Ask YC: How did you pop the question? (to your co-founders)

[wheels]

There's a friend of mine that I think I'd really like to have on our team, specifically as an exec. I've known him for years, he's already got one startup under his belt (as a founder) and he's got a good head for business.

I'm debating how to pop the question. I asked my current co-founder via email, since I knew we'd see each other that day and wanted to give him some time to think about it. How'd you guys do it? Any particularly funny / successful / horrible experiences?

Edit: I should have been more clear in the original post based on some of the replies: We're already several months in and in beta, so we're not at the "I have an idea"-phase, but still pre-money. This is someone I'd like to come in since I think he'd round out the experience that the two of us have.

[apgwoz]

I asked them to accompany me to the beach and sat there with them, trying to get the nerves to pop the question. They knew it was coming, and after fumbling around like an idiot for a little bit, I spoke the words

    I've noticed lately, that you've been lagging at work. You feel empty inside, and the 
    work you're doing is meaningless. I feel it too, but I also feel that together as a 
    team, we can make something. We can be something, and we can take over this damn world 
    and keep a portion of the profits. We can fix things--together. So, I'm asking 
    you...will you start-up with me?

[maxklein → apgwoz]

And he said - Our friendship is too important, I don't see you that way...

[ConradHex → apgwoz]

What kind of ring did you give? :)

[robfitz]

i was like "hey, you want to start a company?" that worked pretty well.

or ask him for help coming up w/ a business plan. by the time you're done, he has a sense of ownership over the idea and is [hopefully] excited about it.

[PStamatiou → robfitz]

i spotted a fuzzwich t-shirt in the wild yesterday.. you guys are getting around :)

[portfolioexec]

I'd suggest getting together for some social (basketball, a drink, playing cards... whatever you guys do) and have a casual conversation. Never be too keen to let others know what you're thinking. Once you've been hanging out a little while, start bouncing the idea. As in discuss the business opportunity and see how excited he gets about it - without actually mentioning that you'd like him to join.

You know that he's got skills you need, but does he want to be involved? You can test this by just floating enough information for him to have to work a little to get more out of you.

This could then lead to a passionate, enthusiastic conversation and result in the outcome you want. If he doesn't take the bait, maybe offer a little more, but ultimately I think it means he wouldn't be right for the team - lack of burning desire.

We always appreciate most the things we've worked hardest for :)

[unalone]

I talked to mine a little while after he got to college. I'd been there for a few weeks, and we'd been talking about how dull college was compared to the program we'd been at the summer before. (It was a very selective education-intensive month-long course, and I think we'd both describe it as one of those events that inspired us forward.) I asked him if he'd be up for trying to launch a web site business, and he said "absolutely." And, after talking about it for a while, we both agreed that if push came to shove, we'd both drop out rather than abandon the project, if it ever seemed like there'd be a foreseeable future to it. We'll hopefully be applying for this next summer.

I think you should try to get him excited with what you're doing, first things first. If he's passionate about it then he'll be that much easier to recruit.

[rodmaz]

Just be direct and honest! Something like "You know, I always wanted to start a company and do something exciting. I think we would make a terrific team and would like to hear your opinion." Good luck!

[arien]

I had to talk to a coworker who had this excellent idea, but either didn't realize it or didn't know how to "sell" it. So I told her, "this idea is great because of X and Y, and I want to help you develop it". She thought about it and agreed with me. So here we are trying to carry it forward!

I think you have to consider if your project is good enough for your friend to drop his work and come help you. And then consider if you can actually find the words that make him feel like that. But focus on enthusiasm and above all, honesty :)

[gsiener]

If he's a good friend, he no doubt knows about your startup/venture already. If not, start by giving him the details and presenting some of your challenges. I'm guessing that he will have lots of ideas and solutions, and will even follow up after your conversation with more thoughts.

If he does, then mention that you'd love to explore him coming aboard. Seems to me you should be selling your vision and getting _him_ to bite.

[terpua]

Just ask. Be direct and don't tip toe around the subject. Realize that it will be a hard (but rewarding/learning) experience.

Make sure you have founders agreement and a way to settle disputes so that friendships aren't destroyed.

[maxklein]

Go out to a bar, over some drinks push the idea a lot, see if the other person likes it. At the end, mention that if he ever has interest in joining you, you'd like it.