Episodes

Core values only matter if leaders are willing to use them. In this episode of Sales & Cigars, Walter Crosby sits down with EOS Implementer Jim Coyle to talk about culture, accountability, leadership, and the challenges founders face when trying to step out of the sales seat. Jim shares his journey from entrepreneur and bar owner to becoming one of the earliest EOS Implementers. He explains why core values should be discovered rather than created, how EOS gives organizations a common language,...

AI isn't replacing great salespeople—it's exposing average ones. In this solo episode of Sales & Cigars, Walter Crosby explains how to use AI to improve your sales process while doubling down on trust, judgment, and authentic human connection. Episode Overview Artificial intelligence is changing sales—but not in the way most people think. In this solo episode of Sales & Cigars, Walter Crosby shares why AI isn't the threat many sales professionals believe it is. Instead of replacing great sales...

In this episode of Sales & Cigars, Walter Crosby sits down with Reed Nyffeler to talk about entrepreneurship, leadership, discipline, and what it takes to build opportunity for the next generation. Reed shares how entrepreneurship runs through his family history—from his great-great-grandfather immigrating to America and farming land in Nebraska, to his own early experiences selling gum in school and building lofts for college dorm rooms. The conversation explores why entrepreneurs are essenti...

In this episode of Sales & Cigars, Walter Crosby sits down with Matt Haney, fractional COO and integrator, to talk about accountability, visionary entrepreneurs, and what really keeps businesses from scaling. Matt works with founders who have built strong companies but have reached the point where they need help turning vision into execution. The conversation digs into the tension between visionaries and operators, why accountability often breaks down, and how leaders can create clearer expecta...

In this episode of Sales & Cigars, Walter Crosby sits down with John Golden, Chief Marketing Strategy Officer at Pipeliner CRM and host of Sales Pop, for a sharp conversation about sales leadership, self-development, business acumen, and what it really takes to stay valuable in sales. John shares why SPIN Selling remains one of the most important sales books ever written and why great salespeople are still defined by their ability to ask better questions, listen deeply, and resist the urge to j...

Mike Chaput returns to Sales & Cigars to continue the conversation around leadership, culture, and why core values must go far beyond posters on the wall. In this episode, Walter Crosby and Mike dig into the real role values play inside a growing company—and what happens when leaders unintentionally create behaviors they never meant to encourage. Mike shares how nSight’s early values around humor and fun sounded positive on paper, but eventually created fear, embarrassment, and resistance to a...

Culture 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 i...

Most 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...

Bill 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 stor...

In 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 sal...

The 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 qui...

In 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...

In 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...

Most 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 ...

In 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 d...

What 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 t...

Is your “swag” secretly hurting your brand? In this episode of Sales & Cigars, Walter sits down with Eric Turney from The Monterey Company to talk about why your promo gear should do more than just check a box—it should actually say something about your brand. Eric shares his unconventional path from construction, to almost becoming a physical therapist, to “falling backward” into sales and eventually buying the company he worked for. He and Walter dig into the real differences between being a...

If you’ve started a business, you’ve probably spent more time thinking about growth than your exit. But what if building a sellable business actually makes it a better business right now? In this episode of Sales & Cigars, Walter Crosby sits down with BD Dalton—sales guy turned financial adviser, business coach, and exit-planning pro. From jacking up frozen burrito sales in the northwest to helping entrepreneurs sell their companies for 150% more than they expected, BD has seen what makes a bus...

Welcome back to Sales & Cigars, the podcast where the only smoke we blow is from cigars. In this episode, Walter sits down with Butch Nicholson, Partner at Fist Bump, to talk about something every seasoned sales professional needs to hear: how to stay relevant and authentic in today’s digital world. Butch has spent more than four decades in sales, building relationships the old-fashioned way—by getting to know people, earning their trust, and delivering value. Now, he helps Gen X and boomer le...

Welcome back to Sales & Cigars, the podcast where the only smoke we blow is from cigars. In this episode, Walter sits down with John Kelley—a firefighter, entrepreneur, podcaster, and co-founder of Beefy Marketing—for a powerful conversation about AI, automation, burnout, and what entrepreneurs need to stop doing if they want to grow. John’s journey is anything but ordinary. From running into burning buildings as a paramedic and firefighter to helping small businesses humanize their marketing ...

In this episode of Sales and Cigars, Walter interviews Laura Patterson, founder of Vision Edge Marketing, as they discuss the evolving landscape of search and the importance of being customer-centric in today's market. Laura shares insights into her entrepreneurial journey, emphasizing the significance of understanding customer value and creating effective growth strategies. She also recounts a memorable story about her grandfather that underlines the importance of knowing your target audience. ...

Welcome to Sales & Cigars—where the only smoke we blow is from cigars. This week, Walter sits down with Rocky Lalvani, the numbers-savvy entrepreneur behind Profit Comes First and the Profit Answer Man podcast. Rocky is on a mission to help business owners truly understand the business of business—from P&L and cash flow to aligning sales compensation with long-term growth. If you’ve ever had a killer sales quarter but still couldn’t figure out where the money went, this episode is for you. Roc...

Welcome to Sales & Cigars—where the only smoke we blow is from cigars. This week, Walter sits down with Michael Cole, founder of Next Level Technician, for a conversation all about helping people—the true heartbeat of sales, business, and leadership. What started as a way to connect a few underserved young people with skilled trade jobs turned into a national staffing and training company with real community impact. From hospitality to sales to entrepreneurship, Michael’s journey is rooted in ...

Welcome to Sales & Cigars, the sales podcast where the only smoke we blow is from cigars. Join host Walter Crosby in this eye-opening solo episode as he tackles common misconceptions in the sales industry. In this episode, Walter takes on two big myths: first, that promoting your top salesperson to sales manager is a smart move, and second, that hiring someone with extensive industry experience is crucial for a sales role. In this episode: Walter dives deep into why these widely held beliefs ca...