"The Art of Scaling: Leadership, Cash Flow, and Team" with Maria Kelly

Hello everyone! Today we are excited to share an enlightening conversation with Maria Kelly. She has over 20 years of experience in corporate life at Sotheby’s, the renowned art auction house, where Maria managed sales teams and established new global divisions in cities like New York and London, significantly increasing revenue and market share. In 2020, she moved to Spain and founded her own business, 'Ask Maria,' which provides leadership coaching and training to companies, including small businesses.

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1. From Corporate Executive to Entrepreneur

• Maria spent over 20 years at Sotheby’s, managing global sales teams and establishing new divisions.
• After working in New York and London, she realized her life wasn’t aligning with her personal fulfillment.
• Maria admitted she never loved living in London as much as New York, but her dissatisfaction went beyond location.
• She took a break to reevaluate and concluded she didn’t want another corporate job.
• Maria and her husband made the bold decision to move to Barcelona, Spain, to start a new business from scratch.
• At 48, she recognized it was the right time to take the leap, knowing she might not get another chance.
• The decision was carefully considered—Maria made lists, weighed options, and approached it with a mindset of flexibility.
• The move to entrepreneurship wasn’t just about lifestyle change; it was a purposeful choice to build something meaningful in a place they loved.

2. Entrepreneurship Isn’t All Rainbows and Ponies

• Maria is refreshingly honest about the challenges of starting a business, avoiding the glorified "hustle" many entrepreneurs promote.
• Transitioning from managing global teams to running a one-woman operation, she handled everything from client acquisition to admin tasks.
• The learning curve was steep, and just two months into her new business, the COVID-19 pandemic hit, adding to the difficulties.
• On a personal level, Maria began going through menopause, which impacted her energy and focus.
• She candidly shared a mistake caused by brain fog, where she undercharged a client for an entire year’s contract—an experience that taught her to double-check her work.
• Despite the challenges, Maria found ways to be more efficient, embraced automation, and sought advice from experienced entrepreneurs.
• She stayed connected by joining local and online entrepreneurial communities, leveraging their support to continue growing her business.
  
  

3. Adjusting Your Business Approach and Client Focus

• Maria initially aimed to focus on helping startups and small businesses but quickly realized many lacked both the awareness of what guidance they needed and the budget to afford it.
• This forced her to adjust her approach without abandoning her vision.
• She started forming connections with investors who were willing to hire her on behalf of startups that needed leadership training but didn’t realize it yet.
• This pivot allowed Maria to continue providing meaningful coaching to businesses without struggling with constant funding issues.

4. Knowing Your Strengths, Finding Your Niche

• Three years into her business, Maria finds immense satisfaction working with small businesses and SMEs at critical growth stages.
• These businesses are expanding but often lack the leadership expertise needed to scale effectively.
• Maria’s 20+ years of corporate experience, including her time at Sotheby’s, provide invaluable guidance for founders concerned about maintaining company culture or navigating operational scaling.
• Her international business expertise offers a rare perspective, helping small business owners avoid common pitfalls in leadership structure and growth strategies.
• Maria’s approach ensures businesses can grow sustainably without facing significant issues that could hinder their success.

5. Critical Lessons for Business Owners

• Maria emphasizes that entrepreneurs should avoid waiting for everything to be perfect before taking action. Waiting wastes valuable time.
• Start where you are and adapt as you go; the business you envision will likely evolve as you gain experience and respond to market needs.
• Flexibility and a willingness to pivot are crucial to success, rather than sticking rigidly to one idea.
• Communication is another key focus, especially for businesses about to scale. Miscommunication can disrupt momentum, particularly when new teams or divisions are introduced.
• Maria highlights the importance of leadership alignment, as strong collaboration at the top ensures the entire team follows suit and avoids resistance.

6. What You Can Learn From Maria's Journey

• Start before you’re fully ready: Don’t wait until everything is perfect, because it never will be. Take the leap and adjust course as you learn.
• Be adaptable: Your business may evolve in unexpected ways. Be willing to shift direction based on what your clients and the market dictate.
• Focus on communication: Strong internal communication is critical, especially during periods of growth. It’s essential to keep your team aligned and motivated.
• Seek help when you need it: Whether that’s through mentors, coaches, or consultants like Maria, external insights can help you avoid common pitfalls.
• Build win-win relationships with investors: Educate investors on how you can help their portfolio companies grow sustainably. This not only helps startups thrive but also builds lasting client relationships for you.

Maria Kelly’s transition from corporate leader at Sotheby’s to entrepreneur has been full of challenges and growth. Her story offers real-world lessons for business owners at all stages. Whether you’re scaling a small business, navigating internal challenges, or trying to carve out a niche, Maria’s advice is clear: take action, be willing to pivot, and always keep learning from your experiences.