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For a long time, I felt funny about calling myself an ‘entrepreneur’. Entrepreneurs were people who went for broke, putting it all on the line. That’s not me.

I’m not much of a risk taker. I always have a cushion in my savings account. I line up plans B through F, in case plan A doesn’t pan out. I’m not an early adopter of new tech. I wait to see how my friends like the new app or gadget first.

Just recently, I’ve been getting paid in cryptocurrency and started handling Bitcoin for the first time (see above about not being an early adopter). I was presented with immediate questions about risk. Should I sell the Bitcoin as soon as I got it, or save it, betting it would go up in value? Normally this kind of dilemma would make me feel like curling up into a ball.

But this time, it didn’t.  More importantly, the experience has helped me realise something about my relationship with risk and about how I have been able to happily work on volatile startups for years. The key is: I’m not in it alone.

I work as part of a small cooperative, where we pool all our income collectively. That Bitcoin wasn’t mine, it was ours. I was able to share my fears and hear the perspectives of the other co-op members. Then we made a decision about how much risk to take together. For me, that made all the difference.

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In a system where relationships are primary, there can be no hiding. Listening, compassion, a well-tuned sense of how people are feeling, and an ability to ask for what you need are essential to self-organisation. Our existence depends on relationships. When we admit we don’t know something, or that someone’s else’s idea is better, or that we’re scared and in pain, or that we feel alone, we start to create the conditions where trust can grow. — “Start with I”, Kate Beecroft, Better Work Together, p. 234

My journey with startups began in 2011, when I moved to New Zealand and joined Enspiral, a collective of social entrepreneurs. Over the years, we tried many different experiments in how to run companies and work together for positive social impact.

Across all these projects, the common factor for success was working as a community. We pooled resources and took responsibility for one another. We made decisions as a collective and took collective ownership of outcomes. When someone got their laptop stolen, we bought  them a new one, together. When one startup ran out of runway, another company in the network would hire those people. When any one of our radical experiments didn’t pan out, we caught each other before hitting the ground.

We challenged and encouraged each other to build wellbeing, resilience, and connectedness, and stuck with each other through the ups and downs of personal and professional growth. While we often lacked money (traditional capital), we were rich in relationships (social capital), and together we had enough to keep going through the hard times. We spread risk — and reward — among us all.

It is hard to describe the transformative experience where you feel your individual potential radically amplified by a supportive community. Something happens. A conversation, an interaction or a new opportunity emerges. Suddenly, you feel different about yourself and what you can achieve in the world. The growth feels tangible, like you’ve grown an extra limb or unlocked a new superpower. — “All Things Being Equal”, Anthony Cabraal, Better Work Together, p. 92

I often hear about entrepreneurs feeling isolated. By definition, bringing a new idea or product into the world means believing very strongly in something other people don’t see. You have to keep going despite setbacks, despite stress, and despite watching your friends with stable jobs buy houses and take vacations. It takes real fortitude.

An early stage startup founder is confronted daily by existential decisions. If you’re alone, it’s all on you. Every problem that arises is your problem to solve. Entrepreneurs take huge risks, striking out with no map into uncharted territory, often putting all their personal financial and psychological resources on the line.

No way in hell could I do that on my own. Absolutely no chance.

Sir Edmund Hilary didn’t climb Mt. Everest on his own—and he didn’t do it in one go. The team comes together, toils together, goes up, comes back down, acclimatises, waits out storms, humbles itself in deference to what it can only do together. This isn’t the work of the individual, but the individual must be prepared for the work of the team. Together, through the challenge, we gain strength. Together we support each other to learn, to dig in and to expand the realm of what’s possible. Together teams scale mountains. What are the mountains we can only climb together?  — “Doing What We Can Only Do Together”, Susan Basterfield, Better Work Together, p. 131

I think a lot about diversity and who gets to be a founder or a leader. To me, it’s about realising human potential. If brilliant minds or unique perspectives are shut out, we all lose. Now I see how that applies to myself when it comes to risk aversion: because I had the opportunity to join hands and jump with trusted collaborators, I was able to take risks and become an entrepreneur.

How many potential entrepreneurs are not taking risks because they think they have to do it alone? How much more incredible human capacity could we unleash by taking risks together, in community?

To really extend ourselves we need to feel genuinely safe to fail…. It’s OK to fail financially. You’ll survive and more opportunities will come up. It’s OK to fail emotionally. You’ll be supported to pick up the pieces and work out what to do next. It’s OK to fail personally. You’ll learn, you’ll grow, and you won’t be cast into the wilderness and rejected. Regardless of what you are trying to achieve, a community can amplify your dreams, challenge you to grow, and transform your sense of what is possible. You can try more. You can take more risks. You can reach higher. — “All Things Being Equal”, Anthony Cabraal, Better Work Together, p. 94

Another thing I never thought I’d be able to do was write a book. The enormity of hundreds of blank pages to fill, of justifying my singular voice as one that should be heard, was too much to handle by myself. Luckily, I didn’t have to do it alone.

Twelve co-authors from Enspiral have written our first book, “Better Work Together.” It’s not a book of theory; it’s a field guide by and for practitioners. It’s a collection of essays, tools, and stories from the front lines of a more collaborative future of work. We share key learnings from our experiences taking risks for our passions, values, and dreams of building a better world.

Sometimes we triumphed and quite often we stumbled — but it was OK, because we did it together.

Quoted excerpts in this article are from the new book Better Work Together, co-authored by Alanna and 11 collaborators from Enspiral. Paperbacks and digital books are available now at

Alanna Irving


Alanna Irving

Alanna has co-founded multiple startups, including Loomio, Cobudget, Enspiral, and Dark Crystal, and currently