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The Advanced Selling Podcast

The Advanced Selling Podcast

By: Bill Caskey and Bryan Neale: B2B Sales Trainers
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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.

© 2026 The Advanced Selling Podcast
Economics Marketing Marketing & Sales Personal Development Personal Success
Episodes
  • Why Your Calendar Is Killing Your Pipeline
    Apr 27 2026

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    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 real system.

    Bryan breaks down why time misallocation kills pipelines, and Bill makes the case that lead generation is the core issue most companies struggle to solve — not because of effort, but because they're relying on activity instead of architecture.

    The guys walk through practical examples of what a real lead gen system looks like: calendar blocking that actually holds, consistent outreach cadences that generate 1-in-5 conversations, and leverage-based content strategies that let buyers raise their hand instead of being cold-called into a corner.

    If your sales are inconsistent, your calendar is the first place to look.

    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

    If your offer isn't closing deals, this is your fix — Save your seat for May 1st at advancedsellingpodcast.com/insider

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    20 mins
  • Stop Being Selfish: The Sales Habit That Pays Off Later
    Apr 20 2026

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    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 — today create enormous downstream outcomes you can't predict.

    They challenge sellers to stop making excuses, stop being selfish with their knowledge, and start showing up consistently — on LinkedIn, in the field, and with their prospects — because someone out there might be suffering simply because they haven't heard from you yet.

    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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    15 mins
  • Why Prospects Stop Trusting You (And How to Fix It)
    Apr 9 2026

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    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 buyers are slow to trust and offers a counterintuitive fix: create content.

    Bill shares how consistent content — podcasts, video, written pieces — lets prospects sample your thinking long before a sales conversation begins. When they finally reach out, they're already sold. He also challenges the habit of chasing prospects for next steps, arguing that if you're the one pushing, something went wrong earlier in the process.

    🔗 Want more advanced sales training? Join ASP Insider: https://advancedsellingpodcast.com/insider

    Download your complimentary copy of the 12 Bold Moves audiobook at 12BoldMoves.com/Audiobook

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    6 mins
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