Let's Talk Business Episode 189: Accountability, Inspiration, Passion, and Feedback: Learning About Leadership with Chaim Berkovic

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.

[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