Sales and Cigars

Walter Crosby

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!

  1. 6D AGO

    The Hidden Yes: Selling by Removing Resistance, Not Pushing Harder

    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 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.

    37 min
  2. JAN 13

    Selling Trust: Entrepreneurship, Ethics, and Disrupting a Broken System

    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 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.

    34 min
  3. 12/30/2025

    What Comedians Can Teach Us About Sales with Kevin Hubschmann

    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 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.

    37 min
  4. 12/16/2025

    Stop Buying Cheap Swag: Branded Merch that Elevates Your Brand with Eric Turney

    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 great salesperson and being a great sales manager, handling customers who only care about price, and why saying "no" is sometimes the most professional move you can make. They also get into the nuts and bolts of branded merch: why quality matters, how to help clients think beyond cheap t-shirts, and what the pandemic and shipping chaos taught Eric's team about communication, margins, and long-term customer loyalty. If you've ever ordered promo products for an event, trade show, or team—and regretted it—this one's for you. In This Episode: College vs reality – Why what you learn in college has almost nothing to do with building wealth or becoming an entrepreneur. Rich Dad, Poor Dad mindset – The books that shifted Eric's view of money, business, and long-term wealth creation. From construction to custom merch – How a layoff, a false start in physical therapy, and a new baby on the way pushed Eric into sales at The Monterey Company. Learning sales on the fly – Word tracks, repetition, and what he learned from a top car salesman buddy. The Dutch Bros lesson – Why consistently great experience beats mediocre product—and how Eric trains his reps to "bottle" that. Salesperson vs sales manager – Why being good at selling doesn't automatically make you good at leading a sales team—and what Eric had to learn the hard way. Needing to be liked – Staying up late worrying about orders, over-promising, and the shift from "pushover" to respected advisor. When to say no – Recognizing problem customers, setting boundaries, and why "if they come for price, they'll leave for price." Niche focus – How Monterey naturally gravitated to government, military, and public service clients—and what those buyers really need. Helping the real decision-maker – Working with marketing coordinators and event planners who are tasked with buying merch but don't know where to start. The Core Four sales process – Call leads quickly, text often, quote fast, and get an art proof in front of the customer ASAP. COVID, ports, and tariffs – Container costs jumping 10x, shipping delays, switching to air freight, and choosing to eat margin to preserve long-term relationships. Quality vs cheap – Why spending 20–50% more can result in a 10x better product—and how that shows up in customer perception. Brand alignment in merch – Walmart polos vs Carhartt gear, why your team's apparel reflects your brand values, and how "one thing is how you do everything." Upselling the smart way – Medals plus shirts, plus stickers; building better event experiences instead of just pushing more product. Lifetime value thinking – Why Eric would rather lose margin on a few orders than lose a great client for good. Cigars & solitude – Eric's "special occasion" approach to cigars and why a great stick pairs well with quiet, not crowds. Connect with Eric Turney LinkedIn: https://www.linkedin.com/in/eric-turney/ The Monterey Company: https://montereycompany.com/    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.

    35 min
  5. 12/02/2025

    How to Build a Sellable Business (That Could Run Without You) with B.D. Dalton

    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 business attractive to buyers (and what absolutely kills value). Walter and BD dig into BD's "goldfish test" for a truly sellable business, why some firms are worth more even with the same revenue, and how to think about your future buyer the same way you think about your ideal customer. They also walk through BD's six levers—foundation, magnetic, and amplification—and how they work whether you're 2 years or 10 years away from exiting. If your business feels like a child that never grows up and always wants money, this conversation will help you start turning it into a real asset. In This Episode: BD's journey from selling frozen burritos for Walmart/McLane to helping owners grow and exit Why every entrepreneur should think about their exit earlier than they do The "goldfish" test for a truly sellable business Recurring revenue vs. "hunt, kill, eat" revenue models What smart buyers are really looking for Why so many owners overestimate what their business is worth How BD helped a client increase valuation by 150% with simple systems The six growth levers: Foundation, Magnetic, Amplification Designing a "buyer avatar" Why brand + "your thing" matter more than most owners think Selling in 2 years vs. 7–10 years — what changes BD's annual reread: The Compound Effect Cigar story: smoking with the Swisher family and Cleveland Browns players at 25 Connect with BD Dalton LinkedIn: https://www.linkedin.com/in/b-d-dalton-ii-8a42752/ Rockfine Group: https://rockfine.co.uk/ Podcast: Grow, Sell and Retire 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.

    38 min
  6. 11/18/2025

    Building Trust in a Digital World with Butch Nicholson

    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 leaders translate those timeless relationship skills into modern selling through platforms like LinkedIn. From breaking through the fear of posting online to creating content that connects (not just promotes), Walter and Butch dig into how to be influential without trying to be an influencer. This episode is packed with wisdom for anyone learning to adapt old-school relationship-building to new-school technology. So grab a cigar, a cocktail, and settle in for a conversation about authenticity, connection, and why "know, like, and trust" still matter more than ever.   In This Episode: Why "know, like, and trust" is still the foundation of great sales How boomers and Gen X can adapt to digital buyers Why LinkedIn isn't your résumé—it's your story How to get past the fear of showing up online The difference between being influential and being an influencer Why authenticity beats polish every time How storytelling builds trust faster than any pitch The "content that connects, not promotes" mindset How Fist Bump helps CEOs and sales leaders create meaningful content   Key Takeaway: Authenticity is your advantage. The tools may change, but real connection never goes out of style.   Connect with John Kelley: Website: getfistbumps.com Email: butch@getfistbumps.com LinkedIn: https://www.linkedin.com/in/butchnicholson/    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.

    35 min
  7. 11/04/2025

    You're Not Behind on AI—You're Choosing to Stay There with John Kelley

    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 strategies, he brings a refreshing mix of heart, hustle, and tech-forward thinking. The two dig into the mindset shift required to thrive in a world increasingly influenced by artificial intelligence—and how business owners can use tools like AI to buy back their time, serve people better, and grow without burning out. Whether you're skeptical of AI or already using it in your business, this episode will challenge the way you think and give you real-world strategies to start applying today.   In This Episode: Why AI isn't coming for your job—but someone using AI might How to stop doing low-impact tasks and start focusing on what moves the needle Why the education system failed to prepare us for the AI revolution The "steam shovel" analogy every business owner needs to hear How John uses AI voice agents and automation to create speed-to-lead and drive conversions The importance of humanizing automation and staying connected to your clients How burnout forced John to re-evaluate his business, his priorities, and his mental health The power of cigars, brotherhood, and open conversations for mental wellness   Key Takeaway: If you're not using AI to eliminate low-value tasks and free up your time, you're not just falling behind—you're choosing to stay behind.   Connect with John Kelley: • Connect with John Kelley: https://johnthemarketer.com  • Try John's AI assistant: Call (346) 534-7200 • Beefy Marketing: https://beefymarketing.com  • Listen to Small Business Origins Podcast: Small Business Origins   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.

    53 min
  8. 10/21/2025

    Embracing Customer-Centric Strategies with Laura Patterson | Sales and Cigars Podcast

    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. This episode is packed with valuable tips on aligning sales and marketing efforts, serving clients effectively, and navigating the complexities of B2B sales. Tune in for a deep dive into strategic marketing and customer-centric growth, and enjoy a fun conversation with plenty of golden nuggets. Don't miss out! 00:00 The Evolution of Customer-Centric Sales 00:59 Introduction to Laura Patterson and Vision Edge Marketing 02:21 Laura's Journey to Entrepreneurship 04:52 Navigating Challenges and Building a Customer-Centric Culture 07:33 The Importance of Customer-Centric Strategies in B2B 20:26 Transparency and Data-Driven Insights 22:26 Grandfather's Fishing Tradition 24:06 Fishing as a Metaphor for Business 25:07 Understanding Your Customer 26:12 Leveraging Data for Business Insights 29:45 Importance of Clear Positioning and Messaging 31:48 Ideal Clients and How to Reach Them 36:21 Personal Stories and Reflections 39:39 Concluding Thoughts and Farewell

    42 min
5
out of 5
56 Ratings

About

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!