When to make Ugly Moves

Imagine you are a lizard.

Now get over the shock that you are a scaly skinned cold-blooded reptile who also owns a computer and can browse the internet.

Okay with that behind us, welcome to being a lizard. As a cute little lizard you will be spending the day making choices about where to walk and jump.

Having recently been embodied as a human with similar abilities this is likely a relatable position.

You’ll mostly be choosing to walk and jump in directions that you hope will reduce the distance between your mouth and tasty lizard food.

This is also likely relatable.

Occasionally though, you may have to decide if you want to sever your own tail from your body or not.

This is likely not a particularly relatable situation for a lizard who was once a human. Humans don’t have tails. We also can’t detach our extremities from our torsos. Ok we can but not particularly efficiently.

Why would a lizard ever want to do this?

Maybe in in act of teenage rebellion from its overbearing parents?

Maybe it’s more of a fashion statement?

Some kind of lizard self-service gender reassignment?

Allow me to pepper in some context…

See, lizards have this cool superpower where they can regenerate their tails if attacked by a predator.

This is not particularly helpful if you’re plucked from ground by your head in the case of the above.

But you know, there are only so many images of falcons eating lizards on Google so I had to compromise.

If a falcon had indeed caught you by the tail it might be in your best interest to say ‘adios’ to that appendage.

It buys you another day of life after all. Being alive is a perk of living. Another thing that we can all related to.

Okay, probably enough lizard talk.

When long-term thinking gets you killed

I’m a huge fan of long-term thinking. So is Jeff BezosWarren Buffet, and a 3rd rich person I’m too lazy to think of.

Most people know that long-term thinking is better than short-term thinking if you are trying to build wealth. The problem is not the awareness of this truth, but rather getting your behavior to reflect your understanding.

This post is not about why long-term thinking is good and why you are a total dumb dumb if you’re not doing it RIGHT NOW. This post is about when short term thinking actually IS better than long term thinking in the context of startups.

(By the way you are welcome to go back to being a human again while you read the rest of this.)

Startups = Lizards

Your stupid, tiny startup is a lot like that lizard that was snatched up by the falcon.

“The falcon” for startups is running out of both money & hope at the same time. That is the condition of startup failure.

In the long term, we are all dead. For lizards & startups that is sometimes equally true in the short term.

Tooltip: Short-term thinking makes sense when faced with immediate existential threats.

Does this seem obvious so far? It should, so that is good. But, it is amazing how frequently startup founders ignore or fail to recognize immediate existential threats.

There are a myriad of reasons this occurs.

1. Founder is over optimistic about an upcoming good thing that is totally, definitely happen.

A founder facing this type of ignorance is suffering from over-optimism. They are going to tell you thing like:

‘Everything will be fine right after this lead investor signs on to the deal.’


‘We are about to land this huge new enterprise customer, contract is almost signed.’

Any founder with experience is going to know that deals are not done until money is in the bank. A mentor of mine would add to that statement: ‘and moved three times.’

Founders are naturally definite optimists who like to move fast. We love counting unhatched chickens.

The problem is that the blind side is not protected. If you are sure Plan A is going to happen you will be destroyed swiftly once Plan A doesn’t work out. Or even work out in the timeline you projected for that matter.

Solutions: have backup plans for ensuring that you have enough cash. Earn more money than you spend. Don’t spend money on things before you need to. Oh, and have a real human accountant.

2. Founder is lying to themselves

The canonical example of this for me is faking product-market fit.

Founders know that this is a thing you need to have, because Y Combinator and Mark Andreessen say so.

So, they pick a metric that makes it look like they indeed are one of the select few startups that have iterated their way to PMF. After all it is easier to get funded if you’ve already got PMF. So, an easy way to increase funding chances (in theory) is to just move the PMF goalpost to where you are today.

Everything works in powerpoint.

Amazingly, these founders will be able to eloquently articulate the underlying root causes of their startup failure in their post-mortem Medium article. Too bad they didn’t think through those failure scenarios before the falcon had cialis 20 mg them dangling over some very hungry winged offspring.

Solution 1: start being paranoid and think about why your startup is going to fail all the time. This is called inversion and a rich guy name Charlie Munger is sort of obsessed with it.

Solution 2: Surround yourself with people who call you on your BS and give you honest feedback. Like that accountant from above.

3. Startup lacks urgent survival instinct

This is the well-funded VC startup failure scenario. If left unchecked, millions of dollars in a bank account can become terminal.

VC backed companies can operate without a sense of survival for months, sometimes years. For the survival brain this is akin to a 6 month ban on falcons in your area. What happens is you over-invest in scalability before force feeding reality into your business model.

This is like making the lizard forget it has the ability to save itself when the falcon grabs it by the tail.

Solution: bootstrap. The more practice you have staring death in the face the faster you will learn how to survive.

General lesson: Be prepared to make ugly moves

So short-term thinking is good now? Does Wall St. have it right after all?

Well no.

Short-term thinking is still not advised. But the reality is that sometimes the right thing to do is to make a downright ugly move.

Leaders that navigate startups to sustainable places know when to stop thinking long-term and to start making ugly moves in key moments.

Moves like:

Ben Horowitz calls ‘ugly moves’ Wartime CEO mode BTW. You can read an entire book of his ugly moves here.

Think long-term again after the chaos

Ok so sometimes you’ll have to cut off your startup’s tail to stay alive. You’ll be fearful to do so, and once you do it you’ll congratulate yourself for a job well done.

But snatching a stalemate from the jaws of defeat is not an opportunity to pop champagne. It’s a time for leadership and long-term thinking.

You’re going to have to invest additional energy, attention, and resources in rebuilding the culture and mindset of long-term thinking in your company.

You’ll need to be clear with your team about why you made an ugly move and reaffirm that it was not ideal. You lead a 5 why’s analysis to eliminate the conditions that created the circumstance. You should find more accountability partners and seek more negative feedback.

These are the yeomen activities that successful long-term thinkers perform in the aftermath of an ugly move.

It’s how you make that ugly move a mere blip on a timeline that eventually leads to a sustainable and profitable company.

Mixing passion with income could be a mistake

A cautionary tale about the Skateboarder Paradox

Once upon a time I had a roommate who loved skateboarding.

Let’s call him Travis.

Travis lived for the weekends. The reason?

To skateboard.

His work life? That was just something that got in the way of skateboarding.

Each weekday he commuted into work and plopped down at a dusty cubicle. For eight hours a day his eyes would burn into the shapes of spreadsheet cells. His mouth persistently stained with the taste of cheap coffee. It was….soul crushing.

He’d usually trudge home around 7pm. By then it was too dark to do much skateboarding.

He was too tired anyway.

When the weekend arrived Travis’ energy levels always skyrocketed. He’d kickstart any given Saturday by rallying his skateboarder friends via group text.

They’d rendezvous somewhere in the city and spend the day perfecting new tricks, talking shop, and uncovering unexplored terrain.

This was what Travis lived for. He wished he could do it all the time.


One particular Saturday Travis found himself in the mall buying new shoes.

While waiting for the dude to come back with a size 11 to try, he gazed up at the Vans logo above the racks of shiny shoes.

It in that moment an idea hit him like a sack of bricks:

‘Why not start my own skateboard company?’

Everything suddenly snapped into focus. It felt like his entire life had been leading up to that single idea.

He could merge his passion with his income!

The next day he quit that soul-crushing job in a huff of confidence. A ‘last day of school’ feeling washed over him as he raced out of that Godforsaken parking lot for the very last time.

He was free.

The next day he Legalzoomed his way to a Delaware S Corp: Skateboard, Inc. He came across a small business lender willing to wire him $30k to get things rolling. He signed a 2 year lease on a warehouse to store his products. He set up a Squarespace eCommerce site.

Two weeks later he sold his first skateboard. It was coming together.

Of course, there was an overwhelming amount of work ahead to get the business to breakeven. Months whizzed by as if they were days. His sole focus in life was to make the business work.

By month 6 something felt wrong.

He noticed that he’d actually been skateboarding a lot less these days. Why?

Well, he needed to maintain inventory of course. That required hours upon hours of staring into spreadsheet cells. He had to handle customer service too. He also had to log all his crumpled receipts into Quickbooks with an app that sorta worked.

There was ‘always something’ that got in the way of skateboarding. His friends began to realize this and stopped including him in their group texts.

One day he was aimlessly staring up at the Skateboard, Inc. logo above his boxes of inventory.

It was in that moment that a difficult thought hit him like a sack of bricks.

‘I’m not happy anymore.’

This realization sent Travis into a tailspin. It felt like he’d spent all those 80 hour weeks building himself a prison. Instead of one soul destroying job it now felt like he had five of them.

Sure the spreadsheets were about skateboards. The phone calls were aboutskateboards. The bills were about skateboards.

But Travis’ life was not about skateboarding. It was about keeping Skateboard, Inc. above breakeven.

Eventually Travis had enough. He shut down Skateboard, Inc. and got a job at that Vans store in the mall. Missing out on skateboarding was simply not worth it anymore.

The Skateboarder Paradox

The Skateboarder Paradox is the simple idea that tethering your income to your passion will fundamentally change how you practice that passion.

Don’t let internet marketing bloggers trick you, ‘entrepreneurship’ is not the only way to do what you love. They are biased because their identity is too wrapped up in the notion to give unbiased advice.

The truth is that creating a business is merely one option on a vast spectrum of ways to practice what you love. Infrequently is it actually the best option.

Doing what you love as an employee in an existing company is a perfectly wonderful and valid lifestyle. Maintaining a separation between passion & income might be making you happier than you have context to realize. It affords you the freedom to perform your passions authentically without the burden of breakeven distorting your choices.

Skateboarder Paradox is something to consider before making the plunge into business ownership.

The grass could very well be greener right where you are.

The communication habit you’re missing

Saying hard things to people that matter

Once upon a time Seneca said:

We suffer more in imagination than reality.’ — Seneca

He’s dead on. Especially when it comes to having hard conversations with people that matter in life.

Many people would rather consume themselves with fear than have a hard conversation. Super sensible right?

But why are we so fearful of bringing up tough topics?

It’s because Mr. Tribal Brain is kicking in. He does not want you to stand out as a disagreeable member of your community. That is tantamount to suicide if living with 20 other people in an isolated village 8,000 years ago.

But today that’s no longer a useful biological impulse. Overcoming this evolutionary handicap will make your life better. You’ll be able to say things like:

‘I didn’t like the way you just looked at me, it made me uncomfortable.’

‘I find it hard to justify continuing to invest in our friendship after what has happened.’

‘When you walk out the door without saying ‘bye’ it makes me feel unappreciated and small.’

Those things should be as easy to say as:

‘Bro, wanna go see Wonder Woman’?

‘Can you pass the Sriracha?’

‘Vampire Weekend made me a Horchata lover.’

This post is your first step in getting there. It is going to give you two useful strategies along with three action items to start initiating hard conversations.

Strategy 1: Filter irrational people from your life.

Hard conversations are useless if you’re having them with irrational people who don’t listen. If your conversational counterpoint possesses these traits they will not:

  • Hear or accept your feedback
  • Make any changes as a result of your feedback

Trying to use hard conversations to improve relationships with irrational people is not a good use of time. The better approach is to just filter those people out of your life altogether. They aren’t worth it.

This process of filtering will be easy if you perfect strategy 2.

Strategy 2: Mint a hard conversation habit

Everyone feels the same thing when they aren’t saying what they wish they could. I’d characterize it as the feeling of dissonance.

It’s what wells up in your nerves after you hold feelings inside and don’t let them out.

For me it feels like what my body does while sitting in a dentist chair. I try to stay relaxed while they are pricking away at my ill-flossed gums. But still, I’ll find my legs and toes tensing up constantly. I’ll try to focus on releasing that tension but once I go back to thinking about something else it returns.

The feeling that a hard conversation should happen can feel the same. In those moments we have a choice — to suppress (and thus keep suffering inside our imagination) or say what we need to say (improve our reality).

In order to say more than you suppress you need to learn how to use the dissonance feeling as a trigger for habitual action.

In the short term you’ll need to put on your willpower pants to get this done.

That’s because willpower is the activation energy needed to perform a non-habitual action. But while some amount of willpower is needed you can minimize the amount required by planting cues into your environment that remind your experiencing self what your narrator self wants to do.

An easy way to do that is to create a recurring reminder in an app you see daily that says:

‘Say what I’m feeling the moment I feel it today.’

You’ll whiff a lot at first, but once and a while you’ll be able to pass instructions to your experiencing self to actually say the hard thing in the moment it should be said.

If you’ve followed Strategy 1 and surrounded yourself with rational people you will gain great results.

These results will create a positive feedback loop encouraging you to saymore often. Continued positive experiences with this will change the say / suppress probability curve in a compounding fashion.

With each instance you’ll need less willpower to choose to say. Eventually willpower will be unnecessary and the habit will calcify.

Years later you will find yourself tranquilly sitting on your porch sipping horchata.

Suddenly you will be struck with the memory that you used to totally suck at hard conversations. You’ll be stunned that you blunderbussed your way through life for so long without this skill.

Do these things right now

Instead of clicking on the next tab in your Chrome Centipede, make the last few minutes of reading this stupid article worth it by doing three things:

  1. Make that recurring daily reminder in your app of choice encouraging you to say hard things.
  2. Save this article somewhere and reread it in a week to reinforce the concepts.
  3. Fill out this self-quiz I made based of the ideas in the book Crucial Conversations. It’s a great place to start if you don’t know how to find the right words to start a hard conversation.

Good luck — this stuff is not hard. You just have to actually apply the idea in your life to experience any benefits.

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Dear Noise

Leave me the hell alone please.

You’re the buzz in my pocket. You’re the errant LinkedIn request. You’re the little red push notification. You’re the embodied entirety of Twitter. You’re the thing that breaks my flowstate. The blimp on the map that throws me off the journey.

I hate what you are. Worse, I hate what you’ve made me become. I can’t resist you. I’ve allowed you into my life for so long that my brain is wired to crave you. You’ve physically altered me, one *BZZZZZ* at a time. You are a cute little attention tapeworm that is killing me slowly. You divert my attention away from what I want to be doing and shove my face into an ever-updated shiny object of perpetual distraction.

Noise — I recognize deep down that it is not your fault. You are just following orders. You do indeed have a designer, a God of Noise that has brought you into this world. That God is an SF-based product manager with a flannel mustache and one sole mission: to pluck out my eyeballs and trap them in a fancy mason jar on his Herman Miller desk. Your designer does not want my life to be good. He wants to sharecrop my attention, and he is going to use every magic trick he has to ensure he gets it.

For years I didn’t realize you were such a problem. I thought you were helping me connect and engage in the world in an all new way. But now I know that you are a big black spot that’s holding me back from really living.

Right now, the average time to distraction across our population is seven minutes. And we as humans have you, The Noise, to blame. You bring out the worst in us, you make us weak, unfocused, and trivial. Did you know that it takes us about 15 minutes of deep thought before we can really immerse ourselves into a problem? How do you expect us to create anything great if you break our concentration every seven minutes?

Dear Noise — you’re existence essentially ensures that most humans will never produce a real breakthrough or insight of any substance. You are relegating the burden of human progress to the outskirts of society. To the weirdos who don’t carry smartphones, who reject social networks, and who escape you at every possible turn.

For the last six months I’ve done my best to join the ranks of these ostracized psychopaths. I’ve deleted Facebook & Instagram, blocked out ads and feeds, and turned off push notifications. I’ve done my best to bury you. But still I cannot consistently outrun you. Noise, you continue to insidiously penetrate my existence. The Signal of what I want to do in life is often invisible against the background radiation of your insipid social graph.

But Noise — let me be loud and clear. I will break out of your cage. I’m at war with you, and plan to either win or die. My attention and my time are all that I have, you are not permitted to leech my most precious resources from me forever.

Noise, consider yourself on notice. And if your designer happens to find this letter, I have a final word of advice for him as well:

Dear designer of attention based systems, you have a choice. On one hand, you can keep vampirically draining humanity’s willpower under the guise of capitalism. Or, you could use your unique talents to vaporize this vast fog of Noise that clogs the arteries of the human superorganism. You could design systems that maximize focus, prolong linear thought, and make us more capable of dedicating attention to hard problems. Heck, maybe you could even….

….sorry, just read the most hilarious Buzzfeed article. What was I saying?

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How to grow in the right direction

We’re about to hit Thanksgiving, which for many of us means heading home to see family. Inevitably, that means we are going to run into little cousins, nieces and nephews we’ve not seen in a while.

They always seem to grow so fast. But that’s only true from your frame of reference. To the parents and teachers embedded in the lives of these little ones development comes at a snail’s pace.

It’s this phenomenon that reminds me to consider my own development as a person and system’s builder through a long term lens.

This post is about how to build a reference frame to determine if you’re growing and developing in the right direction.

History moves non-linearly

If I look at my own development and progress over the last ten months I can easily get frustrated with myself. I could have worked so much faster. I could have used much less money. I could have / I should have / If only…

But histories of both people and societies don’t move in nice upward sloping lines. Sometimes we go backward to go forward. Sometimes we miss modules on the cumulative test of living life.

I’ve learned an incredible amount by throwing myself into the weeds of business building with no functional idea how to make companies. I’ve learned much more just doing it first hand than I would have by jumping into an MBA program.

Yes, mistakes have been made that I would not have made in the comfort of university program or ensconced in business books exclusively.

But now after a few years of having no idea what I’m doing I’m staring to figure it all out.

I’m starting to get a sense of not just what I want to do in life, but how I want to do it. And luckily, I’m now cooking with gas at a young enough age to have real impact over time.

The road ahead is free. No debt, minimal personal responsibilities, and a huge mission to tackle with an epic roadmap. That’s really not too bad.

Every day you work down the same path you benefit from compound interest. You are able to build on what you did the day before. Deviation from the path should be no more than the occasional toe tip into unfamiliar waters.

Hindsight rationalization

We look back on history and surmise that the story of western society is one of many narrow escapes from certain death. For example, American’s could never fathom a future in which we lost the American Revolution.

But had we lost and stayed English we’d all be looking back on that war relieved that we thwarted the drunken colonists from messing up our empire.

We perform this same rationalization jiujitsu with our lives.

You’re life is building intertia towards some end point. It will do that whether you control it or not. All decisions make us a slightly different person. That is evolution, this is inevitable.

If you play a lot of basketball, you will improve. You will make friends that like basketball. You will perhaps earn a basketball scholarship. You may even be drafted.

If basketball is what you want to truly do with your life draft day will be a time for celebration. But what if you just passively opted into basketball because you were pretty good at it and your friends did it? Small choices become big life swings often without us noticing.

We always want to look back on key moments and say ‘that was the best thing that happened to me.’ Especially when we reflect on adversity. We pluck out silver linings to concoct a story that trends up and to the right.

But maybe getting drafted will be the worst thing that ever happens to you. Maybe it will be like the English winning the revolution from the reference frame of a colonist. Maybe it will be the wrong team. Maybe it will be the wrong sport. Or maybe you really should have been a nose and throat doctor in Singapore.

How can you know?

Without a reference frame nothing is good or bad, everything just is. That’s nihilism. Nihilists are not useful to others. Don’t be a nihilist.

You need to establish a baseline reference frame through which you can filter events. For me this was developed through introspection into the things I did as a kid before I was heavily influenced by the thoughts of others.

When I was a kid I was a quiet kid in the corner that sat in his room and worked on legos, model rockets, and inventions. Sometimes I would pop out of my little universe and try to sell my ideas to the world.

Today those initial natural inclinations translate into three industries I’ll probably be involved with most of my life. Education, manufacturing, and sustainable energy. Those have been threads of all the projects I ventured into out of curiosity rather than command.

You become your choices

If you don’t have confidence that your efforts are adding up to something you’ll be proud of, what are you working so hard for?

Without intrinsic vectors you’ll optimize not for interest and curiosity but rather for money and status.

Instead of being rewarded by learning something or crossing a milestone of development in the spheres of interest, you’ll fill up your life with material possessions and redundant social interactions.

Your 8 year old self already knows who you should be when you grow up.


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Jump off the problem solving treadmill

The life of a startup founder is unglamorous.

My day is mostly filled with the fixing of issues. Cool stuff like discussing strategy, closing major deals, & designing products are a pretty low percentage of actual time expended.

Issues that fill days include:

  • Tracking down pieces of paper the government requires of me
  • Getting customers to actually pay invoices
  • Taking out trash cans and cleaning dishes at office
  • Editing documents and emails for typos
  • Negotiating with vendors
  • Polishing minor product minutia
  • ‘Setting up a time to connect on a call next week…’

You get the idea.

It’s not always fun, but these are the basics needed to create anything real in the physical universe.

Sure when your company grows up you’ll have other people to do a lot of the little stuff. But when you’re small everyone chips in on whatever is needed.

This issue solving treadmill is especially pervasive for people managers. As a manager one of your most important functions is to solve issues standing in the way of others. I envision this process a bit like being one of those sweepers in curling.

You’re out in front making it easier for your people to do great work

You want to evaporate the nonsense in the way of your colleagues so they can be maximally effective. This often means you’re running on many problem solving treadmills in parallel as a founder.

But issue fixing is not even just for managers. Everyone and everything in a company is built around solving issues.

You’re fixing issues for your team. Your team is solving issues with your product. Your product is solving issues for customers. If you’re B2B your customers are solving issues for their customers…

But here’s the thing:

Life is just not an endless problem solving treadmill.

News flash: there are worthwhile things in life outside of work (even passionate work). Spending time with good people, experiencing culture, and expressing new forms of creativity all come to mind.

In fact the whole point of most products is to make those other things easier to do or at least to free up time in other areas so those things can be done more often.

So the time you invest in work carries very high opportunity costs.

Thus, you better be solving issues for a meaningful purpose. I’m fortunate to have found what that means for me.

The subtle practicality of purpose

Beyond the squishy philosophy of purpose there is a simple practical reason to have one for your team.

It is really damn hard to get people excited about boring things.

Anything important is going to be rife with issues that need solving. Especially if that thing is new. To solve issues you need problem solvers. Just like you, the time they spend with you comes at high opportunity cost.

If the vision you have for them is not exciting, it is not particularly logical for them to cancel weekend plans and work longer hours to stay on the issue solving treadmill.

I turned 25 today.

Birthdays are reminders of how precious time is. This one in particular is a bit frightening because I find it absurd 2007 was actually ten years ago.

Obviously we all just slipped into a wormhole right after Graduationdropped. Or ok fine, maybe I’m just getting a bit older like everyone else.

Either way, I’m not spending the next 25 years solving issues for the sake of solving issues.

I’m learning that harmony between passionate work, enriching experiences, and time with good people is a beautiful life. A much better reality than living exclusively on the issue solving treadmill.

The ask here for you is a simple one: look up from time to time my fellow problem solver. Ask yourself why you are on that treadmill today.

It could be time to hop off for a while and find tranquility and meaning elsewhere.

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You ≠ Your Startup

This is the type of post I wish someone shared with me two years ago.

In corporate America I was a number. Make no mistake — you are too.

The truth of corporate life is that your worth to the company is 100% tied to your usefulness. Somewhere a manager has you as an expense in an excel spreadsheet. If you can’t be justified you can’t be kept, no matter how clever your water-cooler humor may be.

Corporations are the destinations degrees are designed for. In academia though your still a number — you’re tuition with legs while walking to the dining hall or lounging on the quad.

This is not a moral claim against these organizations. Still though, it makes sense that young people view startups as alluring escapes from feeling like a mere bead in an abacus.

We assume that the grass (and money) is plenty greener on the startup side of the fence.

As a founder of a startup you’re clearly no longer a number — you’ll be a person with a company! Your email signature will likely command respect. People will naturally invite you to speak at gatherings. You will be fawned over in the media. Investors will shower you with money because you ‘understand millennials’.

Everyone will reinforce the notion that you’re on an incredibly majestic Hero’s Journey into Unicorndom.

This will certainly feel better than being a number in an org chart, right?

Welcome to the Echochamber

For most first-time founders the transition transpires differently. Instead of working for themselves and building something meaningful, they end up working for the Echochamer.

The Echochamber is the collection of investors and accelerators who demand that you eat, sleep, and breathe your company at the expense of life.

It’s the startup press who will fudge realism for page views.

It’s the service provider emailing you after reading an article about your last fundraise.

It’s the ‘mentor’ who siphons equity and ego fixes for warm intros to nowhere.

The Echochamer takes down the clocks and strings up flashing lights on the walls of the startup casino. It will keep you attending events, reading its articles, taking coffee meetings, and shelling out cash4coworking.

You’ll keep doing it though because your life does not matter until you’re finally running an (unprofitable) unicorn.

The lesson for you is to not give in to the frothy hype of the Echochamber. Open your eyes to the implicitly self-interested relationships you will engage in while making a startup. Take advantage of opportunities that will benefit you but don’t let them take advantage of you.

If you give into the flashing lights you’ll find yourself gambling away your twenties building a startup that should have been a tweet.

And sure this is easy enough advice to give, but you won’t implement it unless you solidify one critical mindset change.

You are not your startup

The Echochamer is designed to reinforce the notion that your self-worth is tightly coupled with how well your startup is doing on that particular day.

This is how it keeps existing. The first step in avoiding the Siren calls of the Echochamer is to sever any relationship between your self-worth and the financial outcomes of your startup.

That’s the lynchpin upon which mentally healthy founders can build lasting and powerful companies without suffering through self-imposed sabotages.

A failure to decouple the two will shred your P&L as swiftly as it lays waste to your mental health. You’ll be too defensive and retaliatory to agnostically look at what is working and what is not in your business in order to make it better. You won’t put your work in positions where it will be judged by critics. You’ll exist in an endless stealth mode. You’ll always be ‘crushing it’ until the day you’re not.

Soon after everyone stops inviting you to events and tweetstorming about your now broken company you’ll be left with nothing but a ragged mental landscape and some worthless common stock to show for it all.

My wish for the young & naive founder is simple: decouple your self-worth from the success (or failure) of your startup. Both your work and health will be better off as a result of the schism.

The ‘Add an S’ Heuristic. (Last Mover Advantage)

My Mom has an incredibly vast vocabulary.

I love doing things with my Mom.

Naturally, these collisions of interest led us both to the game of Scrabble. As a kid, I’d find moments to fit in games, usually a matchup of titans that also included my younger brother.

My Mom would always play very unique, impressive words with solid point values. Quorum comes to mind. Her words would often draw ‘oohs’ and ‘ahs’ from my brother and me for their creativity. Her strategy was to win through sheer mastery of the English language.

I had a different approach.

There was only one letter that I wanted to find after reaching into that noisy pile of little wood tiles: the S.

I’d stockpile these nuclear weapons in my war-chest and wait for just the right spot in the board to appear. Maybe Mom placed Quorum right before a triple word, which just so happened to line up with the tail end of my brothers Zit.

My fingers quivered with anticipation the moment before I’d expose the dream killer.

I’d swiftly slam down the single point SI’d confidently relay the number to my brother, our official game accountant so that he could add it to the overall tally.

‘That one is worth 81.”

My deflated counterpoints demanded we consult the Scrabble Elders to assess the legality of this seemingly unjust manipulation. Too late.

To them this was unfair leapfrogging. To me, it was art.

Don’t build the board, fill gaps.

Some of the most successful technology companies have won using this ‘Add an S’ heuristic. For example:

Airbnb ‘S-ed’  Couchsurfing.

Facebook ‘S-ed’  Friendster.

Google ‘S-ed’  AltaVista.

Startups are not built to spend all their cash on customer education. They are supposed to spend it on customer acquisition. These two are easily conflated yet they are definitely not the same thing. For example, TiVo was a $200m customer education exercise that paved the way for millions of knockoff Time Warner DVRs to acquire all their (now wonderfully educated) customers.

I’m not arguing here that customer education is inherently evil. What I’m saying is that education is a strategy designed to eventually transition money from your customer’s wallet into yours (not someone else’s).

If you sell a product before anyone deeply feels the unmet need it solves, you’re unfortunately going to be spending a boatload of money making them feel said need. You’re going to be building the whole Scrabble board from scratch.

If you find that it is going to take too much time and money to incept your customers into acquiring a taste for your product, modify your offering.

In all likelihood someone bigger is waiting for you to do their R & D for them on your dime. Sure, if you move fast enough maybe they’ll acquire you instead, but ‘let’s cross our fingers and hope we get bought’ is not a strategy.

Instead, scale as if you need to become an actually functional business with a clear path to market saturation independent of acquisition scenarios. You can’t do that if you are spending all your time on heavy-handed customer education in the market you think you want in lieu of acquiring customers in a market that already want the thing you can make.

Uncover that stagnant industry that has not been Warby Parker-fied. Reconfigure an asset class that has not been Uberized. Attack that bloated sector that has not been SpaceX’d. Ask yourself what are the cleverest ways to solve an existing need 10x better on a dimension customers will still care about 10 years from now.

Find your gap, build your game piece, and look for opportunities to Add an S.

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Everything is temporary

How to accept death and create remarkable things

Think of the most formidable, permanent thing you can possibly imagine. Perhaps you conjured images of a large stone building? The brand Coca-Cola? The universe itself?

Welp, buildings are physical objects that are subject to both forces of nature and flippant predilections of grubby real estate developers. Brands die when all the people that experienced them do. Even the universe will eventually become a cold dead place devoid of all energy and life.

This post is about why accepting and embracing death is the best thing a creative person can do to boost their happiness and build a more enriching life.

So, the other week I built a sandcastle at the beach with some good friends (because I am an 8 year old and I love making sandcastles). We intentionally built it near the edge of the incoming tides, to create a bit of a plotline for our activity. The goal was to use our creativity and engineering prowess to make the castle stand up against the tides for as long as possible.

First, we erected the castle itself. Then, we toiled away creating a healthy wall around our small castle, complete with an elaborate moat system designed to wick away water. It was a pretty fun experience, and since I’m writing a heady Medium post about it there is clearly an insight here worth expressing.

Eventually we grew tired of throwing good sand atop bad, as the waves eroded more and more of our efforts at an ever faster clip. The Board of Directors of Sandcastle Inc. thereby elected to leave the castle to fend for itself against the big scary Atlantic. As our sagging monolith slowly succumbed to the waves, we strolled over to the boardwalk to drink really cheap beer and watch the lemmings play Pokemon Go.

Within 20 minutes or so, that castle was totally washed away. At that point it became impossible for anyone to ever know that there ever was a quaint little sandcastle there. No one else will ever know how long it lived, why it was made, or the names of the people who made it. That group of friends and I can certainly think back and recall that we made this castle, but eventually even this collective memory will be imperfectly recalled, transmogrify, and fade away.

Speaking of cheap beer, about four months ago I was at a friend’s house party. There were about 20 humans there, and one of those humans was the angsty younger sister of said friend’s roommate. That sister had brought her ‘rock band’ to this party, and they were playing some ‘music’ in the main room of the house for the ‘enjoyment’ of the partygoers.

I can honestly say that this was by far the most unpleasant auditory stimulus that I’ve encountered in recent memory. The shrills of her Squire Stratocaster and chalkboard exploding vocals made the fragile hairs of my basilar membranes commit group seppuku. It was really quite dreadful.

So naturally, building a bonfire outback was quickly latched onto as the only plausible means of salvaging this party. The only problem was that no one really wanted to make the fire itself, they just wanted to enjoy it once it was burning.

I freaking love making fires. So I put down my cheap beer and started collecting some sticks n’ twigs from the nearby wooded areas. Someone scrounged up a Duraflame, and we arranged our kindling into a careful conic structure around it. This tidy assembly was clumsily lit with a Bic by our host. It took a little while for the flames to pick up, but after about ten minutes we had a pretty large fire rolling at the nexus of the 8 or 9 appreciative bodies circumscribing this new heat source.

As the other attendees slid back into their various conversations, I noticed that the consumption rate of the firewood was outpacing the rate at which firewood was being collected (which was a whopping 0 sticks/minute).

To remedy this situation, I broke off from the Donald Trump theme song brainstorm sesh that was engrossing the conversation to go fetch additional wood. I personally kept that fire roaring for a good thirty minutes in relative anonymity, until I made the conscious decision to stop fueling it and watch it die out. As the fire proceeded to slowly ebb into embers, I felt a deep (and weird) connectedness to this simple little fire in the middle of this mediocre party.

The lifecycle of all projects

These are two stories about the only thing that is certain in life: entropy will always win.

All the projects you are working on right now are just like that sandcastle and that bonfire. All projects are defined by a value function, where the perceived value of the resources put into a successful project have a lower perceived value than that project’s output. We creators input work to make this function positive. The total net value created by your project is the integral of this function.

Each value function has three main phases: value creation, steady state value production, and value decay. The function can be graphed sort of like this:

A semi-labeled graph of the value function over time.

1. Value Creation Phase

This is the messy front end. It is when the innovator or creator is most critical to the process, and it is when the overall risk of failure is highest. Here you are learning what your project is, inventing value it creates, how it will grow, etc. For example, if your project is a painting, this is the part where you are actually laying down paint on canvas. Almost all books and articles you will ever read about the creative process are talking about what to do in this phase.

2. Steady State Phase

Once a project exists, it enters the Steady State Phase. During this phase the project does not significantly change shape, and is supported at its peak value level by a Maintainer. Sometimes that is the same person as the creator, sometimes it is not (like the case of startup founders being replaced by professional CEOs). This is the phase where the system is actually most valuable to other people, and where the opportunity exists for the creator to capture a percentage of that value for themselves if they so choose.

For a painting, this is the time it spends sitting in the gallery for the world to enjoy, and for the curators and guards to keep safe and maintained. The creator often finds this part of the lifecycle insipidly uninteresting.

3. Decay Phase

The final phase of any project is the Decay Phase. This is when the value function driving the incentives to maintain the project break down. This is the natural end state of all projects, including our sandcastle and bonfire. For a painting, this would be the moment it is discarded, or the time when it sits in the curator’s warehouse collecting mold and dust.

Often, projects hit this phase when the resources required to maintain the project begin to seem more valuable than the project’s output. An example of this is a legacy codebase that is more expensive to maintain than the price of a proposal to build a new system to replace it.

If the opportunity cost of maintaining a project is too high, a rational creator will do one of two things.

Decay phase case 1: If the project can keep existing without maintenance for some period of time, the creator can just forget about it. For example, NASA does this with old satellites all the time. Once a satellite is no longer useful, it’s common to simply allow it to slowly orbit closer and closer to Earth until it eventually falls into the atmosphere and burns up. The satellite may still capture a bit more useful data during this type of decay phase, perhaps even at a high return on asset ratio since no resources are going into maintenance here. Regardless, any data collected during this phase is seen by NASA as gravy. The satellite is on its way to death.

Decay phase case 2: Sometimes it is not possible to let a project die a slow death. Usually in cases like these, the project is monopolizing resources at a very high opportunity cost. Perhaps you are using a CPU in your closet for Bitcoin mining, but you want to instead use that same CPU as a rendering farm for a major new client you landed. You need that expensive CPU to do the work, so you have to kill your mining project in order to employ it.

When the opportunity cost of keeping a given project alive is high, you must transition from a Maintainer to an Executioner. This is a healthy thing that frees up your resources to be utilized more fully. There is nothing wrong with killing projects.

But the one role that you should never take on is that of the Embalmer. Once a project’s value function no longer yields a net positive number, that project should not continue to be preserved. Creators that preserve projects in the name of residual nostalgia (‘we’ve always done it this way’) will always regret (or pay for) their decision.

This is not just true for projects

This very same value function applies in relationships (platonic and otherwise), though we have a much harder time accepting this truth.

A relationship is an interaction force between two people that is designed to enrich the lives of both creators. The first phase of a relationship’s creation is an exciting phase of mystery, discovery, and novel new experiences. The subsequent maintenance phase is characterized by consistent bidirectional enrichment and shared memory making. The dawn of Decay Phase is marked by a corruption of the relationship’s underlying value function. Once the enrichment emanating from the interaction becomes mono-directional (one person gets a lot more out of it than the other), too infrequent, or totally nonexistent, the decay has begun to snowball.

Sure, not all relationships must decay, a few rare friendships and marriages really do last entire lifetimes in a high output maintenance phase. But I think the more common case (judging by divorce rates and personal experience) is that most relationships enter Decay Phase long before the death of the people involved in those relationships.

Absurdly, we almost always become Embalmers of our relationships instead of Executioners despite this fact. We prop relationships up and repeatedly bail them out, sacrificing additional precious resources to harvest ever diminishing dividends. We throw good time after bad. We choose to pump wishful thinking into relationships to keep them alive, instead of killing them or letting them wind down to free up resources that can then be deployed to grow new relationships that produce net positive value functions.

We do this because making new things grow is risky, hard, and scary. Using personal energy to hack authentic human interactions out of daily noise is often exhausting. It can feel like we are embodying the story of Sisyphus pushing his rock up that hill. So instead, we sit in a tepid pool of decaying projects, jobs, relationships, and beliefs for years until we inevitably die. This is pure madness (and the reality of the modern American suburb).

What to do instead?

The failure point of human happiness is this rampant inability to kill systems operating in the Decay Phase. We are all afraid to pull the trigger. We envision the void that we’d be left with in the wake of such a move and we grow weak and afraid. We’d rather have a so-so sure thing over the possibility of a truly great thing.

If you take one thing away from this post, know this: the void of emptiness is all there really is. It is the white canvas upon which everything in life is built. It is infinite potential energy, waiting to be organized by you, the creator of your own life.

If you ever want to be authentically happy with the experience of living your life, you must first be comfortable in this infinite void of nothingness. You must be able to comfortably exist in the absence of meaning, of human interaction, of joy, of success. You must be able to stand tall in the abyss without shutting down your mind. You must be able to observe faint little ripples in that void which could just maybe become real structures. You must be willing to invest time in turning ripples into structures. You must go forge a ‘meaning of my life’ structure, a family structure, a career structure.

You can build structures that will yield warmth and satisfaction and enrichment. You can maintain them for as long as they produce those things. And then you will end or let go of the ones that stop producing joy. You will let that sand sift back into the void to be repurposed into something new.

You keep going until you yourself fade away into the black sand of the universe. Back into the raw constituents of stars and planets from which you first emerged. You fade away in order to make room for the next spry creator to build their own little sandcastles atop their respective voids. They too will fade to the next one day.

Those future creators won’t know anything about the beautifully fragile castles you constructed. They won’t feel the calming warmth of the bonfires you maintained.

But the same grains of sand that ran through your fingers will run through theirs. They will make beauty from nothing just as you did. And no matter how fearful of the void you may be now, remember that you aren’t the first to fear it. The creators that came before you whose sandcastles you can’t ever see and whose fires you can’t ever feel experienced that very same fear.

You are alive now. You will die soon. You are temporary, so be it. Now go sculpt something remarkable from your void, because that is what we do.

Most startups should be tweets

As a creator, you should always aim to nudge the ideas you feel are valuable to others out into the world. This is the art of idea deployment. To do this well, you as the creator have to think carefully about which reality deployment channel your idea best fits into.

Would it be best presented as a scientific paper? A painting? A blog? A conversation? Perhaps the idea should manifest as a physical object. Maybe a diagram, or just a post on social media.

On very rare occasions, it may become apparent that the idea you’ve discovered can only be brought to life if a lot of smart people work really really hard on it for several years. This idea can’t be made truly real in a blog post alone.

That’s when you have to create an organization of people that also want this particular idea to exist in reality. That is when you create a startup. That’s the ONLY time you create a startup.

But right now, deep in the echo-chamber of startup-y madness land, a frightening thing is happening that’s worth calling attention to. Simply put, people are wasting their lives working on ‘startups’ that are better off as mere tweetsThey are all choosing the wrong channel to deploy their ideas.

Each top ten startup city is filling up with founder-clones building the next B2B VR drone AI bitcoin disruptor. They’re doing it because having a startup is great for their personal brand. Or because they see it as a way to earn fame. Even more likely, they don’t know why they’re doing it. They’re ‘why-less.’

Beyond the redundancy of ideas in the echo-chamber, most new ideas are incredibly thin. While it’s extremely helpful to be able to communicate a complex roadmap in a blog post, don’t mistake a trite blogpost for the roadmap itself. Startup ideas must go deep, down to core human drivers and raw economic arguments. They must stand up to ruthlessly candid feedback. They must include a non-BS reason that you’re one of the few people in the world that should be working on that problem.

A competitive advantage is not a clever sentence you toss in a slide deck the night before a pitch. A competitive advantage is a unique worldview only attainable through the past experiences you’ve had. A startup worthy of all your time and attention should be the crescendo of long bubbling social observation and excruciating self-awareness. The nature of a startup is hardcoded into it by the natural inclinations of the founder.

The requisite nuance and insight that produces great startups can’t fit in a tweet. You can certainly tell us what you’re working on in 140 characters, but that should be merely the first layer of a deep dive down into the deltas you see between actual reality and the way you want it to work.

So the next time you read a TechCrunch article and are met with a burst of inspiration to move to SF and reinvent the way the on-demand Pastrami economy operates, ask yourself if it’s really worth nuking 10 years of life in service of the idea. It may be wiser to pop off a quick tweet about the idea to let it get out of your system. The opportunity cost of spending time on things you don’t care about is far too high.

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