Most Interesting People in the Room


The Premise

There are some conversations that stick with you.

You remember the location, the people involved, the smells, the art on the walls or the texture of the bamboo mats beneath your feet. The moment stands out because the discussion you had was so engrossing, so world-shattering and parallax-shifting that you’ve filed it in your mind under ‘Epiphany Moments’ and go back to reference it from time to time.

And if you’re anything like the majority of people in the world, you can count on one hand the number of times you’ve had this kind of moment.

This is no reflection on you, of course: it’s rare that the stars align in such a way that a group of remarkable people with interesting opinions and unique collections of experiences find themselves in the same room at the same time and all ready and willing to converse about whatever happens to come up in the moment.

If given the opportunity, however, I think most of us would like be in these kinds of conversations more often, and unfortunately it’s getting more and more difficult to do so, even online.

Increasingly, forums and comment sections have become places to agree with whatever has just been said (or a way to get your name out) when they’re available at all. Hot debates are few and far between, and most aren’t so much real conversations as pissing contests between two egos with a reputation to manage.

I feel like there should be an alternative, and I’ve set up a new project – an experiment, really – to allow everyone to have a potentially life-changing conversation at least once per week.

Most Interesting People in the Room

The new project, which is called Most Interesting People in the Room, is a newsletter (powered by and message board (powered by Disqus, just like the comments on this blog) through which I’m aiming to provide a unique interactive experience.

Each week (on Tuesday night), subscribers receive an email with 5 prompts: a quote, a question, a thought, a link and an exercise.

Subscribers are then able to go to the message board and engage in riveting conversation using these prompts to get the party going.

There is a great deal of deviation from the prompts (at least there has been so far) and often the deviations are the best part. The point is not to definitively answer a question or do homework (you don’t have to talk about the prompts at all), it’s to have some jumping-off points that serve as common ground to start with and then move on from there.

A simple concept, I know, but here’s where I mix it up a bit.

Every week, the person who had the most interesting/helpful/insightful commentary will be named ‘Most Interesting Person in the Room’ and will be awarded 10% of the total subscription income.

The cost of subscribing is $10/month, a nominal fee, but one that grows quickly when a decent number of people sign up for something.

I invited a core group of people to join me (from my personal contacts and my newsletter) with 10 paying subscribers among them, so right now the reward each week is $10, which repays the recipient’s monthly membership fee.

Matthew Stillman is the Most Interesting Person in the Room this week, by the way, so go tell him congrats through his newly redesigned website if you get the chance!

Takeaway Points

This project can be many things – a networking tool, business venture, conversation starter, fun experiment – but below are a list of points in case any important distinctions were lost in the paragraphs above.

  • Most Interesting People in the Room is a subscription-funded newsletter and comment board
  • The main purpose is to engage people in stirring conversation at least once per week (and hopefully more than that)
  • The cost is $10/month, and each WEEK whomever is the ‘Most Interesting Person in the Room’ will receive 10% of the total income from membership fees (that means 40% of total fees are given right back out to subscribers)

This is not a project for everyone, but I would recommend it to

  • People who are looking to exercise their brain every week (in a way that their work- and home-life can’t provide)
  • Those who are looking to meet new and interesting people
  • Anyone who is looking to improve their discussion/conversational/debate skills with others who are doing the same
  • Folks who want the chance to get paid for providing value to a group of people who will appreciate their candor
  • Individuals who are looking for some amazing content to read, generated not for an audience of blog-readers (no top ten lists or pithy recycled advice here), but for an audience of intelligent people who are looking to expand their horizons and help others do the same

I would love to build this up so that everyone is able to become engrossed in excellent conversation every week and I’m able to give away thousands of dollars to people for being brilliant, so come and check it out now if you want to help shape the direction of the project from the beginning.

If you haven’t been scared away, you can click here to subscribe to Most Interesting People in the Room, or shoot me an email with any questions you might have.

The next newsletter goes out Tuesday night, so if you sign up before then you’ll be able to jump right in to the fray!


  1. this sound crazy intuitive.

    Colin to be honest, I’m not a big fan of making people socialize through contest. Forcing interesting social fireworks doesn’t seem like an equation for success. I feel if a bunch of people got together in real time and had to be interesting to win a contest, you’d pretty much get a lot of loud desperate people and people trying to talk over each other looking for their turn to talk. That, to me, isn’t a great or responsible social atmosphere. Then you have to consider who is actually judging what it means to be interesting, in hopes that this contest wouldn’t serve some type of bias. Is there a judging panel, is this America’s Next Top Social Person? Well that’s just how I feel about it.

    . . . bamboo matts underneath your feet?

    • Thanks for the feedback, Jonathan.

      Honestly, I have similar concerns. As a student of sociology, I know the frequently systems in which there are rewards present to encourage a certain kind of behavior, often the rewards can take priority and lead to improvements in methods of attaining that reward, but not necessarily in achieving the original intention.

      That being said, I’m also fascinated by alternative means of stimulating debate, and at the moment I’m disappointed in the lack of really solid conversation and debate of any kind on the Internet. Here we’ve got a network connecting a goodly portion of the world and instead of conversing our way to a resolution (or at the very least, an education), we have pointed it firmly toward marketing, resulting in the same old blog posts and the same old comments, and that’s what passes for intelligent discourse.

      I’m painting with broad brushstrokes, of course, since there are definitely some places stimulating a decent amount of discussion, but I think the escalation in bloggers removing comments from their blogs completely is a testament toward just how worthless the exercise of commenting has become in the vast majority of cases.

      My intention is to see if the combination of social-incentive (being among people who are PAYING to be part of a conversation…which will in most cases lead to an audience that is more invested in making the conversation worthwhile) and financial-incentive (providing a reward for intelligent engagement, which provides value to the group…a bit like crowdsourcing, if you think about it) will result in some kind of solution.

      As I said, it’s an experiment, and you may be right, but I for one am willing to try new things and see what happens.

      At the start I’ll be the one deciding on who takes the title each week, and you can draw whatever conclusions you want from that, but because I know what I want the group to be, I can be sure the right kind of people and conversations are being rewarded. This also may change over time, but I didn’t want to complicate things from day one by having to wait on a handful of people (or worse, ‘the crowd’) to vote on something as subjective as this.

      Hope this clears things up a bit more! I’ll keep you updated as to how the project is going.

      Bamboo mats = a conversation in Thailand or in a Pier 1.

      • Cool.

        I think I performed exceptionally and that I should win your contest indefinitely because I provided a means of opposition, yet also laid straight into your course of objective. Pretty commendable, I think.

        Go me! :)

  2. Respect to you Colin for putting this together,
    Sounds like a really interesting project. I may just have to come and join the party. You can’t beat a good bit of debate.

    • Thanks Milt!

      Would love to have you along for the ride. It should be interesting and a great way to meet some other interesting folks, if nothing else. Best-case scenario, it may even take off in a big way.

      Nothing to do but wait and see!

  3. This is a really cool concept, Colin. I’m going to go check it out. I think you might take a lot of heat at first for how you choose winners. I imagine at some point it might evolve to a voting format?

    • Thanks Carmen!

      Yeah, I expect a little heat, but I also think it’s a better idea than the regular voting formats most online ventures use. The blogosphere is such a back-patting environment I don’t want a group of people all feeling like they have to vote for their friends.

      I KNOW that I can be heartless and as unbiased as a person can be, and that will have to do until I (or someone else!) comes up with something that makes more sense.

      *shrug* The nature of the experiment! Let’s see what happens!

    • Thanks Carmen!

      Yeah, I expect a little heat, but I also think it’s a better idea than the regular voting formats most online ventures use. The blogosphere is such a back-patting environment I don’t want a group of people all feeling like they have to vote for their friends.

      I KNOW that I can be heartless and as unbiased as a person can be, and that will have to do until I (or someone else!) comes up with something that makes more sense.

      *shrug* The nature of the experiment! Let’s see what happens!

  4. What a great concept!Even if this doesn’t work “with you” I seriously believe that some people will pick this concept to make other things, or at least they should!Even being a student, with a very tight budget, I’m really tempted to experiment.

    • Yeah, I’d like to see it work out somehow, even if it’s not this iteration.

      Either way, I intend to take it as far as I can. I’m already seeing some limitations in using as the foundation, so I may cobble something together next month if this month continues to go as well as it is.

      It would be great to have you involved!

  5. Very interesting idea. I wonder if contest money is a good incentive to encourage conversation?

    In university, some of my classes had a portion of the grade determined by participation. It felt like there were always a couple of students who just wanted to blab on about nothing. However, I do think it encourage some of the quieter students to speak up more.

    You have some cool projects in the works Colin.

    • Yeah, it could go either way…I know that generally it’s not ideal to offer a reward other than the intended target, but in this case I understand that a lot of why people don’t invest time in their online conversations is that they literally aren’t invested in them. This way they’ve put money down to be involved so they’ll be more likely to take the time, PLUS if they say something really brilliant and add value to the project in doing so, they’ll be rewarded for it.

      We’ll see how it goes! The more interesting people we have involved from the get-go, the better we’ll be able to see what works and what doesn’t and adjust from there, so any promotion you can point toward it would be much appreciated!

  6. Love the concept and im glad im part of it. I will probably never be the most interesting person in the room but i really enjoy learning, reading all the comments and most important meeting new people.

    So for that, Thanks for accepting me :)

  7. What an interesting and exciting concept, Colin. You never fail to create new and stimulating conversations and conversation-starting agents (like this new project).

  8. Do you mind if share an article on interesting people? It quantifies the concept of being an interesting person into five distinct aspects; knowledge acquisition, societal outliers, raconteurism, communication style, work and the entrepreneurial spirit.

Comments are closed.