A lot of people ask me about cycling in NYC. They ask me about startups, too. As I was biking around the other day, I realized that they have a lot in common and so the advice I have to give about both is pretty similar:
1. Cycling is a *higher* risk activity, but it doesn't have to be dangerous.
If you're going to start a company instead of working for someone else, you're definitely putting something at risk--current income, opportunity cost, some social capital perhaps. That being said, it doesn't mean you're going to wind up homeless if things at your startup don't work out. Failure of a startup doesn't mean failure of your career by any stretch--so long as you treat people with respect and honesty, and you work hard.
2. Taking some amount of additional risk can make for a better overall outcome--because biking in bike lanes all the time is boring and may not even be that much safer.
If you're going to put it all out there in a startup, bite off something that you're not 100% sure will work out, but that, if it did, would make a significant impact. If you have zero chance of failure, you really didn't challenge yourself--and you might actually be more successful if you attempt something harder that is worth doing. That will inspire others to join and help.
3. Pay attention to traffic patterns--buses only pull over at bus stops, taxis will dart back into the street after a dropoff, etc.
Pattern matching is one of the most useful skills out there as an entrepreneur. How do users generally behave around your value proposition? What has worked in other startups? Why? What hasn't worked? If you can't learn from the patterns of history, you're going to get flattened.
4. Big trucks are slow to accelerate--you can always beat them out when they're moving from a standing stop.
What if Google does this? Well, they could, but you have to believe that you'll do it better, faster, cheaper. They could do anything but you have the advantage of already being in the flow of the market. By the time a big company gets its act together, you'll be free and clear.
5. The things that will get you aren't what you expect--it's not the cars, but potholes and pedestrians.
Startups are all about being prepared for anything--knowing where you're heading, but being nimble at the last second when something comes up that could wipe you out at the wrong moment.
6. There is absolutely nothing you can do when a car door swings open right in front of you except brace for impact.
Staying alive is the name of the game in a startup--and you're going to have plenty of near death experiences along the way. Know they will happen, and that you won't see them coming. Just hold on tight and weather the storm.
7. There's no such thing as the "best bike". There's only the best bike for you.
There are lots of goals people have when they start a company. Some people want to see their ideas win. Others want to make a ton of money. Other people just like the challenge. Just because another company does things a certain way doesn't mean they're necessarily right for you.
8. You need a good lock.
Don't get obsessed with competition, but know what the alternatives do well so you know how you can be better. Sometimes you'll win, sometimes you'll lose, but you don't want to lose on a feature that you could have easily built which is what your competition ate your lunch with.
9. You must wear a helmet.
Put all the right legal documents in place--co-founder agreements, privacy policies, etc.
10. Get some bright lights and reflectors.
Learn how to market yourself and what you're doing, both personally and as a business. You won't have a ton of money to put towards marketing, so understanding PR and ways of building up awareness about your efforts through social media are really important to get noticed.
Safe biking! (and startupping!)