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The Founder Dating Playbook (firstround.com)
164 points by feifan on Oct 1, 2019 | hide | past | favorite | 43 comments


My best co-founder is someone who I would almost certainly spend little or no time with outside of work. Our personalities are polar opposites. Together we've bootstrapped a $2.5M ARR business in 16 months.

Some thoughts:

- Cofounders are high stress and high time relationships. You want to find someone who doesn't burn everything down every time they get stressed. Finding someone who deals with stress in a healthy way is huge.

- Don't let the small things get in the way of the big things. You have to have tolerance for each other's mistakes. This was a huge problem for me and a previous cofounder. The way I handle it now with my cofounder is we set a price on mistakes. If you want to take a $1,000 risk, we don't even discuss it. A $10,000, we talk about.

- I generally prefer people driven by discipline than passion. Passion cracks under pressure. Discipline keeps working.

- Ego. Find someone who doesn't think they're god. I know in the SV hype messiah driven world of startups everyone tries to be the prophet. Avoid these people. For me, someone who has confidence but not arrogance is huge.


All good tips and ones I've learned over time as well. Particularly like the "set a price on mistakes" part. I think communicating there is a healthy amount of mistake-tolerance does wonders for long-term personal and professional growth.

Just for curiosity, how do you think you and your co-founder would proceed if there was misjudgement about a $1,000 risk that turned into a $10,000 one?


Of course, we'd talk about it. If a mistake blows up we have to talk about it.

The point I'm trying to get across is that you have to be willing to let your partners make mistakes. Also, you have to trust that your partner is going to learn from their mistakes. I like adding a dollar amount to it because it gets you in the right mindset of focusing on important things. I think as a cofounder, it's your job to step in if you think someone's going to take the company over a cliff. Otherwise, give each other room to grow. Everyone in an early company is required to learn aka make mistakes until you stop making those mistakes.


Is it fair to say if you misjudge the magnitude of an investment you have a retrospective?


Absolutely. We're still pretty small so we don't use formal names or structures but in essence yes.


I thought the difference between arrogance and confidence is being right.


A person who is confident speaks authoritatively and, when asks, backs up their statements with evidence.

A person who is arrogant speaks authoritatively but tries to weasel out of justifying their statements by using logical fallacies, deflecting attention to others or other matters, or bullshitting.

There's also a general attitude component that seems pretty common. A confident person doesn't need to put their ego on display for everyone, because they believe their positions have a firm foundation in data or fact to stand on. An arrogant person will tend to engage in a lot of bluster and undeserved self-promotion to distract from the lack of quality of their ideas.

Both confident and arrogant people can be right and wrong at various times. I'd like to believe the confident person is generally more right than the arrogant person, but that isn't necessarily the case. Having worked for and with both types of people, I would rather work for someone confident, even if there was an arrogant person who was right more often. The stress and disgust that comes with working with arrogant people just isn't worth it to me.


Confidence and arrogance of two sides of the same coin, they're not mutually exclusive and people can be varying degrees of both. The biggest difference is always in the eye of the beholder.


Hard disagree. I think of Bob Sutton's quote a lot (I don't think its his quote, he just use it a lot as well) : Speak as if you were certainly right, listen as if you were certainly wrong.

You need confidence to assume your choices, sell your ideas, and take risks. You need to avoid arrogance to avoid mistakes, learn, and build a healthy team


It's hard to describe but easy to observe the difference. I'd put it like confidence is believing you're correct and arrogance is believing no one else could be right.


> someone who I would almost certainly spend little or no time with outside of work

That might be your experience, but the best cofounder for me is one I can share everything with. At work or outside, we're always in sync. I don't know how you would pull through difficult moments with an ice wall in the middle. Being able to see the worst of each other is how you really know somebody.

> Finding someone who deals with stress in a healthy way is huge.

Agree.


For me, I like the separation. I really appreciate being able to have a bad day at work but a good day at home. When you're starting a company, it will consume your life. It will also alternate from thinking you're on top of the world to feeling worthless.

When you're starting a company with someone, you're going to spend tons of time together and share personal things anyways. In some ways, I think it's hedging the emotions and keeping things about the business. I think you can work with someone and become friends. I've failed and seen others fail trying to turn a friendship into a business.


Yeah totally agree on the reverse direction. It is very rare to have a friendship that also becomes a business relationship, at least with my network. You just become friends for very different reasons.


To include few more I avoid,

Entitled - Call the manager type,

Manipulative, Paranoid, Narcissists etc. [1]

[1]:https://hitstartup.com/types-of-people-to-avoid-having-in-a-...


Any chance you can say what company you're working on, either publicly or privately?


A hemp flower cbd brand, Plain Jane (https://tryplainjane.com)


How'd you meet your best cofounder if you don't mind me asking?


She was friends with another cofounder. The other cofounder left the company, leaving us two. I got incredibly lucky to have a cofounder to turn out to be the person she is. Things could've easily gone very differently.

The advice I've heard is that you want someone you previously worked with.


I mean it's an interesting idea that someone who hasn't actually founded a successful company with a co-founder has a "playbook" for finding a co-founder.

They've been working together 5 months and now that warrants the proclamation of a playbook?


Marketing materials, any eyes on the site could translate to viewing more of the site. Viewing more of the site will slowly increase page rank.


This other piece is on the front-page of HN at the same time. Coincidence?

https://news.ycombinator.com/item?id=21131704


You must be new here. This same attitude permeates all of tech, especially SV, where folks constantly tout their non-accomplishments publicly. Every idiot is giving advice because every idiot is looking for some.

And there are a whole lotta idiots in SV smelling their own farts.


I agree 100%.

If only the news article/stories followed up what they had touted after two-years it would make a good journalistic report. Or even trying to balance the article by acknowledging the drawbacks of the the system they are advancing.

I like to read articles that debunk the previous hypes and put a retrospective article detailing what went wrong.

For e.g. MOOCs were touted as game changing to the online education and after years, it hasn't really 'disrupted' anything.


This affirms my experiences with getting to a venture-funded deal. The stylistic elements of this piece, not its content.

Someone who can speak the product managerese--who takes 7,000 words to say something and look thoughtful while doing it--is so essential to getting to a venture-funded deal.

Being on the other side of the process she describes sucks. Like nobody wants to be part of this imaginary, psuedo-scientific competition. In reality she just acquiesced to whatever the 6th person demanded. The process wore her down.

If the process didn't wear her down, there would be no deal, because the deal only occurs when the product manager character moves along.

In quintessential product manager form, the process disguised a completely emotionally-driven decision by providing a post-hoc rational for it.


I find it strange to not just use your personal network to find somebody. I feel like this whole “detached cofounder” thing is for people making an implicit agreement that you both intend to screw each other over if you ever get the opportunity.

But if you’re a “product person” I suppose you need someone to actually build the MVP for you so you can’t really do that part alone.

Personally I’d rather do it alone than make a huge decision like this with some random. Passing an interview is easy if you know what to say, would be too hard to trust someone to not just try to get a free ride. And it takes a really long time to truly know someone, but it also seems crazy to me to spend up to half a year “cofounder dating” before you get to work; that seems like pseudo-productive procrastination more than anything


I've been the subject at least one of these cofounder "dates" and the worst part is it was done under the auspices of speaking to someone who's found a modicum of success in a startup.

The introduction given to me was that it was a person with an idea who wanted a sort of "mentor" in the space who can help navigate the technology aspects. The actual date consisted of them pitching me and gauging my interest.

I was a little turned off. So my suggestion to the author of this article is to add "Be honest about why you're at the coffee shop."

I did see this, though:

> “‘Where do I find people?’ is one of the biggest questions I get when people ask me for advice. There isn’t a ‘Tinder for co-founders’ app that everyone is on. Sourcing is hard,” says Lin.

Anyone up for a new project? :)


I’m pretty sure that’s basically how accelerators work, unsuccessful accelarees (?) quickly become early employers or cofounders of the more successful ones


> Anyone up for a new project? :)

Ah, you mean good old 7885 Attend receptions, dinners, and conferences to meet people, exchange views and information, and develop working relationships.


>I find it strange to not just use your personal network to find somebody.

Your sentiment is similar to the top-voted comment in a previous thread about this.[0]

It seems insane and uncomfortable because we're using labels for people like "random stranger". But it's a paradox: before people become friends, they're strangers to each other. So how did they ever become friends?!? Before someone was in your personal network, they were previously _not_ in your personal network? So how did that status change?!?

By meeting new people and seeing what type of interactions happen. There are no guarantees in life. All we can do is try to meet new people.

Not everybody has a "cofounder" already existing in their personal network. (E.g. didn't go to same school at Stanford and not a coworker at a company job.) In that case, they have to grow their personal network with like-minded people who might be a cofounder.

The "alternative" of starting a solo business may be less realistic and higher risk of failure than trying to find a cofounder that shares the same goals.

[0] https://news.ycombinator.com/item?id=20266463


Random stranger may be a label but it’s also an accurate description.

I guess to me, it seems strange for someone, especially in tech in the Bay Area, to want to be a founder but have nobody in their personal network that they would like to work with also interested in being a founder who reciprocated that feeling. That is wildly different from what my social circle looks like, and I didn’t go to Stanford. In fact it’s so different that I would characterize it as somewhat of a red flag (very weak personal network? hard to work with, not likable? lazy? little tech exp?); of course, two people in similar situations probably wouldn’t see it that way and that’s fine, I’m just sharing my perspective.

I don’t see why starting a solo business is unrealistic unless you lack some core competency in the business you are trying to start. In that case, yes you would need to start a different business. If you have a poor network, have a hard time finding a cofounder, and also have a hard time finding something within your core competency then you should probably be re-evaluating why you’re starting a business at all


>Random stranger may be a label but it’s also an accurate description.

Right, and I'm not debating its accuracy; I'm saying that somehow the status changes from "random stranger" to "acquaintance/friend/partner". However, one sometimes has to go out and make an effort (meeting new people) to allow those changes of relationships to happen.

>, to want to be a founder but have nobody in their personal network that they would like to work with also interested in being a founder who reciprocated that feeling. [...] I would characterize it as somewhat of a red flag

Again, you calling it a "red flag" is fair. But the key is can someone attempt to change that red flag? E.g. the author of this article Gloria Lin went on "cofounder dates" to overcome that instead of just looking at her personal network as a static list of people and just give up.

>I don’t see why starting a solo business is unrealistic unless you lack some core competency in the business you are trying to start.

I'll take myself as an example... I hypothetically could start a solo business but none of them I can do are interesting to me and therefore I'd fail due to losing motivation. I want to start a B2C business and the one I have in mind is complex enough that it requires a very strong partner (and possibly even 3 cofounders). Most everybody in my personal network is risk-averse and not the folks I'd ask to quit their jobs for an uncertain future. But the limitations of my personal network doesn't squash my desire to build a B2C business.

Drew Houston didn't go on a cofounder matchmaking website but it took a friend-of-a-friend to find his cofounder (Arash Ferdowsi) for DropBox.[1]

But yes, you still have to cautious because the business relationship can fall apart -- even among coworkers that supposedly knew each other for years before starting a company.

[1] https://www.bbc.com/news/business-44766487


"I guess to me, it seems strange for someone, especially in tech in the Bay Area, to want to be a founder but have nobody in their personal network that they would like to work with also interested in being a founder who reciprocated that feeling."

I think it depends a lot on how you got your experience in tech. If you got your stripes via a CS degree and several years at an established company or two in a tech hotspot, then yes it's perhaps kind of strange if through all of that you never developed a network with any potential co-founders in it. Developing a network is one of the primary benefits of taking this path.

But if instead you were self-taught and became an expert through contracting and/or doing your own projects, you could easily not have a network with many potential co-founders in it despite being great at what you do. This can also be the case in spite of having an otherwise strong personal network--you might know tons of interesting and accomplished people who have absolutely zero interest in startups.


Here's my story about looking for a co-founder for Polar:

https://getpolarized.io

I'm basically trying to build an integrated reading environment for people like researchers and students. You can kind of think of it like IntelliJ or Visual Studio but for books.

I shipped an MVP on Hacker News and right now we have about 5000 MAU. And our users LOVE us.

I just found out that Roger Craig. One of the Jeopardy champions used Polar to win Jeopardy.

https://superorganizers.substack.com/p/how-a-jeopardy-champi...

Now, being a solo founder is tough. A lot of VCs will hold it against you. However, one of the number one failures of a startup is having a bad co-founder.

My strategy has been to be VERY conservative here.

I identified five co-founders but just haven't had a good fit.

I think my biggest advice is to trust your instincts. Unless it feels perfect and you've been working together for a while don't pull the trigger.

My plan now is to have sort of running co-founder search and bring them on more as a senior hire with adequate compensation if I'm successful in finding them.

It's hard though. I'd go so far as to say it's harder than finding a wife.

They need to have your back at all times but unlike a marriage there's no actual love backing the relationship.


My friends outside of work aren't really technical, nor do they have any interest in startups.

I've tried a handful of those founder dating sites, gone to meetups, user groups, met for coffee/beers, and even travelled to meet up with other like minded folks and try to get a feel about who would be a good fit. With the importance of getting the cofounder right, I almost always left feeling like it was too much of a leap to take with someone I just met from some website or meetup.

But when I look at my own friends, there aren't any of them I would conceivably work on something significant with. Maybe I need to find some new friends, or maybe its a volume game.


I'm in the same boat as you except I haven't started this dating game yet. I know no one in my (admittedly small) network of friends and acquaintances, who is willing to drop everything and create a startup with me. I'm not in the SV so that doesn't help.

I'm trying to come up with a strategy including meetups. But how likely is it that single founders going to these meetings with an idea of their own, are going to give up on it and join someone else? And if someone is going to these meetings without a strongly held idea, then what does that tell me about their intention (free ride?).

The only way I can see this working is if 2 founders meet that have an idea so close that they can see merging them. How likely is that considering constraints of time and location...

I'm starting to find that the hardest part of my startup is going to be the people factor, which I will say is my biggest weakness. I guess it's good that I'm aware of it at least.


To find cofounders, may I suggest that you add in your profile your interests and some ways to reach out to you (e.g., email)?


If you're technical, I think anything where you actually get to work on projects with people is going to have a lot more potential than just talking. So hackathons, open source, and other things in that vein.

The difficulty here is given you find another technical co-founder, at least one of you needs to be willing to jump hard into sales, marketing, and administrative stuff. But assuming you have that, two strong devs who enjoy working together can make for a formidable team, and it doesn't really take that big of a project to know whether you like working with someone.


Just like finding a spouse is an art, there’s no science behind finding a cofounder. You might a cofounder who does not fit the bill discussed in the thread or the article. We get together to make something work with equanimity.


I don't think finding a spouse is an art. You don't typically find a (good) spouse by actively looking for one.


So how is it different in case of cofounders?


Good article, I wrote a paper a while ago on that subject for startup research based on my experience with startup weekend and the often asked question on where to find a cofounder... I applied these principal for myself and Found 3 great co founder and launched 3 different ventures (one is a cash cow / one is venture backed / one is a non profit)

Paper->

https://www.joebarich.com/uploads/2/3/6/8/23683720/co-founde...


Speaking of the _other_ dating... I had recently been messaged by a dating coach on LinkedIn who specialises in software developers.


I didn't flag this article, but I consider it very inappropriate. Romantic or sexual analogies should not be used in the workplace or startups. It's just the wrong word to use.




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