#467 From Engineer to Entrepreneur: Tom Basey on Reinventing Career Paths Through Insurance & Impact

In this episode of The CTO Show with Mehmet, we sit down with Tom Basey, a former engineer and project manager turned entrepreneur, to unpack what it really takes to pivot from corporate life to a lean, scalable business in an unexpected space—insurance. Tom shares lessons from 30+ years in tech and telecom, why he believes insurance is a smart entry point for aspiring entrepreneurs, and how he’s leveraging digital tools and AI to scale impact without the traditional overhead.

🔑 Key Takeaways

• Why simplicity and execution often outperform innovation

• How to build a scalable business with no payroll or supply chain

• The overlooked power of insurance as a lean startup model

• What Web3 and blockchain can teach us about ownership and decentralization

• Why lifelong learning and digital mentorship are the future of education

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📚 What You’ll Learn

• How corporate experience can prepare you for entrepreneurship

• The pros and cons of entering a crowded market

• What “doing the work once and getting paid repeatedly” looks like

• Real-life use cases for blockchain in fraud prevention, insurance, and creator economy

• How to rethink traditional education in an AI-first world

👤 About the Guest

Tom Basey is a self-described “recovering engineer” who spent decades in corporate America before launching a successful entrepreneurial career in the insurance industry. Drawing from his background in engineering, telecom, and medical devices, Tom now helps people secure their futures through insurance, while mentoring others on digital learning and distributed ownership.

https://www.basey-insurance.com/

https://www.linkedin.com/in/tombasey/

⏱️ Episode Highlights

00:00 – Tom’s journey: from engineering to entrepreneurship

03:00 – Why he chose insurance and how it scales lean

07:00 – Competing in a crowded market through consultative selling

09:00 – Incentives, recurring revenue, and trust in sales

11:00 – How AI is transforming underwriting in insurance

14:00 – Leaving corporate: mindset shifts and myths to break

18:00 – Digital learning, mentorship, and monetizing expertise

27:00 – Web3, blockchain, and decentralizing ownership

36:00 – Use cases for blockchain in insurance, identity, and tickets

41:00 – Staying human in a digital world

43:00 – Final advice: Own your future, stay curious, and keep learning

We’re proud to share that The CTO Show was recently featured by Million Podcasts as a top show across several categories:

• 100 Best Business Technology Podcasts

• 100 Best Digital Business Podcasts

• 100 Best Digital Transformation Podcasts

• 100 Best Future of Work Podcasts

• 100 Best Future Tech Podcasts

• 100 Best Startup Podcasts

Check it out here: Million Podcasts Feature