Sales and Cigars

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.

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.

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.

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 [email protected]

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.

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.

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.

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 [email protected]

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.

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 jump into solution mode too quickly.

The conversation also dives into one of John's biggest pieces of advice for sales professionals: invest in yourself. Don't wait for your company to train you. Don't complain that no one is developing you. Your career is your responsibility.

From coaching and mentorship to business acumen and sales-marketing alignment, this episode is a reminder that the best salespeople never stop learning.

Episode Highlights

• Why SPIN Selling still matters in modern sales
• The difference between hearing and active listening
• Why silence after a good question is powerful
• How salespeople can stop rushing into solution mode
• Why every salesperson should learn a sales methodology
• John's advice to invest in yourself before blaming your company
• The ROI of hiring a coach or finding a mentor
• Why sales, sales leadership, and CEO roles can feel lonely
• The importance of business acumen in today's sales environment
• How salespeople can bring value through insight, not just products
• Why a great sales call should be valuable enough to pay for

Key Themes & Takeaways

• Great salespeople ask better questions. The best reps do not rush to pitch. They slow down, listen, and dig deeper.
• Silence is part of the process. When a prospect pauses after a strong question, don't interrupt. Let them think.
• Your career is your responsibility. If your company is not investing in your development, invest in yourself.
• Coaching pays for itself. A good coach or mentor can challenge your thinking, expand your goals, and accelerate growth.
• Sales can be lonely. Whether you are carrying a bag, leading a team, or running a company, you need people who can challenge and support you.
• Business acumen matters more than ever. Salespeople need to understand how businesses operate, how decisions get made, and how their solution impacts the whole organization.
• Value starts before the deal closes. A sales conversation should help the buyer think differently, even before they buy anything.

Who Should Listen

This episode is especially valuable for:

• Salespeople who want to take ownership of their career
• Sales leaders trying to develop stronger, more independent reps
• CEOs and entrepreneurs who want better sales conversations
• Teams looking to improve discovery and active listening
• Revenue leaders focused on sales and marketing alignment
• Anyone who wants to become more valuable in every business conversation

Links & Resources

SPIN Selling by Neil Rackham

Pipeliner CRM https://pipelinersales.com

Sales Pop https://salespop.net

John Golden on LinkedIn

Continue the Conversation

If this episode made you think differently about sales, leadership, or how to take ownership of your career, 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.

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 admitting mistakes. The discussion explores why values should align with strategy, how culture impacts operational performance, and why leaders must actively model the behaviors they expect from their teams.

This conversation is practical, honest, and highly relevant for leaders trying to build healthy accountability without losing connection and trust.

Episode Highlights

• Why many companies misunderstand core values
• Mike's early "life raft exercise" for defining values
• How humor unintentionally created unhealthy cultural behaviors
• The rubber chicken story and the impact of public embarrassment
• Lessons from lean thinking and Edwards Deming
• Why fear destroys operational improvement
• How respect became foundational to nSight's strategy
• Why core values should evolve as the business evolves
• The importance of making values memorable and teachable
• nSight's RSVP framework:
• Respect and Connect
• Servant's Heart
• Value Value
• Progress Over Comfort
• Why leaders must adapt to the values first
• The difference between a workplace family and a high-performing team
• Why accountability and connection must coexist

Key Takeaways

Core values should support strategy

Values are not just words that sound good. They should reinforce the behaviors required for the business to succeed.

Culture can create unintended consequences

Even positive-sounding values can create fear, avoidance, or unhealthy team dynamics if they are not examined honestly.

Fear prevents improvement

Organizations cannot solve problems when employees feel unsafe admitting mistakes or identifying issues.

Respect must come before humor

Fun cultures work best when people first feel respected, safe, and valued.

Leaders must model the values

Core values are not just expectations for employees. Leaders must demonstrate them consistently themselves.

Accountability and connection belong together

Strong cultures balance caring deeply about people while still maintaining standards and honest feedback.

Who Should Listen

• CEOs and founders refining company culture
• Leaders implementing EOS or operational frameworks
• Managers trying to improve accountability and trust
• Entrepreneurs building teams through growth and change
• Sales leaders focused on culture-driven performance

The Sales Integrator Community Invite

Exclusively for salespeople and sales managers who are looking for an edge.

For those sales professionals who want support in getting their questions answered by someone who has learned the hard way over 40 years.

Free forever. Special badges created for the first 250 founding members.

Join the Sales Integrator Community

Subscribe to Sales & Cigars

If you want real conversations about entrepreneurship, leadership, culture, and building companies with intention, subscribe to Sales & Cigars on Apple Podcasts, Spotify, or YouTube.

The only smoke we blow is from cigars.

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 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.