Taking Chances continues with a conversation at the intersection of legacy business, modern tech, and real-world execution.
In this episode, Shaun Coe sits down with Sebastian Fleischmann, his co-founder at Ascendium Tech, to unpack the journey that led them to build together.
Sebastian’s story is not a straight line. Raised around a legacy family business, he was exposed early to how companies actually run, where they break, and what leadership really looks like under pressure. That foundation pushed him into entrepreneurship at a young age, then into consulting, leadership roles, and eventually deep work in AI and systems design.
What emerges is a builder who understands both sides of the table: operators who need things to work today, and technologists who are designing what work looks like tomorrow.
Together, Shaun and Sebastian explore how that background shaped the creation of Ascendium, why enterprise clients are now demanding smarter systems instead of more headcount, and how AI is quietly reshaping organizational structures across hospitality, staffing, and ops-heavy industries.
They dive into:
- How early exposure to real businesses builds entrepreneurial instincts
- The role of confidence, ownership, and accountability in scaling companies
- Sebastian’s transition from consulting into AI-driven problem solving
- Why most organizations are not “behind,” they are just overloaded
- How AI is changing operations without replacing the human layer
- What hospitality teaches us about speed, margin, and systems under stress
- Why adaptability matters more than tools in the AI era
- The real risks and realities around data, infrastructure, and cyber threats
This episode is less about hype and more about how builders actually think when they’re designing systems meant to survive real-world pressure.
If you’re a founder, operator, or leader navigating growth, tech adoption, or the collision between legacy business and AI, this conversation will feel familiar in the best way.
Follow Taking Chances, share this episode with someone building alongside you, and stay close. These conversations are just getting started.