I’m fascinated by Nassim Taleb’s concept of “antifragility,” that the opposite of “fragile,” something that breaks easily under stress, isn’t something that is strong; rather, it is something that heals and learns quickly in response to stress.

Ever since I learned about this concept, the more I see it in everyday life and the more I believe that it is a fundamental part of success and happiness.

Antifragile Entrepreneurship

For example, in entrepreneurship, this is the idea behind the trial-by-fire, learn-by-doing approach of entrepreneurship. The prototypical entrepreneur is highly risk-seeking to the point of irrationality. A simple cost-benefit analysis would dissuade most people from traveling down this path; yet, the entrepreneur is an entrepreneur because of the risk involved.

The entrepreneur runs through walls they don’t know exist. The same unknown unknowns that can doom the entrepreneur to failure are the same unknown unknowns that create the outsized successes of the entrepreneur.

When you look at the decision tree from that perspective, it seems not so bad: failure is always the same, a zero, while the return (however you define it: monetary, happiness, utility, etc.) is astronomical, and worth it.

“The Entitlement Generation” is Fragile

My generation is an obnoxious one. The author Ron Alsop calls us the Entitlement Generation. We are a generation of Millennials, trophy kids of doting parents who went through immense sacrifice to ensure our success, praising our accomplishments and padding our failures to avoid hurting our self-esteem. The losing team of a soccer game gets ice cream, too. They get an E for Effort.

I’ve met people in my generation who are surprised when they don’t have things laid out in front of them. And they perpetuate the problem because they expect something to be done for them. Many times they’ll wait for a long time for something that won’t come. It is this idea of entitlement that prohibits them from being antifragile. Rather than learn from the roadblock, they stagnate. “Many flounder without precise guidelines but thrive in structured situations that provide clearly defined rules and the order that they crave…” Because everything was given to them, “those basics aren’t necessarily apparent to many millennials.”

I think entrepreneurship is the greatest equalizer. Everyone is treated the same. If you don’t perform, you don’t succeed. You alone are responsible for your success.

You don’t have to come from a rich family to be subject to antifragility of entitlement. I come from a middle class family. My dad is an environmental engineer who designs landfills and makes sure that the runoff from the landfill when it rains doesn’t get into our drinking water. My mom stays at home to take care of now 6 (six!) kids, the equivalent of 6 most important jobs in the world. Arguably more important than anything that I’ll do in my lifetime.

Dad immigrated alone to the USA from Taiwan, leaving his wife and 2 kids, ages 1 and 3, to pursue his dream of getting a masters in engineering from a top school, and ultimately of building a solid foundation for his family and his children to stand on the shoulders of giants.

So they did (and still do) everything in their power to make sure that my siblings and I are in the best position to succeed. It is the greatest luxury of all to not have to worry where your next meal is coming from, whether your life is going to be in mortal danger from exogenous forces. We can concentrate all of our efforts towards our own self-gain. This is the greatest gift that my parents gave me.

And it takes all of my power of self-awareness to remember that. I will not squander this opportunity. It takes all of my power to remember that I am not entitled to anything. While my parents did everything in their power to make sure that everything was lined up for me and that I got a good education and went to a good college, they made sure to instill values in me of appreciation. This is the intangible that cannot be recorded in grades that I will forever be grateful for.

Expect nothing. Earn everything.

Happiness and Shocks

The eternal cliche of all cliches is to enjoy the journey, not the destination. But I believe that cliches are cliches because they are true. And the biggest cliches are the most difficult to internalize. I believe this King of Cliches is core to antifragile happiness.

There are two main types of mindsets that separate the fragile and antifragile. Stanford psychology professor Carol Dweck categorizes them as “fixed” and “growth,” respectively.¹

Those with a fixed mindset believe that abilities are innate, a given, whereas those with a growth mindset believe that abilities are learned.

When those with a fixed mindset are faced with a system shock, they stand in place. They are too focused on the end result, and shocks to the system seem daunting and maybe even annoying. “Why can’t we just get along with the show?” They constantly look for the shortcut to success because that’s what they’re used to; they believe that success and happiness is innate. They look upon the goal with longing, but aren’t willing to put in the effort to get there:

“If only I were rich.”

“If only I knew how to code.”

“If only I had the perfect girlfriend.”

On the other hand, those with a growth mindset embrace the inevitability of these shocks. Rather than try to account for every possible outcome, they embrace the immutability of unknown unknowns. For example, the most successful people I know are skeptical in shockingly great outcomes and optimistic in shockingly bad ones. And when a shock occurs, they know that they alone are responsible for their own change and their own happiness.

This is the core idea behind antifragility, shocks, and happiness. These shocks are inevitable, and they don’t matter as much as you think. They’re just part of the process.

I believe a key trait of a good entrepreneur or investor is the ability to make quick decisions in the face of unknown uncertainty, acting with decisiveness and conviction, trusting your gut.

So, then, developing your gut is the work you can invest in beforehand, and experience is the thing that trains and calibrates your gut to be better.

If you don’t have much experience, you need to hack it by creating as much action as possible. If you double the actions you take in a year, you double your experience. If you’re afraid, fake it till you make it. Doing things decisively is the only way to learn, get feedback and data, and calibrate your gut.

Decisiveness also works the other way. When something goes wrong, a good entrepreneur stops the problem from traveling too far downstream and compounding on itself. For example, this is the idea behind “hire fast, fire fast.”

I believe the most successful entrepreneurs are those who are both decisive and nimble within the context of a overarching goal. They ghetto test their hypotheses and gather as much data as possible so that they know that they’re heading in the right direction before allocating a ton of time and resources. They are decisive and nimble, proactive rather than reactive.

In my experience as both an operator and an investor, I’ve found that there are 5 common rules of thumb to land your dream startup job.

This isn’t a step-by-step guide to finding a startup job because you will find from talking to people that there is no standard path to get a startup job. However, these rules of thumb are a strategic framework that you can use to determine the tactics by which you can find your dream job.

1. The Best Jobs Aren’t Posted

In my entire career, I’ve never had a job that I got through a job posting. This is probably an extreme case, but my main point is that you should be thinking about what you would want in an ideal situation first, rather than be confined by what jobs are posted. In many cases, jobs are filled without any posting because many entrepreneurs tend to hire opportunistically. What would you do if you weren’t afraid?

In my experience, job descriptions are general guidelines to narrow the flood of applicants they get. Go above and beyond the job description to demonstrate your vision of what you can do for the company.

2. Quality, not Quantity

Pick 5 startups. Only 5. If you’re not passionate about the startup you’re talking to, it will be very obvious. Don’t be “that guy” who desperately wants to “work in startups” but has no passion for the people who run the startups you want to work for, or what the specific startup does. Do your homework.

Share the same vision and passion for the startup you want to work for. The onus is on you to show that you and the startup “coincidentally” have the same vision for the future. If you spread yourself too thin, you won’t be able to authentically achieve this.

3. Verify Your Authenticity

There are two ways to do this: externally and internally. External authenticity is how other people vouch for you. Internal authenticity is what you can do yourself to demonstrate your skills to your potential employer.

Examples of external authenticity are: getting a warm introduction from someone they trust; and building your “personal brand” by building thought leadership around a blog and Twitter interactions. For example, I got an interview at RRE Ventures because I had gotten to know Jim Robinson IV over Twitter.

Internal authenticity is about being the thought leader in a space that the startup is lacking in. This brings us to the fourth point:

4. Do the Job You Want and the Job Will Come to You

Once you’ve identified what your dream job is, don’t wait for that job to appear. Start doing that job and prove that you can do it, not only to your future employer, but also to yourself. Once you focus on just doing, you’ll find that opportunities will come to you.

This advice is applicable regardless of skill set.

• If you are an engineer, hack on your favorite startup’s API, regardless of whether they host a hackathon.

• If you’re in business development, reach out to your corporate strategic connections and pitch your favorite startup. As my friend Steve Schlafman said, “come bearing gifts.”

• If you’re a designer, do an unsolicited redesign of your favorite startup’s iPhone app UX. Be thoughtful about your thought process for the redesign.

5. People are Afraid of Micromanagement

One of the biggest fears of a startup CEO is that their new hire creates more work and micromanagement than they are supposed to solve. Everyone knows and expects that there will be some time needed to onboard and train a new employee, but because startups have such few employees, the marginal effect (both positive AND negative) of an employee is amplified. If you are 1 of only 7 employees in an early stage startup, everything you do has a strong effect on the startup’s trajectory. Contrast this with a big company, where, if a single employee slacks, the marginal effect on the momentum of that company is less easily noticed.

This point is related to the previous point. If you can demonstrate to your desired employer that you are not only capable of doing the job, but also that you are already doing the job that you are being hired for, they will feel much less anxiety because they have de-risked that aspect of potential micromanagement.

The act of hiring you should be a formality. You should make it obvious to a startup that, in order to achieve their vision, they need to hire you.

A common theme in running a startup or building a product is optimal time allocation. Since time is the only truly immutable resource, the most precious and scarce resources are your:

1. development (engineering/design) cycles
2. sales/biz dev cycles
3. marketing (user/customer acquisition/retention/virality) cycles

Each of these cycles are iterative processes with inputs and outputs, and the outputs tell you whether you’re on the right track — whether you should commit more time and resources to the effort.

The most risky cycles are those with binary outcomes because they are “all-or-nothing” results. They can screw you over because they can zero out after a large time investment on your part. Your goal is to derisk these binary outcomes as much as possible to avoid wasted time allocated. Don’t build past what you need to build to answer your questions. Kevin Systrom and Mike Krieger call this the Sink or Swim School of Engineering.

The way you prevent this is by subdividing the big binary outcome into smaller outcomes to make sure you’re directionally correct. Use iteration to prove out your hypotheses.

Examples of Binary Outcomes

How many times have you heard or told yourself something like the following?

• Development: “We just need to launch our iPhone app and we’ll achieve instant viral growth.”
• Sales: “We just need to sign Nike and we’ll be golden.”
• Marketing: “We just need 100,000 users before we can launch.”

These are all hypotheses with uncertain results. The reason you commit cycles to them is to try to prove or disprove these hypotheses.

The problem with all of these hypotheses is that they are binary outcomes — they are all-or-nothing. In many cases, they are Catch-22’s. They 1) are vaguely defined, and 2) have long cycle times before you get any information back confirming or disproving the hypothesis.

Here’s a way to visually understand this:

Let’s take for example the development cycle binary outcome: “We just need to launch our iPhone app and we’ll get viral growth. There is a huge market need for this app.” The two possible outcomes here are:

1. True. Expected Value: There will be viral growth when we launch our iPhone app.
2. False. Expected Value: There is little to no traction.

Each of the two outcomes have a probability and expected value. The first outcome, “True,” is the confirmation you’d like to see, and the second outcome, “False,” has an expected value of 0.

Cycle Time: 3 months: Let’s say that you want to “stay in stealth mode” and not get any feedback except from your closest friends until you launch. It will take 3 months to develop the product and launch it.

The main problem here is that it’s a binary outcome. If after the 3 months, you realize that there is little to no traction for the iPhone app, you will have wasted 3 months of dev cycles building something for which there is a low probability of success.

It would be optimal to realize that there is no light at the end of the tunnel before allocating 3 months worth of dev cycles to an outcome with an probable expected value of 0.

Solution: Interim Proof Points

The solution is to introduce interim proof points with short cycle times so that you get the information faster. Break down the binary decision tree into smaller interim proofpoints that can give you conviction that you should be allocating dev cycles.

In this example, let’s say that you introduce 3 week dev cycles to make sure you’re moving in the right direction.

Now the decision tree begins to look like this, subdivided:

Before you commit to a dev cycle, make sure it matters. Make sure you have conviction. When you get information in quicker time intervals, you get a better sense of whether you are allocating your cycles in the right way. You want to get quick feedback about whether it is worth your time to pursue it.

Examples of Interim Proof Points

1. User Acquisition: “A user will convert through the sign up funnel and download our app.”
2. User Retention: “A user will return at least once a week to use our app.”
3. Viral Loops Potential: “There will be a viral coefficient greater than 1.”

Now say for example that you find Interim Proof Point #2 to be incorrect:

You can make sure you don’t waste dev cycles trying to get to proof point #3 if it’s iterative and dependent on proof point #2 being true.

Splitting up the long binary cycles into shorter iteration cycles can help a lot to make sure you’re allocating your time optimally.

Here’s an example: foursquare. I don’t have any specific metrics around foursquare’s decision to shift their focus from check-ins to Explore. However, I imagine the decision was difficult for the foursquare team because their check-in metrics were still good, just not growing as fast as their Explore metrics. They made the decision to focus on the higher growth opportunity rather than stick with the safer option that might have resulted in an outside competitor snatching up the Explore opportunity from them.

Here’s another example: Zynga. Back when Myspace was still dominant and Facebook was still the emerging contender, developers committed most of their resources to building on the Myspace platform. Zynga did the same, but the difference was that they tested relentlessly, and discovered that Facebook provided massive virality opportunities. The Zynga team therefore decided to reallocate their cycles to building on Facebook.

This was a radical decision, since the Facebook opportunity was still small. However, much like the pattern in the Innovator’s Dilemma (Clay Christensen), Zynga jumped to a separate value curve with an exponential growth rate rather than stayed on the larger, but slow growth Myspace market. By the time others realized the potential of Facebook, Zynga had already entrenched themselves.

The key point here is that Zynga: 1) tested relentlessly, and 2) had extremely short dev cycles to be able to realize the disruptive opportunity in Facebook. If they had long dev cycles, it’s quite possible they would miss those early signs.

Shorten Your Iteration Cycles!

So the goal is to continue to create shorter and shorter iteration cycles to make decisions faster and more optimally. You should be getting feedback and confirmation you’re moving in the right direction on the order of days, or even hours.

Don’t Leave Your Fate Up To Randomness

To summarize, your goal is to make random binary outcomes deterministic rather than random. When you have a binary decision tree, it is hard to break down the specific ways that you can control your fate. Instead of having one big probability, you should break out a single binary decision tree into multiple branches.

Don’t get stuck wandering the forest. This framework helps you avoid the sunk cost problem. It’s not productive to work on the small things.

Subdivide the big binary outcome into smaller outcomes to make sure you’re directionally correct.

Thanks to Andrew Chen, Robert Goldberg, and Vish Makhijani for helping me crystallize my thoughts in this post.

One of the biggest challenges in building a product is prioritization.

When you have 1,000 things bombarding you and demanding your attention, it’s hard to figure out what is most important. You have your customers telling you one thing (vocal minority), your team and investors telling you another (selection bias), and your data telling you another (confirmation bias).

Everyone is an armchair critic.

The result is that I see a lot of products that do way too many things poorly. Many times this is the result of multiple undeliberate pivots in a short period of time. Don’t get me wrong, I’m pro-pivot — I think the general idea encourages fast iteration. However, I think sometimes entrepreneurs pivot poorly. They are so stuck on the product they’ve built (sunk cost fallacy) that they fail to extricate themselves from the trenches of building a product to reevaluate the overall problem they are trying to solve.

They end up with a Frankenstein of a product that does nothing well, a jack of all trades, master of nothing. The product “pivot” ends up being a hammer in search of a nail, rather than the other way around. Because they’ve spent so much time building out the product, the mental bias is that there has to be some value to the product they’ve built; it is easy to mistakenly correlate time spent building the product with market need.

Phin Barnes put it well — that the best entrepreneurs have a sense of their True North. In all of their product pivots, they are able to make decisions that move them closer to their True North.

The entrepreneur’s job is to synthesize all of this feedback and test your assumptions in a methodical and deliberate manner.

Without a product True North, you end up wasting time optimizing on a local maximum and building a Frankenstein Product.

(Stay tuned for a follow up post on a framework to avoid building a Frankenstein product.)