Jaspreet Singh: Why Most People Stay Broke (Follow THIS 7-Step System to FINALLY Stop Living Paycheck-to-Paycheck!)

2026-01-19

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Money doesn’t define you, it reveals what you value, what you understand, and whether your choices are leading to freedom or confinement. Jay sits down once again with entrepreneur and financial educator Jaspreet Singh for a comprehensive conversation about money, mindset, and the systems that quietly shape our financial realities. Jay opens up about how success, comparison, and social pressure distort our relationship with wealth, while Jaspreet challenges the idea that financial struggle is purely personal failure. Together, they unpack why so m...

Money doesn’t define you, it reveals what you value, what you understand, and whether your choices are leading to freedom or confinement.

Jay sits down once again with entrepreneur and financial educator Jaspreet Singh for a comprehensive conversation about money, mindset, and the systems that quietly shape our financial realities. Jay opens up about how success, comparison, and social pressure distort our relationship with wealth, while Jaspreet challenges the idea that financial struggle is purely personal failure. Together, they unpack why so many people work hard yet feel stuck, caught in a cycle they were never taught how to escape, and why the first step to financial freedom isn’t earning more, but really understanding the rules of money.

Jay and Jaspreet lay out a clear, practical framework for building financial stability, from redefining money as a tool rather than a measure of self-worth, to understanding debt, investing, and the habits that keep people broke. Jaspreet breaks down complex ideas into simple, actionable steps, emphasizing the importance of having emergency savings, intentional spending, and long-term ownership over short-term appearances.

Together, they explore how artificial intelligence is accelerating inequality between those who understand it and those who ignore it, and why learning to use AI is becoming essential across every industry. Rather than chasing fast money or quick wins, they encourage listeners to focus on education, adaptability, and patience, building systems that serve their values, protect their families, and create lasting impact.

In this interview, you'll learn:

How to Break the Paycheck-to-Paycheck Cycle

How to Treat Money as a Tool, Not Your Identity

How to Build a $2,000 Safety Net Fast

How to Separate Spending, Saving, and Investing

How to Use AI to Get Ahead at Work and in Business

How to Build Wealth Without Chasing Fast Money

If money has ever felt overwhelming, confusing, or out of reach, this is your reminder that nothing is “wrong” with you, you were simply never taught the rules. Small decisions, repeated consistently, have the power to change not just your finances, but the way you see your future.

Want smarter money insights without the noise? Sign up for Jaspreet’s free Market Briefs newsletter and get bonus access to his investing masterclass here:

https://briefs.finance/c2ebdb

With Love and Gratitude,

Jay Shetty

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What We Discuss:

00:00 Intro

01:25 Are You Stuck Living Paycheck to Paycheck?

07:26 The Illusion of Looking Rich While Being in Debt

18:37 What is the First Thing You Should Cut to Start Saving Money?

27:13 The Fastest, Most Realistic Way to Make More Money

32:47 How to Become Revenue-Generating at Work or in Business

34:31 Start by Solving a Problem You Already Understand

39:03 How to Start Investing (Even With Little Money)

45:13 Begin With the Easiest Investing Option Available

46:43 How the Stock Market Really Works