Your startup will fail if you mess this up ??

Cofounder relationships are among the most important things in the entire company and if that gets messed up, which is pretty common, everything else starts to crumble. The success or failure of your startup has a lot to do with the success or failure of your co-founder relationship. If you enjoy your 0 to 1 also depends a lot on how you & your cofounders gel together.

? Starting a company with someone is a big decision

You’re committing to a 5-10+ year journey, side-by-side with your co-founder(s). A number of founders told me they jumped into a co-founder relationship very quickly, without knowing the people well and no due diligence. You’d think a decision of this magnitude would be done more thoughtfully, but that’s not always the case. I think it’s because founders are an inherently optimistic bunch, who believe they can build something from nothing and change the world. When they meet likeminded people, and they collectively get excited about an idea, they jump into the partnership.

? Finding a co-founder: A bad reality show?

Some accelerator programs promote the idea that you can find a co-founder quickly and magic will happen. It can work, but in a lot of cases those founders break up.

I spoke with a few founders that went through these types of accelerators. They felt a lot of pressure to “pair up” quickly and get to work. Some said it felt like a reality dating show.

We need to create more opportunities for people to connect, get to know each other, and ultimately co-found companies together, but it doesn’t change the fact that finding a match (that will survive and thrive) is incredibly difficult.

? “Let’s start a company together,”?shouldn’t be the first step in the process.

Even if you know the person (and we’ll talk more about working with friends in a bit), you should consider dating your co-founder(s) before committing.

This isn’t always easy to do. One of the big challenges is figuring out what to work on. Some founders I spoke with worked on “side hustles” together, to see how the working relationship functioned. Others already had an idea for a startup, but instead of incorporating and locking it in, they started working on it together to see how things went.

In both cases you still need to set expectations clearly, and this is a big part of figuring out if you can work with someone as a co-founder.

A lot of the big issues hopefully emerge during this dating period:

• Core values / purpose (why are you even doing this in the first place?)
• Ambitions / goals
• Time commitment
• Financial expectations (both in terms of what you’re investing and what you’re expecting out)
• Decision making approach
• Etc.

Unfortunately dating for a long time is also risky. If you start to build something real, launch in-market, etc. and there’s no legal structure behind it, breaking up can be even more complicated. I dated my cofounder for 3 months before officially getting onboard.

Some founders date and never build anything. They ideate, brainstorm, hang out, etc. — all of which are good things to do — but this “work” doesn’t translate into truly understanding what it’s like in the trenches with someone. At the same time, dating before starting a company isn’t just about the work itself, it’s about finding alignment on everything else (including the items listed above.)

? Can you do due diligence on a potential co-founder?

Yes. And you should.

Don’t take a person’s public reputation as absolute truth.

? Should you start a company with someone if you have doubts?

Probably not. Doubt has a way of creeping in, growing and then consuming you. One founder I spoke with said:

“Having doubts about a co-founder is a killer; this stuff is difficult enough, so you can't afford to expend energy on worrying about how your co-founder is performing and second-guessing what they are doing. Also, those doubts don't disappear by themselves. You have to face and hammer them out head-on and early. The issues that led to us splitting up were the same ones that we had three years ago that weren’t formally resolved.”

If you do have doubts, you’ll need to talk about them with your co-founder (or soon-to-be co-founder.) Burying this stuff won’t work. Having hard conversations is part of the job.

? Should you start a company with friends?

This topic came up a lot when speaking with founders. Some were 100% for it, others had bad experiences. So the answer is (not surprisingly): it depends.

With friends, there is inherent trust. And trust is critical to succeeding with co-founders. The challenge is that “friendship trust” is different from “working relationship trust.” In a working relationship as co-founders you have to be aligned on a lot more than you do as friends.

One person I spoke with started her first company with one of her best friends. It seemed like an obvious choice. But since they were already close they didn’t spend time aligning on the core issues they’d face, which ultimately led to the startup failing.

“I didn't take into account the real need for complementary skills -- I just thought of starting a business with my best friend.?This doesn't necessarily translate well.?Much like any personal relationship, it's vitally important to determine outcomes and expectations and have some hard conversations from the start in order to avoid any misunderstanding downstream.?I realized after starting the company that he didn’t have the same level of commitment and willingness to hustle that I did.”

Y Combinator prefers founders that have worked together, which makes sense. Personal relationships aren’t enough. You might like someone as a person but not as a co-founder.

Friendships come with baggage. In some cases the trusted relationship you’ve built as friends could strengthen the co-founder bond, but that’s not always the case.

Whether you start a company with friends or not, you still need to ensure transparency and honesty in the relationship.

? You might do all of this work in advance and still fail

No one wants to start a company on the wrong foot. But getting perfectly aligned and trying to deal with every potential issue that may arise before you even start is equally difficult.

One founder told me that she spent an enormous amount of time with her co-founder aligning on mission, values, responsibilities, etc. They wrote it all down. They talked about and figured out their communication approaches, strengths, weaknesses and so on. They did everything you’re supposed to do up-front before becoming co-founders.

The founders still didn’t end up in a good place when things got tough:

“When it was going well I felt like it helped a bit, but it also felt like overkill at times.? Focusing more on team dynamics than on product-market fit.?Ultimately startup failure is hard (and my cofounder was at risk of losing a lot of money), so it felt like all the good work and communication we did early on ended up not mattering because the fear/greed set in and the bad behaviours came out.”

When you start a company you are in a honeymoon phase. It doesn’t last. Eventually reality sets in, you realise you’re in for insane ups and downs, and a lot of people aren’t cut out to survive or thrive through the intensity. You may have spent hundreds of hours attempting to build a strong relationship and set yourself up for success, but when the going gets tough, people can get nasty.

? The co-founder relationship takes constant work

Building a startup is incredibly stressful. And that puts a lot of stress on the co-founder relationship. There is absolutely no way you start a company with someone and never disagree or fight. It’s almost inevitable that you’ll ask yourself at some point, “Did I make the right choice starting this company with so-and-so?”

You should not pretend it’ll be smooth sailing.

While speaking with a bunch of founders, I got a number of suggestions on how to deal with these issues. Of course the standard stuff applies: always communicate, don’t hold things in, be transparent, and hold your co-founder and yourself accountable. But here are a couple other ideas:

• Go on walks together: Although this isn’t something I do with my co-founder on a consistent basis since we live in different cities, we do it every time we're in the same town and this changes the dynamic of the conversations and puts people in a better head space.
• Go out for drinks/lunches/dinners together: Going out, being able to hang out and engage in conversations outside of work works like magic. This is how you will build actual relationships and get to know what is working out and what isn't. Make this a priority right from the get-go, and see drastic changes happening.
• Care about what they care about: Take an actual interest in their life. Care about what they care about, care about the people they care about and care about the ideas they are passionate about. This is a game changer. It is part of your job to get to know your cofounder and this will make your relationship rock-solid.

“Fundamentally we liked each other and had a ton of respect for each other. We had fallings out, things got hard, things got harder, things got harder still. We remembered that tending to our relationship came first above all else. We made time to go for walks every week to have focused time with one another. It was a practice that made a massive difference as the years went on.”

When things get tough, it’s easy to forget that the person on the other side of your frustration is human. They have feelings. They’re imperfect. And they’re probably struggling as much as you are, even if you believe they’re to blame.

Your relationship with your co-founder is a professional and personal one. It becomes very difficult to untangle the two. And you might argue it’s the actual integration of the personal and professional that can make a co-founder relationship so strong, unlike most other relationships you have in life. When you’re clicking on a personal level and cranking at a professional level, co-founders can accomplish a ton.

In my experience one of the most important roles of a founder is lifting up your co-founder when they’re down.

You should know when they’re feeling low, when they feel like there’s a boot on their neck. You might also feel it, but if you can muster the strength to carry the burden for a bit, and encourage your co-founder through a rough patch, they’ll (hopefully!) do the same for you.

Overtime, me and my cofounder have been able to build a rock-solid relationship that has a lot of mutual respect, good dependency, and immense trust. We're very good friends, enjoy each other's company, have complimentary areas of expertise, and trust in each other's judgement. We've been able to figure out ways to resolve differences in a way where it does not feel like there's a difference being settled. All of this only happened after our fair-share of rough patches, working with other good as well as bad folks, etc. At the end, you must value the person you're building a company with and enjoy their company on this stressful and lonely journey of building a startup.

I've made it this far without comparing a 'cofounder relationship' to a 'marriage' and 'building a startup' to 'raising a child'. It was not easy.

I hope this helps and you build a great venture.