Speak For Change With Thomas Sage Pedersen
Welcome to Speak for Change with Thomas Sage Pedersen! Our mission is to inspire and promote positive and lasting change in our local & global communities.
Speak For Change With Thomas Sage Pedersen
Jacob Martinez | Leading In The Storm: Founding Digital Nest Nonprofit, Radical Transparency,Training Next Generation of Diverse Leaders, Fundraising Wisdom and more
We trace Jacob Martinez’s path from outsider to builder and unpack how Digital NEST turns first-gen talent into confident leaders through transparency, training, and courageous asks. Real talk on hiring, culture, and stress gives a grounded playbook for turbulent times.
• founding story shaped by class contrast and belonging
• embedding leadership training for staff and youth
• professional development funds and clear advancement
• nonprofit hiring realities and people decisions
• COVID pivot to online tools and community support
• post-pandemic outreach to bring youth back
• radical transparency with finances and access
• compensation strategy tied to equity and runway
• fundraising courage and mentorship on the ask
• stress management, sabbaticals, and boundaries
• advice for emerging and seasoned leaders
Support & Hire the youth! Find us at digitalnest.org and on socials. Email Jacob at jacob@digitalnest.org
Bio
Jacob Martinez, founder & CEO of Digital NEST, is a social entrepreneur, tech educator, keynote speaker, and cutting-edge community collaborator. His mission is to bridge the digital divide and create opportunities for young people in rural communities to access the economic and social benefits of technology.
Recognition for Martinez's work includes: 2020 James Irvine Foundation Leadership Award, the Draper Richards Kaplan Foundation Entrepreneur Fellowship, 2024 UC Santa Cruz Alumni Achievement Award, and the 2015 Entrepreneur of the Year for Santa Cruz County, among others. He speaks frequently about his work at events, including TEDxSantaCruz and the 2015 White House Tech Meetup.
He sits on the boards of the Silicon Valley Leadership Group Foundation and the Center for Rural Innovation. He is an External Special Adviser to the UCSC Chancellor as well as an Advisor for Reservoir Ventures, a modern investment firm focused on supporting entrepreneurs in Central California and the Monterey Bay Area. When Jacob is not making sure youth in rural communities are ready for big careers, he spends time with his wife and three kids, and enjoys gardening and traveling.
Welcome to the Speak for Change podcast. Um I'm your host, Thomas H. Peterson, and today we have Jacob Martinez, uh founder and owner of DigitalNest. CEO, yeah. CEO. Yeah, CEO. That's um of Digital Nest, which I am here at Digital Nest, and this place is amazing, man. Like you have these like soundproof rooms, and I was just talking to you offline that like everyone is super nice here. Like I'm just like, you know, I'm like, oh man, I feel so loved just being in this space. So thank you for being on, man. Yeah, of course. And we got you. If you need snacks, if you need a place to work, come on down, man. Oh man. Um, so yeah, today, today, uh, this is part of an ongoing series about it's called Leadership in the Storm. Um, but just generally about leadership and going through different strategies of going through turbulent times. And, you know, you've been you've been doing this for quite a long time at this point, you know, and through I'm I'm imagining many obstacles, um, including COVID. You know, uh and so yeah, I'm just before we get dive into that, like, have you always kind of been a leadership guy? Like, have you always been in leadership roles or is this new? Like, what what's your history with leadership?
SPEAKER_02:Yeah, no, it's kind of like uh no, never, you know, I was you know, before Digital NAS, I was at another nonprofit. And I, you know, I I I moved up the ranks and you know did well, but I was still like three or four layers below the CEO. Like so I I I didn't know what it meant to be a CEO or an executive director. And um, so no, I think I've kind of just learned um you know, the 11 years I've I've had Digital NAS, like I've learned all the ups and downs of leadership and expectations of leaders and and uh got a lot of help from a lot of people, you know, made a lot of make big mistakes. And uh so yeah, I've been kind of thrown into it. You know, when you've when I launched this thing, I didn't know where I didn't know what it meant to be a leader.
SPEAKER_00:Yeah. So I mean, on top of that, like, and I just this is just pure curiosity at this point. Um like what were you like in high school? Were you like part of any kind of groups or were you involved, or what was your vibe then?
SPEAKER_02:Yeah, it's it's it's actually interesting because this is like at the core of how Digital Nest like came to be, actually goes all the way back to middle school. So um, and actually to my parents. Like my mom's and my my my mom, the border crossed my mom's side. So my mom's like born and raised in LA. My grandparents spoke perfect English, you know, their my grandfather served in World War II. Um, my dad was an immigrant into this country. Um and he went through high school in LA, and then the Vietnam War came around, and uh uh he served in during Vietnam. Um, but he was actually a Mexican citizen. So he was serving in the U.S. military as an officer because my dad was pretty bright, and so he tested really high and um became an officer in the military, and he was a Mexican citizen. He got his citizenship after the war. Um but so then he after the war, he he we moved, we went back in LA, threw the GI Bill, went to community college, went to Cal State, LA, and got a degree in accounting. And so growing up, my dad was an accountant and bilingual, and we moved around a lot in our lives. We lived in Mexico City, LA, and then my freshman year, and I grew up in like in LA in this, uh like in North Whittier, uh, where all my neighbors were either Mexicans or Filipinos. That's all that's all I knew. And all my classmates, classmates were Mexicans or Filipinos. Um, and then my freshman year of high school, my my my right before I was going off to high school that summer, my parents dropped this bomb on me and said, Hey, we're my my dad got an opportunity in Texas. Um, and I'm this typical LA boy. Um, and we're moving to Texas and Dallas Fort Worth at that. And moving from LA to Dallas, like the houses you could buy are just so much because there's so much land, there's so much available. My dad was super proud of this beautiful home he bought us, uh, but he didn't know it, but he put us in a very affluent area. Yeah. And of my class of uh 300, I was one of only 15 people of color, um, and struggled and barely graduated high school. I was I was pissed off, LA boy, thrown in Texas, and the the culture, the clash, the the the conservatism, the the hatred, um, and at the same time, all the wealth and opportunity that was there. And so my high school had carpeted hallways, you got brand new textbooks every year. Every kid was going to college. They were going like it wasn't if there wasn't a question of are you going to college, the question was where you're going to college. And they were going to Northwestern, Notre Dame, Duke, UT, University of Oklahoma. And so I saw for the first time in my life like true privilege. Like, and like what wealth and opportunity brings and the confidence that these kids had walking around. And I didn't know it, but that's like a I've always wanted to recreate that for people who didn't have it. And fast forward, went to college barely because of athletics. Uh, got kicked out my freshman year of college and at the age of 19 took off to San Francisco because I had a cousin at San Francisco State and couch surfed and uh moved into the mission in San Francisco where people were just trying to survive. And that was kind of like thinking to myself, what if I could bring opportunity and privilege to these people? And um that was, you know, uh went to UCSC, that's how I came here, got a good job, and then uh had this idea of the digital nest.
SPEAKER_00:Okay. I feel like that was like a a low-key mic drop moment um right there. I mean, I just love this, this um, it's truly reminiscent of like the hero's journey kind of vibe of like your your life leading up to this moment, you know? Yeah. Like, you know, I I've interviewed quite a few different leaders at this point, and it's interesting seeing kind of like people who've been like, oh, I've been just primed for leadership my whole life, right? Well, you've been like you've gone through like struggles and turbulence and like not haven't considered yourself a leader. Um, but I imagine that brings a certain level of like empathy, I would think, to the people you're serving. I don't know, do you see any benefits of like kind of having that background um and being a leader right now? Is there any kind of like lessons or things that come to mind just with reflection?
SPEAKER_02:Yeah, leadership is embedded in everything we do here at the Nest. And that's like from the young people that we're working with and giving services to and helping build their confidence, give them the skills, build their networks. But we do that on the staff level too. Um like you, like a lot of my staff, 84% of my staff are from communities that we serve. So that so that they they've lived the challenges that our young people are living, right? Most of a lot of my staff still live at home with their parents because they can't afford to buy a home, right? A lot of a lot of my staff are the first to go to college and are the first generation professional, right? So no one ever taught them what it is to come into an environment like this and work and be productive and be professional and to like advance your career. And like so, so all those like all those things that I've kind of like have gone through and uh for myself, we we embed everything we do here at the Nest. We kind of consider ourselves kind of like a teaching hospital. Right. That's interesting. Yeah. So the our expectation with our staff is that you're not gonna be here forever. You're not gonna retire here. We want you out, we want to build up your skills, we want to get you out into other organizations so you could bring the knowledge and the skills into other uh other and uh other other organizations.
SPEAKER_00:Right. Yeah, and I mean that's beautiful. It's like you're just you're here to train leaders pretty much. Yeah, absolutely. And I so I think like what are some principles that kind of come with like training leaders here that you've learned from your experience and like why why do why do those principles matter?
SPEAKER_02:Yeah, so every one of our staff um has uh$500 allocated professional development funds um for you. That's amazing. And that's like across the board. Yeah, and and it's and if you're not using it, your supervisor has to justify why it wasn't being used. So so it could, but you know, there's a lot of times there's a lot of free programs, and it's like, oh, I well, I got I got this person to a free program, and so okay, cool, like no worries, but we we we have to be doing professional development for our staff. Um, every one of our our our eval our performance evaluations embedded in that is uh conversation around your career advancement, your career ladder.
SPEAKER_01:Yeah.
SPEAKER_02:Um our our we have a person here who's in charge of all of our HR. She's really focused on people, advan like advancement. So we're developing uh uh tools so that you can see what your professional goals are, uh, what are your skill sets, what are the things you're trying to grow in, and we're measuring you and your supervisor on your on that person's growth. Um uh and so we do things like that. We um we put people in leadership positions. Um you know, one of our cool story is one of our uh young managers, he just um he's going to Harvard Business School to be a part of our new pilot program to take emerging leaders and teaching them how to be effective managers. Um and so we're amazing. Yeah, yeah. So like opportunities like that, we're all over it. We encourage our staff to go. Yeah. Um, you know, so yeah, which it's we do everything that we do for our young people, we do for our staff too.
SPEAKER_00:So I'm still a little bit, I mean, I guess I'm a little confused because not everyone just has the intuition to say, you know what, we're gonna grow leaders here, and like this is what we're gonna put$500 for this, we're gonna, you know, help these people like really track their progress and you know, teach them accountability, responsibility, all these different things, right? Um like what really drove you to come up with these ideas? Or like, you know, were you brainstorming? Like, what was it just something from your upbringing that kind of was like, you know, I really want to do this? Or, you know, what what kind of fuels that?
SPEAKER_02:I think a lot of it's just my experience. Like, I, you know, I've um I was fortunate. I, you know, I worked at another nonprofit doing research on how to get more representation in tech. And I would go into rooms where I was the only person without a PhD.
unknown:Yeah.
SPEAKER_02:And this is like the National Science Foundation meetings and being in Washington, DC, and all these academics around me, and I I didn't feel like I belonged, right? Yeah. And then and then, you know, I'm I'm had this idea of digital nest, and I like, oh, help me know, I'll be the leader of it, we'll be a nonprofit, and and then yeah, come into this role, and no one's ever taught me how to be an executive director.
unknown:Yeah.
SPEAKER_02:And all the challenges that come with it around like being accountable, learning how to make hard decisions, learning how to fail, um, being okay with failure, um, being okay with like raising your hand in a meeting and using your voice. And like a lot of our a lot of our young people, including our staff, like they a lot of people, especially people of color, uh, don't have the privilege of growing up with a parent that sits on a PTA, that uh sits on a board of an organization, that's running a company, that's being an entrepreneur, has their own business. A lot of people of color, their families are struggling to make ends meet. They're working in the fields, they're working blue-collar jobs, they're working at retail, struggling paycheck to paycheck. They don't have the luxury to say, you know what, I'm gonna go volunteer and sit on a board of directors. Yeah. And then their kids seeing them, their parents modeling that behavior and coming home and sitting around the kitchen talking about, man, I really had to make this hard decision about budget cuts and like what are we gonna fund and what are we not? And so that's what I experienced in the early days of the NAS, and I've leaned on a lot of people to help me through that. And so just over the course of 11 years, really realizing that what we're doing is for young people, but a lot of the people that we're hiring need that same support. Yeah, and so that's our responsibility to them as prof like and and their success metrics. When they leave, we celebrate them, yeah, right? Like, oh, I got I'm going to another company, right? And I say, as long as you're as you're moving, if you're leaving the nest and you're going to a better opportunity, we're celebrating it.
unknown:Yeah.
SPEAKER_02:If you're leaving the nest and you're and and then and and you're taking a worse opportunity, that means we failed you. Um so we we we share all the we we celebrate and we report out all the staff that are leaving our organization.
SPEAKER_00:Yeah, and I'm getting like the chills over here. That's inspiring, you know. Um as you were learning to be this executive director, right? Going to C board meetings, like these skills. Do you have any memories of like some clear obstacles that got in your way during these this process?
SPEAKER_02:Yeah, I mean, uh, you know, the the hardest thing as a leader that I've struggled with is uh the hiring and firing of people. You know, um uh we're people a lot of people who go into the nonprofit world like are in it because we have big hearts and we want to give people a chance and we want to give people opportunity. And sometimes there's people that um aren't ready for that opportunity, and there's sometimes there's and no matter what you do, they're just not ready. Or some people who come in and realize that um they're doing more damage than they're than they're doing good, and like you want to like kind of coach them through it and help them, you know, get through there, but at some point you you gotta let people go. And I think that's the hardest thing as a leader. You feel like you fail them. Um it's hard to sit across from somebody and say, hey, this isn't working out, you know. Um, we've done it over the years and we try to do it in uh with as as um as fair as we can, you know, but it's tough. And because then, you know, you also have you know, with one thing you d one thing I didn't realize when I launched at NAS is like, you know, you like, oh I'm gonna raise money, I'm gonna put on good programs, I'm gonna hire good people. Yeah, we'll let people go, but then like you don't realize like there's HR, there's legal, there's finance, and there's all these like systems in place that like that constrain you, you know. So when like you're sitting across from somebody, you're trying to do as like fair as you can. Um, but there's systems that are that are preventing you from doing sometimes more for somebody. But so that's that's been like the hardest thing, like my biggest roadblock is just learning how to find good talent, learning how to grow talent, and learning how to say, you know, you know, thanks for your time, but it's just not a good fit.
SPEAKER_00:Yeah, I mean, I think a lot of people resonate with that, right? Um, you know, I just not trying to drop anything, but like, you know, like um my business partner, uh Jules, she's worked in a lot of different VP roles and stuff like that. And she just did this workshop with the Chamber of Commerce, and it was all about creating like teams and hiring practices and stuff, and I was like, man, and so many people there just like resonated with that specific topic matter, right? And I was like, man, so I'm wondering like what did through this process like of having to fire people, which I know for personally is like extremely difficult.
SPEAKER_01:Yeah.
SPEAKER_00:Um, but like more importantly, how has that informed your your hiring process?
SPEAKER_02:Yeah, you know, if you heard you're you're you're gonna hear people say like hire slowly, fire quickly. Like, but that's that those are people who are usually saying that in like from privilege. Exactly. Right. You know, because it's if you have a lot of resources and you have a lot of people, you can take your time hiring people, right? When but in the nonprofit world, when you see somebody with like skills, like you better swoop them up quick because someone else someone else is gonna pick them up, you know? And so uh so like you don't have that luxury of hiring slowly, and you have needs that need to be met because you're running out of money or you're not servicing your your you're not providing good services, and you need to get somebody in there to fill the spot, you know? And then you can't fire quickly because like someone needs services, someone needs support, or or you need somebody to you know do payroll. Like you can't you're not gonna just find anybody off the street quickly to come back in. So it's tough in the nonprofit world to that that that methodology of like hire slowly, fire quickly. I don't I think it's I think it's almost opposite for nonprofits, you know. Um and that's one of the rare things, I think. I think there's a lot of parallels between for-profit and nonprofit world, but I think the hiring and firing of people is one that's different.
SPEAKER_00:Yeah, what's um you say you're saying it's almost like the opposite approach, like pretty much like hiring quicker and then then like maybe taking more of your time to to fire somebody.
SPEAKER_02:You're like kind of forced to because you gotta like you gotta provide services to people. Yeah, totally. You know, like you're not just like having a product on a shelf. It's not like a it's not like a like a uh Starbucks where you know you have you just throw there'll be you have you know a hundred applicants that are waiting in the what in the on the on just to come and start with you, you know? Yeah. Um so you don't have those luxuries that some like for-profits do.
SPEAKER_00:That makes sense.
SPEAKER_02:Yeah.
SPEAKER_00:Yeah. And so kind of moving on to like kind of the broader picture here, you know, through your how long, how long have you been doing digital nest at this point? Eleven years, yeah. Yeah, that's it. Eleven years this month. Oh, congratulations. Um what obstacles have you hit as an organization where you've had to, you know, keep leading the ship, but it was pretty turbulent that you would consider turbulent. Have you had these moments? And if you had, like, what if can you explain to me, like, share kind of some wisdom that came out of them?
SPEAKER_02:Yeah, I think in the early days and like so like 2014 uh through 2016, we were like we came out of the gate and we came out pretty quick, and like we had a lot of support, you know. And then you hit like 27, 2018, where you're like you're hiring more people, and all of a sudden, like you know, a$25 check just doesn't go as far as it used to because you know, people are expensive. And so, you know, we've ran into like financial, like, oh no, like are we gonna be able to make it next month, you know? And we've like calling donors up and like, hey, you can you send that check you told me you're gonna send? You know, like yeah, uh we're fine, but can you just hurry up and send it? You know? Um, so we've run into that thing. And then, you know, like with COVID, you know, it it it was crazy, you know. Um, you know, we're place-based, we have these centers where young people come in and get access to technology and training and support and community, and all of a sudden you're saying, Okay, you can't come in, we're at a pivot online. Um, interestingly though, um it was a tough pivot, but I had all the I had a lot of tech talent.
unknown:Yeah.
SPEAKER_00:Oh, nice. Yeah, I just thought about that right now.
SPEAKER_02:Yeah, so we were we actually were able to like shift all of our classes online. We were reached out, we always like technical tools, and and then actually the schools started reaching out to us and asking us if they could help. And like we were we were literally having like recording, reading books, recording it, posting them on YouTube for like kindergarten teachers to like send to their kids at home so they could help learn. And we're doing virtual high school graduations, and we were like helping the school district in Salinas like bring online all their like portable. Hot spots and we were getting out in schools. We were helping small businesses. Like we build a website so small businesses that didn't have a web presence could like post their business hours so that you know they could do like you know, you could buy from them online and stuff. So we were I was telling my staff, like, look, just do whatever the community needs, and like if we go down, at least we can stay down and went down like helping, right? Um so it was a huge pivot for us. It was like a total change in what we're doing, but actually we actually that caused us to get more visibility. Yeah. And we actually had more, we actually grew substantially during COVID. Yeah. When a lot of organizations were going the other way, we were like growing and trying to hire folks. Yeah. Um, and then and then coming out of that, like the the next big challenge is like you have a whole generation of young people that were used to just being at home and being online. And now you're saying come back into a space and come back into community and engage. So we're just barely coming out of that. Right. You know, of like get you youth getting used to like coming back and being part of programs, you know?
SPEAKER_00:Ooh, man. So like with that obstacle of getting people back, like what what what lessons have you been learning with that?
SPEAKER_02:Yeah, just you know, we uh we have to get our staff in the schools and like really promote, you know. Prior to COVID, our centers were really kind of like uh a like we were like a beacon, like a magnet, you know, and then you have all these young people who are like go uh are hanging out and go to from school and they go straight home. Like, so they're not they're not like coming by your spot. So like we had to get our staff like in the schools, talking with youth, tabling, doing a lot more of that than we ever did pre-COVID, like for sure, you know.
SPEAKER_00:Yeah, I relate to that. I mean, um the mu the music school actually succeeded pretty heavily during COVID because we went online and then opened up the space and there was like social distancing and all that. Yeah. But I think that ironically the struggle was after COVID. Yeah, it's a trip.
SPEAKER_02:Like there's their behaviors are different. Yeah. And parents' behaviors are different, you know. Like they're just like they're just they're fine with their kids going home, yeah, and just being at home, you know. It's it's been a trip. And you know, it's also like 11 years, so like we're for from 2014 to 2020. Yeah, like we were trying a bunch of different things, things were like we were expanding. We opened Salinas in that time. The first time we expanded, and things were going, we were failing, and like things were working and were not working. And okay, we got the model, and then like COVID hit, and it's like 2020 to 2023, really, like like you're in the mix of like so like 2020, 2022, like you're gonna start coming out of it. So we're now in 2025, so it's like 2023, 2025. It's only been like really two years, yeah, two and a half, maybe three, of like our real program. Uh so it feels like in a lot of ways we're like new, you know?
SPEAKER_00:Yeah. I mean, like I I think I think, yeah. I mean, and I I think that's a good thing because also I feel like the it's it sounds like you're thinking of the long game, you know, that when 11 years feels like you're new, you know. Um yeah, obviously COVID, I feel like, uh, made everyone's sense of time kind of weird, you know. Um like I I don't even know. Like I sort of after 2020, it just gets weird for me. Like the sense of years. Yeah. You know, I'm like, was that really three years of that, you know? And it feels like one block or something, you know?
SPEAKER_02:I mean, people are judging time, but like, was that pre-COVID or post-code?
SPEAKER_00:Yeah, exactly. Did I get the before times? Um so um this kind of is more about how you function with your employees. So, you know, there's a lot of talk about transparency and you know, vulnerability and all these things, right? And so I'm wondering like, what is your strategy around like things like transparency, vulnerability, clarity, all that? And how do you interact and like hold on to information strategically or whatever? Like what do you like what's your what's your methodology here when when managing people?
SPEAKER_02:Yeah, you know, it's a trip. Um this is the stuff I really love, right? Like if you look at my business card, I don't have my title on it. Yeah, we don't allow anybody to put their titles on their business cards because we believe that anybody should be able to speak about the organization just because I'm the CEO. Like you should just come to me. Or so none of us have titles on our business cards. Yeah, none of us have an office. So my desk is the same as our office manager's desk. Yeah, like you you can't tell it apart, right? Like you saw our space and there, just a bunch of desks everywhere. I was like, wow, I'm just in the open here. You're all in the open, yeah. That's why we have these cards. I'm a little scared. Yeah, and like I can see what's on someone's screen. Yeah, you know, and they can see what's on my screen. Yeah, you know, so um, so we do things like that uh just to make sure that you know we're accessibility. Yeah, and I make sure all everybody on my on my executive team is like that's number one thing. You have to be accessible to everybody. Um, and then we do things like uh in terms of like transparency, like we have a monthly North Star meeting. So so we we have two uh really all-staff meetings every month. One is uh ask me anything. So they could come in and literally ask me anything they want. Um, and that's optional. Yeah, um uh and then we have a mandatory North Star meeting. So this is where are we going in the future? Yeah, you can't ask me about anything in the past. So you can't ask me like, why did we decide to do that? No, no, no. It's been done, it's in the past, we did it. But what what but here's what's coming? What questions do you have, what things are you curious about? As part of that, we 100% share all of our financials to all staff. So every single one of my staff can see, can read a a uh a budget versus actual spreadsheet, revenue, expense reports because we want them to see where we are as an organization in terms of financial health, right? And this is one of the main skill sets that we've seen, especially first generation professionals really struggle, is understanding financials. And so we need to train you all how to read financials and how to speak the basics around budget versus actual cash flow, things like that, months of revenue, months of cash on hand, so that when you leave here and you're in those environments, you can say, Oh yeah, I can read it, you know, I understand all this, I understand what expense expense reports are. Um so we share our financials with 100% with all of our staff. Um uh between those North Star meetings, I have executive because sometimes things happen between those North Stars that people can't ask me questions. Uh so I have an executive summary that goes out in between those meetings. Like, oh, you know, here's some major updates that have happened. Um everyone of our staff can uh set up meetings with anybody they want. Um uh so there's no you don't like I literally have some of our entry-level staff calendar invite me to go grab lunch or you know, sit down and have a 30-minute meeting thing. So we do that across the agency. Everybody's accessible. Um so things like that. Those are like the main things that come to mind. Um we have a staff summit every uh every winter. All we have two all staff where the we all come together, and it's a staff summit where we have two days of training, a lot of workshops, all different levels of staff present. Um, we have no titles. We're we mix up all the tables, so there's not all the executives in one table. And you know, so we it's all mixed up. We we pair everybody sp strategically so they can see other levels of like people's professional, like where they're on the professional journey. So we pair them up with lunch so they could like get to know some people and get to know each other. So we do a lot of things that are really intentional. Yeah, um, and the funny, the trippy thing is a lot of our especially like we have a lot of pr staff that this is their first professional job.
SPEAKER_01:Yeah.
SPEAKER_02:And they're like in the last three, two years, we've had eight people leave. Well, we've had more people leave, but eight of those people who have left thinking the grass is greener on the other side, have asked to come back. I kid you not.
SPEAKER_00:I mean, like the culture you're describing is is a pretty unique one, I would absolutely yeah, it's totally unique.
SPEAKER_02:And like we have you have two work from home days. Um, you know, we uh we yeah, we we get snacks for everybody here, you know, coffee. Yeah, you know.
SPEAKER_00:What is you know uh I mean I'm loving all of this.
SPEAKER_02:And you know what it's you know what it's at because the the what I tell people is we're investing in young people the way Silicon Valley invests in their employees. That means our people get the best. And as our young people get the best, that means our staff get the best.
SPEAKER_00:I mean, I love that. Have you have you seen success with this model, like in your organization, or have and what are some obstacles that have come up with this kind of methodology? Yeah, you know, like absolutely I can hear the benefits, but like, but you know, you could talk about that too.
SPEAKER_02:Well, it's it's yeah, so you know, it's funny, like uh people want more. Yeah. And and I want to get and I want to give it more. We want to get paid better. Okay, well, you know, we can we gotta, you know, it's cost of living, and we've been able to do a cost of living every year. Sometimes it's not as high as people want because we gotta like watch the budget. But I'm but I show them that in the financials. Like we're not hitting our revenue goals this year. Like, you know, we're struggling here these years, these months, and so we can't give you as much, but we're gonna give you some, you know, like so we're we're transparent with all that. So they understand the why. Yeah. Yeah. Um and and but uh but you know, we're pretty committed. Like we're our board has decided that we're gonna be in this uh in the 70th percentile of all Bay Area nonprofits in terms of compensation.
SPEAKER_00:Nice.
SPEAKER_02:Right. We're not there yet. We're we probably were like at the 60th percentile, but we're every year we're inching closer. Right. You know? Right. Uh so priority. Yeah. Yeah, and I think staff appreciate that. They're like, okay, we're not there yet. I see it, but we're you know, the the organization cares and they're trying, you know, and they're really working towards it. We're with next year we want to add on insurance coverage for dependents, and we're gonna start it off, or my hope is we're gonna start it off at 50% coverage and then 75% coverage and a hundred percent coverage. Like we're gonna inch our way to get there, you know. So we're doing it responsibly, um, but we're we're trying to improve, you know, for folks.
SPEAKER_00:So why why do you why don't you think more nonprofits have this kind of uh methodology?
SPEAKER_02:And yeah, yeah, I think it's it's costly, man. Like we have to raise a lot of money, right? Um, but uh um so I I I think it varies. Um that's a complex answer. So uh I just know the stats on on so on Latinos, but uh less than I think it's less than six percent of all executive directors are Latinos.
SPEAKER_01:Yeah.
SPEAKER_02:And we receive less than two percent of all philanthropic dollars. It's it's not much better with the black community. It's probably like it's like we're probably pretty cool close, you know, like very few black uh leaders, and they're not getting much of the money. You know, and so we are operating in communities that need a lot of support, and we're getting very little philanthropic support, and we're we're we're grow, we a lot of us grow up with scarcity and struggle. So monies, we have a really like complex relationship with money and asking people for money and asking people for help and making bold asks and asking for more what you need, you know, you know, and so I think that's why a lot of the nonprofits, especially nonprofits led by people of color, are really struggling because there's all these social like things that have been like we've been hit with for generations, that it's hard for us to ask for more money. It's hard for us to feel like we deserve more, and we haven't been able to bring in the resources needed to really thrive and help our organizations thrive.
SPEAKER_00:I mean, you just opened up a can there. Yeah, yeah, you know. Yeah, but it's true. I mean, like I think um that's been probably the most common theme I've heard, you know, is like is is a lot around the ask, right? And like feeling worthy of that or having insecurities around that. Well, it's funny, with like um I always, you know, since the one benefit of being on like I've been like on a ridiculous amount of boards, and the one benefit is that I've seen kind of like that, like what you're describing, this privilege, right? And I've seen people just like executive directors, just like you know, you white executive directors, like be able to just, you know, oh I'm just gonna ask for 5k. Like there's no no no like block around it, yeah. You know, and and just like do it and like get more and like just be able to fund and all these things. And it's something that I see a lot of people, like women or or people of color, or these folks who are in leadership, have a harder time doing, it seems.
SPEAKER_02:Um which I thought, which I think is very there's very few of us leading organizations, yeah. There's very and we're getting very few dollars.
SPEAKER_00:Yeah.
SPEAKER_02:So like we don't have the models of what it takes to rate, and and I think we are we lead with our hearts, yeah. We lead it, it's all about our community. And it's sometimes it's hard to think about going beyond your community. And I think sometimes to get look, the our community doesn't have the resources. Yeah. We have to look beyond our community to pull in the resources into our community. And I think that's that's a challenge, I think, for us too.
SPEAKER_00:Now you're speaking the speaking truth right now. Yeah, for real. Um definitely about and I think that's where that uh when I talk about courage or discomfort, right? You know, being able to go into those spaces where you maybe not feel you don't feel like you belong or you're uncomfortable or in doing it anyway. Yeah. Right. And I brought it, it helps the community in the long run, I believe. You know, if you if that's your intention, you know, which clearly that is yours.
SPEAKER_02:Yeah, and you know, a lot of people have helped me, I didn't, you know. Yeah. Like there's two people in this community that um uh have been were were the first people who to um coach me on how to make an ask. And that was Nina Simon and Sibley Simon. Nice. Uh so they when I launched Digital NAS, they Nina told me, Hey, hey, have you ever made an ask before? Have you asked people for money? I'm like, well, just only once, my first donor, but it was kind of like, you know, um, and never like sat against across from somebody who didn't really know me and asked them for money. She's like, Well, why don't you come over and we'll like let's practice, you know? And I like and I made an ask, and they're like, You gotta be bigger, like think bigger, think bolder, you know, like have that courage. And so like I think I've you know I've learned how to do it. Um I feel like I do it pretty well now. Um, but it's it's been an 11-year journey, you know, and it's like it's still very uncomfortable, you know.
SPEAKER_00:If you gotta coach somebody who's listening right now, what would you tell them how to make a good ask?
SPEAKER_02:Yeah, well, I mean, I think you gotta be bold. And and I think you gotta like if you if you need if you need$10,000, ask for$10,000. You know, if uh you ask for what you need, ask um uh really push people. They know what their capacity is. Like if they have big capacity, like be big and be bold, you know, be appreciative of everything you get, follow up with everybody, um, you know, you know, think uh, you know, use people's money resources wisely, but you gotta be bold, man, and that's hard.
SPEAKER_00:Yeah, I got a little feeling there when I when I keep saying that. Um okay, we're gonna transition a little bit here. Yeah. Um so what what's your deal when something tough happens? Like, are you are you someone who gets anxious? Uh are you are you someone who just like, oh, that doesn't affect me? I'm cool, like just figure out the facts on the ground, frustrated, angry. Like, what is your like when something like stressful happens, like what is your internal state like?
SPEAKER_02:Yeah, I didn't know that I got stressed until I went on a sabbatical.
SPEAKER_00:Okay.
SPEAKER_02:And it was a forced sabbatical. I was like, I didn't think I needed it, but it was a foundation approached me and said, hey, we got we're launching a sabbatical program. We now offer sabbaticals at the digital nest. Some somebody one of my staffs actually leaves, she leaves on Monday for six six weeks sabbatical, uh, because she's been here uh for a certain amount of time. But um, I didn't think I needed it. So the foundation came to me and was like, hey, uh we got you got this program. Like, no, no, I'm good. Like, no, no, you should do it. You know, we'll we'll fully fund it and we're gonna the organization's gonna get a pretty big grant. I'm like, okay, I'll do it for the NAS, you know?
SPEAKER_01:Yeah.
SPEAKER_02:Um, and then I went on the sabbatical, and you know, for ye for uh I'm a horrible sleeper.
SPEAKER_00:Yeah.
SPEAKER_02:And I but I didn't I always thought, oh, I just I don't sleep much, and I just that's just who I am.
SPEAKER_01:Yeah.
SPEAKER_02:And then when I went on sabbatical about two weeks into it, my leg pain started going away. And um I was my wife was telling me I wasn't tossing and turning as much in bed.
SPEAKER_01:Yeah.
SPEAKER_02:And I was getting longer sleep.
SPEAKER_01:Yeah.
SPEAKER_02:And I realized that my stress manifested in lack of sleep and like health. Yeah. Um, so I really have been like trying to be like and feeling like I need to rush out of the house, feeling I need to work late, feeling I need to be up on email first thing in the morning. And not only was it like finding out it was stressful on me, it was bringing a lot of stress to my staff.
SPEAKER_00:Yeah.
SPEAKER_02:Because they felt like they had to respond to me. Ah, yeah. Um, even though I'm like, oh, like I'm totally like your CEO, but I'm I'm laid back and I'm really transparent. Like, right. And my one of my one of my staff's like, yeah, but it doesn't matter. Like that you're still the CEO. Like they they don't, they don't they they know it's Jacob and he's like a really cool boss or whatever, but like you're still their boss. Yeah. And like realizing that I was doing that to them too. Um, so that was like stress for me when things get tough. Like I sleep poorly, and and so I just I have to be you have to be really intentional about taking care of yourself.
SPEAKER_00:So so yeah, that's that's a follow-up question. Like, what are some practices that you do to help like in this case take care of your stress and you know take care of your yourself so that you don't repeat that if possible.
SPEAKER_02:Yeah, I I um I used to leave the house uh by like 6 30 in the morning.
SPEAKER_01:Yeah.
SPEAKER_02:Um and now I don't I wake up my daughter uh for school. Yeah and I leave at 7 30. So just like and I and I don't I don't get online before 7 30.
SPEAKER_00:Oh nice.
SPEAKER_02:And uh just like being intentional about being there for my daughter and like making sure she sees me as I leave the door, like that slowed me down. Yeah, you know, so just that just that basic practice of like of slowing down. Um uh I I a mentor of mine told me uh to take the long way home.
SPEAKER_01:Yeah.
SPEAKER_02:And so, and it's hard to say, like you often feel like you've been working and like you want to get home as soon as you can, but like take the extra time to drive home a longer route because you could get you clear your mind, clear your mind, you know? And so you get home, you're fully home. Yeah, you're not like checking your device, you're not on the email, like uh, and I've seen like I've realized that the biggest stressful thing for me has often been feeling like I'm letting down my family or letting down my staff.
SPEAKER_00:Yeah.
SPEAKER_02:And so me by me slowing down is taking care of my family and taking care of my staff.
SPEAKER_00:Yeah.
SPEAKER_02:And um, so those those little things, I'm you know, trying to exercise more, yeah. Um trying to eat better, yeah. Um, things like that.
SPEAKER_00:Man, have you seen um positive effects?
SPEAKER_02:Yeah. Absolutely. I think you just like, yeah, like uh just feeling like I'm not things aren't that urgent, man. Just like feeling better, having more conversations with people.
SPEAKER_01:Yeah.
SPEAKER_02:And people not feeling like Jacob's like, here he comes with another idea, he's all nonstop. I gotta I gotta be on. Like, yeah, people are I've gotten really good feedback about it, even for my staff and my family.
SPEAKER_00:Yeah. All right. So I mean this is gonna be a good question for you right now. Because um, what is some of good advice that you can give uh emerging leaders who are listening in right now and people who are just getting into leadership, or maybe like playing with the idea of potentially getting into leadership? What is some like solid advice that you could give them right now?
SPEAKER_02:Yeah, if you if you want, like try to try to get close wherever you're working now, try to be in close proximity to leadership. So you can see the challenges that they face, you can see how they operate, good or bad. You could even like if there's a leader that you're working with that you don't like these behaviors, you could take that into your next leadership role and like say, I'm not gonna do that, right? Um, but just be as, and I tell this to my staff here too, like I know it's comfortable oftentimes to be with your friends and the people you're you know, your colleagues that you're really tight with, but like try to get close to leadership, you know, and try to be even just when there are conversations like like see if you could enter those conversations, ask your supervisor if you could be in on a meeting around financials or you know, fundraising, or just like try to create that um because you just learn like that's that was my challenge is that I wasn't close to leadership, so I didn't know what it meant to be a leader. And so um trying to learn how to be a leader. Um if you're interested in like starting your your own little venture, like work somewhere first and like see if that's what you really want to do. Um like my mentor say, take the long way home. Learning how to say no is a practice you gotta know. Like you got you gotta learn how to say no to things. Um you gotta learn how to make hard decisions and be okay with it and know that most people are not gonna like your decision. There's gonna be people you're gonna upset, you know, but you gotta if it's best for the if it's best for the youth and it's best for the organization, then I gotta make that call. You know, and sometimes you don't make the call because you don't wanna like be the bad guy with your with the employees, but like it's not about them. Like they're gonna move on, young people and the organizations is your top priority. So whatever your your mission is, like that's your priority. It's not the people that work there, you know. So that that's I for a long time I I didn't want to make anybody upset. I want to be everybody's friend. And you realize you just you just can't, like some people you gotta make decisions that some people aren't gonna like.
SPEAKER_00:Wise advice. Okay, so this next one is for like maybe seasoned leaders, people who are leading right now, or people who maybe come into leadership. Um, yeah, like what now that you've been in leadership, what is some like wisdom that you would think that other leaders need? You could you can visualize these people in your head if you want, you know?
SPEAKER_02:Yeah, I if I have my my leadership, my executive team, all those people on my team are smarter than me.
unknown:Yeah.
SPEAKER_02:Hands down. Like they're just brilliant, they're good at what they do, they um they're they're thoughtful, they they have the same values, but they're really brilliant people. And I think I'm I've been really I've um I've really tried to surround my people that are smarter than me. And you often hear that, like people say that's like good advice, but it's true, like it's it really makes it makes you a better leader, you know, because one, I'm not worried about a lot of the things that are happening on the day-to-day because I have good people leading it, and it frees me up to like to take on bigger tasks, to to talk with major, make more donors, to be out there in the community and meet more people. So I know the house is being being taken care of by some really amazing people. So hire amazing people, like let go of your ego. It's not about you. The digital nest is bigger than Jacob. Um, you know, right our for next year, one of our goals is they're developing secession plans for every one of every one of the staff. That includes me. I I could get hit by a bus tomorrow, and we need to have a plan for somebody to step in to take over the organization. And so a lot of, especially founders, I think, are really threatened by that, like thinking that they it has to be them to lead the organization. And I've I'm really uh I'm okay with like if something was to happen to me or my family and I had to like say, Hey, I gotta go because I got an emergency, I know this place would operate and thrive without me. And that's because I've just been able to bring in some amazing people.
SPEAKER_00:All right, Jacob. Um, so this is your time. If you want to say anything to the community or like give any words of wisdom, last words of wisdom. Um this is your this is your time to shine. Yeah, no, no pressure at all. Uh where can where can people find you?
SPEAKER_02:Yeah, you know, my my my my fundraising team will say, you know, make the ask, you know. Yeah. Uh so support the nest. No, um, but uh, you know, I always tell people, yeah, I need your donations, but I need you to hire our youth. And so for all the people listening, if you're looking for amazing talent, we got it. Like we have everything from software developers, content creation, content creators, marketing folks, uh, web designers, IT support. Like, you want talent, I got diverse, amazing, brilliant young people that are here. You know, so hire the hire youth from the nest. Um uh you can find us on all the socials. We we do and all a lot of our content is created by all of our youth. Our website is being is designed by our youth. Our end of the year campaign, all those videos are pushing out, the letters, all that is designed by our youth. Um, so follow us on socials. Um, you can find us online at digitalness.org. Um, you could shoot me an email, um, Jacob at digital nest.org. Love to connect, love to you know, talk and brainstorm and collaborate and partner and and and hopefully help a lot of young people and and help our communities.
SPEAKER_00:Jacob, it's been an honor having you on the podcast. Thank you so much. I've been waiting for this to I feel like um yeah, yeah.
SPEAKER_02:Some of them you've interviewed a lot of amazing people online. Come on, man. Yeah, over here. No, but no, they thanks for what you do. I think it's important. And I've listened to quite a few of your shows and I've learned a lot too from those leaders. And so thanks for creating space for this.
SPEAKER_00:No, man, it it's it's totally my honor. It's been a long time coming. Yeah, I appreciate you. Yeah, likewise. Yeah, this has been Speak for Change Podcast. I'm your host, Thomas Sage Petterson, and thank you so much for listening. Have a wonderful day.