Are you a Serial Charity Starter?

I'm no longer convinced this is a good way to frame my line of enquiry. Do still share if you have a comment.

I want to find out if software can help voluntary startups coordinate well in their earliest stages.

You may think the answers are so obvious that discussion is merely academic. When I design, I like to articulate the rationale for my projects. So while I already have strong opinions, I am temporarily setting them aside to take a considered approach.

Before I make any software, I want to ask these questions:

What are the common lessons of starting a voluntary organisation? Can serial charity starters develop similar levels of knowledge as entrepreneurs? Where can technology help?

By entrepeneurship, I'm referring to the rich body of experience I have witnessed within the tech startup world. Here are some examples:

• Healthy, constructive debate about incentives, management, contracts, and culture for startups
• Theories on what is a business model, and how to find the right one for your company (c.f. Business Model Generation Handbook)
• Theories on how to develop new products and services, as a new or existing organisation (c.f. the customer development model, also Christiansen's work)
• Well articulated checkpoints in the growth history of an organisation, including goals and exits
• Links between personality types, organisational models, and funding structures (c.f. Steve Blank on "Why Accountants Don't Run Startups")
• Theories of constraints and project management
• Rich, complex debate on coordinating startup teams, with a large range of techniques and software to support these approaches (kanban, scrum, agile, lean, etc)
• Well established programmes of mentorship and early stage funding for new startups
• An environment in which even technical discussions can take place in respect to the nature of your organisation (c.f. Paul Butcher in Debug It! and Fred Brooks in The Design of Design)

Taken together, these discussions focus on how to do things in the earliest stages of the startup, how to figure out what your startup does, and how to grow from there.

The shared language and debates around these topics have created the category of entrepreneur as a transferrable skill. Since I have participated in several technology startups, I know what to expect if you put me in a team of 3-10 people and ask me to help create something new. Many of us who have been part of self-aware startups develop views and practices in all of the above areas, and in a new startup, we are able to argue, decide, and learn what is right for the new company. As the startup grows enough to become a more established company, or once it reaches an "exit," the serial entrepreneurs among us stay as long as we're helpful and then look for the next startup.

Perhaps this category of serial starter shouldn't exist for voluntary organisations. Voluntary organisations are much more diverse than startups. In addition, common wisdom suggests that the best voluntary org starters are first-time campaigners. It may well be that voluntary organisations lack the certainties of startup companies which make serial entrepreneurs possible in business.

Maybe voluntary organisations are too diverse to merit shared practices and technologies in their early stages. In business, the profit motive imposes shared structures on all startups. This pressure is most noticeable with investor practices, legal requirements, and project management. Voluntary organisations have much more diverse goals; maybe each group needs to develop their own approach to organising themselves.

In voluntary organisations, the common narrative seems to centre around inspirational individuals who either become figureheads or get ejected from their organisations once they reach a certain size. Paul Farmer started health clinics as a young man by stealing equipment from his university and by building an organisation around relationships and ideology. He remains with Partners in Health to this day and is now a senior figure in public health. In contrast, the founders of the WinterComfort day shelter were imprisoned after the first few years, and their charity survived by transforming into a slightly more conventional organisation (c.f. "Stuart, a Life Backwards" starring Benedict Cumberbatch). Both are cases of wonderful voluntary organisations started by inexperienced leaders on their first project. In both cases, more experienced people would have certainly avoided the radical approach they took.

A third problem is that developing a voluntary organisation is much messier than starting a company. Commitment, motivation, and rewards work very differently, and contracts are rare. Goals and outcomes vary much more widely between organisations. Within a charity, constraints (scope, time, budgets, people) are not as well defined and can dramatically change much more unexpectedly than in a business.

If I am to design software to help early stage voluntary organisations, I want answers to each of these objections. I also need credible design ideas. Towards those ends, I plan to:

• Interview people who are experienced in starting voluntary organisations
• Learn what people are already saying about startup voluntary organisations
• Identify specific challenges which software might address
• Review software that already exists

Are you a serial charity starter? Do you have ideas for technology? Or do you think this is complete rubbish? Please email me your ideas, articles, links, and software, and I will try to post them here.