Andrew Bolton is a Harvard finance graduate turned entrepreneur who traded Wall Street for a more meaningful mission: making technology accessible for those most often left behind. As CEO and co-founder of Tech Rescue—named one of the top 100 US startups in 2024—Andrew built a 24/7 tech support company that serves seniors, families, and small businesses with a distinctly human-first approach. The inspiration came from his grandmother's struggles navigating social media for her genealogy hobby, which revealed a massive gap in the market. What began as family tech support evolved into a HIPAA-compliant service that helps seniors schedule medical appointments, arrange transportation, manage prescriptions, and navigate the increasingly complex digital landscape. In one retirement community, Tech Rescue reduced nursing staff incidents by 13% simply by handling technology issues, allowing medical professionals to focus on actual healthcare.

Andrew's bold perspective on technology's future centers on a critical insight: while companies rush to implement AI everywhere and eliminate human support, they're fundamentally misunderstanding consumer needs. He argues that businesses are "cannibalizing themselves" by removing phone numbers, hiding support contacts, and forcing customers through AI chatbots that deliberately waste time—shielding companies rather than serving people. Tech Rescue thrives precisely because it offers what consumers desperately want: a real human who cares about their problem. Andrew's three pillars of leadership—hire people who are good at what they do, love what they do, and believe in what you do—enable him to delegate effectively while maintaining his adventurous lifestyle exploring different cultures. His vision challenges the tech industry's obsession with automation, asserting that in an increasingly digital world, human connection becomes more valuable, not less.

00:00 Introduction: From Harvard to Tech Rescue

02:50 Growing Up in the Nineties Action Hero Era

05:00 Grandma's Tech Struggles Spark a Business Idea

08:00 The 14% Problem: Seniors Without Tech Support

10:00 When Your Washing Machine Needs Bluetooth

12:30 Post-COVID Graduates: Not Work Ready

15:00 The Future of Trade Schools and Real Skills

17:00 Why Offices Are Becoming Optional

19:00 AI as Tool vs. AI as Replacement

21:00 People as Constants, Technology as Variables

23:00 Teaching in the Age of ChatGPT

25:00 Wearable Tech and the Future of Senior Healthcare

27:00 The Three Pillars of Leadership

28:30 What Tech Founders Are Getting Wrong

32:00 AI Chatbots: Designed to Block, Not Help

33:30 Why Human Connection Will Always Matter