Through colleagues I’ve heard about an entrepreneur who I think would be a great cofounder for a business I already have significant traction with. I’d like to slowly assess his interest in my company and in making a move. How would you approach him and what would your strategy be to reel him in?
get to know him. You don't know if you want him until you know him. He won't make a decision until he knows you. get to know each other.
I agree with Rob. Leadership training teaches that you have to find out what motivates them to want to be with you. Getting to know him is the only way to understand what his needs, passions and desires are. Only upon knowing that, can you create a strategy to sell him into joining your company. For more free help, see Invenst Team, a platform I created to help people like you for free.
You're saying he's a cofounder in another company, this is essential. Founders are not employees (they should be above that), thus poaching is harder. If the founder is committed to the other endeavour -as he should-, in theory, it should not be possible to poach him. Now, that doesn't mean he can't help you, or give you some council or advice, but to steal him outright is a different story.
The word commitment is key here, like in any relationship. So this process is like saying: I like this other person significant other, I would like to poach him/her.
Having said that, if you get to know him and he's willing to jump ship, the poach process will be messy, as he should have equity on the other endeavour, which in turn will mean his exit will be messy, weather legally, economically, etc. Maybe if you're willing to absorb those costs, things might go your away. If that person worth that effort?
Best of lucks!
If you can afford to move slowly with your startup, great. But do your best not to waste people's time. Time is everything.
Get one if the people who gave you the prospect's name to introduce you via email. A warm intro is helpful. Reply all, thank everyone, and note that you will follow-up with prospect under separate cover.
Ask for a short meeting. Say you are looking for co-founder and advisor recommendations. Make sure meeting is at a convenient time and place for your prospect. Do not send attachments about your company! If the prospect wants info, they'll ask.
Show up early. Pay. (I shouldn't have to say this but....) The first thing you say is "thank you for making the time to meet with me, x. I have heard so much about you from x, x, and x....would you take me through how you got from x [you looked this up] to current startup? <-- Idea is to NOT launch into a big thing about you. Now, listen! Do you hear "we" or "I"? Do you hear optimistic recollection or pessimissm? Enthusiasm about fundraising and biz dev or dread?
You might run out of time. If you do, get a second meeting.
Still have time? Just be up front. This is not difficult. Give your elevator speech. Share what you need next to succeed, peeps. And then, if you want to go to the next step with this guy, ask him if he would be interested in exploring a co-founder role. If he says no or you have already decided no, ask for recommendations. You'll want the prospect in your circle either way.
(As for disruption in his current startup, meh. Nearly all founders leave their startups eventually. (Startups feel like babies but it turns out that they can survive on their own. It's terribly disconcerting.) The question is when--when does a founder leave. I advise all startups, especially those with multiple founders, to have an exit strategy in place after the first dollar is earned. This makes it easier for founders to make the best choices for themselves and their companies, and it limits the chaos of what can be an emotion-ridden departure.)