Dear School, Please Teach My Son How to Fail

Tom Waits: “My son is older than me” (1:37 in the video)

This year my son turns five and with the earnest naiveté of a rookie father, I began to visit various elementary schools in Palo Alto, Menlo Park, Hillsborough, and Los Altos a few months ago. I was quickly introduced to the confusing array of choices in front of a parent – public, choice, Montessori, Waldorf, Academies, schools for the “gifted & talented”. The last one is particularly mysterious – the school in question actually tests your five year old to determine if they fit that definition.

As I visited these schools and asked for in-classroom observations vs. hearing a pitch by a teacher or administrator, I could not shake a deeply unsettling and sinking feeling every time I saw teachers engaging with children. As I have thought more about it in recent weeks, it is clear that there is a fundamental fracture in the approach to education and the needs of this generation for the next few decades.

By the time this generation of elementary school kids is ready to go to work (2027-2045), their world will change at a faster pace than ever, multiple career changes, and multiple technology changes will happen. Our own generation has seen a very rapid pace of change occur in the past two decades and the rate of change is only going to accelerate I believe.

Sobering thought – schools (elementary, middle, high, university) will not change fast enough as our kids grow up. I don’t really expect to see changes in structured education in the next ten years. As a result, helping the kids learn these skills is how the parents can complement whichever stream of learning the kids are going through.

Examining the various approaches to education against this realization makes it clear that what’s required is not identifying and pushing just one aspect of education – we have to ensure our kids learn how to learn.

For this generation, the key skills will be:

Creative learning. Creativity is not just an outbound expression of our thoughts. It is also the way we receive knowledge and learn to appreciate all aspects of an experience.

Social learning. Group learning is often undervalued in our current systems of education though if we believe our kid’s world will be dominated by needing to learn things not yet in organized curricula, it is clear that group or cohort dynamics will matter a lot more than they have in the past. Communicating learning and imparting lessons learnt to others in the cohort is a key part of learning beyond the boundaries set by institutional education. Each member of the cohort needs to be a teacher and co-learner. Your child’s cohort will curate their learning constantly.

Flexibility. Cross-disciplinary learnings and applying lessons learnt in one domain to others is already yielding amazing results in diverse fields. As an example: doctors of tomorrow need to know Information Theory as well as how to code (CS) in order to decode the mysteries of our genomes and genomic systems. Probability is not just for information theory and macro-economists, but for designers, psychologists in addition to scientists and engineers. Anyone who has read  Kahneman can see lessons in that field of study influencing consumer behavior online.

Failure as a fundamental ingredient of success, not an outcome to avoid at all costs. The vocabulary around failure needs to evolve and change over the next decade of their life. This one is clearly the skill they will need the most. Multiple career changes will be the norm and even within a career, failure as a key tool for learning will be invaluable to learn fast. Curricula and courses (structured education) will not keep pace with innovation and they will have to learn their craft by themselves with fast iterations, fast failure, and fast learning.

The schools I have visited in the SF Bay area seem rooted in the philosophies of US zeitgeist of 50s and 60s and it is clear that most teachers today were in their formative years in 70s and 80s, when the pace of change for them did not include the degree of connectivity we have today. Clearly, teaching the lessons of 90s and 00s hasn’t happened yet but it will be required for the current generation of children entering schools.

A personal example – at engineering school I studied fundamental sciences and various “engineering” courses including Acoustics, Tensors, Microwave Theory, Televisions & Transmission Theory as part of the EE curriculum. Through the 60s-70s-80s, this education would have trained an engineer for a lifetime at Bell Labs or Bell Northern Research or GE. Today, other than Fundamental Physics, Chemistry, and Mathematics (Tensors ftw), 3 out of 5 years worth of specialization have not survived. Even the stellar courses of my grad student life – signal processing, optical transmission, networking, lasers are obsolete within 10 years except for the foundational courses of Probability Theory and Information Theory.

For our children, everything they will “know” is wrong – in the sense it won’t be the primary determinant of their success. Everything they can learn anew will matter – forever in their multiple and productive careers.

Beginning with fundamental science (Physics, Chemistry, Mathematics, Computing), this new generation will require a ‘lean’ way of learning. As a rookie parent, I believe this is where schools can help them learn creativity, flexibility, and a lasting love of failure as a tool.

Picking Advisors for Your Startup

Somewhere in the entrepreneurial journey from an idea to a startup, founders will often meet friends and colleagues to brainstorm and develop their ideas. In some of these conversations “Oh I think you should meet XYZ person who’d be great for feedback” event happens multiple times. Some of these people are potential advisors for your startup. Here are some thoughts on how to think about advisors at various stages of the idea-to-company odyssey.

Remember your Advisor’s job is to help you make non-obvious choices in the face of imperfect and sometimes non-existent data. Recruit accordingly.

The Six Cardinal Directions of Effective Advisors

1. The most important skill an advisor can bring to you and your idea is a way to improve your idea by asking you the right and often ‘hard’ questions. People who want to replicate the success they had even if in the same area as your startup by repeating the same approach/execution/recipe are not the right ones for you. Beyond the usual “Oh Its nice” or “Its great” responses, listen for something that signals that your idea made them think. If they then come back with questions you haven’t yet asked yourself, they may be a good match as an advisor.

2. Don’t confuse mentor with advisor. Mentors are a rare breed of individuals. They are good at asking questions and making you learn regardless of what they or you are working on. Conflating the two may not necessarily be good for you or your  startup.

3. How do they talk about failure and what they’ve learnt from the failure matters as much as what they’re successful at. Ask them what they have learnt in the last three years as a result of a failure that has now changed their thinking or behavior in a meaningful way.

4. Make sure you ask them if they have played the role (paid in equity usually) with at least one other startup. You want to ensure that they are not going to play ‘Product Manager’ for you with good intentions and potentially disastrous results. Advisors are not going to invent your product or your market or your product-features. They can be invaluable in pointing out the voids in your product strategy or feature-list or competitive dynamics. Advisors who are good at pointing out what doesn’t exist are often far more helpful than the ones who suggest a specific feature or two.

5. Ask them for a specific commitment of time, effort, and introductions you expect from them over the first year of your collaboration. Introduce them to your other advisors and create some opportunities for them to collaborate – enabling them to think beyond their usual domain is effectively delightful compensation for them beyond the equity you will give them.

6. Your advisors are not your investors. Keep these two roles separate. While there may be some overlap, they have distinct responsibilities for you and your startup.

The Entourage Approach

For certain startups and founders, an ‘entourage’ may be more appropriate which functions as early adopters and influencers in your marketplace. Perhaps the best example of this approach was where @tonysphere and other founders were well connected and signed up 26 advisors to help them push to a million users within a year and an acquisition by AOL. If you’re not as well connected as the fine folks at, this may not be the way to go. A weak entourage is baggage, not balloons.

Advisor Compensation

I will write about Advisor compensation in a future post but here are some guidelines for silicon valley startups:
for early stage (between idea stage and funding) formal advisors, expect to share about 1% equity which goes down to approx 0.25% for seed-funded startups and often between 0.1 and 0.25% for developing stage startups. Typically the equity vests monthly over a year without any cliff and there is no other compensation (e.g. cash).


A block away from where we live, I have walked by Maria’s home for ten years. Sitting on her porch on most days, I got a friendly wave, a big smile, and an occasional comment on the weather as I walked by. A few years ago when our son was born, we would often stop with the stroller at her porch and affirm whether the weather was nice or warm or too hot or too cloudy.

At two when he learnt to ‘scoot’ on a balance-bike, the slope up to her porch from the sidewalk and down again was his first attempt at tackling speed. A couple of times she brought out little toys for him – a doll (for the longest time she thought he was a girl given our son’s long hair before his first haircut just before his third birthday), a small troll, a tiny car. Our son graduated to a pedal bike last summer and his trip up and down the porch got faster every time we walked by. Maria would let out a hoot of excitement every time he would accelerate down the small walkway on his bike, swerving at the last-minute to turn on to the sidewalk.

Sometimes we’d see her on the other side of the street with a group of apartment dwellers who had a Friday evening get-together out on the sidewalk every week in Summer. Firmly grasping the wine glass in her hands, she always had a smile and sparking eyes looking at everyone who walked by.

Conversation was limited with her limited English and our nonexistent Polish.

A few months ago after I came back from a trip to India I noticed Maria wasn’t at her porch and the house seemed locked for weeks. But it was winter time and I thought nothing of it.

A few weeks ago, I saw some people were moving furniture and belongings out in to a large trash container.

I haven’t seen Maria since late fall last year. Last week I saw someone left flowers on the sidewalk in front of her house.

Maria doesn’t live there anymore.

Facebook Lessons for Startups & Founders

Facebook filed their S-1 with SEC on February 1, 2012 and triggered yet another round of discussions in the valley digirati and digirazzi alike.  From computations of founder stakes to opinions on investment, tech and popular media made sure no one missed any aspects of the filing.

So what does it mean (If anything) for current and future founders of tech startups? Success at this scale – adoption, financial success, and pioneering a new segment of communications is rare and deserves much praise. The founders in this case – from Zuckerberg to Parker, Moskovitz, and even the Winklevii deserve all the praise they get for playing a role in the success.

Your first few employee matter a lot more than you think

I would also like to point out the critical role played by the first tens of engineers (hackers if you will) in building Facebook. Less heralded and often ignored all together by the media, this corps of engineers in my opinion deserves as much praise as the ones grabbing headlines in the press. Without the efforts of this group, Facebook could not have made it – founder foresight/passion/skills notwithstanding. Referred to as ’employees’ this group is as much of a co-founder as ‘the founder’ himself. They took nearly the same risks, likely contributed as much to product, platform, and technology, and helped it get from its early success to a product whose expansion beyond .edu domain was one of the most eagerly awaited consumer product introductions ever.

For founders, the aspects worth emulating aren’t the ones highlighted by blogs and media today – try and focus on the early parts of the arc of Facebook’s success. You will find many of the traits espoused by Eric Ries and Steve Blank when you examine the first year or so at Facebook (2004-2006). Some of the ones that stood out for me:

Build fast, release early, Find your Market-fit.

Famous for putting out the first iteration of the kernel of ‘TheFacebook’ in a week, this is a great example of lean development and testing market-fit. It wasn’t the first iteration either – Facemash which was a hot-or-not style site/application that Zuckerberg built prior to Facebook at Harvard and saw immediate adoption. Remember that hot-or-not was a circa 2000 phenomenon and Facebook’s first iteration was in 2004.

Focus on Users; user-adoption, user-experience.

In 2005, the valley was hearing whispers about Facebook and how Accel “went and got the deal” at an unheard of valuation (remember we were just coming off the dark years of 2002-2003), no one talked about Facebook’s technology or its platform or how it may one day be the dominant social-connector and app-platform.  But the first line one heard about Facebook was how many users they had, how much time these users were spending on Facebook, and the rapid growth rate that was easily the highest for any consumer app. This was a dramatic contrast with Google where the talk was about the outstanding infrastructure and how that gives them a unique advantage vs. everyone else in search and advertising. Unless you are building an application that needs to invent new systems and infrastructure, stay focused on users. Adoption will enable you to invent a platform and plenty of technology once you’re successful.

Surround yourself with people smarter than you

Graduating from a Harvard dorm room to University Avenue in Palo Alto, Facebook continued to find and learn from some of the best in their domain – whether it was Zuckerberg learning from Don Graham (Washington Post) or the stellar list of its board members and investors, it didn’t just happen by accident. I am not saying Zuckerberg is not smart, I am saying one of his smartest moves was to find people smarter than him at that point in time about an aspect of his startup. For founders, the clear lesson is find and pitch the smartest people you can find. I suggest a simple approach to accomplishing it:

When you meet prospective VCs (Partners or Associates) or Advisors, ask them to introduce you to two other people that they think are the smartest in the business.  Be persistent and chase down these introductions, turn them in to meetings, and ask them to introduce you to two more in turn.  In a few months you should be able to meet with enough people to learn from and who can be potential investors, advisors, or informal-advisors to your startup.

Think long term

This one is the easiest point to state and the hardest to follow. I believe there is a fair value at every step for a startup  if they have taken angel/venture money. And  they must be responsible in considering any offers that come their way. I also believe there is much (realizable) value in finding a way not to take that offer. Each such situation is unique but do consider that if you can find a way to build more value, you will have a chance to deliver life-changing rewards for yourself, your team, and your investors.

You know what’s cool? A Billion users. 

Building a startup that delivers a Billion+ in profits eight years after starting is Cool. But do you know what’s really cool – that Zuckerberg’s efforts changed and enriched the lives of thousands of employees and millions of users. A founder’s measure isn’t the capital they return or create, it is the number of lives they touch, improve, and change.

If all you wanted to make was money, there are easier paths to realize that goal. Be a founder if you want to make a difference. Money will follow.

On Startup Values

In Silicon Valley, ‘startup’ is one of the most common and the most valuable word one hears about town. Freely bandied about by those who were once in a startup, are currently in a startup or want to start one, the word is a badge of pride for those who have experienced it.

Less understood is what goes in to creating, sustaining, and growing a startup.  Founders, money, employees, investors, technology and products are necessary but not sufficient ingredients for startup success. One of the crucial ingredients one rarely hears about and is usually not understood by most is Startup Values.

Values is not capital you can raise from VCs. Values are reflected by a few critical qualities founders and startup employees must either have or recognize and cultivate. Values are not transplantable a few months or years in to the journey. More than a few (very smart) founders I know dismiss it by saying “We will focus on values once we’re successful”. Wrong! Startup values are like a seed you plant on day one alongside your ideas and it needs the same care and nurture as your technology and products.

integration symbol

I have always felt that the key startup values are:


Honesty in a startup primarily means interpersonal honesty between all the employees. Honesty is also the fabric that links objective measurement of a startup’s progress along chosen metrics and the startup’s stated goals.  In between founders and employees and between multiple founders in the case of cofounders, honesty is the only way to sustain a working relationship.

How to get it right: Communications is a key component of honesty. Founders and CEOs must ensure everyone understands where they are, where they are going, and how they are going to get there. You can never communicate enough and email is perhaps the poorest mode of such communication. In a small team, a 5 minute sync meeting every day or 15 minutes every week should suffice.

How do you know its not working: When you find yourself ‘marketing’ or spinning the truth to your coworkers, you must have the courage to admit you’re not being honest. In a startup context, some typical phrases that should serve as warning signs include “It will be easy to raise money”, “Hockey stick growth is just a couple of features away” or “We can always acquire users through advertising” or “There will be lots of buyers for the company if you get to X number of users”. When employees hear such things from their CEO or founders, ask questions. If startups hear such words from their investors, take a long hard look at their track record and at your balance sheet.


In a startup, you often recruit friends, referrals from friends, and those you respect to the mission at hand. Flexibility doesn’t just apply to founders/CEOs but to everyone. Venturing in to areas adjacent to your area-of-comfort as far as your skills go will be often required. A good startup team at work is like an ongoing game of 3D twister. Flexibility, once it becomes part of your startup’s DNA, makes it better at evolution as well as adapting to challenges.

How to get it right: Be open when CEOs/founders ask you to do something beyond your area of expertise or experience. Voice your fears openly, express your challenges clearly. Ask for help when you need it, offer help when you see someone needing it.

How do you know its not working: When you hear CEOs/founders/employees express “Thats not what I was hired for”, it should serve as an early warning sign. If your startup is not good at handling failure (see below), it will be hard to build a culture of flexibility.


A startup is (most of the time) an irrational pursuit with a high probability of not following its initial trajectory. Creativity, exercised at all levels from infrastructure/technology to design & delivery, is the most powerful value you can have to combat existing products you compete with or to highlight the one thing you excel at versus all others. It is an essential part that improves flexibility and helps a startup to navigate competition that may be better capitalized or entrenched. At a personal level, creativity is an everyday expression of how things get done in a startup with limited resources and money.

How to get it right: If a startup, prior to success (users or revenue) can point to something unique that they do that others do not, it is likely creativity that is at work.

How do you know its not working: If your coworkers, founders or CEOs talk too much about “This is how I did things at company XYZ” when it comes to talking technology, products, or your market, you should fear that your startup lacks creativity. More than any other area, past work is really not a good indicator of the future in startup.

Failure with grace

This is perhaps the most talked about ‘lean‘ (e.g. smart) aspect of a startup’s journey from idea to success and may be the most misunderstood. No one likes to fail even though fail-fast, fail-often, fail-early is an easy set of words to say. I believe failure with grace is not just for complex systems. Seemingly trivial interactions between team members are often predicated on success, not failure and unless everyone in the team in a startup can freely (and honestly) express failure, re-calibrate, and have a chance of re-delivering, each failure will be costly in an interpersonal sense.

How to get it right: All employees must be comfortable in saying “I failed at XYZ and here’s how I am going to get it right”. When there is no interpersonal unease or ‘cost’ to saying/hearing it, you will know your team is on the right path to integrate failure as a navigational mechanism to find the right direction.

How do you know its not working: When someone in the team fails ‘silently’ at a task or two and begins to find excuses vs. ‘claiming the failure’ is a dependable sign of lack of this startup value. Silent failures are deadly in all kinds of systems, and deadlier in a startup.  A failure not owned at the first sign of it is a toxic seed that will threaten startup success.

Measurable heuristics

Every startup is based on a few early ideas about how their world ought to be. Startups must be honest with themselves to figure out the right measurements for their heuristics about how their product will evolve.  Measurement and heuristics are the yin and yang of startup ideas.  One cannot exist without the other or has no meaning without the other.  A right balance between these two is often the hardest value to get right in a startup.  Too much heuristics to guide you may mean unconstrained wander before you find your market while too much measurement will surely constrain good thinking with possible false positives and negatives. Measurement confirms innovation, but rarely initiates it.

How to get it right: Teams must have the discipline to listen to measurements for determining growth and listen to heuristic thinking to set the first vectors for experimentation.

How do you know its not working: Each discussion of a new feature, product, or change must be accompanied by “how will we know its working” discussion. Success is not pornography that you will know it when you see it. If you cannot measure success, it is likely you do not yet know how to go to there.

I hope you found something worth thinking about in this post and I’d love to hear from you (comments below or tweet  @rohit_x_).

In a related future post, I will be writing about working with VCs that share these values and help your startup enhance them.

This work is licensed under a Creative Commons Attribution 3.0 Unported License.