Vasilii Kiselev, the CEO and co-founder of Legacy Online School.
I am a skilled and experienced executive with a background in building successful ventures. I took a digital manufacturing integrator/reseller from a one-person start-up to a global market leader, which taught me the power of vision and adaptability.
My passion, however, lies in education—I truly believe it has the power to change lives, and that belief drives everything I do. At Legacy Online School, I’m not just following trends; I’m focused on building an institution that prioritizes quality and flexibility. I’m incredibly proud of the community we’ve created—a place where students are inspired and equipped to succeed.
I’m excited about the future and committed to making a lasting impact in the world of online learning. My journey is all about helping students thrive in this ever-evolving digital era.
You can find more about my background on my LinkedIn.
Company: Legacy Online School
We are thrilled to have you join us today, welcome to ValiantCEO Magazine’s exclusive interview! Let’s start off with a little introduction. Tell our readers a bit about yourself and your company.
Vasilii Kiselev : It’s great to be here! My name is Vasilii Kiselev, and I’m the CEO and Co-founder of Legacy Online School. A little about my background: I started out in the digital manufacturing space, where I built a company from scratch into a global market leader. That experience taught me a lot about resilience, innovation, and the value of staying ahead of the curve. But as my career evolved, I became more and more drawn to education. I’ve always believed in its power to transform lives.
That’s really what Legacy Online School is all about—creating an educational experience that goes beyond just following the latest trends. We’re building an institution where quality and flexibility are at the heart of everything we do. I’m incredibly proud of the community we’ve built. It’s not just about teaching subjects; it’s about preparing students for a future where digital skills and adaptability are essential. We want our students to leave not just with knowledge, but with the confidence and tools to navigate an ever-changing world.
What does success mean to you beyond financial growth, and how has your definition evolved over time?
Vasilii Kiselev : For me, success has always been a bit of a moving target. When I first started out, it was all about the numbers—the financial growth, the expansion, the market share. But over time, I realized that true success is about impact. It’s about seeing the difference you’re making in people’s lives. At Legacy Online School, it’s when a student who struggled in a traditional classroom environment finds their confidence and starts thriving. It’s when parents tell us that their child loves learning again. Those are the moments that remind me why we do what we do.
My definition of success has evolved from just building a business to building something that truly matters. It’s not about being the biggest; it’s about being the best at what we do for the people we serve. I’ve come to value quality over quantity, relationships over transactions, and the long-term ripple effects of education over short-term wins.
Can you share a specific failure or major setback that unexpectedly led to a significant breakthrough in your career?
Vasilii Kiselev : Early in my career, when I was building my first business in the digital manufacturing space, I took a risk on a big client contract that, in hindsight, was a mistake. We overextended, and when the deal fell through, it almost sank the company. It was a painful and humbling experience—I remember feeling like I’d failed not just myself, but the whole team that had put their trust in me. But that setback forced me to rethink how I approached partnerships and business growth.
I realized that I needed to focus on building a solid foundation, rather than chasing quick wins. It was this mindset shift that later helped me succeed with Legacy Online School. We’ve grown steadily, not by jumping on every opportunity that comes our way, but by staying true to our mission and being selective about who we partner with. That failure taught me the power of patience and resilience, and it’s something I carry with me every day.
How do you measure personal fulfillment and impact in your role as an entrepreneur or CEO?
Vasilii Kiselev : This comes from seeing the tangible impact of our work. It’s the thank-you emails from parents, the testimonials from students who say our programs changed their lives, or the teacher who tells me they love their job again because we’ve created an environment that lets them teach in a way that feels meaningful.
I try to stay connected to our community as much as I can. I join student meetings, I talk with parents, and I make a point of keeping those lines of communication open. It’s easy to get caught up in the metrics, but at the end of the day, the real fulfillment comes from knowing that what we’re doing is making a difference. That’s what keeps me motivated, more than any quarterly report ever could.
What unconventional advice or practice has helped you overcome challenges and redefine your approach to business?
Vasilii Kiselev : One piece of unconventional advice that has stuck with me is to embrace boredom. I used to think that if I wasn’t constantly hustling, I was falling behind. But I’ve learned that taking a step back—whether that’s going for a walk, spending time with my family, or just giving myself some space to think—is crucial. Those quiet moments are often when the best ideas come to me, or when a solution to a problem suddenly becomes clear.
I’ve also embraced the idea of making “slow” decisions when possible. In a world that glorifies speed, I’ve found that taking my time to think things through—especially when it comes to major business decisions—leads to better outcomes. It’s counterintuitive, but I’ve found that slowing down can actually accelerate progress in a more meaningful way.
How have your setbacks shaped the culture and values of your organization? Can you give an example of how these values are reflected in daily operations?
Vasilii Kiselev : Our setbacks have been some of our greatest teachers. At Legacy Online School, we’ve built a culture that’s all about resilience, adaptability, and learning from our experiences—whether good or bad. One of our core values is “Fail Forward,” which means that we don’t shy away from failure; we embrace it as a necessary part of growth.
For example, we had a curriculum launch that didn’t go as planned—it didn’t resonate with the students the way we’d hoped. Instead of sweeping it under the rug, we gathered feedback from students, parents, and teachers, analyzed what went wrong, and made adjustments. It’s a value that’s embedded in our daily operations, from how we handle setbacks to how we approach new ideas. We’re constantly iterating, learning, and improving—and I think that mindset is what makes Legacy such a unique place to work and learn.
