#345- Cinderella Nonprofit: How a Brooklyn Debate Coach Went Viral and Raised $1.3 Million in 48 Hours with DiCo - Nonprofit Lowdown

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[00:00]
Rhea Wong
Hey, you, It's Rhea Wong.
[00:02]
Diko
If you're listening to nonprofit Load on, I'm pretty sure that you'd love my weekly newsletter. Every Tuesday morning, you get updates on.
[00:09]
Rhea Wong
The newest podcast episodes.
[00:10]
Diko
And then interspersed, we have fun special invitations for newsletter subscribers only and fundraising inspo because I know what it feels like to be in the trenches alone. On top of that, you get cute dog photos. Best of all, it is free. So what are you waiting for? Head over to riawong.com now to sign up Foreign. Welcome to nonprofit Lowdown. I'm your host, Rhea Wong.
[00:38]
Rhea Wong
Hey, podcast listeners. Your girl Rhea coming to you once again with nonprofit Lowdown. I am super excited because today I am talking with my friend Dego. Deko is the executive director of the Brooklyn Debate League. And today Diko and I are going to talk all about really what is their Cinderella story is how I think about it. This is not your typical trajectory of a nonprofit. And I don't know, I just feel like a lot of luck. I don't know, someone's looking out for you and the universe. Things have. Which is not to say you haven't worked for it, but you've had a lot of lucky breaks. And I want to talk about what that's been like for you because I think sometimes we think about the good stuff, right? We just think, oh, gosh, if Mackenzie Scott just dropped a million dollars at my lap, I'd be super. I'd be set. But I think the other side of the coin, which we don't talk about, is what happens when you do get unexpected success and how do you prepare to scale up really quickly. Diego, welcome to the show.
[01:36]
Diego
Thanks so much, Rhea. Happy to be here.
[01:38]
Rhea Wong
All right, let's get into it. So before we get into all of the amazing things that happened to you along the way, bring me back. Bring me back to being a high school teacher in Brooklyn teaching a bunch of kids about debate.
[01:51]
Diego
Yeah, so I started my career in Harlem, actually, and I was there for four years, and I was teaching the first year of teaching. I also started coaching a debate team. Did there for four years, and then I went to Brooklyn, did that for eight years. And at both schools, they didn't have debate teams before I got there. And it really mattered to me that I built debate because debate was the thing that changed my life when I was in high school. In fact, three out of four of the siblings in my family did speech and debate in high school, and it changed all of our lives. So, like, I just personally experienced, like, this was an activity that changes kids trajectories. And as a teacher, I saw that impact immediately on my students. And kids started getting good. Kids work hard, they were motivated, they, within a couple of years started getting very good. And by 2016, 2017, I qualified our first kids to the national championship. And when my kids came back from nationals, they looked at me and they were like, where was everybody else? Because what happened at Nationals was they started noticing that they were some of the only kids from low income public schools competing on that level. And there were thousands of kids who do speech and debate competitively in this country every year. But I can count on one hand the number of schools that are low income, Title 1 schools that have competitive debate teams on that level. I was very lucky and blessed that I got to work at one of them and worked with brilliant kids. But when we came back that year from nationals, a couple of us, the kids and I, like, we and the alumni, we got together and we were like, all right, so what can we do about it? And we started partnering with some local private schools and parochial schools that had established programs. And they, they were all for, how do we make this activity more equitable? And we built the Brooklyn Debate League. This was in 2017. I was still a full time teacher, I was still a full time coach. This was a side project. This was a thing that I did. I had no idea about nonprofits, and it wasn't even a nonprofit for a couple of years. It was just a thing I on Fridays. And like, we opened up our high school after school and we welcomed welcome local middle school kids who didn't have debate teams. And my kids ran debate for them. So they taught them, they coached them, they ran tournaments, they judged the tournaments, they gave them feedback, we ordered a pizza, we gave them little trophies. We called it a day. Like, it was great. And then we did that for a couple years. And then, of course, everything changed in 2020 with the pandemic. And at that point, I had left the school, went on a side journey, like a little side quest to go to rabbinical school for a semester. I thought that was another calling, but I kind of boomeranged right back to this calling. But anyway, so like, during 2020, I'm not teaching anymore. The kids are. All the kids are missing out on so much, especially here in New York. And so we moved this whole thing online. And I was shocked to find out that there was so much eagerness for it. The kids were desperate for a chance to connect with other kids.
[04:35]
Rhea Wong
And.
[04:35]
Diego
And we had weekly Classes online. We had weekly tournaments online. We had a week, a summer camp for six weeks online. It was just something fun to do where the kids were like, oh, yeah, I haven't lost everything. I still have a way to do this thing online. And we did that for a couple years.
[04:50]
Rhea Wong
I just want to pause there for a second because I don't know if you. Have you seen that show Adolescence on Netflix?
[04:57]
Diego
I have, yes.
[04:58]
Rhea Wong
Yeah. So there's a lot that was very thought provoking. But one of the things that I think the police officer says is I think a kid is okay if they feel like they're good at one thing.
[05:09]
Diego
Yes.
[05:10]
Rhea Wong
And it seems to me that you were able to help a lot of these kids unlock a thing that they were really good at. So if you could explain, because you and I have talked about the power of speech and debate and the fact that Oprah was a speech and debate person. What is it that you think is special about speech and debate that really helps kids unlock a sense of self?
[05:28]
Diego
Yeah. So when we talk about speech and debate, I should also just say what it is because a lot of people don't know if you ever watch the Olympics or you think about, like, track field, Right. It's not one event that there's like a dozen events and there's like a sprint and then there's a half marathon, there's a marathon, there's a relay race. There's all these different parts. Right. And it's. We call it track and field, but it's got all these different categories. Competitive speech and debate is the same, so we call it speech and debate, but it's got all these different categories. And some of them are purely public speaking. Some of them, you memorize someone else's speech. Think TED talks or commencement speeches. Some of them you write your own speech. And like you, you make your own TED Talk. And like that, you give the speech every time. 10 minute speech, you memorize it, you give it all year. Some of them, you don't know what the topic's going to be until you get there. And then in 30 minutes, you write a speech and then you give the speech and it's about something in current events and you don't know what it's going to be. And some of them are less about public speaking, more about performing, where you get a scene from a play and you cut it and you act it out by yourself or with a partner. Maybe there, there's some categories where you are reading prose and poetry. Like there's all this speaking and acting stuff. And then that's just the speech side. There's the debate side where you are arguing with another person. Maybe it's one on one, maybe it's two on two. Maybe it's a room of 15 kids. There's different categories there too. So why is this helpful to kids and why is this uniquely changing kids trajectories? When you think about moments in your life that were high stakes moments, usually, not always, but usually they involve talking to someone else. And usually there's some sort of dynamic at play that makes it intimidating. Maybe it's a power differential. Maybe you're interviewing for a job and you're talking to a boss, right? Maybe it's a class differential. Like I was a first gen kid and I remember being in college feeling intimidated that all of the people sitting in the seminar table around me like had parents. Some of them, their parents were college professors and my parents didn't go to college. Right. So maybe it's a class thing, maybe it's a race thing. I'm white. This is something I haven't experienced because of my privilege. But many of the students, most of the students that I have teach, I have taught. This is something that they've experienced as people of color living in this country. But for whatever reason, frequently when you are having a conversation that's high stakes with someone, there's often something that makes it scary. And that's on top of the fact that just in general public speaking is the number one fear of Americans over dying. That's true. They've done studies on this. So there's a baseline. Everyone is terrified of this. And then there's all the other identity based things that come into play, to say nothing of the ideological things that come into play. It's scary to talk to someone that doesn't agree with you. And especially right now, I mean, we're seeing this in our country like it is. Many people would rather just cancel someone than debate them because it's, it's scary. And look, this is a conversation we're not going to have right now. But I will say it doesn't get us anywhere when we are just when we are not engaging constructively. If we're going to move forward, it's because we are communicating, we are collaborating, we're compromising. You don't get anywhere but being like, I'm in my righteous fear and you're in your righteous fear. Right? So anyway, for all those reasons, when we think about the power of being able to walk into any space regardless of who is in that room and how they might be different from you and how their lived experiences might be different than yours, how their ideas might be different or yours walk into any room and say, look, here is what I want to say and then here's the real clincher to listen to what they say back. Like that is power. You can't buy that. That and private schools know this. Like there is a reason why half of the people sitting on the Supreme Court right now did speech and debate in high school. There is a reason why almost every private school in New York City and around the country has a competitive team. This is a skill that it changes kids lives. It gives them a power to be in those spaces and to make the decisions and to be influencers and for people to listen to them. And unfortunately, maybe it's not surprising that the communities that have been historically silenced and suppressed are also continually being silenced and suppressed in this way. Because many of those schools, we're talking about low income schools, we're talking about public schools, do not have the bandwidth, don't have the institutional capacity, don't have the resources. Like there's. This costs a lot of money to teach kids how to stand up and, and it's. I can't think of a skill that's more important, especially right now, like thinking about these teenagers as the folks that will be voting, as the folks who are taking over the leadership in our country. Like we as a society, like when we're trying to defend democracy. This is democracy. This is what it was in ancient times. This is what they taught kids was rhetoric and speech and debate. This was like the pinnacle of your education. Where is it right now? It's not happening in our K to 12 curriculum. And so we have to supplement it. And the way that we supplement it is with competitive speech and debate.
[10:40]
Rhea Wong
Diko, I am a believer. That was awesome. And I have so many thoughts here. I'm thinking about the fact that democracy dies in darkness. I think exactly to your point around how do we help people elevate their voice to say that they're not okay with what's happening in this country right now, to say that we care about things like due process and voting and rights. And this brings up for me, I hope I won't disturb, but it's a quote from Rumi. Beyond doing and wrongdoing, there's a field.
[11:11]
Diko
I'll meet you there.
[11:13]
Rhea Wong
And I think the capacity to listen and to listen without defensiveness and jumping in. And you're right. And I, and you know, you're wrong and I'm right, and whatever is the core of the fabric of our society. And when that is torn asunder, what is left?
[11:33]
Diego
This is how we invest in that, particularly in communities that have been systemically silenced. Like we. What do. How do you confront silence? You lift up voices.
[11:43]
Rhea Wong
Okay, Diko, we're gonna have a side conversation about how we're gonna scale this out and start the movement across the world. But before we do that, let's talk about. So here you are doing amazing work with a pretty small group of kids who were in your classroom, or maybe not in your classroom, online, and then something happened which kind of. It was a rocket ship shot in the arm. What happened?
[12:08]
Diego
Okay, so remember how I said before I was a teacher, I was not a non profit director. I had no experience in building non profits and running non profits, working for none of that. In May of 2022, I was a full time history teacher, still running Brooklyn Debate League online for fun. At this point, like, I'm paying my alumni who are now. The kids that helped me started are now in college. I'm paying them every week to come and run it to be the teachers online, like from their college dorms. Paying them for this out of pocket, by the way, because if this is not a. We're not charging anybody for this. We're really trying to support low income communities. One of my alumni, my first ever students, his name is Jonathan Conyers. I taught him in 2009 at Frederick Douglass Academy in Harlem. He's helped me pay for this. So at this point, he had just graduated from college and he's got a right out of the college. He, he was a Neo. He is a neonatal respiratory therapist at NYU. And do the math on this, right? This is 2019. 2020. He's the guy that ran the ventilators during COVID Okay, guys, a 20 year old kid. All right. Anyway, he hears about what I'm doing and we've stayed in touch this whole time since. Since his high school graduation or since high school? For more on his story, you should read his book I Wasn't Supposed to Be here. It's a memoir that talks about how debate changed his life. Anyway, we're in touch. He's helped me pay for this. So he and I are writing checks every month, like paying the alumni. And eventually I'm like, john, like, I don't know. I can't. What are we. What's the plan here? He's got three kids of his own and he's. I don't know, Dico, what's the plan? And he goes, listen, I got an idea. And when my students tell me they have ideas, I listen because they're usually right. And John ends up telling the story of his life and how debate transformed his path to the Instagram platform. Humans of New York. And Humans of New York interviews John and interviews me, and we end up. Brandon Sanson, who runs Humans of New York, writes, I think at that point the longest post he'd ever like, long story, long form post, has ever written about John's life.
[14:07]
Rhea Wong
Wait, and did John know him before or was it a cold pitch?
[14:10]
Diego
Yeah, John cold pitched him. Gee, and I wonder where he got the confidence to reach out to folks. And just really though, and he attributes this. He came to me really special and brilliant, but he just cold pitched it. And Brandon at that point, I don't think had even responded to a cold pitch before. Like, Brandon's whole limo was like going around the streets of New York and just like interviewing, interviewing random people. Brandon's Wait, what is this story? Tell me more. This is a kid that he was in homeless shelters. His family was suffering from substance abuse problems. Like, he had been through so much in his life and he joined debate team, in his words, to keep himself off the streets and so to pick a new path. And it worked. It got a full scholarship to college and then was saving people on the front lines of the pandemic in 2020. So Brandon's this story is amazing. Tell me about this. And he writes this post that goes absolutely viral. And John the whole time is telling me, dico, this, it's going to come. It's going to be big. Get ready. And I'm like, yeah, I got lesson plans to write, dude. But I don't know. I. Please, I know. And he's, you know, it's coming, it's coming. And I was like, sure he was right. Because on May 9, 2022, this story goes live and millions of people read it and thousands of them donate to the GoFundMe that was attached at the end of the story. So that within 48 hours of this story being posted, the GoFundMe for the Brooklyn Debate League that we had posted at the top of the end of the story there had raised $1.3 million, which is, suffice it to say, more money than I have ever seen in my life as a public school teacher in New York City, more money than John's ever seen in his life. And the two of us at that moment were like, okay, we got to do this thing, and we got to do it right now. So I finished off the school year and I left the classroom, and. And John talked to nyu, and he's part time at the hospital, but now is like part time with us at Brooklyn Debate League. We started that August with summer camp with no experience between us with nonprofits, with no. I knew how to write lesson plans, I knew how to build debate teams. I did not know how to run a nonprofit. But we had $1.3 million in the bank and 30,000 people on our mailing list who were in our corner. And that's how this whole game started.
[16:19]
Rhea Wong
Wow. So many things here. Okay, so now here we are. We're may the time that we're taping this May 1, 2025. So it's been all of three years. Three years in the seat full time. And I think you and I met pretty early on in your nonprofit life. And I'm just curious because I think when we talk about nonprofits, we talk a lot about the structural things like the staffing and the this. And how do you do a fundraiser. We don't often talk about the internal shifts that I think we need to make within ourselves to be the leaders, to see ourselves as leaders, to have the confidence to run this thing. Especially in your case, because it was just like meteoric. So it wasn't incremental. You didn't get to grow into it. It was like public school teacher one day, head of a multimillion dollar nonprofit the next. So I'm curious if you could think back, what are the internal shifts that you felt like you had to make in order to step into this new world?
[17:18]
Diego
Yeah, it was really hard, actually. The only thing I'd ever done at that point was teach, and suddenly that wasn't my job anymore. I think one of the biggest shifts I had to make was to. And it's still ongoing, honestly, but it was to figure out what did success look like for me, and then how do I chase it? When I was a first year teacher, that was its own path, right? It was like, all right, who do I have to talk to? Who are the mentor teachers I need to sit and observe, and how do I get coaching and how do I learn how to do this? And also how do I make changes every single day to make today a little bit better than yesterday? And my first year of teaching was awful. But most people. It's really hard to be a first year teacher. My second year of teaching was a lot better. My third year of Teaching was amazing, and I got on this curve that felt like the learning curve felt so good in teaching. And then when we started Brooklyn Debate League, I was like, and I'm back to the beginning, because here I am again. And I need to go find the mentors, and I need to figure out, like, who are the people that are doing this? I need to learn from. I need to figure out how to be. How do I train, who can train me? And I need to every day figure out, all right, how can I make this process tomorrow a little better than it was today? And my first year in the job, it was really hard, and I made a ton of mistakes, but by the end of it, same thing with my first year of teaching, I was like, all right, how's year two going to be different? And how's your three going to be different? And I. It has been just like with learning how to be a teacher, the learning curve has been exponential. And I feel right now so grateful for all of the training, all of the mentors, all of the people in my network that I connected to, because I look back and I'm like, I was a fish out of water. Like, I was. I was. We had all this money in the bank, and I had no plan and no idea how to do it. And the reason why it's working is because I got a lot of help.
[19:08]
Rhea Wong
Yeah. I think there's so many amazing things about you, but I think one of the things that, to me, suggests that you are going to be a success is you are not afraid to ask for help. And I think sometimes, and look, myself included, I think I. There were points in my career I should have asked for help, and I didn't. I think what really differentiates the people who are going to be on the trajectory are the ones who are willing to ask for the help, willing to invest in the help. I know you worked. We worked together. I was coaching with you. You were also coaching with Brooke, who is a perennial fan favorite on this podcast. And so when I look at the things that you've done, which there are many brilliant things that you've done, I think you looking ahead at who's done this before, who can teach me what is ahead? Because, sure, we can all learn by doing, but wouldn't it be easier if you can get the CliffsNotes from someone? Yeah.
[20:00]
Diego
I mean that the first months that I was on this new job, my whole goal was talk to as many EDs in New York City that are educational, aligned as I could. And I talked. And for every single One. I was like, okay, who else should I talk to? I was like, okay, who helped you? And like, that is how I found you. That is how I found Brooke. That is how I have the EGF accelerator program that I did. Like, all the programs, all the mentors. It's because I. I just cold emailed folks and I was like, hey, I'm a new ed. Do you have any. Can I talk to you for 10 minutes just to pick your brain? And I would say I probably made talk to 40 people within my first two months on the job. One of those phone calls didn't go well, and the person was like, no, I don't got time for you. The other everybody else was like, yeah, I'd love to talk to you. All these people helped me and I'd love to help you. And I'm like, okay, this is a community. I just got to reach out. And people are really eager to help and to support each other.
[20:51]
Rhea Wong
I have to say, this is what's kept me in this industry, in the sector for 20 years. It's really good hearted, generous people who want to do the right thing. And sure, of course, every once in a while, you will find that one person you're. But people generally don't get into the nonprofit field because they're selfish, awful people.
[21:11]
Diego
Yeah. This is not like a cutthroat. Like, everybody wins if we are successful. It's. Yeah, it's been really helpful getting into the community.
[21:20]
Rhea Wong
Awesome. Okay. There's so many other things to go here. The thing about you, Diko, that is actually quite incredible is you have this incredible ability to connect with people. I don't know, it's your personality, it's your vibe. People just really want to help you. People are really drawn to you. And so you've had. I don't know if I'm allowed to say, but, like, you've had some very impressive folks in your corner. And when I talk to you, you're like, oh, I know this person. I know this. But I'm like, wait, what? Like, you have this Rolodex that I. Most people would give their left kidney for maybe both their right and their left kidney. So talk to me about how you built this incredible network as starting, as you say, like a public school teacher who didn't come from this family who could make phone calls, didn't have a trust fund, didn't have, you know, all the things that some folks do have. I don't know. Did that question make sense?
[22:12]
Diego
It did, and it's a good question. And it's one that I think about a lot. So the Rolodex that we're talking about here, there's everybody on there from celebrities. John and I were invited on the Kelly Clarkson show. And I was like, I genuinely. I live under such a rock that when her producer called me, I had to Google who Kelly Clarkson was because I was like, I think I've heard of you, but I'm not sure that's true. I have now since learned about her. Love her, Fantastic. She was a lovely person to meet.
[22:35]
Rhea Wong
Great.
[22:36]
Diego
And then Malcolm Gladwell cold emailed me a couple years ago and was like, hey, I lost the debate recently. I'd love to know why. Do you think you could tell me? And I was like, sure. Okay.
[22:45]
Rhea Wong
Like, Malcolm, cool. Call me.
[22:48]
Diego
There have been some, like, real folks. I cannot take credit for that. Just heard about us and reached out to us, and that's great. But I think most of the people in my corner that are folks with varying degrees of networks and wealth and support, like, they're folks I have met over the years. And, like, the reason why it's worked is because I try to be nice to people. And that sounds really, like, silly and cliche, but. But that's it, right? So here's an example. At the regular tournament, just like a Saturday tournament, on one random day in October three years ago, I was sitting in the Judges Lounge with 150 other people and these two women were next to me and they were like, oh, I've never judged online before. Do you think you can? Can you? Do you know how to do this? And I was like, yeah, sure, no problem. Let me show you. And I sit with them for a couple minutes and I show them how to do it and whatever. And then I find out, like, one of them started her own nonprofit 20 years ago. And it's. It's huge. It's national now. It's amazing. And she was like, oh, wait, what do you do? Oh, interesting. And like, we just connected where she's a huge supporter of BDL now and, like, we are in touch and it's great. The other one, her kids, both of her kids did speech and debate. And she became a supporter that day and is still a pretty substantial support. And I didn't reach out to them because they were potential donors. They just needed help. And I was like, hey, sure, no problem. And I was hanging out in a space where I know people care about this thing because it's a debate tournament, right? And what I do is debate. And that's not why I was there. I was there because my kids were there. But while I'm there, might as well be nice to people. You're not. You might as well help people when they ask. Like, you have no idea where relationships are going to lead, but everything is really grounded on relationships. Like, that's where this starts. And I really learned this not as a nonprofit director, but as a teacher. Like, kids, you can have the best lesson plan in the world. It's not going to land if the kids don't trust you. And you have to give kids a reason to trust you. Especially I'm a white teacher showing up, like, in mostly black and brown spaces. Like, they got lots of reasons to not trust me. Lots. Like, I have to earn their trust. I can't take that for granted. So I would try to be kind to them. I would try to make my class fun. I would make sure that they knew I cared about them. Like, I would go an extra mile to. To lift them up and to support them and to celebrate them. So that by the time that we were doing Latin class or we were going to debate tournaments at Harvard, or we were doing things that were intense, the kids were invested and they were like, oh, yeah, I trust you. Like, I know you care about me. We got it. And so this is something I've been doing since I was teaching. And I just think it's been really. It's followed me. Like, it's one of the things I've. And I try to teach my students. It's one of the things I've learned in my life that's be kind, be generous. Like, just be generous with your time. I don't have a lot of money to give. I'm a public. I was a public school teacher and now a nonprofit director. But, like, I've got time and I've got. It doesn't cost anything to be kind. And it comes back.
[25:38]
Rhea Wong
Yeah, Yeah, I love that. Okay, two more questions because we could talk forever. So now that you're three years in, you've had tremendous success. And I don't think this is confidential, but there, there's some big things in the works. A documentary, possibly a film like this. It again. A Cinderella story. So what now? Like, where are you today? Three years into it, what are you thinking about in terms of your fundraising? How are you thinking about growing your organization? What's the staffing structure? What does it look like today that is different than it looked like three years ago, which I guess it was non existent three years ago.
[26:16]
Diego
So what it Feels like today is. It feels like exactly my third year of ed is exactly what it felt like my third year of teaching. Like, people talk to me from day one of grad school and Teach for America Institute and all that stuff. They're like, okay, here's what backwards planning means and here's how you write a lesson and a unit plan or whatever. But like, it didn't sink in because I wasn't ready to learn it until suddenly it was like, oh my God, I see all the pieces of the puzzle and how they fit together. This is what I need to do. And once you do works. So from day one of being an ed, people have talked to me about like, all right, how do you build donor pipelines? Like, how do you work on your marketing and your newsletters? And how do you build relationships with major donors? And how are you managing a budget that's like, reasonable? And like, I knew all the pieces like, but like, I didn't have the capacity yet to put them all together. And suddenly the pieces starting to fall into place and I'm like, oh, wait a second, I know what my job is now and I know what success looks like and I know how to set myself goals. And like, I know, like I've known these things cognitively for three years, but suddenly I like, know it viscerally and I'm like, okay, I actually like this job now because in the beginning I missed teaching. It was all I ever knew. And like, I knew I felt successful. And I'm like, wait a second, now I know what it feels like to be successful here too. I was just saying to my girlfriend this morning, I was like, listen, babe, I know the last couple years or months or whatever, I've been really present since we started dating and whatever, but just so you know, this job, we're like about to take off. So you got to forgive me, be a little lenient because I'm about to dive in a whole different way. And I'm excited about it. Like, I'm not. It's great. It's just, I didn't know how to do that. I'm just starting to figure it out and I'm like, wait, okay, this is how my newsletter plan, my marketing plan, my LinkedIn plan, my donor pipelines. Like, my, Like, I'm seeing how the pieces are going to connect and the impact of that is like, I've got a budget next year, which is the most accurate budget I've had so far. I can say to my board confidently, next month, guys, here's exactly what we're going to raise, and here's how we're going to raise it. And here's exactly what it's going to cost. And here's how I know what it's going to cost, because, like, here's all the drivers and the aggregate costs that I've been compiling for the last three years. I got it. And then once I got that and I'm, like, on solid footing, I'm like, all right, like, then it's time to look forward. I couldn't really do the five or the ten year plans that you broke. Everybody, you're not wrong to tell me how to do it, but I couldn't do it yet until I'm on solid footing. And now I'm there. So now I have the room I need to start thinking, cool, where do I want to be in five years? Where do I be in 10 years? And what do I have to do differently next year to get there?
[28:53]
Rhea Wong
Yeah. Yeah. I just think about when you're learning how to ride a bike, you're like, I see the Tour de France. I understand how that happens. But I am still, like, wobbling on this bike, so I need to figure that out first. I feel like you're out of the wobble. And now it's okay, let's talk about the Tour de France.
[29:10]
Diego
Yeah. Out of the wobble. That's my motto for this year. Out of the wobble. That's it.
[29:14]
Rhea Wong
Yeah, yeah. Okay. I got it.
[29:16]
Diego
I'm gonna make. I'm gonna.
[29:17]
Rhea Wong
For folks out here listening, because you and I have known each other for a couple years now. It's been such a delight seeing your growth, seeing you change, seeing you think about fundraising differently. Can you talk a little bit about what that trajectory has been like for you? In particular, what it was like to work for me? Because folks listen to this podcast who might be considering applying to work with me. So if you could just give us a sense of what is it like to work with me.
[29:44]
Diego
Yeah, I would be delighted. I met you, Rhea, at the. You were a guest speaker at the EGF accelerator. And this is another example of how you said earlier, like, how do you expand your Rolodex? I liked your presentation, so I emailed you afterwards and I was just like, hey, thank you. I thought you had a great presentation. I'd love. I just introduced myself and you were like, oh, really? Here's my podcast if you're interested in my course. Like, here are some things I'm offering. I'm like, all right, cool. So we Started working together, I think you said, two years ago. And I took your course. I know you've changed the name of it. What is it called now? Big. Is it Big Ask Big Ass Gifts? Yeah, Big Ass Gifts. Love it. So I took that course, and again, at the time, I was in a place where I was just learning, and I don't think I was really able to implement all of it yet. But what I did get out of that course was like, one, the foundations that. Now a year later, I'm like, ah, yeah, I know what to do, because I learned this in Ria's course. And two, I got access to you and your network, which has been amazing. So since that course, there was like, another mini course that you connected me to that somebody, like, was looking to get a core group of folks together to talk about this new way to raise or to build relationships with major donors. And what I learned in that changed the whole game for me. Like, I've been playing with that all year. And like, now when I have a prospective major donor that has expressed a lot of interest and has said things to me that, like, they. They are basically saying, I am looking for my people. I think you are my people. What is our next step? Three years ago, I would have been like, I don't know. Like, in fact, I was like, I don't know when people ask me that question. Three years ago, I didn't have a plan. Now I know exactly what my plan is. And it's because of folks, the things that I learned in your class and folks that I met through your network. And it makes me feel so much more confident in doing my job as an ed. And I didn't know when I started this, a thing about fundraising, right? I was. I knew a lot about debating and a lot about coaching debate. I didn't know a thing about fundraising. But everything I know now is a lot of. It's because of you personally and people you've introduced me to, and also from trainings, like, from Brooke and other folks. But, like, working with you, it changed the game for me. And I will also just say that if you are someone that's listening to this and you're like, yeah, but I don't know if I have money to spare to pay for courses right now or to pay for consultants right now. I didn't know if I did either. Despite the $1.3 million that we raised, we gave a lot of it away immediately because I did not know how to do my job right away. And we were just, like, giving Away programming for free. So I was worri about money and I was like, yeah, I don't know, it's a lot of money, but sometimes you have to spend money to make money. And I have zero regrets about investing in my professional development, particularly around fundraising. That is, that is my primary job in this role is to make sure that we stay afloat. And in order to do that, I needed to develop myself with fundraising and you helped me do that.
[32:38]
Rhea Wong
Oh, thank you so much, Dico. All right, let me just ask one last question because I'm very nosy. How much do you think that you've raised as a result of our work together? If you had to guess?
[32:47]
Diego
Oh my gosh, I don't even know how to answer that question because it's so baked into everything that we're doing. I will say this though. I was just looking at these results, the budgets last night because I was doing a grant. I was like, oh damn, we raised twice as much this year as last year. I wasn't even tracking that like from individual donors. And that's like in the margins of like a hundred K. Like I think the first year we raised like 150K and this year we raised 250K. And I was like, wait, what we did? And like, it's like all of that is what's baked into that are moves that I made that were different this year that I wouldn't have thought to make if I hadn't learned it from folks like you.
[33:25]
Rhea Wong
Diko, I'm so pleased. And I think you're right at the beginning. The way that I see you rising is just, it's like a. I keep saying a meteor, but buckle up. It's going to be an exciting ride, friend.
[33:38]
Diego
Yeah, I can't wait.
[33:40]
Rhea Wong
So, Dico, thank you so much. It's been so fun. And of course I'm always here for you if you need anything. By the way, we should hang out and irl.
[33:49]
Diego
Yes, we love that.
[33:50]
Rhea Wong
All right, Dico, thank you so much. Good luck with you, Good luck with everything. And.
[33:57]
Diko
Hey, fundraisers looking to nail those big fundraising asks, Check out my Big ask giftprogram@riawong.com bag. Say goodbye to uncertainty and hello to confidence with my program. Get expert strategies and personalized support to secure those game changing donations. Don't let fear hold you back. Join me and take your fundraising to new heights. We're enrolling now@riawong.com bag. That's riawong.com bag. So if you like big asks and you cannot lie. I'll see you in the program.

Summary5 min read

Podcast Summary: Nonprofit Lowdown #345 - Cinderella Nonprofit: How a Brooklyn Debate Coach Went Viral and Raised $1.3 Million in 48 Hours with DiCo

Host: Rhea Wong
Guest: Diego (Diko) [Assumed Name from Transcript]
Release Date: July 7, 2025

Introduction

In episode #345 of Nonprofit Lowdown, host Rhea Wong delves into the inspiring journey of Diego (Diko), the Executive Director of the Brooklyn Debate League (BDL). This episode, titled "Cinderella Nonprofit: How a Brooklyn Debate Coach Went Viral and Raised $1.3 Million in 48 Hours with DiCo," explores Diego's remarkable transition from a high school debate coach to leading a multimillion-dollar nonprofit almost overnight.

From Teaching to Founding Brooklyn Debate League

Diego begins by recounting his early career as a high school teacher in Harlem and later in Brooklyn, where he introduced and built debate teams from scratch at both schools. He emphasizes the transformative power of debate, not just academically but personally, for himself and his students.

Diego [01:51]: "Three out of four of the siblings in my family did speech and debate in high school, and it changed all of our lives."

Under his leadership, the debate teams quickly excelled, with students qualifying for national championships by 2016-2017. The success highlighted the scarcity of competitive debate programs in low-income, Title 1 schools.

Diego [03:50]: "We were some of the only kids from low income public schools competing on that level."

In response, Diego and his team partnered with local private and parochial schools to make debate more equitable, leading to the formation of BDL in 2017. Initially a side project, BDL thrived by offering after-school programs, coaching, and hosting tournaments for middle school students.

Navigating the Pandemic and Moving Online

The COVID-19 pandemic in 2020 marked a significant turning point. With schools closed, Diego transitioned BDL's activities online, discovering a heightened demand for connection and engagement among students.

Diego [04:34]: "The kids were desperate for a chance to connect with other kids."

BDL continued to offer weekly online classes, tournaments, and a virtual summer camp, maintaining engagement and support for students during challenging times.

The Viral Moment: Raising $1.3 Million in 48 Hours

A pivotal moment came when Diego's former student, Jonathan Conyers, featured his story on Humans of New York, showcasing how debate had transformed his life from homelessness to saving lives as a neonatal respiratory therapist during the pandemic.

Diego [12:08]: "Within 48 hours of this story being posted, the GoFundMe for the Brooklyn Debate League ... had raised $1.3 million."

This unexpected surge in funding enabled Diego to transition from a part-time nonprofit leader to dedicating himself full-time to BDL. The influx of funds also expanded BDL's mailing list to 30,000 supporters, laying the foundation for rapid growth.

Internal Shifts: From Teacher to Nonprofit Leader

Transitioning to a nonprofit leader required significant personal and professional growth. Diego discusses the internal shifts necessary to embrace leadership, such as redefining success and developing fundraising strategies.

Diego [17:18]: "I had to figure out what did success look like for me, and then how do I chase it?"

He highlights the importance of continuous learning, mentorship, and the willingness to make daily improvements. Reflecting on his initial challenges, Diego credits his network and the support from mentors as crucial factors in his successful transition.

The Power of Networking and Community

A recurring theme is the value of building and nurturing a strong network. Diego attributes much of his success to his ability to connect genuinely with others and the generosity within the nonprofit community.

Diego [22:35]: "Just be kind to people. You can't take that for granted. So I would try to be nice to people."

His approach involves offering help without immediate expectations, leading to meaningful connections and support from unexpected quarters, including celebrities like Malcolm Gladwell and appearances on shows like Kelly Clarkson's.

Working with Rhea Wong: A Catalyst for Growth

Diego shares his experience collaborating with Rhea Wong, attributing significant portions of his fundraising success and organizational growth to her guidance and programs.

Diego [29:43]: "Everything I know now is a lot of it's because of you personally and people you've introduced me to, and also from trainings."

Participating in Rhea's Big Ask Big Ass Gifts program and leveraging her network empowered Diego to develop effective fundraising strategies, resulting in a substantial increase in donations—from $150K in the first year to $250K in the subsequent year.

Looking Ahead: Scaling and Future Plans

Now in his third year leading BDL, Diego feels confident and ready to expand the organization's impact further. With robust budgeting, clear strategic planning, and a solid foundation, he is poised to embark on long-term growth plans, including potential documentaries and broader initiatives to democratize access to debate education.

Diego [28:53]: "I'm seeing how the pieces are going to connect and the impact of that is like, I've got a budget next year, which is the most accurate budget I've had so far."

Conclusion

Diego's story is a testament to the power of passion, resilience, and the supportive nonprofit community. From building debate teams in under-resourced schools to leading a viral fundraising campaign, his journey embodies a modern Cinderella story in the nonprofit sector. Through strategic networking, continuous personal development, and unwavering dedication, Diego has transformed Brooklyn Debate League into a beacon of hope and empowerment for countless students.

Notable Quotes:

Rhea Wong [05:08]: "I think a kid is okay if they feel like they're good at one thing."
Diego [10:39]: "Once you are having a conversation that's high stakes ... that is on top of the fact that just in general public speaking is the number one fear of Americans over dying."
Rhea Wong [19:07]: "You are not afraid to ask for help..."
Diego [25:38]: "It doesn't cost anything to be kind. And it comes back."
Diego [29:17]: "Out of the wobble. That's it."

This episode not only highlights Diego's extraordinary achievements but also serves as an inspiration for nonprofit professionals aiming to navigate unexpected success and scale their organizations effectively.

Loading summary

Transcript52 lines

[00:00]
Rhea Wong
Hey, you, It's Rhea Wong.
[00:02]
Diko
If you're listening to nonprofit Load on, I'm pretty sure that you'd love my weekly newsletter. Every Tuesday morning, you get updates on.
[00:09]
Rhea Wong
The newest podcast episodes.
[00:10]
Diko
And then interspersed, we have fun special invitations for newsletter subscribers only and fundraising inspo because I know what it feels like to be in the trenches alone. On top of that, you get cute dog photos. Best of all, it is free. So what are you waiting for? Head over to riawong.com now to sign up Foreign. Welcome to nonprofit Lowdown. I'm your host, Rhea Wong.
[00:38]
Rhea Wong
Hey, podcast listeners. Your girl Rhea coming to you once again with nonprofit Lowdown. I am super excited because today I am talking with my friend Dego. Deko is the executive director of the Brooklyn Debate League. And today Diko and I are going to talk all about really what is their Cinderella story is how I think about it. This is not your typical trajectory of a nonprofit. And I don't know, I just feel like a lot of luck. I don't know, someone's looking out for you and the universe. Things have. Which is not to say you haven't worked for it, but you've had a lot of lucky breaks. And I want to talk about what that's been like for you because I think sometimes we think about the good stuff, right? We just think, oh, gosh, if Mackenzie Scott just dropped a million dollars at my lap, I'd be super. I'd be set. But I think the other side of the coin, which we don't talk about, is what happens when you do get unexpected success and how do you prepare to scale up really quickly. Diego, welcome to the show.
[01:36]
Diego
Thanks so much, Rhea. Happy to be here.
[01:38]
Rhea Wong
All right, let's get into it. So before we get into all of the amazing things that happened to you along the way, bring me back. Bring me back to being a high school teacher in Brooklyn teaching a bunch of kids about debate.
[01:51]
Diego
Yeah, so I started my career in Harlem, actually, and I was there for four years, and I was teaching the first year of teaching. I also started coaching a debate team. Did there for four years, and then I went to Brooklyn, did that for eight years. And at both schools, they didn't have debate teams before I got there. And it really mattered to me that I built debate because debate was the thing that changed my life when I was in high school. In fact, three out of four of the siblings in my family did speech and debate in high school, and it changed all of our lives. So, like, I just personally experienced, like, this was an activity that changes kids trajectories. And as a teacher, I saw that impact immediately on my students. And kids started getting good. Kids work hard, they were motivated, they, within a couple of years started getting very good. And by 2016, 2017, I qualified our first kids to the national championship. And when my kids came back from nationals, they looked at me and they were like, where was everybody else? Because what happened at Nationals was they started noticing that they were some of the only kids from low income public schools competing on that level. And there were thousands of kids who do speech and debate competitively in this country every year. But I can count on one hand the number of schools that are low income, Title 1 schools that have competitive debate teams on that level. I was very lucky and blessed that I got to work at one of them and worked with brilliant kids. But when we came back that year from nationals, a couple of us, the kids and I, like, we and the alumni, we got together and we were like, all right, so what can we do about it? And we started partnering with some local private schools and parochial schools that had established programs. And they, they were all for, how do we make this activity more equitable? And we built the Brooklyn Debate League. This was in 2017. I was still a full time teacher, I was still a full time coach. This was a side project. This was a thing that I did. I had no idea about nonprofits, and it wasn't even a nonprofit for a couple of years. It was just a thing I on Fridays. And like, we opened up our high school after school and we welcomed welcome local middle school kids who didn't have debate teams. And my kids ran debate for them. So they taught them, they coached them, they ran tournaments, they judged the tournaments, they gave them feedback, we ordered a pizza, we gave them little trophies. We called it a day. Like, it was great. And then we did that for a couple years. And then, of course, everything changed in 2020 with the pandemic. And at that point, I had left the school, went on a side journey, like a little side quest to go to rabbinical school for a semester. I thought that was another calling, but I kind of boomeranged right back to this calling. But anyway, so like, during 2020, I'm not teaching anymore. The kids are. All the kids are missing out on so much, especially here in New York. And so we moved this whole thing online. And I was shocked to find out that there was so much eagerness for it. The kids were desperate for a chance to connect with other kids.
[04:35]
Rhea Wong
And.
[04:35]
Diego
And we had weekly Classes online. We had weekly tournaments online. We had a week, a summer camp for six weeks online. It was just something fun to do where the kids were like, oh, yeah, I haven't lost everything. I still have a way to do this thing online. And we did that for a couple years.
[04:50]
Rhea Wong
I just want to pause there for a second because I don't know if you. Have you seen that show Adolescence on Netflix?
[04:57]
Diego
I have, yes.
[04:58]
Rhea Wong
Yeah. So there's a lot that was very thought provoking. But one of the things that I think the police officer says is I think a kid is okay if they feel like they're good at one thing.
[05:09]
Diego
Yes.
[05:10]
Rhea Wong
And it seems to me that you were able to help a lot of these kids unlock a thing that they were really good at. So if you could explain, because you and I have talked about the power of speech and debate and the fact that Oprah was a speech and debate person. What is it that you think is special about speech and debate that really helps kids unlock a sense of self?
[05:28]
Diego
Yeah. So when we talk about speech and debate, I should also just say what it is because a lot of people don't know if you ever watch the Olympics or you think about, like, track field, Right. It's not one event that there's like a dozen events and there's like a sprint and then there's a half marathon, there's a marathon, there's a relay race. There's all these different parts. Right. And it's. We call it track and field, but it's got all these different categories. Competitive speech and debate is the same, so we call it speech and debate, but it's got all these different categories. And some of them are purely public speaking. Some of them, you memorize someone else's speech. Think TED talks or commencement speeches. Some of them you write your own speech. And like you, you make your own TED Talk. And like that, you give the speech every time. 10 minute speech, you memorize it, you give it all year. Some of them, you don't know what the topic's going to be until you get there. And then in 30 minutes, you write a speech and then you give the speech and it's about something in current events and you don't know what it's going to be. And some of them are less about public speaking, more about performing, where you get a scene from a play and you cut it and you act it out by yourself or with a partner. Maybe there, there's some categories where you are reading prose and poetry. Like there's all this speaking and acting stuff. And then that's just the speech side. There's the debate side where you are arguing with another person. Maybe it's one on one, maybe it's two on two. Maybe it's a room of 15 kids. There's different categories there too. So why is this helpful to kids and why is this uniquely changing kids trajectories? When you think about moments in your life that were high stakes moments, usually, not always, but usually they involve talking to someone else. And usually there's some sort of dynamic at play that makes it intimidating. Maybe it's a power differential. Maybe you're interviewing for a job and you're talking to a boss, right? Maybe it's a class differential. Like I was a first gen kid and I remember being in college feeling intimidated that all of the people sitting in the seminar table around me like had parents. Some of them, their parents were college professors and my parents didn't go to college. Right. So maybe it's a class thing, maybe it's a race thing. I'm white. This is something I haven't experienced because of my privilege. But many of the students, most of the students that I have teach, I have taught. This is something that they've experienced as people of color living in this country. But for whatever reason, frequently when you are having a conversation that's high stakes with someone, there's often something that makes it scary. And that's on top of the fact that just in general public speaking is the number one fear of Americans over dying. That's true. They've done studies on this. So there's a baseline. Everyone is terrified of this. And then there's all the other identity based things that come into play, to say nothing of the ideological things that come into play. It's scary to talk to someone that doesn't agree with you. And especially right now, I mean, we're seeing this in our country like it is. Many people would rather just cancel someone than debate them because it's, it's scary. And look, this is a conversation we're not going to have right now. But I will say it doesn't get us anywhere when we are just when we are not engaging constructively. If we're going to move forward, it's because we are communicating, we are collaborating, we're compromising. You don't get anywhere but being like, I'm in my righteous fear and you're in your righteous fear. Right? So anyway, for all those reasons, when we think about the power of being able to walk into any space regardless of who is in that room and how they might be different from you and how their lived experiences might be different than yours, how their ideas might be different or yours walk into any room and say, look, here is what I want to say and then here's the real clincher to listen to what they say back. Like that is power. You can't buy that. That and private schools know this. Like there is a reason why half of the people sitting on the Supreme Court right now did speech and debate in high school. There is a reason why almost every private school in New York City and around the country has a competitive team. This is a skill that it changes kids lives. It gives them a power to be in those spaces and to make the decisions and to be influencers and for people to listen to them. And unfortunately, maybe it's not surprising that the communities that have been historically silenced and suppressed are also continually being silenced and suppressed in this way. Because many of those schools, we're talking about low income schools, we're talking about public schools, do not have the bandwidth, don't have the institutional capacity, don't have the resources. Like there's. This costs a lot of money to teach kids how to stand up and, and it's. I can't think of a skill that's more important, especially right now, like thinking about these teenagers as the folks that will be voting, as the folks who are taking over the leadership in our country. Like we as a society, like when we're trying to defend democracy. This is democracy. This is what it was in ancient times. This is what they taught kids was rhetoric and speech and debate. This was like the pinnacle of your education. Where is it right now? It's not happening in our K to 12 curriculum. And so we have to supplement it. And the way that we supplement it is with competitive speech and debate.
[10:40]
Rhea Wong
Diko, I am a believer. That was awesome. And I have so many thoughts here. I'm thinking about the fact that democracy dies in darkness. I think exactly to your point around how do we help people elevate their voice to say that they're not okay with what's happening in this country right now, to say that we care about things like due process and voting and rights. And this brings up for me, I hope I won't disturb, but it's a quote from Rumi. Beyond doing and wrongdoing, there's a field.
[11:11]
Diko
I'll meet you there.
[11:13]
Rhea Wong
And I think the capacity to listen and to listen without defensiveness and jumping in. And you're right. And I, and you know, you're wrong and I'm right, and whatever is the core of the fabric of our society. And when that is torn asunder, what is left?
[11:33]
Diego
This is how we invest in that, particularly in communities that have been systemically silenced. Like we. What do. How do you confront silence? You lift up voices.
[11:43]
Rhea Wong
Okay, Diko, we're gonna have a side conversation about how we're gonna scale this out and start the movement across the world. But before we do that, let's talk about. So here you are doing amazing work with a pretty small group of kids who were in your classroom, or maybe not in your classroom, online, and then something happened which kind of. It was a rocket ship shot in the arm. What happened?
[12:08]
Diego
Okay, so remember how I said before I was a teacher, I was not a non profit director. I had no experience in building non profits and running non profits, working for none of that. In May of 2022, I was a full time history teacher, still running Brooklyn Debate League online for fun. At this point, like, I'm paying my alumni who are now. The kids that helped me started are now in college. I'm paying them every week to come and run it to be the teachers online, like from their college dorms. Paying them for this out of pocket, by the way, because if this is not a. We're not charging anybody for this. We're really trying to support low income communities. One of my alumni, my first ever students, his name is Jonathan Conyers. I taught him in 2009 at Frederick Douglass Academy in Harlem. He's helped me pay for this. So at this point, he had just graduated from college and he's got a right out of the college. He, he was a Neo. He is a neonatal respiratory therapist at NYU. And do the math on this, right? This is 2019. 2020. He's the guy that ran the ventilators during COVID Okay, guys, a 20 year old kid. All right. Anyway, he hears about what I'm doing and we've stayed in touch this whole time since. Since his high school graduation or since high school? For more on his story, you should read his book I Wasn't Supposed to Be here. It's a memoir that talks about how debate changed his life. Anyway, we're in touch. He's helped me pay for this. So he and I are writing checks every month, like paying the alumni. And eventually I'm like, john, like, I don't know. I can't. What are we. What's the plan here? He's got three kids of his own and he's. I don't know, Dico, what's the plan? And he goes, listen, I got an idea. And when my students tell me they have ideas, I listen because they're usually right. And John ends up telling the story of his life and how debate transformed his path to the Instagram platform. Humans of New York. And Humans of New York interviews John and interviews me, and we end up. Brandon Sanson, who runs Humans of New York, writes, I think at that point the longest post he'd ever like, long story, long form post, has ever written about John's life.
[14:07]
Rhea Wong
Wait, and did John know him before or was it a cold pitch?
[14:10]
Diego
Yeah, John cold pitched him. Gee, and I wonder where he got the confidence to reach out to folks. And just really though, and he attributes this. He came to me really special and brilliant, but he just cold pitched it. And Brandon at that point, I don't think had even responded to a cold pitch before. Like, Brandon's whole limo was like going around the streets of New York and just like interviewing, interviewing random people. Brandon's Wait, what is this story? Tell me more. This is a kid that he was in homeless shelters. His family was suffering from substance abuse problems. Like, he had been through so much in his life and he joined debate team, in his words, to keep himself off the streets and so to pick a new path. And it worked. It got a full scholarship to college and then was saving people on the front lines of the pandemic in 2020. So Brandon's this story is amazing. Tell me about this. And he writes this post that goes absolutely viral. And John the whole time is telling me, dico, this, it's going to come. It's going to be big. Get ready. And I'm like, yeah, I got lesson plans to write, dude. But I don't know. I. Please, I know. And he's, you know, it's coming, it's coming. And I was like, sure he was right. Because on May 9, 2022, this story goes live and millions of people read it and thousands of them donate to the GoFundMe that was attached at the end of the story. So that within 48 hours of this story being posted, the GoFundMe for the Brooklyn Debate League that we had posted at the top of the end of the story there had raised $1.3 million, which is, suffice it to say, more money than I have ever seen in my life as a public school teacher in New York City, more money than John's ever seen in his life. And the two of us at that moment were like, okay, we got to do this thing, and we got to do it right now. So I finished off the school year and I left the classroom, and. And John talked to nyu, and he's part time at the hospital, but now is like part time with us at Brooklyn Debate League. We started that August with summer camp with no experience between us with nonprofits, with no. I knew how to write lesson plans, I knew how to build debate teams. I did not know how to run a nonprofit. But we had $1.3 million in the bank and 30,000 people on our mailing list who were in our corner. And that's how this whole game started.
[16:19]
Rhea Wong
Wow. So many things here. Okay, so now here we are. We're may the time that we're taping this May 1, 2025. So it's been all of three years. Three years in the seat full time. And I think you and I met pretty early on in your nonprofit life. And I'm just curious because I think when we talk about nonprofits, we talk a lot about the structural things like the staffing and the this. And how do you do a fundraiser. We don't often talk about the internal shifts that I think we need to make within ourselves to be the leaders, to see ourselves as leaders, to have the confidence to run this thing. Especially in your case, because it was just like meteoric. So it wasn't incremental. You didn't get to grow into it. It was like public school teacher one day, head of a multimillion dollar nonprofit the next. So I'm curious if you could think back, what are the internal shifts that you felt like you had to make in order to step into this new world?
[17:18]
Diego
Yeah, it was really hard, actually. The only thing I'd ever done at that point was teach, and suddenly that wasn't my job anymore. I think one of the biggest shifts I had to make was to. And it's still ongoing, honestly, but it was to figure out what did success look like for me, and then how do I chase it? When I was a first year teacher, that was its own path, right? It was like, all right, who do I have to talk to? Who are the mentor teachers I need to sit and observe, and how do I get coaching and how do I learn how to do this? And also how do I make changes every single day to make today a little bit better than yesterday? And my first year of teaching was awful. But most people. It's really hard to be a first year teacher. My second year of teaching was a lot better. My third year of Teaching was amazing, and I got on this curve that felt like the learning curve felt so good in teaching. And then when we started Brooklyn Debate League, I was like, and I'm back to the beginning, because here I am again. And I need to go find the mentors, and I need to figure out, like, who are the people that are doing this? I need to learn from. I need to figure out how to be. How do I train, who can train me? And I need to every day figure out, all right, how can I make this process tomorrow a little better than it was today? And my first year in the job, it was really hard, and I made a ton of mistakes, but by the end of it, same thing with my first year of teaching, I was like, all right, how's year two going to be different? And how's your three going to be different? And I. It has been just like with learning how to be a teacher, the learning curve has been exponential. And I feel right now so grateful for all of the training, all of the mentors, all of the people in my network that I connected to, because I look back and I'm like, I was a fish out of water. Like, I was. I was. We had all this money in the bank, and I had no plan and no idea how to do it. And the reason why it's working is because I got a lot of help.
[19:08]
Rhea Wong
Yeah. I think there's so many amazing things about you, but I think one of the things that, to me, suggests that you are going to be a success is you are not afraid to ask for help. And I think sometimes, and look, myself included, I think I. There were points in my career I should have asked for help, and I didn't. I think what really differentiates the people who are going to be on the trajectory are the ones who are willing to ask for the help, willing to invest in the help. I know you worked. We worked together. I was coaching with you. You were also coaching with Brooke, who is a perennial fan favorite on this podcast. And so when I look at the things that you've done, which there are many brilliant things that you've done, I think you looking ahead at who's done this before, who can teach me what is ahead? Because, sure, we can all learn by doing, but wouldn't it be easier if you can get the CliffsNotes from someone? Yeah.
[20:00]
Diego
I mean that the first months that I was on this new job, my whole goal was talk to as many EDs in New York City that are educational, aligned as I could. And I talked. And for every single One. I was like, okay, who else should I talk to? I was like, okay, who helped you? And like, that is how I found you. That is how I found Brooke. That is how I have the EGF accelerator program that I did. Like, all the programs, all the mentors. It's because I. I just cold emailed folks and I was like, hey, I'm a new ed. Do you have any. Can I talk to you for 10 minutes just to pick your brain? And I would say I probably made talk to 40 people within my first two months on the job. One of those phone calls didn't go well, and the person was like, no, I don't got time for you. The other everybody else was like, yeah, I'd love to talk to you. All these people helped me and I'd love to help you. And I'm like, okay, this is a community. I just got to reach out. And people are really eager to help and to support each other.
[20:51]
Rhea Wong
I have to say, this is what's kept me in this industry, in the sector for 20 years. It's really good hearted, generous people who want to do the right thing. And sure, of course, every once in a while, you will find that one person you're. But people generally don't get into the nonprofit field because they're selfish, awful people.
[21:11]
Diego
Yeah. This is not like a cutthroat. Like, everybody wins if we are successful. It's. Yeah, it's been really helpful getting into the community.
[21:20]
Rhea Wong
Awesome. Okay. There's so many other things to go here. The thing about you, Diko, that is actually quite incredible is you have this incredible ability to connect with people. I don't know, it's your personality, it's your vibe. People just really want to help you. People are really drawn to you. And so you've had. I don't know if I'm allowed to say, but, like, you've had some very impressive folks in your corner. And when I talk to you, you're like, oh, I know this person. I know this. But I'm like, wait, what? Like, you have this Rolodex that I. Most people would give their left kidney for maybe both their right and their left kidney. So talk to me about how you built this incredible network as starting, as you say, like a public school teacher who didn't come from this family who could make phone calls, didn't have a trust fund, didn't have, you know, all the things that some folks do have. I don't know. Did that question make sense?
[22:12]
Diego
It did, and it's a good question. And it's one that I think about a lot. So the Rolodex that we're talking about here, there's everybody on there from celebrities. John and I were invited on the Kelly Clarkson show. And I was like, I genuinely. I live under such a rock that when her producer called me, I had to Google who Kelly Clarkson was because I was like, I think I've heard of you, but I'm not sure that's true. I have now since learned about her. Love her, Fantastic. She was a lovely person to meet.
[22:35]
Rhea Wong
Great.
[22:36]
Diego
And then Malcolm Gladwell cold emailed me a couple years ago and was like, hey, I lost the debate recently. I'd love to know why. Do you think you could tell me? And I was like, sure. Okay.
[22:45]
Rhea Wong
Like, Malcolm, cool. Call me.
[22:48]
Diego
There have been some, like, real folks. I cannot take credit for that. Just heard about us and reached out to us, and that's great. But I think most of the people in my corner that are folks with varying degrees of networks and wealth and support, like, they're folks I have met over the years. And, like, the reason why it's worked is because I try to be nice to people. And that sounds really, like, silly and cliche, but. But that's it, right? So here's an example. At the regular tournament, just like a Saturday tournament, on one random day in October three years ago, I was sitting in the Judges Lounge with 150 other people and these two women were next to me and they were like, oh, I've never judged online before. Do you think you can? Can you? Do you know how to do this? And I was like, yeah, sure, no problem. Let me show you. And I sit with them for a couple minutes and I show them how to do it and whatever. And then I find out, like, one of them started her own nonprofit 20 years ago. And it's. It's huge. It's national now. It's amazing. And she was like, oh, wait, what do you do? Oh, interesting. And like, we just connected where she's a huge supporter of BDL now and, like, we are in touch and it's great. The other one, her kids, both of her kids did speech and debate. And she became a supporter that day and is still a pretty substantial support. And I didn't reach out to them because they were potential donors. They just needed help. And I was like, hey, sure, no problem. And I was hanging out in a space where I know people care about this thing because it's a debate tournament, right? And what I do is debate. And that's not why I was there. I was there because my kids were there. But while I'm there, might as well be nice to people. You're not. You might as well help people when they ask. Like, you have no idea where relationships are going to lead, but everything is really grounded on relationships. Like, that's where this starts. And I really learned this not as a nonprofit director, but as a teacher. Like, kids, you can have the best lesson plan in the world. It's not going to land if the kids don't trust you. And you have to give kids a reason to trust you. Especially I'm a white teacher showing up, like, in mostly black and brown spaces. Like, they got lots of reasons to not trust me. Lots. Like, I have to earn their trust. I can't take that for granted. So I would try to be kind to them. I would try to make my class fun. I would make sure that they knew I cared about them. Like, I would go an extra mile to. To lift them up and to support them and to celebrate them. So that by the time that we were doing Latin class or we were going to debate tournaments at Harvard, or we were doing things that were intense, the kids were invested and they were like, oh, yeah, I trust you. Like, I know you care about me. We got it. And so this is something I've been doing since I was teaching. And I just think it's been really. It's followed me. Like, it's one of the things I've. And I try to teach my students. It's one of the things I've learned in my life that's be kind, be generous. Like, just be generous with your time. I don't have a lot of money to give. I'm a public. I was a public school teacher and now a nonprofit director. But, like, I've got time and I've got. It doesn't cost anything to be kind. And it comes back.
[25:38]
Rhea Wong
Yeah, Yeah, I love that. Okay, two more questions because we could talk forever. So now that you're three years in, you've had tremendous success. And I don't think this is confidential, but there, there's some big things in the works. A documentary, possibly a film like this. It again. A Cinderella story. So what now? Like, where are you today? Three years into it, what are you thinking about in terms of your fundraising? How are you thinking about growing your organization? What's the staffing structure? What does it look like today that is different than it looked like three years ago, which I guess it was non existent three years ago.
[26:16]
Diego
So what it Feels like today is. It feels like exactly my third year of ed is exactly what it felt like my third year of teaching. Like, people talk to me from day one of grad school and Teach for America Institute and all that stuff. They're like, okay, here's what backwards planning means and here's how you write a lesson and a unit plan or whatever. But like, it didn't sink in because I wasn't ready to learn it until suddenly it was like, oh my God, I see all the pieces of the puzzle and how they fit together. This is what I need to do. And once you do works. So from day one of being an ed, people have talked to me about like, all right, how do you build donor pipelines? Like, how do you work on your marketing and your newsletters? And how do you build relationships with major donors? And how are you managing a budget that's like, reasonable? And like, I knew all the pieces like, but like, I didn't have the capacity yet to put them all together. And suddenly the pieces starting to fall into place and I'm like, oh, wait a second, I know what my job is now and I know what success looks like and I know how to set myself goals. And like, I know, like I've known these things cognitively for three years, but suddenly I like, know it viscerally and I'm like, okay, I actually like this job now because in the beginning I missed teaching. It was all I ever knew. And like, I knew I felt successful. And I'm like, wait a second, now I know what it feels like to be successful here too. I was just saying to my girlfriend this morning, I was like, listen, babe, I know the last couple years or months or whatever, I've been really present since we started dating and whatever, but just so you know, this job, we're like about to take off. So you got to forgive me, be a little lenient because I'm about to dive in a whole different way. And I'm excited about it. Like, I'm not. It's great. It's just, I didn't know how to do that. I'm just starting to figure it out and I'm like, wait, okay, this is how my newsletter plan, my marketing plan, my LinkedIn plan, my donor pipelines. Like, my, Like, I'm seeing how the pieces are going to connect and the impact of that is like, I've got a budget next year, which is the most accurate budget I've had so far. I can say to my board confidently, next month, guys, here's exactly what we're going to raise, and here's how we're going to raise it. And here's exactly what it's going to cost. And here's how I know what it's going to cost, because, like, here's all the drivers and the aggregate costs that I've been compiling for the last three years. I got it. And then once I got that and I'm, like, on solid footing, I'm like, all right, like, then it's time to look forward. I couldn't really do the five or the ten year plans that you broke. Everybody, you're not wrong to tell me how to do it, but I couldn't do it yet until I'm on solid footing. And now I'm there. So now I have the room I need to start thinking, cool, where do I want to be in five years? Where do I be in 10 years? And what do I have to do differently next year to get there?
[28:53]
Rhea Wong
Yeah. Yeah. I just think about when you're learning how to ride a bike, you're like, I see the Tour de France. I understand how that happens. But I am still, like, wobbling on this bike, so I need to figure that out first. I feel like you're out of the wobble. And now it's okay, let's talk about the Tour de France.
[29:10]
Diego
Yeah. Out of the wobble. That's my motto for this year. Out of the wobble. That's it.
[29:14]
Rhea Wong
Yeah, yeah. Okay. I got it.
[29:16]
Diego
I'm gonna make. I'm gonna.
[29:17]
Rhea Wong
For folks out here listening, because you and I have known each other for a couple years now. It's been such a delight seeing your growth, seeing you change, seeing you think about fundraising differently. Can you talk a little bit about what that trajectory has been like for you? In particular, what it was like to work for me? Because folks listen to this podcast who might be considering applying to work with me. So if you could just give us a sense of what is it like to work with me.
[29:44]
Diego
Yeah, I would be delighted. I met you, Rhea, at the. You were a guest speaker at the EGF accelerator. And this is another example of how you said earlier, like, how do you expand your Rolodex? I liked your presentation, so I emailed you afterwards and I was just like, hey, thank you. I thought you had a great presentation. I'd love. I just introduced myself and you were like, oh, really? Here's my podcast if you're interested in my course. Like, here are some things I'm offering. I'm like, all right, cool. So we Started working together, I think you said, two years ago. And I took your course. I know you've changed the name of it. What is it called now? Big. Is it Big Ask Big Ass Gifts? Yeah, Big Ass Gifts. Love it. So I took that course, and again, at the time, I was in a place where I was just learning, and I don't think I was really able to implement all of it yet. But what I did get out of that course was like, one, the foundations that. Now a year later, I'm like, ah, yeah, I know what to do, because I learned this in Ria's course. And two, I got access to you and your network, which has been amazing. So since that course, there was like, another mini course that you connected me to that somebody, like, was looking to get a core group of folks together to talk about this new way to raise or to build relationships with major donors. And what I learned in that changed the whole game for me. Like, I've been playing with that all year. And like, now when I have a prospective major donor that has expressed a lot of interest and has said things to me that, like, they. They are basically saying, I am looking for my people. I think you are my people. What is our next step? Three years ago, I would have been like, I don't know. Like, in fact, I was like, I don't know when people ask me that question. Three years ago, I didn't have a plan. Now I know exactly what my plan is. And it's because of folks, the things that I learned in your class and folks that I met through your network. And it makes me feel so much more confident in doing my job as an ed. And I didn't know when I started this, a thing about fundraising, right? I was. I knew a lot about debating and a lot about coaching debate. I didn't know a thing about fundraising. But everything I know now is a lot of. It's because of you personally and people you've introduced me to, and also from trainings, like, from Brooke and other folks. But, like, working with you, it changed the game for me. And I will also just say that if you are someone that's listening to this and you're like, yeah, but I don't know if I have money to spare to pay for courses right now or to pay for consultants right now. I didn't know if I did either. Despite the $1.3 million that we raised, we gave a lot of it away immediately because I did not know how to do my job right away. And we were just, like, giving Away programming for free. So I was worri about money and I was like, yeah, I don't know, it's a lot of money, but sometimes you have to spend money to make money. And I have zero regrets about investing in my professional development, particularly around fundraising. That is, that is my primary job in this role is to make sure that we stay afloat. And in order to do that, I needed to develop myself with fundraising and you helped me do that.
[32:38]
Rhea Wong
Oh, thank you so much, Dico. All right, let me just ask one last question because I'm very nosy. How much do you think that you've raised as a result of our work together? If you had to guess?
[32:47]
Diego
Oh my gosh, I don't even know how to answer that question because it's so baked into everything that we're doing. I will say this though. I was just looking at these results, the budgets last night because I was doing a grant. I was like, oh damn, we raised twice as much this year as last year. I wasn't even tracking that like from individual donors. And that's like in the margins of like a hundred K. Like I think the first year we raised like 150K and this year we raised 250K. And I was like, wait, what we did? And like, it's like all of that is what's baked into that are moves that I made that were different this year that I wouldn't have thought to make if I hadn't learned it from folks like you.
[33:25]
Rhea Wong
Diko, I'm so pleased. And I think you're right at the beginning. The way that I see you rising is just, it's like a. I keep saying a meteor, but buckle up. It's going to be an exciting ride, friend.
[33:38]
Diego
Yeah, I can't wait.
[33:40]
Rhea Wong
So, Dico, thank you so much. It's been so fun. And of course I'm always here for you if you need anything. By the way, we should hang out and irl.
[33:49]
Diego
Yes, we love that.
[33:50]
Rhea Wong
All right, Dico, thank you so much. Good luck with you, Good luck with everything. And.
[33:57]
Diko
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