The Winner’s Curse — When Success Breeds Complacency

Success in the Premium Cigar Industry can be blinding. What happens when your biggest win becomes your biggest risk?

What happens when your biggest win becomes your biggest risk?

In the cigar industry, earning a 95-point rating, landing a celebrity shoutout, or going viral online can feel like a turning point — and in many ways, it is. But success also invites complacency.

I’ve seen this across industries. When brands hit that sweet spot, they start trusting momentum to carry them forward. That’s the trap — the moment you believe yesterday’s success guarantees tomorrow’s stability, you’ve already stepped into The Winner’s Curse.

When that happens, cigar makers stop doing the very things that built their reputation in the first place:

✅ They ease up on quality control.

✅ They rush new production to keep up with demand.

✅ They push out new releases just to “stay hot.”

✅ They assume retailers will keep pushing their product without added effort.

This is The Winner’s Curse — the false belief that past success guarantees future stability.

The reality? Success puts a target on your back. Competitors are watching, waiting for you to slip — and if you get comfortable, they’ll be ready.

In this blog, we’ll break down how to avoid the Winner’s Curse by balancing five critical elements:

✅ Maintaining a strong, consistent core product line

✅ Innovating with intention — and on your own terms

✅ Controlling your messaging to reinforce your identity

✅ Staying disciplined with internal audits and performance reviews

✅ Building a culture that keeps your team hungry

Success isn’t permanent — unless you make it so. Let’s talk about how. 

How Success Creates Blind Spots

Success doesn’t just create blind spots — it invites them.

When a cigar brand hits big — whether through a top score, a viral moment, or a celebrity endorsement — the natural instinct is to relax. After all, you’ve “made it,” right? That’s where the trap begins.

Success creates a dangerous illusion: that what worked yesterday will keep working tomorrow.

Here’s what that looks like:

✅ Overconfidence in Your Core Product: A cigar maker riding a strong review may assume their top-rated blend is perfect. They stop paying attention to blending discipline, overlook minor changes in taste profile, and let consistency slip.

✅ Innovation Overload: Driven by the need to “stay relevant,” they rush new releases. These cigars may feel rushed or poorly marketed — ultimately confusing consumers and weakening the brand’s identity.

✅ Stagnant Messaging: After landing a 95-point score or earning a wave of online buzz, some brands pull back on their messaging. They assume the work is done — that consumers will just keep coming. But success doesn’t sell itself. The moment you stop reinforcing your story, you start fading from the conversation.

✅ Weakened Internal Discipline: Operations start to loosen. Supply chain reviews, cost analysis, and staff training get less attention. The logic? “We’re on top — we must be doing everything right.”

The truth is, success is often the most vulnerable time for a business. When competitors see you thriving, they double down — improving their portfolio, strengthening retail relationships, and fine-tuning their marketing. They know you’re comfortable — and they’re betting you’ll stay that way.

Complacency is the cigar maker’s biggest risk. The brands that survive long-term aren’t the ones that ride momentum — they’re the ones that stay disciplined when the spotlight hits.

The moment you believe success will sustain itself is the moment you give your competitors an opening.

Building a Strong Core: The Foundation for Sustained Success

When a cigar maker hits the big time — whether through a top rating or viral attention — the instinct is to expand. More blends, more sizes, more releases — the logic is that growth equals momentum.

But expansion without discipline is one of the fastest ways to unravel success.

The cigar makers who survive — and thrive — after achieving success aren’t the ones who chase trends; they’re the ones who build a strong, efficient core product line that becomes the foundation of their brand.

A strong core product line does three things:

✅ It defines your identity. Customers know what to expect from you — and they trust it.

✅ It protects your reputation. While trends come and go, your core line remains the anchor that consumers return to.

✅ It stabilizes your operations. Fewer moving parts make it easier to maintain consistency, manage inventory, and support retailers effectively.

The mistake comes when cigar makers let their core products slip in the rush to keep innovating. A cigar maker riding a 95-point score may assume their core brands are rock solid — but confidence without vigilance is dangerous.

Here’s what that looks like:

• Blending Drift: Small shifts in leaf sourcing, fermentation, quality control, etc. can gradually alter your core (and winning) cigar’s taste profile or performance — often without anyone noticing until it’s too late.

• Inventory Imbalance: When excitement builds around new releases, core inventory often gets overlooked. Retailers end up short on the very products that earned your reputation in the first place.

• Complacency — whether from suppliers, employees, or leadership — puts your core product line at risk. Pressure exposes weak spots fast. If you’re not finding those gaps — your competitors will.

How to Reinforce Your Core Product Line

✅ Audit Your Core Products Regularly: Don’t assume your best-selling cigars are performing just because they’re moving. Conduct regular blind tastings to ensure consistency and gather feedback from trusted retailers and consumers.

✅ Protect Your Supply Chain: Success puts pressure on suppliers. Build relationships with secondary vendors and consistently review product quality — especially for core products. If you’re vertically integrated, horizontally integrated or both, keep a close eye on your internal procedures and controls.

✅ Balance Innovation with Discipline: Innovation is important, but don’t let new releases steal focus from your core. Your foundation should feel like clockwork — steady, dependable, and always delivering on your brand’s promise.

✅ Communicate with Retailers: Many retailers love new releases — but they rely on your core cigars to drive consistent sales. Make sure they understand that your core is still a priority, even as you build excitement for new products.

Your core product line is your insurance policy. It’s the reason your customers found you — and the reason they’ll stay.

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How to Innovate with Intention

✅ Use Analytics to Find Your Moment: Successful brands don’t guess when to innovate — they study their data. Look at your sales patterns, customer behavior, and seasonal buying trends. Then, time your product releases to align with those peaks.

For example:

• Launch a Father’s Day cigar to capture gift-buying momentum.

• Introduce a New Year’s Eve release to position your product as the celebratory smoke of choice.

• Align a limited edition with a brand anniversary or milestone to connect your product to your story.

Launching when the market is quiet often makes a bigger impact than competing for attention at a crowded trade show.

✅ Quality Over Quantity: Innovation fatigue is real. If you’re constantly releasing new products, retailers and consumers stop paying attention. A well-timed, carefully crafted release will outperform three rushed sub-brands every time.

✅ Preserve Your Identity: Successful brands know who they are — and they protect that identity. When you innovate, ensure your new product reflects your craftsmanship, flavor profile, and values.

✅ Don’t Undermine Your Core: Innovation should expand your business — not cannibalize it. Launching a duplicative product or sub-brand before your flagship cigar has fully matured doesn’t create new revenue — it just shifts dollars from one product to another.

Don’t innovate just to stay busy. The smartest brands innovate with purpose.  Time your releases when competitors are quiet, consumers are spending, and retailers are eager for fresh inventory.

Consistency in Messaging: Reinforcing Your Brand Story

Success doesn’t speak for itself — you have to control the narrative.

When your cigar lands a 95-point score, goes viral, or earns a celebrity endorsement, it’s easy to assume that success will carry your brand’s message forward. That’s a mistake.

Success is loud, but it’s also temporary. Once the noise fades, consumers will only remember what you’ve actively reinforced.

The brands that stay relevant are the ones that keep their message consistent.

How to Control Your Brand’s Narrative

✅ Own Your Identity: Don’t let your latest win redefine who you are. Stick to what made you successful — and expand only when research proves it’s worth the risk.

✅ Use Success to Amplify Your Story: When a product scores big or gains unexpected attention, connect that moment back to your brand’s core values. Reinforce the craftsmanship, blending discipline, heritage, or the positioning that defines you.

✅ Keep Retailers Aligned: Retailers shape your brand’s perception in the marketplace. Equip them with clear talking points, POS materials, and product knowledge that reinforce your core message.

✅ Stay in the Conversation: Even between product launches, remain active. Share behind-the-scenes insights, showcase your cigar making processes, or celebrate milestones. Consistency keeps you relevant — even when the buzz fades.

Corporate Culture: Creating a Team That Stays Hungry

Success doesn’t just change your brand — it changes your people.

When your cigars are suddenly flying off shelves, your team feels it. The energy shifts. That same crew that once hustled to earn every sale now starts to believe that success is inevitable.

That’s dangerous.

In my experience, the brands that stay on top are the ones that build a culture that refuses to get comfortable. They create teams that stay motivated — no matter how good things look on paper.

Here’s how they do it:

How to Build a Culture That Fights Complacency

✅ Reward Results — Not Busyness: Success can trick employees into thinking activity equals achievement. The brands that thrive reward outcomes — not just effort. That means measuring KPIs like customer retention, product consistency, and retailer relationships — not just sales numbers.

✅ Encourage Constructive Conflict: Great teams aren’t afraid to challenge bad ideas — even when they come from the top. Foster an environment where employees feel safe raising concerns about quality drift, operational gaps, or weak product ideas. Teams that push back when things feel “off” are the ones that prevent small issues from turning into major problems.

✅ Spot — and Develop — Emerging Leaders: When sales spike, your organization’s flaws become magnified. Leaders who thrived when things were quiet may struggle under the pressure of increased demand. Identify those employees who naturally step up when things get tough — and invest in their development.

✅ Tie Every Role to the Brand’s Identity: Employees lose focus when they forget their purpose. Connect their daily work back to the core values that define your cigars — the company’s positioning and messaging. When employees know they’re part of something bigger, they stay committed even when success starts to feel routine.

✅ Act Like an Underdog — Even When You’re Winning: The brands that stay sharp are the ones that operate like they’re still fighting for relevance. Comfort is the enemy. Assume your competitors are watching — and waiting for you to relax. When employees believe that success is fragile, they stay sharp.

The Bottom Line:

Success shouldn’t make your team comfortable — it should make them disciplined.

Complacent teams lose. Hungry teams win. Build a culture that fights to win — every day. In the final section, we’ll tie everything together — reinforcing how balance across your product, innovation, messaging, and culture is what keeps your brand strong.

Conclusion: Balance Is Everything

The cigar industry rewards discipline.

Success — whether from a 95-point score, a viral moment, or a celebrity endorsement — can feel like a victory lap. But success isn’t the finish line — it’s a test.

The brands that survive aren’t the ones that chase every opportunity. They’re the ones that stay balanced — knowing that growth is fragile and momentum is fleeting.

✅ Protect Your Core: Your core product line is your foundation; the blends that loyal customers keep coming back to. When success hits, don’t let ‘fame’ or new releases pull your attention away from maintaining consistency where it matters most.

✅ Innovate with Purpose: Innovation is important — but innovation without strategy is noise. Find a cadence that makes sense for your business, and don’t let pressure force you into rushed releases that confuse consumers or dilute your identity.

✅ Control the Narrative: Success doesn’t speak for itself. Reinforce your brand’s story consistently — and don’t let a big score or viral moment redefine who you are.

✅ Stay Sharp Internally: Strong sales can hide weak systems. Regular audits, financial reviews, and outside perspectives ensure you’re prepared for future challenges — not just riding the high of recent wins.

✅ Keep Your Team Hungry: Success can soften a strong team. Build a culture that rewards accountability, encourages constructive conflict, and reminds employees that success isn’t permanent — it’s earned every day.

The Bottom Line:

Success isn’t the end of the race — your competition is chasing you — and if you slow down, they’ll pass you. What are you doing today to stay ahead?

Stay disciplined. Stay sharp. Stay humble — and you’ll build a brand that thrives long after the spotlight fades.

Success isn’t just about winning — it’s about knowing what to do once you’ve won.

That’s where The Cigar Profit comes in. We specialize in helping cigar brands navigate the pressures that follow big wins — ensuring your momentum turns into lasting growth. Whether it's reinforcing your core product line, developing an innovation strategy that fits your brand, or sharpening your internal discipline, we provide the insights and strategies to keep you ahead.

Success doesn’t have to be a curse — not if you stay sharp, stay focused, and stay prepared. Let The Cigar Profit show you how. Book your discovery session today: https://www.cigarprofit.com/schedule-exploratory-call