Startup #2: Accountability and support for solo founders

Working solo can be challenging.

For one thing, there's solo productivity and time management:

When working on a project in-between existing commitments, it can be easy for things to drift and not get done as fast (or as efficiently) as they could otherwise. Why? Because they are battling for priority against other tasks, and there are no hard deadlines to provide adequate time pressure.

It's extremely common for solo work to be unfocused and unstructured with no defined start, stop, or any tangible goals per block of work. Whilst efficient teams commonly estimate the time required to complete tasks, calculate the quantity that can be achieved within a given timeframe, and repeatedly check-in on progress – solo workers do none of these things, nor do they have anyone to do these with.

The other thing is lack of support:

Working solo can be lonely. You don't have anyone to bounce ideas off or to share successes with. When a project isn't going well, you may not have anyone to talk through issues with, which can be isolating – but also you can't benefit from others' experience.

Merely speaking thoughts out loud or discussing with another person can help structure and clarify your thinking on a topic. Your own head is an echo chamber – talking to others is how you re-ground to reality.

Founder/entrepreneur mental health is an important and growing area of awareness.  They encounter a lot of stress, face challenges and a lot of pressure - but rarely have a support network in place to share and overcome their problems (or even just talk them through).

Problem validation

In the wild there are already a number of analogues to solo workers joining together to work side-by-side and get accountability:

Study groups - students gather to study together, socially enforcing attendance, providing each other support and checking-in on topics together.

Accountability partners/groups - I've seen startup friends that do weekly check-ins with an accountability partner, but I myself have also been a part of accountability groups (e.g. at Escape the City) and seen how much more effective it is to set goals with a small group of people that check back in with you. This provides both support in issues that you are encountering, and holds you socially accountable to get done what you said you would.

Gym buddy - Solo gym attendance can be affected by your mood, motivation/discipline, energy levels etc. – but half the battle for success in a gym environment just comes down to getting yourself there. After having trained, you always feel better for it. Gym buddies make the training process more fun, but also socially enforce attendance and provide structure.

Personal trainer - Customers of personal trainers effectively outsource peer pressure and structure to a 3rd party that's financially incentivised to be bought into their fitness outcomes.

There is also a rising trend of public accountability groups for solo workers (Work In Progress, Product Hunt Makers, Makerlog and many more) – however, these are all large scale impersonal groups where members have low familiarity with each other and even lower familiarity with each other's work and goals. Because of the weak ties in these groups, users also won't be able to look for any real emotional or other support from other members.

Proposed solution

Work side-by-side in curated mini-teams of solo workers 👨‍👩‍👧‍👦

• Support each other with problems 🤝
• Share learnings and expertise 🧠
• Push each other forward and share successes 🥂

Project:Work (working title for the project) aims to overcome the above issues by creating tight social groups with mixed skills and experience that can support one another, as well as hold each other accountable to complete the actions they've committed to.

A few people deeply bought into your project can hold you far more accountable than a hundred strangers on the internet.

Social deadlines. Deadlines are meaningless without a consequence - Project:Work provides social accountability by match-making solo workers into small teams where everyone gets to know each other and understands each other's projects – they are bought into each other's success.

Users are asked to commit to their week's personal tasks publicly within the team, and the team can see as those tasks do (or don't) get completed. They hold each other accountable to finish what they said they would 👀

When a user encounters problems, they can call upon the diverse expertise of the rest of the team (which is where team curation is important).

Build

I decided to use no-code tools to ship the first prototype, which meant extremely fast turnaround from concept to finished MVP... I started building on a Tuesday and by mid-Saturday had completed:

- Webflow landing page 🛬

- Coda task/time management and team sharing app ✅⏰

- Slack bot powered by Zapier 💬

How did the MVP work?

New users are matched into teams (manually), introduced to each other and can begin adding tasks to their to-do lists.

The Slack bot acts as a kind of light-touch scrum master:

• It prompts at start of week for overall week goals & obstacles
• At mid-week it checks in on progress
• At end of week, it asks users to do a review and check in of their wellness (also general task management)

All this is shared for group transparency & mutual support.

Throughout each week, all team progress is visible in the 'Progress' dashboard for mild competition/motivation, as well as individual stats on tasks done etc.

From wellness & mental health perspective, everything is designed to bring the team together & foster openness, creating a supportive environment. Users rate their happiness which is tracked over time and also vote for 'most helpful' team member to incentivise intra-team support.

Launch

The Project:Work prototype won a runner-up award 🥈 in the Product Hunt Maker's Festival. At the same time, I collected sign-ups via the landing page, bringing a small selection into a trial at Dojo Bali the following week.

Trial

In general, the trial showed that users saw a lot of value in the value proposition, but the trial wasn't a total success with relatively low engagement and non-committed members – for a number of reasons:

• Users had low familiarity due to lack of bonding and connection in onboarding. Simply putting users in smaller groups doesn't guarantee deeper connection – they need more of an intro and a chance to get to know one another. Obvious, but one I missed in my eagerness to ship.
• The prototype was a great proof of concept, but the 'no-code' solution was just a bit too clunky, required users to bounce between different apps, which saw engagement drop-off with low-commitment users.
• Duplication of to-do list. Interviewing users revealed that the prototype required that they record their to-do list twice, which means that it actually adds work to their plate (rather than making them more productive with existing workload). This creates too much friction at this stage.
• The Coda tool lets any user make app-breaking changes, so isn't really suitable to building apps that need to restrict user vs. administrator permissions... Any user can inadvertently delete half of the app – not ideal.

Evaluation

I will iterate on this concept – definitely very real value in this space and substantial interest, but this solution didn't truly fulfil the need.

Next iteration will:

• Have more focus on team-bonding. Members need to get to know each other for it to not merely be a list of stranger's names in a chat app. Perhaps this will happen by video or face-to-face, but in any case more familiarity is needed for users to buy into and care about each other's projects.
• Require members to commit to stick to the process for a month – perhaps with a clear end point, better gamification etc, and more selective access in the first instance.
• Avoid duplicating existing task tracking, and instead exist alongside or pull in data from existing task tracking solutions.