I’ve been spending my mornings this weekend, listening, watching, and reading things. I’m always reading to find content for this blog, but I’ve allocating more time to consumption this weekend. So you might be noticing a slightly different varietal of posts over the past few days.

This morning it’s a podcast called Dorm Room Tycoon. It’s an interview with Andy Weissman, who is a partner with the New York venture capital firm, Union Square Ventures. The topic is “how we invest” and I’m enjoying the discussion.

Andy describes their firm as being boutique and thesis-driven. Meaning they have theses and they look for companies that dovetail with them. But in addition, he also labels their approach as “conversational investing.”

What does that mean?

It means they listen, watch, and read. They blog (all the partners write their own personal blog). They engage and discuss. They put themselves and the firm “out there”. And they don’t pretend to have all the answers or to be able to predict the future. Instead they let their conversations – both internal and with the broader market – help them make their investing decisions.

So why do I bring this up?

Because in my own small way, I am trying to do the same with real estate development, architecture, and city building. I write every day to learn and because I am infinitely curious. If you want to know what I’m thinking about, read this blog.

It’s for this reason that my favorite blog posts are the ones in which there’s lots of discussion in the comment section. It’s the market talking back, telling me whether I’m out to lunch or not. Ultimately, this idea of “conversational investing” is really about iterative decision making.

Here’s the podcast embed in case you would also like to listen:

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Regardless, the Dorm Room Tycoon is worth checking out. They have other interviews with people like Malcolm Gladwell and Simon Sinek.

This morning Kevin Marshall tweeted me a link to a blog post by Andy Weissman (partner at Union Square Ventures in New York). The post is about how small things matter—even small words.

He starts by talking about a new sidewalk extension and curb cut at 86th Street and 3rd Avenue in Manhattan. This may seem like a pretty banal thing to talk about, but it’s in support of his argument that small things—like even a curb cut—can be used to solve bigger problems. In this case, the intersection was a dangerous one because of poor pedestrian visibility.

But what I really like is how he describes the pulse of New York:

"The rhythm of NYC is such that we need to keep moving and in motion; as a result, waiting to cross a street by standing at the curb is not enough, we must walk into the street to get going or keep our momentum."

This is great and it’s bang on. People in New York don’t stand at the curb waiting for the light to change. They impatiently push onto the street and wait for the first opportunity to cross. This may seem like a small tendency, but I think it speaks volumes about the character of New York.

People in Toronto generally don’t do this.

They (not me) wait patiently at the street corner even if there aren’t any cars coming. Why? Think about this the next time you’re standing on guard at the crosswalk. Don’t lose the momentum. The world rewards those who poke the box and keep moving.