I'm male and my co-founder is female. In the beginning when we started, we were really good friends but never saw each other as a romantic interest. But now having shared many ups and downs together, we are beginning to develop feelings for one another. I like her, but I'm also worried that pursuing something romantic would not be good for the company. Have you ever gone through this experience and could share your thoughts?
What's going to be more important on your deathbed: the success of your company or a love you shared with someone, for however long it lasts?<p>Edit: My wife is the cofounder of our life and family together, and I have yet to find a business opportunity that could ever compete with how she makes me feel.<p>Maintain perspective. Life is short. Maximize for happiness.
This exact situation happened to me. I founded a magazine with an amazing woman. In the beginning, we were just close friends, but as we went through ups and downs, our feelings for each other changed.<p>Like everything else, this kind of relationship has good and bad points.<p>The best thing was the degree of understanding. I've never been in a relationship with someone with such an incredibly innate understanding of my career. It was truly magical.<p>But, then there was the bad. Until you've been in this situation, you can't understand how deep the conflict of interest can get. Sometimes, co-founders need to have frank conversations about performance. When you're in a romantic relationship, frank feedback can create deep wounds. Then, in our case, once the magazine died, our relationship died too. The double whammy of a failed startup and failed relationship was unlike any other breakup I've ever experienced.<p>All that said, I'd do it again in a second. The relationship was so good while it lasted and Stacey is still one of my closest friends.
It's not uncommon for folks working very closely together to form emotional & romantic relationships. (Aside: raising kids is the ultimate startup, that's kind of why marriage exists).<p>First, make sure you have clear founder agreements, focusing on the case where one of the founders leaves (this usually implies vesting of some form). If you enter a relationship and then break up, the odds of one of you leaving at some point is increased.<p>Second, if you have investors, a board, and/or other key stockholders, you should consider disclosing a serious relationship (should it get to that point, for some definition of "serious").<p>Some will say, "it's none of their business!" but it kind of is. Most companies of any size have a policy on workplace relationships, and the minimum is usually that they must be disclosed. Even if you're too small for an HR department, the issues around potential conflicts are the same.<p>You never, ever, ever want to be in a situation where you date, break up, one departs, the company is compromised, and an irate investor later says, "you never told me!".
A lot of people in in the comments seems to assume you'll get married. Which, while I wish you luck, may not be the case.<p>With that said, while I can't speak from experience, if you are equal founders I say go for it. If one of you is in a position of authority over the other it becomes much more tricky.<p>The only down side I can see is if you two break up and it gets messy. In which case, having a good board of directors that can be neutral and think about what is best for the company is important.<p>Edit: a little bit from personal experience though. If your startup hits a rough place and you need to sacrifice things like pay, it can be helpful when your significant other has a stable job. And if you both work for the same startup that is not an option. Money is what breaks up most relationships and if there is one thing startups are good at, it is creating money problems.
> I'm also worried that pursuing something romantic would not be good for the company.<p>Yes, it rarely ends well.<p>If you end up in a long term relationship or even get married, then the boundaries between work and home get blurred, and on top of that, if you have vested interests in the success of your work (which is your company) things could easily get out of control - clashing egos, 1 partner feeling the other is not doing enough at work, or at home, or both.<p>I've seen 2 of my close friends end up like that. Doesn't mean that's the norm, but things get ugly over a few years...<p>That doesn't mean you should not pursue the romantic relationship, just saying be cautious and don't over-commit too soon. Wait for the "honeymoon period" of the relationship (if you do end up moving forward) to pass and see how thinks look. In "normal" relationships, this period is usually anywhere from 6 months to a year or two...
I know a couple who married after founding a startup together. A VC said that they frown on it, because it meant that breakups would be very messy. But that's really the only negative. The upside is that you two would be the only ones who really understand the other's career. The current startup I work is is also run by a married couple, and the founders encouraged me to bring my wife into the company as well.<p>To be quite honest, I think it's difficult to avoid getting attracted to your co-founder. You'll be going a lot of places together. I've shared the same hotel & bedroom with my co-founder for months. And you tend to share all secrets together, very much like a married couple, if not more so.
There's no way to know how this will work out. Could be great, could be a disaster. If you give it pass, you might end up with regrets. It's a big gamble no matter which way you go. If you're certain that feelings are mutual, it would seem that there's one person whose opinion matters more than random strangers on the internet.
Disclosure: haven't done this but I have a girlfriend of many years and a startup so here's my 2 cents.<p>Both these things are hard and as such both will have a hard time succeeding but they're both worth the trouble so I say go for it with these considerations:<p>You need to have an agreement that you will be professionals first while at work and that at work, work comes first. Your company is very important to you and emotions(good and bad) will tend to take precedence but you have to be cognizant of your emotions and try to separate them. You have to.<p>For this reason, have an agreement of sorts, a kin to a prenuptial agreement. Answer questions like if things go wrong and you can't work together anymore, what happens then? There's a reason companies have strict policy for workplace relationships and how they ought to be handled.
Just make sure that you do not have a 50%-50% ownership arrangement (<a href="http://www.delawareonline.com/story/money/2017/07/17/transperfect-impasse-sale-looms/484415001/" rel="nofollow">http://www.delawareonline.com/story/money/2017/07/17/transpe...</a>)
Your pre-existing relationship as cofounders means that pursuing things will have costs on people outside the relationship itself. In particular, investors and employees. You should have a plan for how to communicate this development.<p>This may be a little old-fashioned, but I'd take a serious look at getting <i>married</i> before seriously dating. You already know each other well and trust each other, and it appropriately signals the seriousness with which you're approaching things.