Sales and Cigars

Walter Crosby
  • 5.0 (57)
  • Entrepreneurship
  • Weekly

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. 2d ago

    Ask the Question, Then Shut Up: How Luke Hostetter Built a 5-State Territory from $750K to $4.8M ARR | Ep. 255

    Cigar of the Episode: - Studio Smoke: Montecristo Classic Churchill (paired with coffee & water) - Also in Luke's Humidor: Montecristo Platinum, Montecristo No. 2, CAO MX2 (Double Maduro), CAO Vision, La Aurora, Oliva Serie G & Serie O, and Nub   Episode Summary: What do selling strawberries for Mennonite farmers in Lancaster County, refereeing 150 screaming used-car dealer disputes a week at the world's largest auto auction at age 20, and spotting cabinet shops by the stain rags outside their bay doors have in common? For enterprise software sales executive Luke Hostetter, every single stop was a masterclass in human nature, creative negotiation, and consultative selling.   In Episode 255 of Sales & Cigars, Walter Crosby lights up a Montecristo Classic Churchill with Luke Hostetter (Enterprise West Account Executive at NiCE) to trace Luke's path from early blue-collar hustle to scaling a five-state Western territory from $750K to $4.8M ARR—and now closing multi-million-dollar enterprise AI and customer experience deals on 18-to-20-month cycles. Along the way, Walter and Luke break down the five traits every elite consultative salesperson needs (curiosity, inquisitiveness, skepticism, empathy, and shutting up after the question mark), why 60% of reps still pitch instead of diagnose, and how a teenage Cuban Montecristo No. 2 set off a hotel fire alarm in Belgium at 2:33 in the morning.   In This Episode, We Discuss: - [00:00] Lighting up a Montecristo Classic Churchill: Luke's first cigar at 14 (Rocky Patel Edge Corojo) and Sunday porch rituals with cream soda at 16 - [04:50] Growing up in Lancaster County, Pennsylvania: Selling candy door-to-door at age 8 and working a farmer's market stand for Mennonite strawberry farmers - [07:45] How a clean personal car and a conversation with a regular strawberry customer (a lawyer with a Porsche Cayenne Turbo and BMW M5) launched Luke's college mobile auto-detailing business - [11:45] Skin in the game: Why Luke's dad matched every dollar he paid toward Millersville University tuition—and getting married at 21 while building a career - [13:15] Trial by fire at age 20: Running arbitration at Manheim Pennsylvania (the world's largest wholesale auto auction—600,000 cars/year) with 3 days of training from "Captain Russ" - [18:10] "Divorce lawyer for used car dealers": Handling 150 angry buyer-seller disputes a week and learning creative negotiation to keep deals together - [25:20] Moving to Colorado at 24: How Luke's manager rode with him for 3 days with a laptop GPS, dropped him at the Denver airport, and said, "All right, buddy, build it" - [31:40] Scaling a 5-state cabinet-component territory (CO, NE, KS, NM, UT) from $750K to $4.8M ARR over 8 years—driving 50,000 miles a year and spotting prospects by dust collectors and stain rags - [39:15] Transitioning from industrial building products to healthcare staffing, telecom, and multi-million-dollar enterprise AI/CX software cycles - [45:10] Inside Luke's humidor: Montecristo Platinum, CAO MX2, Oliva Serie G & O, golf course cigar etiquette, and why Gurkhas are "golf course giveaway cigars" - [56:35] The 2:33 AM Belgian fire alarm story: Smoking a Cuban Montecristo No. 2 out a hotel window at age 17 on a church mission trip - [01:02:45] Walter's evening cigar & 3-item brain-dump ritual to quiet a racing mind before bed - [01:08:50] How reading SPIN Selling and Never Split the Difference—plus pre-call planning and post-call car debriefs—transformed Luke into a 3-time Top Producer - [01:15:30] Walter's kitchen remodel test: Why he hired the designer who took her shoes off and asked 3 questions while 60% of salespeople just pitch - [01:19:40] The 5 Pillars of Consultative Selling: Curiosity, Inquisitiveness, Skepticism (pushing back on a stubborn New Mexico custom cabinet maker), Empathy, and Shutting Up After the Question Mark - [01:26:05] What separates great sales leaders from transactional managers: building genuine rapport, coaching in the field, and getting past the fear of uncomfortable growth   Key Takeaways for Sales Leaders & Reps: 1. Build Skin in the Game Early: Whether it's negotiating 150 auto-auction disputes a week at age 20 or driving 50,000 miles a year across five states with a laptop GPS, early high-volume reps build callouses and conflict-resolution instincts that no classroom can teach. 2. Diagnose Before You Prescribe: Just like the kitchen designer who won Walter's business by asking three simple questions ("What do you like about your current kitchen? What don't you like? How long will you live here?"), elite sellers resist the urge to pitch and focus on uncovering real motivation. 3. Pair Curiosity with Healthy Skepticism: Buyers don't always tell the full truth—or even understand their own bottleneck. When a New Mexico cabinet craftsman insisted nobody could match his quality, Luke pushed back with healthy skepticism and showed how outsourcing doors at millimeter tolerances could take him from 1 kitchen a month to 5 and pay for his son's college. 4. Debrief Every Call at the Steering Wheel: Before putting the car in drive after a sales call, ask yourself: What went well? What did I miss? What question should I have asked? 5. Shut Up After the Question Mark: When you ask a tough, high-value question, stop talking. The gold in enterprise sales lives on the other side of an uncomfortable silence.   About the Guest: Luke Hostetter is an Enterprise West Account Executive at NiCE, where he helps large enterprises transform customer experience (CX) and service automation through AI. Originally from Lancaster County, Pennsylvania, Luke cut his teeth negotiating high-volume dealer arbitrations at Manheim Auto Auction before moving to Colorado at age 24, where he grew a five-state B2B territory at Decore-ative Specialties from $750K to $4.8M ARR and earned three consecutive Top Producer Awards.   Connect with Luke Hostetter & Walter Crosby: - Luke Hostetter on LinkedIn (Enterprise West Account Executive at NiCE) - Walter Crosby on LinkedIn: https://www.linkedin.com/in/walterlcrosby/ - Helix Sales Development: https://helixsalesdevelopment.com/ - Sales & Cigars Podcast: https://salesandcigars.com/   Hashtags: #SalesAndCigars #WalterCrosby #LukeHostetter #EnterpriseSales #ConsultativeSelling #SalesLeadership #B2BSales #SPINSelling #CigarLifestyle #Montecristo

  2. Oct 6

    "You're Not for Everybody" with Steve Van Diest

    Steve Van Diest joins Walter Crosby to talk about cigars, community, executive coaching, authentic leadership, and why business owners need people who are willing to challenge them. Episode Overview What makes a cigar such a powerful catalyst for conversation? Walter sits down with Steve Van Diest, entrepreneur, executive coach, and Growth Catalyst with Acumen, inside Steve's home cigar lounge—a space intentionally designed for community, connection, and honest conversations. Steve shares how cigars became part of his life during some of his most difficult seasons and eventually became a way to bring people together. His "Shalom Lounge" now serves as a gathering place for clients, business owners, friends, and family. The conversation moves from cigars into the realities of entrepreneurship and leadership. Steve explains why business owners need more than systems and strategies—they need trusted people willing to challenge them, ask difficult questions, and help uncover what's really happening beneath the surface. Walter and Steve also dig into sales, authenticity, mentorship, and why the best salespeople approach their work with a desire to help people rather than simply close transactions.   Episode Highlights Why cigars create space for deeper conversations The story behind Steve's home cigar lounge How Steve went from ministry to entrepreneurship and executive coaching Why business owners need a trusted peer group The difference between advice and experience-based coaching Why company values need to influence actual decisions The importance of vulnerability and accountability in leadership Why entrepreneurs can't hide behind bravado How authenticity changed Steve's approach to prospecting Why great salespeople need skillful hands, a tender heart, and thick skin Walter's philosophy that sales is ultimately about helping people Why the next generation needs experienced mentors willing to share their mistakes   Key Takeaways Cigars create commitment to conversation. When two people light a cigar, they're committing time to each other. That creates room for conversations that often don't happen over a quick coffee or drink. Business owners need people who will challenge them. A trusted peer group can expose blind spots, challenge assumptions, and provide perspectives that even a great one-on-one advisor may not see. Values have to be lived. Core values shouldn't simply appear on a wall or website. They should serve as a filter for hiring, leadership, and business decisions. Authenticity matters in sales. Prospects can recognize when someone is performing. Steve learned that becoming more comfortable with who he was made him more effective at building relationships. Sales is about helping people. Walter argues that the foundation of great selling isn't manipulation or transactions—it's genuinely wanting to help someone solve a problem.   Who Should Listen This episode is for business owners, CEOs, sales leaders, entrepreneurs, executive coaches, and anyone interested in building stronger relationships while becoming a more authentic leader.   Links & Resources Acumen — Peer advisory communities for business owners and leaders Holy Smokes — Community connecting faith and cigars How to Build a Non-Anxious Life — John Delony The Shack — William P. Young EOS / Entrepreneurial Operating System Camino de Santiago   Continue the Conversation Want to continue talking about sales, leadership, and building stronger sales organizations? Join the Sales Integrator Community, a free community for salespeople and sales managers featuring coaching insights, practical sales tools, resources, and conversations with Walter. Join the Sales Integrator Community   Subscribe to Sales & Cigars Sales & Cigars is hosted by Walter Crosby, the Sales Integrator with Helix Sales Development. Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you listen. Listen to the full episode and more Sales & Cigars conversations The only smoke we blow is from cigars.

  3. Sep 8

    Sales, Cigars, and the Relationships That Build a Business with Jim Zazenski

    Walter Crosby sits down with entrepreneur Jim Zazenski to talk cigars, relationship-driven sales, building a high-end sign business, hiring salespeople, accountability, mentorship, and the lessons learned from decades in business. What can a cigar shop teach you about sales, relationships, leadership, and building a business? Quite a bit. In this episode of Sales & Cigars, Walter Crosby sits down with Jim Zazenski at Edward's Pipe & Tobacco in Englewood, Colorado—a shop Jim has been frequenting for more than 20 years. The conversation begins with cigars and the unique relationships that form around them. For Jim, cigar shops have become much more than places to smoke. They are places where friendships are built, business gets discussed, perspectives are challenged, and even an informal "board of directors" can emerge over a few good sticks. From there, Walter and Jim dig into Jim's career and the growth of his custom manufacturing sign company, including its work on high-end properties throughout Las Vegas. Jim explains why his company refuses to compete simply on price, how value engineering helps protect both quality and margin, and why doing the right thing for a customer can be far more valuable than maximizing a single transaction. They also get deep into the realities of managing salespeople: hiring mistakes, compensation plans, account concentration, prospecting, autonomy, accountability, and the danger of letting a successful salesperson become too comfortable. It is a conversation about cigars, certainly—but underneath it is a discussion about relationships, standards, hard work, and what it really takes to build something that lasts.   About Jim Zazenski Jim Zazenski is an entrepreneur with a background spanning engineering, operations, sales, marketing, and custom manufacturing. His company specializes in high-end interior signage and wayfinding solutions for complex properties, including extensive work throughout Las Vegas. He is also a longtime cigar enthusiast who has spent more than two decades frequenting Edward's Pipe & Tobacco in Englewood, Colorado. His daily cigar of choice? A Padrón 5000. And his philosophy is equally straightforward: Life is too short to smoke a bad cigar.   Continue the Conversation Want more conversations about sales, entrepreneurship, leadership, and, of course, cigars? Listen to the full episode of Sales & Cigars here: https://helixsalesdevelopment.com/podcast/ The only smoke we blow is from cigars.

  4. Aug 25

    A New Chapter for Sales & Cigars

    A New Chapter for Sales & Cigars Sales & Cigars is changing. In this behind-the-scenes episode, Walter Crosby sits down with producer Mark Labriola II to talk about the next chapter of the podcast—and why it was time to make a shift. After years of remote conversations, the show is moving toward a more immersive, in-person format with stronger production, longer conversations, and a much bigger emphasis on cigars. But the core of the show isn't changing. Sales, entrepreneurship, leadership, and the real experiences behind building a business will still drive the conversation. The difference is that those topics will now come through more naturally—over cigars, face-to-face, in environments designed for deeper and more interesting conversations. Walter and Mark talk candidly about Zoom fatigue, storytelling, production value, building authority through podcasting, and why the best conversations often happen when you stop trying to force the "perfect" interview. Consider this your preview of what's coming next.   Episode Highlights Why Sales & Cigars is changing its format Moving away from primarily remote interviews toward in-person conversations Why listeners are experiencing Zoom and remote-video fatigue Bringing cigars further to the forefront of the show Creating more natural conversations around sales and entrepreneurship Why face-to-face conversations create different energy Increasing the production quality of the podcast Moving toward longer-form conversations driven by chemistry rather than a rigid clock The role podcasting can play in building authority and thought leadership Creating more short-form content between full episodes Taking Sales & Cigars into cigar lounges and potentially other cities What listeners can expect from the upcoming season   What's Changing More cigars. Cigars will become a bigger part of the conversation—not simply as branding, but as a way to learn about guests, their stories, and the experiences that connect people around them. More in-person conversations. Instead of another remote video call, Walter will increasingly sit across from guests and let conversations unfold naturally. Better production. The new episodes will feature stronger visuals, better sound, and environments that better reflect the personality of Sales & Cigars. Longer conversations. Rather than forcing every episode into the same structure, conversations will go as long as the chemistry and subject matter warrant. The same business value. Sales, leadership, entrepreneurship, and growth remain at the heart of the show. The goal is simply to uncover those lessons through more organic conversations.   Why the Change? Remote podcasting made conversations possible during a period when nearly everything moved online. But today, many people spend their entire workday moving from one virtual meeting to another. Another split-screen interview can easily become something to scroll past. The new Sales & Cigars aims to create something different: the feeling that you're sitting in the room while two people have a conversation you actually want to hear. The objective is still to educate—but also to entertain, tell better stories, and create the kinds of conversations that lead to unexpected ideas.   Who Should Listen This episode is especially valuable for: Longtime Sales & Cigars listeners wondering what's next Entrepreneurs who enjoy candid conversations about business Sales professionals looking for practical ideas without another scripted interview Cigar enthusiasts interested in the stories behind what people smoke and why Business owners using content to build authority and grow their brand Anyone interested in the behind-the-scenes evolution of a podcast   Want to Be Part of the New Format? Have a great cigar story? An entrepreneurial journey worth talking about? A sales lesson learned the hard way? As Sales & Cigars expands its in-person format, Walter and the team are looking for interesting people and conversations—potentially from cigar lounges and cities around the country. Reach out to the Sales & Cigars team if you think there's a conversation worth having.   Continue the Conversation The same philosophy behind the new Sales & Cigars format also drives the Sales Integrator Community: better conversations, practical learning, and access to ideas that help sales professionals improve. The community is built specifically for salespeople and sales managers who want an edge and want support from someone who has spent more than 40 years learning the profession the hard way. Inside, members can access coaching insights, practical sales tools, resources, and ongoing conversations designed to help them get better at the craft. Free forever. Special founding member badges are available for the first 250 members. Join the Sales Integrator Community here: https://helix-community.circle.so/join?invitation_token=8b6622d942c852339d856b2af3504123cf9476e2-8b78b151-d94f-46df-a26b-ec4a6df24460   Subscribe to Sales & Cigars Sales & Cigars is hosted by Walter Crosby, the Sales Integrator with Helix Sales Development. The new season begins rolling out with more in-person conversations, more cigar stories, and more of the sales and entrepreneurial lessons that have always been at the heart of the show. Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you listen. The only smoke we blow is from cigars.

  5. Jul 28

    Core Values, Accountability, and Getting the Founder Out of Sales

    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, and why companies must be willing to make difficult decisions when employees do not align with the culture. The conversation also explores why the best salesperson is rarely the best sales manager, how founder-led companies become too reliant on the CEO to close deals, and why accountability must apply to culture as much as performance. If you are still the best closer in your company—or your core values only live on the wall—this episode will give you plenty to think about. Episode Highlights Why Traction remains one of the most transformative books for entrepreneurs How Great by Choice helps leaders test ideas before making major bets Jim's journey from entrepreneurship to EOS implementation Why EOS works through simple tools and shared language Why core values should be discovered, not invented How leadership teams can uncover values from their best employees Why core values must be used as a business tool How to address employees who perform well but damage the culture Why a "moldy blueberry" can quickly affect the rest of the team The danger of promoting top salespeople into management without support Why founders struggle to step away from the sales seat How accountability conversations help people improve Key Takeaways Simple does not mean easy. EOS provides straightforward tools and language, but leaders still have to do the hard work of implementation and accountability. Core values already exist inside the business. The goal is not to invent impressive words. It is to identify the behaviors shared by the people who best represent the company. Values are only useful when they guide decisions. Core values should influence hiring, coaching, promotions, performance conversations, and terminations. Culture must apply to top performers too. A salesperson who hits their number but damages the team cannot be exempt from accountability. It may be better to have no core values than fake ones. When leaders tolerate behavior that contradicts the stated values, they weaken trust across the organization. The best salesperson is rarely the best sales manager. Selling and managing require different skills, including coaching, patience, process, and accountability. Founders get pulled back into sales because it feels natural. They built the company through relationships and selling, but long-term growth requires developing a team that can perform without them. Accountability is an act of support. Clear feedback gives employees the chance to improve, align with the culture, and become more successful.   Who Should Listen This episode is especially valuable for: Founders who are still the primary closer in the company Entrepreneurs considering EOS Sales leaders building accountability across their teams Companies reviewing or redefining their core values CEOs dealing with high-performing employees who damage the culture Leadership teams trying to create consistency across the organization Business owners who want the sales department to run without them   Links & Resources EOS Worldwide https://www.eosworldwide.com Contact Jim Coyle jim.coyle@eosworldwide.com Traction by Gino Wickman Great by Choice by Jim Collins and Morten T. Hansen Enshittification by Cory Doctorow   Continue the Conversation If this episode made you think differently about accountability, leadership, culture, or how to get the sales department running without everything flowing through the founder, join the Sales Integrator Community. The community is built exclusively for salespeople and sales managers who want an edge and practical support from someone who has learned the hard way over 40 years in sales. Inside, members can access coaching insights, sales tools, practical resources, and ongoing conversations designed to help them improve their craft and lead more effectively. Free forever. Special founding member badges are available for the first 250 members. Join the community here: https://helix-community.circle.so/join?invitation_token=8b6622d942c852339d856b2af3504123cf9476e2-8b78b151-d94f-46df-a26b-ec4a6df24460   Subscribe to Sales & Cigars Sales & Cigars is hosted by Walter Crosby, the Sales Integrator with Helix Sales Development. Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you listen. The only smoke we blow is from cigars.

  6. Jul 14

    AI Isn't Coming for You Job. It's Coming for Your Excuses

    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 salespeople, AI is raising the standard by eliminating excuses and exposing those who rely on shortcuts instead of skill. Walter explains why trust, judgment, curiosity, and meaningful conversations remain the true competitive advantages in complex B2B sales. He also introduces the new Sales Integrator Community, a free resource created to help salespeople and sales managers continue developing their craft through coaching, practical tools, and ongoing discussions. Whether you're a salesperson worried about AI, a sales manager coaching your team, or a CEO building a sales organization, this episode offers practical advice on how to embrace technology without losing the human advantage. Episode Highlights Why AI isn't replacing salespeople—it's exposing average ones Introducing the new free Sales Integrator Community Why great salespeople don't automatically become great sales managers How AI should be used as a tool—not a replacement Why personalization isn't the same as genuine connection Building trust through conversations, not automation How AI can improve preparation, research, and consistency Why judgment is becoming one of the most valuable sales skills Coaching salespeople to make better decisions Why authentic human relationships will become even more valuable as AI evolves Key Takeaways AI raises the standard—it doesn't eliminate salespeople. The future belongs to sales professionals who learn to leverage AI while continuing to build trust and solve complex business problems. Average performers who rely on automation instead of relationships will struggle. Trust can't be automated. AI can generate emails, summarize information, and prepare research, but buyers still choose people they trust. Authentic conversations remain the foundation of complex sales. Judgment creates competitive advantage. Knowing when to ask another question, when to challenge a prospect, and how to interpret information requires experience and critical thinking that AI can't replace. AI belongs in preparation—not persuasion. Use AI to research companies, organize information, write first drafts, summarize meetings, and automate repetitive tasks so you can spend more time having meaningful conversations. More activity doesn't mean better results. AI makes it easy to send more emails and create more content, but quantity without relevance simply creates more noise in an already crowded marketplace. Managers still have to coach. Technology cannot replace coaching. Sales managers develop judgment by asking better questions, helping reps think critically, and creating opportunities for continuous improvement. Being human is becoming more valuable. As AI-generated content becomes more common, authenticity, empathy, curiosity, and genuine relationships become stronger differentiators. Who Should Listen This episode is especially valuable for: B2B sales professionals Sales managers coaching growing teams Entrepreneurs building scalable sales organizations CEOs concerned about AI's impact on revenue Salespeople looking to use AI more effectively Anyone who wants to stay competitive as sales continues to evolve Links & Resources Helix Sales Development Sales Integrator Community Claude AI Walter Crosby   The Sales Integrator Community Walter created the Sales Integrator Community exclusively for salespeople and sales managers looking to sharpen their skills and continue growing. Inside you'll find: Sales coaching insights Practical sales tools and resources Real-world strategies from over 40 years of experience Ongoing discussions and Q&A Blog content and training materials Tips shared directly from Walter's coaching sessions Free forever. The first 250 founding members receive a special Founding Member badge. Join the community here: https://helix-community.circle.so/join?invitation_token=8b6622d942c852339d856b2af3504123cf9476e2-8b78b151-d94f-46df-a26b-ec4a6df24460   Continue the Conversation How are you using AI in your sales process? Are you using it to automate busy work—or to become a better salesperson? Join the conversation inside the Sales Integrator Community and learn alongside other sales professionals committed to improving their craft.   Subscribe to Sales & Cigars Sales & Cigars is hosted by Walter Crosby, founder of Helix Sales Development. Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you get your podcasts. The only smoke we blow is from cigars.

  7. Jun 30

    Entrepreneurship, Risk, and the Next Generation of Leaders

    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 essential to the American economy, why self-discipline matters more than ideas, and why the next generation needs new models of ownership that match how they want to work and live. Reed also breaks down his approach to franchising, leadership development, and identifying the people who have the language, focus, and courage to become successful entrepreneurs.   Episode Highlights Why entrepreneurship is deeply connected to America's growth Reed's family history of immigration, farming, ownership, and opportunity The early lessons Reed learned from selling gum and building dorm lofts Why owning your job comes before owning a business How coming alongside an owner teaches entrepreneurial thinking Why the next generation wants autonomy before opportunity Reed's vision for building app-driven franchise opportunities Why fear and lack of focus are the two biggest threats to entrepreneurs How language reveals whether someone is ready to own a business Why small bets matter before taking big risks   Key Themes & Takeaways Entrepreneurship starts with ownership. Before someone owns a company, they need to learn how to own their work. Value gets noticed. When people create value, the right leaders recognize it and reward it. Autonomy is changing entrepreneurship. Younger generations want control over how, where, and when they work. Fear and focus determine success. Entrepreneurs either get stuck because they are too afraid to move forward, or because they cannot focus long enough to win. Language reveals mindset. How people talk about responsibility, blame, and opportunity often reveals whether they are ready to lead. Risk should be calculated. Entrepreneurs do not avoid risk. They make smaller bets first and learn before firing the cannonball. Letting people go can create opportunity. Keeping the wrong person in a role can hold back both the company and the person who could thrive somewhere else.   Who Should Listen This episode is especially valuable for: Entrepreneurs thinking about the next generation of ownership Young professionals who want to build something of their own Business owners hiring or developing future leaders Franchise leaders looking for better ways to evaluate candidates Salespeople who want to think more like owners Anyone interested in discipline, risk, and entrepreneurial growth   Links & Resources The Next in Leadership https://thenextinleadership.com Reed Nyffeler Transform Through Purpose by Reed Nyffeler Lead Exponentially by Reed Nyffeler   Continue the Conversation If this episode made you think differently about ownership, discipline, sales, or what it really takes to build something, join the Sales Integrator Community. It's built exclusively for salespeople and sales managers who are looking for an edge—and for professionals who want support getting their questions answered by someone who has learned the hard way over 40 years. Free forever. Special founding member badges are available for the first 250 members. Join here: https://helix-community.circle.so/join?invitation_token=8b6622d942c852339d856b2af3504123cf9476e2-8b78b151-d94f-46df-a26b-ec4a6df24460   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.

  8. Jun 16

    Accountability, Visionaries, and the Right-Hand Seat

    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 expectations without slipping into micromanagement. Matt also explains why many business problems are really people problems—and why having a trusted right hand can help founders get out of seats they should no longer be sitting in. If you are a visionary leader trying to scale, this episode is worth your time.   Episode Highlights Why founders often struggle to move from doing to leading How accountability breaks down when expectations are unclear Why working sessions can become necessary when execution stalls The danger of visionaries staying one or two levels too deep in the business How sales leaders can work better with founder-led organizations Why trust between a visionary and sales leader is critical The role of a fractional COO as operator, advisor, and accountability partner Why third-party perspective can help resolve leadership tension How to identify when your business needs a trusted right hand   Key Themes & Takeaways Accountability starts with clear expectations. People cannot execute against vague direction. Leaders must define what success looks like. Visionaries often need help getting out of the way. Founders built the business by doing everything, but scaling requires them to release control in the right places. Execution problems are often people problems. Missed targets, stalled growth, and lack of follow-through usually connect back to communication, clarity, or accountability. Trust must be intentionally built. When founders bring in sales leaders or operators, information flow and role clarity are essential. A strong right hand creates leverage. The right operator helps translate vision into action, hold people accountable, and reduce chaos inside the business. Outside perspective can reduce friction. Sometimes a neutral third party helps leaders hear each other more clearly and move through tension faster.   Who Should Listen This episode is especially valuable for: Visionary entrepreneurs who feel stuck in the weeds Founders looking for a trusted right hand or integrator Sales leaders working inside founder-led businesses CEOs struggling with accountability across the team Service-based businesses trying to scale operations Leaders who know the company needs structure but are unsure where to start   Links & Resources Sinclair Ventures https://sinclairventures.com Matt Haney matt@sinclairventures.com Matt Haney on LinkedIn   Continue the Conversation If this episode made you think differently about accountability, leadership, or how to build a business that can scale without everything running through you, join the Sales Integrator Community. It's built exclusively for salespeople and sales managers who are looking for an edge—and for professionals who want support getting their questions answered by someone who has learned the hard way over 40 years. Free forever. Special founding member badges are available for the first 250 members. Join here: https://helix-community.circle.so/join?invitation_token=8b6622d942c852339d856b2af3504123cf9476e2-8b78b151-d94f-46df-a26b-ec4a6df24460   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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5
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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!

Information

  • Creator
    Walter Crosby
  • Years Active
    2021 - 2026
  • Episodes
    99
  • Rating
    Explicit
  • Copyright
    © 2021 Walter Crosby
  • Show Website
    Sales and Cigars

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