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Thought Leadership and the Creative Hustle | Sam Seidel & Olatunde Sobomehin

Thought Leadership and the Creative Hustle | Sam Seidel & Olatunde Sobomehin | 452

Discovering your creative side and exploring the ambition to bring it to life.

An interview with Sam Seidel & Olatunde Sobomehin about co-authoring and exploring where the book will take them next.

Many professionals end up in a career that might not represent their passion or the bigger purpose they might want out of life.
So what do you do then?

To explore how to discover your purpose and find the ambition to go from idea to reality, I’ve invited Sam Seidel and Olatunde Sobomehin to share their thoughts with us. Sam Seidel is the Director of Strategy and Research at the Stanford and author of Hip Hop Genius: Remixing High School Education, which introduces an iteration of hip-hop education that goes far beyond studying music as classroom content.

Olatunde Sobomehin is the CEO and Co-Founder of StreetCode Academy, a nonprofit that helps bridge the digital divide, empowering communities of color to achieve their full potential by teaching the mindset, skills, and strategies they need to embrace tech and innovation.

Earlier this year, Sam and Olatunde co-authored Creative Hustle: Blaze Your Own Path and Make Work That Matters.

We begin our conversation discussing their book, which began as a course taught by Sam and Olatunde at the In the course, they taught about ways to identify and navigate your creative path, and how to make a living doing things that matter. It wasn’t until co-workers approached them and presented the idea of turning the course into a book that they realized the direction had greater potential.

Sam and Olatunde explain how the words “Creative Hustle” are perfect for their endeavor; a combination of imagination and ambition. They want to share insights about finding new creative paths that inspire, building diverse viewpoints, and creating ventures that benefit yourself and your community, while bringing enough entrepreneurial energy to move those ideas forward.

In addition, we discuss the journey of co-authoring the book, which is often a tumultuous road. Sam shares how the experience of having a co-author is preferred to writing solo and how the experience bought him so much closer to Olatunde.

Three Key Takeaways:
  • When authoring a book, you should also be considering the business models that can be used once it is published to avoid chasing the hype.
  • Working with a co-author allows you to push each other to be better and make sure your ideas are concrete.
  • During the process of writing a book, take some time to enjoy the process.

If you need a strategy to bring your thought leadership to market, Thought Leadership Leverage can assist you! Contact us for more information. In addition, we can help you implement marketing, research, and sales. Let us help you so you can devote yourself to what you do best.



Peter Winick And welcome, welcome, welcome. This is Peter Winick. I’m the founder and CEO at Thought Leadership Leverage. And you’re joining us on the podcast today, which is Leveraging Thought Leadership. So today we’re doing something that we typically don’t do, which is we’ve got two authors for the price of one, so we’ve got some coauthors on today. Sam Seidel is the director of strategy and research at the Stanford School K12 Lab and the author of Hip Hop Genius Remixing High School Education; and Olatunde Sobomehin is CEO and co-founder of Street Code Academy, a nonprofit that offers free tech classes to communities of color. He’s a graduate of Stanford. He’s an entrepreneur and an educator who has taught classes at the Stanford Haas Center at the And they both just co-wrote a book together called Creative Hustle, which is published by Stanford

Peter Winick So welcome aboard, gents. Let’s start here. What was the light bulb that went on and who called who and said, Hey, dude, I want to write a book. Who’s the guilty party?

Sam Seidel We have to give credit, I think, to our friend and colleague Scott Dawley and his coconspirator on the book series from the, Charlotte Fergus Aubrey, who actually were the ones who made that call. They hit us up. We had we had taught a course at the school called Creative Hustle. I think it’s fair to say, and you can correct me if I’m wrong, and you had a secret mission that you had never mentioned. But I think it’s fair to say that neither of us knew this was a book until the call from Scott. And he said he and Charlotte had been talking about it and they thought there was a book and what we had done with the class. And that was the beginning.

Olatunde Sobomehin And the genesis, though I think a light bulb went off when, you know, Sam and I both shared this, equally share the passion of bringing together minds from our community of East Palo Alto, which is across the freeway from Stanford University, and Stanford University, right where there’s a divide and often a misnomer that those communities are different. We both understand and know there’s a lot of similarities, especially when it comes to the ambition and drive. And so we said, Let’s do some together. We can’t. That was a call that we kind of both share. We had tried several times to make it work when we got together and said, Hey, this is the time we can actually do this. Creative Hustle was a word that that kind of we landed on the whiteboard of that session and we said, Let’s do a class where we bring them together and figure out unorthodox paths that everybody, whether you, Stanford, or whether you’re across the freeway, they’ll have to pay. And let’s do it. Let’s do a class exploring this topic.

Peter Winick So if we go back a little bit. Right. So Hustle’s been out there for a while as a term. Right. And typically it’s your side hustle or hustle and grind or I’m old enough to remember do the hustle, but we won’t go there depending on how to go. But how are you defining it –

Sam Seidel It’s too bad this is audio only, or we would have asked you to demonstrate.

Peter Winick That would be the only way I would say audio and I would imagine most of the listeners would need to Google “what is the hustle” and it’s there’s a lot of bellbottoms and anyway whatever. So how are you defining creative hustle?

Sam Seidel We’re defining it as the combination of imagination and ambition. Right. So on the creative side, it’s like, how can we think about an envision new paths, new worlds, new lives for ourselves, new ventures for ourselves and our colleagues and communities. And then the hustle component is how do we make those things happen? How do we how do we put the ambitious energy, the entrepreneurial energy behind those creative ideas and move them forward in the world?

Peter Winick Wouldn’t. I would argue a bit that most creatives the hustle comes more naturally to them. Right. You know, you don’t apply for a job as an artist or this or that or whatever in order to be successful as a creative. I think there’s a level of hustle that that’s part of the process, right? That’s part of the vibe.

Sam Seidel I might argue those are the creatives that you hear about because they’re the ones who were able to get their work out there. I think a lot of us may have a creative side that we don’t we don’t give that oxygen. We don’t put that engine behind. And we may we may follow a path that’s been a little more set for us that we’re told, oh, there’s a career over here. So we may chase after that or pursue that or find ourselves there by default. And there may be creative aspects of our lives, of our work that doesn’t get that same fuel in its tank. But I’d love to hear your thoughts on that, too, today. If you have if you have other thoughts about the notion that creatives are inherently more ambitious or entrepreneurial.

Olatunde Sobomehin No, I think I think, you know, the what I think about when I think about creative hustle. And Sam, you spoke to a beautifully but I like I like our subline, right. “Blaze your own path and make work that matters.” I think a lot of times hustle is often talked about with survival, is talking about money, is talking about kind of getting from A to B, but we don’t think about A to infinity. What is what is that what is that big thing I’m going to do in the world? The world that makes me what’s my purpose and how do I sort of make that happen? And so if you think about it and that way, all of us are creatives and we have this amazing but not abnormal idea of like, you know, you’re going to you go in a room of third graders, you ask, who’s creative? Everybody’s hand goes up. You go in a room with 30 year old as a you know, who’s creative. Barely a few hands go up. Right. So this this book is not necessarily for people who identify as creatives. This book is for people who want to make meaning. And then we ask you to identify as a creative right. We’re all creatives in that way.

Peter Winick So yeah. So, you know, as you were saying that one day I started thinking about. Sort of Maslow meets the hustle, right? So there’s a level like when you think about way back, calling someone a hustler wasn’t a compliment, right? It was typically synonymous with, you know, something shady, pickpocket, whatever. But now so I think going back to a trend is that there’s a level of hustle that’s like survival hustle. You got to do what you got to do to survive. So is Creative Hustle sort of ran parallel to Maslow, like a higher level of hustle. As beautiful.

Olatunde Sobomehin To me. I’m ready with that. That’s it. That’s it. There’s no seriously. I mean, we’ve had a lot of questions about side hustle versus creative hustle. Right. And while we all recognize side hustles have been a part of our lives. Side hustles, you know, it’s going to be a part of our life. And there’s no knock on side hustle. But this you’re right. This Maslow hierarchy, right there is something at the top of that is talking about making meaning. And I think the book tries to play in the both and. Right. So we try to understand, hey, creative hustle is that side hustle that allows you to survive in a world that needs you to pay bills. And it’s also how does that connect to this? Bigger purpose is bigger life goes is bigger meaning that you have in your life.

Peter Winick But until you get that baseline survival stuff, you really limited cognitively in every way else to really get into that creative space where the next meal is, the heat getting turned off or whatever.

Sam Seidel And that’s why we say right at the beginning of the book, we have a kind of a heading that says this book is. And then in parentheses it says, not about helping you make money or something like that. Because on the one hand, that is not what woke us up every day to work on this book is like, we want this get rich quick scheme for our readers or.

Peter Winick We like that I’m out. So you don’t you don’t get rich writing a book. We’ve never talked about it. What is it? The path to fame and fortune that everybody thinks it is. Hold on.

Sam Seidel I’m sorry. Sorry to be the ones to burst your bubble if you’ve been holding on to that this whole time.

Peter Winick What? I really get depressed. Guys do the math on how many hours you put in and the any form of compensation you’ve gotten. And it’s actually more lucrative to get a job in a clothing factory in Vietnam. When you think about.

Sam Seidel And I learned this on my first book and I learned well, what I learned was don’t do the math. Just that’s not that’s not why we’re doing it. That’s not what we got into it for. But, you know, I think going back to the parentheses, they speak to the reality that you were just speaking to, which is it’s a very privileged position that only a very few people get to be a that you don’t have to think about that. You don’t think about how you’re going to support yourself and your family. So we both don’t want that to be the be all, end all and don’t see that that’s not really creative hustle or what it’s about. And at the same time, if that’s nowhere in the equation, I think we’re letting folks down and we’re limiting our audience of who can really engage with and enjoy these lessons to a very small number of people with inherited wealth or whoever earned a lot already through their venture. And that’s definitely not who we set out. Not that we those folks shouldn’t find value in the book, but we want to write something that could be useful for folks from any walk of life at any point in their career or their journey. So we have to we have to engage with the fact that there’s financial realities that folks are dealing with. So that’s why we say it in that way with the parentheses there, it isn’t about making money, but we also recognize it has to be a little bit about making money at the same time.

Peter Winick If you’re enjoying this episode of Leveraging Thought Leadership, please make sure to subscribe. If you’d like to help spread the word about our podcast, please leave us a review and share it with your friends. We’re available on Apple Podcasts and on all major listening apps as well as at

Peter Winick So, you know, and on that piece on the financial reality, what, if any, I mean, there’s lots of reasons people write books, right? Hey, we you know, the two of us always want to write a book together. It’s a fortune mechanism to get your thinking paid to codify in the case of your book, there’s so many people in here interviewing people, developing relationships. Is there a business model? For you guys in terms of coming out of the book or what’s next or speaking, consulting, advising some of the typical. Typical Stanford School type things or what’s on the horizon.

Olatunde Sobomehin I think I think what’s fun about creative hustle and what’s fun about this journey for us as we explore our creative hustle is that. We get to start with the big meaning and then we find business models along that way that are really exciting, right? And so I just wanted a moment to speak directly, humbly to the folks that, you know, are worried about, the bills that are worried about the heat. And I think what I’ve gathered right as I’ve been in my own relative journey of moments like that. Is that how we try to highlight, you know, folks in this book and also throughout our work in our life that have made it through that moment. And one of the things that have made it through that moment is their eyes are on this bigger dream. The eyes are on this bigger meaning. And so it helps you get through. Similarly, surprisingly, people with a lot of money, people with a lot of opportunity. Very few take the time to think about what is that big next step. I remember when I first met with you, Peter, when we first got on the line with you and you were helping us think through what are your goals beyond this book? What are we that we don’t oftentimes, few of us get a chance to do that, and this book helps you think about that. So Sam and I, we’re extremely connected, like, right, right. In the sense of we both know that we want to lead this earth, blessing the people around us and leaving a mark for the next generation to be better right now. A book came out of that. A class came out of that. Now we’re exploring. Are we go do are we going do many documentary series? Are we going to do our own podcast? Are we going to do another book? Are we going to do workshops across the world? Right. These are all things where now we can play with business models, but we’re grounded by that principle and that North Star and that all is, you know, lines up. But what we put in the book. So I don’t the short answer is I don’t know exactly what the business model is going to be, but we’re having a lot of fun exploring what that is.

Peter Winick Yeah. And you know, to me in my work, the creativity is more often or as often in the business model as it is in the development of the thought leadership in the content, because there are some, quote, traditional things. You can go be a speaker, you can, you know, be an advisor, be a consult. But there’s so many cool different things that you can do today with your work that we never had chances for before. You know, everything is global. You can license it. There’s nothing in the book that’s not a universal concept. It might resonate more in certain cultures than others. So I think there’s as much creativity to be applied towards what’s our business model or models, and what do we want to do and how do we want to do it? Documentary is great. You know, that’s like an interesting piece, typically not the world’s greatest, most lucrative business models. If you do the math, you know, you know.

Olatunde Sobomehin How to make the money. You the mess.

Sam Seidel With that you get.

Peter Winick Exactly. Exactly. So let me ask you another thing. So writing a book together, there’s sort of this unspoken. Call it a bias or whatever in the publishing world where, oh, jeez. “Coauthors,” that’s a nightmare, right? Because it’s bad enough for a publisher to have to manage one crazy, never meet a deadline. Exponentially worse with two, because now there’s mood swings and this one doesn’t get along with that one or that one thought. This one’s doing this one. I don’t think you guys have killed each other. I don’t think we would we would have been like I would have been wanting to learn about each other on the other side.

Sam Seidel We would have been the world’s most boring reality show. You know, like everyone watches these reality shows to see the characters fall apart and fight each other. Like we really have never had have had that energy or that moment. And I guess a couple of things I can say on that front. I love the question. Thank you for asking about it. It’s been the biggest gift of this book personally has been the relationship with today and just the brotherhood that we’ve developed and the ways that we can become part of each other’s lives and communities and families. So, first of all, it’s been it’s been the biggest gift of the process for me. One thing I’ll say is I wrote a book, as you mentioned, 11 years ago now by myself. It was a painful experience. It was a lonely experience. It was a beautiful experience. I learned a lot about myself. I learned a lot about writing. I learned a lot about a lot of things. But getting to coauthor, I don’t know that I ever want to go back. And in fact, this is Creative Hustle is one of, I think, four books I’ve been working on over these last couple of years, all of which are coauthored and all of which so far have been great experiences. So I recommend it. And I say to all the publishers listening, don’t be so scared of it. It’s a great thing. And I think it pushed me to be better and better in terms of how I showed up to this process because I didn’t want to disappoint Tuesday. And it was just fun. I just I just looked forward to the one the one other, like, kind of pro-tip from what we did that I’ll share is we started every session, every writing session together, every work session by setting intentions and by sight, verbally speaking out, what our intentions were in that moment, in that next 2 hours we had, or whatever the time period was, and more broadly, like, what are we trying to do here? And verbalizing that? And that was an extremely I think we would have been great even without that, I think we would have gotten along great. But to come with a product we are proud of, but man, was that a powerful activity? And we’ve actually done that with our classes and some workshops we’ve run. Like we try to always build in that time meetings with our teams around this work. We’ve tried to carry that forward because it was it was such a powerful part of the way that we work together.

Peter Winick Very cool. How would you respond to that? Did you did you get as much joy as Sam did or.

Olatunde Sobomehin I was gonna say this. You know, you can see my screen right now. You would. You would see a copy of the hip hop genius behind me. Hip hop genius, the phenomenal book. Right? So that’s number one. You got four books coming out. So you got four coauthors. Everything’s great, Rosie. And those books are going to be phenomenal. The common denominator is my brother Sam’s idea. We got a great collaborator, writer. And so for any publishers out there, if Sam’s right, there was a valve you had at drama. You has some good writing, you know, and you guys, you have a good chemistry. So I can’t I mean, I would just double click on everything he said. Everything he said it’s been has been mutual.

Peter Winick Very cool. Thank you. So as we start to wrap up here. What would be the thoughts that you would share with either someone in situations like you two or even think specifically? What would you tell yourselves two years ago that you don’t know now? Being on the other side of getting the book out there and looking at other things and all that? I would say to the younger you, but two years ago you weren’t all that much. The early COVID years, whatever.

Olatunde Sobomehin I would say two things. The first is. You know, I didn’t really realize how much the book was going to be read. You know, and that shows you know, that shows that had I known that, I think every single word, every single opportunity to sort of grind out the true essence of the material, I would have just cherished that that much more. Right. We want to put together a good book we want to put together. But I didn’t I didn’t know people were actually going to have it in hand. Actually, I never would have guessed I would be on a podcast with someone like you. And so those things I would have, I wish I would have known. And the second thing is, I really wish we would have dug into, you know, the business model, the things again, another salute to kind of time with you, because we would have thought I think we would have thought about. We’re playing catch up now. It’s out there. And now we’re trying to get ahead of, you know, what momentum. And again, it comes from an expectation of not really knowing what was going to happen. And this book, frankly, for me, has surpassed expectation in terms of how much it’s been received.

Sam Seidel I love all that. I might add a couple of thoughts. One being. Enjoy. Just really make sure to enjoy along the way and to kind of document that enjoyment. Like I just created a folder. It goes out at one of my email and one of my photos actually on my phone to just start. People have been sending such beautiful messages and pictures of their kids with the book and videos. I, you know, just these really great things. And I think I don’t think I’ve taken them for granted, but they go by fast. You know, with all this digital technology, it’s like you get a text that you’re in the middle of a meeting, you look at it, you heart it. You know, these are beautiful. I mean, this is so gratifying and like soul feeding. So don’t, you know, build the systems early to kind of like receive what folks are are giving and the other and maybe this is more tactical or something but we get a lot of interviews that didn’t make it into the book. We talked to a bunch of people we really admired. I think there’s ways that we could have been more methodical about sort of like each of those pieces belong somewhere. It can be an article later, it can be, you know, they mentioned us doing a podcast still can do that and it still can.

Peter Winick Be more stuff. Still has opportunity for.

Sam Seidel Absolutely no question. That my only thing would be like plan for that, right? Because as soon they say we’re going to play catch ups and now we might we would go back to our Google Docs and say, like, okay, like, let’s look at all those interviews again. But we weren’t necessarily like laying the blueprint for that upfront. It was more like focus on getting the book done, which is a very natural thing to do when you’re busy and you’re trying to get.

Peter Winick To important to think about in advance. So. Well, this has been great.

Sam Seidel Yeah.

Peter Winick Appreciate the conversation. Appreciate the book.

Sam Seidel Yeah. The time we spent together. And thank you, guys. Good luck with everything. Thanks so much.

Olatunde Sobomehin Peter. Thank you.

Sam Seidel Thank you.

Peter Winick To learn more about Thought Leadership Leverage, please visit our website at to reach me directly. Feel free to email me at Peter at and please subscribe to Leveraging Thought Leadership on iTunes or your favorite podcast app to get your weekly episode automatically

Peter Winick has deep expertise in helping those with deep expertise. He is the CEO of Thought Leadership Leverage. Visit Peter on Twitter!

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