He was a top level executive doing CEO-type stuff that would be a good fit (b2b) for our startup. Just recently he decided he wanted to spend more time with his family so he "retired", while still in his 40's. We have a culture than could accommodate his desired lifestyle, I'm willing to incentivize him for what he's worth, which as a marquee asset would be quite a bit. We have exclusive IP that will change the medical world (e.g. think: joint replacements becoming a thing of the past), and we recently won an accelerator competition, and we're already in talks with big companies about some major investment. I know you're all about answering the question you think I should have asked, but I've looked at all the aspects and it should be a great fit. My question is, is there a book anyone can recommend or just some sage advice on how to court him? I don't need the "bring him on an interim basis" type advice ... I'm pretty sure that would insult him, and a guy like this ... you don't do that. He already has a plan to go enjoy life and I want to convince him that this will be more enjoyable. I just want some ideas on how to approach him and some things to watch out for. Oh yeah ... and I'm pretty sure he'll say no, but it doesn't hurt to ask.
David, I agree to be direct. Per your fear of him feeling used, I would make sure you outline the skill set you need that he can offer rather than his past title. At the end of the day if I am an investor I say who cares what he has done or who he has done it for, but rather how is he going to apply that to your company, the second part being much more important for the future. If you do not need his contacts, point that out and that you need his strategy advice.... If you need his contacts and that is all you need, then be upfront that your IP is valuable and you feel he has the needed relationships that build your company...most importantly because you have something that will help a lot of people and without his involvement those people may not get the product/help that could make their lives better. Friend or not, what are his passion points...people are drawn toward their interests when they have limited time. My initial concern is your pitch of "think joint replacements becoming a thing of the past") sounds like an infomercial for a do all vitamin. But I would love to hear more about it if you have discovered the fountain of youth. But, personally and subjectively I dont think that pitch line is a good one because you will never completely rid joint replacements...there are always going to be circumstances that require joint replacements. So in otherwords, I would target in on the action your IP is doing...which is not ridding the need for all joint replacements but strengthening cartilage/joints, infusing bone and cartilage strengthening compound into a weakened joint, preventing the need for risky and costly surgeries, providing a better option to surgery. And then once you have done that, your target market will be clearer...but rid the world of joint replacements...100% not happening due to the complexity of individuals, injuries, etc. Not to mention you are going up against billion dollar medical suppliers and big pharma with lawmakers in pocket that make a lot of money off the thing you are claiming to rid the world of (Though I hope you have something that betters joints as Im sure most do!)
It sounds like you already have a relationship with him, so just be brutally honest. This way he knows exactly what is expected and the direction of his role. Go buy him a coffee, chat for a bit. The worst thing he can say is no.
First, wait until you see signs of restlessness. That usually happens within 90 days, but you may not know for another 90. Then ask very directly if this would be interesting to him. Do not beat around the bush, but do not oversell. If he is unavailable for a "day-job" then see if he would be into a BoD position (not consultant, not interim, not "advisor") because you will need people with that experience as you build out. The issue with "top level executives doing CEO-type stuff" in large companies is that they can be lost in a startup, and vice versa. My wife is in a huge company and has been all her life (Fortune 10s also). I have been in startups for 30 years as an investor, and 20 years as an operator. Neither of us can understand how the other can stand that situation.