Dennis Kao
From building computers at a flea market to leading multiple successful businesses, Dennis’s journey began when he immigrated from Taiwan to the United States at the age of 10, eventually settling in Chester, Virginia. Now based in Richmond, he has spent his career helping businesses navigate the intersection of people, processes, and technology to drive growth, efficiency, and security.
As a seasoned business leader and consultant, his passion lies in helping businesses navigate and solve complex business challenges. Whether tackling operational inefficiencies, security vulnerabilities, or digital transformation hurdles, Dennis believes success is built on aligning the right people, well-defined processes, and implementing the right technology. By bringing these elements together, he enables organizations to turn obstacles into opportunities and drive sustainable growth.
A true entrepreneur at heart, Dennis has successfully launched, scaled, and exited multiple ventures—including a golf course weather alert system adopted by the PGA Tour, a HIPAA and OSHA compliance consulting firm, and two thriving medical practice turnarounds. His expertise spans industries such as medical practices, financial firms, government agencies, and private equity firms. In the private equity space, Dennis specializes in pre-and post-acquisition technology due diligence services, often serving as an interim CIO/CTO to drive post-acquisition integration and operational efficiency. He has played a pivotal role in streamlining business operations, empowering teams, and deploying transformative technologies to maximize value creation and scalability.
Fun Facts:
- Speaks four languages and two dialects fluently (English was NOT his first language!)
- Originally wanted to be a concert pianist before getting into business and technology
- Was a substitute member for the Richmond Symphony and was a member of Richmond Symphony Pops
- Five-time Ironman finisher (yes, the grueling triathlon!)
- Coaches runners for the Sports Backers Richmond Half Marathon Team – supporting Richmond’s active community
Sessions:
ÉLAN is a strategic framework designed for CEOs and business leaders seeking to build enterprise value with clarity, confidence, and intent. Rooted in the philosophy that growth and exit-readiness are not separate paths but parallel outcomes, ÉLAN guides leaders through four interconnected pillars: Explore, Lead, Accelerate, Navigate.
This methodology challenges the traditional reactive approach to business transitions by reframing success around optionality, creating businesses that can scale, transfer, or exit at the leader’s discretion. From aligning personal and financial goals to building self-sustaining leadership teams and closing strategic gaps, ÉLAN empowers leaders to transform their businesses into valuable, resilient, and market-ready assets.
At the foundation of ÉLAN is Live on Four, a clarity tool that helps leaders determine their personal “number” across four key dimensions: lifestyle, liquidity, legacy, and leverage. This framework ensures that business strategy is anchored in personal purpose and financial reality, allowing leaders to grow with intention and exit without regret.
Whether you're planning to exit in 12 months or evolve your leadership role over the next decade, ÉLAN, powered by Live on Four, offers a practical, actionable blueprint to drive growth on your terms while protecting the legacy you’ve built.
