Most Challenging Sale Story

Shelby recounts closing a throuple, preempting objections, and sincere closing to win unconventional deals.

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We’re not failing at life. We were just never taught how to speak up, handle rejection, and confidently ask for what we want.

Today, Jay sits down with sales leader and entrepreneur Shelby Sapp to unpack why sales isn’t about convincing others, but about understanding people, building trust, and believing in yourself. Shelby shares how the skills that helped her go from door-to-door sales to building a thriving business are the same skills we use every day: advocating for ourselves, navigating rejection, and communicating our value. She reframes sales as a mindset shift, from seeing “no” as failure to seeing it as feedback, explaining why learning how to sell is really about learning how to think, speak, and lead with confidence.

Jay and Shelby break down the core principles that make sales applicable to every area of life: identifying leverage, creating real value, keeping things simple, and having the courage to ask for what you want. Shelby explains why people don’t buy products, they buy solutions, outcomes, and relief and how rejection becomes easier when you stop taking it personally.

They also dive into the deeper mindset shifts that separate those who stay stuck from those who grow. Shelby challenges the idea that confidence comes before action, revealing instead that confidence is built by doing uncomfortable things repeatedly and overcoming rejection. Jay reflects on how sales skills teach resilience, the ability to keep showing up with belief even after setbacks, and why handling rejection well can unlock opportunities in every part of life.

In this interview, you'll learn:

How to Sell Without Feeling Manipulative

How to Communicate Your Value Clearly

How to Handle “No” Without Taking It Personally

How to Ask for What You Want (and Get It)

How to Identify What Truly Motivates People

How to Stop Overexplaining and Keep It Simple

How to Create Momentum When You Feel Stuck

Progress isn’t about perfection, it’s about momentum. Trust yourself enough to ask, to act, and to keep going. The skills you build today will shape the confidence, freedom, and purpose you step into tomorrow.

With Love and Gratitude,

Jay Shetty

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What We Discuss:

00:00 Intro

01:23 You’re Already Using Sales in Your Every Day Life

02:53 The Power of the Reframe

04:42 The Core Sales Skills Everyone Needs

08:03 Sales Isn’t Manipulation, It’s Emotional Leadership

12:59 One Connection Can Change Everything