The 20-Year Horizon: How Serial Winners Build Businesses That Last

What if the key to building a tech enterprise that lasts isn't inventing breakthrough technology, but solving the right problem first? In this episode of Big Hitters with Larry Weidel, host Larry Weidel sits down with Dejan Nenov, CTO and CISO at Taichin AI and veteran entrepreneur who has helped build operating companies returning over $3.5 billion in value across chips, cybersecurity, energy, and healthcare. Dejan shares his journey from coming to the U.S. from Eastern Europe as a teenager to creating a data-driven algorithm in 1993 that helped propel a real estate firm onto the New York Stock Exchange. From navigating Silicon Valley's dot-com boom and bust to spearheading AI transformation in American healthcare today, Dejan reveals how serial winners keep winning by staying disciplined, validating market demand early, and remaining resilient when market cycles shift. Tune in to discover why fortune favors the daring, how to set strict capital guardrails, and why getting laid off overnight taught Dejan that nobody is irreplaceable.

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Building a venture during a tech hype cycle is easy; building operating companies that withstand economic shifts and return billions in value requires an entirely different level of discipline.

In this episode of Big Hitters with Larry Weidel, host Larry Weidel sits down with Dejan Nenov, CTO and CISO at Taichin AI, to discuss how he built a 30-year career co-founding and operating technology companies that have generated over $3.5 billion in return value. Dejan opens up about his formative years coming to the U.S. from Bulgaria on a high school scholarship, studying electrical engineering and computer science, and taking his first job out of college mapping mini-storage facilities with an early geographic information algorithm. That algorithm worked so well it allowed the company to list as a REIT on the New York Stock Exchange as a high-tech business in a low-tech industry.

Dejan pulls back the curtain on the core principles that have guided his success across seven different operating companies. He explains why entrepreneurs must resist the urge to invent technology first and search for a problem second, why validating go-to-market demand before building software saves millions in wasted capital, and how to maintain financial guardrails when launching new initiatives. He also shares the humbling story of the dot-com crash when an overnight market collapse canceled a major IPO and cost him his CTO role in 24 hours, a setback that shaped his philosophy on humility, staying flexible, and treating every new venture like a fresh startup.

What You'll Learn:

The "Sell Before You Build" Principle: Why you should always validate go-to-market demand and confirm a revenue model before investing heavy capital in building a product.
How to Avoid the Tech Hype Trap: How to evaluate modern breakthroughs like artificial intelligence based on net income generation rather than industry hype.
Building a Geographic Algorithm That Scaled a REIT: How Dejan mapped mini-storage locations against high schools and fast-food spots in 1993 to predict rent growth and help take a company public on the NYSE.
The 2x–3x Budget Rule: Why you should never start executing on a project until you have at least twice (or three times) your projected budget available in liquid reserves.
Why Nobody Is Irreplaceable: What getting laid off 24 hours after a high-stakes pre-IPO kickoff meeting taught Dejan about organizational reality and resilience.
Active Balance Over Static Perfection: Why life and business balance is an ongoing process of active recalibration, prioritization, and learning to say no.
Micro-Wins as Adrenaline: How capturing small daily operational wins builds the momentum needed to achieve long-term enterprise breakthroughs.

About the Guest(s):

Dejan Nenov is the Chief Technology Officer and Chief Information Security Officer at Taichin AI, bringing over 30 years of experience building and operating technology companies across chip design, cybersecurity, energy, and healthcare. Born in Bulgaria, Dejan came to the United States on a scholarship to the United World College before earning his degree in electrical engineering and computer science from Rose-Hulman Institute of Technology. Throughout his career, including 15 years in Silicon Valley, Dejan has co-founded and built operating companies alongside a tight-knit group of co-investors, returning approximately $3.5 billion in value. Early in his career, he developed a proprietary geographic information algorithm that helped take a storage real estate firm public on the New York Stock Exchange. Today, his work focuses on leveraging artificial intelligence and data analytics to optimize clinical and administrative workflows across the U.S. healthcare system.

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