E25: Bridging the Digital Divide with Olatunde Sobomehin

When families learn together, that increases retention, that increases your passion. When you learn together, everybody’s advancing exponentially because those conversations come home.”

- Olatunde Sobomehin

Episode Summary:

Community, character, and collaboration; these are three of the main values that form the foundation of Olatunde Sobomehin’s organization, StreetCode Academy. 

Despite his idea being turned down initially, Tunde refused to give up on his dream of making coding accessible and enjoyable for people of color, and he used an innovative strategy to garner interest in the subject, as you will hear about today. 

Technology is a pervasive force across the world and is used to enhance so many aspects of our lives, including our economic standing. People of color are often introduced to technology through a negative lens, resulting in a disadvantage. Through its community-based, family-centered, in-depth approach, StreetCode Academy sets itself apart from other organizations doing similar work and has experienced massive growth since its founding in 2014. 

Listen in today to gain insights into the factors that have made StreetCode Academy the success it is, the hopes that Tunde has for the organization’s future, and the organization’s refreshing approach to well-being! 

What You’ll Learn On This Episode:

  • [04:06] Tunde shares how his upbringing has influenced who he is today
  • [05:30] The pervasive power of technology
  • [07:16] A dream which turned into Tunde’s first business
  • [08:41] Growth that StreetCode Academy has experienced since its founding
  • [11:09] The community-based nature of StreetCode Academy
  • [12:03] How a negative introduction to technology can impact your life
  • [13:36] Value in the family-centered approach that StreetCode Academy had adopted
  • [14:16] Depth of the programs offered by StreetCode Academy
  • [18:05] Funding that got StreetCode Academy off the ground
  • [21:09] How StreetCode emphasizes employee wellbeing
  • [22:30] The dream of a for-profit arm of StreetCode
  • [25:59] Complementary skill sets of Tunde and his team members
  • [29:57] Tunde’s approach to relationship building and how it has benefited him
  • [34:30] The imbalance which motivated Tunde to take a sabbatical
  • [36:50] an vital lesson that Tunde learned about technology from his son
  • [37:17] How Tunde’s family has enhanced StreetCode
  • [39:27] What Tunde wishes he had known earlier

Resources Mentioned:

Connect With Us: 

Connect with Olatunde:



OS: We sometimes always tend to overvalue competence and we undervalue things like character and chemistry, which is really what sustained us. We take a look at who we had fundraising for our first five, six years. We didn’t have anybody who has skills in development or in fundraising. But what we did have were people who were going to come at it with incredible integrity and were going to work hard and be part of the team.”




[00:00:31] AW: You’re listening to the Transcend Podcast. I’m your host, Asha Wilkerson, an attorney by training and an educator at heart. This podcast is all about empowering you to build a business and leave a legacy. Here’s the thing, the wealth gap in America is consistently increasing and while full-time entrepreneurship is not for everyone, even a side hustle can change your financial landscape if you’re intentional about using your business to build wealth. I’ve run my own law firm for over 10 years, and in that time, I’ve helped countless California businesses go from idea to six figures. On this podcast, we talk about what it truly takes to build a sustainable business and find financial freedom. Let’s dive in.




[00:01:19] AW: Welcome back to Transcend the Podcast. I am again so excited and grateful that you are here today. I am really, really excited for today’s guest. I think I say that before every episode and I genuinely mean it. Olatunde Sobomehin is someone that I have known for probably about 20 years now, just about. If you can believe that. He is one of the co-founders of StreetCode Academy. He is here today to share with you his journey in entrepreneurship in the nonprofit space to create StreetCode Academy that has trained hundreds and thousands of individuals on how to code, and create apps, and games and things like that.


Tunde is the co-founder and CEO of StreetCode Academy, a community-based organization providing free tech education to communities of color. In addition to StreetCode Academy, Tunde has co-founded Esface, a youth sports and culture brand and Trillicon Valley, a lifestyle brand with products in technology, fashion and branding. He is a proud graduate of Stanford University. Together with his wife, Tamara, has four children, Olatayo, Temilola, Tatiola and Olataiye. Without further ado, tune in to our episode.




[00:02:34] AW: All right. Tunde Sobomehin, welcome to Transcend the Podcast. How are you doing today?


[00:02:39] OS: I’m beautiful. It’s Friday and it’s always great to be with you.


[00:02:42] AW: Thank you. Thank you. Well, I’m really excited to have you here, because I have known you for probably all of my adult life, actually, since we met when we were both in college but at different schools in Silicon Valley. I went to Santa Clara, you went to Stanford University, and of course met through your awesome brother, [Deli 00:03:01]. This is like – I mean, I realized I’ve been in the Bay for about 18, 19 years now, which is mind-blowing. For those of you listening, we also both grew up in Portland, so there’s a lot of synchronicity here. But it’s been an awesome tool IT here friendship between the two of us. Tunde is doing amazing, amazing work within the community and is one of the cofounders of StreetCode Academy in East Palo Alto. Can you tell us a little bit about what StreetCode is?


[00:03:32] OS: You’re going to have to – you can’t just say 20 years and throw back just all the history we have and not come back to that. That’s an incredible history. Thank you for putting it in context. We both grew up in Portland, but now call the Bay our home and it really is, because 20 years out here has made it our home. Portland will always, always be the roots, always be the home, but we have certainly grounded ourselves here. That was dope. Thank you for reminding me and all of us.


[00:03:59] AW: Of course.


[00:04:00] OS: All right. StreetCode, let me throw StreetCode back all the way to – connect it to those roots in Portland. Growing up in Portland, Oregon, being a part of what I think are some of the best programs in the country. At the time, I was part of Prospective Gents Club growing up, which is the African-based rites of passage program that had 100 black male youth involved in understanding spirituality, scholarship, cultural awareness, time management, time spent with positive adults, community service and respect. We were grounded in these real solid principles. I have mentors like Michael Chappie Grice, one of the best educators in the country. Has literally been the superintendent across the country. Has created programs for our communities to be educated. Has taught young kids how to fly aviation. I mean, these were the men that were seeding into me.


I came from a family that, you know, that cares about service. Both my mom and my father committed their lives to service. I brought all that with me and that was who I was coming into the Bay. Coming into Stanford University, which was to me, kind of advanced the scope I already was creating, right? In that part, in that expansion of the scope around how do you serve community in the best way? In my first two years at Stanford, I came across Jesse Jackson, who was doing a tour. He brought the message around digital divide to the Bay Area. This idea that the Fourth Civil Rights Movement, as he called it, was actually economic empowerment. It was like, we have the right to vote, we’re free from slavery, we’re legally integrated, and all those things are sorted, right?


But in terms of giving credit to the freedom fighters who fought and won those fights, it was like, “All right. Now, we have to fight and win this economic empowerment. We still don’t have access to the full sense of freedom, because we don’t have economics.” The key to the economics, as Jesse Jackson was calling it back in 1998, 1999, was technology. That was going to unlock people’s ability, because he saw in the broad sense of the term, or the broad sense of the idea that technology was going to impact every single aspect of our lives, right? So here we are on this podcast, you as a lawyer, me as a civil servant. We’re using technology to advance our work.


He saw that and was like, “Look, we need to be involved in that.” That captivated me, not because I was a technologist, because I was a community – I want to be like Dr. King. I want to advance the kind of mission that we – that’s where the seed for StreetCode kind of – I’m a co-founder, so there are plenty of other seeds of the people who came to it. But that was my seed, that was my first kind of like, “Wow!” I did some stuff at Stanford around that, working with prisoners. I went back to Portland and worked with juvenile, folks coming out of the system and teaching technology skills. We explored that whole recidivism path and how technology and access can help. Those were decades ago.


I went actually back to Portland, wanted to teach some high schoolers how to make websites. I wanted to walk down MLK Boulevard, knock on everybody’s door and say, “Do you have a website?” If they said, “No,” we say, “We can make one for you at a small fee.” I wanted to make money with teenagers, fellow teenagers my first summer back from college, and nobody wanted to go with me, there was nobody there. I had the computer cluster reserved. I knew the path we were going to do. I had a sense that this was going to really pop and be a good business and nobody wanted to spend their summer learning technology skills. Nobody wanted to spend their summer building websites. This is all part of like the time when we started to know each other.


Because the no’s of those students actually caused us to create Esface, which was to say, if you don’t see it now, let’s use fashion, athletics, community and entertainment to then wake us up to the possibilities of our future. We started doing the T-shirts, which you were around four. We started cutting hair, which you were around for. We started doing community events, which you were around for. The fashion, which you were around for.


Then seven years ago, after that big stint, and Deli is still running Esface, that idea around technology came back up. And it was like, “Okay. Now, the time is right.” People did want to spend their summers doing web design. People did want to spend their summers doing business. So now, we built from that same seed, StreetCode Academy, which now offers free technology classes, and we’ve grown from 20 students in that first class to serve over 3,000 last year.


[00:08:48] AW: Wow! That’s amazing. I want to touch on something that you said real quick, though, because you said that first summer you came back, you were knocking on doors and you kept hearing no, you kept hearing no, you kept hearing no. Many other people would have probably taken that no and said, “Okay, I don’t have a good idea. Forget it. Nobody wants to do it. Let’s pivot to the next thing or let’s drop this and go to the next thing.” But you didn’t drop it, you pivoted and said, “How can I talk to the audience that I want to talk to in a way that they can understand what I’m saying?” Essentially, you pivoted into the things that the community was looking for, fashion, and haircuts and community events so that you could reintroduce your original idea now with an audience that you have primed who is receptive to hear it.


I think that’s absolutely brilliant and genius, because so many of us give up on our goals before we even get started, but you had the foresight to say, “Okay. Maybe not right now, but let me do a few things to make sure that it gets ready and introduce it into the community in a way that is receptive.” Along that same line, like how is StreetCode different from, I don’t know, maybe some like coding academy that you would take, you know, like the Berkeley Extension or something else that has not come from you and your co-founders? How is it different?


[00:10:08] OS: Well, first, you’re such a gift to our world. I say that, I’m kind of emotional right now, because the way you just packaged StreetCode, and the way you just packaged kind of what I’ve done, was so beautiful. I just appreciate that. I’ve heard you talk about voting rights, or the elections, or the host of other things that you kind of share with our community. I just think our world is very fortunate to have you, as a voice, as a thought leader, as an educator. Really, I think at the core, you just break things down. Thank you for repeating back what I took 20 minutes to say. You said [inaudible 00:10:48]. Thank you.


[00:10:50] AW: Thank you for your words. You’re going to make me emotional.


[00:10:54] OS: Yeah. No, good. How are we different? Well, from Berkeley we’re way different. I’ll kind of zoom in to what makes us ultimately different. Maybe there’s three distinct ways. I think the first thing is that we’re community centered. Maybe I’ll say community-based. That’s interesting, because you walk onto Berkeley’s campus and for us, I didn’t realize this, but it’s, being black having pigmentation in our skin, that just automatically in America puts us at dis-ease. I mean, dis-ease, it’s kind of like, it’s harder to walk on some of these mainstream campuses and feel welcome, right? That’s just one big thing. Because we’re community-based, that means we’re going to be inside a community, presumably in a community that you know, trust and feel safe in and you have some connections too.


That’s one kind of obvious difference between a lot of different coding opportunities and ours. I’ll give you this one point, which I think you will love. This is the insight that came to us from a dude named Dimitri Sanders, but I think this is so phenomenal. Dimitri also grew up in Portland, shout out, and we grew up together. He identified this thing that I actually expressed to my family, but couldn’t recognize it, which is that most of us get an introduction to technology and it’s actually a negative introduction to technology.


Now, what am I trying to say? A lot of us focus on, “Okay, we just got to get our communities exposed. We got to get our communities introduced to technology.” We kind of like flat stop right there. I have kids, and so my job as a parent is to just introduce them to technology. But what Dimitri found was that, or introduced the idea that, hold on, introduction does not mean it’s a good thing. In fact, it could be a hurtful thing. Because how many of us were introduced to something, and because it was introduced in the wrong way, we never came back to it? We never returned to it. We call that a negative introduction to technology.


Let’s say your first introduction to technology was at this Berkeley Extension. I didn’t go to Berkeley. I didn’t do any Berkeley programs. In fact, the only Berkeley programs I know, shout out to Smash, were phenomenal. But let’s imagine that Berkeley was not able to make that a phenomenal experience for my son or daughter. Now, their first introduction to technology is actually bad, and it gives them a negative taste and negative experience. It doesn’t hook them. It doesn’t excite them. It doesn’t ignite passion. Then now, that’s worse.


The first thing that we do is we’re community based. I think that that’s going to give you a positive introduction to technology. That’s first. The second thing we’re different is that we’re family-centered. You have some very much community-based programs, but they focus only on high schoolers, or they focus only on middle schoolers, or they focus only on adult learners. Because we’re family based, we’re making that environment even more comfortable. We’re learning that when families learn together, that increases the retention, that increases your passion, that increases – then when you learn together, that now, everybody’s advancing exponentially, because those conversations come home. We have grandparents learning with grandkids. We have uncles with nieces and nephews, et cetera learning together. That’s the second thing I think is unique.


The third thing, I think is that we’re, we go deep into real technology. We’re talking about machine learning, and artificial intelligence, and blockchain and NFTs. We’re talking about the depth of technology as opposed to just the surface. So many of our programs focus simply on exposure, and don’t really go deep. The fact that we’re community-based, the fact that we’re family-centered, the fact that we go deep, I think makes us unique.


[00:14:45] AW: Right. I love those values. Assuming that you, maybe you call them values in the company, but I can see that those values are also apparent in you and also apparent in some of the other people that I’ve met from StreetCode. For those of you who are listening, thinking about bringing your values to the table and then adding sort of the business on top of that, right? Because the business is teaching children, not just children, everybody how to code, the whole family, the whole community. But you’re doing it in a way that is from the community of the community, serves the family to create these bonds, and then it just sort of permeates, right? Because now, the kids can talk to their parents or parents know what’s going on, they can bring their grandparents and their cousins, all of that stuff.


Then also, really teaching the coders to go deep in their knowledge. Instead of just introducing. There are a lot of things and programs that will teach us how to use technology, but not how to be developers of technology. Tying it back to what you said in the beginning, and Jesse Jackson’s message, and also my message about economic empowerment in the community, we have to learn how to do these things deeply, so we can be really, really good at them and then create whatever we need to create, instead of just being a really efficient user of the technology, or of the business services. We need to learn how to create that real intense understanding, so it just becomes a part of us. Because once you learn something, no one could ever take that away. You develop the skill, you keep developing it and your opportunities just open. I really appreciate that.


How did you all decide to become a nonprofit instead of being a for profit business? There are tons of people who have beautiful missions and want to serve the community and if they come to me, I have a real conversation about, nonprofits sound really good, but it’s not free. It’s not free money, right? You still have to figure out how to run the business, keep it afloat, pay the people who are working. You don’t want to be a part of that nonprofit scheme where we’re overtaxed and paying people peanuts, especially if you were trying to serve the black and brown community, because it’s not sustainable that way. Have you run it in a way that is sustaining for your employees as well as for the community? Because so many nonprofits do great work, but drain their employees, turnover is high, retention is low and frustrations are out of control.


[00:17:14] OS: Wow! Your questions are so on point. How many questions do you have? Because we’re going to be here a long time.


[00:17:22] AW: These are just off the cuff now.


[00:17:25] OS: Okay, all right. Wow! You had some crucial things, very timely. Let me see how I can get to these. First, you talked about this idea around being a nonprofit, not being free. What made us choose that? Well, we always knew that we wanted to be a for profit, nonprofit and an investment arm. That was part of the original concept. To your point, right, thinking about, let me backup, why is it important? Well, we knew that we couldn’t say it like you, we didn’t have the conviction. But we did know in the bottom of our hearts that nonprofits weren’t going to be able to fully connect us to the mission that Jesse Jackson was talking about economic empowerment. That’s not our key to economic empowerment.


If nonprofits are not going to really connect us fully, we can’t only do that. That can’t only be our vehicle. We have to do it in concert with the things that will. Things like access to capital is a big part of that. Thinking about, how can we funnel money our way? And then thinking about what how can we be a launching pad for businesses doing the things that you’re doing with your work? That was central. Like that’s like, we need those things.


Now, I didn’t know the Asha, at that time. For me, those people to help think about how to do, what to do, what vehicle, we didn’t have that and we didn’t have people who were – in fact, one of the reasons StreetCode was created was because we didn’t have people helping us create businesses in our community. We did not have those things that are needed. But given the landscape we were in, we said, “Now, how do we kickstart this? How do we do this effectively?” In Silicon Valley, because there is a relationship between tons of wealth being surrounding East Palo Alto and East Palo Alto had a need, especially in this technology education, nonprofit felt like a viable way to kind of kickstart that entire ecosystem.


There were people we knew, and we knew nonprofit, people that we knew that said, “Hey! I have a lot of money and I want communities to advance.” So I wanted this mission. So we started and we actually started with a very generous donation from the chief product officer of Facebook named Chris Cox, who gave us really a whole two year runway. That doesn’t happen often with nonprofits, and we were fortunate to do that. That’s a tremendous blessing. I don’t think we would have the path that we had had it not been. Shout out to Chris for being able to do sort of an unorthodox type of gift. Shout out to someone who saw a potential and really invested in that. That’s going to take, whether you’re for profit, nonprofit, we’re going to need people to invest in us in that kind of way. That was special.


Now. Fast forward to now. So yes, there’s a lot of work to fundraise. That could be a whole another podcast, just how do you fundraise for nonprofits, but that’s a real task. It’s not easy. But now that we’ve done that, we’ve grown our budget. We’re almost a $3 million-dollar organization. We’ve grown both in students served, in staff, in budget raised from that, kind of, first $300,000 budget, now $3 million. We kind of 10x the budget. We’ve grown staff members from being just three kind of part time and now we got 15 full-time people and 25 part-time and almost 100 volunteers that come through mentors.


We’ve certainly learned some things in that journey. But now we’re at a point where, where I’m at now, I’m on a sabbatical, I’m two weeks into a sabbatical. That sabbatical speaks to two things. One, it speaks to the burnout that you talked about. Especially in nonprofit, especially in mission where give our employees, starting with myself as the CEO, the investment, rest mentally, spiritually, to be able to sustain this work. We’ve always thought about how do we do that? We pay folks. We push to pay people as best we can in the nonprofit world. Because we know people are smart, they’re bringing ingenuity, they’re bringing passion, they’re bringing hard work, commitment. All the things that should be paid, they’re bringing that, and so we deserve that kind of payment too.


We’ve done that. We’ve tried to be very flexible in terms of our schedules, and give people, and be conscious of like the seasons. We’ve designed that, I feel lik,e in a way that’s thoughtful. But this sabbatical, I think, is sort of the biggest, boldest step. Is that we’re saying, let’s honor that work rest flow. Six days working, one day off. Six years working, one year off, that kind of thing. We’re putting that into practice. That’s one thing. Then the second thing about the sabbatical is that, from time away from StreetCode Academy, now, other things give birth. My board has tasked me, “Hey! Now that you’re taking some time off from the day to day operations of StreetCode Academy, give some time to the thought of StreetCode, Inc, which is the for profit.” Now, it gives us the ability to live into that dream, that not only are we going to be a nonprofit, we are also going to be a for profit, and what does that look like?


[00:22:48] AW: Right. Yeah. I think that’s beautifully stated, especially about the piece about rest. In our communities, we don’t do rest very well. Rest also oftentimes is a luxury. When you are building these businesses, whether nonprofit or for profit, really think about what do you need to recharge? What do you need to be sustainable? Because you can only go 100 miles an hour for so long. Vehicles run out of gas at some point. Humans run out of gas at some point. Building in that rest piece is super important.


That also speaks, I think, to the team that you have around you, to be able to feel comfortable stepping away and knowing that the operations are going to continue.




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[00:24:14] AW: So how did you build out the team around you? I mean, not going into nitty gritty details, but what were some of the big picture ideas? I tend to tell people, “Don’t duplicate your own skill set. You don’t need five of you. You need four other people who bring different skills to the table, because then you have more reach.” How did you think about putting people into place, especially in the beginning when it was in the idea phase? Who did you know or think to reach out to and why?


[00:24:43] OS: Wow! You have a lot of these thoughts and you’re helping us as entrepreneurs reach our dreams. I appreciate all the input and the feedback that you’re giving us as entrepreneurs. For me, the word that I can’t kick is trust, and is probably overstated and such a broad word. Let me try to give you a little detail into what I mean. The first thing is that, when we start StreetCode, we had to continually make a decision between – my brother says, “Character and chemistry over competence.” I love that and he’s given us that. Because it basically is like, we sometimes always tend to overvalue competence and we undervalue things like character and chemistry, which is really what sustained us. We take a look at who we had fund raising for our first five, six years. We didn’t have anybody who has skills in development or in fundraising. But what we did have with people who were going to come at it with incredible integrity and we’re going to work hard and be part of the team. Do what it takes to be part of the team. We had that same piece with the operations.


Now, we did have varying skills, right? I was somebody who lived in vision. I was somebody who lived directly with community. We had Frederick Alexandria as a co-founder. We started the program with my brother, Justin Phipps, my sister, Heather Starnes, David Chapman. There were others that kind of started as a program. But then we had to create this as an organization. When we sat around the table and had to fill out that IRS tax stuff, there were people who really knew how to fill those things out. That was Jasmine. She’s been our operating officer and she’s now interim CEO. She was an event planner at the time, like she was good with details, she knew how to follow through.


For me, I kind of lived in vision. There were things that wouldn’t always get taken care of or wouldn’t always – the loops wouldn’t always connect, because I’m constantly moving and thinking about vision. They allowed me to do that, while they kind of helped connect the dots. Frederick was phenomenal in campaigns, he’s phenomenal in messaging, he was phenomenal in brand and kind of storytelling. All these people come to the table. Tamara, my wife, had a background in education and operations. She brought that experience about, what kind of model are we going to bring? What kind of organization are we going to set up? She’s thinking long term. She’s thinking operationally.


Then Squint, was another person who had social capital, knew community, knew how to tell stories, et cetera. We had all those people kind of come to the table and think about how do we build this organization? Then we had board and board played their part, because they had different capacities. It speaks to like the different pieces playing their part to make the whole. But the last thing I’ll say about trust, is that it wasn’t easy and it’s not easy. I’m two weeks in, right? It’s not easy stepping away from the organization as the founding and current CEO. How do you take those? I hold a lot of work. I do a lot of – I have a lot of experience in this. Taking me away from the table leaves things that we could try to assume, but also leaves things that we just don’t know. It has pulled on my ability to trust my team and ultimately, trust God, if I was going to be 100% honest, because ultimately, I’m saying, “God, I believe that it’s you doing this work through us. That it’s not me doing the work on my own.”


That is the primary part of trust for me. And then I have to say, “God, I know you can use Jasmine, Tam, Frederick, Squint, Aaron, Stephanie, Jesus, the rest. I know you can use these folks too, just like you’ve used me and let me trust them in that process.” It’s not easy, but I think it is valuable because it allows us to recharge. It allows us to step back. We’re calling my sabbatical a step back to level up. Now, if I’m stepping back, a lot of people are leveling up. The organization levels up, the mission levels up and so do I. I get to recharge. That’s where we’re at.


[00:28:51]AW: Yeah, that’s awesome. Let’s talk about the power of relationships real quick. Because I know that you and your wife, Tam, met in college, right? You’re working together now. I know a number of the people who are surrounding StreetCode, whether they’re actually in the organization, or connected to the organization and supporting them, are people you have known for a number of years. I think we tend to underestimate the power of developing genuine relationships. Oftentimes, we think, “Oh, well, I need something now, so let me cultivate a relationship.” But can you speak to how relationships have helped you build this organization and also supported you maybe individually as the CEO of the organization?


[00:29:31] OS: Wow! You’re going to make me tear up. I’ve never been asked these kinds of questions. You got to forgive my pause. But these are not things that I knew, right? These are not things that I knew, “Okay, let me let me develop these relationships, with you, for example, over 20 years.” And now, when I have a legal question, I could call you up. I didn’t know. But I think this speaks to kind of what Deli is talking about with character and chemistry over competence.


What Deli is saying is over the long haul, I want to bank on character being something that’s going to take us further than anything else, and takes us farther than just that competence. I think that’s kind of how I approach relationships. I never thought that relationships were going to be – I just loved working with people who I trusted and who I believed in and who I loved, right? I’m going to call you first. I wanted you to be our lawyer, right? That was – you eventually connect us to another one. But that was like, because I like you and I like working with you. That’s kind of how I approached it. It was very self-centered in that way. I was like, I want to work with people who I enjoy. We’ve been able to do that, and that’s enjoyable to me. Like this whole family business kind of idea, that’s kind of my dream.


We co-founded Esface with Deli, and with Tim, and with Ebrahim, and [inaudible 00:30:58]. These are my family. You know what I’m saying? This are my family.


[00:31:00] AW: The OGs in my mind.


[00:31:03] OS: The OGs. Certainly the OGs. Johnny’s an attorney, Ebrahim’s a doctor, Deli is running Esface. They’re OGs, Now, because we have that – now, my dad is going through something, I’m calling Ebrahim. He’s a co-founder of Esface, whatever, we go back 20 years. But now, he’s a medical doctor and is able to help me. You know what I’m saying? Those relationships, but I think it’s also just character. At the end of the day, what I want is to make God happy with how I live my life. It forces me to kind of focus on my character.


Then what we see on the flip side of that is there’s return on that. There’s a return on that, okay, I’m able to build a family. Now, I’m able to try to build one brick at a time, one day at a time of marriage. Now, I’m able to build a business one brick at a time, one day at a time. At the center of all that is just me trying to work on my character and that is a focus in and of itself.


[00:32:06] AW: Yeah. I think that’s an extremely important point. It starts with us and it shoots out from there. Because then, when you have real relationships with people, people are also willing to leverage their own relationships to help you. For example, when you were asking – you’re writing a book, which is amazing. That’s not the kind of thing that I – that’s not the area of law that I practice, but I was able to connect you to someone else that I also love and adore and who is a [inaudible 00:32:34] attorney, and it’s because of both my relationship with both of y’all, now y’all have a relationship that is fruitful and getting you to where you need to go. And it is also enjoyable, because there’s chemistry and character, like Deli so artfully said.


I agree. You don’t always need someone who’s the most skilled, necessarily. But connect with people who are fitting within the value ecosystem that you have because that’s going to take you much further. Skills, you can learn. Character, you could change a little bit, but that chemistry, that’s also really, really important in business. I really appreciate that.


A couple more questions. How do you balance? Because you’ve got four beautiful children, you’ve got an awesome wife who I absolutely adore. You’ve also got Deli, you’ve got Remi. Those are both of your brothers who are in the Bay. Remi’s got two kids himself. Your family is huge, and dynamic and awesome. How do you balance running this business and also being present and accountable to the family? I say that because I think a lot of people think you could do one or the other. I’ve heard so many people, I think especially guys who –let me not stereotype, but I have heard multiple men feel like you’ve got to get this business thing, the financial thing, and that family is a distraction from that. But from the outside looking in, it seems like you have been able to integrate, because the family has always been there. I admire the way that you integrate family and business in this entire ecosystem. How do you do that? What do you think about that? How do you balance that?


[00:34:13] OS: Wow! These questions. Okay. Thank you for those kind words. I feel the same way about my family. I feel fortunate to be a part of the family I have, so I appreciate that. One, let me just acknowledge that I don’t balance that in the way I wish to balance it. Part of the reason for this sabbatical was my acknowledgement that my support of Tam as my partner, as my wife, was very much imbalanced. It will take a lot of years for us to kind of re-sculpt that balance, but me taking a sabbatical as she pursues her PhD is one way to kind of try to level that out. Similarly, with the kids, right? Because it flies by and so now, I feel like our kids are on their way out towards college, so I want that time. That sabbatical will help me kind of level out.


I think one of the compelling arguments for the sabbatical was this idea of save and kind of put in work for six years, and in that seventh year pour back in and save. The idea of somebody who’s like, “Man, I can’t. How would I ever be able to do that?” Well, the brother, Andy Crouch, who kind of seeded the idea of a sabbatical for me said, “We understand save and rest. It’s called retirement. We save all this money over time and then we hope that we retire at the end.” But why retire when I’m 70 years old, 65 years old, my kids are grown? Why not distribute that saving and rest while my kids are still with me, right?


I get to like, this morning, when I drove my kid to work, when I drove my son to school, I was able to just witness, we had 40 minutes in the car, it was completely silent. I just was able to listen to him eat an orange, read his book, and I just was admiring my son for 40 minutes. That kind of time without me thinking about work, without me thinking about everything like just to be there, that’s valuable. I’m grateful. I’m trying to learn how to balance those.


But to the brothers, or to the sisters or to whomever was thinking like, “Man, these families are going to be a distraction.” I don’t agree with it, and I understand it and I’m not mad at the logic. I’m not mad at – if my kid said that, I would give them my point and I would support it. But I do think that my perspective has been, and my experience has been, know that family has been integral. StreetCode would not be family based if it wasn’t for my son, Tayo.


My son, Tayo, at nine years old learned how to code, 11 years old built a game, got flown to Saudi Arabia, Tam, myself and him so that he could speak to the Saudi Arabian youth about technology. It opened up my eyes that, no, technology is not just for 16 to 24-year-olds, which is what we were doing originally. It opened up my mind, when every time I do something at StreetCode, I’m asking them, “How do y’all feel about that?”


I’m going to be a worse CEO at StreetCode with them out of the house. I’m just getting – practical thing, my profession is – yes, it’s hard to stop your day at 3:30 to go pick up a kid or your Saturdays or taking them to soccer games. But I’ve met people at soccer games that have helped me with StreetCode. The supporters of StreetCode are largely people that I know from my kids’ schools. It’s advanced. I think we need to chase what’s important to us first, and if family is that then do that, and trust that those things can be built on top of that. That speaks to your – I think you probably will say it better, but just how you build those values first, and then you build on top of those values. Family is that.


[00:38:05] AW: Yeah, I love it. I love it. All right. Last question for you. Well, second to the last question. What is one piece of advice, it doesn’t have to be the best piece, but the piece of advice you can think of right now for black and brown entrepreneurs who are looking to build a business and leave a legacy? It could be something that you wish you would have known before you started or just whatever you think a really good piece of advice is.


[00:38:28] OS: Okay, that’s good. I like the piece I wish I would have known. I’ll tell you what came to my mind first and see if your second sub question changes it. My first thing was going to be around those values and sort of trusting those values and building on top of those. I think I’m in the middle of that and I’ve tried to practice that various times. Do I think, whether it’s be – it’s been very practical in that, “Do I want to let this person go, who’s been phenomenal in ABCDEFG, but I don’t think they’re right for us?” That may make me look like a very poor decision maker, but I’ve trusted my own value. Or whether it be hiring somebody who may not have experience, but you feel like this person is that same kind of dynamic. I’m trusting my own values. I’m constantly working on my own values. If I was an entrepreneur, I would want to say that.


Now, the advice I wish I would have known early on is, I wish I would have known that investing in the people around me benefits me. I start off thinking it was very much about me, what I need to know, what I need to learn, what I need to be good at. I wish I would have been more supportive of investing in my kids. in my wife, Tam, in the people around me earlier. I know that, I’ve built a conviction around that now, but I think earlier – investing in them would have only made me stronger earlier. That’s a piece of advice I wish I would have known earlier.


[00:40:07] AW: I love it. I love it. I love it. Thank you so much, Tunde, for spending your Friday morning. I don’t know when you all are listening to this, but we are recording on a Friday morning on your sabbatical. I appreciate that you’re spending a little bit of your free time, or your newly distributed, newly assigned time with me this morning as we’re recording. If people want to get connected with StreetCode Academy or connect with you, what are the channels that they can do that through?


[00:40:36] OS: Our website is the best kind of central piece. www.streetcode.org is our website and we’re on all the social platforms, so they can follow us there too.


[00:40:44] AW: Perfect. Thank you so much.


[00:40:46] OS: Thank you, Asha.




[00:40:51] AW: Hey, there. Thanks for listening. I really hope that you enjoyed the episode this week. I am so so grateful to have you here and I hope that you are ready and feeling empowered to build your own business. You are needed, you are important and I want to support you. So, if you have just started a new business and you’re not sure what to do next, I’ve got a great checklist for you to download called the New Business Checklist. Head on over to transcendthemembership.com/slash checklist and put your name and your email into the box and you’ll get the checklist instantly.


Also, I want to ask you one more favor, if you want to interact with me on a daily basis, head on over to Instagram and follow my account @ashawilkersonesq on IG. I post on there daily. Can’t wait to answer your questions and begin the conversation. Talk to you soon.



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