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

Photo credit: Think different! by gianlucachiari via Flickr

Coming up with startup ideas is hard. Trust me, I know. Before my team and I settled on the current idea we’re working on, we spent many weeks brainstorming different things to do. Three different people with similar backgrounds can still produce a wide array of interests, skills and areas of expertise.

Here are some of the questions you might find useful when brainstorming your startup idea. They definitely helped us.

18 Questions To Ask When Brainstorming Startup Ideas

  • What do you love about your favorite products? How can you do that in a different way or for a new market / customer base / new use case.
  • What are problems you face in your life?
  • What are problems you see happening in other people’s lives?
  • What ought to exist in the world right now that doesn’t?
  • Are there obvious new behaviors that people will engage in 5-10 years from now? How can you build the technology to enable that behavior now?
  • Where are there groups of people who are struggling to do something where your product could make it much easier for them?
  • What kind of business would be really fun / exciting personally for you to build?
  • How can you take something that’s already pretty good and make it 5x better?
  • (10 more after the jump)
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