The Art (and Science) of Founder Dating

I’ve been doing some serious hunting in the last few months for a new company / product idea to pour myself into. I thought it would be valuable to talk about how I’ve gone about the process, as I’ve learned a bunch and have been constantly refining my approach. I’m going to talk about one case specifically, though I’ll change the names to protect the innocent.

For purposes of this exercise, I’ll call the other party George.

George started following me on Twitter a couple of months back. I always, always go look and see what people who start following me do for a living. When I saw what George did, I was really intrigued about two things: What brought him to me, and what was he up to next?

Initial Contact

ME: Hey George, looks like we’re into some really similar things. Interested in connecting?
GEORGE: Assuming this isn’t an automated DM, yes. <email>
ME: Great, I’ll reach out via email.

Notice I was direct and to the point. No fluff. People are busy.

Starting the Conversation

ME (via email): I looked at what you are up to, and it’s really great. I’ve already referred a couple people to your product. Would you have time for a 15 minute call, tops to get introduced this week? The days and times that would work for me are <various dates and times in the next 3 days>.
GEORGE (via email): Let’s do tomorrow at 3:00. I’ll send an invite.

Again, neither one of us wasted the other’s time. I now know George is worth talking to. He didn’t blow me off, not a lot of back and forth. One email and we’re set for a call. Brilliant.

On that first call, we spent at most 30 minutes introducing ourselves and learning a bit about each other. I wrote down a few key things he was working on / trying to solve during the call, then right after we hung up I sent another email:

ME (via email): Hey George. Great to chat with you today. When you were talking about x on the call, I thought of these two things that might be helpful for you. They’ve helped me a ton. Let’s stay in touch as we both go forward and see what happens.

I show I care about what George cares about and that I immediately offer something of value (I hope), something novel for his problem.

GEORGE (via email): That’s great, thanks. Here’s a link to <something I will care about>. Let me know what you think, and yes let’s definitely stay in touch.

Again, we’re both interested and we’re both contributing value to the other. We scheduled another call. We’re starting to establish very early trust, which is critical at this point. No one’s asked for anything. It’s a two-way street, no one’s selling.

Follow-On Calls and Emails

We had a series of follow on calls where George shared in depth what they were working on and asked for my take on the idea and how they were thinking about it. Based on our conversations, I knew that George was complementary to what I’m good at and visa versa. At this point, I started thinking seriously about what a working relationship might look like, and I offered some options.

ME: I know you’ve got X right in front of you. Here’s how I’ve solved that problem in the past, it might be useful for you. Here’s some links to other stuff that I think will directly inform the issue you’re thinking about. I know it’s early, but I wanted to float some options for how we might work together on your project.

GEORGE: Options 2 and 4 sound really interesting. Let’s keep talking, for sure. I think there could be something here.

From here, George and I got into deep conversations around our core values, how we think about building a great company, in-depth product ideas and so forth. Very open and candid conversations on all fronts. George did a great job of pulling information and ideas out of me, and asking all the right questions that I would want to discuss. My goal was to get to a solid “no” or roadblock as quickly as possible. As I write this, the conversation is still going.

George is one example of 10’s of conversations I’ve had around opportunities in one form or another.

Here’s what’s been common in all of the conversations that have gone well:

I’ve been very up front and candid about where I am and what I’m looking for. No selling, just the truth.
I’ve taken a genuine interest in what the other person’s up to and tried to be helpful, regardless of outcome. I don’t think I’ve started one conversation with “Here’s what I’m doing. Am I amazing or what?” Care about the other person more than yourself.
When I stop getting responses, I stop the conversation. Either they’re serious or they’re not. I don’t need to waste time with someone who’s not.
I’ve followed each of them through to some conclusion. I don’t want to be the one that left something hanging. End well.
Every communication is intentional, with the goal of advancing the conversation to the next decision point.
Add value in each interaction. Even if you don’t end up working together, relationships have a way of circling back in the most surprising ways.

Some of this may sound obvious, but you’d be stunned at how many people treat this process as a one-way street. No one worth their salt wants to work with anyone like that.