Striking the Right Chord feat. Shai Littlejohn '26

[00:00]Brian Jackson: Welcome to Owl Have You Know, a podcast from Rice Business. This episode is part of our Pivot Series, where guests share stories of transformation in their lives and careers.

Shai Littlejohn’s career is a masterclass in bold moves and unexpected pivots. As director in corporate counsel for global supply chain and innovation at Starbucks and a singer-songwriter, she’s navigated law, business, and music with a fearless approach to change.

In this special episode recorded during the Women in Leadership Conference at Rice Business, we dive into her journey, the biggest legal challenges facing companies today and how the Executive MBA program is shaping her perspective. And, of course, I couldn’t let her go without asking about her go-to Starbucks order. Stay tuned to find out what keeps her fueled.

Today, we're joined by Shai Littlejohn. We're here at Rice Business. The Women in Leadership Conference is happening downstairs. You know, off the bat, what's the atmosphere? What does it feel like to be a part of the conference?

[01:04]Shai Littlejohn: It's inspiring, high energy, so many wonderful women that are just so many different talented people across different industries. So, I'm excited to be here and meet some new people.

[01:16]Brian Jackson: And the stories, I find the stories to be so inspiring and incredible.

[01:20]Shai Littlejohn: Yeah, they are. They are. I mean, I've met probably 30 people already that I've had little mini stories. We're connecting on LinkedIn. We're going to be getting together at some point, hopefully. And we're really trying to focus on networking and community building because that's what we need to do to, kind of, create more space, room for women in these corporations in America, entrepreneurial opportunities, things like that. So, we're going to help uplift each other to get there.

[01:43]Brian Jackson: I think of you and your background, you've had such a breadth of experience. And you went law, music, law, and you've also pivoted a bit in between. You know, as you're approaching these discussions, do you find having those past experiences, that creative thought, you know, kind of, helps you to really engage?

[02:03]Shai Littlejohn: Yes, I do, especially because I moved around a bit geographically. So, I grew up in Ohio, but then I went to law school and undergrad in Washington, D.C., where people tend to be a little bit more informed about government and how it works because they work there in the government offices and in the surrounding corporations.

[02:22]Brian Jackson: Proximity bias.

[02:22]Shai Littlejohn: Their proximity bias. And then, and people respond differently to each other, especially across both sides of the aisle. You have, you're attending a lot of the same events. It's not the, sort of, negative-spirited environment that we find a lot now on social media.

Then, I moved from there to Nashville, Tennessee. So, in Nashville, there's, you know, a little bit of a blue area, but in a red state. And there's a lot of people with a lot of different viewpoints, but I had never lived in the South. So, that was a different experience for me.

And then leaving there and then coming to Houston back to a major city, where there's a lot of different diversity in the city that Nashville did not have, but Washington D.C. did have, I'd say I probably prefer D.C. and Houston. I'm a big city type of person.

[03:09]Brian Jackson: Or metropolitan, some might say.

[03:10]Shai Littlejohn: I'm a metropolitan woman.

[03:11]Brian Jackson: There we go.

[03:11]Shai Littlejohn: I'm a metropolitan woman. That’s it.

[03:12]Brian Jackson: So, what brought you to law? What inspired you? I mean, really, to me, I think it's a career where it has a calling, some people would say.

[03:21]Shai Littlejohn: So, the calling for me was my dad begging me to go to law school all my life. So, I grew up in Ohio. And at the time, you know, I saw doctors, lawyers, teachers, dentists. That was about it. And so, I never considered other opportunities, really. My father was a lawyer. He grew up in South Carolina. That was his way out of poverty — to moved to Ohio and then get into the middle class. My dad ended up being elected judge in Dayton, Ohio. He encouraged my mother to go to law school when I was, I think I was maybe three years old or so when my mother went to law school. So, this, kind of, ran in the family. And my dad said, “You can do anything you want to do after you go to law school.” And he told me that a million times. And so, I just always knew that I was going to go. I'm very close to my dad, so I didn't want to disappoint him, but I also didn't have an idea for exactly what else I wanted to pursue. So, I was fine to just go from high school to undergrad to law school, as if it was just natural for me.

[04:19]Brian Jackson: Yeah. So, going home for family dinner, you actually maybe had to brief a bit, prepare both sides of the argument.

[04:24]Shai Littlejohn: My first job was working in my dad's law practice before he became a judge. And I just filed papers and answered the phones in exchange for cheeseburgers and candy.

[04:34]Brian Jackson: Law clerking. It's the way to figure out if you want to do it or not. So, from law, music, was music your way of, kind of, saying, “Okay, I'm going to go do my own thing?”

[04:45]Shai Littlejohn: Well, no. So, I was a… I always loved music. And I sang in choirs. And I've had a little acapella group in high school and things, so I always loved music, but I never saw it as a potential occupation. The musicians I knew, they were probably struggling, I would say, financially. And I never wanted that sort of lifestyle. So, I liked the creative element of it, but I didn't want to be a starving artist.

And so, I actually, I don't know that I was conscious of that when I was younger. It's just that I never saw it as a career path. But as I got older, I kept saying, “I've always wanted to make my own music. I've always wanted to write songs and things.” And it really took the illness of my mother to really trigger that decision that I needed to do everything I wanted to do in life and not just focus on a career.

So, I wasn't really loving my law career in D.C. I was having some success in it, but I was working all the time and I felt like I had no time for anything else except to meet my friends for dinner at, you know, 8:00 at night or something after working a long day. And my mother ended up being diagnosed with glioblastoma. And she was being treated here at MD Anderson. And when… and one time, she was getting really progressed in her illness, came out of remission and she was, you know, at this point, terminal.

And she said to me, you know, “I've done everything I want to do with my life.” Just basically telling me, “This is all okay.” And I thought, “There's no way I could say that today, because all I've done is work jobs where I was performing well but I wasn't really enjoying it. I just felt like something was keeping me from the things I would enjoy. And I knew that music was one of those things.” And so, from that time, I said, “I got to figure out a way to incorporate things in my life so that I could, too, could say that I've done everything I wanted to do.

[06:34]Brian Jackson: So, how do you push back? I mean, you're having professional success, you're recognizing, “Okay, on the personal front, I need to carve out the time.” How do you start to do that? I feel like, once the job's crept in, it's hard to push it back out.

[06:48]Shai Littlejohn: Yeah. So, I had, it was a couple of things. One, the illness; but then, also, I was in a work situation where I had a manager who was not the best, wasn't my favorite. And I knew that I wanted to leave that position. And so, I decided that I was going to do a summer vacation. Like I said, I’m going to take a summer vacation break first, decide what I'm going to do.

So, I was Googling of summer music teacher thinking I could finally, you know, spend the week doing something like. And Berkeley College of Music came up in my search. And I thought, “Oh, I could go there for the summer program for a week and just have fun.” And so, I did and had the time of my life. Time of my life.

And then I came back. You know, maybe a month later, I'm on the phone with one of my friends and, you know, having that, “Do you like your career? No. Do you like your career? No.” And she said, “Well, you have so much fun at Berkeley. Why don't you go there full time?” And something just, kind of, clicked. And while I'm on the phone with her, I write out the college essay. I, like, fill out, you know, all of the questions. And then I hit, put my credit card in, hit submit, and then they invited me to audition. And then I thought, “I could actually do this. If I rent out my house and get a place in Boston, I could start my own law practice and then I could go to school and I could commute back and forth and this'll work.”

And so, I said, “Okay, if I get admitted and I rent out my house, then I'm going to do it.” So, I got… I went to Boston for the audition. A week or two later, I was admitted. Then, maybe a week or two after that, I was able to get renters from my house. And I was like, “Well, I guess I'm going.” So, I quit my job and started my practice. Yeah.

[08:31]Brian Jackson: Just a tremendous amount of courage.

[08:34]Shai Littlejohn: Well, it took a lot of courage, but I don't know, I think I was in a strange place back then. Like, I was worried about my mom, but also very motivated. I didn't like the job I was working in. And I didn't want to have regrets. And I think her illness made me think about what regrets I might have if I don't, like, take the opportunity to do something now.

[08:54]Brian Jackson: So, it's purpose-driven. What that purpose is can be parts of so many different things.

[09:00]Shai Littlejohn: Yeah. Mm-hmm.

[09:01]Brian Jackson: So, you're a singer. What type of genre?

[09:03]Shai Littlejohn: Well, so, I'd say, call it singer-songwriter. A lot of it comes out as, like, a pop, folky, folky like roots, kind of, a little country, all of those things mixed in into one. Little bluesy, sometimes. 

[09:16]Brian Jackson: Nice. I feel bad for the folks in church who are near me within a couple miles. When I sing, it's not pretty. So. I won't be.

[09:23]Shai Littlejohn: Well, I have a gospel singing background, although I never sounded like the gospel singers at my church. I was never a strong lead for that kind of music. But I love it.

[09:32]Brian Jackson: I sing into the book, try to, you know, vibrate against that nowhere else. So, now, you're at Starbucks. Could you tell me about your position there and, kind of, you know, what brought you to Starbucks?

[09:44]Shai Littlejohn: So, I was working prior to that for a diversified energy company in Tennessee. I ended up moving to Tennessee because I thought, “I can't keep paying this Berkeley tuition. I already have my degrees. So, I'm going to just start commuting between Nashville and D.C.” And I started picking up clients in Nashville and then did, instead of commuting from Boston and Berkeley to D.C., I started commuting from Nashville to D.C. This was about five years of commuting, by the way.

[10:14]Brian Jackson: God.

[10:16]Shai Littlejohn: And so, then, I was at Delek, a company called Delek. And from there, I decided I wanted to move to Houston. And so, I thought, “I need to find...” In the remote jobs, it was pandemic time, right? So, remote jobs were starting to come online. And I thought, “If I could find a remote role, then I could move to Houston and be near my family.” And that's what I did. I applied to Starbucks because they had some remote openings. And that's how I switched from the oil industry to the coffee business.

[10:45]Brian Jackson: So, if you had to have one line to it, what's the biggest difference between oil and gas and coffee?

[10:50]Shai Littlejohn: Culture.

[10:52]Brian Jackson: Culture?

[10:52]Shai Littlejohn: Corporate culture. Yeah. I mean, Starbucks has a very unique corporate culture, which I hope will continue to be unique, because… but, you know, you have to balance culture with productivity. And I think a lot of companies don't get that right. And I think it's very difficult to get that balance right, work-life balance plus productivity in the company. But, so, Delek and that business was just more smaller, much smaller company, too. Yeah. They were about, you know, less than $2 billion versus Starbucks over $100 billion.

[11:27]Brian Jackson: Yeah. I mean, y'all are everywhere.

[11:28]Shai Littlejohn: Yeah.

[11:30]Brian Jackson: Your stage of your career now, and you're pursuing an Executive MBA at Rice. I want to know, how are you balancing your time? And when you're done, how do you, what do you think you're going to do with all that extra time that you would've typically earmarked for the program?

[11:45]Shai Littlejohn: Yeah. So, it has been very challenging on the time management piece. It's helped that I have a remote role. And so, I don't have to travel a ton. But it's been challenging because it's, you know, essentially, four classes while I'm in working full-time. But it's been really great because of the cohort I'm in. My classmates are fantastic. That's one of the things that's difficult to juggle, all of our social events, because we've become really great friends, which I love. And being newer to Houston, I've only been here a little over three years now, it's been a welcome community. Rice has been a welcome community to be a part of.

But the coursework is challenging, and it's something I've always wanted to do. That's why it was on my bucket list to study business. Being a lawyer, you're constantly advising on risk mitigation. And it takes you to put on a different hat to be able to take risks and be an entrepreneur.

And so, even a lot of times, I will study different businesses that I think I might want to enter. And I'll think of all the reasons why I should not enter that business. And so, this program will help me to see the opportunities more, not just a risk.

[12:59]Brian Jackson: Yeah, to recognize. I mean, it's… I'm a JD/MBA. And to me, it's a perfect cross-pollination of, yes, understanding risk, but then maybe the business side is, how do you mitigate it? And how do you turn it into something profitable?

I'd like to talk about, you know, the experience of going through the Executive MBA program while also holding a senior role at Starbucks. And could you tell me about, you know, the opportunities you're seeing to apply what you're learning in the classroom to real-world business opportunities?

[13:28]Shai Littlejohn: Sure. I'm already using what I'm learning. So, I support our global supply chain organization, the research and development and innovation team, and our commercial team. So, a lot of the capital projects that we do at Starbucks are things I advise on, and also some of our ESG program.

So, I negotiate a lot with our sourcing team on supply agreements, things like capital equipment purchases. Some of the innovation work that we do will… we have engineers on staff that invent equipment. And we'll have to negotiate development agreements with different equipment manufacturers so that those inventions come to life.

And in doing so, we might negotiate, say, warranty terms. And I understand now, through my accounting course, why reserves for warranties would be something on the mind of the business person that I'm negotiating with. And that's not something I had insight to before. So, I was very familiar with all the legal protections that I wanted to get into that contract. But I wasn't always clear on what the businesses were fighting over, you know, what made them want to secure certain terms in their contracts. Now, I understand a lot more about the timing and payment terms and the benefits there. So, I become a stronger negotiator because I'm more knowledgeable through the Rice program.

[14:49]Brian Jackson: You understand the variables at play and why they matter. And I like to look at the break points, my counterparty. And I'll map them out and say, “Okay, seven's going to break them, but they'll likely take three. And then I try to push for seven.”

 

[15:03]Shai Littlejohn: Yeah. Right. Yeah.

[15:06]Brian Jackson: But I didn't know why I was pushing for it. So, I think that's a great example of, like, actually understanding why it's applicable. So, being a woman in business, what does an event like Welk, you know, mean to you?

[15:17]Shai Littlejohn: So, being a woman in business is exciting, and being at this conference is just really invigorating because there's opportunity all around us. No matter what's going on in the world, we, women, have so much potential and opportunity that we can pursue. And so, this group is ready to do that and I'm so excited to be a part of them.

[15:35]Brian Jackson: I think it's totally inspirational. So, if you had a hope for one thing that the attendees today would take with them, what would that be?

[15:45]Shai Littlejohn: That they have to decide what they want and just go for it. You know, it's like, if the law doesn't… you can't look for laws necessarily to help you all the time or look for the environment or time to be right. We have talent that we can bring to the table. We have ideas. And nothing can stop that. We just have to keep putting them out there. You're not going to always get, you know, the reception you want. But that can't stop you from just trying and going for it.

So, I see entrepreneurs in the room. I see future corporate executives here. And it's really exciting to see. And as long as we believe in ourselves and keep pushing and advancing, it's going to happen. I'm an optimist. I believe it's going to happen.

[16:25]Brian Jackson: I love the optimism and supporting each other. I think that's what this is about. It's about being there and offering that background and actually propelling others to do more. To wrap it up, you're at Starbucks. I have to know, what is your go-to coffee order?

[16:41]Shai Littlejohn: So, my favorite taste at Starbucks is the chocolate cold foam. So, anything you can put the cold foam on, I could eat that in spoonfuls. Like, that is some good stuff. And so, yeah, so, I take a cool brew with the cold foam.

[16:56]Brian Jackson: Okay. I'll try it next Monday.

[16:59]Shai Littlejohn: Yeah, you got to try it. You got to try it.

[16:59]Brian Jackson: I'm a plain Jane Americano type of person or a latte. So, [crosstalk 17:03].

[17:03]Shai Littlejohn: Yeah, we saw those, too. Lots of them.

[17:07]Brian Jackson: Well, thank you so much for joining me, Shai. It's been such a pleasure. And yeah, very happy to have met you.

[17:12]Shai Littlejohn: Thank you. Same here.

[17:14]Brian Jackson: Thanks for listening. This has been Owl Have You Know, a production of Rice Business. You can find more information about our guests, hosts, and announcements on our website, business.rice.edu.

Please subscribe and leave a rating wherever you find your favorite podcast. We'd love to hear what you think. The hosts of Owl Have You Know are myself, Brian Jackson, and Maya Pomroy.