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WINNING AT SELLING

Bill Hellkamp and Scott "Professor Plum"

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Welcome to the Winning at Selling Podcast. Your hosts Bill Hellkamp and Scott “Professor Plum.” This podcast is dedicated to the overall success in the sales channel. From the CEO to the front line salespeople, every role must be aligned, trained and committed, every day to achieve the desired outcome. This is not done without a commitment to ongoing career development in learning market-relevant techniques, overcoming conceptual barriers, applying proactive and productive behaviors and proj ...
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Welcome to The Bill Caskey Podcast, the show for company leaders, sales managers, and salespeople who are looking to take their sales game to the next level. Join your host Bill Caskey, renowned sales coach and strategist, as he shares modern sales strategies and leadership tips that will help you grow your sales team and increase revenue for your business. Each week, Bill brings a variety of guest experts and shares real coaching scenarios from his work with sales teams, providing valuable ...
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Are you a business owner or startup founder struggling to navigate the challenges of growth? Join seasoned entrepreneurs Matt and Chris Reynolds on the Build Your Business Podcast, where they share decades of experience to help you overcome obstacles and achieve lasting success. We’ll simplify the startup process, provide actionable strategies for growth, and offer invaluable insights to help you. What you'll gain: Overcome your fears: Break through the anxiety and uncertainty that often hol ...
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Hope isn't a strategy on the battlefield or in the boardroom, yet so many salespeople hope they'll make the next sale. In Bulletproof Selling, we're bringing the best minds and selling systems together each week so you can create more impact and more income in your sales! For more free sales systems, make sure you visit www.bulletproofselling.us or follow us at https://www.linkedin.com/in/shawnrhodes/
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Welcome to High Impact Sales Podcast for leaders ready to transform their sales experience and scale their revenue with help, impact, and integrity. It’s time for you to discover YOUR unique identity and how to connect with your audience. Listen to the latest episode with your hosts, Natalie Jill and Sinclair Kennally.
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We all carry voices from our past into our present—from our parents, the pastor from Sunday, the last prospect who brushed us off, the customer who complained about delivery, even our boss reminding us about our quota. They echo in the back of our minds and distract us from the person sitting right in front of us, now. The problem is, those voices …
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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 les…
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In our last episode we closed with a quote from Bob Nardelli, the former CEO of Home Depot: “I absolutely believe that people, unless coached, never reach their maximum capabilities.” If true, we should be looking for coaching opportunities every day with the hope of finding someone who will work with on a long-term basis. But, if we don’t listen a…
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Sales isn’t just about numbers—it’s about sparking curiosity, creating connections, and leaving people amazed. Now, imagine a speaker who blends the precision of a teacher, the creativity of a magician, and the insight of a strategist. This isn’t “just talk”—it’s an experience that makes your sales message unforgettable, turning ideas into impact a…
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Sales isn’t about tricks or scripts—it’s about understanding people. When you sell with empathy, clarity, and respect, you don’t just win deals—you build trust, loyalty, and long-term relationships. The question is, “How do you accomplish that?” Put on your EMPATHY hat as Scott and I discover What Buyers Really Want and other ridiculous ramblings o…
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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…
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This is a quick update from Matt on the Build Your Business Podcast. It’s been a crazy but good year with lots happening—family moves, business growth, and plenty of irons in the fire. Because of that, we’re taking a short break until the fall. 👉 Here’s what you need to know: We’ll be back this fall with brand new episodes. Please stay subscribed s…
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Many salespeople think they’re in a test every time they meet a prospect—measured on how much they know and how perfectly they can present. But selling isn’t about passing a test. It’s about uncovering what matters most to the prospect. In this episode, we’ll look at how shifting from “proving yourself” to “understanding them” can change the conver…
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Selling without the sleaze isn’t just possible—it’s the fastest way to build trust, win clients, and grow your business. In this episode of the Build Your Business Podcast, Matt and Chris Reynolds break down a founder-tested approach to sales that replaces pushy tactics with authentic problem-solving. You’ll learn how to lead with trust, diagnose r…
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How can a centuries-old art form help your organization engage employees, build teamwork, and create a culture of innovation? For decades, the techniques of improvisation, or “improv,” have helped organizations do just that. Improv is more than just funny; it is fun and valuable training. If you lead teams, interact with clients or customers, or fa…
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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 in…
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We don’t execute on what we don’t believe. Whether it’s a sales process, a life change, or a new habit, our actions—or lack of them—are rooted in what we truly believe about ourselves and what’s possible. In this episode, we’ll explore how belief shapes behavior and how shifting what you believe - can unlock the consistent execution you need for re…
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Why core values matter for founders isn’t just a philosophical question—it’s a strategic necessity. In this episode of the Build Your Business Podcast, Matt and Chris Reynolds break down how your personal values shape your business, influence hiring, drive decision-making, and define company culture. You'll learn how to discover your real—not aspir…
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In this episode of the Build Your Business Podcast, Matt and Chris Reynolds unpack what may be the most important skill for any entrepreneur: deep work for founders. They reveal how to build rituals that trigger flow, how to design your day around peak focus hours, and why eliminating distractions is the first step toward real freedom in your busin…
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In sales, there’s a common pattern that many professionals follow with the best intentions. They ask questions. They probe. They dig into the mechanics of a prospect’s situation—what systems are they using? How much are they spending? What’s not working? Next they tie the pertinent features into benefits for the prospect. But seldom do they get int…
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How do you lead your business when everything falls apart? In this episode of Build Your Business, Matt and Chris Reynolds share exactly how to handle business crisis—from late-night tech meltdowns and legal threats to complete operational shutdowns. They dive into real-world examples of how founders can stay calm, lead with confidence, and rally t…
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Are you living with purpose—or just going through the motions? In today’s episode, we explore how purpose shapes your work, relationships, and identity. Discover how alignment brings clarity and fulfillment, and learn practical steps to overcome fear, find direction, and start living the life you’re meant to lead. If you are open to new ideas and d…
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If your business feels like it’s running you—rather than the other way around—this episode is your roadmap out of chaos. Matt and Chris Reynolds break down why systems and SOPs (standard operating procedures) are the foundation of any successful, scalable business. You’ll learn how to start with simple wins, avoid common delegation mistakes, and bu…
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Responding to a Request for Proposal (RFP) can be a powerful way to win new business—but only if it’s the right opportunity. RFPs often demand considerable time, resources, and cross-functional coordination, so blindly responding to every one can lead to wasted effort, low win rates, and team burnout. Look up your RFP win rates as Scott and I quest…
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Discover how to apply Profit First for Founders and finally gain control over your business finances. In this episode of the Build Your Business Podcast, Matt and Chris Reynolds walk you through the exact strategies they’ve used to move from cash burn to consistent profit—including financial dashboards, lean budgeting, and tactical cost-cutting. Wh…
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Have you ever been torn between jumping into action or holding back to wait for the perfect moment? Today we explore the tension between taking immediate action and practicing delayed gratification. Can you really do both—and should you? You don’t have to wait another moment as Bill, and I pause to discuss Start or Wait… What Should I Do? and other…
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Struggling to get more clients? This episode of the Build Your Business Podcast shows you how using content to build trust and win clients is the most scalable, low-cost marketing strategy for entrepreneurs. Matt and Chris Reynolds break down why your founder story matters more than your brand, and how authenticity, vulnerability, and consistency d…
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Scott and I have been pouring our knowledge and experience into this podcast for over 5 years with the hope that sales professionals would be able to use this information to sell more and win at selling. And that sales leaders would be able to augment their own training with the ideas presented in our podcast. While we’ve spoken to many of our list…
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Are you ignoring churn in your business? You might be losing more than you realize. In this episode of the Build Your Business podcast, Matt and Chris Reynolds reveal how churn is the silent killer of growth—especially in service-based and fitness businesses. They share actionable strategies to improve client retention, reduce drop-off, and turn sa…
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As a salesperson - have you ever said behind your sales manager's back - I could do a much better job than they can. Be careful what you wish for. It may look more glamorous than it really is. There are some pros and cons to being a salesperson versus a sales manager than you think. Listen up as we try to encourage and discourage a shift in your re…
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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…
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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 br…
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Customer focus isn’t just a buzzword—it’s the foundation of long-term business growth. In this episode of the Build Your Business podcast, Matt and Chris Reynolds share real-life stories—from a sudden family relocation to a dangerous carbon monoxide scare—that highlight why putting people first pays off in the business world. Learn how to build tru…
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One of the keys to maintaining value is to be able to differentiate your product or service from the competition. While this can be difficult to do, it is necessary to keep from becoming commoditized. Be ready for some critical thinking as Scott and I investigate The Power of Product Differentiation and other flippant philosophies on Episode 673 of…
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Is online coaching actually better than in-person coaching? In this episode of the Barbell Logic Coaching Success Series, Matt Reynolds shares why online coaching offers unmatched freedom, better financial efficiency, and stronger client results than traditional in-person sessions. Drawing on decades of experience both in gyms and running TurnKey C…
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Are you leading with purpose — or just going through the motions? What’s the difference between intentional leadership and reactive management. How can you create a collaborative culture by design and not by default. Whose fault is that? Stay tuned for an engaging conversation about “leading the way” to your personal and professional goals as Bill …
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What makes people trust you in business—and what breaks that trust without you even realizing it? In this episode of Build Your Business, Matt and Chris Reynolds sit down with Andrew Jackson, COO of TurnKey Coach, to unpack The Trust Equation, a framework rooted in real leadership, lean systems, and years of experience. Whether you're leading a tea…
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Has it ever happened to you that you go into an appointment expecting to meet with a single person, but when you get to the conference room there are already 3 other people seated around the table? Although this can cause your stomach to turn over, it isn’t really a bad thing. However, it can go south quickly if you don’t adapt your strategy. Hey k…
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Firing someone is one of the hardest parts of leadership—but avoiding it can cost your business even more. In this episode of Build Your Business, Matt and Chris Reynolds break down how to fire someone the right way: with clarity, compassion, and professionalism. Whether it's your first time or you're trying to improve your process, you'll learn ho…
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How would increasing your word-of-mouth reputation affect your sales pipeline in the short and long term? A referral from your network is one of the most credible and cost-effective forms of marketing. For salespeople, activating and amplifying word-of-mouth can shorten your sales cycles and build trust faster than any website or email. But is this…
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📄 Are you stuck doing everything yourself because no one else can do it “right”? In this episode of Build Your Business, Matt and Chris Reynolds break down why perfectionists struggle with delegation—and how to fix it. Learn how to build trust, communicate expectations clearly, and use systems that protect your standards without burning you out. Di…
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In this episode, Bill shares a live coaching session with one of his clients - a leadership consultant who landed his first cold outreach call after just one week of working a LinkedIn strategy. Bill breaks down the exact 5-step framework he uses to help consultants and service providers turn initial prospect calls into profitable engagements. This…
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Often when we are trying to make a sale we get totally focused on the value we can bring to the prospect and their business. Seldom do we consider the ramifications our new product or service will have for the people and their work flow. That’s right; our new “whatever” is disrupting the business even as it is providing new value. In short we are t…
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How do you manage conversations, remember your priorities, and accurately forecast sales—all while juggling a packed calendar? You guessed it: your CRM. But most salespeople treat their CRM like a dumping ground instead of the behavior-driving tool it should be. So sharpen your stylus and clear your memory cache as Bill and I dive into Using Your C…
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As a business owner, it's easy to push off the things that really matter—your family, your health, your strategic thinking—because they're not screaming for attention. But eventually, they will become urgent. In this episode, Matt Reynolds shares how he cleared his schedule, tackled long-neglected priorities, and rediscovered what it means to lead …
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Bill Caskey tackles a topic close to home - how sales professionals over 50 can maintain and even increase their relevance in a rapidly evolving marketplace. Drawing from personal experience and client success stories, Bill shares five critical strategies that seasoned professionals must adopt to thrive. Whether you're approaching 50, already there…
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In this episode, Matt Reynolds shares why learning to take some time off might be the smartest thing you do as a business owner. He unpacks how intentional rest can increase creativity, sharpen your strategic thinking, and actually improve your output as a leader. Whether it’s a simple weekend away or a longer retreat, Matt offers practical steps f…
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Does your sales process advocate emailing your proposal to the prospect and then calling in a few days to see what they think? If so, YOU ARE OUT OF YOUR MIND! Whoops, got a little strident there! What I meant to say was, we think there is a better way. So, move your had away from that SEND button as Scott and I discuss the Advantages of Interactiv…
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