The Grit Series Part 2: Grit in Action

The Grit Series Part 2: Grit in Action

In the first part of this series, we explored the concept of grit—what it is, why it matters, and how startup founders can cultivate it in themselves and their teams. But theory alone isn’t enough. To truly understand grit, we need to see it in action. Real-world stories of entrepreneurs who faced daunting obstacles, setbacks, and skepticism—yet persevered—offer invaluable lessons for anyone on the startup journey.

This article dives into four diverse case studies that showcase grit in the startup world. Each story highlights a different path to resilience, from bootstrapping against the odds to championing sustainability or overcoming personal adversity. Along the way, we’ll extract practical lessons and patterns you can apply to your own entrepreneurial journey.

Why Case Studies Matter

Stories are powerful teachers. While frameworks and strategies are important, it’s the lived experiences of founders that bring the concept of grit to life. Case studies provide context, nuance, and emotional resonance. They show us not just what to do, but how it feels to persist when the odds are stacked against you. For founders, these stories can inspire hope, offer tactical insights, and remind us that behind every success is a trail of setbacks, pivots, and relentless effort.

Case Study 1: Sara Blakely and Spanx – Turning Rejection into Resilience

Sara Blakely’s journey from door-to-door fax machine saleswoman to billionaire founder of Spanx is a masterclass in grit. In the late 1990s, Blakely had a simple but revolutionary idea: footless pantyhose that would smooth and flatter women’s bodies without uncomfortable seams or visible lines. She had no background in fashion or manufacturing, no industry contacts, and only $5,000 in savings. What she did have was a burning passion to solve a problem she personally experienced—and the perseverance to see it through.

Blakely spent two years developing her prototype, facing rejection after rejection from hosiery mills across North Carolina. Most manufacturers dismissed her idea outright, and some even laughed at her. Undeterred, she kept knocking on doors, eventually finding one mill owner who agreed to take a chance on her product after his daughters encouraged him to listen.

But the challenges didn’t end there. Blakely had to convince retailers to stock her product, a daunting task for an unknown entrepreneur with no marketing budget. She personally pitched Spanx to department stores, often demonstrating the product herself in store bathrooms. Even after Neiman Marcus agreed to carry Spanx, Blakely would visit stores to rearrange displays and educate sales staff, doing whatever it took to get noticed.

Her persistence paid off. Spanx became a sensation, eventually growing into a billion-dollar brand. Blakely’s story is a testament to the power of grit: she faced repeated rejection, worked tirelessly to refine her product, and never lost sight of her mission. Her willingness to do the unglamorous work, to keep going when others would have quit, is what set her apart.

Lesson for Founders:
Rejection is inevitable, but resilience is a choice. When you believe in your vision and are willing to outwork the doubters, you create your own luck. Grit means showing up, again and again, even when the world says “no.”

Case Study 2: Mailchimp – Bootstrapping to a Billion-Dollar Brand

While many startups chase venture capital and rapid growth, Mailchimp’s founders took a different path—one defined by patience, customer focus, and unyielding perseverance. Ben Chestnut and Dan Kurzius started Mailchimp in 2001 as a side project while running a small web design agency in Atlanta. Their goal was simple: make email marketing accessible to small businesses.

In the early days, Mailchimp was anything but glamorous. Chestnut and Kurzius bootstrapped the company, refusing outside investment and funding growth entirely from their agency’s profits. This meant long hours, slow progress, and constant uncertainty. They worked on Mailchimp at night, often questioning whether their product would ever gain traction in a market dominated by well-funded competitors.

The founders faced numerous challenges. They had to build and maintain a complex product with limited resources, all while serving demanding clients and keeping their agency afloat. There were moments when giving up would have been the easier, more rational choice. But Chestnut and Kurzius believed in their mission—and in the value of serving small businesses that were often overlooked by larger competitors.

Their grit was evident in the way they listened to customers, iterated on their product, and reinvested every dollar back into the business. Rather than chasing flashy features or hype, they focused relentlessly on solving real problems for their users. This steady, determined approach paid off. Over the years, Mailchimp grew organically, eventually becoming the world’s leading marketing automation platform for small businesses.

The story doesn’t end there. In 2021, after two decades of bootstrapped growth, Mailchimp was acquired by Intuit for $12 billion. Chestnut and Kurzius had built a global powerhouse without ever taking a dime of venture capital—a rare feat in the startup world.

Lesson for Founders:
Grit isn’t always about dramatic turnarounds or overnight success. Sometimes it’s about showing up, day after day, for years—making incremental improvements, serving your customers, and staying true to your values. Bootstrapping requires a special kind of perseverance, one that values long-term impact over short-term wins.

Case Study 3: Bee’s Wrap – Sustainability Amid Skepticism

Innovation often means swimming against the tide, and few stories illustrate this better than Sarah Kaeck’s journey with Bee’s Wrap. In 2012, Kaeck set out to eliminate plastic waste from her kitchen by reviving an old tradition: coating cotton fabric in beeswax to create a reusable, sustainable food wrap. At a time when single-use plastics were the norm, her idea was met with skepticism from both investors and consumers.

Kaeck faced an uphill battle. Most people were unfamiliar with beeswax wraps, and many doubted that consumers would pay more for a sustainable alternative to plastic wrap. Investors were hesitant to back a product that required educating the market and changing entrenched habits. On top of that, Kaeck had to figure out how to scale production, source sustainable materials, and manage the logistics of a growing business—all with limited resources.

But Kaeck’s belief in her mission never wavered. She persisted, perfecting her product through trial and error, and tirelessly advocating for sustainable living. She built relationships with local beekeepers, experimented with different formulas, and sought feedback from early adopters. When traditional retail channels proved challenging, she turned to farmers’ markets, online sales, and grassroots marketing to build a loyal customer base.

Over time, Bee’s Wrap gained traction. The global movement toward sustainability and reducing plastic waste gave Kaeck’s mission new momentum. Bee’s Wrap became a certified B Corporation, recognized for its commitment to social and environmental responsibility, and grew into a globally recognized brand.

Lesson for Founders:
Grit is about believing in your mission, even when the market is slow to catch on. Innovation often requires educating customers, challenging the status quo, and persisting through skepticism. If you’re committed to a cause bigger than yourself, that sense of purpose can sustain you through the toughest times.

Case Study 4: Howard Schultz and Starbucks – From Poverty to Global Brand

Howard Schultz’s story is one of grit forged in adversity. Raised in public housing in Brooklyn, Schultz grew up in poverty, watching his father struggle with unstable, low-paying jobs. These early experiences shaped his worldview and fueled his determination to build something better—not just for himself, but for others.

After joining Starbucks in 1982 as Director of Retail Operations and Marketing, Schultz was inspired by a trip to Italy, where he experienced the vibrant coffeehouse culture. He envisioned Starbucks as a “third place” between work and home—a community gathering spot that offered more than just coffee. But the company’s original owners were skeptical of his vision, and Schultz faced over 200 rejections from investors when he tried to raise funds to buy the company.

Despite these setbacks, Schultz refused to give up. He eventually acquired Starbucks and set out to transform it into a global brand. The journey was anything but smooth. Schultz navigated crises like the 2008 financial downturn, which threatened the company’s survival. He made bold decisions to close underperforming stores, invest in employee benefits, and double down on customer experience—all while facing criticism from Wall Street.

Schultz’s grit was evident in his willingness to make tough choices, to listen to employees and customers, and to stay true to his vision even when it was unpopular. He led Starbucks through adversity, turning it into one of the world’s most recognized brands.

Lesson for Founders:
Grit is about enduring setbacks, staying true to your vision, and leading with integrity. Personal adversity can be a powerful motivator, but it’s the willingness to act on your convictions—and to keep going when others doubt you—that defines true resilience.

Additional Brief Examples of Grit in Startups

While the stories above offer deep dives, countless other founders have demonstrated grit in ways both big and small. Here are a few quick examples:

• Brian Chesky and Joe Gebbia (Airbnb): Faced repeated rejections from investors and struggled for years to find product-market fit. They famously sold novelty cereal boxes to keep the company afloat before Airbnb became a global phenomenon.
• Jan Koum (WhatsApp): Immigrated to the U.S. as a teenager, lived on food stamps, and faced early career rejections. Koum’s perseverance led to the creation of WhatsApp, which was acquired by Facebook for $19 billion.
• Melanie Perkins (Canva): Spent years pitching her idea for a simple online design tool, facing hundreds of investor rejections before finally securing funding and building Canva into a billion-dollar company.

Each of these stories underscores a simple truth: success is rarely linear. The path is often marked by detours, setbacks, and moments of doubt. What separates those who succeed is not just talent, but the willingness to keep going.

Common Patterns in Gritty Founders

Across these case studies, several patterns emerge:

1. Purpose-Driven Mission:
   Founders who are deeply connected to a larger purpose—whether it’s empowering small businesses, reducing plastic waste, or building community—are more likely to persist through adversity.

2. Resilience in the Face of Rejection:
   Every founder faces “no” at some point. Gritty founders treat rejection as feedback, not a final verdict.

3. Adaptability and Willingness to Pivot:
   Grit isn’t about stubbornly sticking to a failing plan. It’s about learning, iterating, and adapting while staying true to your core mission.

4. Long-Term Focus:
   Many gritty founders play the long game, prioritizing sustainable growth and customer value over quick wins.

5. Support Networks:
   Behind every gritty founder is a network of mentors, supporters, and early believers who provide encouragement and perspective.

How to Apply These Lessons

So, how can you apply these lessons of grit to your own startup journey? Here are some actionable steps:

• Reconnect with Your Mission:
  Regularly remind yourself—and your team—why you started. Purpose fuels perseverance.

• Embrace Rejection:
  Treat every “no” as a learning opportunity. Analyze feedback, iterate, and keep moving forward.

• Build a Support System:
  Surround yourself with mentors, peers, and advisors who believe in your vision and can offer guidance during tough times.

• Practice Adaptability:
  Be willing to pivot when necessary, but don’t lose sight of your core values and mission.

• Celebrate Small Wins:
  Grit is built through consistent effort. Acknowledge progress, no matter how incremental.

• Share Stories of Grit:
  Foster a culture where setbacks and perseverance are openly discussed. Encourage your team to share their own stories of resilience.

Conclusion

Grit is more than a buzzword—it’s the foundation of every enduring startup. The stories of Sara Blakely, Ben Chestnut and Dan Kurzius, Sarah Kaeck, Howard Schultz, and countless others remind us that behind every success is a journey marked by setbacks, sacrifice, and relentless effort. Grit is not about never failing; it’s about refusing to give up.

As you navigate your own entrepreneurial path, remember that grit can be cultivated. Draw inspiration from those who have gone before you, learn from their struggles, and apply their lessons to your own journey. Share your own stories of perseverance—they may be just the spark someone else needs to keep going.

Stay gritty. The world needs your vision, your resilience, and your unwavering commitment to making a difference.

4th July 2025