Entries by Bill Caskey

The Joy of Selling: 5 Ways to Remove the Struggle from Sales

In this episode, Bill challenges the notion that selling has to be a struggle. Inspired by Stuart Wild’s philosophy, Bill shares five transformative principles that can make selling not just easier, but more fulfilling. From detaching from outcomes to mastering curiosity, he reveals how modern sales professionals can shift from the outdated “convince and persuade” […]

Revenue Mastery (Part 3 of 3)

In this conclusion to the Million Dollar Seller Roadmap series, Bill Caskey reveals the final three steps to truly maximize your revenue potential. Learn how to pour gasoline on your foundation and interaction strategies with these game-changing approaches: Landing Larger Accounts: Discover how to position yourself as a thought leader and create powerful assessment tools […]

The Key Interactions (Part 2 of 3)

Building on the foundation from Part 1, discover the three key steps that will transform how you connect with prospects and convert opportunities: Pipeline Building: Learn why cold outreach isn’t your only option and how to create systems that generate leads while you sleep Asset Leveraging: Unlock the hidden potential in your existing network and […]

Building the Foundation (Part 1 of 3)

Want to dramatically scale your revenue in 2025? In this first episode of our three-part series, Bill Caskey breaks down the crucial foundation stage of the Million Dollar Selling Method. Bill shares the first three steps to transforming your sales approach: Million Dollar Mindsets: Discover the game-changing perspective of detachment and unlock your true potential […]

Your First 3 Moves in 2025

In this forward-looking episode, Bill shares three essential strategies to enhance your business outcomes in 2025. He emphasizes the importance of authentic communication in an AI-dominated landscape while drawing from his book “12 Bold Moves.” The key strategies include: developing a clear A-to-B roadmap to guide customers from their pain points to desired outcomes, leveraging […]

Stop Leaving Money on the Table: 3 Profit Amplifiers for Sales Teams

In this episode, Bill Caskey reveals three powerful strategies to increase sales profitability without increasing workload. He unpacks the importance of monthly action planning, visual sales processes, and turning expertise into revenue-generating content. Each strategy comes with practical implementation steps that sales professionals and business leaders can start using immediately. Bill also shares a personal […]

Video, AI, and Beyond: Upgrading Your Sales Team’s Toolkit

Are your sales team’s skills stuck in the past? In this episode, Bill reveals four critical modern sales capabilities that many teams are missing out on. He breaks down why video production, digital writing/social selling, digital assets for the buyer journey, and AI implementation are no longer optional skills – they’re essential for sales success […]

The $15M Growth Blueprint Your Sales Team Needs

In this episode, Bill shares three powerful strategies that helped one of his client companies double their revenue from $15M to $30M. Bill breaks down the importance of map building (both company-wide and individual), message refinement, and conversion rate optimization. He explains why great plans should focus on inputs rather than outputs, how to craft […]

Stop the Jargon: A Conversation with Content Expert Erik Deckers

In this entertaining episode, Bill Caskey speaks with content marketing veteran Erik Deckers about the plague of corporate jargon in today’s business world. Deckers, owner of a content marketing agency and longtime humor columnist, shares his insights on why phrases like “let’s double click on that” and “value prop” are undermining clear communication in business. […]