8 Business Lessons From CEOs Who Built Companies That Last

Longevity in business is rare, making the stories of lasting companies invaluable.

Insights gathered from interviews and reflections by world-class CEOs and founders such as Airbnb’s Brian Chesky, Canva’s Melanie Perkins, and Shopify’s Tobi Lütke reveal timeless lessons.

What we want to achieve today is to both provide inspiration to our readers and to give leaders tools can apply immediately.

Lesson #1: Build Relentless Clarity Around Vision and Mission

A company without a clear vision can easily drift into confusion, wasting time and energy on misaligned initiatives.

Roux Stevens emphasizes that defining vision should be the very first step, even before structure, hiring, or execution. Once vision is articulated, every decision has an anchor point.

Mark MacLeod adds that resilient CEOs never treat vision as a static phrase on a wall but as a living compass that shapes culture, operations, and strategy.

Tobi Lütke at Shopify provides a powerful example by embedding vision into the company’s DNA, ensuring every team member worked toward a shared north star.

When vision blurs, motivation declines, execution falters, and progress slows. Clarity eliminates unnecessary debates and prevents teams from scattering their energy across low-value activities.

A crystal-clear mission also creates trust across the organization, as employees know why they are building and how their efforts matter.

Several elements reinforce clarity:

• Define the north star early: Establish what the company exists to achieve and make it non-negotiable.
• Translate vision into daily work: Ensure teams can see how their actions link directly to larger goals.
• Repeat until it sticks: Vision must be communicated constantly, not just during annual retreats.
• Adapt language, not essence: The way vision is explained may evolve, but its core must remain steady.

A well-defined vision guides leadership in moments of uncertainty, anchors culture when markets shift, and inspires teams to pursue excellence despite obstacles.

Leaders who fail to protect clarity invite drift, while those who maintain it create organizations that can endure over decades.

Lesson #2: Design for Longevity, Not Just Growth

Growth may grab headlines, but longevity creates a legacy.

Companies that endure resist the temptation to chase short-term expansion without long-term planning.

Just as homeowners use bridging home loans to navigate the short-term financial gap between buying and selling properties, lasting companies prepare financially and structurally for transitional periods without jeopardizing their broader vision.

Monocle often showcases leaders who embed adaptability into their business model, such as Moebe’s modular furniture, designed to evolve with customer needs.

Melanie Perkins at Canva focused not only on scale but also on simplicity and purpose, creating a company that could grow sustainably without losing direction.

Longevity is achieved by preparing for flexibility, not by assuming markets will always remain stable.

Businesses that design with future-proofing in mind avoid desperate reinventions when challenges hit. They remain steady while competitors scramble.

Steps to prioritize longevity include:

• Prioritize adaptability: Build products, systems, and teams that can evolve with changing markets.
• Balance impact with profit: Growth matters, but sustainable impact ensures continuity.
• Think decades, not quarters: Frame decisions in terms of what will matter in 10 years, not just today.
• Embed purpose into culture: Employees stay committed when they believe the work matters long-term.

Lesson #3: Obsess Over the Customer Experience

Customer loyalty is not earned through surface-level gestures but through deeply empathetic design.

Brian Chesky’s Airbnb “11-star experience” model asked teams to imagine levels of service so extraordinary that customers would never forget them.

By thinking in extremes, Airbnb designed experiences that far surpassed standard expectations.

Companies highlighted in Monocle, such as Tennibot, show that solving specific pain points creates natural loyalty.

Customers return to brands that anticipate needs and remove frustrations before they even arise.

Leaders who focus on experience create environments where customers become promoters, not just buyers.

Ways to elevate customer experience include:

• Anticipate needs: Go beyond fixing problems to predicting them before they appear.
• Design extreme scenarios: Use thought experiments like Chesky’s model to stretch creativity.
• Map pain points: Identify where customers struggle and focus resources there.
• Delight with small wins: Tiny thoughtful touches create lasting emotional connections.

Lesson #4: Stay Curious, Learn Fast, Reflect Often

Curiosity drives reinvention. Mark MacLeod points out that CEOs who carve time for reflection, mindfulness, and constant learning stay sharper.

Estelle Roux emphasizes that trial, error, and iteration refine business models and make leaders more resilient.

Curiosity creates intellectual humility, keeping leaders open to feedback rather than locked into old assumptions.

Reflection prevents repeated mistakes and builds cycles of improvement. Leaders who are curious, quick to learn, and unafraid to adjust remain relevant even in unpredictable environments.

Approaches that reinforce curiosity include:

• Create space for reflection: Schedule time for learning, not just execution.
• Experiment boldly: Small trials provide insights that transform future strategy.
• Embrace failure as data: Each misstep provides valuable lessons when analyzed with honesty.
• Stay humble: Growth requires acknowledging that no one has all the answers.

Lesson #5: Build Teams That Scale With You

No founder builds a lasting company alone. Roux reminds leaders that greatness is collective.

Frank Slootman at Snowflake exemplifies the power of high-output teams that tolerate no passengers.

Larry Ellison’s ability to delegate tasks outside his core strengths further highlights the importance of relying on capable people.

Teams that evolve alongside leadership prevent bottlenecks and amplify growth.

A CEO’s role is not to do everything but to ensure the right people are in the right places.

When this alignment is achieved, scaling becomes possible without constant micromanagement.

Principles for building scalable teams include:

• Hire for performance, not comfort: Choose people who elevate standards.
• Delegate strategically: Retain core strengths, delegate what distracts.
• Build culture of accountability: Teams must own outcomes, not just tasks.
• Evolve talent with scale: Early hires may not always be suited for later stages.

Lesson #6: Simplify Ruthlessly to Achieve Speed

Simplicity is often the competitive advantage most overlooked. Canva’s culture is built on removing complexity in design, hiring, and execution.

Tobi Lütke once canceled a billion-dollar initiative when it no longer aligned with company direction, showing courage in prioritizing clarity over sunk costs.

Mark Zuckerberg simplified his daily life by reducing decision fatigue, eliminating distractions that could pull him off course.

Complexity slows execution, while simplification accelerates it. Leaders who are ruthless about reducing unnecessary steps can respond faster to opportunities and threats.

Methods for simplification include:

• Cut failing projects quickly: Do not let sunk costs dictate decisions.
• Remove decision clutter: Automate or streamline small choices.
• Standardize processes: Clarity in operations prevents wasted time.
• Focus on essentials: Keep teams aligned on what truly matters.

Lesson #7: Build Around Your Strengths (and Know Your Limits)

Self-awareness is one of the most underrated leadership qualities.

Tobi Lütke structured his role to maximize his strengths in product and technology while delegating media responsibilities to others.

Roux Stevens sharpened her business once she discovered her strength in community-building for career women.

Leaders waste energy trying to be good at everything, diluting their impact.

Success accelerates when leaders focus on natural strengths and surround themselves with complementary talent. Recognizing limits is not weakness but wisdom.

Strategies for building around strengths include:

• Audit personal strengths: Identify what creates the most value.
• Delegate without guilt: Give away tasks that drain focus or talent.
• Surround with complementary skills: Fill gaps instead of duplicating strengths.
• Stay aligned with passion: Energy flows strongest when work matches natural abilities.

Lesson #8: Protect Your Energy or Burn Out Trying

Burnout undermines even the most brilliant leaders.

Melanie Perkins discovered early that sustaining Canva’s growth required prioritizing her health. Brian Chesky emphasizes managing energy instead of glorifying endless hustle.

Mark MacLeod insists that healthy, balanced leaders create stronger companies.

Energy is not a personal indulgence but a strategic resource.

Without balance, decision-making suffers, culture weakens, and momentum collapses.

Leaders who protect their energy create organizations that thrive longer and stronger.

Ways to protect energy include:

• Prioritize recovery: Rest and balance fuel better performance.
• Reject hustle myths: Sustainable progress beats unsustainable grind.
• Protect focus time: Energy is preserved when distractions are limited.
• Value health as capital: Physical and mental well-being must be seen as assets.

Summary

Eight lessons converge on one truth: companies that endure are built on clarity, adaptability, customer obsession, curiosity, scalable teams, ruthless simplicity, self-awareness, and energy management.

Building a company that lasts is not about avoiding risk but about sustaining momentum and vision over decades.

Leaders can reflect on which lessons are already practiced and which require sharper focus.