Building a Positive Sum Startup Community DAO - Season 0 Retrospective
@colart's welcome to us at our end-of-season team retreat
@colart's welcome to us at our end-of-season team retreat


That’s how our community leader Colart Miles welcomed everyone last week as we kicked off our end-of-season team retreat to reflect on what we’ve achieved in our emerging startup community support DAO, and plan out where we want to go next.

And what a fitting way to sum up our efforts and our ultimate vision in creating a web3 community to help startups find a more open, transparent, and equitable way to grow their companies, supported by the startup community as a whole.

I see you, and by seeing you, I bring your value to life in my world.

When we opened Season 0, 90 days ago, and which fittingly ended today, our focus was all about understanding value. Both how value flows within the startup community, especially the value that helps people go faster in the early days, most of which is unpaid and often not recognised as the company grows; and also how we might capture some of this for the benefit of the entire community, supporting our initial mission:

Our core thesis is that if we can capture more of the early unpaid value which flows in startup communities, for the benefit of the community as a whole, we can create a flywheel to allow us to grow more and more amazing founders in the future and thus create a positive sum game where we all win together.

So here we are, 90 days in - what did we achieve exactly, and just where are we going?!

When I originally put out the call to my networks to create something new in supporting startups, something more equitable, and more transparent… something next - I described this as an experiment, and looking back, that’s exactly what it has been, across many dimensions: people, community, understanding this world called web3, and what decentralisation really means!

As Colart lead us through an amazing in-person and virtual retrospective for our community, these were all of the things ringing around my head. My takeaways are shared below as an attempt to capture our learnings in more detail and share where it may take us next. Thanks for reading and being on this journey with us.

Season Recap

We kicked off the season with great intentions and a big vision. As outlined in our last post, we had spent some good time and thinking to articulate a season strategy that allowed us to focus on a number of foundational outcomes this season:

Our season 0 strategy-on-a-page
Our season 0 strategy-on-a-page

Season Outcomes

Looking back, we hoped we would be in a position at season end to:

  • Understand how we can represent and value different types of capital contributions in startup communities;
  • Have worked together to create something of value (key contribution model and event series);
  • Have activated a community of people who have some ownership of the network through participation;
  • Have people know we exist, why we exist, and have a desire to be involved in working towards the next season's goals as members of this community;
  • Have people attend both IRL + URL events and gotten significant value from them;
  • and have grown our community through our season 0 activities.

And as we recap our season, I’m excited that we achieved them all in one way or another, some maybe with slightly less impact than others, but that’s not a bad overall outcome for a rag-tag group of volunteers who weren’t exactly sure where this journey would take them 3 months ago!

So as we recapped our season zero timeline, it’s actually pretty amazing to see both the quantity and quality of the design work our community has managed to produce in that short time!

What did we actually do?! And what could we do better?
What did we actually do?! And what could we do better?

Team = Product

First and foremost for me looking backwards, is that we built a great team of believers around this vision, some who I’ve personally worked with before and know and love, and many who I’ve not. So expecting some storming as we figured out how to work together, what I’m most proud of is the team culture we’ve created.

I’m a big believer that if you build a great team, anything they create by implication will be great also, so I’m particularly impressed how much intent, desire, and safety we’ve created. It’s not only a community where we’ve intentionally prioritised psychological safety, but we’ve managed to communicate respectfully, created an extremely rich environment for learning, and all of us are still here 90 days on! 🙌 🙌 🙌

Voracious Output

The primary goal of season zero (versus season one) was to do some of the initial sensing, design work, and infrastructure build to allow us to hit the ground running when we start working with startups more directly in future.

This means that most of this season has been about collecting our thoughts, design-thinking, production of some key assets, and finding ways to communicate all of that to others.

In that light, here’s a brief summary of the some of the key outputs our group has created this season, many of which will end up becoming foundational documents for our community going forward.

  • The founding document - containing much of our vision, our why, and the potential of how we build a more equitable startup community.
  • The current working strategy - detailing the feel of the positive-sum community we’re creating, what we want to do first, and how we build strategic building blocks on top of that.
  • Community member journey mapping, engagement, onboarding model, and initial platform design to help us understanding how people can be successful here and how we grow the initial community of support.
Our community member journey
Our community member journey
  • Brand exploration, values, and design which ultimately led to a new brand name for the collective which represents the type of community we’re building (positive sum or ) and which is jointly owned by us all now, rather than one person.
Example of some of the inspiration that fed into our community and branding design
Example of some of the inspiration that fed into our community and branding design
A key output this season is how we model & capture value flows in startup communities
A key output this season is how we model & capture value flows in startup communities
  • A simple online web presence to create some mystery and intrigue around what we’re doing, and to provide an online drop for exclusive events and rewards.
  • An active async voice and text communications platform (discord) to allow our community to come together, ask for help, and get work done (mostly being used by our working groups for now until we open our doors officially!)
Discord: our async team comms platform and heart of our current community
Discord: our async team comms platform and heart of our current community
  • We built a custom season bot to sit in discord to nag us and keep us focussed on how long we have left in the season!
Our evil season bot keeps us on our toes and reminds us how little time we really have!
Our evil season bot keeps us on our toes and reminds us how little time we really have!
  • Designed and started building a technology platform to become the focal point of a number of key community 'services' to help startups find, access, and log the help they need and the value being exchanged - development currently in progress with two of the key services being built out already (member directory and value exchange).
Our member directory allowing people to search and find the help they need from other community members and experts
Our member directory allowing people to search and find the help they need from other community members and experts
  • And finally, we took the opportunity to get into the real world and engage with startups to confirm some of our assumptions around the support they need as part of the recent Perfect Loudness Web3/Music-tech festival in Auckland.
Dan & Jonah talking about building positive sum startup communities at Perfect Loudness
Dan & Jonah talking about building positive sum startup communities at Perfect Loudness

Looking back, this is a huge amount of foundational work completed, much of which will be invaluable once the community is operating at scale - amazing for a small group of volunteers also holding down full-time jobs! 💥 💥 💥

Managing Our Energy And Capacity

And that brings us onto one of the downsides of our approach.

Whilst we have produced a lot already, we intentionally chose a small group of enablers, to allow us to be focussed in what we’re building, and allow us to ease into new decentralised working models that not many of us had worked under before.

And that trade off of a smaller group really started to hit home mid-season as the energy took obvious dips, as shown by our energy ‘seismograph’ which Colart led us through as part of our retro.

Our messy retro 'seismograph' showing our ups and downs and collapse of energy/capacity part way through
Our messy retro 'seismograph' showing our ups and downs and collapse of energy/capacity part way through

In some ways this reminds me of the infamous graph from YC that most founders have a love/hate relationship with:

YC's innovation/technology hype curve - image credit:
YC's innovation/technology hype curve - image credit:

Almost all of our members hit a wall at similar points throughout the season, as the initial buzz of a big vision and roadmap turned into hard work carving out time to work on delivering that vision.

One of the challenges of building an online community like this is that we tend to get an energy boost when we have strong (real) deadlines, and when we can physically get together and feel well-supported.

You can see exactly this when we had our first energy dip mid way through when we introduced discord and comms suddenly sky-rocketed, but conversely added a huge amount of noise as people couldn’t keep up, but also as they came out of that and energy started to accelerate once we worked towards our first pre-launch real-life event, and our team retreat where we got together in-person.

One of the big lessons here is that community is about humans and belonging and not just creating new things. We all need the energy buzz we get from being physically around others as we all know now after being holed up during the various pandemic lockdowns!

Key takeaways

  • Managing our energy as we move past the excitement phase to the delivery phase
  • Seeing and being involved in things that created tangible outputs did wonders for our energy
  • How do we individually and collectively manage overwhelm as we move from in-person comms to async comms and vice versa for events like this
  • Our capacity issues really drove a lot of the end of season energy dips and guilt for lack of delivery and management - how can we get better at asking for help sooner
  • Our lack of structure as we started operating drove overwhelm as people tried to be across too much and ended up spreading themselves too thin

Structuring Chaos

As our mode flipped from thinking to doing, we definitely suffered under the weight of so many aligned, but disparate working groups and activities to allow us to meet the season goals and outcomes.

Whilst we had some lightweight systems in place like the odd Trello board and a centralised document repository, the biggest tension we suffered was not having clear processes, reporting, or visibility of where things were at and who’s doing what.

‘Scrappiness’ (as we tell startups to be in their early days) certainly ruled our roost!

This was especially noticeable as new members came back into contribute after being away for a little while. Those in the working groups were up to speed and in motion, but it was hard to re-onboard existing members to provide a picture of where work was at across the community as a whole.

We still maintained regular community catch up calls, but because we were all busy and tactical meetings weren’t happening in working groups, these community calls, originally intended for anyone to join and get a quick update on where the community is at, mostly become operational.

A good lesson that working on enough structure to create this visibility and accountability will allow us to be much more effective. And we’re only 10 people at this stage - I can’t imagine how early communities with 100s of working group members manage this early on!

Self Management and Decentralisation

Closely related to this is shifting our mindsets from the traditional hierarchical model to a more decentralised model of operation, which we know we need to operate a DAO at scale and to take the pressure off a couple of individuals.

Since we were all relatively new to this and we assumed some progressive decentralisation, we didn’t lead out strong on this setup, more felt our way in a way we thought was right. But this self-management structure also ended up taking a back seat as we focussed on getting stuff done rather than how we got stuff done.

Whilst this allowed us to produce the voracious output above, it also got us a bit stuck because we never really set the rules for how to self-manage our work in communities like this and how to bring others into the loop on individual progress.

We were clear at the outset that we wanted to adopt new models of self-management and decentralisation, both to reduce any centralisation risk that one person is in charge, but also to allow new ideas to emerge and allow anyone to be empowered to add value to the DAO in whatever way they wanted as long as it aligns with our overall purpose.

Most decentralised communities adopt a Holacratic-ish approach whereby the community is structured into circles, with each circle being empowered with their own purpose, allowing them to define whatever roles or work needed to allow them to deliver on that purpose and which broadly aligned with the overall seasonal goals the DAO is working towards.

Holacratic communities organise themselves into circles and distribute authority - Image credit -
Holacratic communities organise themselves into circles and distribute authority - Image credit -

As we discovered, this self-organisation is hard because it requires a strong facilitator and buy-in from the team (including some extreme motivation and capacity to push a roadmap of work forward). Given most of us hadn’t worked this way before and we didn’t outline this structure clearly enough, many of us fell back to old ways of working, clamming up when we got busy rather than deputising others or asking for help, letting things build up rather than raising tensions, and ultimately not taking the initiative to lead when there were gaps of information, instead waiting for others to do that.

Whilst some of this can be solved with better structure, and models like Holacracy are designed specifically to deal with some of these things, I feel this is such a different way of working that most people don’t yet have a frame of reference for, that it will be a constant tension and a key area of focus and growth for us all going forward.


Closely related to this structure and self-management is a reflection on commitment. I don’t mean commitment in the traditional sense - people are obviously aligned with the mission, on the bus, and turning up each week.

But we assumed everyone knew what needed to be done so didn’t go too deep on setting out our expectations so that community members could hold each other accountable. I.e. the DAO itself didn’t tell members ‘here’s what I need from you in this specific role, and how much commitment it needs each week’. Combined with also not being clear what capacity people had, we ended up with a classic volunteer organisation problem of assuming people had areas covered when they didn’t have capacity or the expectations on delivery weren’t obvious.

Roles and responsibilities in decentralised communities aren’t like full-time jobs (although they can be) they’re usually much smaller and finer-grained - e.g. weekly community call facilitator versus community manager for the entire DAO for example.

So rather than people not being committed, we suffered more with the DAO not being clear that it needs a specific role, for example, 1-hour a week for someone to organise the community catch up call and setup the event on the calendar, making sure people turn up and making sure that role explicitly belonged to someone so others could hold each them accountable.

The upshot of not doing this this well this season is that these type of jobs either fell back to one person, or fell through the gaps as people got busy on other work and then it became hard for others to pick back up or we lost momentum, and maybe this possibly contributed to the mid-season energy dips too.

Vic's logical brain came to the rescue of where we need to put more structure in place
Vic's logical brain came to the rescue of where we need to put more structure in place

Our ultimate lesson here is that decentralisation is hard! Structure can help, but we also need to flip our mindsets and operating rhythms to make it work, but that’s also a balance when we don’t have capacity!

Key takeaways

  • Ask for help more often and for specific things
  • Be braver with feedback => use check-ins more
  • Find better ways to communicate with each other (channels of communication)
  • Understand who is here, what their capacity is, and how we hold each other accountable
  • Work async effectively
  • Identify all current roles, responsibilities, and accountabilities
  • Use limited time to be more effective in specific areas rather than across the whole
  • Better allow people to explore how they want to be involved and new skills they want to learn
  • Better visibility of progress across working groups and across the DAO as a whole
  • Apply more holacratic principles in the way we work to help create autonomy, self-management, and ownership => mentor and guide the team in new ways of working

Season 1 Planning

So plenty of micro and macro- lessons for us out of that season and much to work on to help us smooth our operations into next season.

So, what about next season?

Whilst we never had time or intention on this mini-retreat to get too much into our next season’s strategy, we did spend a chunk of time reflecting forward on what our next steps might be.

One of my personal observations from this season is that whilst I was happy operating in the season “meta” and could see the way forward, some others really struggled with this meta-view of what we’re doing, for who, and what our value proposition to those people was.

So whilst we’ve done a lot of design and infrastructure thinking, it’s worth reminding ourselves what we’re trying to do here and for who!

Whilst our goal is to build a community - we’re not just trying to bring people together ‘willy-nilly’, we’re actively bringing them together to do some very specific things (share networks, help mentor each other, create educational resources for each other, and to create some cool events where we can hang out together and belong).

Whilst we are broadly calling this ‘community’, it’s hard to articulate exactly what it is because it doesn’t yet have a “product” or a “programme”- focus, so most DAOs fall back to leading out with community, but they’re often so much more than that.

Our ultimate goal as expressed in the founding document still articulates it best:

A decentralised peer-to-peer community of startups, mentors, and startup community “enablers” who help each other create unfair advantage through our networks, knowledge, and know-how, and who all hold a long-term vision to build and operate shared assets that add collective value to the community as a whole

But currently without a programme focus, it is more like an ‘open fellowship’, enabled with some technology, and people. I guess we could call what we’re building ultimately a community-led startup accelerator in some ways, but that doesn’t quite do it justice either - it’s so much more than this as it emerges and evolves as whoever shows up decides how to grow and fulfil our overall mission.

This is how we expressed it on our website recently:

Positive sum is peer-to-peer community of startups, innovators, and change makers who help people create the future 10x faster than they can alone.

We're an open and transparent community, operating as a DAO on the blockchain, meaning that the more people share their networks, their knowledge, and their know-how to help others succeed, the more the community as a whole becomes more successful and we all win together.

We're not only here to offer startup support, we're actively building a unique IRL + URL community with events that blend startup, pop, and crypto- cultures to create something altogether different that people want to be part of.

Our ultimate goal is help more people create positive impact in the world through game changing innovation, the power of entrepreneurship, and by helping each other create positive sum impact where we can all level up together.

Focus on Startups

Looking ahead then, what becomes clear is that it’s now time for us to come down from the meta and start proving out some of the models and value creation we’ve talked about during season zero.

Most of our season one intentions therefore, rightly focussed on growing the community, proving that startups can and will get impact from this open network/shared resources, and validating that capturing these value flows in the startup community creates more momentum.

How we activate that flywheel and exactly who we bring into the community to help add the right amount of capacity and support to allow us to create value will be critical as we feed into next season’s planning.

Over season one intentions and themes
Over season one intentions and themes

And from a user-outcomes perspective:

How will we know we're successful?
How will we know we're successful?

Which leads us to a number of intentions and questions to feed into our next season’s strategy:

  • Validation - do the models we designed work? Will people engage?  What’s our proposition to startups? To mentors? To other contributors?
  • Impact creation - can we create value for these people, as we intended, using both the people we have here and tools we are building? Will more crazy, cool ideas see the light of day because we existed and organised together in this way?  Can we generate data or case studies that show our impact, and specifically how people have created value for one another? Does the contribution → reputation → satisfaction flywheel work? Does visibility of contribution create more momentum?
  • Work on our system - so people know what work is going on, how they can contribute, and what outcomes we’re working towards.
  • Grow the community - figure out who, how, and what we need to bring people here and keep them engaged.  Figure out what we need to do to move people from explorers through to shapers and getting more involved.  Implication of working more on community management in the next season over pure-community-design work.

Whilst there’s plenty of key lessons for us to takeaway and feed into our thinking for next season, it’s important not to beat ourselves up too much on what we can improve, as we can always work better! What’s most important is what we did - and that’s created an awesome starting point with great ingredients to go forward - which now needs to switch gears into testing whether or not any of this represents value in the face of real feedback!

And with that, that’s officially a wrap on season 0! 🎬💥❤️‍🔥

Phew! An intense, but satisfying day spent with some awesome like-minds who all care about growing new entrepreneurs and giving back so much to figure out a new, more equitable, open, and transparent way to do it where we can all win in a positive sum way together.

Exhausting, but huge fun, meaningful, and great to spend so much face-time with an awesome emerging crew of long-term collaborators I’m sure.

Our season 0 retreat participants (from left): Dave, Pauli, Helen, Justin (video), Vic, Dan (me), Colart, (& Tracy who was offline during this pic).
Our season 0 retreat participants (from left): Dave, Pauli, Helen, Justin (video), Vic, Dan (me), Colart, (& Tracy who was offline during this pic).

To each of these amazing people and those who also contributed to making season 0 awesome - I see you, and by seeing you, I bring your value to life in my world.

Get Involved?

Any of this feel like a community you want to be part of as either a startup or a mentor or contributor? Get in touch with either myself or one of us if you know us - I’d love to talk about how we can build this together as we head towards season one!

None of this would be possible without these awesome season 0 core contributors who co-created the content in this article of which I had the honour of writing up.

Massive shout out to – Jonah Merchant, Tracy Moyes, Dave Meaney, Jeremy Kennealy, Helen Flitcroft, Vic Jack, Justin Douché, Pauli Sosa, and Colart Miles.

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