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Virtual Skoll World Forum | Black Fox Global | Attracting Bold & Big Bet Funding

Filed in Relationship Advancement — April 28, 2020

In our blog we’ve pulled back the veil on our approach and methodologies through a largely ‘plug and play’ resources and Masterclasses so you can skillfully engage the funding partners your mission deserves.

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Weeks ago, we had plans to publish an exciting report, Bold & Big Bet Philanthropic Landscape, here on our blog. This report, compiled from the findings of a series of generous and candid interviews conducted with major funders across the sector, and in-depth research and analysis, seeks to answer the question  “What inspires institutional philanthropic entities to invest at their most significant level ($1M+) in a single organization, project, or program?” However, before the finishing touches of the report were made, the sector (and the rest of the world!) began to feel the effects of COVID-19.
To ensure the safety and wellbeing of the community, the brilliant folks behind the Skoll World Forum made the brave and wise choice to pivot the convening to a virtual forum and appealed to the “brain trust” of the Skoll ecosystem to deliver a robust week of learning and collaboration. When the invitation to present an ecosystem event was offered to Black Fox Philanthropy, the would-be blog post was converted to a 75-minute webinar, Fundraising Roadmap | Attracting Bold & Big Bet Funding. Presented by Natalie Rekstad, founder and CEO of Black Fox Philanthropy & Kimberly Westerfield, the Partnerships, Programs and Grantmaking Manager at Western Union Foundation (and formerly of the Skoll World Forum), this session offered valuable insights and tools to accelerate the pace in which participants might engage in more sophisticated and transformational funding. We wish to extend our deepest thanks to the Skoll World Forum team for inviting Black Fox Philanthropy to be a part of such an impactful week.
An audio recording of the webinar may be found HERE, with a link to the slides HERE.
Some of the resources referenced in the session include:
Additionally, we are pleased to share the full report below, as part of our open-source model.


Prepared by Natalie Rekstad & Kimberly Westerfield


The guiding question for this report is: “What inspires institutional philanthropic entities to invest at their most significant level ($1M+) in a single organization, project, or program?” 

In the most recent ‘Trend Shifts in Ultra Wealthy Giving’ report, Wealth-X estimates that there are more than 212,615 ultra high net worth individuals (UHNWI) in the world, worth a total of more than US$30 trillion, and of these, 18,500 (8.7%) are estimated to be major donors – as defined as those who have made a significant gift of at least US$1M to a philanthropic cause or organization in their lifetime. Additionally, 85% of the top 20 billionaires from around the world have their own philanthropic foundations as a vehicle for their giving. Given this information and conversations held with our client, we focused our research on the institutional philanthropic market. 

Bold and big bet funds are every organization’s dream, for many reasons. Bold and big bet funding requires less administrative overhead for organizations in the long term and therefore, rather than having to process, report-on and manage numerous smaller gifts, organizations are able to work with fewer and larger giving partners which tend to cut processing and relationship management time down significantly, freeing its staff to do more mission-critical work. It also gives organizations more of a runway allowing them to plan and execute against the complex issues they are working on. There is never a convenient time to focus solely on fundraising, especially when half of the average organizational leader’s time (at minimum), is focused upon it. This naturally puts other key priorities and livelihood-dependent programming at risk. Bold and big bet funders also tend to be more engaged, passionate, and willing to champion for (especially amongst other funding peers) the organizations they invest in at such a level, which often results in more funding and positive exposure, given that word of mouth (WOM) is still the most effective marketing tool in the space. It also allows for a more productive collaboration given the strong incentive for engagement from both sides, which can expose opportunities for funders to assist an organization beyond their monetary gift but also in providing aligned and essential technical assistance, filling gaps, along the way.

However, from a funder’s standpoint, bold and big bet gifts also tend to come with a lot of responsibility and risk which make this kind of practice more of the exception rather than the rule, especially amongst philanthropic institutions. Therefore, these kinds of opportunities are often few and far between in the grantmaking space.  While there tends to be more of a burden on the receiving organization’s upfront time investment i.e. long labor-intensive applications and a more rigorous due diligence process, there is also a much larger pool of interested applicants amounting to much lower odds of being selected as a bold and big bet partner. And while this is the current reality, according to Wings’ January 2018 Report, The Global Landscape of Philanthropy, it is stated that philanthropy’s purpose is best (i.e. has the greatest impact) when used to do one of the following things; innovate, fill gaps, support civil society and/or act for the long term

So why is this not what we are seeing in practice on the whole? For starters, so much decision-making depends to some degree on an institutional funder’s willingness to take risks. According to the same report, most institutional foundations around the world are either risk-averse or much more risk-averse than they are willing to admit to themselves and/or express publicly. While we are seeing bold and big bet opportunities going in an upward trend, they are inching along that path slowly and, let’s face it, the world today is anything but slow, especially when it comes to all of the issues and problems NGOs are desperately trying to address.  This is amplified enormously in the era of COVID-19.

Given these less than ideal realities, at present, there are still some ways to stand out and better position oneself for a bold and/or big bet investment. This research draws attention to some key competencies of organizations that have successfully secured such gifts from institutional funders. A few important aspects to consider, and as suggested by a panel of bold and big bet funders that were interviewed for this report, can be summed up as follows:

  1. Have your House in Order
  2. Have a Clear and Credible Pathway for Change
  3. Support this Path with Evidence and a Sound Financial Plan
  4. Have Strong Leadership

     1. Have your House in Order

Operationally and financially it is important to have good records and structures that give a sound financial and healthy organizational narrative. Funders looking to make a big bet investment want to know that you can handle it and scale with ease. Having a track record that shows sound stewardship, resourcefulness, and wisdom around financial decision making is paramount. Just as important are the operational aspects of the organization (especially, human resource management and culture) and how key departments are structured to support the organization’s programming and values. Funders will, of course, look at senior staff, board, and leadership overall, but they will also look to see if an organization is strategically structured (not based on personality, familiarity, nepotism, legacy or anything else) to ensure effectiveness and accountability. At times they will explore if there is a plan for protecting and promoting diversity and equity. Having sound cultural guardrails in place that protect the organization from an “abuse of powers” or other potentially destructive forces, needs to be apparent and practiced in order to put prospective funders at ease. Both of these elements need to not only be documented and clearly communicated across the organization but also should be known and experienced amongst staff, peers, partners, employees (past and present) and other people that come in contact with the organization. Some ways institutional funders collect data to analyze the strength of an organization’s operations, culture, and finances are:

      • Running OFAC checks on staff and board members 
      • Reviewing and requesting audited financials that show an organization’s cash reserves, their restricted vs. unrestricted assets, and income streams
      • Reviewing and requesting board minutes
      • Speaking to other funders to hear their opinions and share due diligence 
      • Speaking to the organization’s past and current partners
      • Speaking to the organization’s past and current employees
      • Speaking to similar practicing organizations and/or experts working on similar issues and or in similar contexts
      • Site-visits/in-person audits to meet key staff members and see an organization’s operations in real-time
  1. Have a Clear and Credible Pathway for Change

A recent body of work done by Bridgespan called “Becoming Big Bettable” describes a credible pathway as, “how the organization believes it can get to its five- or 10-year point of arrival (5-10 year plan) where concreteness and practicality show themselves and where social change leaders increase the odds that they will actually achieve their goals.” Your near and long-term plan/pathway for impact and achievement must be succinct and a recipe of optimism, expertise, feasibility, and boldness. As a framework for brainstorming, your 5-year point of arrival can be the more tangible part and a jumping-off point towards your 10-year point of arrival, which can be more broad and ambitious. Clearly communicating your plans is just as important as the plan itself and being able to balance how you share your expertise in a way that reflects a deep understanding of the context in which you do your work, while also considering that the audience doesn’t necessarily have that same understanding, is much more of an art than a science. One place to start is making sure you know your audience. Do your own research and due diligence on the funder that you will be speaking with and ask yourself the question: What might be their top priorities and goals?  Many funders have expressed frustration in regards to this part of the process when there seems to have been little thought and time put forth to best determine shared alignment. Think of this as part of what makes your organization credible. Be strategic about which funders you are targeting and mindful/informed as to when to engage in order to increase your chances of catching their interest. First impressions are heavily weighted.

  1. Support your Pathway with Evidence and a Sound Financial Plan

An institutional philanthropist once expressed that “any NGO with an operating budget of over a 1 million USD has no excuse to not have a robust impact measurement practice, especially given today’s technology” While this sounds harsh, it does make sense if that organization is seeking more robust funding. If you are an organization working on a complex issue and are building services to help address it, it is paramount that your programming is being informed by objective evidence and healthy feedback loops. 

Most philanthropist’s north star is “first do no harm,” especially in the institutional space, where remaining accountable to the public is how they maintain their legal operating status. How can an institution be accountable to their stakeholders if their grantees are not accountable to them? How do they know that the interventions used by “the experts on the ground” are moving the needle and working towards solving issues rather than perhaps creating more issues? 

We’ve all heard the horror stories of this going awry, it is sadly what often ends up breaking through the news cycle more often than the stories of good and effective work being done by NGOs globally. No one wants to be associated with the former and most of us that work in the sector know that so much of development is like a game of “whack-a-mole”, as one funder put it, meaning that the minute one problem is fixed another is created. Being conscious of this, not only the interconnectedness and complexity of societal problems but also that more often than not, this is an honorable place from which many funders are coming. Wings reported that while “Strategic philanthropy is (still) on the rise, bringing with it an increased emphasis on measuring impact, some view this as potentially harmful.” Yet, impact reporting is a key component of accountability and this is one of the only tools in which many funders are able to not only satisfy their key stakeholders and benefactors but also to keep their legal status and ability to do charitable business in future years to come. It is important to understand not only to what level and to whom most philanthropic entities are accountable, and in light of this understanding, seek to honor and align with such parameters as you seek out your funding partners. 

On the flip-side, there is widespread recognition that at present, “All the statistics we have state that most funding goes to the safest areas – education, children, healthcare – not human rights”. The reason being that it is quite difficult to measure human rights, especially when an NGO’s interventions are preventative in nature and not responsive. It is difficult to measure prevention and therefore far more difficult to sell.  Additionally, another challenge is that it can be difficult to measure across geographic borders where there are different legal structures and regulations for philanthropy and NGO entities. You won’t get the clean comparison of measuring apples to apples. While the growth of cross-border philanthropy is impressive, the legal environment and other factors have limited global philanthropy from reaching its full potential. Indeed, “[philanthropic] institutions are not functioning optimally, constrained by policies, accepted practice, and legal and structural limitations.” According to the Council on Foundation’s “Legal Framework for Global Philanthropy: Barriers and Opportunities”, which include constraints imposed by the “donor” country on the outflow of philanthropy, as well as constraints imposed by the “recipient” country on the inflow of philanthropy. Global philanthropy is also impeded because some countries constrain the development of civil society, including the development of foundations and potential grantee organizations. 

We’ve seen most recently legal disruptions come into play with China’s Charity Law and India’s CSR Law. Considering all of the above and the fact that being able to measure and report on education and healthcare is a much more straightforward task, it makes it all the more important to have a sensical measurement, evaluation, and learning department that can help you pull even accurate anecdotal evidence that supports your case. Being able to report and prove impact is what allows most foundations and their staff members to champion for select projects and programming and therefore deploy more funding. So even though it is more difficult to measure impact in say the human rights space, making robust attempts to communicate your efforts to do so will help tremendously in bringing in more funding and at higher levels of capacity. 

The only thing missing from a bold and audacious world-changing idea is a complementary smart and realistic financial plan to fuel it. Another informed way to help mitigate risk for your funders is to explain how you plan to scale your income and revenue as you scale your programming and impact. A key way to think about this is by first considering the different kinds of capital available to you and what combination of, and timeline for, pursuing this capital makes the most sense for you at different points of scale. Social change capital can be broken down into the following segments: ultra high net worth individuals, UHNWIs, and high net worth individuals, HNWIs, institutional philanthropy, the capital markets, and government funding. The graph below shows how much from each segment was invested/deployed towards social change causes on average between 2015-2018 by those who have the capacity to make big bets.

You’ll also notice in the graph that there are arrows that show how some segments move through the pyramid to become part of a different segment. An example is; at the end of a wealthy individual’s life, they seek to continue to make an impact beyond themselves through their children and therefore move from the UHNWI or HNWI segment, where perhaps the vehicle for giving was a donor advised fund (DAF), to the institutional philanthropy segment, so that their name and legacy will live on beyond their lifetime. You will also notice that many philanthropic institutions are now dabbling in impact investing and therefore moving more towards the capital market space. Corporate foundations also sit close to their respective Corporations which are part of the capital marketplace and, therefore, if you are already engaging with someone in a Corporation you may be able to unlock funds from the Foundation and vice versa through this individual making an introduction. This graph is meant to help grantees think strategically about how and when to unlock different types of funding and what is available to them overall. Additionally, it helps to think about diversifying your funding sources as many funders have expressed that the more diversified a grantee’s funding/revenue model is, the less risk they feel they are taking on. Generally speaking, funders giving bold and big bets still want to be sure that their gift is no more than 20% of the total revenue/incoming gifts expected to come into an organization over the next few years.  

  1. Have Strong Leadership

Leadership is probably the most important part of becoming bold and big bettable because oftentimes it is the leader who attracts the attention of funders initially.  And as important as development staff and teams are, most big bet funders will want to engage more directly with the one or two founders/leaders at the helm of the organization, at least on the outset. There are many leaders that have the charisma and ability to get in the door with key funders.  Once this happens, the former points become more important in order to secure the funding. Still, in many cases getting the meeting can be the hardest part and this is where leadership plays a vital role. Many of the funders we spoke with touched on this aspect in great detail, expressing that the following are some of the key things they look for in a leader (as described in their own words): 

Commitment, Passion and Humility

“Does this person have charisma, are they a compelling person, do they have the character of a leader? Is there kindness and generosity about them? Do they come across as ready to make it happen and don’t have arrogance about doing so?” 

“If you look at which organizations are established you see charisma and confidence mixed with a solid trajectory, someone who has been perceived as being in the same work for decades” 

Depth, Context and Expertise 

“Can this person have an in-depth and great conversation? Do they know who the other players are and where their organization stands amongst them in the field? Do they know the major issues and context well enough?”

Conviction, Character and Reputation

“Often our staff will talk with others about an individual leader and their organization to figure out if they are someone you want to be in business with. Some of this speaks to the question, are they smart and funny (compelling) but also seeks to find out what the founder’s story is. How did they get into this work? What leads them to what they are working on? How does their staff interact with them? How do they interact with staff? To do with engaging with my foundation, do they treat (for example) the receptionist with as much respect as they treat me?”


Many funders are now prioritizing gender. Research has shown that there is still a large gap between women-led and male-led organizations when it comes to who is receiving the bigger piece of the philanthropic pie. Further, research shows that women tend to be more resourceful with the funds they are given and therefore can do more with less, which is something that should be very attractive to philanthropic gift-givers. We won’t get into the systemic reasons why this is the current state of play, but wanted to highlight that there is a strong consensus amongst the bold and big bet funders that we interviewed in their desire to be more intentional about investing in more female-led organizations in order to close this gap and disrupt the current status quo.

While the aforementioned attributes can help position an organization for bold and big bet funding, further investigations reveal that relationships and connections still take precedence. This means that even if an organization has all of the aforementioned attributes, if they do not have access to the right people, they will have a much harder time (if given the chance at all) of securing bold and big bet gifts. Therefore, it is safe to say that the most important element in decision making for any organization is trust, which comes with a sense of familiarity, consistency and intentional relationship management. Quite a few of the funders we spoke with mentioned that if they are not familiar with an organization and have not funded them in the past, it is unlikely they would place a bold and big bet on them. There, of course, are exceptions, such as when an organization is a collaborating partner with another organization that happens to already be a grantee of a foundation, or if there is a request for proposals very specific to a certain issue or issue area so new grantees are looked at more closely and equitably, but it is more likely that foundations will first give a smaller “get-to-know-you” grant to begin building the relationship before giving a large lump sum. 

Additionally, foundations rely heavily upon their peers and other credible practitioners that they already have strong relationships with to source their bold and big bet grantees. In the case of Co-Impact, the organization has an experienced in-house team dedicated to sourcing, vetting, and providing deep, ongoing support to initiatives. Audacious consults with a panel of expert advisors that, in many cases, have been grantmaking at their own institutions for years. It is rare for an organization that no one has heard of to land in their purview, however, as mentioned by both organizations, this can also be a stumbling block for grassroots international organizations (especially ones where English is not their first language) and is something that these institutions and the overall philanthropic space is actively looking to solve for over the next few years. 


In conclusion, for an organization to become an ideal candidate for bold and big bet giving, it must focus upon effectively building and communicating its impact measurement, path to scale strategy and network. Getting clear and aligned on a theory of change (TOC) (with big bet funding in mind) is the best place to start. Then, testing this theory with current stakeholders, other practitioners/partners, academics focused in the same field of work, and current funders will help to refine your TOC and give practice to how it can and should be communicated broadly and with regard to specific groups of stakeholders. 

Ensure your leadership is solid in the key areas mentioned in this report, but also always evolving to become more effective not only for the organization they are leading but for the sector as a whole.  The leadership team, including the board composition and executive committee’s roles and effectiveness in those roles, will also set an organization apart as it demonstrates a vision and solid plan for strength and impact outside of relying upon the main person at the helm who often plays the role of the “face” of the organization.   

Remembering that every relationship matters and that most introductions are between 3-6 degrees of separation to your next “big bet” relationship should be kept in mind. And lastly, as most fundraisers and CEOs know, consistency is key. Even if a conversation doesn’t end in the level of investment you were hoping for, keep going, keep learning, and refining your approach. Oftentimes there can be a point-of-entry investment that can lead to bold and big bet funding down the line.  Once you are in that stratosphere, the sky’s the limit!