In 1983, a young Tom Cruise slid across the family room floor with sunglasses on in one of the most iconic movie scenes ever. Risky Business set the stage for decades of spoofs, Saturday Night Live skits, and young adults constant quoting at parties.

In our case, Risky Business is far from just a cult classic. It is how we, as funders, need to operate at times. What we do as funders is risky. We are deploying resources we have been asked to steward. What if we choose the wrong partners? What if the programs we decide to fund end up failing? That is the pressure we face almost daily in the funding community.

Sometimes, this pressure forces funders to become complacent in how we operate. "Well, the results may not be optimal, so we just won't do it."

This is sometimes the tactic that we take. No risk, no problems. But often, when we forget to take risks, we never realize any reward. Bruce Arians, the coach who finally brought a championship back to the Tampa Bay Buccaneers, had a famous saying, "No risk it, no biscuit." Now, this is undoubtedly coach speak and applies much more to throwing the football aggressively down the field than it does to funding our partner organizations or programs, but it is a mentality we need more of in the funding field.

I recently sat in a session discussing risky granting at the Florida Philanthropic Network's Statewide Summit. It was a phenomenal opportunity to see how funders change Florida through funding that takes going out on a limb. Risky giving is not a call to burn funds in effigy, watch the smoke rise, and smile as we say, "Well, that was quite the risk." Instead, it is a chance to truly demonstrate the trust we have built over time with our partner organizations. Debra Jacobs, CEO of The Patterson Foundation, often says, "Change happens at the speed of trust." This is entirely true. The more trust we can build with a partner, the more chances we have to take risks because we have journeyed alongside them for quite some time.

I recently heard someone flip this saying on its head. "Trust happens at the speed of change." This can also be true, and funders can build even more trust with partners when we are willing to change and evolve.

Risks are scary. Take, for instance, TPF's creation of Patriot Plaza. No private philanthropy had ever participated in a partnership with the government to create something so unique. One of the TPF Governing Board members told me a while back, "People thought we were crazy when we did that." But crazy, risky, insane, whatever adjective you feel is appropriate, led to creating one of the most iconic spaces in southwest Florida and a space that serves to honor veterans and their families around the country and the globe. Patriot Plaza was a massive risk. But the reward and gift it has become were worth it.

Another example of "risky behavior" is TPF's continuing to provide an uncapped, dollar-for-dollar match for the Giving Challenge hosted by the Community Foundation of Sarasota County. Since TPF doesn't grant money, the Giving Challenge allows organizations in the Suncoast to interact with TPF in new and innovative ways. Since the pandemic in 2020, the two Giving Challenges have raised over $35 million from the community's support, including more than $13 million in matching funds from The Patterson Foundation.

We have to be willing to take risks to watch amazing things unfold. The rewards we see are most often directly tied to the risks we take. Our communities can be all the more vibrant when we operate in the space of what is possible and are willing to step out in faith to create new realities.

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