Recent events have compelled nonprofit organizations to change the way they get work done, how they deliver their services, and what they do to achieve a more just and equitable society. So, The Business of Giving has connected with those organizations that are doing this exceptionally well in a segment we call: The Paths Forward. Because there is more than just one way.

Denver: Today you’ll be meeting team members at Silicon Schools Fund. They fund the creation of new schools in the Bay Area that foster innovation and personalization to discover the next generation of schools in America.

At Silicon Schools relationships are all important and they’re often built in the most natural of ways such as driving in the car or having lunch together as Caitrin and Kelly explain.

CAITRIN: I think that being in person with each other, having shared experiences, putting a lot of miles on the car, debriefing a lot of meetings, eating at every taqueria near every school that we went to, was really a part of how we both got to know each other, and also really calibrated on what great work looked like, and what great schools looked like. And in particular, for me, when I was learning really from Brian, I had to go first. I had to put myself out there and say, “This is what I’ve saw. Is that what you saw?” And that’s how I built some of my own internal compass. And so, I think any chances to do things together, not just to talk about the work, but see the work and do the work, whatever that work is for someone, and for us, it’s the work of schools, has been really powerful.

KELLY: I think the other thing I really appreciate now and I’ll tell a little bit how I think this drives the work is the team eats lunch together. I cannot tell you as an outsider how foreign that is. And this weekend, one of the things I was thinking about coming back to work this week is how excited I was to eat lunch with them tomorrow when we’re in person together, and I think for me, like, sometimes we talk about work, but I think what it helps with is I get to know the values that our team has and what’s really important to them. And then later on, I’m able to leverage those in a really productive way. So, if I’m thinking about like a question I have or even like a strategy I want to suggest, I actually know what matters on a deep personal level to my team and then I can use those things to actually navigate workplace conversations later.

In a small organization it is so important that people enjoy spending time with their colleagues. Robin and Amy say that begins at the hiring process.

Rob: I mean, we talk, whenever we hire somebody, it’s almost like the first thing that we say when we hire them is no drama. And that’s like table stakes for like being part of this team. And clearly, there’s a lot of very talented people out there that could add. But if they’re going to bring a sense of drama, because that’s just some people like to, that’s something that we try to look for as we’re having conversations throughout the interview process.

AMY: And earlier question of how do we get such high-performing teammates that we all love to be together with? I think it goes back to the intentionality. We put so much emphasis and thought into the hiring process and the series of conversations to ensure that we have somebody that we love to spend time with, as Kelly said, having lunch with and sharing parenting advice with.

The forces that guide the organization are its culture, its mission and its North Star. Brian, Rob and Caitrin address the importance of these.

Brian: Culture is this thing that gets built that becomes bigger than any individual and actually becomes bigger than all the individuals and it becomes the perpetuating thing, which is why it’s so bloody hard to change culture and why it’s so important to get culture right at the beginning. And our team has these rituals, these shorthands that you’re hearing about today that just reinforce all of us bringing our best selves to work every day and all of us doing our best work for as many hours of a day that we can do it and then also wanting to be in a place that we’re happy.

Rob: And, I think the reason for that I think, like Brian said, how we were all beneficiaries of a foundation such as ours in the past and many of us have been in schools and worked deeply in schools in the past. Actually, we all have in one way or another. And therefore, it is so ingrained mission driven in us and this work is personal. Like, it’s part of not just like our organizational mission, but we’ve all decided, like, this is part of our life’s mission.

Caitrin: And for us, we’ve had a real North Star, which is how does the things we’re doing in this office and together translate to kids in schools? And we don’t just do things because we said that we would do them. We don’t just do them because other people are doing them, but we ask a lot of each other and ourselves, “Why are we doing this? And do we think that the thing we’re doing is going to benefit kids?” And if we can’t answer that question, I think we’re always clear that then we should wait to do something.

The organization goes by the adage that “Clear is Kind.” Caitrin and Brian reveal what is meant by that.

Caitrin: “You don’t talk about someone, you talk to someone. There’s no triangulation.” And so, I always think if I have something that I want to say that I’m feeling that I want to say to someone about someone else, I should be saying it to them. And whether it is feedback, whether it is a feeling of discomfort, so like, “Don’t talk about people, talk to people.” And then the second thing that we use sometimes is the idea of like flossing with folks that sometimes in relationships like sort of detritus builds up, and if you just let it linger that plaque grows and grows on your teeth and before you know it, the teeth aren’t looking so good.

And so even the shorthand of like, “Hey, can I floss with you?” Or, “Hey, can I talk about that interaction we had, like it didn’t feel great to me and I just want to name it and talk to you.” Because it can’t just be about talking about the good things. It has to be talking about the things that we’re uncomfortable and clearing it out so it doesn’t build. And so I think having some of that.

BRIAN: And then we have a shorthand, we say, we’ll tell you if your baby’s ugly, right? We love this baby. We’ve helped adopt it. But we’re also going to be direct and honest with you if there’s challenges that we see. And just to have a culture with our grantee partners and with our investors who we raise our money from of let’s be rigorous and let’s take the work extremely seriously.

While news is often good when measuring impact that is not always the case. Amy and Kelly speak to the organizations ability to face those realities when they occur.

AMY: Back to the other thread around measuring impact. I think it takes a team that has courage and willingness to face some of the bad data, if you will, are the brutal facts in order for us to continue to push ourselves to be better. And I truly believe our team really embodies those values to have the discipline to say, “What are the measures to let us know whether or not we’re on track or off track? And when we are off track, having that honest conversation of “what pivots do we need to make” as opposed “to continuing to live the rosy picture of we set this plan and we’re just going to track on this plan for the next 5 years because that’s what our business plan document says,” and I really do feel that we are living those values in order for us to make sure we are I’m using data to guide us and to give us progress indicators for doing what we set up to do.

KELLY: “No, this is the type of place you want to work,” because these are folks who are not just going to keep doing the same thing because they keep their jobs, but these are people who are going to actually question the work that they’re doing, question the impact that they’re having, and pivot and evolve if they have to. And to me, that feels like a cultural that’s honorable and ethical and 100 percent a place that I want to work.

What is the organization’s Secret Sauce? Brian maintains it’s their love of entrepreneurs, Caitrin speaks to everyone’s responsibility to build the culture, Amy is partial to their bias for action, Rob likes how they try things in small doses and Kelly chooses their ability to execute.

Brian: If Silicon Schools has one secret sauce, it’s that we love entrepreneurs, and we spend a lot of our time trying to find them. We call it shaking every tree, looking under every bush, which a lot of foundations don’t do. They sit back and they try to put paneled walls up and make it hard to get to them. If you want to do something big and bold in education, we want to meet you because that’s our goal, and we have to find each other.

CAITRIN: So, I think our secret sauce is based on two things. One, the deep belief that it’s possible to love your job, feel purpose filled, and adore coming to work with people that you work with. And two, that it’s all of our responsibilities to make sure that we are always building that culture and always making sure this is a place where we all can do that. And with that, I think you can build a tremendous amount because we all take joy in our work and we all feel ownership of our work

AMY: I think we all embody this bias for action and insisting on highest standards as a phenomenal funder, I think it’s easy to write the check and wire the money. But still hold the discipline to make sure the money that we’re giving is to the most effective organization and leaders. And that we play a role in holding that accountability so that the outcomes are of the highest standard

ROB: And I’d say the one other thing about that is that we will try little things before we actually create the final meal. So, we’ll taste a little bit of that. What is it like? What does it feel like to invest in this area? Or who are the experts that I can talk to over here about this? And then we can come back to the team and say, you know, I’ve decided we should not go in this direction. This is why. And at the end of the day, we now have this like beautifully plated meal.

KELLY: but for me, the secret sauce is around precise, intentional execution. And so it feels like there’s been a lot learned over the last decade, and there are some pretty clear processes and structures that exist. And what I’m the beneficiary of is just precise, intentional execution of what has been learned. And I see it in how we prepared for the board meeting. I see it in how we approve new grants. I, I just see it in how I’ve been coached to meet with prospective grantees, but that there’s a playbook and it’s not just a playbook that came out of Brian’s mind or Caitrin’s mind. It’s a playbook that’s evolved over years of real intentionality and so, that execution of it feels really powerful to me.

I want to thank all those who participated in this piece: Brian Greenberg, Caitrin Wright Kelly Garcia, Rob Schwartz and Amy Ng.

To learn more about Silicon Schools Fund go to their website at or visit and listen to my earlier interview with Brian Greenberg, the CEO of Silicon Schools Fund.

Denver Frederick, Host of The Business of Giving serves as a Trusted Advisor and Executive Coach to Nonprofit Leaders. His Book, The Business of Giving: New Best Practices for Nonprofit and Philanthropic Leaders in an Ever-Changing World, will be released later this year.Listen to more The Business of Giving episodes here. Subscribe to our podcast channel on Spotify to get notified of new episodes. You can also follow us on TwitterInstagram, and on Facebook. 

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