Podcast
Sales and Cigars
Hosted by Walter Crosby · EN
How do you increase sales in your organization? Host Walter Crosby sits down with cigar in hand and has growth minded conversations proven to boost sales. Crosby sets the table by identifying areas where you can excel by first acknowledging the misunderstandings. Like every great sales person he takes time to reflect, strategize and execute. Sit back, listen in, and puff that cigar because Walter Crosby will light you up!
28episodes
Episodes
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Culture Starts With the CEO
2w ago00:29:50Tap to summarizeCulture Starts With the CEO Episode Description In this episode of Sales & Cigars, Walter Crosby sits down with Mike Chaput of nSight for part one of a three-part conversation on culture, core values, and leadership. Mike shares his entrepreneurial journey—from buying an IT services company at 24, surviving the dot-com crash, navigating bankruptcy, and rebuilding from scratch—to growing nSight into a $35 million managed IT services business with more than 140 employees. The conversation digs into one of the most important responsibilities of a CEO: strategy and culture. Mike explains why culture is not a vague company concept, but the behavioral operating system that shapes every decision inside the business. This episode is for business owners who have core values on paper—but want to understand whether those values are actually helping the company grow. Episode Highlights Mike's journey from a failed first business to building nSight The hard lessons learned from bad deals, bad leases, and misplaced trust Why entrepreneurship often teaches through painful experience How CEOs shape culture whether they realize it or not Why strategy and culture are the CEO's two biggest responsibilities The "Becker rudder" analogy for leadership and organizational direction Why a business reflects the actions and beliefs of its leader How old motivations can help you grow—then eventually hold you back Why personal growth is required for business growth Key Themes & Takeaways Your business reflects your leadership. The company you have today is a result of the actions, beliefs, and behaviors that created it. Culture is not accidental. It is shaped by what leaders tolerate, reward, repeat, and reinforce. The CEO has the greatest impact on strategy and culture. Those two responsibilities cannot be fully delegated. Growth requires personal honesty. What helped you get to one stage may not help you reach the next. Core values must connect to behavior. Values only matter if the team can understand them, remember them, and live them inside the business. Entrepreneurial pain can become wisdom. Mike's early failures became the foundation for better leadership, better decisions, and a stronger company. Who Should Listen This episode is especially valuable for: Business owners with core values that feel disconnected from daily operations CEOs trying to scale without losing culture Entrepreneurs who feel like the company has hit a ceiling Leaders who want to better understand their role in shaping behavior Teams preparing to revisit or redefine their company values Links & Resources nSight https://www.nsight.com Subscribe & Follow Sales & Cigars is hosted by Walter Crosby of Helix Sales Development. The only smoke we blow is from cigars. Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you listen.
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The Sales Problem You Can't See: Storytelling, Positioning, and False Momentum
4w ago00:08:00Tap to summarizeMost CEOs think they have a sales hiring problem, a sales performance problem, or a pipeline problem. But often, the real issue is deeper—and harder to see. In this solo episode of Sales & Cigars, Walter Crosby breaks down one of the most expensive hidden problems in growing companies: a lack of shared sales story and positioning clarity. This is not usually a problem caused by bad salespeople. In fact, it often shows up inside experienced sales teams. Reps sound confident. Conversations seem productive. Deals appear to move forward. But underneath the surface, the team is defaulting to pitching instead of guiding buyers through a clear story. Walter explains why pitching is often a coping mechanism, how false momentum shows up in the pipeline, and why this issue compounds as companies grow. Episode Highlights Why many sales leaders misdiagnose messaging problems as hiring or performance problems How experienced sales teams can still create confusion in the buying process Why pitching feels productive—even when it is actually damaging deals The hidden cost of collapsing context in sales conversations How false momentum creates misleading pipeline and forecasting confidence Why this issue gets worse as companies scale and add new people The difference between a people problem and a visibility problem Why you cannot coach alignment into existence—you have to extract it How a shared sales story gives leadership more control over language, promises, and buyer expectations The practical questions leaders should ask to evaluate whether this problem exists in their business Key Takeaways Pitching is often a symptom, not the root cause. When salespeople default to pitching, it is not always because they are lazy, untrained, or ineffective. Often, they are filling a gap. Without a shared sales story to anchor them, they rely on explanation, compression, and persuasion. False momentum is dangerous. Deals can look like they are moving when they are really just drifting. The pipeline feels active, forecasts appear reasonable, and leadership assumes progress is happening—until deals suddenly stall or disappear. The real issue is often visibility. The founder usually holds the origin story. Leadership holds the strategy. Marketing holds the brand language. Sales holds the buyer friction. But no one person sees the full picture clearly, which makes alignment difficult. This problem compounds as a company grows. New reps interpret the company differently. Marketing evolves. Strategy shifts. Language starts to drift. The result is not always immediate failure—it is inconsistency that becomes more expensive over time. You cannot solve this with surface-level fixes alone. More training, more scripting, or another sales hire will not fix the core issue if the underlying story is still unclear. Companies need to extract the real story already living inside the business and make it usable for the team. A shared story improves more than messaging. When sales teams know exactly what they are carrying into buyer conversations, deals become more grounded, forecasts become more trustworthy, and leadership regains control over promises, expectations, and positioning. Who Should Listen Founders who feel like sales should be working better than it is CEOs frustrated by stalled deals and inconsistent pipeline movement Sales leaders trying to understand why experienced reps still default to pitching Companies struggling with messaging drift as they scale Anyone trying to improve sales clarity, consistency, and predictability Links & Resources Free storytelling and positioning resource mentioned in the episode Helix Sales Development Subscribe to Sales & Cigars If you want real conversations about selling, leadership, and the hidden issues that impact growth, subscribe to Sales & Cigars on Apple Podcasts, Spotify, or YouTube. The only smoke we blow is from cigars.
Transcribe →Your Story Is a Sales Advantage: A Conversation with Bill Blankschaen
Apr 700:32:12Tap to summarizeBill Blankschaen joins Sales & Cigars to explain why entrepreneurs need a clear origin story, how storytelling builds trust, and why consistent messaging gives companies a real sales advantage. Episode Overview Most companies already have a story. The problem is they are not telling it clearly, consistently, or in a way that actually connects with customers. In this episode of Sales & Cigars, Walter Crosby sits down with Bill Blankschaen, author of Your Story Advantage, to talk about why storytelling is not just a marketing tool — it is a business and sales advantage. Bill shares his own journey from leading a private school to taking a major entrepreneurial risk in order to become a writer and storyteller. That decision eventually led to building Story Builders, where he now helps entrepreneurs, authors, and businesses clarify their messaging and tell stories that stick. The conversation explores the difference between an origin story and a brand story, why sales teams need a consistent narrative, and how leaders can create messaging their teams can actually use. Episode Highlights Bill's transition from school leader to entrepreneur, writer, and storyteller The risk of leaving stable work to pursue a calling Why every entrepreneur's breakthrough begins with understanding their own story The difference between a company's origin story and its broader brand story Why inconsistent storytelling creates friction for sales and marketing teams The importance of helping the whole company "sing from the same hymnal" Bill's five-part storytelling structure: attention, tension, connection, solution, and action Why salespeople often jump to the solution too early How strong storytelling helps buyers feel understood before they ever hear the pitch Why storytelling should be customer-centered, not company-centered Key Takeaways Your story matters more than you think. Many founders and entrepreneurs downplay their own story because it feels normal to them. But your story is often the very thing that helps customers trust you, relate to you, and understand why your company exists. An origin story creates context. A strong origin story explains where the business came from, why it was started, and what problem or calling led to its creation. It gives customers and employees a deeper understanding of the mission behind the company. Your story is about you — but it is not for you. One of Bill's most important points is that while your story may start with you, it must be framed for the customer. The goal is not self-expression for its own sake. The goal is connection. Sales teams need a shared story. When every salesperson tells a slightly different version of the company story, trust erodes and the message gets diluted. Clear storytelling gives the team a shared framework they can deliver in their own voice without drifting off-message. Storytelling should start with the customer, not the product. Too many companies jump straight to features, benefits, and solutions. But buyers care first about their own goals, problems, and frustrations. The best storytelling starts there. A simple structure makes storytelling usable. Bill's five-part framework gives companies a practical way to shape their messaging: Attention — what the customer wants Tension — what is getting in the way Connection — why you understand and can help Solution — what you offer Action — what they should do next Good storytelling makes scaling easier. When the founder is the only one who can tell the company story well, growth gets stuck. A clear story helps the whole team communicate consistently across sales, marketing, and leadership. Who Should Listen Entrepreneurs trying to clarify their company messaging Founders who know their story but struggle to get it out of their head Sales leaders who want their team speaking more consistently Companies where sales and marketing are not aligned on the message Anyone who wants to turn their story into a real business advantage Links & Resources Your Story Advantage by Bill Blankschaen Story Builders Bill Blankschaen yourstoryadvantage.com Subscribe to Sales & Cigars If you want real conversations about selling, leadership, and building a message that actually connects, subscribe to Sales & Cigars on Apple Podcasts, Spotify, or YouTube. The only smoke we blow is from cigars.
Transcribe →Short-Term Pressure Is Killing Great Sales Leadership
Mar 2400:53:41Tap to summarizeIn this episode of Sales & Cigars, Walter Crosby sits down with Darren Mitchell, host of the Exceptional Sales Leader podcast, for a sharp conversation about sales leadership, short-term thinking, and what it really takes to build sustainable sales teams. Darren shares his path from engineering to telecommunications sales to sales leadership, and explains why too many organizations still confuse high-performing salespeople with high-potential leaders. The conversation digs into the pressure sales leaders face to hit short-term numbers, the damage that comes from product-first selling, and why the best leaders focus on building teams that can succeed without them. From The Infinite Game to Atomic Habits, this episode is packed with practical leadership wisdom for anyone trying to build a stronger sales culture—one rooted in service, discipline, and long-term thinking. Episode Highlights Why The Infinite Game is a must-read for sales leaders under quarterly pressure How short-termism damages customer relationships and long-term revenue Why Atomic Habits matters for sales teams and leadership development Darren's transition from engineer to salesperson to sales leader The danger of promoting top reps into leadership without proper development The powerful lesson Darren's manager gave him on his very first day as a sales leader Why the goal of great leadership is to make yourself unnecessary How sales leaders accidentally train customers to bypass their salespeople Why product training is not enough to create great sales teams The importance of understanding buyer psychology instead of pushing product Key Themes & Takeaways Great sales leaders play the long game. Organizations obsessed with quarter-to-quarter results often sacrifice trust, relationships, and sustainable growth. Leadership is not the same as top performance. Being a great salesperson does not automatically prepare someone to lead, coach, and develop others. The best leaders build teams that can thrive without them. Sales leadership is not about being the hero in every deal. It is about creating an environment where the team can perform independently. Habits drive long-term success. Small daily disciplines compound over time and create the consistency great sales teams need. Customers do not care about your product first. They care about their problems, their priorities, and what happens if those problems remain unsolved. Sales is service when done correctly. The role of the salesperson is not to push product, but to help a customer recognize a problem and evaluate a solution. Coaching and mentoring are essential. Without guidance, many new sales leaders default to control, ego, or problem-solving for their team instead of developing them. Who Should Listen This episode is especially valuable for: Sales leaders feeling trapped by short-term revenue pressure Founders and executives trying to build stronger sales leadership Organizations promoting top reps into management roles Sales teams that rely too heavily on senior leaders to close deals Anyone who wants to build a more sustainable, service-driven sales culture Links & Resources The Infinite Game by Simon Sinek Atomic Habits by James Clear Exceptional Sales Leader https://exceptionalsalesleader.com Darren Mitchell on LinkedIn Exceptional Sales Leader Podcast Subscribe & Follow Sales & Cigars is hosted by Walter Crosby of Helix Sales Development. The only smoke we blow is from cigars. Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you listen.
Transcribe →The Leadership Problem Behind Most Sales Problems
Mar 1000:39:58Tap to summarizeThe Leadership Problem Behind Most Sales Problems In this episode of Sales & Cigars, Walter Crosby sits down with Paul Fuller, Chief Revenue Officer of Membrain, for a deep conversation about sales leadership—and why most sales problems aren't really sales problems. Paul shares insights from decades of experience building and scaling sales organizations, including the early lessons he learned running a sales-as-a-service business during the 2007–2008 financial crisis. What became clear very quickly: scripts, systems, and tactics weren't the real issues. The real challenge was people—leadership, discipline, accountability, and trust. The conversation explores how trust drives decision-making, why leaders must develop people before processes, and how difficult conversations with founders, sales managers, and reps are often the key to unlocking growth. If you're leading a sales team—or trying to build one that scales—this episode is packed with practical leadership wisdom. Episode Highlights Why trust is at an all-time low in institutions—and how that impacts B2B sales The difference between acquiring information and developing true understanding Why Paul believes sales organizations should function like personal development academies Lessons learned building a sales-as-a-service company during the financial crisis The hard truth about founder-led sales teams and scaling revenue Why accountability conversations are essential—but often mishandled The leadership shift required when great sales reps become sales managers How structured planning and agreements make accountability easier Why scalable sales organizations rely on coaching and process, not just talent Key Themes & Takeaways Trust accelerates business. When trust is present, decisions happen faster and organizations move forward with confidence. Sales problems often start with leadership. Systems and scripts can only go so far—culture, discipline, and leadership behavior drive results. Information is cheap—understanding is rare. Modern sales leaders must focus on helping teams interpret and act on information, not just collect it. Founders must evolve to scale. Vision and energy can win early deals, but scalable revenue requires infrastructure and repeatable systems. Accountability must be collaborative. The best accountability conversations aren't about blame—they're about commitments and progress. Leadership is leverage. Empowering people to grow and succeed multiplies impact far beyond what any individual seller can accomplish. Who Should Listen This episode is especially valuable for: Sales leaders responsible for building scalable revenue teams Founders transitioning from founder-led sales to structured sales organizations Sales managers learning how to coach instead of just manage numbers Entrepreneurs building the infrastructure needed for growth Anyone responsible for developing people inside a sales organization Links & Resources Membrain https://membrain.com Paul Fuller Email: paul.fuller@membrain.com Subscribe & Follow Sales & Cigars is hosted by Walter Crosby of Helix Sales Development. "The only smoke we blow is from cigars." Subscribe on Apple Podcasts, Spotify, YouTube, or your favorite podcast platform.
Transcribe →Sales as Service: Why Listening Beats Tactics Every Time
Feb 2400:41:46Tap to summarizeIn this episode of Sales & Cigars, Walter Crosby sits down with Matthew Higham from Deksia for a thoughtful conversation about sales as service, culture fit, and what actually creates long-term business growth. The discussion moves well beyond tactics and into how salespeople think, listen, and show up. Matthew shares how his creative background led him into sales, why he genuinely enjoys prospecting, and how "unreasonable hospitality" applies just as much to agencies and sales teams as it does to five-star restaurants. From trusting your gut in career decisions to knowing when not to sell, this episode is a grounded reminder that great sales isn't about pressure—it's about clarity, care, and consistency. Episode Highlights Why Unreasonable Hospitality belongs on every salesperson's bookshelf Sales as a form of service—not persuasion How listening creates leverage in both sales and client relationships Why most great ideas come from volume, not perfection The difference between selling tactics and building strategy Why lead generation fails without sales readiness When saying "this isn't a fit" is the best move How culture fit shows up before the offer letter is signed Key Takeaways Sales works best when it's rooted in service Listening closely often matters more than saying the right thing Not every prospect should become a client Strategy must come before tactics Repetition builds reputation—marketing isn't flashy, it's consistent Trust your gut when evaluating culture and fit Salespeople don't need to do everything—but they do need the right support Who Should Listen This episode is for: Salespeople who care deeply about the people they sell to Agency leaders balancing strategy, service, and growth Business owners frustrated by "more leads" not solving the problem Anyone questioning whether sales can feel authentic and human Professionals evaluating culture fit in their next role About the Guest Matthew Higham is a sales leader at Deksia, a full-journey marketing agency known for its strategy-first approach. With a background in the creative world, Matthew brings a people-first perspective to sales—one focused on listening, alignment, and long-term outcomes over short-term wins. About Deksia Deksia is a full-journey marketing agency that helps organizations grow by aligning strategy, brand, and execution. Rather than leading with individual tactics, Deksia starts with business goals and builds integrated marketing systems designed for sustainable growth. Links & Resources Matthew Higham – Email: matthew@deksia.com Deksia Website Unreasonable Hospitality by Will Guidara Subscribe & Follow Sales & Cigars is hosted by Walter Crosby of Helix Sales Development. The only smoke we blow is from cigars. Subscribe wherever you listen to podcasts and join the conversation.
Transcribe →The Approval Trap: Why Being Liked Can Kill the Deal
Feb 1000:43:25Tap to summarizeIn this episode of Sales & Cigars, Walter Crosby sits down with Nick Massaro of Membrane for a candid, no-BS conversation about what actually holds good salespeople back. From early sales foundations and structured training to the mindset traps that quietly derail deals, this episode digs into the space between opening and closing—the part most reps avoid and where deals are truly won or lost. Nick shares his journey into sales, the evolution of his mindset, and the hard-earned realization that being "the most liked rep" is often a sign something went wrong. Together, they unpack the dangers of approval-seeking, why discomfort is part of great selling, and how modern buyers require a different kind of leadership from sales professionals. This is a grounded, honest conversation for salespeople who want to stop getting compliments instead of contracts. Episode Highlights Why "You were the best rep" is often a kiss of death The difference between opening deals and advancing them How early structure shaped Nick's sales foundation The mindset shift required to lead buyers without controlling them Why avoiding money conversations quietly kills deals Selling outcomes vs. selling features—especially in complex software Letting go of approval to ask better questions What great sales and good parenting surprisingly have in common Key Takeaways Being liked doesn't equal being effective The middle of the deal—not the open or close—is where salespeople grow Approval-seeking prevents tough (necessary) conversations Buyers are in control—but salespeople must still lead Discovery isn't about sounding smart; it's about creating clarity Authenticity beats polish every time Process creates freedom, not rigidity Who Should Listen This episode is for: Salespeople who hear "we loved you" more than "we're buying" Reps who love prospecting but struggle with deal momentum Sales leaders coaching mindset, not just activity Anyone selling complex or non-commodity solutions Business owners trying to understand what their sales team is really up against About the Guest Nick Massaro is a sales professional at Membrane with a background spanning insurance, SaaS, and sales-as-a-service environments. Known for his authenticity and curiosity, Nick brings a thoughtful perspective on modern selling—one rooted in structure, accountability, and continuous improvement. Connect with Nick Nick Massaro on LinkedIn Membrane Connect with Walter Crosby and Sales & Cigars: Website: Helix Sales Development LinkedIn: Walter Crosby Instagram: @wcrosby248 Facebook: Helix Sales Development Share Your Thoughts: We'd love to hear your feedback and experiences! Drop us a line and join the conversation on social media using #SalesAndCigars. Never Miss an Episode! Join the Sales & Cigars community by subscribing to our podcast and YouTube channel: Subscribe to the Podcast: Apple Podcasts: Subscribe on Apple Podcasts Spotify: Follow on Spotify ...and wherever you listen to podcasts! Subscribe to Us on YouTube: Stay updated with our latest video content by subscribing to our YouTube channel. Hit the bell icon for notifications on new uploads! YouTube: Sales & Cigars Channel Stay in the loop: By subscribing, you'll get instant access to new episodes, insightful conversations, and bonus content designed to elevate your sales skills and more. Keep savoring those cigars and stay sharp in sales! Until next time, keep listening to Sales & Cigars—the podcast where the only smoke we blow is from cigars.
Transcribe →The Hidden Yes: Selling by Removing Resistance, Not Pushing Harder
Jan 2700:37:24Tap to summarizeMost sales advice focuses on one thing: motivation. More features. More urgency. More discounts. In this episode of Sales & Cigars, Walter sits down with consumer psychology expert Matt Sucha to challenge that assumption—and reveal why buyers often don't need more reasons to say yes… they need fewer reasons to say no. Matt breaks down the psychology behind stalled deals, hesitation, and "I'll think about it," drawing from behavioral economics, real-world case studies, and his book The Hidden Yes. If you've ever felt like your offer made sense but still didn't close, this conversation explains why. In This Episode: Why logic doesn't close deals—feelings do The biggest mistake salespeople make: over-focusing on motivation How uncertainty, doubt, and fear silently kill conversions Why free offers often feel less valuable to buyers The difference between objective value and perceived value How context can change willingness to pay—without changing price A real-world insurance case study that led to a 167% conversion lift Why better sales starts with asking: "Why wouldn't they buy?" Key Takeaways: Buyers don't stall because they're unmotivated—they stall because something feels risky. Removing psychological friction is often more powerful than adding incentives. Context (how and when you present information) shapes value more than price itself. Great sales conversations are designed—not improvised. Free Gift for Our Listeners! Click here for a free gift from Matt! Connect with Matt: https://mindworx.net/ https://thehiddenyes.com/ LinkedIn: https://www.linkedin.com/in/matt-sucha/ Connect with Walter Crosby and Sales & Cigars: Website: Helix Sales Development LinkedIn: Walter Crosby Instagram: @wcrosby248 Facebook: Helix Sales Development Share Your Thoughts: We'd love to hear your feedback and experiences! Drop us a line and join the conversation on social media using #SalesAndCigars. Never Miss an Episode! Join the Sales & Cigars community by subscribing to our podcast and YouTube channel: Subscribe to the Podcast: Apple Podcasts: Subscribe on Apple Podcasts Spotify: Follow on Spotify ...and wherever you listen to podcasts! Subscribe to Us on YouTube: Stay updated with our latest video content by subscribing to our YouTube channel. Hit the bell icon for notifications on new uploads! YouTube: Sales & Cigars Channel Stay in the loop: By subscribing, you'll get instant access to new episodes, insightful conversations, and bonus content designed to elevate your sales skills and more. Keep savoring those cigars and stay sharp in sales! Until next time, keep listening to Sales & Cigars—the podcast where the only smoke we blow is from cigars.
Transcribe →Selling Trust: Entrepreneurship, Ethics, and Disrupting a Broken System
Jan 1300:34:13Tap to summarizeIn this episode of Sales & Cigars, Walter sits down with Alan Ward, CEO of Securely.io, for a thoughtful conversation that spans entrepreneurship, sales, leadership, and the realities of disrupting long-entrenched systems. Alan shares how his worldview shapes the way he leads and sells, why transparency is missing in traditional payment systems, and what it takes to introduce truly revolutionary ideas into the market. From cutting a house in half at 19 years old to building a fintech platform designed to serve businesses—not extract from them—this episode is about values, conviction, and selling change the right way. In This Episode: Why Who Not How shaped Alan's approach to leadership and business The Golden Rule as a foundation for sales, culture, and decision-making How worldview influences leadership and organizational behavior Alan's entrepreneurial origin story and early risk-taking Why businesses don't truly understand their payment costs What "open banking" means—and why it's a game changer Evolutionary vs. revolutionary change in technology and sales Why education—not pitching—is required to sell disruptive ideas Selling vision to customers, teams, investors, and boards The role of trust, transparency, and alignment in long-term success Celebratory cigars and the moments that make business memorable Key Takeaways: Sales is often about helping people see what they couldn't see before Transparency builds trust—hidden systems create resistance Entrepreneurs are always selling, even when they don't realize it Revolutionary ideas feel risky until they become obvious Values-driven leadership scales better than tactics alone Connect with Alan: LinkedIn: linkedin.com/in/alan-ward-63938020a Website: Securely.io Connect with Walter Crosby and Sales & Cigars: Website: Helix Sales Development LinkedIn: Walter Crosby Instagram: @wcrosby248 Facebook: Helix Sales Development Share Your Thoughts: We'd love to hear your feedback and experiences! Drop us a line and join the conversation on social media using #SalesAndCigars. Never Miss an Episode! Join the Sales & Cigars community by subscribing to our podcast and YouTube channel: Subscribe to the Podcast: Apple Podcasts: Subscribe on Apple Podcasts Spotify: Follow on Spotify ...and wherever you listen to podcasts! Subscribe to Us on YouTube: Stay updated with our latest video content by subscribing to our YouTube channel. Hit the bell icon for notifications on new uploads! YouTube: Sales & Cigars Channel Stay in the loop: By subscribing, you'll get instant access to new episodes, insightful conversations, and bonus content designed to elevate your sales skills and more. Keep savoring those cigars and stay sharp in sales! Until next time, keep listening to Sales & Cigars—the podcast where the only smoke we blow is from cigars.
Transcribe →What Comedians Can Teach Us About Sales with Kevin Hubschmann
Dec 3000:36:40Tap to summarizeWhat do improv comedy, standup, and high-performing salespeople have in common? More than you think. In this episode of Sales & Cigars, Walter Crosby sits down with Kevin Hubschmann to explore how comedy skills like active listening, adaptability, brevity, and comfort with failure directly translate to better sales conversations. Kevin shares how doing improv in a cramped New York apartment sharpened his instincts on sales calls, why scripts often fail in real-world selling, and how learning to bomb—on stage and in sales—became a competitive advantage. This is a practical, mindset-shifting conversation for sellers who want to think differently about discovery, messaging, and growth. In This Episode: Falling into sales while trying to survive in New York City How improv immediately improved Kevin's sales calls Why listening is the most underrated sales skill The danger of rigid scripts when buyers "take a left turn" What standup comedy teaches about clarity and concise messaging Why losing deals is essential to becoming a better salesperson Using low-stakes reps to test ideas and improve performance How comedy training is now being used to develop sales teams Key Takeaways: Great sales conversations are collaborative, not scripted Listening beats pitching every time Clear, concise messaging travels further inside an organization Failure is data—not a verdict Reps, reflection, and refinement matter more than talent Connect with Kevin: LinkedIn: https://www.linkedin.com/in/kevin-hubschmannn/ Instagram: https://www.instagram.com/laughdotkevin/ Laugh.Events: https://www.laugh.events/ Connect with Walter Crosby and Sales & Cigars: Website: Helix Sales Development LinkedIn: Walter Crosby Instagram: @wcrosby248 Facebook: Helix Sales Development Share Your Thoughts: We'd love to hear your feedback and experiences! Drop us a line and join the conversation on social media using #SalesAndCigars. Never Miss an Episode! Join the Sales & Cigars community by subscribing to our podcast and YouTube channel: Subscribe to the Podcast: Apple Podcasts: Subscribe on Apple Podcasts Spotify: Follow on Spotify ...and wherever you listen to podcasts! Subscribe to Us on YouTube: Stay updated with our latest video content by subscribing to our YouTube channel. Hit the bell icon for notifications on new uploads! YouTube: Sales & Cigars Channel Stay in the loop: By subscribing, you'll get instant access to new episodes, insightful conversations, and bonus content designed to elevate your sales skills and more. Keep savoring those cigars and stay sharp in sales! Until next time, keep listening to Sales & Cigars—the podcast where the only smoke we blow is from cigars.
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