The Advanced Selling Podcast
Business & Finance
About
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
- 7 Lies About Sales Success
Send us Fan Mail What if the beliefs driving your sales career are built on a foundation of lies? In this solo episode, Bill Caskey breaks down seven deeply normalized lies about achievement, income, and sales success — the kind that quiet…
- How to Become the Obvious Choice (Part 2)
Send us Fan Mail Bill Caskey and Bryan Neale continue their series on how to become the Obvious Choice for your prospects and customers — not by closing harder, but by selling smarter throughout the entire process. In Part 2, they cover fo…
- Becoming the Obvious Choice (Part 1)
Send us Fan Mail How do you become the vendor your customers never even think to replace? In Part 1 of this short series, Bill and Bryan break down what it actually takes to become the obvious choice — not through last-minute discounts or…
- The Fear Factor in Sales
Send us Fan Mail Fear shows up at every stage of a sales career — first calls, big promotions, major presentations, and yes, posting on LinkedIn. In this episode, Bill and Bryan dig into how fear works, why your brain treats a LinkedIn pos…
- The Simple Shift That Changes Every Sales Conversation
Send us Fan Mail Are you walking into sales calls without getting clear on the actual problem you're solving? In this episode, Bill and Bryan dig into one of the most overlooked fundamentals in B2B sales: defining the real problem before p…
- Why Your Calendar Is Killing Your Pipeline
Send us Fan Mail 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 caus…
- Stop Being Selfish: The Sales Habit That Pays Off Later
Send us Fan Mail 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 —…
- Why Prospects Stop Trusting You (And How to Fix It)
Send us Fan Mail 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 br…
- The Identity Shift: From Labor to Leverage
Send us Fan Mail 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…
- Stop Hiding. Create Space to Be Excellent.
Send us Fan Mail 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, lea…
- Raise Your Prices Without Losing Your Clients
Send us Fan Mail 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:…
- Stop Watching the Scoreboard — Start Watching the Inputs
Send us Fan Mail 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 Jo…
- Find the Real Pain Behind Every Sales Conversation
Send us Fan Mail 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…
- The Best Sales Gifts Nobody Buys You
Send us Fan Mail 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 shi…
- AI as a Sales Tool, Not a Salesperson with Kayla Kurtz
Send us Fan Mail 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 al…
- From Content to Conquest
Send us Fan Mail 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,…
- Why Collaboration Beats Closing Tactics Every Time
Send us Fan Mail 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…
- Saving Sales Time with Smarter Routes ft. Steve Benson
Send us Fan Mail 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…
- Is Your Through Line Costing You Business?
Send us Fan Mail 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 th…
- Be the Guide Your Customers Are Craving
Send us Fan Mail 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 cus…
- Mental Health in Sales: Movement Creates Momentum
Send us Fan Mail 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…
- How Detachment Creates Sales Freedom
Send us Fan Mail 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 ch…
- Scaling Authenticity in Sales with John Wechsler
Send us Fan Mail 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. Br…
- Mental Health in Sales: Detachment, Service and Personal Agency
Send us Fan Mail 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 t…
- Mental Health in Sales: Confidence, Purpose and Movement
Send us Fan Mail 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…
- Strategic Gifting with Patricia DuChene
Send us Fan Mail 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. Rat…
- Mental Health in Sales: Breaking the Silence
Send us Fan Mail 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 un…
- Building a Sales Engine Framework
Send us Fan Mail 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 focus…
- The 9-Block Business Planning Framework for 2026
Send us Fan Mail 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…
- The Missing Block in Your Business Plan
Send us Fan Mail 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 hi…
- From Thinking to Doing: Operational Disciplines That Work
Send us Fan Mail 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 y…
- The Mental Game: Building Discipline That Actually Works
Send us Fan Mail Bill and Bryan tackle mental discipline—but not the way you'd expect. Instead of rigid rules and forced habits, they reframe discipline as the inputs that create freedom, not constraints. In this first part of a two-part s…
- Sales Compensation with Chris Goff
Send us Fan Mail In this episode of The Advanced Selling Podcast , Bryan Neale sits down with sales compensation expert Chris Goff, better known across the industry as “ The Sales Comp Guy. ” With deep experience in sales operations, terri…
- Micro Mastery: Small Skills That Create Big Results
Send us Fan Mail Part two of our macro vs. micro skills series—and this one gets tactical. Bill and Bryan dive into the small, incremental skills that most salespeople overlook but that separate pros from amateurs. These aren't the big-pic…
- Your Most Powerful Pre-Meeting Asset
Send us Fan Mail Most salespeople waste their first meeting covering basics that could've been handled beforehand. Bill introduces a game-changing digital asset: the introductory video—a 5-minute pre-meeting video that positions you as a c…
- Macro vs. Micro: Sales Skills That Actually Matter
Send us Fan Mail Bill and Bryan break down the difference between macro and micro sales skills—and why both matter more than you think. Inspired by a prospect who called out his own team for not asking clarifying questions, this episode ex…
- Beyond Process: The Courage to Walk Away
Send us Fan Mail Bill Caskey follows up on last week's deep dive by sharing insights from coaching a high-performing salesperson who's hitting the limits of process-driven selling. He reveals why even the best sales process isn't enough—yo…
- Vince Beese: Red Zone
Send us Fan Mail In this episode of The Advanced Selling Podcast , Bryan Neale sits down with longtime friend and sales veteran Vince Beese , a fractional CRO and sales coach with over 25 years of B2B enterprise experience and five success…
- "Let's Talk Money" 5 Scenarios Sales Reps Struggle With
Send us Fan Mail Are you uncomfortable talking about money with prospects? You're not alone. In this episode, Bill and Bryan tackle one of the biggest challenges sales professionals face: bringing up price, cost, and economic conversations…
- Building a Winning Sales Culture (Part 2)
Send us Fan Mail In this episode, Bill and Bryan continue their conversation on sales culture with actionable tactics you can implement immediately. Whether you're building team culture or your personal approach, these strategies will help…
- The Invisible Dimension of Sales
Send us Fan Mail Bill Caskey poses a challenging question: If you disappeared from your prospect's world tomorrow, would they feel the loss? In this introspective solo episode, he explores the "invisible dimension" of sales—the deeper leve…
- Connect With Customers
Send us Fan Mail In this episode, Bryan Neale from Blind Zebra shares a tactical framework for building meaningful customer connections — one rooted in strategy, generosity, and intentional networking. He explains why great salespeople mov…
- What Sales Culture Really Is (And Why It Matters)
Send us Fan Mail Bill and Bryan kick off a two-part series on sales culture by sharing what they've observed from years of working inside dozens of organizations. In this episode, they explore the difference between surface-level culture (…
- AI in Sales (Part 2): Pre-Call Research and Content Creation
Send us Fan Mail In part two of their AI series, Bill and Bryan get specific—sharing real examples of how they use AI in their daily sales work. Bill walks through actual ChatGPT conversations for client prep (including a memorable moment…
- Connect With Your Team
Send us Fan Mail In this episode, Bryan explores why the best sales leaders focus as much on connecting with their people as they do on connecting with their customers. Sales is often seen as an individual sport - everyone chasing their ow…
- AI in Sales (Part 1): Practical Uses for Prep, Research, and Productivity
Send us Fan Mail Bill and Bryan dive into how they're actually using AI in their daily sales work—no hype, just practical applications. In part one of this two-part series, they share their number one use case: preparation for sales calls,…
- Stop Discounting - Closing Strategies with John Barrows
Send us Fan Mail In this episode, Bryan is joined by John Barrows to talk about the high-stakes final stage of the sales process, where deals are either won or lost. Together, they explore why so many sales teams stumble here, often resort…
- Stop Being the Best-Kept Secret: How to Get Found by Your Ideal Clients
Send us Fan Mail Tired of perfecting your sales skills but struggling to get in front of the right people? Bill and Bryan tackle the universal challenge every B2B professional faces: visibility. Using a real client case study from the tax…
- The Myth of Creating Buyer Urgency
Send us Fan Mail In this episode, Bill and Bryan debunk one of the most persistent myths in sales training - that you can create urgency in buyers through clever tactics and techniques. They explore why deals are taking longer to close in…
- The Rise of Accidental Salespeople
Send us Fan Mail Bill and Bryan explore a growing trend that's reshaping the sales landscape: the rise of "accidental salespeople." These are the technical advisors, project managers, engineers, and executives who don't have "salesperson"…