I own the Lezyne CNC Chain Rod, which I’m a big fan of (yes, I know I’m partial to Lezyne here–they’re a local-to-me, San Luis Obispo company and they sponsored my collegiate team, so I got tons of gear) and it costs right around $30. But the truth is that even the cheapest of chain whips will likely do the job. In fact, I’ve found a dude who knows his stuff and shows you how to make this tool all by yourself. I would even go so far as to say that you probably have enough materials laying about your garage (if not, try your parents’ garage ? ) to put this together without spending anything. Check out the video below:
As you mentioned, it is surprising how often you can get multiple flat tires on while riding, particularly on longer sprints. The tip about bringing a patch kit in your bike repair kit can be incredibly helpful if you’ve already had one flat tire. I agree that all you listed seems like an awful lot to carry, but it’s always better to be safe than sorry, isn’t it?
It has some useful information for basic repairs... not so heavy on the maintenance side but there is some in there. The pictures and drawings are in black and white, but mostly visible. Only a few are difficult to see. However, they are in 2-dimensions and they don't show you HOW to do the thing, they only show you the general area and the part you want to manipulate. The phrasing in the instructions can be hard to follow without a good visual reference unless you're already a master bike mechanic (which you aren't if you're thinking about buying this). So, buy this for general reference and rely on Youtube for video. The two together are better than either one alone.

Change and a $20 bill:   In case your cell phone’s battery dies, it’s nice to still be able to use a payphone if you need to.   Also, the $20 is a great thing to have in case you lose your wallet or have some other mishap.   I’d rather be able to sit in a coffee shop or fast food restaurant when it starts raining while I’m waiting for my friend or cab ride, and a hot cup of tea or coffee or the beverage of your choice and a snack makes it all the more pleasant.  Just try to remember, this is for emergencies, and if you use it, replace it ASAP!
In spite of seat bags’ diminutive size, a lot of people really, really want them to accommodate more stuff. If that’s you, the medium and large seat bag (but not the small) have an extendable gill at the bottom, which you can see in the image up top. It zips open to create more room. With it unzipped, we could cram a wallet, keys, and phone inside the medium as well.
Some years ago, I used to live on my bike. Riding around daily through any weather condition was bound to quickly wear down on the bike over time. I like some of the stuff that you have in your toolkit. I would say zip ties are actually really convenient, because when something came loose you could go ahead and use those to fasten them down to keep on moving ahead until you had enough time to fix it or get it checked at a bike repair shop.
Maintenance is the best prevention. “Prevention is the best medicine, and if you’re taking care of your equipment it’s super key. Bikes don’t just fail. If they’re in really good working condition and you clean them at night, and you’re religious about it, bikes are kind of like cars — they’ll start talking to you if something is getting worn or getting creaky or needs to be replaced.”

The Pedro’s lever slipped only once throughout testing, though that may have been my fault because I was spaced out after changing 16 different tires. So they’re not foolproof, but they are far and away more reliable than the next closest competitor, from Park Tool, because the small, rounded tip on that one is hard to keep seated under the tire. Not impossible, but I wouldn’t choose it over Pedro’s.
Next, two-stage designs. There are two types of hand pump. HV (high-volume) pumps, ones that pump a lot of air but don’t have a lot of pressure, which are used for mountain bikes. The Lezyne Alloy Drive is a high-volume pump. Then there are HP (high-pressure) pumps, which pump a small amount of air but can inflate to very high pressures and are used on road bikes. Our top pick is a high-pressure pump.
Brakes come in a variety of designs depending on the age and style of your bike. Rim brakes offer more modulation but have less stopping power, so are more suited to riding on the roads. Disc brakes can provide huge amounts of stopping power so are best suited to off road riding, although ‘V’ rim brakes are also well suited to mountain biking. All brakes use a friction system to stop the movement of the wheel, so regular checks of the contact pads should form part of your regular cycle maintenance.
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