It's important to determine whether or not the person is qualified and capable. While questions have their merit I'd recommend a more creative exercise. If you have the means, take a trip half-way across the world and live in close quarters for 3 weeks together (while you work to get the business off the ground). If you can't stand them by the end of the trip; walk away. I've been working with my cofounder for 15 yea…
Clint Eastwood was on some talk show long ago, and he was asked about relationships, girlfriends, etc. He said he tests potential girlfriends by going on a three-hour driving trip. If they still have anything to talk about at the end of three hours, they have potential. I think that would apply very well to cofounders, too.
Ask HN: What questions did you ask (or wish you asked) your cofounder?
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Re: Ask HN: What questions did you ask (or wish you asked) your cofounder?
#22The most important element, in my opinion, is one that single questions alone cannot discern: Is this person a workplace psychopath? I'm not kidding, and this is a real issue. A lot of people who can be great entrepreneurs can also have detrimental effects on your culture, the trust of your clients, and your long-term sustainability. Drive, initiative, passion, aptitude - these are qualities present in great founders…
Re: Ask HN: What questions did you ask (or wish you asked) your cofounder?
#23The most important element, in my opinion, is one that single questions alone cannot discern: Is this person a workplace psychopath? I'm not kidding, and this is a real issue. A lot of people who can be great entrepreneurs can also have detrimental effects on your culture, the trust of your clients, and your long-term sustainability. Drive, initiative, passion, aptitude - these are qualities present in great founders…
The straightforward though not necessarily reliable way to get a basic read on this is how they treat the waiter in a restaurant. Maybe conspire with said waiter to minorly screw up their meal service once or twice.
http://www.businessinsider.com/charles-schwab-ceo-takes-job-...
Re: Ask HN: What questions did you ask (or wish you asked) your cofounder?
#24I have a friend who helped start someone selling a breakfast product. The plan was my friend would invest $20k and the partner would run it as a local business, and they'd split 50-50. Very quickly my friend got excited by the potential and started working full time to help, ends up investing hundreds of thousands of dollars, doing all e-commerce, marketing, negotiations, paying for industrial quality kitchen, etc, while the partner just mixed and packaged. Sales shot up and the company begins to have significant value, but still requires more investment.
They needed to switch from an LLC to a C corp so they could get funding and start giving stock options to attract/keep good employees. The partner conceded that my friend was doing the lions share of the work and had put a ton of money in while he had put in nothing, and that my friend should have most of the initial stock in the C corp. But they struggled to agree on an exact split.
So then the partner talks to friends and family who of course tell him "it was YOUR IDEA, you shouldn't have to give up anything!" and comes back refusing to sign anything (which scotches the C corp conversion). Eventually he's able to force my friend to buy him out for a totally unreasonable price.
So my specific advice is.
1) Never start a new venture as an LLC unless you don't plan to ever share equity with employees AND you expect it to be a cash flow business that will pay out all profits directly to partners.
2) Always force all partners to vest their equity over years. You can do incentive stock options, or restrict stock units, or however you want. If you can't afford a lawyer to draw it up yet, at least put the arrangement in writing and agree to it, so that if you have disagreements and need to part ways, you aren't being forced to buy half the business from some guy who mixed ingredients for 6 months.
Re: Ask HN: What questions did you ask (or wish you asked) your cofounder?
#25Re: Ask HN: What questions did you ask (or wish you asked) your cofounder?
#26Otherwise, there aren't enough interview questions in the world to tell you the important stuff.
Re: Ask HN: What questions did you ask (or wish you asked) your cofounder?
#27I worked with a person with the plan to raise money later. It turned out he didn't run his current business well and soon wasn't able to pay for rent, had to sell his car, stopped paying the rent for the office we were sitting in. Looking back it explained a couple of questionable decisions (e.g. claims to debtors, very much over-promising, aggressive release plans, side-projects to make extra money). I'm not saying you have to be well off before going into a months/years long project but living paycheck to paycheck isn't a glorious "[he|she] is hungry and eager to make this a success" but plain stupid.
Re: Ask HN: What questions did you ask (or wish you asked) your cofounder?
#28The most important element, in my opinion, is one that single questions alone cannot discern: Is this person a workplace psychopath? I'm not kidding, and this is a real issue. A lot of people who can be great entrepreneurs can also have detrimental effects on your culture, the trust of your clients, and your long-term sustainability. Drive, initiative, passion, aptitude - these are qualities present in great founders…
The straightforward though not necessarily reliable way to get a basic read on this is how they treat the waiter in a restaurant. Maybe conspire with said waiter to minorly screw up their meal service once or twice.
Meanwhile he'll be playing the long con with you - manipulation and mind games that can be incredibly subtle. I had the misfortune of working with one of those for a few months - we almost became co-founders. Recognizing and getting out of that situation before I got in any deeper was one of the smartest moves I've ever made.
Re: Ask HN: What questions did you ask (or wish you asked) your cofounder?
#29Number one thing is discussing the equity split and what happens if one of you quits. I have a friend who helped start someone selling a breakfast product. The plan was my friend would invest $20k and the partner would run it as a local business, and they'd split 50-50. Very quickly my friend got excited by the potential and started working full time to help, ends up investing hundreds of thousands of dollars, doing…
Re: Ask HN: What questions did you ask (or wish you asked) your cofounder?
#30Earlier quoted context omitted.
Clint Eastwood was on some talk show long ago, and he was asked about relationships, girlfriends, etc. He said he tests potential girlfriends by going on a three-hour driving trip. If they still have anything to talk about at the end of three hours, they have potential. I think that would apply very well to cofounders, too.
And a simple test of how well two founders work together is to take a two-person canoe down a course that demands teamwork. Be sure to switch off who is front and back. I've seen couples descend into cat fights in a canoe.