The Advanced Selling Podcast

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

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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 hustle — you're operating on an old model that's nearly impossible to scale. Bill breaks down a better framework: Discover, Develop, Deploy. Find the assets you already have (client success stories, your personal story, your expertise), build the skills to use them, and put them to work in the market.
Most salespeople close 20–25% at best, which means they're burning 75–80% of their effort on people who will never buy — largely because they never leveraged anything in the process. Bill challenges you to identify where leverage is absent in your sales approach and start building a new identity around it.
🔗 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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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 people see what you're made of. From a chance encounter at a restaurant to a woman coaching a thousand people to share their stories on stage, the lesson is clear: you can't demonstrate excellence from your couch, your car, or your home office.
They also dig into what happens when people do get their moment in the spotlight — and blow it by reading from a notecard. And they share the story of Milo, door holder number three, who might have the best mindset in the room.
Get out. Get in the room. Be excellent when it counts.
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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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 being beaten down on price coming in, and how to successfully raise prices with clients you've already got. Their answer isn't a negotiation tactic — it's a positioning problem. And the fix starts long before the price conversation happens.
They cover why technical sellers tend to stay too low in the org chart, why your contact isn't selling your value upstairs for you, and what a price increase reaction tells you about where you actually stand with a client.
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