The Digital Executive

In this episode of The Digital Executive Podcast, host Brian Thomas speaks with Adam Cohen-Aslatei, CEO of 3 Day Rule, about how technology and personalized matchmaking are reshaping modern relationships. Drawing on more than 17 years in the dating industry, Adam explains why traditional dating apps often encourage superficial connections, endless swiping, and a paradox of choice rather than meaningful relationships. He shares 3 Day Rule’s intentional three-day dating framework, which helps people identify core values, improve communication, and build genuine connections. Adam also discusses the company's AI-powered matchmaking app, which combines 16 years of matchmaking data and more than 60,000 successful matches with voice-based conversations and post-date feedback. He believes the future of dating lies in combining AI's scalability with human insight to make authentic, lasting connections more accessible.

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In this episode of The Digital Executive Podcast, host Brian Thomas speaks with Hassan Luwalira, founder and CEO of Unwilderd, the company behind Caira, an AI-powered legal product designed to make legal support more affordable and accessible. Inspired by his own experience representing himself in court, Hassan explains how he transformed a personal challenge into a mission to help others navigate complex legal matters without exhausting their life savings. He discusses how Caira differs from general-purpose AI tools through jurisdiction-specific legal documents, retrieval-augmented generation, and consistent, carefully grounded responses. Hassan also highlights the importance of educating users, addressing confirmation bias, and recognizing AI's limitations in high-stakes situations. Looking ahead, he envisions a hybrid legal system where AI and human professionals work together to expand access to justice worldwide.

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In this episode of The Digital Executive Podcast, host Brian Thomas welcomes back Charles Lambert, former CIO and founder of ITOMAC and OpsAlign, to explore why IT operations is so often the underfunded afterthought, and what that neglect quietly costs the business. Charles traces a career from Citibank in the 1980s through Cricket Wireless, AT&T, TruConnect, and Afiniti, and describes a pattern that repeated everywhere he went: budgets flowed to features, infrastructure, and AI models, while operations got whatever was left. Meanwhile, sales and retail leaders would quietly pull him aside to vent that customers were finding technology problems before IT did. That frustration led him to consult from the outside, and then to turn his own methodology into OpsAlign, a business intelligence platform for IT operations.

He explains why OpsAlign complements rather than replaces monitoring, ITSM, and observability tools. Dashboards may be green, but they cannot reveal underutilized tools, overlapping licenses, CMDBs disconnected from real services, untested disaster recovery, or thirty-year-old systems that only one soon-to-retire person understands. OpsAlign captures what the people doing the work already know across fifteen operational domains, runs it through proprietary risk range models, and converts it into dollar-quantified exposure that a CFO or board can challenge and trust. It then breaks the findings into prioritized remediation plans, roadmaps, and suggested KPIs and SLAs, while accounting for workforce factors such as distributed teams and inherited organizations.

Charles closes with a clear warning about AI: it will reward organizations whose operations are well understood and punish those that are not, because automation on top of bad processes and bad data simply makes bad outcomes happen faster. His advice is to assess first, assess regularly, bring in evidence rather than instinct, and keep watching for drift and governance gaps long after the first improvements land.

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In this episode of The Digital Executive Podcast, host Brian Thomas speaks with Sachin Gupta, an enterprise technology leader and digital transformation strategist with more than 20 years of experience, about the future of agentic AI and intelligent supply chains. Sachin explains how enterprises can evolve beyond traditional ERP systems by combining ERP as the system of record, AI as the system of intelligence, and autonomous workflows as the system of action. He explores how this approach can improve supply chain resilience, accelerate decision-making, and reduce operational bottlenecks. Sachin also emphasizes that responsible AI adoption requires built-in governance, clear decision ownership, cybersecurity, and human oversight for high-impact decisions. He shares three priorities for building trustworthy enterprise systems: reliable master data, defined risk controls, and small, measurable use cases that can scale.

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In this episode of The Digital Executive Podcast, host Brian Thomas speaks with Dr. Arash Bereliani, board-certified cardiologist and medical director of the Beverly Hills Institute for Cardiology and Preventative Medicine, about the critical gaps in women's heart health. Dr. Bereliani explains how decades of male-centered medical research have contributed to missed symptoms, overlooked risk factors, and inadequate treatment for women. Drawing on more than 20 years of preventative cardiology experience, he highlights the importance of recognizing women's unique symptoms, understanding the impact of chronic stress and sleep, and monitoring key cardiovascular health indicators. He also shares why prevention must begin before symptoms appear and how sex-specific research, personalized testing, AI, and advanced medical imaging could transform the future of women's heart care.

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