Not many can say they’ve biked their city more than veteran bike messenger, Kevin “Squid” Bolger. The 42-year-old Queens native has been riding the streets of New York through injuries, urban hostility, and infrastructure changes for over two decades. Still, Squid shows no signs of hitting the brakes just yet. As founder of CycleHawk, his commitment to the industry and its prosperity is unquestionable. In Part Two of this Spoke &Word, Squid gives us a look inside CycleHawk, the messenger industry, his views on a changing NYC, and the road ahead.

  Photograph provided by  Takuya Sakamoto

Photograph provided by Takuya Sakamoto

Tell me about CycleHawk and what you are doing now.
I worked with a lot of big corporations and I realized I was always promoting other peoples’ brands. One day, it dawned on me to create my own, so I started CycleHawk in 2006. I wanted it to be a brand in the beginning. I was using it to promote my events. Then in 2007, I partnered up with a friend of mine (also in the messenging industry) and we started a messenger company called CycleHawk. We worked together up to 2011 until we split ways. He held on to the company and I just spread my wings and flew off by myself with a few clients. I’ve been doing different projects ever since. I still have my messenger clients, but I’m also currently working with a company called Zipments. It is a technology company which builds apps for couriers and courier companies. We’re creating a giant network of couriers that can work together to help each other, get deliveries done, and pay each other well. Basically, our goal is to make a better industry for individuals who work hard and on the street doing deliveries. 

How is the bike messenger industry doing now?
This industry has been through a lot of downsizing over the last 5-10 years. A lot of the work we do has gone to the internet. With the financial meltdown in 2008, a lot of companies and industries had to cut back on costs and stopped using messengers because it is kind of a leisure to have your stuff delivered within one to three hours. As a result, we lost a lot of business. When I started out, there were probably 3,000-4,000 bike messengers on the street in the early 90’s. Now, I’d say we’d be lucky to have 750 out here. A lot has changed, but there is renewed interest in same day delivery from the tech sector. A lot of big companies are focusing on what they call “last mile delivery.” There is a buzz about how companies can make deliveries faster than next day. All the big companies, like USPS, UPS, Fed Ex, are interested in making same day delivery something they can offer to keep up with vendors like Amazon and eBay. Right now, we’re riding a little wave of tech sector money which is pretty awesome.

How is this industry affected by season changes?
In the summertime, people are more likely to deliver their own packages because it’s nice outside. Everybody and their mom wants to be a bike messenger in the summer. It actually slows our business down.The winter is always the time of year to make the most money for a few reasons: the holidays, it’s cold, and people tend to stay in their offices and get more work done. Plus, there are less bike messengers because the majority of them don’t want to work in the horrible weather, which is totally understandable. However, a professional bike messenger is prepared for the worst weather and excited for those days because it is when you are going to be making the most money in your career.


What kind of person does it take to be a bike messenger?
Not necessarily a hard person, but someone with a sense of adventure, determined to succeed, and not going to give up easily. All kinds of people from different walks of life work as messengers. I know people who are very well educated coming from being doctors, lawyers, and engineers to becoming bike messenges because they want to ride and they want the physical aspects of it. I know a few bike messengers in their 70’s who are out there doing it because it makes them feel alive. There are a lot of students doing it part-time. There are also messengers who have just got out of jail. A bike messenger is one of the few jobs you can just walk-in and get hired. Some of the big companies get bonuses from the city and state for hiring work release people. Some people do it because it’s the only job they can get and others do it because it’s the only kind of job that gives them that physical aspect. NYC is such an incredible place to be on a daily basis. It keeps your interest pretty easily. 

Bike messengers have a bad reputation to some people, considering them careless and a danger to pedestrians and drivers. What do you say to that?
I haven’t experienced that myself. Maybe because I’m just a half-glass half-full type of person. With every individual, you have to take them on their own merit. Bike messengers have kind of a wild reputation, but from my experience - they are very friendly people and more often likely to help someone on the street than to hurt them. Running over someone’s foot might not be a great thing for that person who got their foot ran over, but it’s part of the game sometimes. If you don’t do it in a malicious way, then maybe you are teaching that person to be lighter on their feet and they won’t get ran over next time.

Since riding a bike is obviously part of the job, does it take away the joy out of riding for fun or leisure?
No, not really. I have two kids now, so I don’t ride for leisure like I used to. I still enjoy it and it’s still my favorite mode of transportation. I feel so comfortable on a bicycle. Less than a year ago, my wife and I finally broke down and got a car. It feels so strange for me to be driving. Now that I’m riding a little bit less, it does feel strange. I definitely prefer a bicycle.

  Photograph provided by  Takuya Sakamoto

Photograph provided by Takuya Sakamoto

Where is your favorite place to ride?
It’s a mixture between riding in Brooklyn and Manhattan. Brooklyn has more trees, longer easier rides, and less dense. Manhattan is more exciting and concrete. I know the layout really well, so it’s more of a video game type of rush in the city. Then again, I really enjoy riding my bike wherever I’m at. I’m lucky enough to have been around the world on my bike, so I had some great adventures. 

With bikeable international cities like Amsterdam and Copenhagen, how do you feel about NYC falling into this category?
I’ve been to Amsterdam and Copenhagen. It’s amazing and almost scary to ride over there. The commuters are so in control and travel so well together that if you pull over in a bike lane - people will let you know pretty quick to get out of the way. I’m happy that New York is heading in that direction. I’m also happy I was on the bike in New York before it started to happen. I got to experience the chaos years and now we’re moving into this bike utopia type of pontential scenario. It’s going to be great for my kids, as well as the health and well-being of all human beings. It’s a great and exciting thing to see. It’s, also, a little sad because it has taken away a bit of the gritty hard part of New York City I’m used to growing up in.

Where do you think NYC needs the most improvement?
New York is doing great and it really is changing fast. It’s amazing with all the public pedestrian plazas, the bike lanes, and Broadway being reduced to one-lane for traffic in a lot of places. However, if we could fix or make it better - the 1st thing that pops in my mind is that there are just too many cars. The parking on the steet is insane and they are always double-parked. Maybe there could be some way to reduce traffic? I don’t know if tolls are the answer to keep people from driving so much or making it illegal to have single occupant cars driven in the city. Something like that.

What is Cyclehawk doing to help improve biking in New York and keep the messenger industry alive?
I’m very involved with the New York Bike Messenger Foundation with 501(c)(3), where we assist couriers when they get hurt. CycleHawk presents an event once a year called Velocity Tour, where we throw a couple of races at the racetrack in Queens. Then, we’ll send the fastest messengers around the world to the Cycle Messenger World Championships. I’m also involved with a lot of urban cycling brands like Continental Tires, Kryptonite locks, Bern helmets, and Chrome bags. Since I started, there has been a new brand called Urban Bike. It’s like a new generation in Urban Sports. It has come out because of more and more people riding bikes in the states, so luckily I’ve been part of that wave. It’s great. We’re promoting a healthy alternative to not riding a bike. Promoting helmets is always a good message for kids by saying “Hey, it doesn’t hurt to wear a helmet.” It’s fun working with all these companies that are pumped on bike messengers because bike messengers are hardcore and they’re out there all the time. 

Are you ever worried about the day when bike messengers may no longer be needed?
Not in New York. There is always going to be a need. One of my big clients is a wine store. Until they can figure out a way to email a bottle of wine - they’re going to need someone to deliver that stuff. Luckily with New York’s crush of humanity, there is always going to be bike messengers here.

Any signs of slowing down? How much further do you think you can keep going?
I got a few more winters in me. I haven’t been going full-time for a few months now. But when it gets down and dirty out there and there is snow on the ground, that’s when I have to jump out because things start happening and people can’t make it in. I feel confident I could still ride hardcore at least until I’m 50 or 60. I don’t know I haven’t really put too much thought into it.

  Photograph provided by  Takuya Sakamoto

Photograph provided by Takuya Sakamoto

Will it be a sad day when you put away the bike?
No. I’ve been living on my bike for more than 20 years. I’m actually enjoying not riding full-time right now because it has given me a little breather and some perspective. I definitely feel happy with the time I put in. I’m passed the point where I have to be faster and better than anyone else, so that’s a nice feeling. I’m almost turning into a commuter at this point [laughs].


Not many can say they’ve biked their city more than veteran bike messenger, Kevin “Squid” Bolger. The 42-year-old Queens native has been riding the streets of New York through injuries, urban hostility, and infrastructure changes for over two decades. Still, Squid shows no signs of hitting the brakes just yet. As founder of CycleHawk, his commitment to the industry and its prosperity is unquestionable. In Part One of this Spoke & Word, I sat down with Squid to learn more on how he got started, the origins of his nickname, and the bike scene (then & now).

  Photograph by  Amy Bolger

Photograph by Amy Bolger

When did you get started? 
I started full-time as a New York bike messenger in 1992. I’ve been doing that straight for pretty much since then. Just over 20 years now.

What made you decide to get into this industry?
I didn’t want go to college when I got out of high school. I just wanted to get out into the world and stop looking at books. I was bouncing around to different odd jobs. My brother worked as a messenger for awhile. When he broke his thumb, he left all his gear at my mom’s garage: a bike, a bag, and a lock. I just figured why not try it out. It couldn’t be worse than what I was doing at time, which was being a security guard. Luckily for me, I fell right in with a really cool messenger company. It just made me fall in love with the job.

What is the story behind your nickname “Squid”?
To tell you the truth, there is no deep meaning behind my nickname. When I was younger, I worked at a bar in Long Beach and I was called “Squid” by a crazy bartender there. Kevin is a pretty common Irish name, so the 1st company I worked at already had two Kevin’s there. So they were like “Look, you can’t be Kevin! Do you have any nicknames?” And Squid just stuck.

What kind of bike do YOU ride? And why?
Here in the city, I’m usually riding one of these very minimal fixed-gear bikes. It’s just a very easy bike to upkeep. In the winter time, especially, you don’t have to worry about your derailleur freezing over or brake cable snapping from the cold. It’s a very utilitarian type of bike; as long as you keep air in the tires and some oil on the chain then you’re really good to go nine times out of ten.

Photograph provided by Takuya Sakamoto

Is that why a lot of bike messengers use a fixed-gear?
Yeah, I guess that’s the main reason why they became popular in the 80’s. In the winter, after you are out there working hard in the cold and wet weather all day - you are exhausted at the end of the day. Who is going to spend a half-hour tuning their bike up and wiping all the grime and salt off it? So if you do have a mountain or road bike - then your bike falls into disrepair very quickly or you end up spending a lot of time upkeeping it. A fixed-gear is just an easy bike to maintain. There aren’t many hills here, so it’s a practical bike. You don’t really need ten speeds to ride in NYC.

With your experience, I’m sure street-riding is a walk in the park. How is the way you ride and see the street differ than an average commuter?
I look at it from a whole perspective. I like to know what’s going on the sidewalks on both sides of the street, what’s going on the entire street, what’s going on the next intersection in front me, and even the one in front of that. I’m basically trying to take everything into account. I don’t consider a bike lane where I’m supposed to be. I consider it as one of my choices.  Of course, I’m always sensitive to pedestrians, especially the elderly and children. I imagine a bike commuter might be a little more focused upon the bike lane and just their very immediate surroundings.

What do you think makes NYC such a unique place to bike?
In the past, I sometimes felt that Manhattan was partially built for bicycle adventure. It’s just the way the avenues and streets flow. You can really be the fastest thing out there. Cars can only get up to an average of about 30 mph speed. I’d say most of the time they’re going slower than that - even less than 20 mph with traffic and congestion. On a bicycle, you can hit 20-30 mph for miles at a time if you have the experience on the streets and catch all the lights. It’s a great feeling to know you are the fastest thing out there.

I’m sure you get asked this question a lot, but people are curious to know. What was it like biking in NYC in the early 90’s?
The early 90’s were very exciting. Very hardcore! The city was still suffering from the crack epidemic at the time; it was pretty wild on the streets. There were no bike lanes or infrastructure, so if you were out there on a bike - you really had to make your space. You had to fight for it a lot of times.

What were some of the other challenges bike messengers faced in the 90’s?
It was a bit wilder back then and the winters were a lot harsher. A lot of messengers died when I was working in the 90’s, especially in the winter time. People weren’t considering bikes and heavy snowfall. They would plow the middle of the street, so all the snow and ice would end up in the areas where bikes are most likely to ride. You had to deal with all kinds of stuff - locking your bike up, people with drug addiction problems looking to strip anything off your bike for ten bucks, and petty theft. It was a more violent city back then. It seemed people were more ready to lash out with their vehicles and make fights. 

How is the bike scene now?
I’d like to think that we’ve helped make bikes become an accepted form of transportation. Now, it’s a safer and easier place for people to ride. We are in the Age of the Commuter. When I started out, the scene was more the Age of the Gladiator.

The Age of the Gladiator sounds like an intense and dangerous time. Any serious accidents throughout these years?
A lot of close-calls for me. I’ve been in the hospital a few times. I, also, had a number of head injuries. I put my head through the front windshield of a car one time. That’s when I started wearing a helmet. That was in 2005. I got two kids now, so I don’t want to be a vegetable. As the years go by, you learn that it’s as dangerous out there as you are. If you don’t want to be dangerous, it’s up to you.

Did you ever think about calling it quits? How have you managed to keep doing this profession for so long?
I’ve never thought about calling it quits. Maybe it’s because I have a thick skull. It doesn’t feel like a job to me in a lot ways. I really enjoy the perks of being outside and just being part of the fabric of this incredible city. It’s always been such a rush and I’ve always felt so proud to say I was a bike messenger. I’m always going to be related to it in some way I think. Even now that I’m not riding full-time anymore…I’m very involved in our non-profits, the New York Bike Messenger Foundation, and also just making sure the industry is going to prosper - if I can have some positive impact on that.