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
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 legendary process focus, this episode explores why fixating on the score is the wrong move — and what sellers and sales leaders should be analyzing instead. Bill and Bryan dig ...
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 it's your job to uncover what's actually at stake. Bill walks through the questions you need to ask to get past symptoms and find the true pain: What's the cause...
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, habits, and tools that compound over time.
In this episode, you'll hear about the gift of applying abundance thinking to your sales life, why investing in yours...
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 sales and marketing improves lead quality and eliminates the “bad lead” blame game, before diving into practical ways sellers can use AI tools like ChatGPT and Copilot to refine emai...
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 believe, and how you package your expertise so prospects say, "I want to know more."
Before diving into the March session, Bill and Bryan walk through the perspe...
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 networking, early conversations, mid-stage resistance, and closing deals. You'll discover why most salespeople avoid collaboration (they're afraid of conflict), how to audit your sales p...
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 happens when tools are finally built with field sellers in mind.
Bryan and Steve dig into the realities of territory design and route planning, calling out how many sales leaders still rely on gut feel and e...
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 follow-ups, but through generous, creative demonstrations of value. He sent tracks. He added a choir. He painted the picture so vividly that Kenny G couldn't help but...
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 of selling to people who don't need what you offer, you become the guide that customers are craving.
If you've ever wondered why buyers don't trust you or why price bec...
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" philosophy and real client stories, they explore how physical action—whether it's actual exercise or the behavioral action of getting out and connecting with peo...
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 core issue: attachment to outcomes.
Discover why healthy detachment isn't about not caring—it's about being deliberate in your process without getting entangled...
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 John discuss the difference between messaging and moments, emphasizing that when the moment matters more than the message, authenticity wins. John shares the evolution of Spokenote, from a s...
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 three in depth: detachment from outcomes, obsessive focus on customer problems, and personal agency. Bill addresses a high performer's legitimate concern about whether detachment actu...
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 beyond financial gain, and how physical movement directly impacts emotional health.
If you struggle with walking on eggshells around buyers or feel desperate for outcomes, this...
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 gifts as swag or gimmicks, their conversation reframes gifting as a human-first way to build trust, strengthen relationships, and create influence.
Bryan and Patricia exp...
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 challenges: quota pressure, identity tied to numbers, comparison traps, and the constant pursuit of an unreachable horizon.
Bryan shares his panic attack story from his ...
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 conversion training, and shares practical strategies for social media content, email campaigns, and outreach that actually lead somewhere.
You'll learn how to create LinkedIn con...
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 sales success.
From defining your vision to finding the right accountability partner, Bill covers everything you need to create a plan that actually works—not just another r...
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 Planning Strategy—the piece that asks not just what you need to do, but who you need to become to achieve your goals sustainably.
Bill covers four essential areas: AI literacy a...
Last week, Bill and Bryan covered mental discipline—getting your head right. This week, they shift to operational discipline: the actual behaviors and systems that high performers use to win.
This isn't about overhauling your entire life. It's about looking at your current operational system and asking: Is this working? If yes, keep rolling. If not, tweak and modify.
Bill and Bryan break down five operationa...
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