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Strategic Philanthropy

Act Boldly, Give Wisely: Making your philanthropy more opportunistic

By May 20, 2016October 13th, 2021No Comments

This post is part of the Ramping Up for Impact blog series, which digs deeper into topics explored in the primer by The Philanthropic Initiative (TPI) and Exponent Philanthropy, Ramping Up Your Foundation: Key Considerations for Planning and Managing a Significant Increase in Giving. Click here to download the guide through Exponent Philanthropy’s website.

One of the most exciting elements of a ramp up in giving or assets is the opportunity to build a grantmaking strategy that can leverage your philanthropic dollars in ways that create even greater impact. But this opportunity shouldn’t be unique to those funders experiencing a ramp up.

Are you facing a ramp up, or are you just sleep walking through your annual grantmaking? Does it feel like your grantmaking cycle has taken control and you are just a passenger along for the ride? Do you have an underlying sense that you could be making your philanthropic investments go a lot further?

No matter where you are in the lifecycle of your giving, you may be ready to take your grantmaking to the next level of impact. But how do you do it? At the Philanthropic Initiative (TPI) we have helped many clients tackle this question, which typically involves moving beyond grantmaking and finding opportunities to make a greater impact with the same financial resources. While there is a variety of tools and structures that you can use to move beyond traditional grantmaking (a.k.a. annual check writing), here are a few first steps that can help you identify the right ones for you.

Get Close and Listen

Take the time to get to know your grantees. Meet them for a cup of coffee; ask them about the trends they are seeing in the field. If you are interested in getting more involved and moving beyond check writing, your grantees and the people they serve can be excellent guides. A great example of a program that has truly embraced this notion of “getting close and listening” is the Red Pine Scholarship, which was created by an anonymous TPI client. This college success program goes well beyond the traditional scholarship by assigning each scholar a personal advisor. These advisors help support and guide students, many of whom are first generation college students, through their four years of school. Using these advisors as their eyes and ears on the ground, the donor has been able to learn what additional wrap-around supports these students could use, including a “Flex Fund” which allows students to apply for small amounts of funding to cover unexpected expenses. Students may use this fund to buy books and supplies, help pay for study abroad expenses, and cover living expenses for unpaid summer internships. By listening to the stories and experiences of the students themselves, the donor has adapted the program’s giving structure and timeline to best meet the needs of those being served.

Become an Expert

One of my favorite TPI clients is a sarcastic, eclectic, and overwhelmingly passionate group of family members. I know, I know. Consultants aren’t supposed to have favorites, but this family foundation is just too good to be true! The family began as many families do, by exploring a few different areas of interest, trying on different causes and giving strategies to see which ones fit the best. Fast forward ten years: the trustees zeroed in on one of those issue areas – incarcerated parents and their children – and now know all of the players in this field. They know the communities their grantee organizations work in, and they refer to the leaders of most of their grantee organizations by first name.

This family foundation’s dedication to continuous learning has allowed them to act opportunistically to help bridge gaps and leverage resources in creative ways for the people their grantees serve. For example, in recent years the foundation has begun to offer capacity building grants catered to the individual needs of grantee organizations. This past year the foundation provided funding for the leader from one of their grantees in California to travel to New York to train other grantee organizations. This family foundation is not only a donor, but they have also become an active member of the team of nonprofits and advocates working for change in this field.

Take Educated Risks

Could you be next? It may seem scary to invest in such seemingly unstructured and highly involved philanthropy, but that is where your “well-oiled” annual grantmaking machine can play a role. Why not begin exploring these possibilities with the groups and organizations you already know and trust? They can be a great audience for testing some of these ideas and could offer some suggestions for “going beyond the grant” that you had not thought of before.

In March I attended the 2016 Grantmakers in Health conference and enjoyed a session on “Adaptive Funding Strategies” that highlighted the work of The Colorado Health Fund. The session focused on the Fund’s newly adopted strategy that incorporates convenings, multi-year general operating grants, program grants, and rapid response grants all in their strategic funding portfolio. This model is a great example of a funding approach that builds upon the foundation’s relationships with long-term partner organizations to create opportunities for leveraged, increased impact.

While we know that moving beyond grantmaking can be daunting, and that it has its own risks, we hope these stories inspire you to think big and imagine a world of philanthropy beyond the traditional grantmaking cycle. As TPI’s tagline urges, we challenge you to look for the opportunities in your own grantmaking where you can act boldly and give wisely.

TPI has worked with a number of families, foundations, and corporations at various points in the ramping up process, helping these clients successfully navigate the challenges that come with this transition. To learn more about our client work in this area, or if you are interested in engaging TPI’s consulting practice, please contact Ellen Remmer at or Leslie Pine at