When trying to make founder friends on the Internet, learning about their context is important. People have different constraints and motivators in life that play a huge role in their thinking and business related decision making.

Below are some of the questions that I think are important. I wish there was a socially accepted protocol where we could skip right to exchanging such details. Especially when both people are open and believe in sharing in the interest of learning from each other's data points (But in reality it takes time to move beyond the surface-level conversations, especially to details having to do with money). But until we get to some real talk, we can't truly help each other or engage freely in advice giving/taking. At least I often feel like I can't if I don't know someone's full context.  

  • How is your time structured. Are you working a day job? is this a side project? Is your aim to go full-time? Are you living of savings? etc.
  • How much time did you spend on X (for example. "I grew my twitter to X followers in Y months?" how many hours per day or week did you spend writing tweets/engaging.)
  • How much did you make from X project, revenue and profit.
  • What is your runway, how much savings do you have?
  • Number in the bank at which point you consider yourself financially interdependent? You know, what's your F-U number.
  • Partner situation/married or what not (affects free time)
  • If they have children or not (affects free time)
  • What do they do for health insurance (in the U.S. this is a reason for a many to not go solo)

I am happy to answer any of the above questions about me. In a 1-on-1 conversation, I'd be open and share with potential friends (Though I doubt I'd ever post such things publicly). On the other hand, I often err on the side of not asking personal questions and never want to seem like I'm prying.  During our Friday chat, my sister challenged this about me. She said often people are happy to share, actually want to share. You just have to ask some open ended questions and listen. I know she does this and is good at getting to know new people faster. And people seem to open up to her and share all kind of details, based on the stories she has told me. (This also jives with what Michele Hanson talks about in her book Deploy Empathy, in the context interviewing customers and getting them to share details about their process and problems).

When I was listening to IndieHacker's podcast interview with Justin Jackson, I specifically remember him mentioning that a friend showed him their bank account and how much money they were actually making from something. And that opened his eyes and informed some decision. This resonates. I'd be glad to have such friends, and share if it helps them with a data point. Helps them learn something from my experience or helps them make a decision.

A related thought: Being able to exchange candid feedback

The amazing thing about the human mind is how capable it is of coming up with, convincing itself of and believing in all kinds of bull sh*t. One of the most underrated things in life is friends who call you out on your bullsh*t. With all due kindness.

You have to really get to know someone to be able to do this though. And that takes time. The compounding and all, as it applies to relationships. Especially friendships. I think it's valuable for someone to challenge your thinking and your assumptions. Yet another reason to go beyond the surface-level banter and have real in-depth conversations about your values and goals and what you're trying to accomplish and why. I have this with some IRL friends. And as start to make more Internet friends, I'm thinking more about how to achieve this.