Empathy, Authenticity, and Positive Leadership: Amazing Journey from Attorney to Award-Winning Tech Innovator CEO | Rebecca Kacaba

Rebecca Kacaba, CEO of DealMaker, joins us on the Do Good to Lead Well podcast, sharing her captivating journey from a corporate attorney to a trailblazing entrepreneur reshaping North America's tech landscape. Her transition from law to entrepreneurship is driven by a desire to tackle the financing hurdles startup founders face. Rebecca's story is rich with lessons in empathy, resilience, and persistence, and how being mindful of our mindset can bring about transformative changes in our personal and professional lives.

We explore the traits essential for leadership today, particularly adaptability and grit, which are crucial in the ever-evolving tech world. Rebecca shares her insights on fostering adaptability within organizations through creative exercises and how maintaining a solid vision aligned with strategic goals is crucial for leaders. Balancing empathy with leadership responsibilities, she illustrates how fostering a culture of integrity and autonomy can democratize access to capital markets, showcasing DealMaker's mission.

Rebecca also candidly discusses overcoming imposter syndrome and embracing authenticity. She shares how being genuine reduces stress and builds meaningful connections. The episode wraps up with a thoughtful discussion on AI's impact on leadership, emphasizing the need for empathy and visionary leadership. Rebecca's insights provide a wealth of knowledge for aspiring leaders and entrepreneurs eager to make a significant impact beyond their balance sheet.

What You’ll Learn:

• The essential traits for modern leadership, such as adaptability and grit.

• Strategies for fostering adaptability within organizations.

• Overcoming imposter syndrome

• Embracing authenticity to build meaningful connections.

• The role of AI in the future of leadership and the enduring need for empathy and visionary leadership.

Podcast Timestamps:

(00:00) – The Journey from Attorney to Tech CEO

(10:50) - Building Adaptive Leadership with Grit

(26:30) – The Importance of Empathy and Integrity in Leadership

(38:43) - Embracing Authenticity and Overcoming Imposter Syndrome

(46:33) - Navigating AI and the Future of Leadership

More of Rebecca:

Rebecca Kacaba is the CEO and co-founder of DealMaker, a leading capital-raising platform revolutionizing the industry with cutting-edge technology. A former securities lawyer with over a decade of experience on Bay Street, she co-chaired the Toronto Venture Technology and Emerging Growth Companies group at a global law firm before launching DealMaker to streamline and modernize fundraising. Under her leadership, DealMaker has processed over $2 billion in transactions, earning recognition on Deloitte’s Canada Technology Fast 50 and North America’s Fast 500 lists, ranking alongside and even above industry giants like Zoom and DraftKings. Named one of North America’s most innovative lawyers by the Financial Times and one of Canada's most admired CEOs, Rebecca is dedicated to empowering founders to raise capital as easily as e-commerce, turning supporters into shareholders and reshaping the future of capital markets.

LinkedIn: https://www.linkedin.com/in/rebeccakacaba/

Mentions: 

DealMaker: https://www.dealmaker.tech/

Key Topics Discussed:

Positive Leadership, Entrepreneurship, Tech Innovation, Adaptability, Inspiration, Core Values, Artificial Intelligence, Financing, Startup Founders, Empathy, Resilience, Persistence, Grit, Capital Markets, Leading with Integrity, Authenticity, Dealing with Imposter Syndrome, Vulnerability, Mentorship, AI Strategy, Visionary Leadership, Personal Growth, CEO Success

More of Do Good to Lead Well:

Website: https://craigdowden.com/
LinkedIn: https://www.linkedin.com/in/craigdowden/