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[E4C8] Herding Jaguars & Empowering the Masses to Unleash Positive Social Change

We are here today with Darian Rodriguez Heyman, a social innovator with a long history of building businesses and creating community. Darian is the chief development officer for Better World Wireless, the first mission-driven telecom company aiming to simultaneously serve you as non-profit and donate one million smartphones to moms, teachers, and farmers within the next ten years.

He is the co-founder of Social Media for Non-Profits, a conference series devoted to strategies and tactics around using social media for social good. For many years, Darian served as the Executive Director for Craigslist Foundation where he helped launched their non-profit bootcamp, educated and inspired over 10,000 non-profit leaders.

His best selling book, Non-Profit Management 101: A Complete and Practical Guide for Leaders and Professionals includes practical tips and tools from 50 recognized experts across 35 comprehensive topics.

In this episode, Darian is going to share with us:

  • What it takes to herd jaguars to create a ground breaking work for social change
  • Why taking a six-month sabbatical is a great way to check out while checking in
  • How to dream your dreams with open eyes so you can make your dreams come true
  • Why doing less can actually be the key to making a bigger impact in the world
  • How to be that non-profit that empowers people in lasting ways rather than enabling a culture of handouts.

Mentioned in this Podcast

Where to Find Darian Heyman


Lorna: So Hey there Darian. I’m so glad that you’re here with us today to join me for this interview. It’s been many years since I last worked with you and I’m so glad to have the opportunity to finally catch up.

I remember when you and I first met, you were gathering ideas to launch the Craigslist Foundation Non Profit Boot Camp. Now at that time I was working with Natural World Museum and Social Fusion which is a social venture incubator. I would love to find out more about your background and what led you lead up the Craigslist Foundation.

Darian: Sure, well thanks again for having me Lorna. It’s good to reconnect. It was indeed been a while. Just really quickly, I think of myself as kind of a dotcom refugee. I started and sold one of the first internet advertising agencies back in the dotcom days right out of college. It’s a phenomenal experience. We’ve built a company to almost 400 people in 28 countries. But when the bubble bursts after we have sold the company, we went to some pretty difficult layoffs as a lot of companies did. Then I kind of realized that what I thought was a family was really a business.

I think it’s important to bear in mind that I was the only co-founder out of four that didn’t marry an employee. And we have 22 married couples come out of that company. So it was very tight knit to say the least.

I would up taking a sabbatical and going on a travel around the world for six months. While I’m always doing that I really made a pretty firm decision in terms of the direction I wanted to take my life in to sort of use my power for good and I decided to dedicate myself and my life to philanthropy and to the arts. And that’s part of what led me to do some work with Natural World Museum which is how we got to collaborate on World Environment Day. But it’s also what led me to restart the Craigslist Foundation and in particular the Non-Profit Boot Camp.

For me, I think the idea was really, how I could make the most positive impact possible. The personal mission statement that I came up with while I was traveling was all about maximizing my sphere of positive influence and had this epiphany that everything we do or don’t do creates change. That’s true with the nature of life. This change emanates from us in all directions like the ripple in the pond. But actually, circular and three dimensions. So knowing that how can we harness that and really contribute to significant and sustainable social progress.

For me, Craigslist was really an opportunity to partner with the hugely well regarded, well known platform that a lot of people especially in the Bay Area know and love.

And to take something that was very idealistic and applied to an even more idealistic landscape like the non-profit sector and so, rather than steer them towards supporting one individual cause or organizations like foundations traditionally do, for me, Craigslist doesn’t really play favorites and so it’s kind of an egalitarian approach to people helping people to the non-profits based. I came up with helping people help and really connecting emerging leaders, the little guys with the resources that they need to build a better world. And that’s what Non-Profit Boot Camp was all about. It was really successful.

The five years I was there we had over 10,000 graduates. Ninety two to a hundred approval ratings. It was the largest non-profit gathering in history within a year of its inception. And just to really transform an event here in New York. So the book that I just put out Non-Profit Management 101 really builds on the relationships and the knowledge that I gained and my experience. It features 50 different authors across 35 topics so it’s very much like boot camp as a book. It’s trying to take this approach to being very comprehensive and at the same time really practical, which is what boot camp is all about.

Lorna: So how long were you with the Craigslist Foundation?

Darian: I was there five years.

Lorna: And when did you leave?

Darian: 2009. So 2004 to 2009.

Lorna: After you left Craigslist Foundation in 2009 where did your path take you?

Darian: Well, I had also become a commissioner for the environment for the City and county of San Francisco. So I’m pretty active in the whole [6:49] space. [6:52] was at that time the largest solar rebate program in the country and so I won’t on another sabbatical. Took another six months to travel the world and decide what I wanted to do next and really decided that I wanted to focus on the green economy space but also, kind of put a bookend, literally and figuratively on my time at Craigslist Foundation.

So I put together this book project. We actually had a proposal from Wiley in the past which is the largest non-profit publisher, to do a non-profit boot camp book. But we just didn’t have the capacity to take that on at Craigslist Foundation. So when I left, I got the board’s permission and blessing to do that as a solo project to really put the details together while I was traveling. And also decided, I wanted to focus more on the green economy space and started doing a lot of work with the UN environment program, speaking for them on different summits around the world and helping facilitate some green economy gatherings and then came back and really started this renewed focus on non-profit and environmental consulting working with organizations to help them with strategy messaging and fund raising.

Lorna: So this book project came to inception while you were still at Craigslist or just transitioning away. Is that what turned into the Non-Profit Management 101 book that you just launched?

Darian: Exactly. Yeah. So, while I was travelling, I was thinking through who the different authors, what are the different topics, how do we want to structure the table of contents, what was the consistent chapter formats so that it would be more readable. There’s a set format where all of the chapters start with an overview and then really focus on critical skills and competencies, have a side bar of dos and don’ts, a conclusion. Every chapter has a resource review for more information.

So the idea is that even if it’s a pretty big book, it is comprehensive, it has about 700 pages but it’s very modular so you can read each chapter in 20 minutes. If you just want to know about how to raise money for foundations, CRM or non-profit finances, or board governance, etc. You can read just that one chapter.

Lorna: I was pretty amazed by how large this book is. It seems like it’s quite an endeavor. How long does it take to create a book of that magnitude?

Darian: It was a couple of year project. It was definitely a lot of heavy lifting. I joke around in a lot of the facilitation work that I do and said that it’s not about herding the cats, it’s about herding the jaguars. And so for me, the book project was a really great opportunity to work with some amazing people like Paul Hawkin and Lynd Twist and Beth Canter and lots of industry luminaries and to help guide and direct them towards this aim of practical tips and tools.

And that’s really kind of a theme in all the non-profit management work I’ve done at Craigslist Foundation, with the Boot Camp, with this book, with the Social Media for Non-Profits Conference series I’m doing now and I feel like there’s a lot of people out there talking about concepts and theories and basically how to think about an issue. But what I found the community leaders really need are the actual tool, tangible tools, the actionable insights they can put to work immediately and make them more effective and efficient in the work they are already doing.

Lorna: Yeah, I think it’s really cool that while the book is almost 700 pages, it seems to be almost entirely written by other people which is amazingly brilliant from an execution standpoint. Was it fairly easy to round up that group of change making luminaries? What was the process like? Was that the easiest part? Was that the most difficult?

Darian: It was a lot of work. I mean, there’s 50 different authors and every time you try and get 50 people to do anything it’s going to be difficult especially when they are really some accomplished and dynamic figures that have a lot to say.

There were some folks that colored outside the lines and I had to work with them to get their chapters into the consistent structure so the book would be as readable as possible. There were some folks that didn’t work out. But on the whole, I’m really glad with where we wound up at the end of the day, in terms of how the book turned out.

It was absolutely a process. I did do quite a bit of writing myself. I did an intro to the book to each of the seven sections, closing thoughts and then I also edited the whole thing.

I went through every page of every chapter several times and gave the writer’s feedback in terms of directional but also focusing on those practical tips and tools. So it was quite a bit of work but it was a really great opportunity while I was outside of my full time employment and traveling around the world to put some time and some thought into really encapsulating all the relationships and the knowledge I gained while I was at Craigslist Foundation.

Lorna: I love the whole concept of taking six months sabbaticals, traveling around the world in order to just kind of get into a clear space to have a space to reflect on all the great things that you have accomplished in the past. Then really appreciate yourself for all the hard work that you’ve done and to be able to open to new ideas.

What do you like to do when you go off on these sabbaticals? Do you go and just travel freely? Or do you actually go and associate yourself with a project to try learn a new discipline?

Darian: I guess it’s a little bit of everything. I almost think of it as leaning to the universe. As a serial social entrepreneur that’s used to building up organizations from nothing and in particular someone who’d be on just being an executive that tends to be in a sales, fund raising business development kind of rainmaker role.

I tend to be in a role or I put myself in a role where I’m responsible for the livelihood of everyone around me. And while that’s tremendously rewarding, it can also be draining specially over time. And especially when the economy gets rough. For me, when I travel, it’s a great opportunity to just not be responsible for myself and other people.

I like to travel without a guide book, without an itinerary. Not necessarily know where to sleep the next night. I just have backpack and travel around and meet people. Ask them what the coolest things they have seen are and then just go.

The mantra that I like to embrace while I’m on the road is embracing serendipity. And so for me, it’s an opportunity to just experience the world and its people, sample the cuisine, sample the cultural sights and really just see what comes and travel pretty lightly but be prepared for just about anything.

I find that it’s incredibly reinvigorating and just allows me to check out but check in with myself at the same time. And in so doing, I tend to, at some point get to a moment where I find some pretty significant clarity. I almost think of it as epiphany hunting, if you will.

Lorna: I love checking out to check in. Actually, I’m just on the verge of my own sabbatical. So I feel like I really resonate with you on that. I’m so excited. Where did you go last?

Darian: I was all over. I was in 14 countries. I started out in Latin America then I was in the Middle East then finally in Western Europe and Morocco.

It was all over the place, from Cuba to Turkey, to Peru, you name it.

Lorna: Wow, very exciting. So going back to all your rainmaker stuff. I think it’s really great that you’re one of those people that can influence a lot of other people that have the ability to make things happen and also have resources. But at the same time, I’m more impressed by the massive volunteer support that you guys were able get to rally behind Craigslist Foundation.

Most organizations can’t even find a handful of volunteers. Id love to hear some of your advice or best practices on how an organization can do this and achieve the massive success that you guys have.

Darian: I think to be fair, it’s important to recognize that Craigslist Foundation carries this tremendous brand behind it. Craigslist is one of the top 10 websites on the internet and more importantly, it has a cold following because it really represents a different way, a different model of capitalism, if you will. It’s very community driven and so we had to literally turn thousands of people away that would love to volunteer for us.

It’s not necessarily a typical non-profit story, specially since now I’ve worked with thousands of groups. Most people don’t realize that 75% of all non-profits have budgets underneath $75,000. There’s a lot of mom and pops. A lot of small startups that are grassroots organizations doing really good work. For me I think the most important thing to remember, one of my favorite quotes, Goethe said “Be bold and mighty forces will come to your aid.”

One of the key things or I would say two key things, one is, the importance of painting a picture rather than thinking that people are going to support your efforts whether it’s financially or with their time.

The way that I’ve heard one of the authors of my book put it is that, “People don’t give to you because you have needs, but because you meet needs.” And so, it’s really about mapping the contribution to impact and helping people to understand that by supporting your efforts you’re basically acting as a conduit to achieve some kind of change that they want to see in the world. I think that is a really crucial issue.

On the other side of the coin is this notion of dreaming your dreams with open eyes in order to make them come true. And this is a concept where all too often we’re so busy reacting and responding to whatever stimulus, whether that’s someone who wants to volunteer or another partnership opportunity that we don’t proactively take the time to envision what is it that we want to do.

I kind of think of intention as be careful where you point that thing because life is really self-fulfilling prophecy. So the concept is, if you’re looking on to bring volunteers, you should have a job description even though you’re not paying them. And you should also take the time to map out what the duties and responsibilities. What are the requirements? How is this relationship going to work? Who is going to manage them? Etc.

So all of those things are thought through ahead of time. Once you bring that kind of mindfulness to your work, amazing things become possible. And for me, that’s the big part of why I take this sabbaticals because it gives me an opportunity to take a step back and think about what I want instead of react to just what comes.

Lorna: I really love that. I think there’s a lot to be said about the law of attraction specially when it comes to social change work. I think it’s so important because a lot of us do social change work not for a paycheck. It’s because we are trying to be a positive impact. We are moved by what we see in the world and we want it to be a better place. And so, for a lot of us the work is also not only external, it’s very much internal.

Darian: Yeah, and I mean, I think the theme that I see a lot of, one of the most common pieces I give non-profits is do less. And I think the idea is that, just based on the very fact that we are working in this sector, whether non-profit or social enterprise or any kind of philanthropic initiative, that by definition makes you a compassionate person that wants to make the world a better place.

Although it’s a bit sad to admit, the reality is, there’s no shortage of problems that needs fixing in the world. And so if we allow ourselves to be distracted and essentially dilute our efforts by chasing after every shining object, every opportunity to serve while in some ways that is laudable, in other ways it does dilutes our efforts and it minimizes or at least diminishes the possible impact that we can have.

So for me, I think the question is really about leverage and about focus. If you can only do one thing, what’s the one thing that you want to do and what’s the one thing that you’re prepared to be the best with the world. What’s the one thing that you can really make a unique difference at?

Lorna: Yeah, speaking about impact. So going back to maximizing impact, I find it really interesting that you just mentioned 75% of non-profits operate with less than $75,000 I’m kind of curious as to the whole way that non-profits are able to make so much more happen with so little.

There’s definitely an art to it and I see having been in the non-profit sector, having been in the for profit sector that while a lot of non-profits are able to achieve miracles to the force of passion and goodwill, at the same, non-profits often have the stigma of being inefficient in financial management, in organizational strategy, in operational efficiency specially if you are looking at it through the lens of the for profit sector, the business sector.

And a lot of people criticize the charitable sectors enabling a culture of handouts or being destructive of local industries. A very classic example is, the really well intentioned donation of mosquito nets to combat the spread of malaria in African countries and how that just ends up destroying the local mosquito net industry.

What are your thoughts about all these and how do you not become one of those non-profits?

Darian: I think that there’s a couple of different issues that you’re bring up. One of the sort of classic mistakes that larger and/or international non-profits tend to make in international development work is this top-down approach to philanthropy as opposed to going into a village and asking them what kind of help they need. We sort of take this culturally imperialistic approach to saying, “Oh, you poor thing, you just have an earthquake, let me come help you by building houses that look just like the real house in my neighborhood.” And people don’t want that.

I think that the important thing to realize is that, very few people see themselves as victims. Even though we may, they don’t necessarily think of themselves in that way.

I worked with organizations like Cuba.org These people that they are helping are not victims. They are just looking for hand up instead of a hand out. The other thing is, the work that I’ve done with the [21:03] I’ve been to Ahmedabad, in India where there was a massive earthquake and racial riots and all these problems. And what did the international development community do, but exactly what I just said. They came in. They built these huts that’s Western style and I saw people living in the streets right outside these huts. They were totally empty because they weren’t built to the cultural specification of the locals.

I think this happens a lot. Whether it’s in Haiti, whether it’s with the tsunami in Japan, etc. And we really need to make sure that we’re working in partnership with local industry, with local citizens, with local governments to really build the community in a world that they want to see happen if we are to truly serve.

Lorna: Can you give some examples of extremely efficient, high impact innovative you’ve come across.

Darian: As it relates to the non-profit sector, there’s a huge need for business acumen. And I won’t be one of those people that’s going to say that non-profits need to be more business like because in many ways, for profits sector needs to be more non-profit like. But what I will say is I once heard as a rule, as a generalization, the non-profit sector is overlaid and undermanaged. And I find that to be very true.

We have a lot of charismatic, dynamic, visionary leaders that can paint a beautiful picture, get folks excited, recruit resources and money and personnel and boldly proceed towards the vision. But when it comes time to operationalize that vision and build out the key systems, whether that’s performance indicators, whether that’s any of the things we may learn in business school, a lot of those tend to be absent in the non-profit world. So there’s a huge opportunity, whether it’s through people with business backgrounds working in the sector or just volunteering their time for groups like [22:53] Foundation or Full Circle Fund or joining a board which is something that I’d recommend.

And so the point is, I don’t believe in this concept of “slacktivism” I’m aware if you just click to sign a petition or like us that that should be discounted. For me, it’s all good and it all helps. And people interact with different causes, in different ways, at different times, in different context. And so, if something speaks to you and you want to get involved then get involved in whatever way you feel most comfortable and if you feel so cold to join the sector and take a leadership role and take a full time engagement at a non-profit then that’s wonderful. If you’d rather do it as a volunteer or board member or any other kind of adviser then that’s wonderful as well.

Like I said, we need all the help we can get.

Lorna: Well thank you so much for taking the time to speak with us today. This is Lorna Li, the editor in chief of Entrepreneurs for a Change. We were just with Darian Heyman who is a dotcom refugee who led up Craigslist Foundation and launched the wildly successful Non-Profit Boot Camp. He’s currently a non-profit and environmental consultant and the author of the book, Non-Profit Management 101. To find out more about Darian, go to socialmedia4nonprofits.org or nonprofits101.org.

Darian:Thank you.

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