In this episode of Sales & Cigars, Walter Crosby sits down with Nick Massaro of Membrane for a candid, no-BS conversation about what actually holds good salespeople back. From early sales foundations and structured training to the mindset traps that quietly derail deals, this episode digs into the space between opening and closing—the part most reps avoid and where deals are truly won or lost.

Nick shares his journey into sales, the evolution of his mindset, and the hard-earned realization that being "the most liked rep" is often a sign something went wrong. Together, they unpack the dangers of approval-seeking, why discomfort is part of great selling, and how modern buyers require a different kind of leadership from sales professionals.

This is a grounded, honest conversation for salespeople who want to stop getting compliments instead of contracts.

Episode Highlights

Why "You were the best rep" is often a kiss of death
The difference between opening deals and advancing them
How early structure shaped Nick's sales foundation
The mindset shift required to lead buyers without controlling them
Why avoiding money conversations quietly kills deals
Selling outcomes vs. selling features—especially in complex software
Letting go of approval to ask better questions
What great sales and good parenting surprisingly have in common

Key Takeaways

Being liked doesn't equal being effective
The middle of the deal—not the open or close—is where salespeople grow
Approval-seeking prevents tough (necessary) conversations
Buyers are in control—but salespeople must still lead
Discovery isn't about sounding smart; it's about creating clarity
Authenticity beats polish every time
Process creates freedom, not rigidity

Who Should Listen

This episode is for:

Salespeople who hear "we loved you" more than "we're buying"
Reps who love prospecting but struggle with deal momentum
Sales leaders coaching mindset, not just activity
Anyone selling complex or non-commodity solutions
Business owners trying to understand what their sales team is really up against

About the Guest

Nick Massaro is a sales professional at Membrane with a background spanning insurance, SaaS, and sales-as-a-service environments. Known for his authenticity and curiosity, Nick brings a thoughtful perspective on modern selling—one rooted in structure, accountability, and continuous improvement.

Connect with Nick

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Keep savoring those cigars and stay sharp in sales! Until next time, keep listening to Sales & Cigars—the podcast where the only smoke we blow is from cigars.

The Approval Trap: Why Being Liked Can Kill the Deal