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Fundraising & communication strategy collaboration that supports Puerto Rico’s True Self Foundation

Established in 2017, the True Self Foundation works to support LGBTQ+ communities in Puerto Rico. As one of the only organizations of its kind on the island, True Self provides free or low-cost gender-affirming services to gender-diverse Puerto Ricans. They do this work through core programing such as the Be Free Fund, which provides financial assistance for gender-affirming medical procedures for TGNC individuals; the Embrace Program, which offers administrative support for legal name changes, free psychological group therapy, and low-cost individual therapy; and the TransUni Fund, which disburses academic and professional development scholarships. In Fall of 2020, True Self requested the Transgender Strategy Center’s (TSC) technical assistance to support their fundraising and strategic communications initiatives. Felix Endara, a philanthropic expert, and Nico Calvo Rosenstone, a communications strategist, teamed up to supply these services.

Held in conjunction with Pride celebrations, True Self’s signature annual fundraising event is “All Out 5k,” a race through the streets of San Juan that combines sports with LGBTQ+ inclusion, community-building, outreach, and civic engagement. Traditionally, this has been the biggest driver of fundraising for the organization. The funds raised through this event are used to deliver True Self’s programs throughout the year. However, due to the pandemic, the “All Out 5k” was cancelled in 2020.

In our process of discovery about True Self, we learned that the organization has a robust social media presence; and through various platforms, it recruits program participants, engages supporters, keeps the public informed of its work, and drives event-awareness efforts. The organization has used the power of social media to organize digitally in new and innovative ways despite the constraints of the pandemic and inability to gather in person. Given this strong foundation, we agreed that communications plans would thread fundraising messaging as a strategy to capitalize on the potential of grassroots individual donations, especially to make up for the loss of “All Out 5k.”

Although we were still in a planning phase, we lept at a bright fundraising opportunity that arose: #GivingTuesday, a coordinated campaign for non-profit organizations to request online donations. #Giving Tuesday is held on the first Tuesday in December as a counterbalance to the rampant consumerism efforts that launch on the eve of the end-of-the-year holidays. One of the aims of #GivingTuesday is to catch individuals looking to make their tax-deductible donations before the end of 2020. We collaborated closely with True Self to create an online campaign from scratch. The first item on the list was easy: True Self posted a #GivingTuesday request on Facebook. That effort alone raised almost $1,000 in less than 3 days! Our hunch had paid off. Next, Felix wrote copy for an #GivingTuesday e-blast. Meanwhile, Nico organized True Self’s email lists in MailChimp, created the layout and got it ready to launch on that Tuesday morning. Once the e-blast was released, we were poised to collect significant data for Nico to analyze and use to create the overarching communications strategy. We wanted to use this data to build on the foundation that True Self already had in place, instead of reinventing a wheel and starting from zero. #GivingTuesday was a successful experiment and it became an integrated fundraising and communications initiative for True Self. We gathered key takeaways from this experiment:

  1. When providing technical assistance to an organization, be open and responsive to the organization’s needs even before finalizing all deliverables

  2. Take advantage of other already built fundraising campaigns and think how the organization you are supporting might be able to join those efforts

  3. When possible, fundraising support should come with communications support for maximum results

True Self’s Co-Director Omayra Toledo de la Cruz shares the following reflection: “From the get go, Felix and Nico took the time to learn about us as an organization and as individuals and were able to provide the assistance that we needed for our present needs and also for future endeavors.”

Puerto Rico’s transgender and gender-diverse community contends with many of the obstacles that people in this community face elsewhere. True Self recognizes that providing Puerto Ricans with gender-affirming services helps to create building blocks for this community to claim agency over their own lives. True Self allows this vibrant community to gain the strength and resiliency to confront and defeat the external forces that threaten their ability to enjoy lives full of purpose.





Félix Endara is a faculty member for TSC. He is a New York-based bilingual creative professional from Ecuador, who works in private philanthropy and as an independent film writer, director, and producer.






Nico Calvo Rosenstone is a faculty member for TSC. He is also the founder of The Inclusion Practice, LLC, a firm that advises corporations on diverse and inclusive workplaces committed to equity.










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