Jeff Moster

I grew up in a very sheltered, homogenous community in a small town, Indiana. It wasn’t until I graduated from college that I started meeting people from urban center cities and neighborhoods they grew up in, which were very different than mine.

It was from the friendships I formed with these people that I learned of the cultural divides and systemic racism that had kept marginalized communities oppressed. It wasn’t until I met people from outside my bubble that my eyes were opened to the unfairness and disparity in how certain people are treated from day one, and it motivated me to want to try to do something about it as best I could.

The way you ask this question is perfect. Let’s start with the latter part of it, where you reference the identity of the city. By many standards, Chicago is one of, if not the most diverse, city in the country. We are dominated by large minority percentages of white, African American, and Hispanic residents. However, we are robustly complemented by smaller numbers of Asian, Middle Eastern, Jewish, Eastern European, and more recently immigrated (non slave trade) African Americans. Of course, this can’t do justice to all of the various unique backgrounds here, and in a way, that splendid diversity that is so impossible to succinctly describe is the essence of our town. 

What the Chicago Children’s Choir does is bring together youth from all of these diverse sectors and subsectors and, through the power of music, teach them life lessons. They sing Jewish songs, Muslim songs, African songs, Indian songs, modern American pop, and the list goes on and on. With every score the kids learn, the instructors teach these kids from different socioeconomic backgrounds about each other’s cultures, religions, and customs. They are taught love, understanding, education, and tolerance.

Importantly, they are literally bringing kids from different zip codes physically together to meet and befriend each other when they practice and perform these songs.  It provides a platform for interracial and intercultural exchange and education that helps blow up this evil called ignorance, which, as we know, is the main driver of prejudice.

Unfortunately, a lot of my experience with city outreach was driven by my engagement with the race relations committee, which was under the leadership of Randall Blakely, who, unfortunately, resigned from the club due to the ULCC’s unwillingness to make a stand against the many discriminatory actions of the current administration. 

Voter suppression and imprisonment of asylum-seeking and economic opportunity-seeking refugees were just a few things the subcommittee on race relations, through Randall’s leadership, asked this club to speak out against. Their lack of willingness to do so, particularly after he (President Trump) pardoned over 1500 people involved in the January 6 capital takeover (the vast majority convicted criminals), caused him to make a stand and resign. It’s quite sad because he’s one of the great leaders of this city when it comes to race relations. We lost a good one there. 

Now I can answer your question, but it’s through that committee that I can do so. Things I’ve learned are that we live in a large city that’s a combination of scores of micro cities. Not only are (predominantly white) Lakeview and (predominantly black) Austin different, but when we have an event that takes us to meet people from Austin or Roseland for example, you very quickly see that not all African-American subsectors of the city are created equal, as those neighborhoods have significantly more challenges than Woodlawn or Hyde Park. 

We’ve engaged with non-profit back-to-work and religious operators in South and Westside neighborhoods where people have been brought up in impossible conditions. Without the club’s programming, I never would have seen the work Chicago Cred is doing (off the streets / out of prison into the workforce training and assistance), I never would’ve had the opportunity to hand out turkeys on Thanksgiving in the many housing projects that we still have, despite Cabrini (Cabrini Green, a now-demolished public housing project) coming down. There’s a whole world out there that most of us don’t even know exists, and once you step in, you see that life isn’t fair. I often think, if I were born here, would I have been able to get myself out?

I think the best thing I did while at Springboard was implement what I call (and it still is called) a “grantee champion” program, where each nonprofit we serve has an individual from the Springboard Foundation assigned to be their champion. The champion for Springboard meets with the grantee to listen to them, advocate for them, understand what they need, etc, and then goes back to the Springboard foundation and sees if we can provide them resources to help them with their journey, whether they be monetary, educational, board development oriented, etc.

Frankly, yes, and not necessarily in a good way. I mentioned the sheltered, homogenous (white) community where I grew up. We weren’t taught overt racism using N-word references and things like that, but we were taught that you don’t go to certain parts of Indianapolis because “that’s where the Black people live”.

I can also remember a time as a little boy sitting with my grandpa, hearing on the radio about an automotive break-in/theft of a CB radio. My grandpa said, “I can tell you what color they were” (referencing the robber’s skin, of course) without any clue what really happened or who the perpetrators really were. Guilty until proven innocent, I guess. 

As I mentioned before, when I finally started meeting people of color and I listened to their stories, I juxtaposed that against my upbringing and how unfair it was to have been taught that all those people are the same and generally inherently bad It made me want to unwind the cycle for my kids and my community.

I think most nonprofit organizations suffer from the same kind of group dynamics that occur in corporate America and government. Specifically, I’m talking about the impossibility of getting dozens of different people‘s perspectives all on the same page and how leadership requires steadfast commitment to a true north while trying to build as much consensus as possible.

Some nonprofits have barriers to entry that are economic (minimum amounts people are required to pay to be a “member” of the organization) and thus inherently biased against building a robust (diverse) membership due to the plain fact that the high economic cost of entry may deter certain participants from joining in.

Frankly, I think it puts things in perspective. The reality is that on a day-to-day basis, I work with affluent investors and help them maximize their generational wealth transfer and investment returns. That’s about as cold and “non-societal benefit-oriented” as it gets. However, when things don’t go so well in the stock market and people lose a few percent from where they had been, I feel a little more grounded knowing that these are rich people problems, and that for every person that may feel dissatisfaction with their investment portfolio, thousands of people would trade places with them in a heartbeat for that problem.

I recently joined the board of Boxing Out Negativity. The organization operates in North Lawndale, a notoriously challenging community. Our program director, Derrick Brown, gets kids off the streets and into the boxing gym, but teaches them much more than boxing, conditioning, and strength training. The idea is that through peace circles, communication, and conflict resolution, we can give some of Chicago‘s youth an alternative to gang affiliation. My role there is treasurer, and we are working to enhance the breadth of our funding, which needs a lot of help from individual donations.

Fortunately, because I essentially have my own business, I have some amount of flexibility to do what I need to do from a time perspective to engage in my charitable work. Sure, I could choose to work an extra couple of hours a week instead of doing the community work and make a few dollars implicitly from that, but I’d rather give back.

This is a big one. Nonprofit organizations definitely need representation within their ranks that mirrors the communities they serve. I remember some of my earliest community service endeavors in Dallas, Texas, swooping into a high-risk community every Saturday as a mentor and trying to build a relationship with a troubled young Hispanic man. It didn’t work. I think he looked at me like some out-of-touch, white guy who probably meant well, but couldn’t even come close to relating. 

I think some organizations mean well, but end up being a club of wealthy white people that make each other feel good about what they’re doing without making much of a connection to the people they’re trying to help. Don’t get me wrong; the money they give helps, but by having diverse membership, their impact can be much stronger and more connected.

I think I have gone from being completely ignorant to what it’s like being a “have-not” in a disadvantaged community to being completely empathetic. It’s not until you go into these neighborhoods and meet the people, talk with them, look around and see the lack of opportunity, the propensity for gang violence, etc., that you realize just how impossible it is for the people born into those communities to simply lift themselves up by their boot straps. After all, you have to have boots to do so, right? 

Most people I run into with a lack of empathy live in very sheltered (mostly suburban or small-town bubble) communities. They’ve never once spent time in Lawndale or Austin, yet they are confident in their judgment of those citizens’ “lack of drive, laziness, and appetite for government assistance”.

It helps on two levels. As I mentioned before, I tend to serve in more finance and fundraising roles, which are very similar to the skills required in my wealth management career. Second, because I have the good fortune of having 25 years in the industry and have built a fairly sizable practice, I can afford to financially support organizations I believe in.

This is a tough one because the reality is that most nonprofits don’t have access to cash to invest. I think the biggest analogy might be diversification, not so much from an investment perspective, but from a diversity of funding perspective. You don’t have all your eggs in one basket when you invest, and you don’t have all your eggs in one basket for funding sources.

We spend most of our time putting things in perspective. Because we do a lot with risk management and hedging, we tend to underperform in markets that are up 15 or 20% in any given short-term period. However, when we go through what we just went through with the Trump tariff announcement, etc., we find that our clients tend to “lose” significantly less than the more risk asset-oriented sectors, and that’s the benefit of our approach.

Also, we spent a lot of time focusing on goal attainment versus making 9 1/2 versus 10 1/2% a year, if you can still accomplish your life goals on 9 1/2% and there’s a more assured way of getting there, most of our clients prefer that route and we remind them of that.