Staring down a surprise $26,000 bill after his first semester in college, Terrence Cummings was certain his dream of higher education was dashed. He persevered and used that experience as his career North Star. Now, his goal is to ensure that money doesn’t stop people from returning to school. Cummings is the chief opportunity officer at Denver educational technology unicorn Guild, a career opportunity platform that is building a “future of work that works for everyone.” On this episode of the Voices of Experience podcast, Cummings details the journey that took him from dreaming about film production to helping millions of Americans progress in their jobs. He also shares how a chance encounter involving burgers and fries helped flip his own career.
Table of Contents0:59 A fake scholarship and a real $26,000 bill
3:16 Ensuring that others don’t face that same nightmare
4:10 How to create a “culture of mobility”
6:27 The role of storytelling in career progression
Hamburgers and leadership lessons
12:50 How to remove luck from career and personal growth
17:21 Attributes of a good coach
18:27 “I would break the cycle of poverty in my family”
21:20 Show notes and credits
In this episode:
- Global Newswire: Guild Transforms the C-Suite and Gives Opportunity a Seat at the Table with First-of-its-Kind Chief Opportunity Officer Role
- Guild Blog: Making Opportunity Equitable: Guild’s Expanded Commitment to America’s Workforce
- Guild Webinar: Driving meaningful — and measurable — DEI impact
- Talent Management: Want to stand out to potential employees? Establish a ‘culture of opportunity’
- Terrence’s LinkedIn: How his $26,000 college bill led him to Guild
Related articles and information:
- Jim Collins: Concepts and books
- Employee Benefit News: Learning platform Guild is out to create upward mobility for frontline workers
- Fortune: An education startup used by Walmart, Hilton, and Disney wants to close the AI skills gap for frontline workers
- Guild on Facebook, Instagram, X and LinkedIn
- Terrence Cummings on LinkedIn
Coming up, on this episode of the Voices of Experience Podcast.
And so storytelling for me equals communication and communication is a big part of being able to progress someone’s career.
How a $26,000 bill and an appetite for change helped Terrence Cummings find his passion.
And from a fairly young age, I made a decision that I would break the cycle of poverty in my family. In order to do that, I wanted to understand how money worked.
Powered by his own experiences, Cummings wants to ensure money alone isn’t the reason people can’t return to school. He’s the Chief Opportunity Officer at Denver edtech giant Guild, a company that is bridging the gap between the classroom and the boardroom. On this episode, Terrence details the journey that took him from dreaming about film production to helping millions of Americans progress in their jobs. He also shares how a chance encounter involving burgers and fries helped flip his own career. Terrence, welcome to the show.
Excited to be here.
Before we get into your current role, I want to step back in time and ask you a question about a story that I read that you wrote about. So you discovered after starting college that your scholarship wasn’t real and that you were facing a $26,000 bill for the previous semester. What happened there?
I still would love to know, but I’ll give you the story from what I do know. It was my dream to go to NYU. I wanted to go into Hollywood and be a film producer. I love storytelling. It’s one of my favorite things, and you can see behind me, at least partially, from floor to ceiling, I have movie stills that have been either characters or moments of film that have been really important to me. So NYU is the place to go for that. I ended up getting into NYU specifically for business, and I said, if I can get in for business, I can sneak my way maybe over to the Tisch School and ultimately become the producer I wanted to be. And my family couldn’t afford it. And so even after I’d gotten in, I said, “Well, I guess that dream has to be deferred at this point.”
Luckily, it seemed at the time, my aunt was doing business with someone who knew someone on the board of trustees, and we didn’t have a great understanding, or actually, we didn’t even have a bad understanding of how college really worked and how college finances worked. And so she said, “Let me talk to him.” She went and she talked to him. He came back and said, “I talked to my friend on the board of trustees and you have a full scholarship.” I went, “Great, that’s all you need.” Someone says full scholarship, and it is true. And so I showed up to NYU, had my first semester, and then when I went to go register for my second semester, it said, “You owe $26,000 before you can register.” And I said, “No, I don’t. That’s not how this works.” And so we contacted the guy and he said, “Oh, well, I didn’t tell you, but it ended up not working out.” And so that’s what it was, and many people can probably relate to this, but $26,000 at that time, it was effectively infinite.
You could have had a thousand, million, billion or trillion behind that dollar figure, and it was all the same. And so that was where I said I hit my first midlife crisis at that point. What am I going to do? I had this dream and it’s not going to happen. That’s the backstory.
What a nightmare. So how did that experience motivate your path to Guild and ultimately your desire to create pathways for education?
Very directly. What it showed to me was having the aptitude doesn’t mean that you have the accessibility or ability or opportunity to go to school. And something that I told myself at the time is, I don’t know exactly how this is going to happen, but I want to figure out a way for someone that has that aptitude to be able to make sure that money specifically is not the reason why you can’t go back to school. Again, I didn’t know how that would manifest, and it took a number of years before it did, but when Guild came across my radar, I went, “Oh wow, this is it. Why didn’t this exist a long time ago?” And even if it did, why didn’t I know about it? And so it very directly impacted my north star of what I had at the time, and therefore when Guild came up, it impacted my reason for joining.
That’s great. We’ll talk more about that north star later. I want to get into your current role. So your newly created role, Chief Opportunity Officer is a twist on what we typically think when we hear COO. From what I’ve read, your role is designed to help Guild’s community advance in their careers. And what does creating economic mobility look like in a practical sense?
I’ll hit this from a couple of different angles. One, what it means from an outcomes perspective is that we see that people that use Guild, we call them learners, they are more than two times as likely to end up either changing role or having a salary change than those that don’t. They also are more likely … So actually if you split that up, those two components are very important. So you could have a role change that might be, I’m going to end up in a completely different say industry than I am … or sorry, a function than I am right now. But that might be a lateral move in the near term, in the near term, a lateral move. But in the long term, it could really set your career up or it could be a promotion within the function that you have today. And so we look at both salary change and a role change.
So from an outcome perspective, that’s what that looks like. Practically, there are a couple specific stories that come to mind to bring it to life is you’ll have someone … There was someone named Tony, and what Tony needed was job search navigation support. And so what we helped him with is how do you tell your story? How do you understand the skill sets that you have gained through education and just through working, and make sure the people that can resonate with the people that you’re talking to when you interview. And so that’s one set of things that we do is job search navigation. Other times something that could hold someone back is more traditional education. There’s specific skill sets or credentials that I need.
There’s someone named Vaden that comes to mind here where he got a certificate on his way to getting a master’s that was on executive leadership, and that gave him a promotion to a senior operations position. So now he’s running a team of over 300 people at this moment. The third angle I’ll give is sometimes it’s not about the specific skill sets that you can demonstrate from a traditional education perspective, but it’s about learning a language. And so there’s someone, Doris, who learned English, she took English language learning through Guild and became … She was promoted to a cake decorator. And so there’s multiple angles that I can take, but we can help you with your job search navigation skills, storytelling, resume writing, et cetera with traditional education or language support. And I, in my role, do that both within our organization, so we call them Guilders and Guild employees as well as outside of our organization with our members and learners.
How much is storytelling and career progression intertwined?
They’re big components of each other for me, because you can have … There’s the old adage of it’s not what you know, it’s who knows what you know. And the way for people to know what you know is for you to be able to communicate it to them. And people are driven by stories. Humanity over the course of history has been driven by stories. It’s not the only thing that separates humans from other animals, but it’s a big one. That’s how knowledge is passed down over generations. And oftentimes it’s how … People get stuck is the lack of storytelling. There’s a playbook that many people are able to get as to how you can progress in your career and many people don’t have access to that playbook, and that could be because their parents didn’t have it or the stories weren’t told around it. And so storytelling for me equals communication and communication is a big part of being able to progress someone’s career.
That’s great. I’ve also read that coaching has been a crucial part of your life and of your career. The one I want to chat about more specifically is one involving hamburgers and a famous business author. Tell our audience more about that interaction.
Yes. So I worked at a burger restaurant, Red Robin, and I’d been there for about a year and a half when I just so happened to have this one table where it was a jovial table, but in a lot of ways, ordinary. And at the end of it, I got a credit card to run, and this credit card came from an organization called MBNA, used to be a very big credit card issuer, and I’d seen the acronym so many times but didn’t know what it was. So I went back to the table and I said, “What is MBNA?” And the gentleman there said, “It’s the largest credit card company in the world.” And I said, “Oh, I guess I should be privileged and honored to be able to hold this card from the largest credit card company in the world.” And we just kind of started laughing and that led to a conversation around values because what came up was another credit card company, American Express, and I asked him, I said, “I know that it’s cost more for business staff at American Express, so why do people take it?”
And he talked about customer service and the importance of values. I knew that Red Robin because I lived the Red Robin values. I knew that Red Robin was very strong in values, and so we started this conversation about the importance of leadership, business, values, and that conversation lasted for about a year and a half. And during this time period, I learned that this gentleman I was talking to, his name is Jim Collins, and he’d written a book, Built to Last, at the time, Good to Great had just come out. And eventually he said, “How would you feel about coming to work for me?” Because every time that he came in, I would either serve him directly or I would find a way to have the conversation because they were just so riveting.
But yeah, he asked me, “Would you like to come work for me?” And I looked around the restaurant and said, “That seems like a much better career path than what I’m doing right now,” and went to go work for him and it launched the rest of my career.
What was that role?
It was a research role. So I first came on as part of a summer research team, and so we researched over the summer, and at the end of the summer I went to him and I said, “This is what I have, so I’m going back to Red Robin, or can we keep doing this thing?” And he said yes. And so I ended up working for him for a little over two years and did a wide variety of research projects. The bulk of the work that I did led to a book called Great by Choice, but I did a lot of research into boards of directors. When he would have speaking opportunities, I would research whether or not they were good speaking opportunities. Mostly we became friends and that was, to this day, the biggest outcome for me there.
And we’ll link to all of those books on our show notes for any of our listeners that want to go take a peek at them. What was the most important lesson that Jim imparted on you?
I’ll say a couple of them. I learned the importance of work ethic and rigor because the standard that Jim said was basically the work that I do is going to land in … Wall Street Journal’s going to write about it. New York Times is going to write about it. Millions of people are going to read it. It’s going to be right, period. And this would lead to occasions where the summer research team meets at the beginning of the summer. You come back next week and someone’s not there anymore, and that’s real. And it’s not in a mean kind of way. It’s like this work is important. And so that was one thing that really instilled upon me. And so I would find every article written about an organization from its start, which meant getting on a plane sometimes to go to the one library that’s in Illinois at a community college to find the last article.
And that work ethic was really big for me. The second that’s related is I then left Jim and establish that same level of rigor and learn that the rest of the world doesn’t. Actually, I was talking to Jim afterwards, I said, “They just won’t do this.” He said, “Sometimes you have to ask yourself whether the work in particular that you’re doing does require that standard.” His work did require that standard and not every role does, but that was the biggest direct lesson. The other thing that I’ll say that’s indirect, the reason I said that’s direct is because he also instilled upon me a confidence that I hadn’t gotten before. I was working at Red Robin and I was a good waiter, believe you me, I was a good waiter. But it’s a difference when you’re going to go work for someone of that stature who means something to the outside world and believes in you. And it was huge.
I mentioned becoming friends was the biggest outcome, and it’s because to this day, Jim and I, we go for walks and talk about business and he asked me for advice, and I’m like, “What?” It’s wild. And to be able to have that level of confidence instilled in me has been able to drive my career.
That’s great. I want to take that interaction and that sort of chance encounter and relate it to something that you wrote recently. So I’m going to ask you a question that you yourself posed on Guild’s blog. These are your words quote for quote here. So, “How can we make a world where you don’t need the luck I had to find opportunities.”
It’s a great question. Yeah, no, I’m joking. Yeah, so there’s something else I put out recently about packaging serendipity, and these two things go hand in hand. These two things go hand in hand because one, it’s not easy to do this, but what we have found through external research looking at our own internal research is that there are five elements to building out a culture of opportunity, which is the answer to that question over time. And those five elements, to go in order, because I believe that the order is important here. The first is designed for the marginalized, and so that’s putting DEIB at the center of everything that you do. Thinking about the programs and the policies that are put together and are they designed for the most marginalized employees that you have. Because it’s about the environment. If someone shows up every day to work and the environment doesn’t feel familiar or safe to them, nothing else matters. That’s why it’s first. And that’s so easy to overlook for most people because most people are not marginalized. So if you’re not from that group or one of those groups of people, then it’s really difficult. People try really hard, and I love the trying. I think that’s important. We need to keep doing that, but people try really hard to put themselves in the others’ shoes, but it’s really hard. So that’s why that’s first. Second is secure the foundation. Secure the foundation is making sure that employees have the baseline level of support they need to even think about growth and development.
If someone is worried about putting food on their table, it’s very difficult for them to think about how do I grow and succeed if they either don’t have the right benefits or the benefits they have are not accessible or understandable to them. Same thing. Third is unlock learning, which is the core of what we’ve done from the start at Guild. And so this is having an equitable, an affordable and accessible, both education and learning packages, so people can get the skills they need. Fourth is cultivate connections. This is about professional capital. How do people get professional capital? And I love the work that Ross Chetty and his team have done around this as to how that ties to economic mobility because it’s not just meeting anybody, it’s meeting folks that are in a different social and economic class from you, and so they can be able to pull you up.
And the fifth is pave the pathways. And this last one is where I think people often jump to automatically is if I do the resume work, the interview work, if I make sure that you can see that you can go from A to B, then that’s enough. Cool. But if the programs and policies aren’t designed for them so they don’t feel psychologically safe at work, if they’re thinking about how do I put food on the table, if they don’t have the skill sets and if they don’t have the professional capital, then you can help them with the resume all they want. And so putting those five together, which again is not easy, is the core.
How do you walk the walk and not just talk the talk on implementing things like this?
A lot of education and a lot of push from many different angles, not just from Terrence, from many different angles, because many times, again, going back to the fact that most people are not from marginalized groups, by definition, it means that there’s a necessary accountability that has to exist. And we can all, every individual, including me, we can all slip up in this world, but it takes the general psychological safety in the organization for someone else to be able to call me out, to be able to call whomever else out to say, “Whoa, that policy, can we look at it from a different angle?” And it’s really wonderful to see that start to really proliferate around an entire organization. When you see people … And calling out is probably too strong because not the way that it feels. It’s recognizing, it’s putting interventions in place. It’s hard work. It’s a lot of accountability that you have to put in and a lot of education.
And the education goes back to the point I brought up before that most people haven’t been in these positions and been a part of these groups. And so being able to understand what it’s like to be in the shoes of another person is really critical.
Great. We started down this path talking about coaching and how important it’s been to you. Given the coaches and mentors you’ve had in your life, what are the key attributes of a good coach or of a good mentor?
There’s so many. Being a good coach is incredibly hard. And there are two things that are at the core of it. One is being able to listen and I mean really listen, not listen to say the thing next, but deep listening. And then another is asking powerful questions. Again, those two go hand in hand. If you’re not listening, you can’t ask powerful questions, at least not ones that’ll make sense in the conversation. And so those two things are incredibly important.
In the end, what a coach is doing is they’re helping you as the individual to unlock, I’ll say things because there isn’t a specific … but unlock skills, to unlock knowledge, to unlock wisdom within you. And so in order to do that, I need to talk a lot less than you. So asking powerful questions is a second one. And again, those two things go hand in hand. Two others are you have to be able to understand people because if I can’t sense who you are, what your context is, where you come from, what that might mean for what coaching tools I can bring in, it’s very difficult for me to ask those powerful questions. And then the other is presence, being there, being in the present with the person. Again, all that fuels asking powerful questions and listening, which I think are the two at the core. So I hope that that’s really helpful.
I want to switch gears a bit. I saw that your bachelor’s degree is in finance, which seems like a departure from your current role. How has a business degree helped you progress in your career?
I’ll give the why first and then we can talk about the how. My family didn’t have a lot when I was growing up. And from a fairly young age, I made a decision that I would break the cycle of poverty in my family. In order to do that, I wanted to understand how money worked. Even when I was talking about film earlier, you noticed I said I wanted to be a producer, the producer who shows up with the checks. And so money and understanding of money has been so important to me for a long period of time. Behind me, you can’t see, but in addition to all of my film things, I have books that are in different genres in my favorite books. I have the Book Buffet. I have The Intelligent Investor sitting behind me.
And I believe that having that solid understanding not only for myself but for others, it’s what will lead to us being able to provide capital for those that don’t have access to capital in the same way today to be able to break the generational wealth barriers that we see. And the purpose of my team, as I’ve stated, is to eliminate the wealth gap. So that’s the why behind the finance degree. How it’s helped me is that the same reason that I said that I love Guild’s business model has been something I’ve been able to hold and what didn’t exist in the other companies I’ve been in, but I’ve been able to hold it within Terrence in the variety of industries and functions that I’ve worked in of how can I take a solid understanding of how this business works to ensure the business can also work for as many people as possible?
And in my current role, that’s super helpful because one gives me a level of credibility in the organization that might not exist for someone that came into this role purely from a altruistic or philanthropic perspective. That is my aim. Eliminate the wealth gap is my aim. But I have the conversations with our CFO around financing and what that looks like for us. I can build models and spreadsheets and understand how that’s going to impact our bottom lines. And so that mix is very, very important.
The last question I have for you here is one that we ask all of our guests, which is as a voice of experience, what is something you’d like to pass on to our listeners?
I’ve said this word many times during this interview, and that’s listen. One thing that I’ll add before it is surround yourself by people that don’t think like you, don’t look like you, don’t have the same experiences as you. And listen.
That’s great. I love that. Well, thank you, Terrence. We really appreciate it. And thanks for coming on and sharing wisdom.
Thank you. This has been wonderful.
If you’re looking for more from Terrence on how to create a culture of opportunity in your own company, check out that and more in our show notes. You can find that, as well as past episodes at daniels.du.edu/voe-podcast.
The VOE Podcast is an extension of Voices of Experience, the signature speaker series at the Daniels College of Business, sponsored by U.S. Bank. If this is your first episode, be sure tocheck in every month for a new conversation, and subscribe while you’re there.
Sophia Holt is our sound engineer. Joshua Muetzel wrote our theme. I’m Nick Greenhalgh. We’ll see you next time.