Kyle Crawford

Works on Ambiguity





Though we are often told that the way to achieve success is to be loud and clear about our aims, history teaches us a surprising lesson: if you want to make a real impact, sometimes you have to be much more ambiguous.

I have always been fascinated by how people create change, especially those who are up against great odds.

How do they do it? How did they avoid being stopped in their tracks early on like so many others? What can we learn in order to get more of our projects, businesses, and causes to succeed?

From building startups and social movements, to navigating bureaucracies and battlefields, ambiguity is a forgotten secret of success.

Unlocking the timeless lessons of how icons as diverse as Harriet Tubman and Winston Churchill used ambiguity to their advantage, this book shines a spotlight on this long-overlooked strategy of success and making a difference.

Be sure to get your exclusive access to the book’s material before its release...





One of my book’s subjects, Col. John Boyd, was famous for giving a six hour long briefing in which he discussed, among other things, the role of ambiguity as an advantage. Though Boyd wrote almost nothing in his lifetime, he gave this briefing hundreds of times and his thinking has since been used by people in more industries than you can imagine.

With much of the conceptual underpinnings of the book complete, I am beginning to speak more regularly about the value of ambiguity for achieving success.

These talks include powerful examples and give you answers to questions like...

  • Which patterns of thinking help and hinder your team’s ability to respond to uncertainty?
  • How can you use ambiguity to succeed when up against bigger and better resourced competitors?
  • What is the process of planning and acting history’s heroes have used to make an impact on the world, and how can you use it too?

Ambiguity talks are rich with actionable content, entertaining, and eye-opening for teams.

If you think this type of discussion on ambiguity might be valuable to your team, I invite you to connect with me or learn more...


Interested in scheduling a talk?


Digital Marketing and Fundraising




( select list )


Customer Acquisition | Copywriting | Product Management | Content Strategy | Email Campaign

Kindful has been on a tear, bringing high-quality analytics and automation to social impact organizations through a powerful CRM product. With customer acquisition growing steadily, plus a number of big integrations with services like Stripe and Zapier, they raised a $3.5 million funding round in 2016 to usher in the company’s next stage of growth.

One of the timeless challenges of scaling a company is that usually the strategies which get you to a certain stage are not the same as those that will take you to the next. Kindful was beginning to face this realization. The early adopters understood the power of a great tech product. But nearing 1,000 organizations using the tool, they realized the next set of customers were going to need much more education before joining.

As a team of technologists, Kindful needed somebody who understood their technology and users, and could communicate the concepts underlying the product in a way their prospects would be excited about.

When we first began talking, they were interested in putting together an ebook. But as we analyzed their goals and new directions in digital marketing, we decided it made more sense to do a drip email course. Focused on explaining the benefits of automation for their target market, and then introducing the prospects to new tools and useful step-by-step guides, the course would progress people towards a Kindful demo.

The lessons included:

  • How to create more urgency in your appeals

  • How to save loads of time on donor prospecting

  • How to deepen relationships with personalized automation

  • How to find and use better web-based tools

  • How to run a more efficient organization with simple automations

You can get access to the email course by going to:

Partner Relations | Program Development | Digital Marketing | Program Evaluation

The Forbes Funds is one of the more unique philanthropies in the US. They are constantly iterating on their strategies for creating social impact, launching new partnerships and programming, and embracing innovative new models for funding. Recently, The Forbes Funds along with BNY Mellon, launched the UpPrize, a social innovation competition for entrepreneurs dedicated to making a positive impact through their companies.

It is no wonder I have long been attracted to this organization’s work. Back when I was in grad school, I built an evaluation system and authored a national benchmark report on business planning and strategic planning cost discrepancies for The Forbes Funds.

When I was brought in recently, the organization was undergoing a period of significant growth. In addition to an expanded staff, The Forbes Funds was in the midst of an executive transition and beginning to work more closely with the startup community. With all of this going on, programming had fallen through the cracks. They needed somebody who could jump in immediately and manage and market dozens of events on their own. To operate such a portfolio, I also introduced tools for streamlining the programming management process.

Because The Forbes Funds audience was expanding, the programming needed to include more comprehensive offerings. Rather than providing more general opportunities which would appeal minimally to lots of people but strongly to no one, we focused the strategy around increasing the number of targeted programs. So on top of traditional capacity building areas, we helped organizations navigate changing trends in technology, funding, policy, and research by partnering with cross-sector leaders.

The new programming successfully served its diverse audience that included people ranging from social entrepreneurs and nonprofits, to banks and venture capitalists. With this approach, The Forbes Funds enjoyed an increase in attendance by more than 300% over the prior year.

Multi-channel Campaign | UX design | Fundraising | Copywriting | Social Media | Project Management

For more than 20 years, Food on Foot has been getting people off the streets and into full-time jobs and their very own apartments. Even more incredibly, they have managed to do all of this without accepting a dime of government funding. In place of bureaucratic red tape, Food on Foot has built up a base of supporters who believe in both the mission of helping the homeless and for how the organization has chosen to do its work. These supporters range from youth volunteers to major public figures like Demi Lovato and Bob Odenkirk.

Even with such a strong audience, the financial recession was causing members of their $98 Club - people of pledge to give at least $98 a month for 12 months or more - to cancel their giving unexpectedly. While new supporters were still coming in, giving suddenly began trending downwards for the first time, and little was working to stem the decline. 

For an organization built on recurring revenue from individuals, this posed an existential threat. Is this business model without government funding still sustainable?

Jay Goldinger, Founder and Executive Director, reached out to me to find a way to establish new growth in the organization’s fundraising. We got right to work, running a series of analyses to understand where the problems of donor retention were really coming from, and then developing a number of solutions.

The first place we focused was on redesigning the online giving page. Because Food on Foot relies on recurring revenue from online gifts (upwards of $40k/month), making this page as user-friendly as possible was critical. The current page had excessive content and used a design that de-prioritized giving. We cleaned up the design in order to boost online giving by writing more compelling content, incorporating video, using testimonials, and modernizing the layout in accordance with current design standards.

We also built a comprehensive and coordinated multi-channel campaign that synchronized a series of Facebook ads, an email campaign, and direct mail letters. The team wanted to rethink the format of annual appeals to focus less on desperation and more on highlighting the impact of their clients' hard work and success, and we framed our work around these aims.

Because there are many critical pieces to a coordinated multi-channel campaign, we also spent time on a few additional related areas, such as:

  • Using social media A|B testing to optimize campaign messaging

  • Designing the website to guide users to complete the most valuable calls-to-action

  • Boosting the sponsorship revenue stream by reframing the value proposition and introducing tiers

The results have been impressive. Almost immediately, we had reversed the downward trend in donor retention, and continued to see recurring revenue grow month-over-month from there. By building out and driving people to a specific sponsorship offering, Food on Foot also saw quick revenue boost in this area, including an increase in five-digit gifts, and was able to better highlight their strongest supporters to encourage long-term sponsor retention.

The multi-channel campaign is currently live. Check back in early 2018 for updated info upon its completion.

Storytelling | Marketing Strategy | Content Creation | Interviews | Case Studies

The founder of Epsilon Eight, Chris Eigner, is an amazing person. In addition to serving as the Chief Technology Officer of a blockchain investment fund, he has built software for some amazing companies and government projects. 

His firm, Epsilon Eight is a product development agency based in Denver, CO. They have worked with startups funded by some of the most well-known venture firms in the world, and with companies in the energy, payments, and education industries. 

They had built up an outstanding roster of clients and developed valuable tools for them. But Chris realized Epsilon Eight wasn’t capturing and communicating the impact of their work like they could be. The hard part was in knowing how to make the technical projects come to life.

How could we tell the story of impact their work was having for clients?

How could we make it compelling for their new prospects?

We quickly settled into an efficient workflow, and I went to work coalescing conversations we had about a series of projects into case studies. We made sure the pieces not only conveyed Epsilon Eight’s technical proficiency, but also the story and impact of their involvement on their clients’ own goals.

I structured, wrote, and edited a compelling series of case studies around work Epsilon Eight had done for three clients:

  • An enterprise software company that works with universities

  • A global public-private partnership that works with largest governments and companies

  • A Silicon Valley tech company that works on corporate perks and benefits

We utilized a hero’s journey story arc for each of the cases, highlighting the great reputations of the client companies and the role Epsilon Eight played in helping them solve major technical challenges that were poised to derail their success. Plus we brought in leadership from the clients profiled to provide key quotes, confirm timelines, and give their blessing for the content’s distribution.

Epsilon Eight now has a series of case studies that demonstrate the value they bring to each of their clients which can be shared with each new prospective customer who walks through their doors.

Growth Strategy | Fundraising | Online Course Creation | Project Management | Design Thinking | Retention

Fundraising Genius is an innovative growth marketing course for nonprofit executives and fundraisers.

Having taught new, proven techniques for raising money to people from MIT, United Way, and others, I wanted to put together a complete course that people from organization of any size could use to bring in more money for their causes.

It is no secret that the nonprofit world trails most other industries in terms of technology, strategy, design, and more. One of the big reasons why new approaches are not adopted more readily by nonprofits is that they are not presented in terms people working with causes easily apply to their work. With Fundraising Genius, I wanted to translate the most cutting-edge audience building techniques, design strategies, retention tactics, and more from tech startups for use by those helping our most vulnerable.

The Fundraising Genius Masterclass is a comprehensive course with 24 video and written lessons, 11 custom resources, and much more. It has been used by dozens of leaders from universities and nonprofits, and featured by a number of podcasts and outlets.

You can see more info about the Fundraising Genius Masterclass page here


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Social Innovation


I launched a little thing called Dwilly...

For me, social innovation has not been about simply applying business strategies to social problems. It is about combining things that work from any collection of fields into solutions for the persistent social ills.

In 2015, some powerful insights came together that led me to build a global social innovation community. I knew deep in my bones that brilliant, innovative people were looking for an excuse to solve important social problems. And I knew that if I designed the experience in the right way, together we could generate a valuable set of solutions for entrepreneurs, nonprofits, and governments.

The experience was designed around 3 core human and innovation insights:

  1. People need access to cross-disciplinary thinking, but not until after they generate their own solutions

  2. People want to apply their expertise to problem areas outside the ones they focus on at work

  3. The practice of generating multiple solutions - as opposed to the first one or two that come to mind - builds up a person’s ability for developing more and more innovative ideas

Designed using the “Hook Model” outlined by Nir Eyal (Stanford University) and Ryan Hoover (Product Hunt), people were taken off-guard by how quickly attracted they became to this unique project.

" Waiting 1 day for the next @dwillyco is like waiting a week for the next episode of your favorite show! I'm hooked! "   -  Chris Brooks, Entrepreneur from South Africa, Dwilly early adopter

In less than four months, the community was generating more solutions than the largest innovation communities produce in a year.

I was extremely focused on building and nurturing an active global community of engineers, professors, designers, social workers, and entrepreneurs. Their output was astounding, producing 3,000+ solutions to social problems in short order.

An article I wrote for CMX, the leading network of community managers,  on the launch strategy I used for gaining user insights and growing the community by doing things that don't scale was well-received in the design and tech worlds:

Through Dwilly, I was also able to partner with the innovation department of a major US city to generate ideas for redesigning public transportation. You'll be able to read the anonymized report of the results here soon.


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