Jubee Vilceus Of Yellow Tail Tech: Lessons I Learned From Last Year To Take Our Organization to the Next Level in 2024
An Interview With Chad Silverstein
Sticking to Our Core Mission: I’ve come to accept that focusing on what I do best is the most authentic way to operate. It’s tempting to try and be everything to everyone, but I kept coming back to why I started this journey — to help people with no tech background break into IT. It’s been amazing to see people who were total newbies become experts.
This series aims to discuss the experiences and lessons learned by top executives over the past year, and how these insights are shaping the landscape for change and innovation in 2024. The past year has been a time of unprecedented challenges and opportunities, requiring adaptive leadership and innovative strategies. We believe that sharing these experiences can inspire and guide others in their endeavors to drive positive change in their organizations and industries. I had the pleasure of interviewing Jubee Leroy Vilceus.
Jubee Vilceus is the CEO and co-founder of Yellow Tail Tech, a company that helps people with no IT background get into the tech industry. He loves guiding people through career transformations and uses his IT and education background to create programs that are simple, practical and effective. He’s the host of “The Long Game” podcast where he talks about career growth, perseverance and the value of long term success.
Thank you so much for doing this with us! Can you share a little about your background and what pivotal moments led you to your current position as an executive?
I have had a couple of businesses across different industries before, each built with the goal of addressing specific gaps in the market. My pivotal moment came when my wife, Paloma transitioned into tech and we realized what was lacking in the job market, also with the gaping hole between what the tech industry needed and what traditional education was dishing out. This realization led me to co-found Yellow Tail Tech with a mission to bridge that gap by providing practical, job-ready training. From this grew Yellow Tail Tech, a training organization I co-founded to skill up students for the demands of the modern workforce, turning optimism into practical action. I owe it to my past experiences that I’m now leading the charge at an EdTech company, empowering people to boldly venture into tech with the skills they need.
What were the early challenges you faced in your career, and how did they shape your approach to leadership?
In the early stages of my career, one of the biggest challenges I faced was learning to navigate uncertainty and resource constraints. When you’re building something from the ground up, especially in tech, there are countless moments when you don’t have all the answers, and the resources are never enough. Circumstances pushed me to rely on my wits, go with the flow, and develop a cozy relationship with uncertainty.
I emerged from those trying times a wiser, more empathetic leader, with a deeper understanding of the power of resilience to transform setbacks into opportunities. The biggest lesson I’ve taken away is that leadership isn’t about standing alone at the top, nor is it some prized possession to hold onto. With your people by your side, it’s a process of sharing burdens and victories, bringing everyone’s strength together to create something great. It’s also about being honest, and leading by example — qualities that I believe are the foundation of a strong and effective leader.
We often learn the most from our mistakes. Can you share one that you made that turned out to be one of the most valuable lessons you’ve learned?
You know, one of the biggest mistakes I made was trying to do everything myself in the early days. I thought that to be a successful leader, I needed to have all the answers and take on every task. But I quickly realized that not only was I burning myself out, but I was also limiting the growth of the team by not allowing others to step up and contribute.
I shifted, not controlling everything, and let my team members take action and do things. Working collectively with others and distributing tasks ultimately saved me from burnout during that transformative phase. I step aside and watch how capable colleagues blossom when given the freedom to bring their individual talents and strengths to the table. That lesson transformed the way I lead, and it’s been a game-changer for our growth at Yellow Tail Tech.
As an executive, how do you define success, both personally and for your organization?
As an executive I define success as making a lasting impact personally and within my organization. Personally it’s about continuous growth, learning and challenging myself to be a better leader every day. I measure success by how well I lift and inspire those around me — whether that’s my team, our students or the community we serve. For Yellow Tail Tech success is about our students. When they thrive in their careers and achieve things they thought were impossible, that’s the real measure of our impact. It’s about flipping the script, taking action, and leveling the playing field — not just crunching numbers or chasing ROI in the tech industry. When we can honestly say we’ve made a difference in someone’s journey, that’s when I know we’re really succeeding.
Reflecting on 2023, what was the most unexpected challenge you faced, and how did you navigate it?
Looking back on 2023 one of the biggest surprises was the tech job market, especially with all the job losses across the industry. It was a wake-up call, showing how crazy the landscape can be even in sectors that are supposed to be stable. We had to move fast to make sure our students weren’t just equipped with the right skills but also prepared for a more competitive world. That meant being super agile — listening to industry feedback, building stronger relationships with hiring managers and updating our training programs constantly. It wasn’t just about keeping up with the trends but being ahead of them and making sure our curriculum stayed relevant. It wasn’t easy but we did it and we’re more robust for it and better at getting our students to success despite the job market.
What was a significant risk you took this year, and how did it turn out?
I launched The Long Game podcast, probably one of the biggest risks that I have taken this year, where I actually didn’t plan to start but kind of dived into the world of podcasting. It was definitely a risk that it wouldn’t resonate with our audience or just not get the traction we hoped for, especially as there are so many voices already going out into the tech and career space.
I’ve always thought that kicking open the doors to honest, unbridled chats about the real nitty-gritty of building a lasting career would truly supercharge our community. The outcome? This surpassed the highest hopes. What started as a conversation has turned into a bridge to the gap between us and our audience, fostering lasting relationships that go beyond the mic. One of the most exciting outcomes is the growth of genuine relationships — people are relating to us in a way they never could before, and their praise is music to our ears. A single bold move and suddenly everything fell into place. Helping others discover their own tech potential and celebrating their successes — that’s what drives us.
How has your company’s mission or purpose affected its overall success? Can you explain the methods or metrics you use to evaluate the impact of this purpose-driven strategy on your organization?
Getting people with no IT background into the tech game is what gets us out of bed in the morning, and it’s what’s propelled us to where we are today. At the center of everything we do, you’ll find a single, guiding principle — it’s what drives our programming decisions and inspires how we interact with the people around us. It’s not just about getting people into tech jobs; it’s about changing lives and providing opportunities that many thought were impossible.
To measure the impact of this mission we look at a few key metrics. First, our students: are they getting jobs? are they getting certified? Second, we track engagement and satisfaction, gathering feedback to make sure we’re really serving our community. Lastly, we look at long-term career growth: are our graduates not only getting jobs but also growing in their careers? These metrics help us measure our impact beyond the numbers; they show us how well we’re living our mission. And every time we see a student succeed it’s a reminder that staying true to our purpose is what drives our overall success.
Have you ever faced a situation where your commitment to your purpose and creating a positive social impact clashed with the profitability in your business? Have you ever been challenged by anyone on your team or have to make a tough decision that had a significant impact on finances? If so, how did you address and reconcile this conflict?
Yes I’ve had situations where our commitment to making a positive impact conflicted with profit. One of the hardest decisions we had to make was when we were offered a partnership with a company that didn’t quite align with our values. On the surface it looked like a great opportunity — big revenue that could have helped us scale our programs and reach more people. But when we dug deeper it became clear their approach didn’t quite align with our mission of genuinely empowering people from all walks of life to get into tech.
So we doubled down on building partnerships that aligned with our purpose and interestingly that led to more genuine partnerships that benefited our students even more. It proved that when you stay true to your mission the right opportunities will come and it creates a culture of integrity that keeps everyone motivated and aligned to our bigger purpose
Could you list the top five things you’ve learned in 2023, with specific examples of how these lessons impacted your decisions or strategies? If you can, please share a story or example for each.
1 . Specialized Training is Everything: You know, one of the biggest lessons I’ve learned this year is that hands-on skills matter way more than just book knowledge. I’ve seen so many people with great degrees who can’t handle real-world tasks. That’s why I made sure we’re doubling down on teaching Linux in a practical way at Yellow Tail Tech. We added more real-world Linux scenarios, and it’s honestly changed the game for our students. They’re going into interviews knowing exactly what to do, and it’s getting them noticed
2 . Adapting to the Changing IT World: The tech world, man, it never stops moving. It’s wild how quickly things change in this field. This year, I really saw how important it is to understand that IT isn’t just one thing anymore — it’s all about specializing. That’s why we’ve been so focused on getting our students really comfortable with Linux. It’s the foundation for so much in IT, and I’ve seen firsthand how being solid in Linux helps them branch out and grow in their careers
3 . Sticking to Our Core Mission: I’ve come to accept that focusing on what I do best is the most authentic way to operate. It’s tempting to try and be everything to everyone, but I kept coming back to why I started this journey — to help people with no tech background break into IT. It’s been amazing to see people who were total newbies become experts.
4 . Listening to What’s Needed: One of the best things I did this year was really pay attention to what the industry is asking for. What I’ve learned is that being proficient in Linux opens doors — that’s why we’ve built our training around giving you a deep understanding of this essential tool. We’ve had so many people land great jobs just because they got super comfortable with Linux. It’s like, sometimes all you really need is to master those basics, and everything else starts falling into place.
5 . Creating a Supportive Community: One thing that’s really stood out to me is how our Slack channels have become like little hangout spots for each cohort. Each group has their own space where they can chat, share what they’re learning, or even just vent when something’s tricky.
It’s been great seeing everyone get so comfortable with each other. I remember this one guy who was really struggling with a Linux concept — he just threw his question into his cohort’s channel, and within minutes, his classmates and even the instructor jumped in with tips and advice. It felt like this big, supportive team effort, and honestly, moments like that make everything feel so much more worth it.
How have these top five lessons from 2023 changed your outlook or approach for 2024?
These lessons have definitely shaped how I’m approaching 2024, making me more intentional about how we’re moving forward at Yellow Tail Tech.
- More Hands-On Linux: I saw how much real projects helped last year, so we’re adding even more. It’s all about making sure everyone’s ready for the real world, not just theory.
- Rolling with Changes: IT changes fast, and so should we. I’m going to keep our content fresh so everyone stays up-to-date.
- More Mentorship: I’ve seen how much students leaned on each other in Slack, so I’m bringing in more mentors and ways to help each other out.
- Teaching What’s Needed: If companies want it, we’re on it. I’ll be paying more attention to what skills are actually getting people hired.
- Building Our Community: I want everyone to feel part of the Yellow Tail Tech family, so there’ll be more ways to connect, share, and grow together.
I’m really focusing on more than just teaching skills now. It’s about building a place where everyone feels supported, confident, and ready to jump into the IT world. That’s the energy I’m bringing into 2024.
In terms of innovation and adaptation, what’s one change you implemented in 2023 or plan to do in 2024 that you believe will be crucial for the future of your business?
You know, one thing I’m really excited about for 2024 is making the learning process feel a bit more like an adventure. We’ve always been about hands-on training, but I want to take it up a notch by adding this gamified element. Like earning points, badges, or even little rewards as you work through challenges. It’s not about making it feel like a chore — it’s about making the journey more engaging and fun. I’ve seen how much more people learn when they’re genuinely enjoying themselves, and I really believe this will help everyone stay motivated and pick up the skills they need in a way that actually sticks.
At the end of the day, it’s about making sure every single student feels like they’re growing, learning, and having a good time while they do it.
As a leader, how do you foster a culture of continuous learning and improvement within your team or organization?
I’m all about creating an environment where learning feels like a natural part of what we do. I’m always learning myself, so my team sees that it’s not just something I talk about — it’s something I live. I make sure they know it’s okay to take risks, make mistakes, and learn from them because that’s where the real growth happens. When someone steps up, tries something new, or learns a new skill, I’m right there cheering them on. It’s about building a culture where everyone feels like they’re growing together, not just professionally but personally too.
Looking at the broader industry landscape, what emerging trends do you think will be most influential in the coming year?
Honestly, I’m seeing more folks turning to tech to handle everyday tasks that used to be a pain, just to free up their time for the stuff that actually matters. And with everyone working from home more these days, cloud services are becoming a lifesaver — just makes everything more accessible and convenient. At the same time, security is on everyone’s radar now, which makes sense since no one wants their info out there. I think it’s all going to play a big role in how the government handles tech too, making things run smoother and keeping data locked down. It’s just about staying in the loop and adjusting as things shift.
If you and I were having a conversation one year from now, and we were looking back at the past 12 months, what specifically has to happen for you to be happy with your progress?
If we’re having this conversation a year from now, I’d want to say that we made a real difference in helping more people start their tech careers — people who never thought they’d get a shot at it. I’d be thrilled if we not only kept up with the rapid changes in the tech world but actually got ahead of them, making sure our students were always learning the skills that matter most.
I’d also want to see that we’ve built an even tighter-knit community, where students, instructors, and alumni are supporting each other, sharing their wins, and lifting each other up. And honestly, on a personal level, I’d want to feel like I’ve grown too — not just as a leader but as someone who’s stayed true to the mission while pushing myself and my team to keep getting better. If we could look back and see that kind of growth, I’d call that a year well spent.
How can our readers further follow your work or your company online?
You can follow what we’re doing by visiting our website at yellowtail.tech — that’s where we keep all our program info and updates. We’re also on LinkedIn, sharing tips, student journeys, and some insights into what’s going on in the tech world. And if you’re into podcasts, tune into “The Long Game,” where I break down tech topics, chat with people in the industry, and share some real talk on building a career in this space. It’s a relaxed way to see what we’re all about.
This was great. Thanks for taking time for us to learn more about you and your business. We wish you continued success!
About the Interviewer: Chad Silverstein is a seasoned entrepreneur and Thought Leader with over 25 years of business experience. He has founded, operated, and exited multiple companies and now builds into a handful of high impact CEOs. Chad has launched multiple online communities, including a recent leadership development platform, and also serves as a strategic advisor for Authority Magazine’s thought-leader incubator program.
To learn more and connect with Chad visit: chadsilverstein.io
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