Social Enterprise Law in Beta – A Conversation With Kyle Westaway

by / ⠀Entrepreneur Interviews / December 20, 2012

Social enterprise: an organization that uses the forces of the market to do good in a socially or environmentally conscious context. Although it can be structured as a for-profit business or non-profit organization, it is distinct in that its social aims are primary, and profits are secondary. Different from companies who may raise money for charity in service of or as an adjunct to their for-profit mission, the chief focus of a social enterprise is to change the world for the common good.

Attorney Kyle Westaway stumbled into this field several years back when he was working with some friends on a project to help women in Southeast Asia coming out of the sex trade to transition into a healthier and more stable life. Together they created a fashion brand called Biographe that employed these women in a way that contributed more positively to their lives and their communities. He felt so passionate about this work, that he decided to devote himself full-time to the practice of law in service of other such projects through his firm, Westaway Law.

Social enterprise and social enterprise law are still relatively new fields, but have been gaining increasing popularity over the last decade. Westaway, who had bravely (or naively, he muses) launched his own firm in 2008, decided to refocus his practice entirely towards the field of social enterprise law in 2009. The decision to align his career with his passion was a risky one. He had previously been working with a variety of clients, including artists, activists, entrepreneurs and indy musicians, when he realized he needed to concentrate in this one particular area.

In our recent conversation, I asked Kyle how he made the transition into this relatively unknown field, and what he did to establish his practice. Making the choice to focus on social enterprise was only the first step. Next, he had to establish a track record by building a client base. Knowing that the relationship between lawyer and client is one built primarily on trust, he set about building connections with people by impressing them with both his passion as well as his knowledge of and ideas about social enterprise law.

Although he claims he tried everything to market his practice besides a billboard, a subway sign or the yellow pages, Kyle ultimately developed traction with a combination of blogging, social media and good old fashioned socializing. I suppose nothing beats face-to-face meeting, where you can really get to know someone through direct conversation. However, the sharing of meaningful content through his blog has also been very impactful.  In 2010, Westaway founded, the first blog devoted specifically to the field of social enterprise law. His writings there, as well as more mainstream pieces he’s penned for the Wall Street Journal, Harvard Business Review and GOOD Magazine, have all gone a long way to establish his authority in this burgeoning area.

The third successful piece of his outreach was accomplished primarily through his communications on Twitter. This echoes experiences I’ve shared in other industries as well. As he explained it, he was fortunate to be involved in this particular conversation at the right time, when it was just beginning, particularly during the early days of Twitter, when people were very open to talking to people with whom they might not normally speak. It was an archetypal Twitter experience. Cutting across offline barriers to access individuals across a wide spectrum, Westaway was able to position himself as an expert in his field, developing many genuine relationships along the way.

Perhaps the most interesting part of our conversation for me was to hear of Kyle’s application of basic start-up principles from The Lean Startup to the practice of law. He has adopted a stripped down approach that does away with much of the bloat of conventional law firms. Gone is the expensive Park Avenue office with costly art collection, the full-time roster of partners and support staff, and most notably, the practice of billable hours. He charges his clients on a per project basis, and, working with a network of attorneys, he brings in a specific team for each project. This together with his adoption of a paperless office has enabled him to cut costs significantly for himself as well as his clients, with the added bonus of a completely mobile practice that was able to seamlessly relocate to another city during the recent hurricane.

As he sees it, his legal practice is a model for what he envisions as the business of the future. He has observed the increasing reliance on both automation (robots, artificial intelligence) and outsourced labor for the majority of the work needed to run the modern company. He believes that the remaining required labor will be highly skilled, and only those who are able to work in a flexible, rapidly evolving environment will be able to iterate fast enough to keep up with the trend of maintaining a constant state of beta.

Although this is good news, indeed for entrepreneurs and individuals who have already made the shift towards a more independent and creative working style, it is a sobering reality for people who have crafted their lives and careers around the older way of doing things. It has become fairly obvious that our current economic structure is undergoing some kind of system wide realignment, and people are now in a position of having to rethink many of their basic assumptions about how things work. However, given the progressive terrain of social enterprise organizations, innovation is the name of the game. As we see the growth of a new kind of approach to business, charity and global responsibility, who knows what kind of possibilities will come about for fresh business and employment opportunities.

Kyle Westaway is riding the cusp of this wave of change, embodying the ethos of living a career in beta as he continues to explore new and innovative ground. To others who would pursue a similar path, he suggests starting with self reflection, “… something our generation is not so good at.” He adds, “Take time to listen, understand what you’re good at, what makes you come alive, build something that comes out of those values and see if it works.”

Secondly, he recommends maintaining a constant state of iteration about your choices – “Evaluate, see if it’s worth continuing or if you should step away from it – either leave it or look in a new direction to build skills.” Thirdly, he advises embracing humility, as being OK with failure allows one to take more risks. Unfortunately, he says, “Lawyers are not usually known for those three things, so that attitude needs to change if we want to be innovative and on the cutting edge.”

Listen to the full interview here:


Deborah Oster Pannell is a writer who specializes in the arts, culture, special events and creative & innovative projects of all kinds. As Director of Communications for the tech start-up eventwist, she also manages their blog. Some of her favorite work is featured on, and her own blog, Currently she is preparing to launch Project Mavens, a content branding firm. On Twitter @projectmaven.

About The Author

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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