Why Good Entrepreneurs Hire CEOS – Pinky Cole’s Rebound

Entrepreneurship is a rollercoaster ride—one day, you’re at the top, the next, you’re navigating challenges that could make or break your business. In this edition of The Rundown with Ramon, we dive into two powerful business stories: Pinky Cole’s fight to regain control of Slutty Vegan, and Stanley 1913’s approach to sustaining success after a viral boom.

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Both offer unique lessons for entrepreneurs:

  • How founders navigate leadership decisions, including when to hire a CEO.
  • Why brand reinvention is crucial for long-term growth.
  • How businesses can capitalize on trends while staying adaptable.


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Let’s break it all down.

Pinky Cole’s Entrepreneurial Story: Vision, Loss, and Reinvention

Slutty Vegan is more than just a restaurant chain—it’s a movement. Founded by Pinky Cole, the brand gained massive traction, particularly in the Black community, for its bold marketing and commitment to vegan food. But in early 2025, she faced a major setback: she lost control of her company due to financial challenges.

Despite this loss, Cole fought back. By March 28, she had bought her business back, and instead of resuming her role as sole leader, she made a strategic move—appointing tech entrepreneur Lauren Malin Melian as the new president of Slutty Vegan.

The Entrepreneur’s Challenge: Building vs. Managing

Cole’s story highlights a key business lesson: many entrepreneurs excel at starting businesses, but scaling them requires a different skill set. Founders are often visionaries, risk-takers, and disruptors, but running operations, managing finances, and handling logistics can be overwhelming.

Why Hiring a CEO Makes Sense

Cole realized that bringing in a CEO could help her achieve sustained growth. This is a lesson echoed by many successful founders, including:

  • Howard Schultz (Starbucks) – Built the brand but appointed CEOs at various growth stages.
  • Sara Blakely (Spanx) – Transitioned leadership after her company reached a global scale.
  • Larry Page & Sergey Brin (Google) – Brought in Eric Schmidt to ensure structured growth.

Entrepreneurs must ask themselves: Are you the best person to run your business at scale, or do you need a CEO who can manage growth, leadership, and strategy?

Stanley 1913: How a Viral Brand Stays Relevant

Another major business discussion in this episode focused on Stanley 1913, the company behind the viral Stanley Cup tumblers. Known for its durable 40-ounce tumblers, the brand skyrocketed in popularity, particularly among moms in Utah.

But as Ramon points out, one viral hit doesn’t guarantee long-term success. Stanley’s leadership knew that expanding beyond their initial success required strategic planning.

Stanley’s Growth Strategy

Stanley implemented several key business strategies to sustain momentum:

  1. Leverage Unexpected Trends – Rather than dismissing the viral surge as temporary, Stanley doubled down on marketing to its newfound audience.
  2. Evolve with Market Phases – The company shifted focus from blue-collar workers to outdoor enthusiasts and everyday users.
  3. Diversify Offerings – Moving beyond tumblers, Stanley expanded into coffee cups, cocktail shakers, and protein bottles.
  4. Go Global at the Right Time – Recognizing demand outside the U.S., Stanley began expanding into Europe and Asia.
  5. Invest in Leadership – Bringing in experienced executives from Adidas and Allbirds to help drive growth.
  6. Partner with Influencers – Collaborating with figures like Lionel Messi to expand brand credibility.
  7. Prepare for Backlash – Addressing environmental concerns and safety issues to manage reputation risks.

Why Viral Success Requires Long-Term Strategy

Stanley’s leadership understands that while viral products can create massive short-term revenue, maintaining success requires continuous innovation. The company is now focusing on product diversification, international expansion, and strategic branding efforts to sustain growth.

Entrepreneurs should take note: If your business experiences a viral boom, what’s your plan for the next phase?

Key Takeaways for Entrepreneurs

Both Pinky Cole and Stanley 1913 highlight crucial lessons for business owners at any stage:

  • Founders must recognize their strengths. If you’re better at vision and creativity than operations and logistics, hiring a CEO may be the best decision.
  • Scaling requires reinvention. Whether it’s recovering from setbacks or evolving beyond a viral hit, businesses must continuously adapt.
  • Strategic leadership matters. Companies like Google, Spanx, and Stanley 1913 have all relied on experienced executives to transition into new phases of success.

Final Thought: Entrepreneurship is a Long Game

Pinky Cole’s resilience and Stanley’s ability to reinvent their brand prove one thing—entrepreneurship isn’t a one-time victory; it’s a long-term strategy.

So ask yourself: Are you setting up your business for sustainable success? Do you need to rethink your leadership structure or expand beyond a single product success?

Let’s keep learning from these powerful examples. Want more insights? Subscribe at ZoneofGenius.com for the latest entrepreneurial strategies!

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