Why We Started Ridejoy

I’ve been messing around with a site called Askolo, which allows you to ask questions of smart, interesting people like Alexis Ohanian (cofounder of Reddit), Mark Bao (creator of threewords.me) and Paul Graham (Y Combinator founder). It’s like the structure of Formspring with the content quality of Quora.

Here’s a question I was asked and then answered:

Q: What was your team’s inspiration for starting Ridejoy?

A: I’ll tell you a bit about our background because it shows what we’re trying to do with Ridejoy:

I met Kalvin in college while working on a nonprofit and later became roommates in San Francisco. We were living in a 3 bedroom and need to find a roommate, but didn’t just want a random stranger. We found our third roommate (and future cofounder) Randy via a site we had built called http://jasonandkalvin.com. After living together for a year and becoming good friends while working at separate startups, we felt the time was right to start something new and build something meaningful together.

We had shared passions around technology, travel and community and our backgrounds led us into rideshare. (Randy had relied numerous times on the kindness of strangers when backpacking through Europe and Asia to share food/housing/rides, Kalvin had recently experienced the unique private transportation networks of East Africa and I have a lot of great memories of long-distance roadtrips with friends: like driving down Route 1 (http://www.jasonshen.com/2011/road-trips-and-taking-the-long-way/)

Just as we used the web to find a roommate we could have a strong connection with, we’ve built Ridejoy to help people travel easily and affordably and with people they could share this great travel experience with. We were very fortunate to go through YC in the summer of 2011 and going to Burning Man (via our rideshare site http://burningmanrides.com) has certainly influenced our outlook on things as well.

We love the fact that this service helps people get where they need to go (usually to see family or friends or significant others) in a cost-effective way (the recession hurts!) while reducing CO2 emissions and creating real-life human connections.

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If  you liked this and want to ask me a question or read my answers to 14 other questions, check me out on Askolo.

Photo credit by stuckincustoms

I’m Teaching a Class on Skillshare

As the cofounder of a collaborative consumption startup, I do my best to try all kinds of “sharing economy” services like Couchsurfing, TaskRabbit, Airbnb, Vayable, Grubwithus and Skillshare. I even blogged about my experience taking a UX Design for Non-Designers Skillshare class.

But there’s of course generally two sides to these products – the consumer and the producer. In Couchsurfing, theres the host and the surfer. In Vayable there’s the guide and the explorer. And in Skillshare there is the student and the teacher. It’s important to get both perspectives when you can.

I’ve worked hard to avoid blogging about blogging here at The Art of Ass-Kicking. The vast majority of my posts are on overcoming your fears, doing great work and making epic sh*t happen.

At the same time, in building this blog up, I have learned some great lessons about creating compelling content, discovering my audience and attracting 100,000+ visits over 2011.

And I’m sharing what I’ve learned in a class.

Continue reading…

Launching always takes longer than you think (Guide to YC)

One lesson I’ve learned is that launching always takes longer than you think. If I got paid every time I heard a founder say their product was “two to three weeks away from launch” I could start angel investing.

Case in point: it’s been over a month since I said I was almost done with my cool YC-related project.

Well, better late than never is my motto. Last week I put up what I called the Unofficial Guidebook for Y Combinator Applicants at http://guidetoyc.com. In it, I shared everything I’ve learned from applying to Y Combinator, getting in, going through the program, understanding more about how the YC partners think and connecting with other founders.

I had friends who were applying to Y Combinator and asked for my advice so I would review their application. But I felt like most of my best advice was about how think about applying rather than specific feedback on their application. I wrote up a Google Doc on my thoughts on each section (team, idea, distribution, video, etc) and over the past few months have fleshed it out to what it is now – a 20,000 word guide on every aspect of the YC application process.

I put it up on Hacker News and in 24 hours got 6,500+ unique visitors spending over three-and-a-half minutes per visit. It was really great to know that people were digging my stuff.

After that, I worked closely with the awesome team at Hyperink, (a YC company that’s transforming publishing) and we were able to put together a beautifully laid out and carefully edited 92 page document that’s available as a free PDF download and also in mobi and epub versions in just 10 days.

It took longer than I expected – because I went through and re-edited several sections to make it as clear and readable as possible. I also integrated feedback from various YC partners who commented on the content. The Hyperink team did an amazing job turning things around quickly and professionally.

The result is something I’m proud to share with you.

Get your free copy of Guide to YC here.

I hope you enjoy the guide and I’d love to hear any feedback you have on the book. Please rest assured: regular blog posting will resume shortly.

Photo credit by Nils Öhman

Out of My Element: Notes by a Former Gymnast-turned-Runner in His First Triathlon


photo credit: Manuls via photopin cc

I’m always evolving and experimenting with my writing style here. On this post, I tried to write in the style of a magazine article, like something out of the Atlantic or Esquire. Not too pretentious, but a bit more literary than my standard ass-kicking fare. Let me know what you think in the comments!

I’m standing in a crowd of people covered in spandex and neoprene.

As a former gymnast, this is nothing new. Seeing muscled adult males squeezed in tight, form-fitting material was once a commonplace occurrence for me. What is novel, however, is that instead of being in a heated, insulated gymnasium, I’m standing in front of a dock, overlooking a small harbor on a chilly morning in early spring.

I’m here to compete in my first sprint triathlon.

For a long time, my only knowledge of triathlons was the Ironman ― the grueling 140.6 mile race that is one of the greatest endurance challenges in the world. It’s a 2.4 mile swim followed by a 112 mile bike ride, followed by a marathon (26.2 miles). As the story goes, the competition combined several long standing distance races to settle a debate between several military officers about which sport ― cycling, swimming or running ― was the “greatest”. The first Ironman Triathlon was held in Hawaii in 1978 and has since grown considerably in both participation and renown.

I found out about more manageable triathlons for mere mortals after following a blogger named Joel Runyon, who writes about triathlons [1], adventure travel and doing impossible things. More personally, I’ve been in touch with a college friend – a former swimmer who, in a renewed focus on exercise and weight loss, found a passion for running and decided to compete in a sprint triathlon.

The buzzer goes off and away we go, paddling through the water. I am surprised and pleased by the ability of my rented wet suit to keep the chilly 55 degree harbor water at a distance. The wet suit does not, however, do anything to prevent the salty sea water from entering my mouth every time I take a breath. Even after a month of swim practice at the YMCA, I find myself struggling to keep a good stroke rhythm going.

Halfway through swim I begin to feel my arms lock up as the coldness starts to affect their ability to move. I try to push onward, hoping that I won’t have to cry out for one of the lifeguards mounted on kayaks to save me from drowning pathetically 20 feet from dry land.

“What was I thinking”, I ask myself “when I decided to sign up for this?”

Triathlons come in four flavors: Sprint, Olympic, Half-Ironman and Ironman, each featuring longer and longer distances. For beginners, a “sprint tri” is relatively doable – with swim distances of 400-800 meters, bike rides of 10-12 miles and run distances of 3 miles or perhaps a 5k. While I personally find the term “Sprint” a bit puzzling as the descriptor for this distance, I can definitely see how it is a faster paced race than any of the longer distances.

How I found myself participating in a sprint tri has been a bit of a surprise and mystery to my friends and family. How does a gymnast of 16 years, used to meets where total time on equipment over six events adds up to less than 10 min of actual exercise decide he wants to race in hour-plus long triathlons?

It all started with a life-long shame in my ability to run.

Running has always been one of my weaknesses. I distinctly remember struggling to run a mile in gym class in middle school one year (the 27 laps around our gym’s hardwood floor feeling like an eternity) and my father chiding me for “losing to girls” with an 11 minute something mile. I was able to write it during my years as a competitive a gymnast, since one’s ability to run a mile has little to do with one’s ability to do a two and a half twisting somersault.

About a decade after that middle school mile, I was lost in the psychological wasteland of a former collegiate athlete. Going to the gym and working out felt empty and pointless. It was then that I tried running again. The first “real” mile I ran after college took 11 minutes and 47 seconds, which translates to 5 MPH, a speed reserved for driving in parking lots.

I am finally catching my breath.

I made it out of the water unassisted (2nd to last of the men in my batch) and am now riding the commuter/road bike hybrid I was borrowing from my roommate along the first of three flat lollipop loops that was the bike course. It’s a joy to inhale fresh air without a mixture of salt and the constriction of a suit.

I have, however, entered a new realm of hazards because while the swim portion was relatively contained with just a dozen or so men in my age group in the water, the bike route has men and women of all categories, including the highly competitive collegiate athletes. Sweaty bikers whizz by in gleaming blurs of carbon fiber and aero bars with a distinct zoom that sound more automotive in nature than pedal-powered.

I actually have to pull over to the curb as one fierce biker shouts for me to get out of her away. Did she say “on your left” or “move to the left”? I’ll never know.

Jason holding bike triathlon

A post-race shot of me and my borrowed commuter/road bike hybrid

Undeterred by my slow first run, and fueled by the keen desire to challenge and redeem myself, I began to put more miles on the road. My passion came not just from a need to conquer this weakness of my athletic ability, but of my skelo-muscular abilities as well.

I dislocated my left knee in my junior year of college in a disastrous vaulting accident and have undergone over five reconstructive surgeries to rebuild or trim my ACL, PCL and surrounding ligaments and tissues. Yet somehow running, especially in minimal footwear with a forefoot strike, has not given my knee issues and even my surgeon ― after examining my knee in an annual checkup ― grudgingly allowed me to continue running.

I was determined to turn running into a strength. And in the proceeding months, I did just that ― increasing my speed and distances from 5ks to 10ks to half marathons.

But after training for and competing in my first half marathon, I found myself suffering overuse issues in my feet that were frustrating and kept me off the road. And so looking around Active.com ― a website that lists sporting events and various types of races in one’s local area ― I found a sprint triathlon nearby held by my own alma mater.

I decided to enroll in the “Stanford Treeathlon“.

After getting passed endlessly for miles, I finally settle into a good pace and even catch myself passing a few people. I rip into an energy gel and drink a few gulps of water while trading “leads” with a boy who couldn’t have been older than 15. He’s even gracious enough to give me a “Good Job!” when I passed him. What a sport.

I try to kick it up a notch and attempt to chase down a girl in a white tank top. While I do pass her once, she catches back up and leaves me in the dust. Pulling in after my third loop I’m a little winded and my quads a bit sore, but otherwise feeling pretty good. I’m excited for “my” part of the tri ― the run.

The bike route gives a great view onto the sidewalk where I see triathletes stumbling away with terrible form, more shuffle than stride. I am excited to knock this leg out of the park.

It turned out training for a triathlon wasn’t very easy. The running was straightforward, but I don’t own a nice road bike, nor did my normal gym have pool access. I found a nearby YMCA and squeezed into lanes alongside senior and adult swimmers just looking to get in their morning dip. I suspect the lifeguards had a good laugh as I splashed away like a maniac, panting and half drowning as I put in my laps.

After swimming I’d get one of the spinning bikes and go for 20 or 30 minutes. Of course while those bikes are better at mimicking a real road bike, they don’t give you any digital feedback on distance or difficulty so I wasn’t sure how close this was to race conditions or even how hard I could push myself on the bike. My one cycling foray on actual road was a 12 mile round-trip ride across San Francisco out to the ocean that, with hills and traffic lights, took nearly 45 minutes each way.

I realized I did not really know how the race would go or how much it would tax me.

I struggle a bit to put on my Vibrams Five Fingers (my minimal running shoes that resemble “foot gloves”), my toes uncooperative and unwilling to slide into their proper spots. Eventually they’re wrestle them into position and I’m off.

Really off.

Everything feels wrong. My legs feel like they’re made out of lead. Shock from each footstrike resonate directly into my chest cavity and my heart feels like the clapper inside a church bell. Suddenly I realize why so many of those runners looked awful ― because they felt awful. I urge myself onward, slowing down my pace a little while I try to get my legs under me.

They come back about a mile in. Finally, I feel like I’m in my element. Foot in front of foot ― I’m moving. It’s pure sport, uncluttered by the brand of my suit, or the material of my frame. I hold an 8 minute a mile pace until I can almost see the finish line, then throw in my final kick, flying through the blue rubber mats that cover the timing machinery.

My total time clocks in a 1:29:40, putting me 2nd to last in the 25-29 year old male age group, and 154 overall, in perhaps 200 something competitors. My splits are 16:08 mins on swim, 43:20 on the bike and 23:28 mins on the run with 3+ minute transition times.

Jason racing sprint triathlon

The final sprint home!

Overall, I am happy with the outcome of my first sprint tri. In retrospect, I think I could have pushed myself a little harder on both the bike and run, though I definitely maxed out my swim. Some smarter racing tactics could have further shaved a few minutes off my time ― for instance my transitions could have been much faster.

There was definitely something exhilarating about running into the transition area, shucking a wetsuit or helmet and switching into new equipment. It felt like a being a Transformer (the phrase “activate running mode” seems like a catch phrase that could go on an ironic triathlete t-shirt).

I can also see the advantages of racing tri’s ― more variety in training and more room for optimization in a variety of area. Beyond just swimming, cycling and running more, improvements can come from learning a skill or technique (for instance, I could really benefit from swimming lessons) and simply buying just better gear. It almost reminds me of those casual Facebook-connected games where you can either earn your currency from in-game activities, or shortcut to them by converting your real money.

I personally don’t find all these areas of optimization very appealing. One of the few ways that gymnastics is similar to running is that the equipment is relatively standardized. While your home gym may differ from other gyms, at the competition, you are all wearing the same kind of spandex, the same wrist supports, hand grips and other attire and none of it guarantees a significant improvement in performance.

Similarly, in a running race, all that really matters is that you’ve got a decent pair of running shoes. Races feel more level and running feels more primal. Distance running feels like the ultimate competition, especially if you believe the claims by Christopher McDougall in his best-selling book Born to Run [2].

I’ll probably race another tri someday. Maybe I’ll even do the Treeathlon again, next year. I’m proud to have completed my first race and have a new level of respect for those Ironmen. But for now I think I’m going to stick with running. I’ve got a full marathon coming up in July and perhaps some fun races in between.

For once, I’m shying away from the shiny new thing, and pushing farther down simple, (but not easy!) road. I’d like to believe I’m doing things the way a real runner would.


FOOTNOTES

[1] In fact, he actually recently wrote an entire guide on sprint triathlons that you can check out here. [2] In the book, McDougall argues that the ability to run long distances is one of the distinguishing features of modern human beings and may have lead to hunting advantages over Neanderthals.