Natives reunited in the wild

I made a series of t-shirts last fall to experiment with some design ideas and share some of my personal messages. I’m happy to say that I got a really positive reaction to a bunch of them – and so this February I decided to produce a second series. I showed up here in Mexico City on my way back from Oaxaca and I was surprised and delighted to see that my friends Florian and Nicky were in town. Thx Instagram! We met up for dinner and Florian had the good sense to wear the NATIVE shirt that I gave him when we met in Brazil in November – and so we got to capture a side-by-side of the two versions! I’m wearing NATIVE #2 on the left and he’s wearing NATIVE #1 on the right. Stay tuned for more designs from series 2!

Natives reunited
Natives reunited

Athletics and Intuition

I’ve spent too much time trying to make decisions. And you know what – deciding isn’t really any fun.

I’m always happier when I flow through life using my intuition. I’d really like to be making zero decisions and living intuitively all the time.

“…we are largely better at doing than we are at thinking…”

― Nassim Nicholas Taleb, Antifragile: Things That Gain From Disorder

This led me to ask myself, how do I get better at living intuitively? How do I train my intuition? 

To jump ahead for a moment, the simple answer is: you get better at what you do often. You can train your intuition by acting intuitively, by using your intuition in any way at all really. But I was kind of stuck, I was used to making decisions – or trying to make decisions – and I was out of touch with my intuitive self. I needed something more specific, a usable, understandable technique that would improve my intuition in a noticeable way.

At the same time that I’ve been thinking more about intuition – over last few years – I’ve also become more and more athletic. I was always very active but until recently I didn’t pursue anything with goals or training, or even on much of a regular basis.

“To realize the body’s potential for flow is relatively easy. It does not require special talents or great expenditures of money. Everyone can greatly improve the quality of life by exploring one or more previously ignored dimensions of physical abilities.”

― Mihaly Csikszentmihalyi, Flow: The Psychology of Happiness

And here’s the thing: once I started being more athletic, I started to notice an improvement in my intuition. The more time I spent doing things with my body, especially authentic physical activities that get me into flow, the more I noticed this effect of improved intuition. I started to think about what the connection is between athletics and intuition – how does being athletic improve our intuition?

This is the answer that I’ve come to: When you’re engaged in authentic physical activity (especially outside), your body is responding automatically – intuitively – to the environment, to the situation as it comes. As you practice this intuitive movement, we train our physical intuition, simply by being active outside.

And then – here’s the magic – the mind observes this, sees the body doing its thing, sees physical intuition happening, sees that the body goes where it needs to go without having to be told where to go, and learns that this is possible. Our mind learns how intuition works – and that intuition does work – by observing the intuitive movement of the body.

“…wu-wei is probably best rendered as something like “effortless action” or “spontaneous action.” 

― Edward Slingerland, Trying Not to Try: The Art and Science of Spontaneity

If we are active and in flow on a regular basis, the mind has plenty of opportunities to see that spontaneous, effortless action of the body leads to good results. It just works, all by itself, without having to make decisions. The next step is that the mind sees this and says, “hey, that seems to be working for moving the body, let me try that for myself. Let’s try some spontaneous, effortless thinking and see if that works just as well.” And (for the most part) it does go well, which reinforces the mechanism, making it more likely that the mind will allow itself you to go in that direction in the future, to allow intuition to happen, instead of going into more of an analytical, decision-making mode.

We can train and improve our intuition by being physically active (outside). The connection between athletics and intuition is so powerful that I now see that as the central theme of my work.

Authentic Physicality

Human-powered, self-directed, challenging, outside. 

We all know that physical activity is good for us.  Exercise ain’t all it’s cracked up to be though. It’ll certainly help keep you alive longer, and many people love their workouts, but it’s called a routine for a reason, right? I think there’s a better model, and I’ve come to  call it authentic physicality. To get in flow, to feel good, I have to be engaged in AP at least once a day. If I really want to feel great I need to do a double, or stay in AP for more than a couple of hours, and I know I’m really putting awesome in the bank on those rare days when I can get into AP in three or four different ways, for several hours at a time. 

Let’s break down what I mean: 


First of all, you have to be doing something human powered. If you’re not moving yourself, you’re not really moving. This is part of why I gave up riding motorcycles: it’s super fun, it’s self-directed, challenging, and done outside, but it doesn’t really provide any physical exercise, and it requires using an engine. And – even if you’re moving yourself, if what you’re doing requires external power as an intrinsic part of the activity, it’s not going to be as fulfilling – and it will likely be more expensive and energy intensive. Human-powered activities are also, very simply, simpler. We don’t need any extra complications in our world. Another thing about motorcycles that I realized at some point was that I no longer enjoyed having the machine and all of the process and tools required to keep the machine alive. We pay rent on everything that we own, and especially with machines – our machines own us as much as they require us to maintain them. 


I find self-directed activities more interesting. This means figuring it out yourself, for the most part. Having a mentor or a leader is great, but if someone is holding your hand every step of the way, it’s too easy to lose awareness of what is happening and what you are doing. Americans love guided activities. Get a guide if you need one, but don’t just follow; work with the guide, and only as long as you absolutely need to. And then try leading something yourself. We’re all capable of leadership, and it’s far more fulfilling than otherwise. 

Note that I mean self-directed, not alone. For mean this usually means doing individual activities like kitesurfing with other people. Climbing falls somewhere in the middle as it’s most often done as a pair activity. Team sports can also require a lot of self-directed activity. 

How to use this criterion? I went on a short river rafting trip last year that was human-powered, challenging, outside, and definitely not a ride, but we basically just paddled when the guide told us to paddle. The activity felt good, but I don’t think it fully qualified as authentic physicality. 


Doing something that isn’t intrinsically at least somewhat challenging is simply boring. Same if you’re doing something that you’re already so expert at that you can do it with your eyes closed. However, as Mihaly Csikszentmihalyi points out in Flow, it doesn’t have to be – in fact, should not be – something so hard that you simply can’t do it. In fact, completing attainable goals, achievable challenges, is a key part of getting into flow. It feels great to level up, and it’s good to do that as often as possible. Progression is great. If you’ve mastered something, find a way to introduce a challenge again, and/or start teaching others (which is itself a challenge). 


Being active outside and in the natural environment is so important. Most of us live in cities and we certainly get some benefit from being outside even in urban environments, but nature is far more stimulating and inspiring. As Nassim Taleb writes in Antifragile, “what Mother Nature does is rigorous until proven otherwise; what humans and science do is flawed until proven otherwise.” Another reason, also cited by the same author, is that a “wealth of details leads to inner peace.” We need the fractal detail of natiure to occupy and inspire our minds. So: running on a treadmill in the gym is better than nothing, running outside on the sidewalk is better, but trail running in the woods is far superior and provides multiple benefits to the body and the mind. 

A note on “extreme” sports

Some people think of some of the things that I do as extreme sports. I don’t use this term. The word is vague, subjective, relative – and overused. It’s also not relevant – authentic physicality is most often not extreme at all. Most sports that might be called extreme are complicated, required a lot of gear, and can only be done in very specific locations (and this require a lot of engines/fuel). 

The back story 
I’ve always been highly physical. Although I grew up in the city of San Francisco, my parents were outdoorspeople who took me backpacking for the first time well before I could walk. I was never attracted to team or ball sports much, but I enjoyed hiking, camping, backpacking, climbing, sailing and skateboarding from a young age, and did a lot of those things plus snowboarding, mountain and road biking, windsurfing, surfing, stand-up paddling, snowshoeing and trail running through my 20’s, 30’s and into my 40’s. In recent years my primary sports have been kitesurfing, paragliding, and open-water swimming – and it’s only in recent years that I’ve pursued any sport with enough regularity, dedication and aspiration to feel like anything of an athlete. 

As I’ve become more athletic, I’ve stopped doing some things that I used to enjoy: snowboarding, riding motorcycles, sailing boats, river kayaking, CrossFit. As started to think more about why I gravitated towards certain types of activities and away from others, I began to develop the idea of authentic physicality. There are too many activities masquerading as sports that lack one of the key qualities of AP . Hooking yourself into a zip-line might feel challenging for a moment, but it’s not active, not human powered, and not really physically challenging (unless you’re catastrophically unfit). At the end of the day things like zip-lining are rides, not sports, and you won’t get fit or into Flow by taking a ride. I don’t think anyone – not even a child – is really using their time well on a ride. 


The easiest and purest way to do authentic physicality is trail running. Other great AP activities are walking, hiking, backpacking, open-water swimming, rock climbing, cycling (especially trail or mountain biking), paragliding, surfing, stand-up paddling, snowshoeing, xc/backcountry skiing, and skateboarding. There are lots more – get out there and let’s hear em! 

Upgrade your decision-making

In January 2017 I led a workshop at The Battery entitled “Upgrade your decision-making”. My goal was to share some of my thinking about Athletics and Intuition in the form of a “Decide Nothing toolkit” – a few simple techniques that I use to help me stay in flow and make decisions intuitively. Some of the techniques that I shared are

  • Move without hesitation
  • See over the mountain
  • Shake hands with monuments
  • Check your messages
  • Welcome the unfamiliar
  • Roll the dice

This workshop was continuation of some events that I hosted in 2016 at the Battery and part of a series that I will be leading through the rest of 2017 on Athletics and Intuition. Check The Battery’s Events page for upcoming dates; the next one is scheduled for April 10, 2017.

How I learned to love advertising

I always hated advertising. Perhaps that’s not quite true? I feel like I’m supposed to say that. I might have admired the verve of some ads, but I never thought of it as a good thing (imagine, some do!). I was a skater. I tried to feel punk rock. I was anti-yuppie. I did have my consumer side though: Starting in my teens and even into my thirties, I dealt with social anxiety in part by shopping. When I lived on Church Street in high school years I used to go to the record store a lot (OK), but also this particular shop that sold tee shirts in various colors, always checking for a new one (not so OK). I bought cameras, jeans, shoes, shirts, suits (lots of clothes), drinks, airplane tickets, gifts – overall, mostly clothes.

At some point I started to notice this buying impulse and channel it into non-buying. I’d walk myself through the shopping process, see how tiring and pointless it was, mentally spend the money – and be disgusted. I started to see the freedom in not spending the time and money, in not burdening myself with another thing.

In my late twenties, I took a job with a promising tech/media company. I had been working for a bigger, older software company doing consulting work, enjoying that quite a lot, when two things happened. I noticed the internet happening: I had a client, a bank in Boston as I recall, and they wanted their bank “on the internet”. This was 1996. Good for them for asking! The company I worked for said it wasn’t possible. I wrapped their big Unix server app in a perl script and had it print out HTML at the end, showed that to them and they were pretty impressed. I guess I got the picture too.

The other thing was that this job required me to get on a plane every week. There is a certain glamour in that and it wears off as soon as you come to your senses. We’ve all seen the movies about the business traveler trying to make the most of his/her situation, and it’s never that sexy. I started to realize that I felt rather homeless. Already my friends thought of me as that guy who was never around, just showed up for parties. Again, that can be fun, but it’s not a long-term strategy. Since I had already decided that I would never do a daily commute by car, and I was looking for an alternative to frequent airplane travel, I decided to look for a job that I could walk to from my apartment in North Beach.

My friends assured me this was folly. There were no software jobs in San Francisco proper. I think I knew that I didn’t really want to work for a software company. I interviewed with a few. I wasn’t really a programmer, I hadn’t studied computer science, I didn’t know any algorithms. I had seen or bought or read a few copies of WIRED magazine, and I heard that they had offices in the City. I sent someone (Joel Truher) and email. I wish I had that correspondence. We met a few times, often on the roof of the building (why?) and in the end they offered me a job writing code and managing the engineering team on the side.

I wrote a ton of perl that did nothing all that useful and tried to manage the bunch of burners that lingered in the dark with their LSD hangovers, writing code that that continually crashed Apache, Sybase, and whatever else. Everyone was up at odd hours all the time. Computers were still fairly slow; if something crashed while trying to grind through the day’s events, it would often be impossible to catch up – we had to throw away a lot of data. When I think about what got me that job, and what I was good at in software in general, I think it’s this: estimating. I’m good at keeping it in the ballpark. And this is super hard with software. Super hard, especially when you are making everything up.

Advertising just sort of crept into the picture. Someone showed me a script that Crispin wrote that stuffed ads into outbound HTML. Joel showed me some LISP (was it code?!?) that was supposed to decide what ad to shove in. He was ahead of his time. Then we decided to build a search engine: HotBot. This was before Google. We had a deal with Inktomi to provide the back end and the search function itself, so we had to built the front end – and the ad server. By then we had already served “the first ad on the web”, we must have been making some money that way, and ads were going to be a big part of the search engine from the start. We had to figure out how to serve many many millions of keyword-targeted ads per second, and then to produce accurate statistics and reports about what ads were served alongside which search terms and why.

This ad-keyword project lit up my nerd brain. I dove into the spaghetti of (thankfully: perl) code that was the back end of the ad server and made many enhancements. Using some of what I had learned on earlier systems, I managed to turn the all-or-nothing nightly process of consuming the web- and ad-server logs into a continuous parallel process that could be farmed out to as many processors and disks as we cared to throw at it. I also figured out how to make a stew of the the guts of the ad server so that it was able to hold thousands of possible keyword-targeted ads in its little mind while responding to queries, without crashing. All of this fascinated me, at least briefly. Jobs are like that sometimes.

I’m not sure if even then I was aware that I was working more and more on “advertising”. Strange that it didn’t dawn on me. I think it came down to this: the work was engaging, and I was excited to be doing something fairly unique.

AdMonsters was essentially an outgrowth of that HotBot keyword targeting project. I remember discussing it at our first meeting in June of 1999. I was proud of the work I had done – and the uniqueness was proven by the fact that our first group was so small. There were fewer than twenty people working on that crap. And it was crap. But I still didn’t really see that. It just felt good to be doing something engaging and unique.

See how hard it is to see the world from the little road you’re on? I was happy to have a good job, happy to getting paid well, happy to able to do my own thing, again, to have a unique job, feeding my ego basically. I wasn’t paying that much attention.

There were signs. I was offered a job, an up-the-ladder management position, a mega opportunity in a lot of ways, a job that would have made me a lot of money. I turned it down. I didn’t quite know why. I didn’t listen to myself hard enough. I convinced myself that I didn’t want to leave San Francisco, that I didn’t want to travel so much. As close as I got was that I didn’t want the life that I imagined having, if I had that job. That I didn’t want to be that person. This happened twice actually.

I loved putting together conferences. There’s a lot of stress, and it is repeated. That’s not the part I loved, but I didn’t hate it, or I responded well to it. And I loved the gratification of seeing it all come together, so many “moving parts” – people – all timed perfectly to create an experience over just a few days. Clearly, this engaged and enlivened another part of me. And people loved the conferences from the start. We (well, I, to begin with, because it was just me for several years) did a really good job.

The conferences were about advertising. More specifically, it was about the software that web-based publishers (companies that make stuff you read on the web) use to put ads in front of your eyeballs. That’s what a publisher does: you create something that people want to read, you either sell it to the reader directly or you sell ads to companies that want to advertise to your readers (usually both). This doesn’t have to be complicated – you can just charge people $whatever to read writing and have no ads at all, that works fine if there are enough people that will pay. But: in the early days of the web, there simply wasn’t any way to charge readers anything. And so once the media-business types got the idea that software could be used in new and nerd-fascinating ways to (theoretically) show just the right ad to the right person at the right time, a landslide of investment began to pour into ad-serving software. And since, again, there still wasn’t any way to charge readers anything, all of the time and money that would have been invested at a non-web media company in getting readers to buy or subscribe was also invested into trying to generate revenue from advertising.

This is why the “online advertising business” exploded along with online media. Media business types saw media moving online, there wasn’t any way to charge readers to read, therefore advertising was the only possible revenue stream and the magic of software was so alluring that it seemed that it would be soon possible to make advertising perfect. That is: don’t show ads to the wrong people (so: no wasted ad impressions) and only show you ads that you, er, want to see (so: in theory, no annoying ads).

This massive, multi-billion dollar industry grew up around the premise that you could only show ads for men’s running shoes to men who run, and only to men who run who want to buy running shoes soon. Does that sound like bullshit? It should.

I mean, you can try. Anything is possible with software (it’s just a question of how much it costs). You can “target” men, men of a certain age who might run, men who visit running web sites. No problem, although it turns out that even this is much more complicated than those early nerds admitted. Can you figure out if he is intending to buy another pair soon? Can you? Who fucking cares? With a billion dollars of investment funding, you can certainly try. And they did.

Online advertising has been chasing this dream from day one. In the meantime, 1) Google, and 2) it became possible to charge readers to read, so just as we have been paying to read newspapers, books and magazines, we can now pay to read similar things online, and 3) it didn’t really work that well. Basically we spent something like $20B to figure out that the cost of almost-perfectly targeted advertising is more or less the same as not doing it at all. If it costs you $100 in advertising to sell $110 more of your product, it’s not worth advertising. Even if you sell $200 more, it’s not really worth it – you’re just breaking even.

Perhaps it’s interesting that I never used advertising to sell my conference. I didn’t need to. For the most part, people who were interested heard about it, or if they hadn’t heard about it, once they did they were immediately interested. Those who needed it most sought it out and found it – and then told others. That is the essence of a useful product.

At some point I started hating my job – my company – because it was all about advertising. I hated telling people what I did for a living: I produce conferences (bad enough!) – oh, about what? – they’re about online advertising. Dead air. I loved having my own business, I enjoyed the process, the doing, the producing – and I also really loved the positive feedback that I continued to get from my customers – the people that came to the conferences who told me how much they loved it, how it changed them, helped them in their careers. But the bad taste in my mouth for advertising got worse and worse.

Was I doing something morally wrong? Certainly not. I wasn’t even doing any advertising. I was making nerds happy!

My long-standing general distaste for advertising was crystallizing into a more concrete understanding that not only was advertising just sort of dumb, it was unnecessary – really, advertising is obsolete. This started to become clear to me. I wasn’t foresighted enough to conclude: now I must get out, but it did increase my urgency.

In parallel with this I finally developed some new professional relationships, some friends and peers who understood what I was doing from a purely business point of view, understood the conflicts and rewards and encouraged me to set aside my distaste long enough to work hard enough to make a real go of it. I had been distancing myself from the business because I didn’t want to be associated with advertising, and the business was suffering – not quite badly enough to fail, but enough to make the business more of a pain in the ass than it needed to be (and unattractive to potential buyers).

When I finally came to terms with the fact that this was my story, that I knew that I didn’t want to be that guy who took one of those up-the-ladder jobs, I knew that I wanted my own business, I knew that I didn’t like advertising, and I knew that I was neglecting my own business – then I knew what I had to do. Buckle down, set aside my distaste for advertising, run the business well, and find a way to get out clean.

Now that I’ve had time to read a few books, I see that I fucking won! Hugh MacLeod calls this the “Sex & Cash Theory” – a creative person should have two jobs, one that pays the bills, and the other that is the sexy, creative one. “Sometimes the task at hand covers both bases, but not often. This tense duality will always play center stage. It will never be transcended.” In his outstanding book Antifragile, Nassim Nicholas Taleb shows how “a combination of extremes kept separate”, a bi-model strategy of “playing it safe in some areas and taking a lot of risks in others” is central to anti-fragility. This can happen in parallel, or serially (as it appears to be happening for me).

I bought my freedom, and in fact not by paying someone else – I paid off my own house, and now I can live in it. It’s strange that the house was built on advertising, but that’s how it happened. So, as much as I hate advertising, and advertising is obsolete – I love advertising.

Advertising is Obsolete

(This post also appears on here on Medium)

I’ve been saying this for quite a while, and now it’s become painfully obvious: advertising is obsolete.

Advertising is no longer needed for discovery

Advertising originated as a way to spread the word to potential buyers about things for sale. Without a sign with an arrow pointing to that drugstore around the corner, some people with a legitimate need for something sold at that store would not know of its existence. This is economically additive and a good thing.

This evolved into mass-market advertising a way to try to sell more stuff, mostly stuff that wasn’t needed, but might be wanted. This sort of advertising is a big part of the fuel of the consumer economy; it increases GDP but creates nothing, and is not economically additive.

Since the invention of comprehensively useful search engines, we can easily find whatever we might actually need, wherever it happens to be. Advertising is no longer needed to find things that we need. The fact that most search engines happen to be themselves funded by advertising is a historic artifact; there’s no reason that they must be funded by advertising simply because they currently are.

Media does not require advertising

The widely-accepted idea that advertising is an intrinsic part of the media business model is false. Just because advertising is part of most media businesses doesn’t mean that it must be. As Ev Williams outlines in his piece on The Rationalization of Publishing, other forms of media (TV, music, books) do not depend on advertising, and yet we’ve continued to operate under the assumption that for some reason news is different. He sets up three strawman arguments as to why news might be — and isn’t — different. I mostly agree with those points, but I believe that there are two additional (and equally misguided) reasons that we’ve believed that news is somehow different from other types of media.

Software was supposed to be magic

Big ideas have a long legacy. Riding along with the early meme that “information wants to be free” was the technocratic fantasy that software would make online advertising work so well that it would again become an economic benefit — a way for people to discover things that they need (or really want), and that they would have otherwise not been aware of. While this does happen to some small extent, we have treated the personal data that is required to make this possible as a zero-cost externality. If we factor in the real value (any value, really) of this data, the net economic value of the discovery of a product by way of highly targeted internet advertising becomes negative. Many companies and countries are now taking steps that take this negative impact into account, making such advertising much more difficult, impossible, or illegal.

In addition to the hidden cost to individuals of sharing all this data, the cost of processing all of this data was vastly underestimated. For most online publishers, the complexity and cost of building and operating software to ‘serve’ advertising to their readers is more than the return on that investment. Online advertising never has been that profitable for smaller publishers, and it will prove not to be profitable even for the largest (Facebook, Google).

It’s true that in those early days of the ‘net it didn’t seem possible to simply charge people for what they wanted to read. Serving ads seemed like an easy alternative, and once we started down that road, we kept at it, even though it turned out to be much harder than we originally thought. And because of our love of software and of problem-solving and our stubbornness and our reluctance to abandon sunk costs, we kept trying to make online advertising work long after we should have simply reallocated all that effort to finding effective ways to charge readers directly.

As we now know, it’s not at all impossible to charge readers directly, but because we had put so much effort into trying to make online advertising work as the sole form of economic support for online journalism, we back-formed the idea that online advertising is the “only rational model” that can support online journalism. Bullshit. Advertising seemed like an easy way to support online journalism, it wasn’t, it’s not, and it’s time to move on.

News was supposed to be free

The “free press” is a nice idea but somehow along the way we confused free speech with free, as in beer. Again, because of the roots of the internet we became enamored with cheap, or even free news. Ev Williams said it well in the same piece I referenced above:

There is — and probably always will be — a surplus of free content. But that’s like saying there’s a surplus of free food in the dumpster behind the alley.

We’ve been dumpster-diving for news for long enough, and, needless to say, the effects are showing. Don’t think that we’ve seen the bottom either — it’s likely to get worse before it gets better.

Advertising adds no net value to the world

We need to discard the misguided assumption that news is somehow better if it’s free. As with any other product, we will pay for information that we actually need, want, and use. Advertising came to be part of the media business model as a way to support the creation of media not that readers wanted, but that advertisers wanted. Real companies make products that people pay for. News is no different.

Anything one needs to market heavily is necessarily either an inferior product or an evil one. (Nassim Nicholas Taleb, Antifragile)

All of what is spent on advertising could be used to make better things — or not spent at all. Nobody would shed a tear if we turned advertising off, and nor would it harm the economy. I include advertising in my list of things that we’ll look back on as 20th-century ideas whose time came… and went.

Advertising is obsolete.

(This post also appears on here on Medium)

Always Ready

Swimming in Aquatic Park
Swimming in Aquatic Park

One Day in September

I jumped in the water
cold water
I swam in a circle
not a small circle!
I fought the current
something that might seem like a battle
but I held the water’s hand
and it pulled me
I pulled myself
I felt free
not for the first time
for the first time
I felt strong
not for the first time
for the first time
I was not afraid
swimmers and surfers don’t talk about sharks
the water of the Pacific is not cold

I swim in my own skin
I embraced the open water
I took in the view of the sky
and the taste of the salt

I rounded the corner
Alcatraz to my right
the Gate in my sight
I went with the tide
and flew with my friends
back inside the arms of the pier
a little safer
but again the current challenged my strength
I had been in the water now
for more than an hour
my right foot was numb
and yet my arms felt long

things always get harder for me when the end is in sight
at a mile and a half I had to pull hard
the tide rushed out through the pilings behind me

the remarkable thing is that I would say that I struggled
but it wasn’t a fight
it was hard
but I loved it
I felt awake and alive
long and lean
warm and wise

once we finished our swim I walked slowly inside
I sat in the sauna for what seemed like an hour
my brain slowly reconnecting
to my body as it thawed

I reflected on a decision I had made only just a week before
to not wait and test the water before jumping in
to not feed my fear by feeling the cold
before feeling the cold
I had said to my self: no hesitation
at the water’s edge

my dad told me not long ago that “I’ve had it easy”
yeah right
I’m sure that’s his own trip
although it’s true that many things have come easily
I always thought I was just good at… everything
or some kind of genius
and so he’s right in a way
it’s hard to seek challenge

one day in September
I learned something more about what I’ve long said
that I’ve believed it, and felt it, but I didn’t quite know why
always ready

Bowen and IN-Q
Bowen and IN-Q

The Long Distance Experience

A new specialty in kitesurfing is emerging. Long distance kiting is different from freestyle, wave riding, racing and free riding. While all of these disciplines continue to progress, something else is happening that isn’t about tricks, waves, or competition – it’s about exploration, adventure, and the unique feeling of making a journey by kite.

Long distance kiting is about traveling not just with your kite but traveling by kite. There are parallels in other sports: in paragliding it’s known as vol-biv, in cycling it’s bike-packing. It’s the difference between sport climbing and a multi-day climbing expedition, or between a day hike and an overnight backpacking trip.

Coming around the corner to Jericoacoara
Coming around the corner to Jericoacoara

Long distance kitesurfing can be done with just about any equipment, at any pace, in many places, and with varying degrees of support. Long distance kiting is its own thing, and for many of us it is the way that we enjoy the sport the most. Especially for riders who aren’t into freestyle or racing, and for more experienced and adventurous riders, long distance is a uniquely awesome experience and more and more kitesurfers around the world are getting stoked on long distance kiting.

It’s not just “downwind”

If you’ve been kiting for more than a year you’ve probably done a “downwinder” of some sort, either at your home spot or while on a kite trip somewhere. Usually this involves riding a few miles/km from a known launch and getting a ride back to where you started from. I did my first short downwinders at Ocean Beach in San Francisco and on the Outer Banks in North Carolina. It’s a great feeling to ride with the wind and know that you don’t have to worry about getting back upwind – just jump in the car/buggy/taxi/bus, and enjoy the ride back home!

These little downwinders are super fun, but I always wanted more. I wanted to go somewhere. What’s different about long-distance kiting is that you leave from wherever you start, and you don’t go back. You kite down the coast some distance, you arrive somewhere else, sleep there, and then continue again the next day. While we often use vehicles for gear support and/or safety, it is possible to travel this way without getting into a vehicle for days, even weeks at a time. The detachment from the world of roads and vehicles and the immersion in the journey creates a totally different feeling.

Variations within long-distance kiting include supported, unsupported, solo, crossings, distance records, and exploration, just to name a few. All of these areas are seeing rapid development, and I think we will see more and more in the coming years. There is still a ton of unexplored territory and many “firsts” yet to be achieved in long-distance kiting. For inspiration check out Louis Tapper’s original 2000km solo trip, the solo longdistance trips that Andre Penna is doing on his foil in Brazil, the mega-distance records that athletes like Nick Levi are putting up, the multiple world records set by the amazing Bridge family at the Isle of Wight, or the 600km “Ironman” trip” that I did last year.


The most common type of long distance kitesurfing is done with the support of vehicles that travel along the route by land, carrying all of your regular-life stuff (most of which you quickly realize you don’t really need at all). It’s not usually necessary, but in certain conditions a boat or PWC is needed for on-the-water support. On the other hand, given the right conditions (first of all: warm air and warm water) long distance kiting can be done entirely unsupported, with just a waterproof backpack and some cash in your board shorts.

The north-east coast of Brazil is particularly well-suited for long distance kitesurfing, with hundreds of miles of sandy beaches, side-onshore trade winds, warm water, warm air, great food, great culture, and an absolutely incredible landscape – but there are many other places around the world where distance trips can be done, most of them undeveloped. Where? That’s part of what’s so cool about long-distance – most of it remains to be discovered!

Long distance equipment
Long distance equipment


Although some specialized gear is starting to emerge, long distance kiting can be done with just about any equipment. You can go long-distance on light wind race gear, wave kites and a surfboard, a twin tip – or perhaps best of all: a foil board.

When you select gear for a long-distance trip, the most important consideration is your skill and level of confidence with your gear. Choose gear that you have mastered – you want to be sure that you can make it work if the wind drops or if you need to go make landfall somewhere other than your planned destination. We’ll go over equipment in more detail in another article, but if you are doing a long distance trip in a warm place like Brazil, you really don’t need much beyond your board and your kite.

You also need to select equipment that is going to work well in the terrain and conditions that you’ll be riding in. My board preference is a strapless surfboard with relatively high volume and long rails. I use a 5’3” Firewire Vader – this board goes super fast on any point of sail, rips upwind, works well in both light wind and high wind, and is also relatively short, making it easy to travel with. I always ride strapless – you can use handles if you like, I just find that they get in the way of my feet!

When selecting kites, the most important criterion is that they are in excellent condition. I also recommend kites that have good range, especially if you are planning a solo trip. I fly the latest Boardriding Maui Cloud kites, and I love how versatile, nimble, and compact they are, but you can use just about any kite for your long distance journey.

Foil boards are opening a lot of doors for exploratory and long distance kiting. Foils require less physical effort for a skilled rider, and they allow you to cover ground in just about any direction, making it possible to plan long-distance routes that include upwind legs as well. The main issue with foils is that they require at least a meter or so of water depth. You absolutely do not want to crash your foil into anything hard – I’ve done it, it’s not fun, and it usually spells the end of your trip. Foils are also more likely to get tangled in flotsam or fishing nets, but that usually isn’t catastrophic. As long as you account for these factors, foils are an incredible tool for distance and for exploring. I love my Alpinefoil which, among other things, packs down very well for travel.

The Journey 

For me, the journey is what long distance kiting is all about. Whether you travel solo or as part of a supported group, down the coast or crossing from island to island like Mitu did recently in Cape Verde, there is very specific and unique feeling that you get from such a journey. Spending several days on the water, traveling entirely by kite and away from the world of cars and roads – away from the land for the most part, in fact, puts you in a unique state of mind.

You may be familiar with the idea of “Flow”. Flow is a state of mind and a state of being in your body. You find yourself in flow when you are totally absorbed in what you are doing. Your perception changes, and your intuition takes over from your conscious mind. It’s common to enter a flow state during intense physical activity, and it can happen for a few minutes or a few hours at a time.

Bowen in Brazil
Bowen in Brazil

The magic of a journey is that you extend the flow state beyond the immediate physical rush of action. You spend days immersed in the experience, in the feeling of your body working, and in the feeling of being part of the natural world. Being in Flow feels good – it’s recreational, but it’s also challenging, restorative and inspiring. Flow is also addictive – the more time you spend in Flow, the more you realize that other things – most things, really – are a distraction.

When people ask me about kitesurfing, I often describe it as a form of sailing, and as the combination of sailing and surfing. The essence of sailing is to make a journey by the power of the wind alone, to cast off from a known port and arrive on foreign shores. Long distance kitesurfing is how we as kitesurfers can experience this pure soul of the wind – a unique way to travel, to explore, and to expand your horizons in the sport. I encourage everyone to do some long distance kiting and feel how distance is different!

This post was originally published on SurfinSemFim

Swimming the Gate

I’ve been training all year to swim the Golden Gate. It’s about the same distance on the map as the much more popular Alcatraz swim, but the currents in the Gate are even wilder – there’s simply no such thing as slack tide in this massive funnel where San Francisco Bay pours in and out of the Pacific every six hours. I finished dead last but only one of a few who swam in “skin” i.e. without a wetsuit, my time was still perfectly respectable, and I felt great throughout the swim and afterwards.

Ansel Adams, Golden Gate Before the Bridge (1932)
Ansel Adams, Golden Gate Before the Bridge (1932)

As a San Francisco native and lifelong denizen of our beautiful bay, swimming the Gate has been in my mind for some years. I put the idea off repeatedly, shelving it under “foreign concepts” and “unnecessary hardship”, but it persisted. This year I got the message again and finally had the courage to commit. I really don’t believe in putting things off, but it sure can be easy to do, especially when faced with a calling that requires truly new skills. There’s something else about swimming – it’s not fear, and it wasn’t just getting past the point where swimming was simply unpleasant because I wasn’t that good at it. Swimming requires a huge amount of head game.

This past Saturday morning was probably the most beautiful morning on San Francisco Bay yet this year: sunny, warm, and relatively calm. Absolutely perfect conditions and I had no fear, no anxiety. And yet during the swim I was constantly confronted with a voice saying “just call it, this is unnecessary, what are shu doing here, the current is pushing you the wrong way, what’s the point, there’s no need for this, why bother” even while another voice was simultaneously saying “wow, this is amazing, the water is perfect, I’m not tired, check out the view, no problem, you got this, it’s not even that far, this is amazing, no worries, have fun, you’re almost there”. I’ve experienced this before while climbing and perhaps I’ve just forgotten how that felt – or perhaps that’s why I stopped climbing. And I’ve experienced it more recently while paragliding, which almost made me stop flying. In both of those cases I can attribute a large portion of the feeling to the situation that those sports entail: halfway up a 1000’ cliff, or dangling in the middle of the sky from bits of fabric and string. While you might think being in the middle of SF Bay in nothing but your sunga is similar, I feel quite comfortable in the water, and so I’m left to face the truth directly. The truth is that it’s not the situation, and it’s not fear. It’s reluctance to sincerely accept a challenge of unknown dimensions. To not postpone, beg off, be distracted or unprepared, to not quit or fail. To not commit to try, but to simply say yes.

My dad said to me not long ago that he thinks I’ve had it easy. I think that’s bullshit. A lot of things have come fairly easily to me, and I give him credit for teaching me so many physical skills early on, which gave me a great deal of physical ability and self confidence. Swimming, however, has not come easily. It was hard to choose to do this, even though I wanted to. I don’t mean to make any more of this than it is – lots of people have swum the Gate, and for a decent swimmer it’s no big thing – but for me, this was a real accomplishment. And – I had an awesome time. Super fun to be able to do something like this and enjoy it!

2016 Golden Gate Bridge Swim - San Francisco, CA, USA
2016 Golden Gate Bridge Swim – San Francisco, CA, USA