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 (https://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.


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

It is impossible to win the race unless you venture to run, impossible to win the victory unless you dare to battle.

– Richard M DeVos (via 50 Impossible Quotes)


I’ve had my hands pretty full recently and hope to get some more substantial posts out soon, but here’s a few quick updates:

  • YC Project:  I’ve been working on a cool Y Combinator related side project that’s almost done. I promise you guys will get a first crack at it when I release!
  • Ridejoy Funding: We announced some big news for Ridejoy: we raised $1.3M in seed funding from Freestyle Capital, SV Angel, Founder Collective and some other awesome people. Some coverage in AllThingsD, Techcrunch and Wall Street Journal.
  • How to woo a startup: Getting hired at a startup is tough. I know, I wrote a mega-post on it. That’s why I was super impressed with how Ridejoy’s new community manager applied (and got the gig). Learn more here.
  • Triathlon training: It’s going well. I struggled in the pool at first, and apparently gymnasts are notoriously bad at swimming, but I’m starting to figure it out. Doing a swim-bike brick tomorrow morning!

I don’t think most people on Wall Street are particularly moved by the protests of the #occupywallstreet movement. I think they feel that they have earned their wealth through hard work and intellectual horsepower. In general, high achieving people want to attribute their success to their skill, expertise and effort.

Daniel Kahnman reports in the New York Times about how again and again he’s seen people deny the implications of data against their intuition:

The illusion of skill is not only an individual aberration; it is deeply ingrained in the culture of the industry. Facts that challenge such basic assumptions — and thereby threaten people’s livelihood and self-esteem — are simply not absorbed. The mind does not digest them. This is particularly true of statistical studies of performance, which provide general facts that people will ignore if they conflict with their personal experience.

Bringing the discussion closer to home, there are many who compare doing a startup to playing poker. I’m not a big player myself but it appears true on a surface level: both involve many losers and a few big winners,  taking calculated risks, and strong elements of both luck and skill [1].

This is a long-winded way for me to follow up on my announcement of Ridejoy say that I feel incredibly lucky to be here. My startup Ridejoy just launched on Techcrunch, we graduated from the prestigious Y Combinator program and we’re now in a position to hire some great talent. It’s surreal.

I know my team and I have an enormous opportunity to make a dent in the universe [2] and I approach it with unbridled enthusiasm — tempered by the recognition that making good moves and busting your ass neither guarantees nor earns you a huge startup success.

I’ve put a lot into Ridejoy and I’m going to do everything I can to make it a success – and hope to share more of our story as it unfolds.

Ultimately we all have to recognize that we do not live in a just world. Luck has already played and will continue to play a huge role in the success of Ridejoy, and of any venture.

So those who have been given great opportunity have the responsibility to tackle it and work it to the maximum – and then use it to bring more opportunity to others.

Thanks for reading and for all your support.


[Photo Credit] Adriano Agulló

[1] Steven Levitt of Freakonomics Fame has published a working paper that suggests there is “strong evidence in support of the idea that poker is a game of skill.”

[2] Thanks Steve




I know it’s been over 4 months since I first posted about starting something new without really much word. I’ve gotten a fair number of inquires about it lately and I apologize for holding out on you for so long! [1] There were important reasons why I couldn’t blog more about it.

But the cat comes out the bag today.

I’m thrilled to introduce Ridejoy – a place to find new friends to share rides with. We’re a social transportation startup and we’re going to transform the way Americans get around. A more personal piece comes tomorrow, but let’s start with the TechCrunch story:

YC-Funded Ridejoy: Make Some Dough On Your Next Roadtrip (And Maybe Some New Friends)



[1] I recently got an email from a concerned reader asking about the status of my startup. He noticed that I hadn’t been posting much and was worried that maybe things were tanking and I had no one to turn to!

Fortunately that isn’t the case but I truly appreciated the note – it’s great to have thoughtful readers!