The Advanced Selling Podcast
Bill Caskey and Bryan Neale deliver practical, no-nonsense sales training through their signature blend of humor, real-world insights, and actionable frameworks. Each episode tackles the challenges you face daily: prospecting, overcoming buyer resistance, pricing strategies, cold calling, deal coaching, and building long-term client relationships.
Whether you're a sales professional, manager, or leader, you'll discover how to shift your mindset, leverage your natural talents, and create sustainable sales success. From mastering sales communication and handling RFPs to understanding buyer psychology and effective positioning, Bill and Bryan cover everything that actually works in modern B2B sales.
Episodes
1112 episodes
Why Your Calendar Is Killing Your Pipeline
What's the #1 problem facing salespeople and customer acquisition professionals right now? Bill and Bryan each share their answer — and while they come at it from slightly different angles, both point to the same root cause: the absence of a re...
Stop Being Selfish: The Sales Habit That Pays Off Later
Bill and Bryan are back from spring break with a powerful lesson about the long game in sales. Inspired by a 35-year-old charity event that grew into a $400 million movement, they dig into how the small actions you take — or skip — ...
Why Prospects Stop Trusting You (And How to Fix It)
Trust is the missing ingredient in most failed deals — and the old methods of building it (the hearty handshake, the enthusiastic follow-up email) no longer cut it. In part four of the Sales Identity Crisis series, Bill breaks down why modern b...
The Identity Shift: From Labor to Leverage
In this solo episode, Bill Caskey continues his series on the Sales Identity Crisis — specifically, the shift from being a laborer to becoming a leverager.If your sales approach is built on effort alone — more calls, more hours, more hus...
Stop Hiding. Create Space to Be Excellent.
Most salespeople wait for opportunity to come to them. Bill and Bryan flip that script.In this episode, they explore what it means to create a "space for excellence" — the rooms, events, and moments where you show up, lean in, and let pe...
Raise Your Prices Without Losing Your Clients
A listener question from William — an engineer who also sells — kicks off a focused conversation on one of the oldest problems in B2B sales: getting commoditized on price.Bill and Bryan tackle both sides of the equation: how to avoid bei...
Stop Watching the Scoreboard — Start Watching the Inputs
We're at the end of Q1 — and Bill and Bryan use a trip to the Pacers game as a launching pad for a conversation about what actually matters when you check the scoreboard.Inspired by Bill Walsh's coaching philosophy and John Wooden's lege...
Find the Real Pain Behind Every Sales Conversation
Every prospect tells you a version of their problem — and they're almost always wrong. Not lying. Just wrong.In this solo episode, Bill Caskey breaks down why the surface problem your prospect presents is rarely the real problem, and why...
The Best Sales Gifts Nobody Buys You
It's Bill's birthday — and that means one thing: it's time to talk about gifts. But not the usual Amazon cards and polka dot sweaters. Bill and Bryan dig into the sales gifts worth actually giving yourself: the mindset shifts, investments, habi...
AI as a Sales Tool, Not a Salesperson with Kayla Kurtz
In this episode of The Advanced Selling Podcast, Bryan Neale welcomes Kayla Kurtz, VP of Sales and VP of Business Development at Forthea, for a focused conversation on how AI is reshaping modern sales.Kayla shares how aligning sa...
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From Content to Conquest
Bill and Bryan are giving you a preview of the March 6th ASP Insider session — and it's one you don't want to miss.The topic is From Content to Conquest, but this isn't a social media training. It's about what you know, what you...
Why Collaboration Beats Closing Tactics Every Time
What if your entire sales process—from networking to contract signing—was built on collaboration instead of persuasion? In this episode, Bill and Bryan break down what real collaboration looks like at every stage: pre-sale networkin...
Saving Sales Time with Smarter Routes ft. Steve Benson
In this episode of The Advanced Selling Podcast, Bryan Neale welcomes Steve Benson, founder of Badger Maps, for a conversation on why outside sales teams are often overlooked by modern sales technology — and what happe...
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Is Your Through Line Costing You Business?
What can Charlie Puth's collaboration with Kenny G for the Super Bowl national anthem teach us about sales? More than you'd think.Bill and Bryan break down the story of how Charlie Puth persistently pursued Kenny G—not through aggressive...
Be the Guide Your Customers Are Craving
Bill Caskey explores the most important question in sales: What is your role in the buyer-seller dance?In this solo episode, Bill breaks down the Guide Model—a three-part framework that transforms how you show up with customers. Instead ...
Mental Health in Sales: Movement Creates Momentum
In the final episode of our mental health in sales series, Bill and Bryan tackle a truth most sellers ignore: you can't think your way out of a slump—you have to move your way out.Drawing from Scott Galloway's "get out of the house" phil...
How Detachment Creates Sales Freedom
In this solo episode, Bill breaks down why detachment might be the most important skill you're not practicing. When a client asked for help with negotiation, positioning, and value communication, Bill realized all these challenges stem from one...
Scaling Authenticity in Sales with John Wechsler
In this episode of The Advanced Selling Podcast, Bryan Neale is joined by John Wechsler, CEO of Spokenote, for a conversation on why authentic, personalized video is becoming a critical advantage for modern sales teams.Bryan and J...
Mental Health in Sales: Detachment, Service and Personal Agency
In part 3 of the mental health series, Bill and Bryan tackle the achievement trap that plagues high performers: when is enough enough? They introduce six practical frameworks for managing mental health in sales, covering the first t...
Mental Health in Sales: Confidence, Purpose and Movement
In part 2 of our mental health series, Bill and Bryan explore what creates genuine confidence in sales and why it starts with something bigger than yourself. They discuss the "divine assignment" concept, finding meaning in your work...
Strategic Gifting with Patricia DuChene
In this episode of The Advanced Selling Podcast, Bryan Neale is joined by the VP of Growth and Marketing at Sendoso, Patricia DuChene, to discuss how intentional gifting can be used as a strategic tool in modern sales. Rather than treating gift...
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Mental Health in Sales: Breaking the Silence
Bill and Bryan launch a vital series on mental health in sales—a topic that's rarely discussed but critically important. After Bill's month-long absence dealing with family tragedies, they dive into why salespeople face unique mental health cha...
Building a Sales Engine Framework
In this solo episode, Bill introduces the Complete Sales Engine Framework, focusing on the first two essential blocks: Attention and Engagement. He breaks down why most companies struggle with empty pipelines despite focusing heavily on convers...
The 9-Block Business Planning Framework for 2026
Bill Caskey breaks down the exact business planning framework from the recent ASP Insider workshop. If you haven't done your 2026 planning yet, this episode walks you through nine critical building blocks that will set you up for sustainable sa...
The Missing Block in Your Business Plan
Most business planning workshops start with vision statements and call quotas. But Bill argues there's a critical block missing from that equation: personal development. In this solo episode, he breaks down Block 8 from his 2026 Business Planni...
