Cheryl Dorsey

Cheryl Dorsey

Cheryl Dorsey is the President of Echoing Green and a pioneer in the social entrepreneurship movement.

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Last week, Cheryl Dorsey fielded your Twitter questions about pitching investors, growing as a leader, [...]

Last week, Cheryl Dorsey fielded your Twitter questions about pitching investors, growing as a leader, and avoiding burnout. Check out her practical advice and her reading list for social entrepreneurs looking to get inspired.

  1. 747 days ago

    Kristie Wang

    Do you have any advice for social entrepreneurs making their first pitches to investors or partners?



    • cheryldorsey

      Echoing Green is a social angel investor so what we look for in pitches is different than what later stage funders are looking for in a pitch. In the business world, you often hear that angels tend to listen more to the story about the business while veture capitalists (later stage funders) pay attention mostly to the numbers including the company’s traction and performance. Given that social entrepreneurs are in the business of solving problems, I think this description applies as well. At the end of the day, most angels are looking at the individual–we’re always trying to size up the entrepreneur. A key question that any angel is seeking to answer is how much passion does this entrepreneur before me possess? Passion as a form of currency, especially in the earliest stages of starting an enterprise is absolutely critical. If you won’t go to the mat for your idea, values and business, then who will?

      747 days ago


  2. 747 days ago

    Kristie Wang

    Do you have any suggestions for innovators experiencing burnout? We’ve launched our organization after a long period of trial and error, but new challenges keep on coming.



    • cheryldorsey

      This is an incredibly important question and one that gets to the heart of the need to keep feeding both your organization and your soul. I’m not a fan of cliches but it really is true that launching a social enterprise, like any business, is like running a marathon. If you’ve trained to be a sprinter, you’re in the wrong business. I would suggest a couple of things that are vital but very hard for fledging social entrepreneurs to do. First, set boundaries. You could work 24-7 at your new business but if you do you’ll lose a part of yourself and perhaps those around you who care about you but in whom you have to invest time. Second, find that tool that helps you through the journey and let’s you blow off steam when the going gets tough–for some it’s spirituality; for others athletics; and so on. The what doesn’t really matter but the where, when, and why sure do. I would also ask you to shift your thinking a bit. When I read that you’re engaged in a long period of trail and error and that new challenges keep coming, I think–congratulations! You’re running a new enterprise! That’s what it means to set out a hypothesis and then test and refine it in the marketplace. I’ve always liked John Mullins and Randy Komisar’s book, Getting to Plan B: Breaking Through To A Better Business Model. They ask the reader to imagine if the founders of Google, PayPal, or Starbucks had stuck to their original business plans. Mullins and Komisar posit that we’d likely never have heard of them. Because they made radical changes to their initial models they became household names, and delivered huge returns for investors. The book presents a process for stress-testing your initial business idea, and using the evidence you uncover to make swift corrections. Entrepreneurs must be curious and constantly questioning and probing their assumptions and the barrage of data coming at them each and every day. If you can embrace this way of doing business, the challenges that will continue to come (and they will) can be greeted as opportunities rather than setbacks.

      747 days ago


  3. 747 days ago

    Kristie Wang

    How should leaders go about evaluating their own strengths and weaknesses?



    • cheryldorsey

      I’m a big believer in the Pareto Principle, better known as the 80-20 rule. Essentially, this rule suggests that 80% of our results come from 20% of our efforts. Thus to maximize your outcomes it actually makes sense to focus on the most effective areas of your performance and ignore, delegate or automate the rest! I really do think there’s something to this. For so many smart, committed and talented young people this probably sounds like failure at best and heresy at worst. Aren’t we supposed to work as hard as we can and become well-rounded, high-achieving individuals? I certainly asked myself this question and held myself to this standard in my teens and twenties. It was only as I got older (and hopefully just a bit wiser) that I finally had enough confidence in myself to recognized that overall I was doing a pretty darn good job but that while there were things that I was totally crushing (ie, doing a really good job) there were things that I actually sucked at (ie, not doing a really good job at all). More importantly, once I realized it was okay not to be great at everything, it really freed me up to focus on my strengths and hire for my weaknesses. The wonderful thing about your friends, family and colleagues is that most of them are not at all shy about sharing their opinions with you and about you. Take advantage of this friendly audience to get real time feedback on the pluses and minuses of your performance. The real key though is once you’ve received this feedback you actually have to hear it and incorporate it into how you do business. This is really easier said that done but if you choose to do it, it can be a game-changer for your work and leadership development.

      747 days ago


  4. 747 days ago

    Kristie Wang

    Are there any books that you would recommend for entrepreneurs hoping to learn more leadership lessons or become inspired?



    • cheryldorsey

      I will offer three recommendations for books that are prominently displayed on my book shelf at home: 1) Work On Purpose written by my colleague Lara Galinsky and Echoing Green’s Senior Vice President–Work on Purpose provides stories for young people in search of meaningful careers and helps readers to discover what moves them, take inventory of their beliefs, skills and gifts and lock in on their inspiration. 2) The Other Wes Moore: One Name, Two Fates by Wes Moore. I got to know Wes through the White House Fellows Program and was simply blown away by the life story of this Rhodes Scholar, decorated veteran and business leader. Juxtaposed against the journey of another young man from Baltimore with the same name, we see how leaders are both born and made and how vital supporting the next generation is if we are to unleash a new cadre of impact driven leaders. 3) KaBoom!: How One Man Build A Movement to Save Play by KaBoom! Founder and Ashoka Fellow Darell Hammond. Darell’s book is part memoir, part manifesto and provides both inspiring and practical stories of the ups and downs of the social entrepreneur’s journey.

      747 days ago