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The Advanced Selling Podcast

Bill Caskey and Bryan Neale: B2B Sales Trainers
The Advanced Selling Podcast
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1133 episodios

  • The Advanced Selling Podcast

    20 Years In — Our Honest Regrets

    15/09/2026 | 19 min
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    Twenty years ago, Bill and Bryan started recording a podcast every other Monday. They never missed the behavior — and that consistency turned out to matter more than talent, luck, or a growth strategy ever did.
    To kick off ASP's 20th anniversary celebration, Bill and Bryan share the first of several listener tribute clips — this one from Scott, a longtime Insider member and one of the "Globetrotters," a small accountability group that formed out of the show. Scott's story becomes the jumping-off point for a bigger conversation: why "relationship selling" is mostly a myth, and what actually creates lifelong client relationships (hint: it's not golf outings).
    Bill and Bryan also get honest about regrets — the choices that kept ASP niche and steady instead of chasing bigger growth, why they never built a true listener community, and the lane they might explore next.
    The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider
    If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin
    Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com
  • The Advanced Selling Podcast

    How to Sell Something the Market Isn't Ready For

    31/08/2026 | 20 min
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    Got something genuinely new to sell — and buyers keep lumping it in with every other "revolutionary" pitch they've heard this month? This one's for you.
    Bill and Bryan work through a real scenario: a friend building software that could transform hospital billing, but can't get CFOs past their skepticism. The fix isn't a better pitch — it's a completely different approach to who you target and how you position the offer.
    You'll learn how to sort prospects by tolerance for change (not company size), why positioning your offer as limited and selective beats "revolutionizing everything," and why acknowledging buyer skepticism up front builds more trust than any pitch could.
    It's the 20th anniversary of the show, and Bill and Bryan want to hear from you — send a short voice memo to listener@advancedsellingpodcast.com for their September anniversary celebration.
    The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider
    If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin
    Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com
  • The Advanced Selling Podcast

    It's Not a Skill Problem, It's an Identity Problem

    24/08/2026 | 23 min
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    Why do good sellers freeze up the second a conversation moves from a director-level buyer to the CFO? It's not a skills gap — it's identity. Bill Caskey and Bryan Neale break down why sellers resist doing new things, even when they know exactly what it's costing them.
    Bryan shares what happened when he volunteered to try something brand-new outside of sales — nervous, uncomfortable, and more locked-in than he's felt in years. 
    That leads into why "just say this instead" coaching doesn't work, why the block that keeps a rep out of the CFO's office (or a $400K advisor from becoming a $1M advisor) is about identity, and a simple reframe for calling on anyone above your comfort level: find what's the same before you worry about what's different. 
    It's the 20th anniversary of the show, and Bill and Bryan want to hear from you — send a short voice memo to listener@advancedsellingpodcast.com for their September anniversary celebration.
    The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider
    If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin
    Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com
  • The Advanced Selling Podcast

    Stop Blaming Price: Positioning Is Your Problem

    10/08/2026 | 16 min
    Send us Fan Mail
    You didn't lose that deal on price. You lost it because your positioning wasn't strong enough to make you the obvious, can't-do-without-you choice.
    Bill and Bryan dig into a claim that gets argued in every sales meeting: is price really the reason deals slip away, or is it a symptom of weak positioning? They walk through a real audit of lost deals — 22 gone in six months, four of them deals that should have been won — and use it to unpack what separates a vendor from a "we can't do without you" partner.
    You'll learn the four ingredients of unshakeable positioning: naming the beliefs your customer has to shift before your value can land, getting explicit about what you don't do, choosing whether you're a problem-solver or a destination (or both), and painting the real cost of standing still. Plus, why the best time to build this is when business is good — not when you're desperate.
    It's the 20th anniversary of the show, and Bill and Bryan want to hear from you — send a short voice memo to listener@advancedsellingpodcast.com for their September anniversary celebration.
    The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider
    If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin
    Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com
  • The Advanced Selling Podcast

    Lessons We've Learned From Those We've Lost

    03/08/2026 | 17 min
    Send us Fan Mail
    Every person you've worked with has a story you probably never asked about — and sometimes you don't find out until it's too late.
    In Part 2 of their series on the people of sales, Bill and Bryan honor a handful of people who shaped their careers — a neighbor and airline pilot, a mentor who connected without ego, a customer who never delayed a decision, and a prospect Bryan gave up on too soon. 
    Each story carries a lesson you can use this week: ask people about their actual lives, don't wait to reconnect with old friends, decide fast, and don't give up on a prospect after just one or two tries.
    It's the 20th anniversary of the show, and Bill and Bryan want to hear from you — send a short voice memo to listener@advancedsellingpodcast.com for their September anniversary celebration.
    The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider
    If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin
    Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com
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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.
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