Everyone agrees high standards matter. The challenge is acting on them, because maintaining a high bar almost always means inviting conflict. Most of us aren’t wired to embrace conflict, so we hesitate. The real hurdle isn’t setting the standard; it’s refusing to lower it when things get uncomfortable.

Here are three lessons that have shaped how I stay determined.

Lesson 1: People want a demanding bar.

In my first company, we signed our first customer while mid-pivot. They liked the product but asked for several new features.

Instead of signing them as-is, we promised to build every feature within a few weeks. The team worked around the clock and delivered. That customer became a key reference and stayed through our eventual acquisition.

That sprint left a lasting pride. Ambitious goals don’t just test people—they energize them. Set the bar high, give support, and teams often surpass their own expectations.

Lesson 2: Higher standards stick when paired with respect.

At one of my companies, a teammate kept slipping deadlines. I dreaded the conversation, but I invited them to lunch instead of a curt video call. We talked about their career goals first, then I explained why we couldn’t continue.

They surprised me by saying, “I’ve been feeling it too. Thanks for being straight with me.”

We parted on good terms, and I later referred them to a better-fit company. You can insist on excellence and still treat people with dignity. Respect doesn’t lower the bar; it makes it sustainable.

Lesson 3: Others have high standards for you.

While fundraising for my third company, I pitched an angel investor introduced by my lead. The meeting felt great—I was already thinking about allocation. Hours later, I learned they’d passed.

Their feedback: “I assumed you’d be presentation-ready—you seem so polished in your writing.”

That was a gut punch. While I thought I was being “authentic,” I came across as unpolished. They expected excellence because that’s what I’d promised in every email. Customers, investors, teammates—they all notice when you don’t meet the standard you set.

High standards aren’t about perfectionism—they’re about trust. When you show that the bar is real and you’re willing to face the discomfort of holding it, people rise with you. The hard part isn’t setting the standard; it’s refusing to lower it when things get messy—and that’s what builds something enduring.

Afterward, one of our investors sent me this tweet:

The investor was right. I was quick to pivot—and for good reason. Though I’d spent years following Crypto, I’d never built a Web3 product or deeply understood the customer profile. I hadn’t lived through a “Crypto Winter,” so when FTX imploded and the market collapsed, I gave up on Crypto. I lacked conviction.

What followed was humbling. My team and I spent six months exploring different markets and business models, testing ideas that didn’t stick. It was frustrating, but it eventually brought us back to Automotive—the industry where I’d built my previous company. Things started to click. Within a few months, we developed our technology and acquired our first pilot customer. It took time to regain our footing, but this time, there was one critical difference: I had conviction.

Conviction in start-ups isn’t just about believing in your idea; it’s about understanding why it matters and why you’re the right person to solve the problem. It’s the fuel that keeps you going when setbacks hit—when deals fall through, funding feels impossible, or competitors move faster. And it’s contagious. Conviction inspires your team, attracts investors, and reassures customers that you’re committed for the long haul.

Looking back on my time in Web3, it’s clear I lacked that kind of conviction. Sure, I was excited about the potential of blockchain, but I wasn’t immersed in it. I wasn’t living the customer’s pain points or seeing the problems firsthand. So when things got tough, I walked away. It wasn’t just a lack of discipline; it was a lack of alignment. I was chasing a market because it was hot, not because I was convicted.

In contrast, when we pivoted into Automotive, it felt like coming home. I’d spent years in the industry, working alongside the very customers we’re now building for. I understood their frustrations, their priorities, and their language. That familiarity didn’t just give me confidence; it gave me a foundation to build on. And with that foundation came conviction.

Conviction sharpens your focus. In the early days of a start-up, distractions are everywhere—shiny ideas, tangential opportunities, tempting shortcuts. Without conviction, it’s easy to chase everything and accomplish nothing. But when you believe in what you’re doing, you learn to say no. You stay the course, even when it’s hard. Especially when it’s hard.

That’s not to say conviction guarantees success. Start-ups are risky, and there are always factors beyond your control. But without conviction, you’re almost guaranteed to fail. When the tough moments come—and they always do—conviction is what keeps you moving forward.

Today, AutoTrainer (rebranded from Anomaly Labs) is thriving in Automotive. The journey from Crypto to where we are now was long and messy, but it was worth it. I’ve learned that conviction isn’t optional in this game; it’s the foundation for everything. Without it, even the best ideas will crumble. With it, you can weather storms, inspire others, and build something that lasts.

Conviction doesn’t make the path easier, but it makes it possible. And in the end, that’s what matters.

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I borrowed this idea from my favorite business book - Integrity by Henry Cloud. It means that no matter how difficult it is for us to accept, we are always better off knowing the truth. Once we embrace the truth, we can often address our situation very effectively. Usually, we need to get to the truth to be able to address our situation at all.

It sounds simple, but it’s not easy. I say this because embracing reality is not a default human behavior. Honestly, our default behavior is to be dishonest with ourselves.

For example:

• The sales leader who isn’t hitting their sales numbers believes that “it’s only a matter of time” before their leads turn around and convert.

• The founder is almost out of money but is in conversation with interested investors. If “just one” of these investors signs, the company will be flush and back to a growth trajectory.

• The manager with a report is an exceptional contributor with an awful attitude. If the company starts doing well, the manager thinks, the attitude problem will “fix itself.”

What all of these stories have in common is hope. In every situation above, a heroic tale was available where the problem fixed itself. Also, in every situation above, hope was not a strategy. In my experience observing start-ups, I never saw a problem like this “fix itself.” The founders either fixed it, or the company went under.

As a coping strategy, it’s much easier for our egos to tell ourselves a heroic tale than to accept a humiliating reality. I think it’s much more courageous to make reality your friend.

I once advised a founder whose company was going under. He needed more money, a better product, and a working business model. The founder had also hired several employees who had become demotivated and had lost faith in the business. Many of these employees had left promising jobs to join his company, and he couldn’t let them go.

The founder lost a lot of sleep agonizing over his decision before laying off almost the entire team. He ultimately realized it was better to send his employees to thriving companies than remain on life support at his company.

Years later, the company is now thriving and employs hundreds of employees. I recently told this founder I’m proud of his courage to face the demands of reality.

Is reality your friend? Or a distant acquaintance? Where do you have an opportunity to be more courageous?

One of the reasons I’m drawn to startups is the built-in sense of purpose. When every action you take impacts the life or death of your enterprise, you matter. And in my experience, that sense of responsibility brings out the best in people. I believe that humans were designed to flourish in their work and see again and again how people who were otherwise lost find themselves in their work. As it turns out, working in a fully-aligned team of talented people can be motivating and fun.

Working at a start-up, however, doesn’t always feel this way. Often, it feels more like wandering in the desert. You have a loose idea of the vision you want to accomplish but struggle to find a viable business model. Or maybe you’ve found a business model that is not working, and you only have six months of cash left in the bank. Tackling these existential questions is vital but also can be anxiety-inducing. Humans just aren’t wired for uncertainty.

It feels like drinking from a fire hose when things start to work. You suddenly have so much to do that you don’t have time to relax. You get to the end of the day and feel completely wiped. Then, you get up the next day and do it over again. Living this way can also be quite overwhelming, and clearly, this is not a great place to be in the long term. That said, whenever I end up here, I tell myself: “This is what a blessing feels like.”

A business exists to serve. When you are overwhelmed by customer appetite, there’s a good chance that your customers want what you’re serving. That means your business is inching away from death and into life. It’s the difference between going to bed exhausted and not being able to sleep at night. Let’s name it for what it is: a blessing.

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Here’s my walking desk stack:

• I got the idea for the walking desk from Eat, Move, Sleep. Tom Rath does 8 miles a day on his walking desk. Part of his secret is that he writes a lot and can walk at 1.5mph for 10 miles a day. That’s a lot - I walk around 1-2 hours daily on my treadmill.

• If you walk slowly enough, I’ve found that your brain forgets you’re walking. This works even better for immersive tasks: writing, programming, or video games. You’ll get into the zone and find yourself later in a sweat with your Apple watch letting you know you’ve burned 300+ calories.

• It turns out that walking makes you 60% more creative, according to this Stanford Study. In practice, I've found that walking makes me more engaged in meetings and 1:1s, so I try to do it whenever I can.

• Here's the treadmill and desk that I use. You can get more expensive models, but I found both at Costco, and they work pretty well.

Let me know if you use or are interested in getting a walking desk!

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There is a lot of great literature about making good decisions.

I’ve found the inversion to be more helpful. To make better decisions, simply make fewer poor decisions.

One of the reasons I like thinking about it this way is that it’s hard to know when you’ve made a good decision. Many of the best decisions are contrarian and not obviously correct a priori.

There exist many patterns around good decision-making. However, I find it much easier to identify the anti-patterns associated with bad decision-making.

Here’s my list:

1. Fear

   
   This is the most common reason I’ve seen founders make bad decisions. We’re afraid of losing our companies. So we go out of our way to protect them and often take risks that we shouldn’t be taking. We risk everything trying to save something that never really could have been kept in the first place.
   
   I’ve encountered fear many times over my founder journey. Every time I acted upon that fear, it was the wrong decision. I’ve made and have seen others make the same fear-driven mistakes:

   • Over-conceding to save your most negative customers that were going to churn inevitably in the first place

   • Over-promising prospective customers features that aren’t in your roadmap on a schedule that isn’t possible

   • Over-committing to retain your high-performing jerks and hoping against reality that they’ll change for the better

   
   Fear begets fear. When you act on your fear, it becomes easier and easier to focus on the short term at the expense of the long term.
   

2. Control
   
   I like to think about control as institutionalized fear. When we’re afraid over a long period, it’s natural for us to start to develop control mechanisms to manage that fear. Some of these methods are beneficial to the company, and some of them are not.

   
   As a founder, you regularly face problems that seem impossible. There’s a strong incentive to manage the information around those problems rather than the problems themselves.
   
   I’ve seen this anti-pattern happen in companies that have yet to develop a repeatable sales motion and want to maintain a certain narrative. So they clamp down on sharing information.

   
   For example:

   • Only the sales team and executives know about the sales pipeline.

   • Only executives know about the financials.

   • Only the founders know details about fundraising.

   When no one knows what’s happening in the company, the results will show up in your performance. [1]
   

3. Lonely and Tired
   
   I have an acronym that I abide by — HALT. It stands for “Hungry, Angry, Lonely and Tired” and is an excellent, consistent indicator of when you should NOT be making any critical decisions.
   
   It’s relatively easy to know when you’re hungry or angry. But when you’re lonely or tired, it’s not always so obvious. In the worst case, we ignore these feelings much longer than we should until something bad happens.

   
   I know a founder who gave up on his company - because he was lonely and tired. He had been working on a meaningful mission and gaining the traction that others would dream of. But a few months after raising a large Series B, he returned the capital to investors and shut down his company.
   

   His reason: he was lonely and tired. He had burned out of operating the company, and as the sole Founder/CEO, there wasn’t anyone available to replace him. [2]
   
   It’s hard to ask for help, especially when we need it the most.

[1] This is also why I care so much about making Anomaly transparent, especially in the earliest stages when the team is small.

[2] This post is about making bad decisions, and stepping down from your own company in this situation isn’t a bad decision. I think the bad decision is not developing a capable successor who can keep the dream alive.

If you enjoyed reading this, I write an expository 1-2x per month:

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1. When you’re willing to look stupid, you take risks that you would otherwise be afraid of taking.

2. As a result of taking those risks, you get rapid feedback on your actions, which helps you to learn much faster than you otherwise would.

3. When you learn faster, you get smarter (and are paradoxically less likely to look stupid in the future!)

In short, when you’re willing to look stupid, you learn faster and get smarter.

If you’re reading this, you instinctively understand how this works and have seen others use this technique to great advantage. If you’re looking for salient examples, I will encourage you to look at how some brilliant people behave on Twitter. They will ask a seemingly stupid question or make a baseless assertion. As a result, they will get noisy feedback, which they will then use to alter their worldview. This pattern is prevalent, especially in circles I follow, primarily investors and other entrepreneurs.

What I would like to talk about is not whether this works. Instead, I want to discuss why many of us aren’t willing to look stupid even though we intellectually understand that doing so might be helpful to us. To me, the answer to that comes down to shame.

For humans, the desire to be accepted by others is core to our nature, and being rejected by others is painful for us. If you’re a high performer, you particularly feel this pain because you’ve developed a very vocal inner critic around everything you do.

I haven’t figured out if there’s a way to make that inner critic disappear. I made a mistake recently that felt so embarrassing I went and took myself on a walk and listened to feel-good music to cheer myself up. In the past, I once felt so crushed that I laid down on the floor staring at the ceiling for an hour. Others I know will give themselves a hug or take themselves out for ice cream. Mistakes do hurt (even if that hurt is inside your head).

I have, however, decided that what’s most important is to get back up again. As Proverbs 24:16 at the bottom of the In-and-Out Fries says:

For though the righteous fall seven times, they rise again, but the wicked stumble when calamity strikes.

I like that phrasing because it illustrates the difference between being willing to look stupid and compromising on your morals. I believe that the former is a life skill, but the latter is something else entirely. Taking a risk should never be used as an excuse to harm others.

I’ll leave you with my favorite quote from Teddy Roosevelt (and Brene Brown, apparently):

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

Not only that, but we rejoice in our sufferings, knowing that suffering produces endurance, and endurance produces character, and character produces hope, and hope does not put us to shame…. (Romans 5:3-5)

When I read that, it was around 1130am PST. I thought – wow that is a cool verse. I inked an “A-men!” on the margin next to it. What I didn’t know was that two hours later, Upstart stock would be down 56% due to an earnings report. As I write this, Upstart is now trading at around $30, down 90% from its high last year of $390.

If you’re reading this, it’s because you also lost something. I’m sure it was money, but it was probably something else too. Maybe it was the down payment for a house you’ve been planning to buy. Maybe a new car. Whatever it was, I’m sure it was real and that you are hurting a lot. I spent 6 years of my life building a company and have now seen most of the economics from that disappear. I’m one of the lucky ones. Some of you had options and not restricted stock.

What I also want to share with you is that you’ve also gained something. It may not feel like it right now. This is not an “everything in life happens for a reason” statement, although I do believe that. This is a “you are now a person of higher character” statement. I think this is important to mention, because unlike your money, your character cannot be taken away from you.

If you’ve experienced a great loss in your life (and I’m sure you have), you know what I’m talking about better than I can put into words. For the rest of your life, you’ll be able to speak from a place of greater humility and authenticity. You gained something – maybe not equal to what you lost but certainly valuable in a different sort of way. I hope that wherever you are in this remote-first world, you are experiencing at least some of this life after death.

As a final note, I also want to say something radical. Losing everything could be the best thing that ever happened to you. At least it was for me. When I left Dropbox to start Prodigy, I was in such financial distress that my roommate approached me and asked me if I’d be able to make rent and that otherwise, he’d be kicking me out of the apartment. Without that experience, I wouldn’t be here today writing to you.

My radical hope – is that something better will happen to you. I hope that someday, you too will be able to say that losing everything was the best thing that ever happened to you.

Well, a few months after moving to San Francisco I was walking home and on the way ran into a homeless guy who asked me for a dollar.
After forking over the money, I asked him - what are you going to spend it on?
“Cigarettes”.

He then asked me, if I wouldn’t mind - could I give him some more money so that he could buy himself some food?

“Actually I’d love to buy you some food. Mind if I join you? Maybe we can go and eat it together?

I hadn’t eaten dinner yet at this point, so I ended up sharing my meal with this homeless guy and his friend.

Here I was, sitting down at a dinner with two humans and thinking that it was all about me.

Finally, he interrupted me. He asks me, do I know how to surf?

We spent the next half hour talking about the places he used to go to as well as surfing techniques.

Here I was, looking at someone in need and thinking that I could help him. Instead, it was he who taught me something. Here was a man who literally had nothing more than the net worth of $7 that I had just given him. But he’s poking fun at me, making fun of how un-Californian I am, and offering me free surfing lessons to boot.

I left smiling. It wasn’t about me. It as about me giving him the opportunity to give me something. More than the small amount of money, I gave him the comfortable feeling of knowing that he had dignity, that he was a giver and that he mattered in the world.

Someone once told me that if you focus on yourself, you can never really be happy. There will always be something wrong with your life. There’s always that "next thing” to complete / achieve that will make you “set” for the rest of your life. Maybe it’s enough money to never have to work again. Maybe it’s the significant other you’ve been looking for. No matter what it is, I think that that thing will never satisfy you until you can find comfort in where you are today, right now, in your life.

Over the last few years I’ve been working in this company, I’ve had to revisit and consciously break down many of my misconceptions regarding time and readapt them to fit my life inside of a start-up.

My goal in this post is to discuss my mental model for thinking about time at a startup today. I hope that this post can serve as a useful reference to the early stage startup that is looking to get more out of their working day - to start time hacking.

Time hacking: the big picture approach

Much of the literature you can find on time management involves turning yourself into some sort of robot. If you follow what you read, you’ll find yourself rising early, working through your lunch hour, staying extra hours late in the office, and/or deactivating your Facebook account.

While these are all techniques that can work, they are in my opinion, not low-hanging fruit. By working yourself to the bone every day, you can achieve maybe, a proportional increase in productivity. But that increase in productivity comes at a very real cost - your life. Startup burnout is a very real problem, and it is in my opinion, a very easy way to forfeit your hard-earned efforts toward building a company.

So I do not intend to write about personal productivity. Instead, I want to talk about methods that can achieve superlinear return on organizational productivity. While you do not necessarily need to work every hour of the day to get good results for your company, you must absolutely be able to build systems that can get those results for you.

Are you still interested in time-saving tips and tricks? Stop reading - there are hundreds of articles and self-help books out there and this will not be one of them.

Think things through before you start

The Cardinal Rule of Wasting Time: The worst way to waste time is to do something exceptionally well that needn’t be done at all.

Often, spending extra time initially to properly value the importance of your objective can prevent costly mistakes before they happen. The startup founder’s corollary to this is that picking your problem (and market) well can easily save your future business thousands of hours in potentially wasted execution time.

The notion that you could waste your time doing useless work almost sounds too obvious to be worth talking about. Why would I even bother doing something at all if I didn’t think it was important?

Unfortunately, it can be surprisingly easy to make this mistake. In fact, in a community of doers (like a startup) it can be even easier, because there will often be no one above you to chew you out and reject your idea. In a culture where everyone is moving fast, it is much easier to run with an interesting idea than it is to stop and consider whether or not the idea should be a top priority.

I know this can happen, because when we first started our company, we made this mistake several times:

• We built features that were never ultimately used.

• We overengineered the features that were used.

• We continued broken sales and marketing patterns because we had no criteria for terminating efforts that weren’t working.

• We ignored potential opportunities because we had no criteria for identifying efforts that were working.

Most, if not all, of these mistakes could have been mitigated with proper planning and preparation. Engaging in a proper planning and preparation process forces you apply the 80/20 rule to everything that you do. It forces you to estimate deadlines and dry runs the idea through everyone at your company. If there is a problem with the airplane, you’d much rather know while it is still on the ground then after you’ve taken off and are in mid flight.

Today, before we start any project we all make sure to critically consider whether or not it is the most important thing that we should be doing. If so, we define a schedule and execution plan. If not, we forget about it.

Never be blocking on anything

One of the main advantages of a startup is your ability to run faster than those around you. This advantage is entirely destroyed when you have to slow down your pace because you are depending on other organizations to make progress. In the worst case, your company can lose momentum entirely because you are blocking on some external event.

Paul Graham discusses blocking in one of his essays. He says:

“The best way for a startup to engage with slow-moving organizations is to fork off separate processes to deal with them. It's when they're on the critical path that they kill you—when you depend on closing a deal to move forward. It's worth taking extreme measures to avoid that.”

The way that I think about it is that it’s okay to be waiting for things to happen. It’s not okay if you are depending on those things to get anything done. When you order a package online, the fact that it takes several days to ship ranges from insignificant to incredibly important - based on how badly you need the package contents.

A/B testing and dynamic personalization are good examples of background processes. You make some tweaks to your website, and then switch contexts to do something else, while your tests gather data and compute statistical significance. After you’ve finished running your tests and analyzed the results, you make some more tweaks and then return the process into the background again.

Almost all of the YCombinator startups you’ll find begin by working primarily with smaller companies, and I believe that blocking has something to do with it. When you interface with smaller companies, you can increase your organizational clock speed tremendously and create a much tighter feedback loop (one of the key patterns to learning quickly). Because you are not depending on any one customer or lengthy sales cycle, you can very easily unblock yourself by focusing on other customers. Don’t lose momentum.

Create time assets, delete time liabilities

One common misconception about time is the belief that it can only be wasted, and never gained. People naturally assume that there are only 24 hours in a day and that you either use them or you lose them. Time, as the saying goes, is a finite asset.

This is, however, a faulty assumption because time can be stored. If you cook a week’s worth of food during the weekend, you can reap the benefits of this labor by eating that food throughout the rest of the week. Of course, software takes the notion of storing future time and exaggerates it tremendously.

Patrick Mckenzie writes a very good post about this where he differentiates between using time as an asset (investing your time in activities that will save you future time) and time as a liability (committing yourself to having to spend future time). I recommend that you check out his original article - I won’t rehash his work here. However, I would like to revisit the idea of time as an asset vs. liability from a different perspective.

When you first start your company, everything is a time liability.

Startups are formed, generally, without any processes and systems. Everything is, by its very nature, massively inefficient.

As a founder or employee on behalf of a product business, it is your job to create systems and processes to improve the way in which things are done. This includes product development systems (writing excellent documentation and unit tests) as well as marketing systems (content marketing, scalable SEM) that eventually become your time assets. Done properly, these systems will work for you for free, 24/7, and forever.

The key strategy here then, is to create your business in such a way that it can grow superlinearly, based on the cummulative time assets that you’ve created (and not linearly, based your personal time).

By the way, running a high-touch businesses can work, and there are many amazing businesses that involve significant time liabilities but are still stupendously successful. However, the idea that businesses need to have time liabilities should no longer be taken for granted. We are very quickly approaching an age where even B2B businesses can reach epic proportions without hiring a single salesperson.

Buy time whenever possible

In a business, time is almost always more valuable than money. Therefore, if you can solve a problem with money, it is much better than trying to solve the problem yourself with time.

What if I can write the code myself - why should I pay for it?

Contrary to popular belief, when you write code you are not done with it. In fact, every line of code that you write is something of a future time liability, because you might have to maintain it in unpredictable ways for its useful life.

When we first started Predictive Edge, we didn’t understand the fact any code we wrote would create an inevitable future time liability. So we made a lot of decisions to create software in-house to “save money” at a very small cost of time. We self-hosted our version control, implemented our own error notification system, and hosted our own configuration management.

The end result of all of this work was that we saved, maybe, a few hundred dollars a month. But I guarantee you that I spent more than a few hours a month combing the internet for solutions to intermittent configuration bugs. I ultimately ended up going back and buying most of the software that I had tried to program myself out of needing before and haven’t looked back since.

This gets me to another point. Software is cheap. Seriously. I find it astounding that the same person who wouldn’t think twice about spending $10 on their lunch thinks that it is ridiculous to spend that same $10 on a business application that will save themselves time and energy every day.

Today, if there is a tool out there that I am sure will save us any amount of time, I buy it immediately. I have not encountered even a single case where I have had to justify the ROI. The value vs. price bargain that you get software is even more enormous when you consider how expensive engineering talent is these days. Instead of hiring additional team members, our company instead buys useful tools that act like “virtual team members”, without having to draw salary or a health and benefits package.

Although we have not done it at our company, I have seen a lot of entrepreneurs apply the “prefer to buy” principle towards outsourcing effectively.

Be process, not outcome oriented

Whenever possible, I prefer to think it terms of processes rather than in terms of outcomes:

1. A process is something that repeats.

2. An outcome never repeats.

Because processes repeat, you can improve them. You can complete them in less time and (through documentation and/or analytics) develop methods for making them yield better outcomes. When something happens over and over again, any incremental improvement is multiplied by each consecutive execution. This can equate to big long-term wins for your organization.

Conversely, the fact that outcomes never repeat makes it very difficult to improve them. When a deal falls through due to a “one-time” mishap (as most deals seem to do), it is pretty hard to learn from, unless you were paying careful attention to your process for closing the deal. Successful deals can be even worse for learning because unless you were paying attention (1) you really have no idea exactly why they succeeded and (2) you really have no idea how to make the success repeatable.

Process-building is time-consuming, deliberate, and not nearly as sexy as landing a string of bad-ass business deals. But I’d much rather plan to be methodical than plan to be lucky.

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When my brother matriculated at MIT, he had already taken honors multivariable calculus at Stanford (receiving an A). However, MIT refused to accept the Stanford course as credit for it’s own (non-honors) multi-variable calculus course [1]. Instead, he would have to take a placement exam along with all of the other freshmen hoping to place out of multi-variable calculus. No problem, I figured. As I saw it, his preparation should have been more than enough.

Well, here’s my paraphrase of my brother’s story:

Ten minutes before his multivariable calculus exam, I walked to the exam room and noticed a girl sitting outside immersed in her crib sheet. She had meticulously copied all of the formulas that she had learned down on it and was last-minute cramming before the exam. I asked her if I could take a look at her preparation sheet. Upon examining her preparation sheet, I quickly realized that I did not know a single formula on it. Many of the formulas were for double integrals.

Minutes before the exam, I did not actually know how to actually take a double integral.

In the quarter I had spent doing honors multi-variable calculus at Stanford, I had done literally nothing but proofs. While the class had been exceedingly difficult and had required us to prove many non-trivial properties about double integrals, we had never actually taken one. The professor deemed this material as unsuitable for the theoretician to waste his working memory on. He consciously never taught it.

In the next five minutes preceding the exam, my friend Nathan (who had also taken 51H at Stanford) and I learned how to take a double integral. Following that, we both prayed to the god of partial credit and headed into the exam room.

The actual exam contained quite a few double integrals that I was unable to solve. So what I did instead was exactly what I had learned to do in 51H: I proved the theorem that they wanted us to apply. Then (as I’d never learned any of the formulas) I’d just leave the problem there: with a proof in English and no numeric answer.

Given that he never wrote an answer for a good part of the test, you might expect that my brother bombed his exam and had to retake the class. However, he instead passed his math exam with flying colors, receiving one of the highest scores out of his placement group.

In my brother’s case, his high-level theoretical understanding helped him to quickly comprehend the low-level applications that he had to solve [2]. There would simply have been no point for him to spend extra time learning how to plug-and-chug numbers into what already knew. Furthermore, I assert that the teaching philosophy of his Math professor is spot on. I’ve believed for a long time that (if you can do it), it’s always better to skip the basics and go headfirst into the advanced stuff. If something is beneath you, don’t learn it. If it isn’t worth your time, then don’t spend your time on it. My philosophy is that you should learn how to tackle the hardest problems that you can. And the contrapositive to that is that you should triage everything else, as much as you can.

I used to live with an entrepreneur who literally never cleaned his room or cooked his own food. What he did do was use TaskRabbit to hire a helper, who kept his room immaculate and would cook him plain chicken and brown rice. Now I’m not a chef, but chicken and brown rice is not the toughest meal to make. I’m sure he does this because he realizes that there is no point in wasting his time doing tedious life maintenance when it would be better spent making business deals, meeting new contacts, or spending time with his girlfriend. And although he is still young, his track record for focusing on these aspects is already quite good. Already, his decision to skip the basics has helped to make him one of the most seriously professional and well-networked people who I know.

Modern education has an obsession with fundamentals. We persist in preaching a canon of knowledge that includes that is almost entirely basic. The general consensus seems to be that a student should first learn the basics, slowly increasing difficulty with higher levels until those too become basic. While this may be true in sports (Lebron James still practices his dribble), it doesn’t seem likely to me to be true for most of knowledge [3].

[1] This would have been reasonable to me, had my brother taken the normal multi-variable course as opposed to the honors one. Objectively speaking, I do think that MIT is a more theoretically rigorous school than Stanford. There is a reason why many more Math and Science Olympiad kids go to MIT, and I think this is in part because the undergraduate education is more intellectually invigorating. The students are more nerdy, and the classes are harder (of course, people go to Stanford for other reasons).

[2] I am often skeptical about much of what I hear. However, my own experience with Math leads me to believe that this is not actually as difficult as it sounds. Math is much more so a system of logic than it is a system of numbers. In fact, real mathematicians never use numbers.

[3] The former understanding of knowledge is something like a line. You progress a little and move a bit forward on the line. We like thinking about it this way because one-dimension is easy for us to intuitively understand. However, we already know that our brain - composed of highly-dimensional neural networks - does not fit this pattern at all. If we tried to understand knowledge this way, it’d be something more like evolution: highly punctuated and irregular, with random connections from all over the place, full of equally surprising successes and failures. In this case, everyone’s learning pattern would be different, as it should be.

I remember that when I was applying to college all of the essays that I could find online were utter crap. So I went and dug up my own college application essay (circa 2007) to open-source it with the community.

I wasn’t one of those cool kids that hacked out their college application in 24 hours. I believe in working hard for the things I want in life, and the essay I’ve included below is the product of many months of work.

I hope you enjoy it.

Marty

11a: “A picture is worth a thousand words,” as the adage goes. (You’re limited to one page, however.) Sometimes a photo or picture can capture an object that you treasure, a person you admire or a place that you love; sometimes a photograph is simply your record of an experience or moment in your life. Imagine one photo or picture that you have, or would like to have, and tell us why it is meaningful to you.

A picture that is meaningful to me is that of a man riding his bicycle at the crack of dawn in China. He is sixty years old and carries a massive, overflowing pack on a bicycle that must have been built in the 50 s. As he struggles through thick traffic and acrid smog, he appears to be a beast of burden. I watch his raw sinews strain under the sheer weight of his load. As the bike squeaks, I can imagine both groans of anguish and a silent plea unnoticed by the numerous bystanders. He squints as he pedals into the rising sun, leaving behind a long shadow and an image that I will always remember.

This picture made an impression on me because I too am a cyclist. My humble bicycle is also a two-wheeled vehicle in a world of four-wheeled machines. Even though my bicycle is not as old as the one I saw in China, it is still the oldest at Palo Alto High School. The bicycle s rusting steel frame is scratched and the tape on the handlebars has long since peeled off. Every day it bears the weight of a rider, a textbook-laden backpack, and a trip up Page Mill Road. The bike is silent, but I huff enough for the two of us.

I choose to bike knowing that a car could effortlessly cover the ten miles that I travel each day. Every night after work, I arrive home sweating, exhausted, and with aching quadriceps. I do so because I enjoy the challenge of the strenuous exercise and the simple rewards of a refreshing breeze, a relaxation of mind, and the cleansing effects of an occasional rainy day. I feel proud that every mile I travel is a step toward reducing emissions, and at the top of each hill I feel the satisfaction of freedom and healthy activity.

My encounter with the old man brought my experiences into perspective. Even though the bicycles we ride are similar, we regard biking very differently. Clearly, he would never associate biking with pleasure. Unlike me, he is not pedaling by choice. He is probably not concerned with either the environment or exercise. He pedals simply to survive. If I were in his saddle, I would surely pray for divine intervention in the form of a car.

This moment made me realize how privileged my background is. But more importantly, it made me realize how much our backgrounds shape our perceptions. My view of the bicycle has been shaped largely by my upbringing in America. We associate biking with the heroic champion of cancer research, Lance Armstrong. In a country experiencing increasing concern about gas prices and global warming, we see biking as a responsible alternative to driving. However, the same bicycle that represents a means for combating global warming in America is associated with physical labor in China. In America, people will often sport custom outfits and bike for leisure, while in China people ride bicycles because they have no alternatives. It is astonishing that two people can view a common object, such as a bicycle, in completely different contexts.

I cannot help but wonder: If even our perception of a common bicycle can differ so dramatically, then how differently must we perceive more complex issues? This gives me a greater appreciation of the difficulties that must be overcome in getting people to come together to solve larger problems such as pollution, poverty, energy, and peace. I think we can never get underneath someone else s skin and think like that person. But I do believe that if we broaden our backgrounds, we can come much closer. As I deal with others, I will always keep in mind Anais Nin’s observation, We don’t see things as they are, we see them as we are.

Ordinarily, when I think about a Math Phd student, I envision someone who’s known that they’ve wanted to do Math essentially their entire life. I think of a person homeschooled, who’s skipped on three grades in math, and won multiple math contests in the region. My friend would not have fallen into this category.

However despite lacking an intense Math background my friend had and still has a formidable work ethic. When she was in high school, she went to the library after school every single day, and would stay there working until it closed. On weekends when I’d occasionally go to get leisure reading from the library, I’d see her there working. After she went off the University of Pennslyvania, I was in the dark with her for about three years because she disabled all of her social media (e.g facebook). Given all of this, I’m not at all surprised that she excels as much as she does in Chemistry and Math. When you have a work ethic like that, double majoring into a Phd is really no big deal.

Mathematics resonates strongly with me because that was what I did and was good at in my academic life through high school. However, my story is a bit different from my friend’s. Unlike my friend (who immigrated from Korea) I was a prototypical Bay Area Math kid. I practiced supplemental material at home, skipped a grade in math and was an active member of the Math Contest Club through both middle and high school. I did reasonably well in math competitions.

Despite this, I never believed I was very good at Math. Part of this was because I spent my entire math career being overshadowed by my peer mathletes [2]. How could I ever hope to pursue a future in math, when I wasn’t even close to a top mathlete in even my friend group? [3]

I gave up on math. Once I got to college, I stopped taking math classes entirely. I even went so far as to petition the Computer Science department to waive my Math requirement (due to the classes at Stanford I had taken while I was still in high school). To this day, my math ability is essentially where it was when I was in high school.

What I learned the hard way is something that I should have learned in Algebra class. Back then, the equation to know was slope y-intercept form, y=mx+b. We had perhaps an entire unit of doing nothing but understanding and graphing this equation. For all of the time I spent doing this, I never realized what this equation really meant.

The simple fact about life is that a little bit of extra slope can make up for a hell of a lot of y-intercept.

[1] I come from the Bay Area and there is a very strong emphasis in Math here. For example, my high school has several tracks for Math, problem-solving classes, and a very active Math Contest Club (a club in which I am proud to have been a part of).

In my friend’s case, I remember that the furthest math level that she reached in high school AB Calculus. She neither participated in math contests and did not do math outside of her school work. While I know that she did exceptionally well in her classes, it is with my Bay Area bias that I say she was undistinguished (at the time) in Math.

[2] I remember that while I was a student at Paly we had two kids make it to the MOSP International Olympiad preparatory camp in a single year. Consider that MOSP is for the top 40 mathematicians in all of the United States (It’s a boot camp for the International Math Olympiad). I knew the both of them personally and they are exceptionally well rounded individuals. In fact, one of them is one of my best friends.

(I often tell myself that I’m spoiled because I’ve been able to spend my entire life in the company of such highly intelligent individuals).

[3] It turns out that my close friend group was exceptionally intense - something I had no perspective at all about at the time. Even my close friends who don’t do math are intense about what they do. For example, I have a friend in high school who used to be All-American for swimming (which means he was one of the top 50 swimmers in the world). He once casually told me:

If I’m going to do it, I might as well try to best in the world at it.“

It makes me think of Nike. Imagine if Nike’s motto were changed from "Just do it” to “Just be best in the world at it”.

I told him that while I didn’t know much about the company, my gut response would be not to sign with them. I said this because to me, the CEO’s behavior reflects a flaw in his personal integrity. In my opinion, any employer unscrupulous enough to pressure a candidate to accept a job offer is going to be less likely to have qualms over:

• Forcing that individual into a ridiculous working schedule

• Missing payroll (this does happen)

• Lying about the company’s progress

I come from perhaps an old-fashioned school of thought because I believe that being an employer is not about owning another person. In my opinion, a candidate has the right to work for whoever he/she wants, and should be free to pick the best option available to them [2]. (In this view, it’s almost more as if the candidate owns the employer). If as an employer, I am unable to give a candidate a highly competitive offer and growth opportunity, then why the hell am I hiring in the first place?

This CEO’s behavior bothers me because I personally want to help every candidate make the best decision for him/herself regardless of whether or not they decide to join our company. For example, one of the candidates we’ve extended an offer to intends on making her final decision about where to work as late as September. Not an issue here. Another very strong candidate of ours ultimately decided to work at a bigger company, and I encouraged him to do so because I believe that given his circumstances it was the correct play for him.

One of the reasons I started this company was that I wanted to create an environment in which people who can do good work would find worthy of joining [3]. In my mind, you have entirely no hope of doing that without integrity. That’s how much of a mistake I feel that the aforementioned CEO is making.

[1] To put things in perspective, he really is a qualified candidate and will be able to get other offers if not for this one. I don’t suspect that my advice would be too different though, even if this were likely to be his only offer.

[2] I will say that as much as I think that it’s important for an employer to have personal integrity, a candidate should also be held accountable for his/her actions. For example, I would not think much of a candidate who lies or vastly over-exaggerates their resume (it’s really not as hard as you might think to find out these things).

[3] Yes, I know that I’m being overly-idealistic about this - as I am about a lot of things in life - but I have to say it anyway because I believe it. I think that perhaps a flaw of Stanford entrepreneurs is that they get overly passionate about changing the world when the world really doesn’t want to change, and that is definitely a flaw of mine.

[no real footnote] My personal opinion is that in business (and really for life in general), you’re expected to regularly interact with people whom you may not personally like. That said, I would still make a deal with someone whom I did not personally like. However, I would be hard pressed to make a deal with a partner whom I considered to have low integrity. Imagine buying a product from a vendor with no integrity: what’s to stop them from just taking your money without delivering the product?

Programming at a startup is, in general, much easier than the work you’ve already done in school.

I’m assuming a lot of things when I say this. Naturally, I’m assuming that you challenged yourself while you were in school. You took some of the hard classes and didn’t just coast through the easy ones [1]. You completed all of your assignments (likely taking multiple late days, but hey, finishing is finishing).

In school you work on problems that get progressively harder. By the time you reach the upper division classes, you are working out non-trivial proofs about algorithms that took you multiple lectures to understand. Even if you’re not in a theory track, you’ll be expected to grok papers about the newest research in the field. Not to mention, (since you’re a CS major) you’re probably taking 3-4 of these classes at the same time. [2]

In my opinion, this kind of pencil pushing is way harder than coding! It is very difficult to implement, say, a non-trivial variation on a maximal matching algorithm for bipartite graphs from your brain, with nothing but pencil and paper, on an exam. You don’t even know if you can do the problem or not, let alone write anything down on the paper! If you fudge a “clever hack”, that’s zero credit. Because it’s not clever, it’s just plain wrong.

The real world is not quite so unforgiving. For one, you will almost never a problem in software that you can do nothing about. If you’re stumped on a tough architecture decision, just look up standard practice on Wikipedia. Phone a friend. Take a walk around the neighborhood and then decide that it’s not really a problem that you have to do anything about. It’s software so there has to be a way to get it done.

Unlike the code you write in school, everything you write in production has TONS of bugs in it.

When I was in college, we had unit tests given to us for everything we wrote. For CS140 - Operating Systems (by the way, this was perhaps my favorite class at Stanford, every CS major should take it), our team would have been absolutely destroyed if those unit tests did not exist. But because they did, we had a notion of progress. We’d make the tests pass, turn the project in, and call it a night (or early morning). I’d generally know if I did a good job on the programming or not before I had turned in my assignment. Once I’d turned it in, I’d never have to look at it again.

My analogy for unit tests is that they’re like monkey cages. Programmers (myself included) are the monkeys. If left to their own devices, they’ll chaotically bang on their keyboards, and create a total mess for themselves and all of the other monkeys. Sooner or later it’ll be Planet of the Apes. The cages provide structure and prevent the monkeys from making a total mess of things.

In the code I write now, I assume that nothing works unless I’ve tested it and it works. Even then, it still probably doesn’t work, because I probably wrote the test incorrectly. If I find what looks like a JVM error - hold your horses, it’s not a JVM error, you screwed up - I’ll assume that there’s something wrong in my own code. If I didn’t think like this I would probably not find any bugs.

You spend almost as much time getting the requirements correct as you spend building the damn thing.

One of my favorite classes (other than Operating Systems) that I took at Stanford was CS155 - Computer and Network Security taught by John Mitchell and Dan Boneh. When I took it, the class had the Operating Systems class (CS140) was a prerequisite. Since I was just a sophomore at the time, I hadn’t taken Operating Systems, but after sitting in the first lecture found the class so interesting that I signed up for it anyway. [3]

I strongly remember the second project, because that project just about killed me and my partner. In the project, we were asked to implement traceroute, in C. Implementing traceroute itself is challenging enough for a class of students who haven’t taken networking. But we were additionally asked to implement highly non-trivial variants of traceroute. These included firewalking traceroute (if you don’t know what that is don’t worry, it burns just about as hard as it sounds) and ghost traceroute (this was actually illegal, so we were only allowed to test in a small lab provided to us on campus).

If this weren’t hard enough, the documentation left basically the entire assignment ambiguous. To figure out basic information, such as which ICMP headers to send under which circumstances, you’d have to pore through the newsgroup, which contained tons of other confused students and very few actual answers. By the time we had finished the assignment, the newsgroup had something like 3000 posts in it.

My partner (another sophomore) and I read them all. We finished the assignment. Actually, I think we were one of the only teams to finish the assignment because the average score on that assignment was 24/100. By the way, I want to tell you that I attribute our score on that project completely to my partner, who is the best networking engineer that I know. Some people are just that good.

The funny thing about that assignment was that it was actually more spec’d out that anything I have ever written since graduating. Traceroute has an RFC. Also, once the description of the problem had been cemented, we knew exactly what to write. We never had to delete all of our code because the specification changed. No one ever said: “Wait, are you really building traceroute? wtf, actually what I want is a program that draws a bunch of unicorns on the screen!”

[1] You can actually do this now, and it infuriates me! From my point of view as an employer I don’t even know if someone really even knows CS, based on the fact that they have a CS degree alone. I’ll save the rant for some other day, though.

[2] There’s one CS major that know who took 7 classes at the same time. I lived in the same dorm with him and never saw him eat a meal outside of his room (however, he did shower - the whole thing about CS majors never showering is just total BS). Some people are just that good. I mean, it’s Stanford, who am I kidding?

[3] The CS program at Stanford doesn’t really enforce prerequisites, so you can take whatever you want if you can handle it. When I was an undergrad, I tended to do this a lot when I was first getting into CS. However, I would definitely not recommend it even if you think that you can. The gist of my point is that taking classes early is hard because you won’t (in general, myself excepted) have good partners. Also, it means that you’ll have to take the lame easy classes later, because they’re required anyway. Trust my co-founder, you don’t want to be learning about induction in CS103 (Mathematical Foundations of Computing) when you’ve already done it in CS161 (Design and Analysis of Algorithms).

To be contrarian, I prefer to distill my work balance into a few rules that are easy enough for my brain to wrap around. This is what I do:

1. If I’m awake, I should be working.

2. If I can’t focus enough to do my work well, I should take a break.

3. If I’m too tired to work after taking a break, I should be sleeping.

I once asked one of my most diligent friends in college how he was able to take all of the hardest CS classes, work a part-time job, and do academic research in his spare time.

me: “How do you manage your work/life balance?”

friend: “Well, that’s an easy one. Let’s postulate that I have no life. Then really, there’s nothing to balance, is there?”