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In July I biked from Porto to Portimao, Portugal, where I attended a friend’s wedding. This Saturday I began writing a recap/how-to along the lines of my John Muir Trail post. I sketched out a few notes and found that beneath my trip recommendations was a foundation of cycling experience, the sort of foundation that allows trips like these to be super fun instead of horribly stressful. With that in mind I’ve decided to write a series of posts on cycling starting from the beginning: buying your first bike*.

My first bike was determined to kill me. It was a mid-80s road bike that my dad dug up from his basement and threw in the car as we left for my sophomore year of college. I can’t find any pictures of it but when I say “mid-80s road bike”, please don’t take that to mean some kind of amazing neon fun machine. No, this thing was a ’96 Taurus in bike form. Not even fun as a one day rental.

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Nope, nothing like this.

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There we go. FYI - Humans paid money for these at one point. 

In addition to the bike’s regular mechanical errors (dropping chain, rubbing brakes, general shitiness) at the time I was also in the habit of getting very drunk and biking home the long way, which may or may not have affected the number of times I went down – hard to say really. Anyway, the important lesson from my first bike was: don’t choose a beat-up bike unless you’re a very good bike mechanic**.

Despite my POS bike trying time and again to toss me into oncoming traffic, I survived and in the process found biking to be the only activity keeping my sane in NY. I rode every day and needed to upgrade to a mostly-functional bike so I started observing what other people were riding and asking my cyclist friends for recommendations. Most people were riding fixies or single speeds. My friends recommended a single speed. I tried both and though I had a ton of fun on the fixies, I found single speeds to be a more pleasant day-in day-out ride. Knowing that I wanted a single-speed accelerated the buying process because I didn’t have to worry about finding the right components, which I’ll write about later in a “buying a road bike” post. The lesson from researching my first bike was: trust your friends + local cyclists when choosing what type of bike to buy.

Once you know what kind of bike you want, you should figure out your size. To do that you’ll need about ten minutes and access to a few bikes. I’d recommend finding a plain old bike shop with nice employees who won’t hard sell you on bikes or worse, $150 fitting sessions. I like Tip-Top in my neighborhood, Sports Basement in SF, and when I lived in NYC Landmark was pretty good. If you’re in the middle of a size range, I’d recommend going for the smaller size–it’ll handle better.

Next you’ll want to determine a budget, which is difficult because you don’t really know what anything should cost. Here are a few lessons I’ve picked up while buying bikes:

  • Your goal with a first bike should be to get comfortable riding and have a ton of fun. Expensive and/or finicky bikes work against that goal so…
  • Do not, under any circumstance, buy a fancy new bike for you first bike. If you don’t use it enough you’ll kick yourself then eat a loss when you sell it. If you do use it and something happens - it’s scratched or stolen - you’ll also kick yourself.
  • You’re better off buying a bike that’s cheap but ultimately not good enough for you then selling it to a beginner in the same position as you when you bought it, thereby not taking a big loss if any.
  • Single speeds/fixies from most brands don’t depreciate so it may be easier to buy new. 
  • Single speeds/fixies from fancy brands do depreciate so always buy these used. Unless you’re spending lots of cash on a super nice track bike, expect these bikes to perform almost identically to average single speeds - they just look pretty.
  • Depending on the city, Craigslist may have some good deals if you’re patient. 
  • In my experience the best Craigslist deals happen in wealthy commuter areas where people will spend lots of cash on fancy bikes, never ride them, and then not care about selling them at a major loss. There’s also significantly less competition to get those bikes because you’ll have to schlep out there, which most people won’t do. For example, the two bikes I’ve purchased since moving to the Bay Area were in El Cerrito and Santa Rosa, not SF.
  • If you want to try Craigslist and know the brand you’re looking for, use this IFTTT recipe to alert you when new CL posts match your search terms, then be prepared to buy the bike on the day it’s posted. Good deals tend to move quickly and CL sellers don’t care that you really want it – they’re going to sell it to the first person who shows up with cash, always.

What I did for my first bike: I spent $279 for this track bike on Bikes Direct and another $40 on a front brake so I could ride it as a single speed. I’d make the same choice 100 times over. I’ve put thousands of miles on that bike and love it. Bikes Direct ships you the bike mostly complete so you’ll be able to put it together yourself or have a shop finish the job for fairly cheap.

A note on bike theft: If you plan on locking your bike up outside and can’t afford to have it stolen, I would recommend buying a cheaper bike that you can afford to lose. I’ve had several friends buy nice bikes then stress out whenever they can’t bring the bike inside so they end up riding less, which defeats the purpose of owning a bike. When you do lock up, always lock the back tire. It’s significantly more valuable than your front tire. I’ve used this lock and cable for a few years and like it though the provided bracket isn’t great.

And a note on bike damage: I once heard someone say, “you can’t enjoy your Aston Martin until you scratch it,” which is both amazingly douchey and absolutely true. You will eventually scratch and/or dent and/or generally mess up your bike. Don’t worry about it and go have fun.

I hope this post helps you find and buy your first bike with confidence. Feel free to send me an email if you have more questions.

Next up in this series is “Buying Your First Road Bike” followed by “Determining Your Ideal Pastry to Face Ratio.”


*First grownup bike.

**On average, people buying a bike for the first time aren’t very good bike mechanics.

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Last August I hiked the John Muir Trail in eight days. Since finishing the trip I’ve fielded a bunch of email from friends and friends of friends as they plan their own hikes. I tend to offer the same advice to each person so I’ve decided to throw it all into a blog post.

First off, congratulations on planning at all. You’re much smarter than I am. I decided to do the trail less than two weeks before starting so my “planning” was essentially a Super Toy Run through REI.

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^^Less fun when you’re footing the bill.^^

But really, well done. If you prep correctly for the hike it should be a breeze. To make this less daunting I’ve separated my tips into three categories: logistics, gear, and hiking.

1. Logistics

The JMT is 210 miles long but hiking 210 miles from Yosemite Valley will put you squarely on top of Mt. Whitney so you’re actually going to hike 220 miles - surprise! The total elevation change is around 84k feet with seven passes topping 11k feet. The passes near Mt. Whitney are closer together so you’ll knock out more elevation per day at the tail end of your hike, assuming you start in Yosemite.

Most people I met along the trail were taking 18-25 days to complete the trip. If you can get that much time off and don’t consider punishing yourself with 25+ mile days relaxing, I think hiking the JMT in 18-20 days would make for a swell few weeks.

If on the other hand you’re like me and have a perpetual desire to prove your legitimacy despite the fact that nobody really notices or cares, then I encourage you to go for the sub-10 day version. I did it and felt slightly cooler for about one week.

The first thing to consider is your permit. 60% are available online 24 weeks in advance and 40% are available for walk-ins. I obviously went with the latter option. Keep in mind that it’s common for people to start lining up outside the Yosemite Valley permit office at 4AM. Also keep in mind that you can’t sleep overnight in front of the permit office because that’s considered camping out of bounds for which you’ll be socked with a large fine–and if you’re caught “camping” there with food you’ll earn a bonus fine for not storing it in a bear box. Sweet.

It’s important to be at the front of the line for two reasons. 1. You’ll get a permit - dur. 2. You’ll get the right kind of permit.

There are two kinds of permit: the one you want will allow you to go any distance on the first day, the other will force you to camp at Little Yosemite Valley, which is just four miles from the JMT trailhead and makes for an awkwardly short first day. The number of available permits fluctuates based on reservations and cancellations. Once you snag a wilderness permit you’ll be able to stay in the backpacker’s camp for one night and prep for your trip.

After deciding how you’ll get a permit you should determine a resupply strategy. I did two resupplies: Red’s Meadow and Muir Trail Ranch. Be sure to ship your bucket to Muir Trail Ranch early because they pick up mail infrequently. Muir Trail Ranch is the last convenient resupply point so people often send a huge cache there. More often than not people ship themselves more food than they can pack out so they have to ditch it at the Ranch. In other words, it’s likely you’ll be able to collect extra food or toiletries if you’re short.

Your last logistics obstacle is figuring out how you’ll get back to your car in Yosemite from Mt. Whitney. Most people arrange a shuttle or bum a ride from the trailhead, Whitney Portal, to Lone Pine where they spend one night. The following morning they take Eastern Sierra Transit from Lone Pine to Lee Vining followed by a YART from Lee Vining to Yosemite Valley. If this sounds super annoying you’re right, it is.

My return trip had the Rim Fire as an added ingredient. With roads shut down and YARTs cancelled, I joined a group in Lone Pine that hitchhiked from Lee Vining to Olmsted Point and then hiked an extra 10 miles to finally reach Yosemite Valley. The experience was actually super fun.

This concludes the boring logistics section.

2. Gear

In my opinion gear conversations devolve into bikeshedding almost immediately so I’ll just lay out my broad thoughts on the subject then share what I used, liked, and didn’t like.

A. It’s easy to be penny wise, pound foolish. Spend any amount of time on backpacking forums and you’re bound to run into a hiker sawing her toothbrush in half and ripping straps off her pack to save a few grams. Even better is the dude spending $300 more on a tent because it’s 3oz lighter than the alternative. Yes, weight is cumulative and less weight is better but you might be wasting time and money counting grams while overlooking pounds you could drop for free.

Here’s an example: a liter of water weighs 2.2 pounds. Maybe it’s time to reconsider filling the 3L bladder and just collect water more frequently.

Taking a step back from gear entirely, don’t wait until you hit the trail to start losing that belly. Your knees don’t know the difference between 10 pounds on you vs your pack.

B. Test, test, test. Bringing new gear on a big trip is a surefire way to stress yourself out. Even if it doesn’t fail, trying to figure out how a stove pump or tent pole works in the pouring rain is not fun.

C. Buy the good stuff the first time. To clarify, that doesn’t mean buy the most expensive tent you can find. It means skip the entry-level products because you’ll end up replacing them - usually within a year of use - and they’ll have no resale value. I made this mistake when I started backpacking and spent hundreds on gear I no longer use. In my experience, you usually fare pretty well with the most popular mid-level option.

D. Warranties are nice but won’t help if your gear fails on the trail. Look at your friends’ kits to find the stuff that’s been beaten up and still lasted years; buy those things.

E. Borrow from friends. People love knowing their gear is being used. If you have an outdoorsy friend group you can probably put a whole kit together - clothes and all - without spending a dime.

While I’m at it, I’ll say that if we’re friends and you ever want to borrow some of my stuff, just let me know.

Speaking of my gear, here’s a spreadsheet of what I used. I’ve included alternatives for the things that I didn’t like. Below are highlights:

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Altra Lone Peak 1.5 - Keeping your feet in top condition should be your top priority. I made the mistake of hiking in Merrell Trail Gloves and they were a disaster from day one. Blisters led to an altered gait that brought on terrible knee pain, all of which slowed me down. Since hiking the JMT I’ve put a few hundred miles on the Altras and love them. Ditch your boots and use these on every hike without snow.

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Black Diamond Trekking Poles - Hiking with poles will help you go faster, be more sure-footed, and encounter fewer injuries. You’ll also take some pack weight off your shoulders, which will keep you hiking longer. I’m so committed to poles that I trail run with them now. If you aren’t using them you should.

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Fuji X100 - While I wouldn’t call this a necessity, I will say that relying on your phone to capture the sunrise at Thousand Island Lake or the stars above Kings Canyon is a bad idea. Of the mirrorless cameras I’ve tried, the X100 takes the best photos and is the most fun to use. If you’re in the market you’ll see there’s a newer model, the X100S. For my money a used X100 is a much better value at $600 vs $1200 for the X100S.

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Therm-a-Rest NeoAir XTherm Sleeping Pad - Holy cow. For the longest time I camped without a sleeping pad because I thought they were useless weight. Turns out I had a junk sleeping pad. Not only will this improve the quality of your sleep, it’ll keep you substantially warmer at night because it retains heat your body would normally lose to the ground.

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Patagonia Nano Puff - Awesome. This is an essential item for me on any trip. Put it under a shell and you’re good well below freezing. It also makes for a decent pillow when stuffed into its pocket. Grade A nerd gear.

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Leukotape -  Another necessity on every trip. It’s ultra-sticky athletic tape with Zinc Oxide, which helps prevent skin irritation. Place some where you normally get blisters to prevent them from happening or use it to keep bandaids on when you’re sweating. I learned about this stuff when I was already on the trail and had to make due with the cheap tape I packed. It comes in large rolls so wrap what you need around an old plastic gift card and throw it in your kit.

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Probars - Stop eating Clif Bars and switch to these. They’re better tasting and better for you. I tend to prefer the flavors without chocolate but they’re all good.

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GU Brew Electrolyte Powder - Until hiking the JMT I thought these powders were BS. Turns out they aren’t. I’ve since tried every electrolyte powder at REI and find GU to be the best tasting. GU also makes a caffeinated version called Roctane, which is 3X more expensive though I don’t find it to be 2X let alone 3X more effective. Lemon Lime is my flavor of choice.

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You may have noticed in the spreadsheet that I didn’t mention a stove or cooking gear–that’s because I didn’t bring any. I opted to pack four kinds of calorie-dense GORP and not worry about cooking and cleaning every night. It worked out OK. If I were to do it again, I’d consider bringing my Snow Peak Gigapower stove to make warm drinks and the occasional bag meal at dinnertime.

3. Hiking

It’s all in your head. Seriously, it’s all in your head. Ok, most of it is in your head.

Telling yourself - and believing - you’ll complete the miles that day essentially guarantees success. For me it was as simple as underlining my target campsite in the guidebook and going there. I never allowed for deviations, even when my knee was throbbing and I’d been hiking for 18 hours straight. Just pop an Aleve, eat some sugar, and keep rolling.

One thing I quickly learned on the trail was that thunderstorms pose a risk not only to your safety but to your ability to knock out big miles. Crossing an 11k ft pass during a thunderstorm is neither smart nor fun. What’s more, once you leave tree line at 8-9k ft you’re exposed to risk. That means to cross a pass safely - leave tree line, go up, over the pass, and down back into the trees - you need to spot a thunderstorm hours in advance. The problem is thunderstorms roll in fast - usually with less than an hour’s notice - so what do you do?

My strategy was to wake up early - around 4AM - and check off the day’s passes before the early afternoon, when thunderstorms are most common. To do this you need to be smart about where you camp. In other words, you don’t want to camp at the bottom of a valley–in the Sierra the valleys are actually entire watersheds. You’ll want to push on and camp at altitude, making your first pass the following morning much easier. Completing a pass within a couple hours of beginning each day always provided a nice morale boost.

The other time consideration is in regard to picking up your resupplies. If I remember correctly, Red’s Meadow is open from 7AM to 7PM and Muir Trail Ranch is open from 8AM to 5PM. Make sure to double check those times and if you’re planning to cut it close, maybe arriving at Muir Trail Ranch at 4:45, don’t. You can easily be delayed on the trail and waiting overnight for a resupply is an avoidable annoyance.

In terms of campsite locations, my only advice is to go where your miles and passes dictate. Some sites are more beautiful than others but at the end of the day you’re hiking the JMT and they’re all pretty awesome. If you’re going to arrive at camp late and leave early, try to find a spot away from other hikers. Backpackers are a pretty laid-back bunch until you wake them up with your headlight and camp noise at 4AM–trust me on this.

Regarding animals, I didn’t see anything large or dangerous. I did meet a couple dudes who had a bear take their food in Lyell Canyon but they weren’t using a canister so they kind of had it coming. My advice is to not be messy at camp and make noise while you’re hiking, especially at night. Occasionally knocking my poles together or on a nearby rock makes me feel like I’m deterring animals–who knows if it actually helps.

My last bits of advice are recommended goals: stay positive and avoid injuries. If you accomplish one, you’ll complete the trail. If you accomplish both, you’ll complete the trail and have a blast doing it.

Good luck on your trip and if you have questions just throw them in the comments as I’m sure many folks are wondering the same things.

2013 was fun. Here’s a big handful of things that started to make more sense over the past twelve months.

1. Living through an experience is the only way to understand it. 

My bad for undermining the entire post on the first point but I’m pretty sure this is a truth.

Before I moved to SF last January I thought it was 100% candy canes and gumdrops: tech everywhere and killer outdoors access. People told me there were downsides and though I understood the logic of their points I refused to really believe them. Turns out they were right. SF’s pretty good though.

2. Criticizing other people and their projects is a waste of time.

If something makes people happy, it’s great. Too often I find myself making fun of people that like to dress up as though they’re seasoned alpinists when in reality hiking to the Tourist Club (super rad, you should go) is the upper threshold of their experience. Total waste of time - your time and energy are both fixed resources - plus the aspiration towards becoming a serious outdoorsman in particular keeps stellar companies like Patagonia in business.

3. Figuring out what you really want is hard though essential to your own growth and happiness. Letting other people tell you what you want is easy and won’t encourage growth or happiness.

When I lived in NYC I didn’t feel this quite as much but in SF where nearly everyone works in tech I’ve found it dangerously easy to mistake industry-defined success with what I actually want, which is, as always, more burritos.

4. You need way fewer things than you think.

I’ve spent the past 18 months with only four shirts and two pairs of pants. Almost everything I need, outside of outdoors gear, fits into a 36L backpack. The experience has been way easier and more satisfying than I expected it to be. Over the past few months I’ve begun to accumulate more stuff and dress more like a grownup but I’m trying to maintain the spirit of simplicity.

5. An untethered life is both totally awesome and totally not awesome.

I left NYC in the summer of ’12, moved to VT, then SF, then Oakland, then back to SF because BART != NYC MTA. Each step was so full of excitement that it took me a while to realize how the lack of a constant home was taking a toll on my happiness. As with my minimalist streak, my plan is to maintain a lighter version of this lifestyle going forward.

6. Physical activities are mostly mental.

In August I hiked the John Muir Trail in eight days. My prior single day max distance was 18 miles yet I managed to do 27+ miles per day for eight consecutive days. Realizing how much control you have over an experience through believing in an outcome was empowering.

7. Commitment increases satisfaction. Constantly trying to optimize decreases satisfaction.

This includes everything from where you live to where you work to where you get coffee to what you order at the coffee shop. It’s easy to make a simple decision way too complicated and waffle endlessly while everyone else is busy actually doing things. My advice: take a friend’s recommendation and if it sucks, don’t be friends with them. Reverse optimization strategy wins.

8. Don’t wait for external factors to align before doing something.

I’m totally a sucker for this kind of thinking. “If X works out, then I’ll really go heads down on Y.” Dumb. Just commit and do the thing or don’t worry about it at all.

9. Speaking at conferences makes attending them way better.

Hilary Mason was the first person I heard say this and she was totally right. As a more introverted guy, I don’t particularly like conferences. I find “networking” anxiety-inducing, awkward, and not all that fruitful. However, when you give a talk the people come to you! Plus they know what you’re about so they’re usually much more relevant.

Thanks to Chris and Cameron for giving me the opportunity to present at Brooklyn Beta and Brady for letting me give an Ignite talk, twice.

10. Schedules are good for you.

Keeping a schedule - especially when working from home - is massively helpful in both maintaining sanity and increasing your satisfaction with your work. Instead of focusing endlessly on shipping code - usually with diminishing value - I’ll block out a three hour chunk and when the time elapses, I’m done. Afterwards I can point at the slot and say, “this is what I did” and hopefully feel good about it.

11. NYC and SF are both cool places. Please everyone, stop trying to pick a winner.

NYC has more diversity and culture. SF has more nerds and nature. There. Done.

12. Every list should always have twelve extremely important items.

Just like this one.

Happy 2014 everybody!

If you want to put creative stuff online you have a ton of options. If you want to consume creative stuff online you have even more options. But what if you want to be creative online? And what if you’re not technical? The list shrinks quickly. I’m hashing out ways to solve this problem and I made a discovery at this past Comedy Hack Day that I’d like to share.

I’ll pause for a second to mention that after the first CHD I realized how few sites there were that encouraged playfulness. I mean this in two ways: playfulness in how a user interacts with a tool and playfulness in why a user interacts with a tool. Either quality could exist on its own within an app but I’m suggesting that both benefit from the other’s presence such that the whole is greater than the sum of its parts.

Playfulness in how a user interacts is pretty straightforward: the app is fun to use. The app takes common design patterns and fiddles with them just enough so as a user you experience a neat interaction then stop and think, “oh, that was nice. I want to do that again.” If you focus all here you’re in game territory and games are awesome but I’m interested in play as a creative and constructive exercise and games don’t always accomplish that.

I think baking playfulness into why a user interacts with a tool moves you closer to that creative, constructive online environment. Industries all have their own word for this playful construction - riffing, remixing, forking - but it’s in large part the same concept: you find a thing you think is cool and try to make it better then throw it back into the ring. A commitment to encouraging those constant permutations around a thing feels like an essential component of any future creative platform. What I discovered through the most recent CHD was that there might also be reason to encourage a level of remixing and modification above individual items of content.

Going into the most recent CHD I made a commitment to help at least one of the teams turn their hack into a more lasting and hopefully useful product after the weekend concluded. I decided to work with Matt Klinman to help him expand his project, Clickstrbait—a site that generates clickbait headlines and traps users in endless loops of annoying UpWorthy-esque overlays. Here’s his hilarious demo. After the event we decided to make a Chrome extension that functioned like AdBlock for clickbait. We call it BaitBlock and you can find it here.

It’s pretty simple. After you install the extension, head on over to Twitter where you’ll see small buttons injected into each tweet’s div. You can use those buttons to flag any tweet as clickbait, which will block it from your feed. Once a tweet passes a certain number of blocks globally it will be blocked from the feeds of everyone with the extension installed.

While demoing it among friends and then at Brooklyn Beta last Friday, I was happy to see that people had fun using it and wanted more. Their first question was invariably, “where else can I block stuff?” They wanted to modify the interfaces of their favorite sites and leave it for their friends to see. The notion resembles an odd sort of digital graffiti/geocaching that, to me, looks and feels like play.

I’ve yet to come to any hard conclusions as to how—or if—a more versatile modification tool would be useful, but it seems like engineering a way for a non-technical person to mod the web could be fun.

If you want to chat more about this stuff, shoot me an email.

Special thanks go to Kevin Foley and Jon Ferrer for helping out with Clickstrbait and BaitBlock, respectively.