Real Returns

S7 E6 - Vishal Gupta | Why Every Hiring Mistake Made Me Better


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What happens when a number-crunching engineer discovers his biggest mistakes all have one thing in common?

In this episode of Real Returns, hosts Andrew Reichert and Dan Croce sit down with Vishal Gupta, tech entrepreneur and former CEO of Seclore, to explore his 25-year journey from IIT Bombay to building global cybersecurity companies serving clients like American Express, GM, and Aramco across 35 countries. Vishal reveals why angel investing became his most expensive hobby, the critical transition from engineering logic to leadership empathy, and how holding onto the wrong people too long taught him more than any success ever could. From raising capital to landing contracts bigger than funding rounds, Vishal shares his investment philosophy centered on three filters: people you enjoy working with, technology with transformative potential, and impact that matters. Learn why AI will make people more important (not less), how saving 5-7% of global manufacturing waste could reshape entire industries, and what gets Vishal energized every morning about making the digital world a safer place for everyone, especially the elderly vulnerable to cybercrime.

Timestamps:

00:00 - Opening Segment

01:00 - Vishal's Background: From IIT Bombay to Global Tech Entrepreneur

02:55 - The Expensive Hobby of Angel Investing

04:00 - The Biggest Lessons: Every Mistake Was About People

05:15 - Why Hiring Mistakes Are Getting More Expensive in the AI Era

07:10 - From Engineer to Leader: Logic to Empathy

09:00 - Why People Problems Don't Follow Engineering Formulas

10:10 - Investment Criteria: People, Technology, Impact

13:00 - Real Impact Examples: Manufacturing Waste and Cybersecurity

15:50 - Making the Digital World Safer

17:00 - Lightning Round: Customer Contracts as Funding, Ethiopian Food, and Sleep

20:10 - Content Recommendations and Young Entrepreneur Energy

22:10 - Closing Segment

Key Quote: "I went from a number crunching engineer to, I would say, a pretty people oriented leader..." - Vishal Gupta

Connect with Vishal Gupta: LinkedIn: https://www.linkedin.com/in/jiguptaji/

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Real ReturnsBy Andrew Reichert