Andy Weissman on entrepreneurship, product development and the future of the Internet

Andy Weissman is a partner at Union Square Ventures and one of my favorite people in the startup world. He was a co-founder of Betaworks and was previously at Dawntreader and AOL. His easygoingness belies the fact that he's one of the most thoughtful investors in the business. 

Andy came up to talk to my entrepreneurship class at Columbia University's engineering school. I have people from the startup world in class every week. The point is not to have them teach, but to have a conversation with the class about what it's like to be an entrepreneur and to be part of the innovation economy. If the three turnings of the wheel are learning, knowing, and enlightenment, the speakers bring about the second: not what we do in the innovation economy, but what we are. Andy's talk is a great example.

Andy talks about what an entrepreneurial environment looks like--even in a company that's no longer a startup, how Betaworks did product development, where he sees business on the internet going, and what USV looks for in a startup. Andy's a really approachable and engaging speaker and I wish I could have had him talk twice as long.

Some marks:
0:00 - Intro, Andy's early career, at AOL
7:17 - Starting Betaworks
11:52 - Joining Union Square Ventures
13:47 - AOL diaspora
14:49 - Background of entrepreneurs
19:14 - Entrepreneurial environments--autonomy and empowerment
21:34 - Life after an acquisition
22:30 - Ideation and product development at Betaworks
30:55 - Evolution of internet business
33:20 - Next stage in internet business evolution
40:21 - NYC's internet ecosystem
44:39 - Is there a 'New Tool' now?
45:56 - Future of the internet
48:16 - What is USV looking for in a startup?
53:06 - Balancing data and gut feel in evaluating your startup idea
55:54 - Regrets?
56:32 - Most intriguing company he hasn't invested in.

If my fourteen-year old got her hands on this video it would have jump cuts and pan zooms and a swelling soundtrack and lots of duck-faces. Instead you get what you get: occasional bursts of static and a weird pan to the previous class' blackboard notes. And no, I have no idea what those equations mean.