Grit, Generosity, Skillz and 14 Lessons from my Career in Finance

Grit, Generosity, Skillz and 14 Lessons from my Career in Finance

And actionable steps to becoming a ninja in the process

The 3-S Playbook

I worked in finance for fifteen years investing in Hedge Funds at Blackrock. I recently left to pursue a more entrepreneurial path (notably RadReads) but over the years reflected on the playbook that I had used to guide me throughout my career. I distilled it down to the 3–S: Skill, Self, and Surroundings. And after each section, I include extra credit “exercises” to help you achieve that Ninja Status.

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1. Skills

Master your craft …

I know this is obvious and I promise you much more if you read on. Many people feel like once they’ve graduated from college the learning stops, with the exception of some on-the-job training and a stint at grad school. However, it is imperative to continue to improve upon your skills with fervor, enthusiasm, and dedication. The first way is to go to the original texts in your line of work. In fact, take it a step further, read textbooks. Do practice problems, exercises, etc. You work out at a gym on a regular basis, why wouldn’t you do so for your brain?

Study the history of your craft, particularly where things went wrong. If you are an investor, study financial crises such as the Great Depression, Black Friday, Dot Com, and the global credit crisis. Study transformational events/deals/regulation. General Patton and Napoleon were both known to have studied thousands of historical battles and tactics. Modern artists have studied the works of the masters, practiced sculpture, and perfected their crafts using various mediums.

And finally, take advantage of the access provided to you via the Internet’s connectivity. In the world of MOOCs, YouTube, academic journal repositories, and blogs, there is no shortage of available and high quality information.

Take the Milken Conference, an exclusive and expensive conference featuring leaders from all industries. The conference is invite-only and costs over $5k to attend— the entire conference is available on YouTube, for free and in HD Video (over 100 hours worth). Take advantage of this.


Ninja status: Read academic materials outside of your professional field to expand your breadth.

… But make sure you have breadth

Versatility = championships.

Let’s compare two of the top forwards in the NBA today: LeBron James and Carmelo Anthony. Without getting into “inside basketball,” Carmelo is an inferior player because he is primarily a scorer. In addition to being a scorer, Lebron is an excellent passer, defender, rebounder, and (more recently) thrives as a leader.

Once you master and grow your skills (from the previous sections) the next step is to become a voracious consumer of information, particularly through reading. It is rare to not read about an accomplished CEO who is an avid reader. Bill Gates reads a book a week on average and Teddy Roosevelt is rumored to have read ten thousand books in his life time.

Bill Gates brings his Kindle on vacation

Make sure that you get breadth in what you read. My personal rule is to read a finance book, a fiction book, and a non-fiction/business book on a regular rotation. For news, I try to seek out international publications (i.e. Financial Times vs. WSJ) and for political events both sides of the debate (i.e. Haaretz vs. Al-Jazeera for mid-east conflict).


Ninja Status #1: Ask your friends who have attended business school to recommend their favorite (Stanford GSB) and case studies (Harvard Business School, sorted by popularity).

Ninja Status #2: Do not assume that a book can only be read once. In fact, writing a quick summary of personal takeaways, then reviewing it once a year helps keep the ideas top of mind.

Ninja Status #3: Sprinkle in things that take you out of your comfort zone: poetry, science fiction, philosophy, fan fiction, books written in other languages.

This enables you to pass the “dinner table test”

To test if you have both mastered your craft and covered enough breadth, try this: think about the founder of your firm, CIO, or biggest client. He/She invites you to a four course dinner for just the two of you. Can you hang?

Early in one’s career, you may only feel confident enough speaking about “the things you are working on.” But guess what, Ms. CEO is not concerned with the spreadsheet you are working on or the small feature you’ve developed. She wants to talk about the future of the industry, how current events could impact competitive dynamic, the book she read on the plane, and company culture. And then there’s a good chance that 15 unrelated and random topics will be brought to the fore, all of which she is expecting you to know about, or even better, have an opinion about. This hypothetical dinner eventually turns into a real dinner — they are tough, but with time they become treasure troves of experience and pearls of wisdom and insight.

Beware and “be aware” of your behavioral biases

Have you ever held a view to be true in your head and somehow every piece of evidence supported this view? This is known as the confirmation bias. These behavioral biases represent lapses in our minds that usually rear their heads at the most inopportune time when decisions need to be made. 
A key component of self-awareness is (a) identifying such biases (here’s a summary and a great book) and (b) not succumbing to them. Failure to acknowledge them can lead to bad situations such as blowing yourself up in front of your boss or worse, being manipulated in an argument and negotiation by someone who is toying with your own. 
As you understand these biases, I would then create a checklist around the key biases to serve as a reference around key decisions. Two sets of decisions very susceptible to behavioral biases: hiring and investments (especially when they go bad).


Ninja Status: Identifying others’ behavioral biases and using them in a pitch or negotiation.

Non-linear thinking and understanding how options work

Our minds tend to work linearly, it’s much simpler that way: A leads to B, B to C and we organize our thinking this way. But alas, life is not so simple. And as one tries to connect dots and develop intuition (i.e. the proverbial “thinking outside the box”) it is critical to see the world through a non-linear lens. 
Options are a good way of practicing this thought framework. I’ll start with financial options, but will transition into much broader applications of the concept.
Simply defined, an option is the right (but not the obligation) to buy(receive)/sell something at a pre-determined price and pre-determined date. Pioneering research in the 70s led to the Black-Scholes model for pricing options. Again, grossly simplified but the key assumptions are:

  • the price of the “item” to be bought/sold at the future date
  • the amount of time outstanding
  • how much the price of the “item” moves around (“volatility”)
  • (Finance folk, I know I’ve left many out)

What makes options more complicated is that they are non-linear. If the price of the “item” goes up by $1 you are generally not better off by a $1, so the pay-offs are much harder to calculate and understand.

So why does this matter? Here are some real world scenarios that are options. Putting a deposit to rent an apartment, buying health insurance, investing in a seed round to get a look at series A, and buying an engagement ring (Baby, I swear I didn’t think of our marriage this way).

Ninja Status: Identifying when you are being offered or given a mis-priced option.

Learn to sell by telling a story

Everyone loves a good story. Over one’s career (and lifetime), you will realize that there are countless situations where you will have to persuade someone (or a group of people) about a specific view. Here are a few examples:

  • An investment committee meeting
  • A negotiation
  • Communicating your strategic vision to a team
  • Proposing to your wife (“Baby, this is why you should say yes”)

In many instances, you will come armed with countless arguments, bullet points, and counterpoints. However, often times both audience and presenter get caught in the minutiae which leads to a logjam or lack of conviction/persuasion. Stories are simple, but draw out the key messages in a way that often leads to an emotional connection. Learning to use stories is challenging and requires a theme that reoccurs throughout this post, breadth of experiences, curiosity, and the ability to connect the dots.

2. Self

Grit. Hustle. #beastmode

We’ve all heard the stories. Kobe Bryant was always the first to practice and last to leave. Jerry Rice had some of the hardest off-season conditioning program consisting of wind-sprints, hills, and weight lifting. Grit (or #beastmode) is a hard quality to define, but you know right away when you see it. Here’s Caron Butler on Kobe Bryant.

“Work ethic,” Butler said. “He comes to the gym 6:30, 7 in the morning, gets shots every day, a rhythm. Afterward hits the weight room, works out in the summer, studying film, critiquing guys, watching their tendencies, picking things up … Just studying the game with him taught me a lot.”

Here’s my attempt to define #beastmode.

  • Putting in that extra little burst of effort. (Doing this over a long career will lead to very diverging paths of success)
  • Thriving in difficult situations instead of easy ones.
  • Not taking the path of least resistance
  • Not looking at problems in a black or white manner

#beastmode is mostly mental, but part physical (and we’ll address that in greater detail below). You will not be rewarded for grit on day one. In fact, by definition grit manifests itself over time, but its compounding effect is similar to that of leaving money in a bank account or the markets over extended periods of time.


Ninja Status: Pick a month where you say “yes” to everything that’s asked of you.

Delayed Gratification — It’s a sprint not a marathon

“I own you.” “No. I own YOU”

Getting to #beastmode requires mastering delayed gratification. The Stanford Marshmallow Experiment conducted in the ‘60s measured the long term effect of this. Kids were given the option of one small reward (marshmallow) immediately or two marshmallows 15 minutes later. The group that was able to wait 15 minutes developed strategies to distract themselves, like singing, walking around, or closing their eyes. These children were then tracked at age 14 and 18 and tended to be more self-confident, popular with peers, able to cope with frustration, and scored an average of 210 points higher on the SATs.

Sprinkle some productivity on those grit(s)

It is not enough to just have grit, you must learn to be efficient in how you use your resources (time and mindspace). I will not bore you with details about which productivity system to use (I am an Omnifocus disciple) but a few good articles can be found here (via First Round Review and How to Scale Yourself). What I’d like you remember on productivity is the following:

  • Have a system and stick to it
  • Do not respond to email in the morning, in fact,…
  • “Eat that frog” — perform your highest impact (or most dreaded task first)
  • Engage in positive rituals (like not checking your email in the morning, or working out in the morning)
  • “Chunk” your time. Do one group of things (i.e. read, respond to email, make phone calls) in sequence — switching contexts is very exhausting and inefficient (it takes your brain a few seconds to resume a context)
  • Do not multi-task (more on “focus” below)


Ninja Status: Read and master David Allen’s “GTD” philosophy.

Leave your comfort zone — often and for extended periods of time

Muscle confusion is a technique of physical training adopted by various workout regimes including CrossFit and P90x. These workouts seek to address the problem that continuous repetition leads to stagnant muscle growth, or even worse, atrophy… so they mix things up, to constantly keep your body guessing.

I’m a big believer in “brain confusion,” to keep your mind from not atrophying away. I think that there are two ways to do this: constantly challenging yourself by learning new things and by taking yourself out of your comfort zone.

I’ll share my experience on the first one. From ages fifteen to around 25, I read a lot. Mostly textbooks and academic papers, and to a lesser extent non-fiction. I never read fiction, I thought it was a waste of time because I had convinced myself that I “wasn’t learning any skills.”

Like many things in life, a personal change was undertaken given the motivation of a then-girlfriend, who was shocked at this arbitrary rule and even stupider justification. From then, I intertwined a decent amount of fiction into my life and it’s been one of the most rewarding changes I’ve made. (My personal goal is tackling the Top 100 books in the English language over my lifetime). Besides the sheer joy of time traveling (both past and future), humor, adventure, and much much more, reading fiction has helped me become more empathetic by understanding different perspectives, modes of thinking, and the beautiful complexity of emotions. (Side note — Bill Gates and Jeff Bezos have very differing views on this.)

Leaving your comfort zone is one way to develop grit. Here there are the obvious categories that usually combine a physical and mental challenge such as marathons, triathlons, and combat sports. But the physical component is not always a pre-requisite and these ultimately become personal decisions. Those who are shy or eschew public speaking might try stand-up comedy or acting classes. The rhythmically challenged might try dance classes, those who don’t like kids might take up mentoring.

These “bigger challenges” should be paired up with some smaller “micro challenges,” again to test your discipline, delayed gratification, and grit muscles. Some might put this into the “life hacking” category (a classification that I wouldn’t disagree with) — a few I’ve tried over the years are: cutting out caffeine for a month (just to know that I wasn’t addicted), writing emails without explanation points (an easy crutch around solid word selection), and turning off all devices for 24 hours on Friday nights.


Ninja Status: One big challenge per month and one micro challenge per month.

The F-Bomb: “FOCUS”

At this point, I may expose myself as the old man (35 year-old) that I am and lose credibility in the eyes of many millennials. I strongly hold the view that multi-tasking is inefficient. I’ll explain why:

Let’s be generous and say that every time you switch contexts (i.e. to check email, gChat, social media, respond to a notification, “alt-tab” for you old geezers) it takes you 10 seconds (I think the actual number is greater) to acknowledge the notification and for your mind to refocus on the prior task at hand. Let’s say you get one of these interruptions every 3 minutes (again, I think the number is greater). For arguments sake, you have a 9-5 workday which leads to the following math:

(8 hours) x (20 interruptions per hour) x (15 seconds of context switching) = 40 minutes

That’s 40 minutes PER DAY, and in the above example, which is almost 10% of your workday! (I personally think the numbers are more like 8, 30, 20 which equals 1 hour and 20 minutes per day.)

My advice to combat this is to “chunk your time” and to schedule bursts of productivity. Chunking will save you the drag in context switching (I’m not saying to abandon those mid-day tweets!) and using techniques such as the the Pomodoro Technique (25 minutes of work uninterrupted followed by a 5 minute break) for bursts of productivity.

With focus comes the ability to execute but also have clarity in perspective. How is one supposed to make critical and insightful decisions if you have the equivalent of Hungry Hungry Hippos going on in your mind?


Ninja Status #1: Meditation. I’ve struggled to develop a consistent practice, but I am confident that this is a good philosophy to develop the focus and calmness skills.

Ninja Status #2: Digital detox — cutting out all electronic devices and connectivity to the internet for a 24 hour period.

Ninja Status #3: The Pomodoro equivalent for working out is the Tabata Method.


You never really understand a person until you consider things from his point of view… Until you climb into his skin and walk around in it.” 
– Spoken by Atticus Finch in Harper Lee’s “To Kill a Mockingbird”

The dictionary definition of empathy is: the ability to understand and share the feelings of another. I don’t think that I really understood what empathy meant until I was in my mid-twenties. I’ve since realized that empathy is the key way to build meaningful relationships and connections. It’s still a difficult concept to wrap my arms around, let along explain how to develop this type of awareness, but here’s an attempt:

First, listen and observe. That means put the iPhone down and watch how people live. Look at their “tells,” listen deeply and attentively to their stories, and try to visualize the circumstances around them. Second, have a diverse set of experiences to draw upon. This can include some of the earlier comments on reading, having conversations with strangers, traveling to foreign countries. Third, a very simple exercise consists of observing strangers (on a subway, for example) and creating stories in your head about them. You should be mindful of not stereotyping and accepting of the fact that you will never know “the answer,” but it’s a fun exercise. Finally, I’ve found that writing (even if it’s just a journal for yourself) helps take those observations and experiences and create narratives around them. Daniel Goleman brought the concept of empathy and Emotional Intelligence to the fore of business leaders in 1995.


Ninja Status 1: Schedule a fixed amount of time (say 30 minutes) a week to write. Pick a character (taxi driver, child, parent) and write from their perspective.

Ninja Status 2: Challenge yourself to write either 1 page in the morning or at night every day for 30 days and see what 1) was most surprising, 2) influential and 3) best moment.

3. Surroundings

Give. Don’t take (or match)

The mantra “nice guys/girls finish last” is bullshit. Centering yourself around making those around you better is the ultimate philosophy for both a fulfilled life, rich set of experiences, and professional success.

Before I dive in, I would like to acknowledge my friend Adam Grant, and his must-read book Give and Take. Not only does he wholeheartedly embrace the “giver” philosophy, but his book (and related thought leadership) has been highly inspirational to me.

But first, a few definitions. What is a “giver?” Is it someone who donates money? Or someone who volunteers a lot? While these would certainly qualify, what I’m referring to is more of a mindset, which is accompanied by “micro” acts of generosity. It might help to describe “takers” and “matchers.” Takers are easy to recognize and are those who always seek to be out for themselves. They quickly size you up to see what you can do for them, go for the ask, and then disappear to never be heard from again.

Matchers, on the other hand are more balanced and represent the majority of folks out there. They will scratch your back, in exchange for a back scratch of their own. They offer help when there is an implicit (and sometimes explicit) quid pro quo and seem to operate with a mental “balance sheet” of those who have helped them and how they have reciprocated. In our highly transactional and competitive world, we are taught to be matchers.

But then there are the givers. They offer you help (in the form of time, advice, introductions to their network). They seem to have endless amount of time and energy, they always follow-up, and yet they never ask for something in exchange. In fact, sometimes they might just disappear for a few months, only to resurface by asking you how they could be of assistance.

I love the double-entendre the phrase “lead by giving” because those who genuinely seek to make others around them better are ultimately the most inspiring folks whom we want to be led by. So how does one “become a giver?” First, like Fight Club, you never talk about being a giver. Second, you listen more than you talk. When this happens, the other person on the receiving end of your conversation will begin to surface out aspirations, struggles, and passions, which you should carefully register in your mind (more on this below). Third, you should spend some time thinking about how you could helpful. This could include

  • An introduction to a person in your network
  • An article, blog post, tweet, or book that may be of interest
  • Dedicating some time to provide feedback on a pitchbook, resume, blog post, brain storm

I’d note that this generosity doesn’t have to be purely professional — in fact, oftentimes it starts around hobbies and passions, and over time build into more “professional” things.

A quick personal example revolves around a quick email newsletter I put together a few months ago called “Daddy Tips.” As a new dad (and hence the furthest thing from being an expert) each week I would do the following: jot down a few observations of things that seemed to be working for us with our newborn, capture a few relevant links that I had read, and share some products that were working/not working for us. I had approximately a dozen dad friends who had kids the same age and would share these tips in a crude MailChimp email every Sunday. It would take around 10 minutes to put together, but with time the list grew to 40+ recipients, many of whom have been highly appreciative of my observations. I use this example to show that a) I am striving to live the “giver” philosophy and b) small acts can benefit a large number of people in the most unexpected situations.


Ninja Status: Every time you meet someone new, ask them “How can I be helpful to you?” Once you have had some time to think about this request, if you can help them than do so; if you can’t, acknowledge that you couldn’t do so at that specific moment. But keep that “ask” in the back of your mind as you go about your day, and chances are, eventually you will be able to help.

Make Lots of Introductions

The mutually beneficial introduction (“MBI”) goes as follows: find two awesome people in your network. Typically (but not always) there will be some commonality in profession, hobbies, and personality. The beauty of the MBI is that it is almost a travesty that these two folks have not met. You send an email, and then “voila.” A few rules to keep in mind around the MBI:

  • Always use the double opt-in — that is, send an email to both parties, seeing if an intro makes sense.
  • Consider the recipient’s personalities — a brash entrepreneur might not get along with a reserved investor.
  • In the email, link to the relevant pieces of information, to make it very easy for the parties to evaluate (i.e. link to their LinkedIn, company home page… the Refresh app comes in handy here)
  • Get feedback from both parties to tailor your MBI algorithm going forward.
  • Recognize that ultimately your reputation is on the line when you make these introductions

With time, the MBI will serve as your greatest tool as a giver, enabling you to accelerate serendipity with pinpoint precision, and then leverage your growing network. I’m reminded of one of my favorite Benjamin Franklin quotes, which applies to work, but clearly also to MBIs.


Ninja Status: Target 1 MBI per week, ultimately moving up to 1 MBI per day.

Strengthen those weak ties

When you go out to meet new people, it is common to dip within your social circle to grow your “network.” It’s the path of least resistance and we instinctively get comfort from the “known knowns.” However, fast forward your life 5 years forward… you hang out with your college friends who happen to work in the same industry. As a result, you go to the same weddings, vacation spots, read the same publications, and shop from the same stores. I know that I’m overgeneralizing and run the risk of being condescending, but please bear with me.

The same principles of muscle confusion for fitness and “mental” confusion to keep your neurons intact, also apply to ones network. This may feel challenging, and I can relate, I’ve had one-off meetings with accomplished music industry and advertising executives, two fields that I know absolutely nothing about… this is where the “dinner table test comes in handy!” These meetings ultimately have become great friendships and collaboration partners. More importantly, they have served as “bridging networks” into entire new social groups, many of which have directly benefited me both personally and professionally. So the next time someone offers you an introduction where you have zero common contacts — thank them profusely!


Ninja Status: Research “dormant ties,” former close connections with whom you’ve been out of touch with for more than 3 years. Surprisingly, (especially if you aspire to the “giver” ethos), those friends will be happy to get the email from you asking how you could be helpful.

360 Mentoring

The dictionary definition of mentoring is:

Men·tor: Advise or train (someone, especially a younger colleague).

From this point on, I’d like you to dump the above parenthetical. Instead, think of mentoring in three ways: down, lateral, and up.

  • Mentor “down:” Traditional form of mentoring where someone older advises someone younger.
  • Mentor “laterally:” Mentoring peers — especially those where you can help them build complimentary skill sets. For example, as an engineer, you may have minimal interaction with the sales team, especially at the junior level. By teaching them some elements of what you do, or answering some questions, you are empowering them with both knowledge and context. But most importantly, you are showing that you care about them.
  • Mentor “up:” This is the hardest category because the traditional corporate hierarchies frown upon this type of conversation. Yet we all have critical feedback for our bosses, and it’s usually for the benefit of all. However, communicating this feedback requires a bit of strategizing around the timing and method of delivery. I have found that being straightforward (and maybe not overly critical) usually works best. Finally, as the technology gap between digital natives and their old bosses widens, “reverse mentoring” has become a more popular topic.


Ninja Status: These three types of mentoring can also be accomplished virtually, via Skype, social media, and email.

Shaun White believes in 720 degree mentoring

Develop a Personal CRM system

Weak ties, MBIs, connections, sending relevant blog posts… you’re probably asking yourself, how the hell am I supposed to keep track of all of this? Ah, grasshopper, if I were to share the secret with you, I may have to end you!

All jokes aside, the truth is that there is no one tool that helps keep all of this information organized and handy. But I can propose a few recommendations:

  • Reminders to connect: For every person you ever meet, I would set a reminder to re-connect with them at a pre-specified point in time. The peer that always inspires you, maybe once a month. Random guy from a conference, maybe once a year. Possible tools: Any “to-do” list, calendar reminders, Boomerang, actual CRM system (Highrise, Zoho).
  • Categorization of your network: Whenever I meet someone, I try to quickly identify them with a few keywords in four categories: Industry (tech, finance, fashion), Function (lawyer, biz dev, coder, angel), Passions (Crossfit, chess, environmental), and personality traits (connector, salesmen, introvert, intellectual). While far from an exact science, it helps the mental process of calibrating relevant intros and being helpful in the future. Possible tools: Evernote, Google sheets, LinkedIn Contacts.
  • Sharing of relevant info: Ideally, you can then organize your network into themes. For example, I have a dozen mailing lists where I pass along interesting reading material. They range from “People who like Management Articles” to “FinTech Investor” to “Sneakerheads” (i.e. those who love sneakers). This becomes pretty cumbersome to manage but a very powerful way to give to your network. Possible tools: Gmail or MailChimp mailing lists.

This is a lot. I hear ya guys, but it’s many years of experience distilled into some key takeaways. Dip your toes in it, try a few over the year, and then dive back in.

And remember, it takes years to become a Ninja!

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