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What Failing Taught Me About Positioning a Social Venture For Long Term Sustainability

I know what it’s like to fail and walk in one’s personal hall of shame. In 2009 my first nonprofit venture, the Global Giving Circle, failed after its first event, which ironically was an incredible success.

I know what it’s like to fail and walk in one’s personal hall of shame. In 2009 my first nonprofit venture, the Global Giving Circle, failed after its first event, which ironically was an incredible success. The failure could have easily been avoided had I consulted a lawyer before launching. But because I was trying to cut corners I selected a DIY strategy which resulted in a trademark infringement with I hadn’t done a thorough search before selecting my organization’s name. The name was similar enough to cause “confusion in the market place” and that was that. All it takes is one fatal mistake when building a new venture and it’s “game over.” Better to learn this now. I learned it from the school of hard knocks.

Looking back I realize that had my enthusiasm been tempered with a respect for all things new and unknown, and had I been willing to spend the money needed to hire someone to navigate the waters surrounding terra incognita, I might still be in business today. But I had unknowingly employed the fateful strategy of “figure it out as you go” – not a winning strategy for most things related to business.

Resilience is a necessary ingredient for anyone committed to the work of a changemaker. Humility is another. Creativity a third.

As a result of my failure, I cooked up something all together new which I named the Social Innovators Collective. It originally launched as a membership organization designed to connect dynamic, emerging founders, leaders and individuals who worked in the social enterprise and nonprofit sectors both nationally and internationally. The mission was to share knowledge and support each other’s work so that others could avoid the difficult lessons I had learned. But creating a strong business network was not enough to produce social entrepreneurs with staying power. Two years later less than half the members were still in business and no more than ten were making their full living, often meager, from their social venture. Consequently, we pivoted to focus on education because in 2011 it was clear that this was missing in the social impact space.

Many changemakers are focused on creating and developing projects and programs, not on how to run a small business.

With social entrepreneurs being celebrated in leading business sites like’s 30-under-30 list or Business Week America's Most Promising winners, we don’t often hear about the failures. But, few social entrepreneurs are equipped to design, build and scale sustainable businesses. Startup funding aside, this is partly due to the fact that there is no focus on training and there are only a few high quality educational resources online or offline targeted at changemakers.

In response to the high failure rate that members of the Social Innovators Collective were experiencing, I began to produce workshops on financial sustainability at General Assembly, New York’s premiere center for entrepreneurial education. After 18 months, and realizing that more long format programming was needed, I co-created an 8-week workshop called Social Good Startup with Todd Schechter, the Co-Director of Ignite Good. The course blends theory taught at leading graduate schools with the hands on practical advice and experience a changemaker will need in order to move their venture forward. In eight weeks, we teach startup changemakers how to articulate their mission and vision, create a competitive analysis and needs assessment, and define what success looks like, with a focus on impact. Then we train participants to design and deliver compelling pitches for future funders.

In-person classes and workshops are highly effective, but there are only so many people you can inspire in a classroom.

I understood that in order to create a viable business, and one committed to significant impact, we would have to come up with products and services that would be available online. So, while Todd and I were developing curriculum for the workshop, I was working with my colleague Marc O’Brien, Founder of Confidence, and a team of leading professionals in the social impact space to author content and design covers for a guide series called the Social Good Guides. Many of the authors taught classes for the workshops I produced at General Assembly and so the material had already been successfully tested. The 20 guides include topics such as legal structures, branding and identity, marketing, accounting, operations, strategy, evaluation and impact assessment and more. Each guide answers two essential questions: what does a startup changemaker need to know about topic x and when in the arc of one’s first year should they focus on this subject.

Sixteen of the twenty guides have been written and beautiful covers designed, we have a work-in-progress site up and the first guide Idea to Launch authored by Andrew Greenblatt, Founder and President of Vendorboon and Adjunct Associate Professor at New York University, is available as a freedownload on our site. The “finishing funds” we are seeking will ensure that we can fulfill on our mission – to spread this information far and wide.

Though the guides are targeted at people soon to launch their ventures, they will also be very useful for changemakers whose ventures are up and running, but are experiencing roadblocks because they are lacking important knowledge and skills.

Part of what makes the Social Good Guides so special and unique is that we’ve found authors who are not only experts in their fields, but professionals who have an intimate understanding of the social impact space. Curated content and resources from a community of highly esteemed professionals is one of the benefits of this guide series.

There’s nothing wrong with clever and innovative, but what we are committed to with the Social Good Guides is to impart practical, “how to” knowledge. We hope that with the guides we’ll save intrepid do-gooders from the inevitable doom that comes from ignorance and wishful thinking.


For those of you interested in offering your thoughts and feedback on what you think is needed or wish to join the team of the 55 people who have been working with us since May of 2012, here are some ways you can get involved.

As a member of the GOOD community, you can fill out this survey which will take 3 minutes and let us know what you want to learn and which of the guides you’d like to see released first.

For those of you who are designers, please fill out this form where you can input your name, website and email and someone on our team will get back to you. We are looking for some support in this area.

You can also sign up for our e-newsletter and be one of the first to know when we are ready to launch here:

Shana Dressler is the Founder of the Social Innovators Collective

Images from top to bottom courtesy of Jacqueline Gu, Mollie Ruskin, and Liz Cook

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