My Public Pensieve

Building an awesome cofounder team…

If you ask Patrick and John Collison what their mission is with Stripe, they’ll say they want to “increase the GDP of the internet.

They do this directly (by creating better online payments infrastructure) and indirectly. One of the indirect ways Stripe increases the GDP of the internet is via their ownership of IndieHackers.com.

At Indie Hackers, founder Courtland Allen is helping founders all over the world get the advice, support and feedback they need to build more successful businesses – thereby indirectly increasing the GDP of the internet (and Stripe’s potential customer base too).

I’m a big fan of both Courtland, the Collison brothers, and their goal. And I’ve been thinking for a long time about how I can contribute to that goal without having to be a Stripe employee*.

Finally, I’ve found a project I want to work on which will contribute to that goal.

A project based around a real pain people experience, that:

  • if solved, could meaningfully increase the GDP of the internet
  • doesn’t have a good solution right now
  • I’m a domain expert in
  • I’m passionate about and can see myself working on for 5-10 years

That pain is how to build and maintain a successful cofounder relationship.

I’ll be putting together a more detailed explanation of the size of the problem in the near future – but a quick summary is that bad cofounder relationships are one of the main causes of otherwise successful companies failing in their early years.

Even a small improvement in this area would yield a significant increase in the GDP of the internet – and I’m sure I can do a lot better than just a small improvement.

I want to work on this more transparently than with previous projects.

Right now I’m not yet ready to share all of my thoughts in detail, but here’s a rundown of the main cofounder problems which kill startups, and my current thoughts on how best to solve them


Killer #1: Finding an awesome cofounder

It’s easy to find a cofounder. But it’s super, super hard to find a really competent cofounder, make sure you have cofounder fit, and convince them to work with you.

I have a lot of thoughts on the details of this challenge. There are lots of moving pieces.

But there are basically three main hurdles founders fall at:

  1. They don’t know where and how to attract the interest of high-quality potential cofounders in the first place
  2. They do a poor job of qualifying for technical ability and/or cofounder fit (ie will we work well together)
  3. They do a poor job of convincing these excellent potential cofounders (who have many options on the table) to work with them

Potential solutions:

  • I’ll go into a lot more detail about why this is important in the near future, but I think we need a screening system/cofounder matching service which is human-powered and pay-to-play. More on this coming soon
  • Founders need better education (content) and support (maybe consulting) in qualifying potential cofounders. It’s really hard for technical founders to assess how capable someone with a sales background is, for example
  • There needs to be more educational content and templates for founders on how to convince their ideal candidate to say yes!

Killer #2: Death by lack of clarity

This is the big one.

I have a list of 50+ variables which, if you don’t have a clear agreement on them in your cofounder relationship, can easily destroy the startup.

They can basically be sorted into three subcategories:

  • What happens when someone leaves?
  • Who makes which decisions?
  • Who owns what?

There’s also a larger, meta-problem here, which is that founders often aren’t comfortable or don’t understand why they should be clarifying these questions upfront before they become a problem.

Potential solutions:

  • We need to educate founders on why it’s important to clarify these uncertainties upfront and how to do so
  • There needs to be an easy to implement, standard cofounder agreement template which is actually useful
  • There needs to be a broader willingness in the founder community at large to talk about their cofounder relationship problems. At the moment, we sweep this stuff under the rug and newer founders can’t learn from our mistakes. This has to change (maybe via interviews/a podcast)

Killer #3: Death by poor communication

This is the area I’ve struggled with the most as a founder, and is trickiest to get right.

I’m not going to go into detail on this here. But I think most of us who have cofounded a startup before understand just how vital it is to have regular, structured, productive communication and mutual trust within a cofounding team.

And just how underestimated/hard it is to make that happen.

Potential solutions:

  • We need actionable, educational content on how to build and maintain effective cofounder communication
  • There needs to be an easy, actionable framework cofounders can use to enable this. We shouldn’t all have to reinvent the wheel
  • In some cases, cofounders could use regular mentoring/counselling sessions – especially when they are a two-person team or the relationship is already fragile

Next steps…

Over the coming days and weeks I’ll be thinking hard about which of these problems I tackle, how, and in what order.

You can follow along and get early access/discounts to whatever I come up with first, here:

I’d love to hear your feedback, thoughts and suggestions via email.

Two questions I’m thinking particularly hard about right now are:

  • (How) can I monetise this? Founders are difficult customers and don’t like paying for stuff, regardless of the value
  • Ignorance is a big problem here. If I’m going to succeed at reaching founders at scale and making them understand just how important this problem is, then the founder community at large needs to become more open about their less-than-perfect cofounder relationships. I’m thinking hard about how to make this happen

Watch this space…

*I’m sure working at Stripe is amazing and they have way better candidates than me applying – I just don’t want to work for any employer right now.

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