First Dates and One Night Stands for Co-Founders

Always wear a tux on the first dateBefore you and your co-founders step up to the alter and say “I do”, it’s a good idea to get to know each other a little first. Maybe even play a little footsie.

I’ve been searching and searching for good advice on the subject and consistently come up empty. There’s plenty of advice on how to split up equity, qualities to look for in a co-founder, and even the occasional article on places to go to find entrepreneurs.

Why is there zero information on how to vet them?

The typical article seems to suggest a good conversation will do the trick, presumably because you’ve just dosed your co-founder with sodium pentathol and wired him to a lie detector.

While there’s no perfect answer for this, just as there’s no perfect first date, I’d like to suggest a few options.

(For the record: The perfect first date is always in black tie. Everyone looks good in a tux.)

Open Sources Projects

You might think that an open source project is only for vetting technical guys and gals, but I can’t think of a better way for an MBA to prove their worth than contributing to an open source project. It may be a niche market of engineers with a low price point and low feature expectations, but it’s still a market.

When it comes down to it, the principles of customer development are the same whether you’re getting paid for a product or not. There is always a price tag that’s associated with user adoption even in free products. For example, Facebook and LinkedIn require a significant investment of time to get your profile looking nice. That time is the purchase price, open source is the product, and every open source project should be searching for product / market fit.

A keen business person should be able to significantly contribute to even a purely technical product by talking to customers, defining the minimum viable product, figuring out when to pivot, developing a minimum viable strategy to popularize it, etc. A really savvy MBA will find a way to turn your open source side project into a business.

Volunteer Work

I admit that I’ve only started giving back to society with volunteer work recently with the BUILD entrepreneurship program. Now that I have, I can’t imagine not doing it.

Are your core goals and values aligned with your partner? Try ladling soup for a few hours with them and you’re sure to find out.

They can’t deal with the smelly homeless guy? How are they going to deal with a pissed off customer?

Admittedly, this may not work if you’re in a pure for profit business and you want to find someone that is as cutthroat in business as you are. Then again, are you really going to be able to trust someone like that enough to work effectively with them in close quarters for a couple years?

There are plenty of volunteer opportunities that don’t require a long term commitment. Pick something for a weekend and see if your co-founder is willing to lick stamps for 48 hours. If not, will they have what it takes to sell door to door or do manual data entry when the going gets tough?


There are some great events like Startup Weekend which throw a bunch of people into a room together and let them experience the joys and heartbreak of a startup in 48 hours. It’s a sleep deprived and coffee driven bonanza with moments of brilliance.

[Disclaimer: I’ve organized a Startup Weekend and spoken at others.]

Many people go to them to find co-founders and pitch their ideas. I think another idea is to try out your new co-founder. Take them to a Startup Weekend or other similar event such as Hacks and Hackers storytelling / hacking event and find out if you can really work with them.

You can join someone else’s project for a weekend and find out some very valuable information. Can your co-founder work in a larger group? Can they handle pressure?

Most importantly, can your co-founder work in a team towards a goal, even if they haven’t 100% committed to that goal?

Because there will be times when your co-founder is staring at an empty bank account while you’re scrapping around for angel funding.

Will your co-founder bail at the first sign of trouble or stick it out for the long run? If they can’t make it through 48 hours, you might want to keep looking.

Discussion (10 comments)

  1. Jeremy says:

    Good ideas! I also suggest a potential co-founder work on the project with the original founder for perhaps a month: there’s nothing like working on it to see how they’ll do working on it! Then after a month, if it’s a good fit, they work out the partnership details. If it doesn’t work out, they simply thank each other and part ways.

    1. Tristan Kromer says:

      Great idea. I think the only issue is that you have ownership conflicts or need some sort of rudimentary operating agreement in place. That becomes a bit like a prenup before the first date.

      I’ve also seen a lot of “I’ll hire your for a month.” That seems like a fair way to go as there is no real argument at the end. The person either gets paid or is a partner.


  2. Mike says:

    Hell, I lived with one guy and we still ended up being horrible business partners. The trick I think is this:

    1. Make sure the company is something you really, really believe in
    2. Make sure you are really, really okay with the ownership split and who the CEO is (because one of you will need to become the CEO)
    3. Make sure you’ve got lots of funding, at least lots for whatever your costs are going to be and it will be: 50% salaries, 25% rent and 25% everything else.
    4. Agree upon when to dump the whole thing. Hanging on the bitter end is far more bitter than you can imagine.

    1. Tristan Kromer says:

      Great points! A lot of partnerships start because old college buddies get together and there are many famous examples of the working out.

      However, skill sets an working styles might not be the right fit and the friendship can conceal that. I working with a friend of mine on a short project (actually I hired him as my lawyer) and it put serious strains on our relationship. I think the assumptions that we have when dealing with people we know well can cause serious issues and cause us to neglect our responsibilities in a work context.


  3. Withheld says:

    I am in business with my Dad and we do awesome. However, there was another business that we started later and that partnership didn’t work. The roles and needs were different.

    Luckily we still have the first business and continue to work well together in that one.

    So, I think Mike has a point about working on the specific project for a while before signing the deal.

    1. Tristan Kromer says:

      Kudos to you for recognizing the issues and not letting it get in the way of your other business or your relationship. How did you go about finding someone new? Did you consider a number of different people before deciding to work with your father?


  4. love_startup says:

    Great article. Wish I had read it 5 years back!

    My learning:

    1. To have a positive partnership, the rules of working together need to be established very early on.
    2. Who is responsible for what facets of the business? what decisions would be made jointly and what would not.
    3. Complete disclosure on ownership percentage and salary.
    4. Lastly, have regular (i would recommend weekly), state of the company meeting between the co-founders so everyone is on the same page.

    1. Tristan Kromer says:

      Thanks for the kind words.

      I always have a hard time with setting the rules. My OCD self completely agrees with you and my partners and I have had very thorough discussions on most issues.

      Still, a part of me equates building any relationship to dating. And how often do you sign the prenup before the first date?

      I really like the consistent theme running from points 2-4 – honesty.


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  7. Tara says:

    Thanks for the link to BUILD – I’ve been looking for volunteer opps lately where I can actually make a difference. Happy to see “entrepreneurship” is a skill that can be donated.

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