What if the best sales conversation you ever had ended with someone telling you NOT to buy?

That's exactly what happened when Jamie met Jill Esplin nine years ago. Jamie booked a consult for a mastermind program, and Jill—who was conducting the sales call—said something Jamie had never heard before: "Jamie, it doesn't sound like this is really what you want. This doesn't sound like it's for you."

Instead of pushing the sale, Jill recommended a completely different program that wasn't even affiliated with her company. Why? Because she had Jamie's highest interest in mind.

That conversation changed everything. A year later, Jamie was on another call with Jill for a different program (an in-person retreat). This time? Jill DID sell her. And they've been dear friends ever since.

Jill Esplin is the most masterful salesperson Jamie has ever met. She works with some of the biggest thought leaders in the industry, helping them convert their funnels, train their sales teams, and navigate what's actually working in 2026.

In this incredibly practical episode, Jill shares:

• The #1 reason people aren't converting (and it's not what you think)
• Why you need to text people from your personal phone (yes, really)
• The rule of three for follow-ups
• What to do when your launch feels like crickets
• Why a founder should ALWAYS outsell a salesperson
• Why non-attachment matters (but commitment matters more)
• The questions to ask when people don't buy

If you've ever felt "salesy," avoided following up, or watched a launch feel like crickets—this episode will change how you think about sales forever.

Meet Jill Esplin:
Jill Esplin is a sales expert with over 15 years of experience in the coaching and thought leadership industry. She works with founders, coaches, and course creators to audit sales funnels, train sales teams, and increase conversions.

She's also Millie's godmother (Jamie's maltipoo) and saw Millie before Josh even did—the most important title, according to Jill.

Connect with Jill:

• Email: [email protected] 
• Reach out through Jamie for an introduction
• Services: Sales funnel audits, limiting belief work around selling, training to become a better salesperson

Jill's specialty: Working with people who want to overcome limiting beliefs around selling, audit their sales funnel, or become better salespeople.

Check out this and recent episodes here.

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