linear Algebra, then my return will be knowing how to do matrix transformations.

The risk in courses is little to none if you wouldn’t use the new knowledge till after graduation. In my case, most courses I can take during another quarter or self-study online. [3] 
 
I recognize the importance of my fixed interest activities in maximizing value out of my life. But if I’m trying to have incredibly high returns on my investment of time, then I have to diversify and take risks.

Equities

Equities have more risk than fixed interest activities. You can have higher returns from an equity activity than a fixed interest activity, but you can also have lower returns.
 
Joining an extracurricular is an example of an equity. You could join an entrepreneurship organization and get to meet motivated people. But it could also be run poorly and waste your time, which could have been spent doing something else, like studying for a class.

Make sure that things you think are fixed interest aren’t actually equities! For example, a college course may seem like it’s fixed interest, but in reality, it can be an equity. If you meet great people in the class, then your investment had much more upside potential than a fixed interest activity. Then, choosing classes with great people is the real risk, which is higher than the risk in learning the wrong thing. [3]

One of my favorite personal investments that had immediate return was joining TreeHacks; I met a ton of cool people. I also had high returns from working with Matt Mochary, where I learned a ton about management and sales. Last but not least, I highly value building side projects with other awesome people, where I made great friends and became a better programmer. All these had high time investment risk, but in the end, they were tremendously impactful.

How I optimize for expected value

I aim to have a balanced portfolio that optimizes for expected value from my investments.

It’s important to have fixed interest activities to offset the risk from your equity activities. For example, I study for my classes in case my projects fall through. But it’s also important to have equities if you want to have potentially high returns.

Another thing I take into consideration is compound interest; it’s a type of interest that reinvests itself. [4] It plays a major role in choosing when you’ll invest your time into something. If an activity will completely change your perspective on life (in a positive way), you may want to invest in that activity rather than another activity that is fixed interest. That way, you’ll have compounding returns as you invest in new activities as a result of the new perspective.

Certain activities, like reading a book on how to learn better, have compounding returns. When you take a new course, it will be easier to learn because of your new knowledge. And you won’t have to use as much effort (capital) to invest and get returns, which means it’s a better time investment.

If you have a balanced portfolio, you’ll get better returns than the rest of the market (your peers) who may not have an asset allocation plan at all. And because time is limited and exponentially shrinking, it’s best to have a spending plan for it.


Thanks to Aneesh PappuMike YuChris Barber, and Rohan Pai for reading drafts of this.

Notes

[1] If you want to learn more about mental models and the popular ones, read Poor Charlie’s Almanack or this piece by Gabriel Weinberg

[2] http://www.investopedia.com/terms/a/assetallocation.asp
 
[3] However, if you take a course that would change your perspective on a problem (i.e. in college), then not knowing the material in a course can be risky. It’s all in how you frame the time investment.
 
[4] https://en.wikipedia.org/wiki/Compound_interest