Bill answers three critical questions from listeners: What's the greatest sales lesson learned the hard way? What's the biggest challenge in the last five years? And if he could eliminate one sales practice forever, what would it be?

Key Takeaways:

• Why pushing harder in follow-up creates resistance and kills deals
• How the harder you press, the less likely you are to close
• Why marketing has become essential for every sales professional (not just the marketing department)
• The power of platform building: podcast, YouTube, email series, or video content
• How 10 years of content consumption can turn into a 70% close rate
• The needy email problem and what to do instead
• The 12-question content strategy that transforms cold prospects into warm leads

Join Bill's December 5th Personal Business Planning Workshop (12-2pm ET) for just $97. Get the replay, workbook, and accountability session. Save your seat now: https://resources.billcaskey.com/2026-business-planning-workshop

Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at billcaskey.com/businessplanning.

Planning season is here, but most salespeople confuse forecasting with actual planning. In this episode, Bill shares three critical building blocks from his upcoming Personal Business Planning Workshop that will help you create a comprehensive plan for 2026—not just revenue targets, but a real roadmap for growth.

Bill walks you through practical examples, including how to create lead magnets that attract qualified prospects and position you as the expert. Whether you join his December 5th workshop or start implementing these three blocks today, you'll be ahead of the game in 2026.

Join Bill's Personal Business Planning Workshop: December 5th, 12-2 PM ET Get all nine building blocks, a 12-page workbook, and a one-page planning overview for just $97. Get your ticket now!

Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at billcaskey.com/businessplanning.

Bill opens up his coaching playbook to share three real goals from new clients—and what he's going to do about them. From comfort zones to expertise, from undervaluing yourself to finding confidence, these objectives represent what 90% of B2B sales teams struggle with. 

Listen as Bill breaks down the first goal: how to move from being the expert to being the transformational partner your clients actually need.

12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.

Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at [email protected].

Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.

Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at billcaskey.com/businessplanning.

What happens when experienced B2B sales professionals—many with engineering backgrounds—spend six months mastering consultative selling techniques? In this episode, I share the five most impactful lessons from a recent training program with high-end hydraulic and timing solutions salespeople.

You'll discover why being mindful of the "okay vs. not okay" dynamic transforms customer interactions, how upfront agreements and detachment create better outcomes, and the critical importance of operating on two levels simultaneously—being in the conversation while also observing it.

Whether you're selling complex solutions or leading a sales team, these field-tested insights will help you connect more authentically with prospects and close more deals.

12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.

Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at [email protected].

Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.

Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at billcaskey.com/businessplanning.

In this episode, Bill Caskey sits down with marketing expert and recovering musician Jason Leister to explore a topic that sits beneath the surface of most business conversations: the power of being yourself.

Jason shares his journey from being a "straight-A sheep" who followed all the rules to discovering that the only person he hadn't tried being in business was actually himself. The conversation digs into why we're taught to focus on what we want to do rather than who we want to be, and how that misdirection costs us years of detours, therapy, and unfulfilled projects.

If you've ever felt like you're operating at a fraction of your potential, or you're tired of being everyone except yourself, this conversation offers a refreshing perspective on building a business—and a life—that actually fits who you are.

Subscribe to Jason's daily newsletter at JasonLeister.co for continued insights on becoming more fully yourself in business.

Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at [email protected].

Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.

Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at billcaskey.com/businessplanning.

In this heartfelt tribute episode, we pause to reflect on the life and legacy of Charlie Kirk, the founder of Turning Point USA who was tragically taken from us far too soon. While this isn't a political analysis, it's a personal reflection on what we can learn from Charlie's approach to life and leadership.

This episode explores the leadership lessons we can all take from Charlie's life: his courage to engage in difficult spaces, his ability to stay on message, his mastery of media platforms, and most importantly, his dedication to serving as a voice of hope for young people who felt forgotten by society.

Whether you agreed with his politics or not, there's no denying Charlie Kirk's massive impact on American youth and his role as a devoted father and husband. Join us as we honor his memory and reflect on how we can better support the young people in our own lives during these challenging times.

This is a one-time tribute episode from someone who admired Charlie's communication skills and dedication to youth empowerment, regardless of political affiliation.

One of the biggest problems B2B sales professionals face? They're out of position from the moment they walk into a meeting. In this episode, Bill shares a tennis lesson that completely changed how he thinks about sales positioning, and reveals the three essential elements every salesperson needs to transform from a desperate "seller" into a trusted guide.

You'll discover why most salespeople are closing only 15-20% of their deals (hint: prospects don't know what happens after they say "yes"), the simple roadmap strategy that doubled one company's close rate in 120 days, and how to position yourself as the obvious choice before you even have your first conversation.

If you're tired of feeling like you're chasing prospects and want to start having them chase you, this episode will show you exactly how to make that shift.

12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.

Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at [email protected].

Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.

Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at billcaskey.com/businessplanning.

Ever wonder why prospects aren't being completely honest with you? In this episode, Bill reveals the uncomfortable truth: buyers think it's okay to lie to salespeople. 

Drawing from 30 years in the business and insights from sales expert Terry Slattery, Bill explains why prospects withhold critical information and shares four proven strategies to inspire trustworthiness from the very first interaction.

When you master these techniques, prospects stop looking for reasons NOT to work with you and start looking for reasons TO work with you.

12 Bold Moves: Want to break free and soar to new heights? "12 Bold Moves" is your gateway to a fearless reinvention of self and unlocking unprecedented sales success.  Get your copy now at http://12boldmoves.com.

Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at [email protected].

Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.

Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at billcaskey.com/businessplanning.

Ready to transform your sales game? In this episode, Bill Caskey sits down with Jonathan Mast, founder of White Beard Strategies, to reveal how AI can revolutionize your sales process—without replacing you.

If you're tired of endless cold calls, struggling to keep up with CRM updates, or feeling overwhelmed by your daily tasks, this conversation is a game-changer. Jonathan shares his journey from skeptical observer to AI advocate, explaining how he built a seven-figure business in under two years using AI as his secret weapon.

Jonathan proves that AI isn't about working harder—it's about amplifying your existing skills to work smarter. Whether you want to work fewer hours for the same money or work the same hours to make 3-4x more, AI makes both possible.

No tech background required—just a willingness to get in the game.

This is part 1 of a special AI transformation series on the Bill Caskey Podcast.

Stop going it alone—join our 2X Introductory Session and discover if you're one of the 10 people we'll accept this month: https://resources.billcaskey.com/2x-workshop

12 Bold Moves: Want to break free and soar to new heights? "12 Bold Moves" is your gateway to a fearless reinvention of self and unlocking unprecedented sales success.  Get your copy now at http://12boldmoves.com.

Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at [email protected].

Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.

Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at billcaskey.com/businessplanning.

Why doesn't Bill get invited to traditional sales conferences anymore? In this no-holds-barred episode, he shares five controversial takes that challenge everything the sales industry has been teaching for decades. From why persuasion is overrated to why cold calling is a symptom of failed strategy, Bill dismantles conventional sales wisdom with brutal honesty.

Warning: If you're deeply invested in traditional sales methods, this episode might make you uncomfortable. But if you're ready to challenge the status quo and build a modern revenue engine that actually works, this is your wake-up call.

2X Strategies Download: If you want to download all ten "2X Strategies", go here to get them now: https://billcaskey.com/2xstrategies

12 Bold Moves: Want to break free and soar to new heights? "12 Bold Moves" is your gateway to a fearless reinvention of self and unlocking unprecedented sales success.  Get your copy now at http://12boldmoves.com.

Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at [email protected].

Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.

Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at billcaskey.com/businessplanning.