Let's Talk Business, Podcast

Accountability, Inspiration, Passion, and Feedback: Learning About Leadership with Chaim Berkovic

By , April 8, 2024

Growing up in Williamsburg, Chaim Berkovic learned the importance of having a vision; years later, as the president and founder of Skyscraper Insurance, he was able to actualize that vision, even though the ways to achieve it were sometimes unclear. In this fascinating conversation, Meny asks Chaim about some of the methods he used to create and grow his business, as well as his strategies for being an effective leader. Listen in as they talk about transmitting passion to employees, how to maintain “brutal accountability” while also creating a positive company culture, the role of inspiration in leadership, what can be learned from failure, why feedback is indispensable, and more.

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Accountability, Inspiration, Passion, and Feedback: Learning About Leadership with Chaim Berkovic

Key Highlights:

[00:01 – 05:00] The Visionary’s Journey

  • Chaim’s transition from early failures to founding Skyscraper Insurance
  • The importance of learning from mistakes and taking calculated risks
  • How personal challenges fueled Chaim’s entrepreneurial spirit

[05:01 – 15:00] Risk Management and Client Trust

  • How Skyscraper Insurance approaches risk management differently
  • The significance of understanding client needs and building trust
  • Insights into the complexities of the insurance industry

[15:01 – 25:00] Leadership Beyond the Boardroom

  • The role of inspirational leadership in building a successful team
  • Balancing company culture with high performance and accountability
  • Strategies for nurturing a positive, growth-oriented workplace

[25:01 – 35:00] Mastering Growth and Scalability

  • Chaim’s perspective on business growth and strategic acquisitions
  • The impact of community and relationship-building in expansion
  • Learning from industry shifts and adapting for scalability

[35:01 – 46:08] The Mastermind Effect

  • The benefits of participating in mastermind groups for business leaders
  • How shared knowledge and accountability drive success
  • Chaim’s personal experiences and gains from mastermind involvement


Want to connect with Chaim? Follow him on LinkedIn. Head to Skyscraper Insurance for a better tomorrow!


Key Quotes:

“The biggest risk takers are the ones that know back end the calculated risks behind it.” – Chaim Berkovic

“If your circle doesn’t inspire you, you’re in the wrong circle.” – Chaim Berkowick


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About Chaim Berkovic

Chaim Berkovic is the founder and president of Skyscraper Insurance. A visionary in the insurance arena, Chaim has extensive management expertise and has developed keen insight into the industry. Chaim is known for identifying opportunities in the insurance marketplace to create products, services and startup companies that address market opportunities, with a keen focus on high-risk populations which have been historically underserved.

Meny Hoffman

Meny Hoffman is the Chief Executive Officer of Ptex Group, an Inc. 500/5000-ranked marketing and business services firm headquartered in Brooklyn, NY.

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