The Optionality Trap

The optionality trap starts when we’re young:

“Get good grades in school. You’ll have more options when choosing a college.” -Parents

“Pick a major that applies to many different industries. That way you’ll have more job options.” -College Counselor

“Consulting is a great field. From there, you can do whatever you want.” -Career Advisor

While this advice isn’t necessarily wrong, very rarely do we take a step back and examine what exactly we’re collecting all these options for. Perhaps at the beginning of our careers, we have some vague idea of a goal or accomplishment we want to reach but we’re not quite sure: a) how to reach the goal and b) if we even want to reach the goal in the first place. So naturally we choose the path that keeps the maximum number of future possibilities available to us. Unfortunately, this fuzzy goal mindset is often carried through to adulthood and leaves us grasping for optionality with all of our major life decisions. And over the course of a lifetime, this optionality maximization mentality turns us into habitual option collectors and prevents us from reaching our goals.

But I’m getting ahead of myself. Let’s start with the basics.

What is Optionality?

Optionality is a concept from the finance world. When someone holds an option, it means they have the right to do something but no obligation to do it. As Mihir A. Desai puts it in his Crimson article, “Optionality is the state of enjoying possibilities without being on the hook to do anything.”

When the universe conspires in your favor, you participate in the upside. And when it doesn’t, you aren’t on the hook for the negative consequences. It sounds pretty great, doesn’t it? In finance, this is referred to as a “non-linear payoff”, which literally means you stand more to gain than you do to lose.

Thanks to books like Antifragile, the idea of optionality has become popular in the mainstream. Predictably, people are very interested in the idea of having possibilities without any obligations. The optionality concept has been applied to things like careers (picking a job that opens up as many future opportunities as possible), relationships (dating around and not making commitments because you never know who else you’ll meet), and more.

Of course, in the financial world, every option has a cost associated with it. And so do real world options. But while financial options have an explicit price attached to them, real world options have more subtle costs.

What is The Optionality Trap?

When we first start making life decisions on the basis of the future options they create for us, we do so to reach some long-term goal. Perhaps we want to someday travel the world or start a company. Maybe we want to build enough skills and reputation so we can work on our own schedule. Or most common, we just don’t know what we want to do so picking an option that gives us more options seems to make the most sense.

However, when we do this for long enough, it becomes a habit and we start making all of our decisions through the lens of future optionality. After awhile, we aren’t even conscious of this rationale. We post-rationalize decisions and think we want to go to business school or consulting for their own sake but really, we’re optimizing for the opportunities we’ll have afterwards. Quoting Mihir Desai again:

The Yale undergraduate goes to work at McKinsey for two years, then comes to Harvard Business School, then graduates and goes to work Goldman Sachs and leaves after several years to work at Blackstone. Optionality abounds!

The optionality trap is something that ensnares us, not through outside forces, but through our own risk aversion and indecisiveness.

My opinion is that the optionality trap originates from an aversion to being hurt emotionally. A desire to avoid emotional pain is of course, completely natural. But in this avoidance lies an emotional stuntedness that prevents us from ever trying anything worthwhile and learning through the process.

Common Optionality Trap Examples

The optionality trap can affect more than just our career choices:

Startup Ideas

Let’s face it: coming up with startup ideas is not hard. The hard part is determining if your idea is viable and then of course, executing on it. And yet there are thousands and thousands of potential entrepreneurs sitting on the sidelines with a concept or an idea that “isn’t quite ready yet”.

Guess what? It’s never going to be ready. Instead of getting started with customer development to see if their idea has legs, these would-be entrepreneurs are keeping the option of being an entrepreneur alive, while not engaging in any of the emotional (ego) risk of being wrong.

If you have ideas, start testing them.

I also often see entrepreneurs who come up with tons of ideas but can’t pick one to go deep on. This is a close cousin of the “not ready yet” problem. These entrepreneurs are giving themselves optionality but never actually selecting one of their options.

As Chaz Giles frequently reminds me when I try to get “clever” with startup ideas, “Someone has built a profitable business selling bird diapers. Don’t overthink it.”

By focusing on optionality of ideas over execution, would-be entrepreneurs will never succeed. But perhaps more importantly, they will never make mistakes and in the process, completely stunt their own learning curve.

Corporate Innovation

Individuals aren’t the only ones guilty of optimizing for optionality. Companies frequently do it too.

In companies, the optionality trap is often seen in the insidious form of endless meetings, which leads to decision-making procrastination. Quite simply, companies that don’t make decisions can’t be wrong. Actually, that’s not true at all – by not making decisions, companies are defaulting to making the wrong decision. But the individuals at the company (a key distinction) get to avoid making a decision which could potentially be wrong, which means they avoid any potential blame.

This is once again the optionality trap at work. By not making decisions, individuals within a company keep all their options open. But by not making a decision, their company (which ultimately includes them) fails at solving whatever problem they were trying to solve.

Dating

The optionality trap in dating is the ultimate modern day problem. When you can login to a dating app and get access to a huge number of single people, it becomes tough to commit to anyone. What if there’s someone better just on the other side of that app?

Plus, as you get to know someone, their flaws start coming out while the ephemeral “people” on the dating apps are still perfect. At least in theory.

When you live with the belief that there are people better than your current fling just a tap away, it becomes impossible to emotionally commit to someone. And without emotional commitment, no relationship can flourish.

Living Situation

For those lucky few who have the option to live wherever they want, the easiest thing to do is to live nowhere. I’m referring, of course, to the currently en vogue nomad lifestyle. Don’t get me wrong: the ability to live and work anywhere is generally awesome. Lord knows I’ve taken full advantage of it. But there are downsides that very few people talk about. For example:

When a person spends all his time in foreign travel, he ends by having many acquaintances, but no friends.

This quote about the nomad lifestyle was made by Seneca in Letter II of Letters From A Stoic, which is about 2000 years old but still holds true today. By not living anywhere, you experience a wide variety of locations but never develop deep relationships with people and place that someone who lives in the same area for years would enjoy.

How To Get Out of The Optionality Trap

You’re probably sitting there thinking to yourself, all this talk about optionality traps is fine but HOW do you actually make a decision? If you’re looking at two options with different risk profiles and appeal, how in the world do you decide which one to go for? Andy Dunn from Bonobos says it better than I can:

The risk is not in doing something that feels risky. The risk is in not doing something that feels risky.

Very little is obvious in the research on human decision-making and happiness. Very few things are proven. One thing that is proven is this: the only regrets octogenarians have are for the risks not taken.

Here’s why:

If the risk taken does pan out, it is good. But if it doesn’t — and here’s the key thing — we find a way to justify the risk taken as learning.

That’s the secret.

If our goal is to live a good life without regrets, it’s so important to internalize Dunn’s quote. If we choose the path that doesn’t speak to our souls but feels safer, there’s a very strong likelihood that we’ll ask that dreaded question years later: What if? What if we took the plunge?

But if we choose the risky path and it doesn’t work out, we can (usually) call it a learning experience and move on. There’s very little thinking about what would have happened if we had taken the safe path.

By knowing this and then projecting to how you’ll feel in 10, 20, or even 40 years out as a result of this decision, you can take on the fear that quite naturally arises at a decision point. And by taking fear out of the equation, you can make a decision that’s based on what you actually want, rather than basing it on what’s safe or comfortable.

Is There a Time and Place For Optionality?

Despite what you may think from my railing against the optionality mindset for the past ~1800 words, there are plenty of times in my life where I’ve chosen optionality over the more direct path. While I do regret some of those decisions, there are a couple times that I’ve chosen optionality and it worked out.

Like most complex matters, there’s no “one size fits all” solution to decision-making. Big life decisions are deeply personal. Even something like deciding to go into consulting, which on the surface seems like it’s driven by optionality, can be a courageous decision depending on what the motivation is.

Ultimately though, if you know you want something, the fastest way to get there is to chase it directly. Optionality is a backup tactic, not something to pursue first.

Closing Thoughts

The siren call of optionality is admittedly an alluring one. But it’s also dangerous. Unfortunately, when we don’t know what to do or the path to our goals is unclear, the easy default choice is to defer and pick something that gives us the most future choices. But the universe is strange. When we choose a path, things start to happen. Things we can’t necessarily predict in advance. Andy Dunn says it nicely:

If you can’t decide what to do, get on the road. You won’t find the answer. It will find you.

In other words, go punch the optionality trap in the nose and get after it.


Further Reading:

Mihir A. Desai’s Harvard Commencement Address

The Risk Not Taken by Andy Dunn

Antifragile by Nassim Taleb

Letters From A Stoic by Seneca

Losing the Beginner’s Mind: FIDM Recap

Last week, I had the opportunity to give a talk on product innovation at the Fashion Institute of Design & Merchandising (FIDM). While I think they called me in to share some of the things I’ve learned during my time consulting to The Estee Lauder Companies, it’s hard to say who got more value out of the talk: the students or me.

I’ve switched industries a lot in my (admittedly) short career. Over the past few years, I’ve worked in higher education, early education, ad tech SaaS, cosmetics, and alcohol. Because of that frequent switching, I’ve often been a beginner and forced to get up to speed in new industries quickly. However, during the Q&A portion of the talk at FIDM, I realized I had stopped looking at the cosmetics industry through a beginner’s eyes. The students (all of whom were about 20 years old) were asking questions about the industry, sales channels, and technology from angles I had never thought of but seemed obvious as soon as they brought them up.

For example: among millennials, beauty influencers have huge power to drive sales, simply by recommending a product or featuring it in a makeup tutorial video. Several students brought up the (valid) point of diminishing consumer trust in influencers because of all the undisclosed sponsored posts. In hindsight, this concern seems obvious but in all my time working with beauty brands, this point has either been completely avoided or jokingly brushed off. Yet these students were able to very easily see the long-term consequences of the current influencer trend: diminished consumer trust. Instead of working with influencers or celebrities, these students were interested in figuring out how to build better peer-to-peer recommendation systems that start and end with product effectiveness in a personalized way and can’t be gamed by larger brands. Amazing concept!

What surprised me the most about the FIDM Q&A session is how unaware I was of losing my “beginner’s mind“. I’ve only been in the beauty industry for two and a half years – which is nothing if you compare it to colleagues who’ve been doing this for twenty or thirty years. But those two years were more than enough to make me miss obvious concerns with the current trendy marketing strategy. This brings up an important question: at what point do people lose their “beginner’s mind” and is it possible to keep this creative state of mind for longer periods of time?

At this point, I don’t quite know what the best solution is but I suspect it has something to do with continually exposing yourself to others without much experience and limiting your interactions with so-called “experts”. While I’m sure there’s some value in having deep knowledge within a specific field, it certainly does seem like the more time you spend working on a given problem, the more difficult it is to see the tangential opportunities that might be obvious to a beginner.

I’ll be exploring this beginner/expert dichotomy further in future posts but in the meantime, let me know your thoughts or experiences with the beginner’s mind on Twitter or in the comments!

Greatness All Around Us

We’ve all heard the cliché that we become the average of the five people we spend the most time with. Without a doubt, humans are massively influenced by those we surround ourselves with. Hang out with people who drink every day? Chances are, you’ll start drinking every day too. If your friends are workaholics, you’re more likely to be a workaholic. Accordingly, if we improve the quality of our peers, we can improve our own lives.

Of course, it’s not quite that simple. After all, we can’t just get rid of our friends and pick up “better” ones (nor should we want to). We can, however, surround ourselves with greatness by other means. Living in the Internet-era means it has literally never been easier to influence yourself through the positive examples of others. You just need to have the discipline to curate your environment with the right inputs.

Read Books – Especially Biographies

“Once you learn to read, you will be forever free”

-Frederick Douglass

If anyone knows the value of reading, it’s Frederick Douglass. In an era when teaching a slave to read was considered a major crime, Douglass became a voracious reader, partially through his own initiative and partially through the kindness of his master’s wife. Throughout his life, Douglass maintained that reading and knowledge have the power to free one from their present circumstances and improve their life.

Biographies and autobiographies are incredible resources for exposing yourself to real-world examples of how great individuals dealt with difficult circumstances. Even if you pay full price for your books, where else can you spend $20 and get a deep dive into the life of Abraham Lincoln, Steve Jobs, Andre Agassi, or countless others?

Another big advantage of biographies is they allow you to be mentored by the greatness of people who have been dead for hundreds, if not thousands of years. It’s not quite as good as witnessing events in real-time but it’s not a bad substitute.

Fiction is an underrated resource for surrounding yourself with greatness. After all, what we think of as “history” is usually fictionalized anyway, so why not learn from true fiction? There are tons of fictional characters who can provide positive examples for how we can act in our daily lives and there’s no reason not to learn from them. Books that come to mind are The Martian, the Harry Potter series, and the Hunger Games series.

Listen to Podcasts

If we’ve hung out recently, there’s a good chance I talked your ear off about podcasts. Although they’ve been around for awhile, I’m convinced that the podcast ecosystem is primed for hockey-stick growth. The content available now is just incredible. As more podcasts experiment with non-advertising driven business models, I expect the content quality will only increase.

Some of the best podcasts for exposing yourself to greatness take the form of interviews. Others are of the “lead by example” variety. Here are a few of my personal favorites:

All of these podcasts have deep libraries for you to dig into. Some episodes will really strike a chord – others won’t. Sample a few and discover what gets you going.

The best thing about podcasts is they make the person being interviewed seem more human and normal than articles, books, or video. When you hear incredibly accomplished individuals like Jamie Foxx, Jody Mitic, Lisa Randall, or Naval Ravikant in audio, there’s no embellishment by an author, no makeup turning them into flawless beings, and there’s simply a level of rawness that I haven’t seen elsewhere.

Finally, podcasts are a great way to make your commute useful. It doesn’t matter if you drive, take the bus, or ride the subway to work – podcasts are the ultimate way to turn that dead time into productive time.

Pay Attention to Pop Culture and Sports

Image Credit: CBS Sports

I’ll be the first to admit it – the attention we pay to pop culture (and yes, I’m including sports in this category) gets on my nerves sometimes. But that doesn’t mean it can’t be inspiring. I’m far more into sports than music, film, or other types of celebrities but there are powerful examples from every field. To name a few just from football:

  • Aaron Rodgers going from community college QB to an NFL MVP and Super Bowl winner (I’m biased on this one – Go Pack Go)
    • Lesson: It’s not about where you start, it’s where you end up.
  • The New England Patriots ridiculous Super Bowl LI comeback win yesterday over the Atlanta Falcons
    • Lesson: It isn’t over until it’s over.
  • Russell Wilson’s inspiring, Stoic reaction to throwing an interception at the goal line in Super Bowl XLIX, when his Seattle Seahawks lost to the New England Patriots.
    • Lesson: Be resilient when faced with adversity

***

I could go on for days with these examples. They are everywhere: basketball, music, books, movies, TV shows, tennis – you name it. It’s easier to surround ourselves with greatness today than at any other time in history. We just need to know where to look.

Staying In Shape While Traveling

Staying in shape, mentally and physically, is obviously important to overall well-being. Personally, I find my mind is sharper and more importantly, I’m a much happier person when I take care of myself physically.

Since last April, I’ve been traveling a ton for my consulting work, typically somewhere between 2-3 weeks every month. Traveling is something I love so I can’t complain too much about that buuuut it certainly makes staying in shape difficult. Before this travel madness started, I had a regular gym routine (3-4 days of lifting weights, 2-3 days of cardio) but that’s difficult to keep up when you’re in a different place almost every week. 

Over the past few months, I’ve learned a lot about staying in shape while traveling. As is usually the case with me, most of these lessons were learned the hard way:

Skip the hotel breakfast

Free hotel breakfasts are almost always god-awful, especially if you’re staying at a road warrior hotel, like Homewood Suites or Residence Inn. Tell me if this sounds familiar: Soggy, somewhat rubbery scrambled eggs, breakfast potatoes that taste like they’ve been out for weeks, and some strange processed meat as a side.

Oh, I forgot about the waffle maker.

Do yourself a favor and skip most of that. Maybe grab some eggs and toast if you’re really hungry. But probably the safest items to consume in a hotel breakfast are the coffee, tea, and juice. With all the other stuff, you’re going to be consuming amounts of sodium and sugar that’ll leave you feeling exhausted for the rest of the day.

So if you’re not going to eat breakfast at the hotel, what can you eat?

Find a grocery store

Grocery stores are amazing places. Even in the middle of nowhere, you can find a grocery store that sells healthy food. My advice is to go to a grocery store the day you arrive and pick up a few things. Obviously food choices are somewhat dependent on whether your hotel room has a fridge/microwave. Here’s what I typically buy, assuming there’s a fridge:

  • A few apples
  • Some nutrition bars (I like Nature Valley Oat & Honey bars)
  • Greek yogurt

That sounds like a solid breakfast to me.



Take advantage of free exercise

This is a concept I try to use all the time, not just when I’m traveling but it’s even more important on the road. The idea is this: if you have to do something, for example, go from the ground floor of the hotel to the 4th floor, there are two options available to you:

Option 1: Take the elevator

Option 2: Walk up the stairs

Even though option 2 is more energy intensive, it’ll take you to the same place as the elevator, you’ll burn a few calories, and you’ll probably save yourself the stress of waiting for an elevator that takes forever and the awkwardness of being in an elevator. Related question: aren’t elevators just the most awkward places ever?

Another great form of free exercise if you’re in a city is just walking to meetings instead of taking an Uber or cab.

Get good at hotel room workouts

hotel gym fail
Typical hotel gym

Let’s face it: hotel gyms leave a lot to be desired. That said, there are some great workouts which don’t require any equipment and can be done in your hotel room (like this and this). Start doing them regularly when you’re on the road and add your own variations to keep it interesting. The easiest exercises to do in a hotel room, no matter what size, are:

  • Pushups (all kinds)
  • Bodyweight squats
  • Lunges
  • All sorts of ab exercises
  • Stretching

Take advantage of real gyms when you’re home

On a related note, if you’re on the road regularly, it’s easy to get into a routine of laying on your couch and watching Netflix when you’re home. I love Netflix as much as the next person but make sure you squeeze in some “real gym” time when you’re home. A real gym is a place that has barbells, plates, machines, and space.

If I get home before 8pm from a trip, I try to squeeze in a short, gym session the same evening.

Free meals aren’t really free

One great thing about work travel is being able to expense your meals. That’s amazing right?! Well, yes and no.

The good news is that you can take advantage of being in a new place and try types of cuisine and restaurants you typically wouldn’t go to. In some industries (like the one I’m working in now), work travel can also entail fancy dinners which gives you an opportunity to try more upscale restaurants you probably wouldn’t choose on your own.

The downside? Well, all those meals might be covered by your company/client but that doesn’t mean the calories don’t count. Just because dessert is covered doesn’t mean you should get dessert.

Remember the “freshman 15” from college? (I do…) You see a similar effect among new consultants for a very similar reason. I remember when I first started college, the “coolest” thing was being able to drink soda with every meal. A few months later, despite being a college athlete, I had gained 15 pounds and it was pretty obvious that the soda needed to go. Don’t make the same mistake as 18-year-old Neil.: try to eat the same way on the road as you’d eat at home.

But that doesn’t mean you shouldn’t enjoy the perks of going to fancy restaurants! Just be smart about it.

Get sleep

For someone who travels a lot, I still haven’t learned how to properly sleep in hotel rooms. Almost without fail, I find it difficult to fall asleep the first night I’m in a new hotel room. Knowing that allows me to plan for it. Most nights I sleep for about 7 hours so on my first night in a new room, I’ll try to budget 8-9 hours for sleep, which gives me some time to toss and turn and still get a normal amount of sleep. It doesn’t always work but it helps. 

Skimping on sleep is a great way to get sick while traveling – probably the worst possible combination.

Avoid alcohol, especially late at night

Related to the above, drinking alcohol affects your quality of sleep and can also contribute to getting sick. If your travel requires you to fly, keep in mind that planes dehydrate you so drinking alcohol before, during, or immediately after a flight can be rough on your system (and on your skin). If you do choose to drink, just try to balance each drink with a glass of water and you should be able to avoid dehydration.

And yes, I learned this lesson in the worst possible way by going out in SF the night before a 6:30am flight (what the hell was I thinking?). Next time we’re in the same city, ask me for the story.

Buy a StandStand

If you haven’t heard of StandStand before, you need to check it out. Basically it’s a portable standing desk made of a three interlocking pieces of wood. Great product that travels nicely in a laptop bag.

Especially after sitting for a while in a plane/train, working on a standing desk instead of sitting down feels amazing. Trust me.

 

Traveling for work can sometimes (or usually) be rough but being smart about how you travel, eat, and move while on the road makes all the difference between a miserable trip and a productive one. I’ve been on both sides of the productive/miserable spectrum and believe me when I say the productive side is a lot more fun. Let me know if you have any other suggestions for staying in shape while traveling – I’d love to try it out. 

How To Get Up To Speed In Any Industry…Quickly

Getting started in a new industry can be super challenging but in today’s world of shorter stints with companies, quickly building working knowledge of a new industry is an extremely valuable and essential skill. Becoming fluent in your industry quickly means you start providing value sooner to your team, customers, employers, investors – everyone.

Back in the day (2012), I showed up to a lunch meeting in Pittsburgh with Adam Paulisick unprepared to answer his questions about the economics of college admissions, the industry I was running a company in at the time. He gave me some advice that stuck with me ever since: To win, you HAVE to know more about your industry than anyone else – there are no excuses.

Since that embarrassing episode, I’ve tried to apply Adam’s advice to everything I’ve done and developed a step by step process that makes the challenging process of getting up to speed in a new industry a bit more methodical:

Step 1: Read as much as you can about the market 

There’s nothing to replace this step. Read EVERYTHING – articles, journals, books, forums, industry history, even tweets. Don’t judge anything you read yet – at this point in the process, you don’t know anything. If there’s some kind of overview book, start with that – if not, start with articles because they’re usually written in layman’s terms. You should absolutely be taking notes – the key here is to start building a knowledge base. Allow yourself to go down the rabbit hole.

One last thing on this topic: give yourself the time you need to read about the industry. Study for this like you studied for the SAT and make sure you block the time off on your calendar. This is just as important as any meeting.

Step 2: Find people who know a lot about the market and spend time with them 

Talking to knowledgeable people and asking questions is something that should be done mostly in parallel with reading but make sure you’ve at least read a little bit first so you can ask relevant questions. Don’t worry about forming opinions yet – just keep building knowledge. Asking someone for their time initially feels scary (why would they want to talk to me?) but you’ll find that smart people: a) generally want to be helpful and b) are generous with their time when they sense you’re genuinely curious about their life’s work.

A simple hack here that’s been magical for me: Ask each person you talk to in the industry for one other person they recommend you talk to. Even better, ask if they can introduce you. Very quickly, you’ll have a network of really smart people who genuinely want to help you learn. #winning

Step 3: Form opinions and test them 

The first two steps in this process are fairly straightforward – they require work but your ego isn’t at stake. The third step is what will require some courage. To figure out if your mental “picture” of your new industry is correct, you’ll have to form some opinions AND get a reaction on those opinions from knowledgeable people. Without getting a reaction on your opinions, you’ll simply be forming a (likely) incomplete/incorrect mental map of the industry. Feedback is what allows you to correct, iterate, and improve on your mental map to create something resembling reality.

One of the most amazing things about the discovery process is that this is the stage where tons of ingenuity comes from, likely because at this stage, you’re reasoning from first principles (as opposed to ingrained dogma). Cherish this point of the process even though it’s scary sometimes. The worst-case scenario is that you say something stupid – no big deal.

Step 4: Repeat, repeat, repeat!

This process isn’t something that should only be done when you first start working in a new industry. It should be done constantly so that you continually grow your knowledge base and keep your mental map up to date. The ultimate goal is to have what athletes refer to as “fingertip feel” of your industry.

Bonus Tip: Your ego is your worst enemy 

All of the suggestions above require leaving your ego at home. If you can’t do that, all the feedback in the world won’t improve your mental map of any industry. Remember, feedback isn’t an insult – it’s a gift and a huge competitive advantage. Allow yourself to accept feedback and you’ll find that you’ve learned more about your industry in 6 months than most people learn in 10 years.

Sales Prep: How Do You Get In The Mindset To Sell?

On the surface of it, selling something is pretty weird. You’re basically using words, Jedi mind tricks, and (occasionally twisted) logic to convince someone that they should do something, which usually consists of them giving you money.

Oh and if you’re about to skip this post because you’re not a “salesperson”, let me ask you something: have you ever had a job interview? Have you ever pitched an idea? Have you ever asked your teacher for a deadline extension? Yea…you’re a salesperson. Don’t be ashamed, we’re all salespeople. Own it.

So if we absolutely have to do the uncomfortable act of selling something, we might as well do a good job right? The art of selling is first and foremost about confidence. If you don’t believe in what you’re selling, you can be damn sure no one else will either. Salespeople require a similar level of unshakeable confidence as athletes do and just like athletes, salespeople tend to have a “sales prep routine” to get into the right sales mindset. Here’s one that works for me:

Step 1: Watch these 2 videos (language NSFW) featuring Vin Diesel and Ben Affleck from the movie Boiler Room. Awesome demonstrations of sales techniques in here too:

Best quote from these videos: “There is no such thing as a no sales call. A sale is made on every call you make. Either you sell the client some stock or he sells you on a reason he can’t. Either way a sale is made”. Word.

Step 2: Review your plan – why should this person give you what you want?

I’m not a big believer in sales scripts. In my opinion, scripts are a great way to make yourself seem robotic and unlikeable (unless you know the script really, really well – so well that it’s second nature and you don’t have to think about it). That said, it’s still important to have a gameplan in place – where do you want the conversation to go, how you want it to flow, and what you want them to do. Most importantly, you have to be able to answer the question: why should the other person do what you want them to do?

Step 3: Review objections – why would someone say no to what you’re selling?

Inevitably when selling, someone is going to say no to you. The key is how you handle their objections. Obviously you need to know what the objection is in order to respond to it and improve in the future, so make sure you make the effort to find out. It amazes me how many people take “no” at face value in the sales process and completely miss the opportunity to iterate on their product/pitch. By understanding objections, at the very least you know what you can improve for next time. And yes, you should be writing these objections down.

Step 4: Watch Alec Baldwin motivate you to sell in Glengarry Glen Ross (language NSFW)

Remember: Always be closing!

On a more serious note though, the AIDA (Attention, Interest, Decision, Action) framework that Baldwin talks about is really, really effective. Learn it and use it.

Step 5: Go make the sale

You got this. Have fun with it – what’s the worst that’s gonna happen? They say no? Their loss.

Step 6: Drink some coffee (because coffee’s for closers only)

If you want to go deeper into learning sales skills, I highly, highly recommend buying Jeffrey Gitomer’s Sales Bible book and getting tons of real life practice. There aren’t any shortcuts to getting good at this stuff. It just takes confidence and hard work.

Failure: The Secret To Becoming Mentally Tough

Michael Jordan on failure

I’ve been noodling on a theory for awhile related to mental toughness. The theory is this: There‘s a huge difference in mental strength between those who’ve been “failure-tested” and those who haven’t. Failure-tested is a bit of a vague term so let me explain what I mean before diving in further.

When I say failure-tested, I’m not just talking about someone who has started a company and failed. That’s just one example. It can also include people who’ve gone through devastating injuries or accidents, recovered from an addiction, gone through a divorce, or any number of tragedies. The key to being failure-tested is not the event that constitutes “failure”, but the effect the event has on personal identity.

For example, when a football player gets an ACL tear and has to sit out for 12 months, are they still a football player? Of course they are but 12 months of not doing what you think you were born to do can shatter personal identity. If someone’s personal identity revolves around a company they started and that company fails, their personal identity is destroyed. The same thing happens if they self-identify as a husband and their marriage dissolves. My hypothesis is that true failure (and the negative mental effects associated with it, like depression) only occurs when someone’s personal identity is destroyed.

I started thinking about this as I read Sam Sheridan’s excellent books on martial arts: A Fighter’s Heart and The Fighter’s Mind. Sam talks about how the best thing about MMA (mixed martial arts) is that it allows you to use whatever style you want, from muay thai, to kung fu, to Brazilian Jiu Jitsu, and see if you can make your opponent “submit” (AKA “tap” or quit). When someone submits in MMA, the fight is over. It’s great because it makes it more unlikely for serious injuries to occur (since you have the option of quitting) but to a fighter, the act of submitting means that your opponent has total power over you – they could kill you, if it were a street fight.

When someone is forced to submit during an actual MMA fight, it can shatter the fighter’s world view and make it nearly impossible to get back in the cage, which by definition, requires you to think you can win. Yet unlike boxing, most of the best MMA fighters aren’t undefeated, so how is that possible? The answer is that these top fighters can take the mental beatdown that comes with failure, pick themselves back up, and improve for next time. It’s more than simply getting back up – these fighters actually get better after these losses. The losses push them further for next time.

How does this all tie into someone being failure-tested? When someone has experienced the pain that comes with their personal identity being shattered and comes back from it to take another shot at life, they’ve been failure-tested. I’ve noticed this a ton in the startup world – founders who’ve failed and try again are often some of the most mentally tough people in the industry (and most of them have failed at some point). You may argue with his methods but Uber CEO Travis Kalanick is a great example of this. At one point before Uber, “Kalanick was filing for Chapter 11 bankruptcy and sleeping in his parents’ house”. Uber is not Kalanick’s first company and he has definitely been failure-tested, probably in more ways than we are even aware of.

An even better example than Kalanick: When Elon Musk was at Paypal, he couldn’t afford an apartment so he lived in the office and showered at the local YMCA. Unrelated tangent: I used to work out at that same YMCA when I lived in the Bay Area (not during the same time period obviously). The trials for Musk didn’t end there though. He later invested ~100% of his (now massive) net worth into Tesla and SpaceX. At one point, he had to borrow money from friends to pay rent, despite being mega-rich on paper because Tesla couldn’t make payroll unless he put in his last $3 million into the company. Talk about being failure-tested – his life could’ve been a rags-to-riches-to-rags story. Instead, he’s now one of the most accomplished human beings of all time.

It’s no coincidence that there’s a large number of successful people who went through rough childhoods. Those early experiences shaped the way they would respond to difficulty for their lives.

So how does all this apply to you? There’s a lot I could say about this but overall it all sums up to one thing: take risks and put yourself in a position where you’re testing yourself. This all depends on you but could include things like:

  • Run further than you’ve ever run before
  • Lift something heavier than you’ve ever lifted
  • Start a new hobby
  • Try a new sport
  • Ask out that girl or guy that you’ve been afraid to
  • Write something

Yes, trying something new and testing yourself is going to feel awful….at first. Pretty quickly though, you’ll get used to it. Being frustrated is a great sign that you’re out of your comfort zone and on your way to growth.

I think there’s a lot more to say about this topic in many different areas – especially hiring and personal relationships but I’ll save that for future posts. This is already too long (that’s what she said….).

Russell Wilson, Adversity, and Stoicism

“Why didn’t they run it from the 1 with Marshawn?”

It’s something nearly everyone has wondered aloud in the past few days. For those of you who’ve been living under a rock, here’s what happened: the Patriots had a monstrous comeback in the 4th quarter to go up by 4. The Seahawks then stormed down the field thanks to some crazy plays like this one. They were down 4, had the ball at the 1 yard line with 1 timeout, 26 seconds to go, and had the best running back in the league in their backfield. On the next play, they decided to pass, it was intercepted and that sealed the game. The Patriots won, Tom Brady/Bill Belichick get their 4th title, and the Seahawks are left wondering what happened.

For most of us, having anything like that happen, let alone on the world’s biggest stage, would be absolutely devastating. What shocked me the most since then, is Russell Wilson’s reaction. Here’s a quote from his press conference on Tuesday (less than 48 hours after the game was over):

“I always kind of write down stuff and I wrote down this, ‘Let’s keep the focus on the future, not what’s behind.’  I think that’s a really, really important thought in terms of staying positive.  What can I do for the next opportunity that I have?  What can I learn?  Good or bad — if we had won the Super Bowl or if we had lost in the fashion that we had.  I would still be thinking the same way and I think keeping that consistent approach to life in general and this is a lot bigger than obviously, losing the game is tough but any life circumstance — losing my dad.  What do I do next?  How can I learn from the lessons of losing him?  And obviously losing a game is completely different than losing a family member. Those are the type of things that I think about.  That’s how I try to prepare my mind for the next opportunity that I have — the next thing that I have in my life that comes up.”

That’s an incredible quote, especially given the circumstances. He doesn’t throw his coaches under the bus. He doesn’t blame anything on his receiver (even though analysts say the receiver deserved a lot of the blame on that play). He looks at what he can learn and how he can apply it to future situations. I don’t know about you but when the Packers lost to the Seahawks a couple weeks ago (a game I wasn’t playing in, in case you were wondering), it took me a good ten days to even want to think about football again. And I’m just a fan! Wilson is already looking at what he can learn, less than 48 hours after what will surely be one of the biggest missed opportunities of his career. His capacity to handle adversity and learn from it has just left me in awe since reading that quote yesterday.

Dealing with adversity is something I’ve been trying to work on over the past few months. Packers game aside, one thing that’s been helpful is Stoicism. There’s probably a super technical definition of Stoicism online somewhere but essentially what it teaches is that we can’t control external events or the results of our actions. We can only control the actions we make and our reactions to external events. What this philosophical belief system results in is doing the best you can and then letting the chips fall as they may. There’s a lot more to it but that’s the gist. It’s been amazing in delivering peace of mind so far but clearly, I have a long way to go in my understanding and practice of Stoicism.

I have no idea if Russell Wilson considers himself Stoic or not but he’s been doing a great job of demonstrating the ideals over the past few days. His post-game reaction has shown me how much further I have to go in my ability to handle the ups and downs of my life, which are quite honestly nothing compared to what an NFL quarterback faces. And in turn, the pressure an NFL QB faces is fun and games (literally) compared to what someone living in poverty or under the rule of ISIS would face every single day. It’s all about perspective.

By the way, if you want to read more about Stoicism, definitely check out Meditations by Marcus Aurelius. If you read that and enjoy it, then pick up Letters From A Stoic by Seneca and The Discourses by Epictetus. And in case you thought all Stoics are ancient, some modern stoics include Bill Clinton, Arianna Huffington, and Ryan Holiday.

How Are Some People So Productive?

The thing that impresses me the most about successful people is the sheer volume and quality of their work. How can someone accomplish so much in the same 24 hour days that you and I have?

Who are some of these people I’m so impressed with? Well how about Ryan Holiday, who was simultaneously Marketing Director at American Apparel, blogging extensively, and writing high quality books. Or James Altucher, who has started multiple successful companies, ran a hedge fund, spilled his soul on his personal blog, wrote several of books, runs a very successful podcast, and is also an angel investor. Or my good friend Justin Mares, who simultaneously scaled Airbrake as Director of Revenue (which led to an acquisition by Rackspace) and co-wrote Traction (which I highly recommend by the way). People like Ryan, James, and Justin inspire me.

I try not to even think about the productivity required by Elon Musk, who is CEO of both Tesla Motors and SpaceX. He’s Iron Man though so I guess he doesn’t count.

So how are these people so productive? Here is what I’ve observed:

  1. Routine: Productive people have a routine that they use to get themselves in the zone. I’ll be writing a lot more about this in the future as it’s a personal interest of mine but for now let’s just say that getting “in the zone” is not random.
  2. Time Management: By this I don’t mean OCD behavior like scheduling every second of your day including bathroom breaks. I’m talking about avoiding the endless Facebook/Twitter/Yahoo/YouTube/Quora/Buzzfeed time waste loops. They seem like short breaks but end up taking 15-20 minutes each time and eat up huge chunks of your day.
  3. Inspired: Productive people simply don’t hate their work. In fact, it’s usually the opposite – they actually enjoy working on their craft.
  4. Student Mentality: All these people have a certain humility about them and in spite of their success, maintain a humble student attitude. They are always learning and more importantly are always open to learning.
  5. Gratitude: it seems counterintuitive but productivity requires being in a healthy state of mind, which means being thankful for your life while still striving for improvement. I’ve seen people I admire consistently practicing gratitude and adding gratitude to my morning routine earlier this year was the best thing I’ve ever done for my mental health.

Here’s some simple math: if someone has just 1 more hour of productivity per day than the average person, at the end of the year, they’ll have 365 hours of extra work. After 10 years, that’s 3650 extra hours. Over a 30 year career, they have a 10,950 hour advantage. According to Malcolm Gladwell’s book Outliers, 10,000 hours of practice is the key to mastery so based on the math, someone with an extra hour per day will be a master of 1 more skill than the average person. If that skill is something valuable – you can see why that makes a difference. I would make the argument that highly productive individuals actually have a 4-5 hour per day advantage over the average person, which would mean mastery of an additional skill happens in 6-8 years instead of 30. While I’m not a huge fan of Gladwell’s work and disagree on a few things, the conclusion is the same: the extra hours compound into a real advantage over time.

This is one of my favorite topics to learn more about so if you’ve observed any other techniques or use something yourself, definitely let me know in the comments or contact me directly.

Staying Mentally Stable On The Startup Rollercoaster

Lately, there’s been some much needed talk in the startup community about the mental health effects of the constant ups and downs that come with being involved in early stage companies. The toll can be especially taxing on founders – take a look at the notes Brad Feld received from founders after he wrote his illuminating “Founder Suicides” blog post earlier this month.

The media usually portrays famous founders as Supermen/Superwomen – which makes “regular” founders feel inferior and inadequate. This is very much related to the “crushing it” culture that has gotten so rampant. When founders are asked how things are going, it’s incredibly rare to hear an answer other than one of the many variations of “crushing it”. With more people like Brad Feld talking about mental health, I’m hoping that honesty will become more common, but maybe that’s wishful thinking.

Having been involved in a couple startups over the past few years, I’ve been through some awesome experiences and also through shitty, terrible things that I wouldn’t wish on my worst enemy. Staying mentally healthy in a rollercoaster environment like that is a huge challenge and to be honest, is something I’ve struggled with at various times in my life. Over the past few months, I’ve taken a more active approach to keeping a healthy mindset. Below are some scientifically untested techniques I’ve been using with success so far to keep my work problems in perspective:

 

Read Books:

I read a lot of books growing up but for some reason I pretty much stopped once I got to college. In 2014, I rediscovered my love for reading and it’s been great. Most importantly, I’ve found it’s a perfect escape for my overactive work brain. When I watch TV or a movie, my brain doesn’t have to do any work and continues drifting towards work. When I’m reading a book, my imagination gets involved and my brain stops thinking about work for awhile.

Stay Physically Healthy/Exercise/Go Outside:

When you’re already not in a great mental state and then something goes wrong physically, you’re just asking for disaster. Re-committing to my health after some issues in early 2014 has helped my mental game so much.

Going out into nature is really helpful to me as well. There’s something about being in nature that just gives perspective and makes problems feel insignificant.

Get a Hobby:

Doing something outside of work gives you two things:

  1. Your brain gets a break from thinking about the same problems – which actually helps you solve them.
  2. You make friends outside the startup bubble

I started taking acting lessons in April and it’s been great. I’ve met people who live in a completely different universe from the startup community, which is enlightening. It’s also given me insight on my own emotions and habits that I wasn’t previously aware of. I started this hobby so randomly: I took a four week Acting for Non-Actors class to improve my sales skills and ended up liking it so much that I started training more seriously. Most importantly, it lets me shut off the analytical part of my brain for awhile and do something different.

Stay Close With Your Family and Friends:

This is listed last but it’s by far the most important one for me. In most industries (including startup world), things work like this: when things are going well, you have a ton of people contacting you and it feels like you’re the most popular person ever. But when things are going badly, no one wants to talk and you feel like an outcast.

The good news is that relationships with your true friends and family don’t change when things are going great or when things are going terribly. They will be there for you. This is why it’s so important to not let your relationships die out of laziness or lack of time – something that happens too often. Friends and family are your mental safety net. When I’m having a crappy day, nothing cheers me up more than gchatting/texting/Snapchatting with friends or having a long phone conversation with my mom, dad, and brother. Invest time in your relationships and you’ll never feel alone.

 

Lastly, I just want to say that having struggled with some of these issues myself in the past, I’m always here if someone needs to talk or get things off their chest.