When you’re going it alone and laboring on a perfect surfboard before the wave comes, it’s lonely.

“Soon”, you tell yourself. You imagine the glory and ease of cruising that wave when it comes. You won’t be all alone struggling to convince others to join you on the water.

When it comes you feel a little worried and focused on who else might is riding it. Suddenly you wish you were lonely out on the water again. All these latecomers. What if they fly right by you, even though you were out there way ahead of them?

In both cases the solution is inward. Be more selfish. Do it for you. Take joy in it because you love it. Forget being alone or in a crowd, ahead or behind. Just surf.

We humans have little knowledge of the past or imagination for the future. Present bias makes us dumb, accepting creatures. We assume what is is what must be.

People think schooling and education are the same thing. This is revealed in the way statistics are presented. “Educational level” is measured by years spent in institutional schooling.

Yet school as we know it is only about 150 years old.

Wait, what? How did humans learn stuff the other several thousand years of civilization? How were 80% of colonial Americans literate with no standardized institutional schooling, and when books were rare and costly and most jobs didn’t even require reading? How did people invent stuff, start businesses, write books, create great art, and expand the corpus of human knowledge for thousands of years without certified teachers and grades and degrees?

Really we should ask the opposite. How does anyone retain any of the natural, insatiable human hunger for learning after years in compulsory academic prison cells?

Schooling is a blip on the learning radar in human history. It will die, then we’ll look back on it like other blips. Remember when smoking cigarettes was good for your health? Remember when leeches were needed to suck out the bad blood and cure disease? Remember when people all the sudden thought, despite thousands of years of evidence to the contrary, that nobody would learn anything without being stuck in cinder block cells for 50 minute segments and forced to turn the wonders of the universe into horrible tedium?

Weird epochs in human history.

I’ve got a confession. I’ve been mailing it in on the blog the last several days.

I’ve published my daily posts on schedule, but the content has been pretty weak, more about checking the publish box than really writing anything. And I’m doing it again today.

But it works for me.

Most things aren’t worth doing if you don’t do them right. Blogging is not one of those things for me. It’s like exercising, eating, or personal hygiene. Sometimes it’s too costly to do it super duper great. But it’s definitely better to get in a few push-ups, get some calories, and wash your face than to ignore them entirely until conditions are perfect.

Daily blogging is for me, and the primary benefit is the routine, therapeutic nature. Yeah, I don’t feel great when I published something weak. But the benefit I get of just sticking with it and getting something out there until I can do something more substantial is worth the cost of a weak post. Non-zero days build momentum, and getting and keeping momentum might be the greatest path to success.

So here it is, another one mailed in! As long as I keep at it, I’ll get some great ones out every so often. Until then, one more day checked off!

When considering whether to raise venture capital, entrepreneurs go through the pros and cons. Growth capital, potential insight and connections, weighed against more rapid timetable, potential meddling or pressure, etc.

These are big, important considerations. There are also some more personal considerations a founder should think through. What’s your style? What’s your personal pace? Do you like keeping people in the loop and getting feedback, or do you hate it and want to be left alone? Do you value bigger swings with bigger upside, or more flexible meandering grind?

It’s also worth thinking about how investors change your mental game. No matter how much you know they don’t need or expect every company in their portfolio to win big, you will feel the need to win big for them. You will feel a pull to define the what and how of success on your idea of their expectations. No matter how much you may think pleasing investors won’t weigh in, it will. It’ll be in the back of your mind. Not a big deal, but one more thing to juggle in a complicated stew of expectation management.

If that sounds torturous, you may not be a great fit for VC.

I never thought I was. And for half a decade, I wasn’t. But at some point, after clarifying a vision of something that I could see going 10x bigger and faster with VC (even though taking on VC makes margin for error 10x smaller), and finding a truly amazing VC match, I made the leap. I like it. Jury’s still out whether it ends up being better than the solo bootstrap approach, but I’m glad I jumped in. Complicating though it can be. It adds one more thing that can subtly distract from the customer, but it’s brought a lot of excellent stuff too – mostly pushing me to think bigger, faster, and clearer.

There is no such thing as an isolated fact or experience or data point. They all exist in a context, interpreted through a frame.

We all know this, but it’s still easy to underestimate just how important framing is. An experience can be two entirely different things with different framings. People may go from ignoring it to paying hefty sums for it, based on framing alone.

The more you dive in and try to deconstruct the phenomenon of framing, the more it feels like life is nothing but a series of frames, layered and nested in and on one another. If you get the right frame matrix, you get the right result.

The only trouble is, nobody knows what that is. Maybe it starts with reframing framing.

A friend once called the plummeting cost of information “The Infocalypse”. So much info flying everywhere might soon fry our brains.

A bit dramatic, but there’s an economic reality here. Info costs were the main driver of many social and commercial institutions and relationships for most of human history. They keep dropping, changing everything.

When they get low enough, the most important structures may move from those that lower info costs to those that raise it. Or at least raise the cost of certain types of info to leave space just for the desired kind in a sea of noise.

It’s possible the wide open web will be considered gauche before long, and semi-private communities and gated, filtered, managed info markets will take over.

The internet is so, so young. It may look nothing like itself in a decade or two.

How exciting!

I’m on the road with the family the next four days, driving from Oklahoma to San Francisco. Gonna be a bit crazy, but I’m committed to daily blogging so I’ll fit it in one way or another.

I love driving across the country. There are so many cultures inside the American meta-culture. They all share a thread of American rebellion and individualism, but each with their unique twist. The result of a nation of immigrants, misfits, and risk-takers.

When it rains, it pours.

It seems like those times when you really just need a win, it doesn’t come. When you need something good to happen out of the blue, you don’t get it.

Then again, when things are rolling, they start to roll more. When you’re winning, you get more wins. Unexpected good fortune follows expected good fortune.

I guess the lesson for me is twofold. First, never put myself in a mental position where I need something outside of my control to happen in order to be okay. It won’t. Second, enjoy and celebrate the wins, lean into them, ride the good fortune horse hard and get the most out of it.

I was talking to someone this morning about big companies like IBM, Oracle, GM, etc. and how they get stagnant, bureaucratic, and fail to innovate with time and success.

Everyone wants to figure out how to prevent this calcification. But should we?

People mature. Adults aren’t like kids. They don’t have kid bodies or kid minds. They don’t take kid risks and see the world through kid eyes. They have history and experience. The have grown and changed and learned. Sure, they can learn bad stuff and grow in bad ways. Yes, it’s worth trying to keep some childlike wonder.

But adults with histories who act like wide-eyed kids are not healthy.

Maybe organizations are the same. Maybe innovation is a kid thing. Maybe a company with millions of customers and billions in revenue constantly pivoting and brainstorming and re-positioning would be sorta wrong. Maybe the well-functioning older, large firm is one that continues to deliver consistent value to a large market with healthy margins until they get too old and die.

Remember, companies are made of people, but when firms die people don’t. They re-organize and re-assemble and re-configure and the core value prop of the company to its customers gets replaced by another business or disaggregated to many.

Maybe this isn’t a bad thing.

Of course if I’m the head of a mature multi-billion dollar company, I’m sure I’ll feel the tug of innovation and chafe at boring bureaucracy. But maybe that’d be a sign I should leave and start something new, rather than try to force a corporate Benjamin Button.

I’m not really sure. I’ve never been as much a fan of reform and resistance as new creation. Whatever the balance, I don’t think it should be accepted uncritically that all firms ought to always act young and innovative.

Writing is too broad a term.

There are two distinct activities that involve typing words. One is a creative act that takes a lot of will, focus, clear thinking, and imagination. The other is a consumptive act that requires nothing but a little free-flowing initiative.

I am almost entirely a consumptive writer. These daily blog posts are for me, not for anyone else. They are therapeutic more than any other goal. Every morning, I sit down and write because the act of doing so feels good and gets my day going. I have no creative, productive goal with the content. I’m not trying to teach or motivate an audience.

Sometimes I do creative writing. An article for a third party publication, or a topic I’ve thought about a lot and want to communicate to a specific audience. It’s a whole different beast. I imagine writing books is like that on steroids. All of my books have been after the fact thematic compilations of my writing, rather than big plotted out works of creativity.

I think consumptive writing every day makes creative writing better, but it can also make me a bit lazy. Writing without accountability for the outcomes is easy, and when I switch to creative writing if I’m not careful I can let that easiness slip in.

Humans can’t survive without meaning.

But finding meaning is overrated. Creating meaning is the real super power.

I used to take the rationalist approach to things like holidays, rituals, or special occasions. Why should any day have more value or good fortune than another? Seemed stupid to make some sun cycles more special than others and get all worked up about it.

Now I have a more useful approach. Special days and rituals do have meaning if I choose to give it to them. It’s like a power boost in my back pocket. I can create meaning in days that others already find special, or brand new ones. Rather than deny or decry the power of special occasions, I can use them playfully to have a better life.

Whether or not it’s a necessary or objective part of reality, humans think in cycles and seasons, and narratize these to give some more meaning than others. There’s a rhythm to it. On days, off days, and training days. We can let the meaning be imposed on us, or we can choose our own rhythmic calendar. We can work with or against the forces of nature. Both can be useful.

Rather than trying to discover where you are in someone else’s story, you can decide where you want to be in your own. This is powerful stuff.

Today, I’m starting a new notepad. The other one got full and I scanned it for anything I wanted to keep, then threw it away. Today, I crack the blank pages of a new place to sketch ideas and to-dos. I think I’m going to choose to make today a momentous day; the beginning of a new season of life. A new notebook will mark a new level.

A created this post to mark the occasion.

(See how it works! It’s fun!)

When people think about working a ton of hours, they tend to assume the benefit is that you get a higher raw number of productive hours. I think one of the bigger benefits is that you get to work when other people are not. It’s not just the quantity of hours, it’s also when they occur.

An hour of work in the middle of normal working hours is less valuable than an hour of work outside hours where everyone else is also working.

This is why I love working on minor holidays (which I consider to be any holiday other than Christmas). There’s something magical that happens to my thinking and productivity when the world is silent. Few emails or Slack messages coming in. No latent feeling of the need to be available. No sense that my work is more just me floating downstream with everyone else. It’s clearly, quietly, just me and my focus. And it’s glorious.

Most of the time, I don’t like to work tons of hours. I’d rather have some of those hours with my family. But I still want the benefit of working when others aren’t. The best way is often to just get up a few hours before most work starts for most people. And to work a few early hours on weekends and holidays. Right now I’m on the west coast, which makes this almost impossible. Even if I get up a five AM, half the working world is already at it, and so is my inbox and peace of mind. Out here, I feel like I have to start early not to get ahead, but to prevent getting behind.

But counter-scheduling works here too. At six PM, most of the rest of the world is watching Netflix and winding down. The late afternoon and evening hours out here are so much quieter. Pushing my work further on the other end brings big benefits. I prefer morning solo work, but I can adapt.

I try to set up my week so that at least one third of my productive time happens counter to the work time of others. I probably get two thirds of my work done in that time; if not in quantity then in quality.

It’s kinda fun to document various phases of thinking and brainstorming along the way as we build a product and company.

A few pics I found on my phone. Some from almost a year ago when Crash was an idea, some from a few months ago as we dialed in the beta, some from last week.

It’s important to be unafraid of looking like an idiot. It’s also important to minimize the cost of looking like an idiot.

The higher the cost, the greater the fear, which strangles innovation and learning. It’s easy to focus on the “don’t be afraid to look like an idiot” part and forget about the lowering the cost component. True, you don’t want to shut yourself down to avoid looking dumb, but you might harm yourself without even knowing it by being dumb in high cost environments.

It helps to pick a padded room where you can be an idiot without hurting yourself.

In my case, I use people.

I get a lot of ideas that feel super awesome. I’m very action biased so I want to go do all of them immediately. Unfortunately, the majority of the ideas turn out to be dumb. Before I go talking about or acting on them, I’ve learned to test them in an environment where the cost of stupidity is very low.

I call my brother Levi or my friend TK.

They are both great idiot sponges. I’ve heard Secret Service agents called “bullet sponges”, since their job is to jump in front of a bullet to protect their client if need be. These guy absorb my stupid ideas before they have a chance to harm anyone. They provide the padded room I can be reckless in without harming myself too much.

Most of my big ideas now get filtered through one or both of them before I take any other action. They allow me to have the best of both worlds. Fearlessness about my reputation or looking dumb, and near-costlessness for when I do.

I can’t tell you how many times they’ve saved me from my own stupidity.

Find an idiot sponge and use them.