Pirates ➡️ Navy

Early-stage startups are a lot like pirates. They both lack formal processes, and are willing to question and even break rules to “steal” from incumbents (market share and booty respectively). This adaptability is critical in the early stages of building a great company.

if you succeed as a pirate, your stockpiles of treasure will grow. The territories you control will widen. You’ll need more manpower to protect all that booty and patrol all that terrain. Once you move from the early stages of blitzscaling to the Village (100 - 999 employees), City (1,000 - 9,999 employees) and Nation (10,000+employees) stages, you’ll lose the ability you enjoyed as a pirate to communicate and collaborate effectively on an ad hoc basis, and you’ll have to trade in your Jolly Roger for the flag of legitimate, disciplined navy.
~ Reid Hoffman On Pirates & Navies

This is an excellent essay on how team cultures evolve from the early days of an organization to later stages.

Most startups recognize the value to being small. Small means innovation, nimbleness, focus, and outcome as opposed to process, internal communications, and meetings. :pirate_flag:

There is irony here, bc when Pirates are successful they must become the Navy to scale. Successful leaders realize that they need to keep the positives of staying small, while building in the virtues of bigness. :ferry:

For many startups, there is a ton of value to being small - small means agility, innovation, and outcome focus. Getting large means keeping the positives of staying small while building in the value of bigness (repetition, process, infrastructure). :pirate_flag: :fast_forward: :ship:

Maybe I’ve never successfully walked that line, or maybe I’ve been on teams that transition from Pirate to Navy too soon… but I’ve always felt like I’ve identified a bit more with Pirate startup culture than Navy startup culture. Piracy is agility, and in a networked world, agility is strength. Piracy is hunger to get shit done, and when agency is alpha, that is strength.

I’d welcome stories of successful pirates, or pirates scaling their culture, in the comments below. :pirate_flag::sparkles::point_down:


I’ve learned that as a pirate - you may need to get comfortable with a bit of infamy. Sometimes you just gotta ride the lightning on that one to be a good pirate.

When I introduced proUBC to the world - I knew it would not be popular a crowd of people who had vested interest in another commercial, non-open source product from a competing project sort of doing the same thing. But I felt it was the right thing to do as open source even if it would be hard to do.

As a pirate at heart - I ultimately valued giving developers and companies in the SAP ecosystem freedom to take a choice how they would adopt Ethereum. To me personally - it only made sense to have competing open-source equivalents to things that would otherwise bring users total vendor lock-in when using Ethereum for B2B purposes.

It is an interesting article, although it doesn’t quite capture the dynamic “living” structure envisaged for larger organizations / organizings by org design theorists.

I was party to the development of the Responsive Org movement a decade ago with some lovely people, not least Yammer co-founder Adam Pisoni. And organization-as-organism and business-as-biology best sum up the heterarchical structures we explored together.

This wasn’t just some collective chin rubbing. We had many corporate representatives in the room with the remit to experiment within their own organizations and report back, and we analysed more than a few inspirations out in the field.

The military theme Hoffman adopts here is not unusual, and it’s not unusual to imagine a regimentation of military organizing given its heritage. Nevertheless, to this day too few recognize that various military organizations are in fact at the vanguard of moving way beyond the organizational form with which they are synonymous and that informs Hoffman’s article.

Check out Retired Gen. Stanley A. McChrystal’s take in this Foreign Policy article. (The link below is on the Web Archive and not then behind a paywall.) Perhaps McChrystal’s most famous quote is:

It takes a network to defeat a network.