For a very long time, I intertwined it with my career and now that it’s disentangled, I realize it can become a much purer version of my thoughts, a kind of diary of sorts, and can provide value for interested people without trying to be linkbait.

I was reading Aaron Swartz’s blog recently, again, and looking back at the Raw Nerve series, thinking about an earlier internet where things seemed complex at the time, but in retrospect were very simple. After he died, I would find myself thinking about him on occasion – I think we influenced each other despite never having met. So I was happy to connect back with his work, which people have kept online as a way of remembering him. (Thanks for MEK for helping me do this.)

These days my work is simple. I try to serve more people better that use our stuff and work hard at being a good entrepreneur and human being. So this isn’t flashy because it doesn’t need to be; I’m just out here getting my sea legs again.

That said, the world is way different than it was when I started writing here, so all the people who used to hang out here may be gone. Who knows?

If you are here, and you see this, comment so I can try to understand how dark this room is.

The post Writing for its own sake appeared first on In Over Your Head.

Is it more difficult to make decisions in? Is it fundamentally easier, or harder?

Is tomorrow going to be better, or worse, than today was?

There are a set of assumptions so fundamentally deep inside of you that they are very very hard to change. They may not even be changeable. I have no idea. I’m just a guy with a blog.

But I am here from the future, and from the past, with a suggestion.

If you are not a marshmallow eater – in other words, a person that is sacrificing in the present for the future – please, on occasion, eat the marshmallow.

If you are, instead, a person that does eat the marshmallow regularly, try in fact doing the opposite.

In fact, the best thing you can do for yourself is to probably be conscious of what type of person you are, and to deliberately do the opposite, on occasion.

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You only learn your sweet spot by finding it and being in it – or, if you’re close, by listening to your feelings. They might be big or small so you might have to get very quiet.

At Breather I ran everything from an office. I ended up having to do of what I sometimes now call productivity theatre, which is when you have to be in a place to appear productive in front of others.

At the current company I started, Practice, we do none of that, because we are remote. So I just work on what matters regardless of what it looks like. This is closer to my sweet spot.

I think the objective of life is to get as close to your sweet spot in many parts of life as you can, for as long as you can.

I remind myself of this sometimes with the prompt: “Have you experienced the sacred recently?” It pops up in my todo list and it reminds me that there is more than the everyday out there. (Most of the time, in my case, this turns out to mean more time in nature.)

Your sweet spot not too easy, and not too hard. It relies on your natural skillset and on some of the things you’ve worked hard to learn. It makes life closer to the experience of a video game, which is that “just right” level of difficulty.

So try to find it, and try to stay there.

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I am one of you, so I know you.

I learned a long time ago that one of the things I am very sincerely good at, uniquely good at, is precisely this skill. Delaying gratification for an insanely long time. An unreasonable amount of time. It has had its uses, for sure.

If you are one of these people – this tribe, like me, I just want to present to you that perhaps, it’s time to consider whether one marshmallow actually is enough. Whether it has enough value for you. Whether you can get what you want out of that single one.

Because if you just eat the marshmallow, guess what, you can just leave the experiment. If you wait for the second marshmallow, once you get it, you have two, but you also waited a really really long time.

So the question is to ask yourself is really – hey, maybe the time is more valuable than the marshmallow.

Think about it.

That’s it. That’s the post.

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Some things will change here shortly. No expectations as to what.

Comments will likely go off. The internet has changed and there are too many places for comments – too few for just pure writing.

There are too many places owned by others – so it’s important to own something yourself.

Less links, and less media, probably – there is already too much of that, too.

Less gimmicks. Etc. Although we’ll see. Gimmicks tend to take off (a few of mine have), which makes them hard to resist.

I’ve been asked to keep writing more times than I can count but there is a conflict between running a company (of a certain type) and writing plainly – because you are always in view. So you kind of have to design your way around that. I eventually figured it out, but it took several years.

You can see above a photo of me at the age of 40. If you look around, you’ll find photos of me at 30, as well, and probably 25, because that’s how long this blog has existed.

You’ll note that I am the same person – the same creases and lines and everything else. Everything has just deepened.

So I imagine that’s what will happen here. Things will deepen.

Whatever that means.

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Over the past few days, all over my Facebook stream, I can see pictures of entrepreneurs looking successful, when I know for a fact that they are not successful at all. It’s weird, and it creates a strange broken mirror effect. But of course, it’s inevitable.

In 2004, I had just started podcasting, and was lucky enough that I ended up being one of the first podcasters in the world. Good timing and a decent radio voice had given me my big break. Not bad.

But what happened after that is far more interesting. I ended up quitting my job, focusing on doing my podcast full-time, and failed. I had accumulated a ton of credit card debt over a few years, gone through some RRSPs (Canadian 401k’s), and was at a pretty bad place after a while of doing this – pretty deep in debt for a 24 year old. It was really hard, and then suddenly, I had gotten a break while working at a homeless shelter, of all places. I got an email from my podcast company saying I had made something like $10,000 in two months.

“Holy crap!” I thought. I had never seen that kind of money in my life before. Ever. Suddenly, my life had turned around. From one day to the next, I was no longer in debt, and I wouldn’t have to start over. I had crossed the dip.

But up until that time, I was basically faking it til I made it. The exact same thing I accused people of, above, when I posted that on my Facebook wall a few days ago.

As soon as I posted it, the deluge of comments was crazy. I got a bunch of private messages. “I’m faking it right now!!! I’m miserable!!!” And then I got a bunch of questions asking me if my startup was doing alright.

Lucky for me, it was. I couldn’t tell them then, but our numbers were great, and I was announcing in the next two days that Breather had raised $6mm in venture capital from RRE Ventures (this is public now). But the crazy part is, from the perspective of all the people on the internet, failure and success basically look the same until that final moment when you discover the truth. Nobody knows the difference. We’re all trying our best to be the duck – looking super cool above water while paddling like crazy underneath.

But ducks were born to swim. Most of us have no idea what we’re fucking doing.

The main concern isn’t playing the game – I guess it’s natural, although I’m sure it can be lonely at times. The problem is that the endorphin rush of fake success kind of feels the same as real success, for a while. It’s why you and I post selfies every little while. Feels good to look good! Oh man, am I great.

Well, not really. You’re like everybody else. So remember to actually get the work done, not just impress others with photos of what internet celebrities you’re hanging out with. That’s how you actually get to enjoy it later. Or at least, that’s what I see on my Facebook feed.

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Basic thesis: Everyoneâ€s mind is crowded. Your idea needs space in the brain to survive. The right name enables this, and more.

Hereâ€s how to find a great name— for your company, your project, or whatever else.

Why I wrote this: Iâ€m really good at naming things, for a few reasons.

One, I spent years looking at domain names around 2007-2008. I know the domain name industry inside and out. Iâ€ve looked at and bought and sold thousands of names.

Two, for some ineffable reason, I am great at simplifying things down to their component parts.

Three, I am hyper picky about what makes a good name, both visually and verbally.

Four, I have successfully found names for several of my projects that are absolutely world-class. See: Breather, The Flinch, my new business, etc.

10 Rules on How To Name Your Company

1. A good name is simple. But more than simple, a great name goes to the base of what the company does, both describing it and expanding on it.

Example: The process of naming Twitter by Noah Glass is described in Hatching Twitter, which was recently released. Regardless of how close to the truth it is, “twitter” describes it perfectly, as it is a short, irreverent/irrelevant sound. From this, the idea of birds emerge, making it even better (but honestly, it could have been anything).

2. A good name is a noun, and its use can be shortened to either make it into a verb or a noun.

Example: My startup Breather is a network of rooms for work or rest, which at one point were called “Breather rooms,” but which since have been shortened by users to simply be called “Breathers,” as in “I just rented a Breather.” This makes word-of-mouth infinitely easier.

3. A good (domain) name passes the phone test.

Example: Re: (Fiverr.com)

Person 1: “Oh yeah I just used this service Fiverr.”

Person 2: “Fiver, awesome.” (Types it into phone.) #FAIL

Oops. Your service better be damn good if people are willing to spell it out every time.

Funny story actually, a VC I was recently meeting with literally typed in Brether into his browser to search for us, because he had already assumed my company was spelled wrong. He was shocked we owned Breather.com. Another side note, some people (Iâ€m looking at you Jason Calacanis) have rules around investing or not based on how good your name is.

4. (A corollary.) A good domain name is worth any price you are capable of paying.

Example: Breather.com cost me $7,500, which is a steal, and I bought it the very same day I thought of the word. Likewise, your companyâ€s Twitter handle needs to be easy to obtain as well. I consider those to be the primary ones. FB, Google+, all the other stuff, donâ€t worry about it.

5. Combinations of two words are ok, and can even be great (though Facebook is actually one real word). With word combos, it has to roll off the tongue, which means two or three syllables, but almost never four.

Example: Microsoft and Pinterest, ok. Shopkeep, awesome (based on a real word). CreativeLive, started by my buddy Chase Jarvis, is a good exception to the not-four-syllables rule.

6. Now Iâ€m looking at you, French people. If your company name sounds like English to you, but sounds fucking weird to native speakers, choose something else for Godâ€s sake. A random invented word is better than the stuff you made up.

Example: PearlTrees? Wtf. SoundCloud? Absolutely.

7. Do not, I repeat, do not name your company very similarly to another startup, especially a successful one.Â

Example: … I have one. But theyâ€re kind of friends, so Iâ€m keeping it to myself.

8. If you canâ€t come up with anything, try changing one letter from something you really want, or something that sounds like a real thing.

Example: Mustbin. I havenâ€t looked up what they do, but if itâ€s not about wish lists, I retract my recommendation.

9. You can find a good name just by free writing, and doing so for an absurdly long time.

Just keep writing and writing. Seriously. Do it in a text file. Keep writing until you reach 10,000 words. The right name will come along, as long as you keep writing.

Example: Just trust me, this works.

10. Look, eventually, none of this will matter. But right now, it matters a lot. Your company name is your identity. Think about it for a LONG TIME.

The post How To Name Your Company appeared first on In Over Your Head.

Here are a few ideas about what the future could look like.

I wouldn’t consider these holy writ; more like provocations to think about.

A. Bitcoin becomes extremely popular, replaces gold as a stable currency because of its algorithmic, predictable, stable nature. Bitcoin ATMs on every block.

B. Home Depot becomes a giant room, 2% of its usual size, with 3D printers in the back that just print out whatever it is that you want. No more inventory.

C. Amazon does the opposite. Opens warehouses that become showcases for the few things you have trouble ordering online… fridges, etc.

D. Your smartphone becomes your wallet, your ID card, your keys. Segments society into smartphone users (who have access to the best services), and non-smartphone users (who donâ€t).

E. Social networks become generational, with each successive generation abandoning the previous one and software using more highly viral methods to reach the generation that is not yet captured. See: Snapchat, WeChat. Eventual boom/bust cycles cause great instability. OR…

F. Social networks obtain permanent place in the stage of life of the participant. i.e LinkedIn becomes the dominant circle when your work life starts to gain in importance, then declines once you retire. Etc.

G. Google Fiber threatens to put all other telecom providers out of business as a result of their intent to “organize and make available all of the worldâ€s information,” theorizing that slow internet prevents access to information. Anti-trust legislation follows. See Jason Calacanis†Launch list for more on this.

H. Wars develop for each location a piece of hardware can exist: the eye, the wrist, the hand, the desk, etc. Nike probably wins the wrist. The rest… I mean, hey, hard to bet on anything else but Google.

I. Increasingly peer-to-peer services replace everything, as they create efficiencies where middlemen are unnecessary. Offices (obviously), restaurants, tours, travel, flights… everything. And remember, the inevitable end result of all technology is omniscience and telepathy. Or extinction. (Only slightly kidding.)

The post 9 Ideas About the Future appeared first on In Over Your Head.

Chris Dixonâ€s Twitter account

Who knows if itâ€ll end up being true or not. But it makes some sense and itâ€s worth discussing.

If youâ€re familiar with Peak Oil, youâ€ll inherently understand this too.

Hereâ€s the theory.

Key indicators for online advertising effectiveness have declined since the launch of the first banner advertisement in 1994. These declines are increasingly placing pressure on even the most established businesses in the space.

These developments suggest important (and potentially painful) implications for market structure, privacy, and authenticity online.

Existing alternatives appear at present to be insufficient to replace lost revenue from near-future declines in the value of display, search, and mobile advertising.

Ultimately, the economics of the web will necessitate pivotal decisions about the financial underpinnings of the Internet in the decades to come.

Letâ€s rephrase: Users are becoming more sophisticated and clicking on ads less than before. Ads are less effective, and are plagued by click fraud, driving prices downward. This will eventually becoming such a problem that it will threaten entire businesses (Twitter, FB, whatever else) we have come to take for granted.

These businesses will therefore have no choice but to begin invading users†privacy further and further to help target their ads.

Due to the nature of math, companies will also create massive monopolies / oligarchies to create efficiencies, allowing them to remain profitable despite these problems.

Whether it turns out to be true, well… itâ€s interesting either way, isnâ€t it?

All the more reason to do things while they work. All the more reason to attempt new things to gain advantage now, while they work.

Hereâ€s the full PDF in case you are curious.

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Itâ€s pretty much undisputed at this point there is a connection between successful venture capitalists & entrepreneurs, and listening to hip-hop music.

This is totally unscientific, of course. But it makes total sense to me now.

I donâ€t know when it started, but these days, Iâ€m seeing it everywhere.

And I know itâ€s crazy, and I know Iâ€m making something out of nothing here, but I sincerely believe that there is a correlation between ambition and listening to rap.

Hereâ€s Ben Horowitz (of A16Z, investors in Instragram, Airbnb, etc.) talking about how Kanye Westâ€s Stronger helped Ben process “11th-hour, late-night auditing mishaps that almost stymied the $1.6 billion sale of Opsware.”

We also know that Horowitz†love of hip hop was a factor in the firmâ€s $15M investment in Rap Genius, a rap lyrics site that is trying to be the meta-data layer above everything (actually a cool idea).

Hereâ€s Mark Suster (a well-known blogger and VC) relating his entrepreneurial experience to 8 Mile.

Pretty sure Fred Destin listens to it even though he claims his main influence is Crystal Castles.

And hey, hereâ€s Shervin Pishevar (Uber, Tumblr, etc.) tweeting out Pusha T lyrics. Clearly Iâ€m onto something.

“Ballers put numbers on the boards. How could you relate when you’ve never… â« Numbers On the Boards by Pusha T — https://t.co/Wr0fdMFU3Q

— Shervin Pishevar (@shervin) October 16, 2013

Am I just seeing things? Maybe.

But Iâ€ll tell you what listening to outrageous, sometimes super arrogant music does to you.

It pumps you the fuck up. It makes you feel capable— like you can take on the world.

I think that either ambitious people listen to hip-hop, or, rap makes people ambitious. You decide. But check this.

A lot of rap actually is about business.

Letâ€s take an easy one: 10 Crack Commandments by Notorious B.I.G.Sure itâ€s about slinging crack-cocaine. But it also actually offers good advice.

Not kidding.

[Rule] Number 2: Never let em know your next move

Number 4: Never get high on your own supply (never believe your own press)

Number 7 (this rule is so underrated): Keep your family and business completely separated

Other songs teach you about haters, about spending too much money, or focusing on yourself instead of others.

Now, a lot of people might say itâ€s a bad idea to take advice from egomaniacs.

Nonsense! I think thereâ€s something to learn from everyone, as long as you consider the source before deciding. (I also think this about crappy self-help books btw.) And hey, they did make money, they clearly know something.

Anyway if you wanna get yourself hyped-up, hereâ€s my top 5 tracks to get me super enthusiastic.

And in case youâ€re wondering about my credibility well… this was before your time, but although I am the whitest man alive, I did have a hip-hop radio show on Sirius Satellite Radio. So.

Anyway, enjoy! Now go do something amazing.

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