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Jeremy Bloom sits down with Kevin Kowalick, Professor & Executive Coach, Amy Chou, Former TikTok Leader & Executive Coach, and Stacy Bohrer, SVP at OpenX, for a candid conversation about career pivots, confidence, leadership, and personal growth. They share lessons on navigating major career decisions, overcoming self-doubt, building an authentic leadership style, advocating for yourself, and defining success on your own terms.
Takeaways:
- Define success on your own terms.
- Confidence grows through action and practice.
- Great leadership comes in different styles.
- Self-advocacy is essential for career growth.
- Career pivots require courage and preparation.
Chapters:
00:00 Welcome and Introducing the OhHello Mentor Panel
01:38 Meet Kevin, Amy, and Stacy
03:14 Career Changes, Risk, and Knowing When to Move On
04:25 Planning for a Major Career Pivot
06:15 Amy on Redefining Personal Success
09:21 What Confidence Really Looks Like
11:46 Leadership, Ego, and Making Decisions
13:14 Building Confidence Without Being the Loudest Voice
17:09 Different Styles of Effective Leadership
17:59 What Mentoring and Coaching Teach Leaders
20:18 Why Self-Advocacy Matters
21:25 Experience, Instincts, and Trusting Your Judgment
22:32 Closing Thoughts and Connecting With the OhHello Mentors
In this engaging conversation, Jeremy Bloom and Jason DaWayne Smith explore themes of friendship, authenticity, personal growth, and the importance of mentorship. They discuss the significance of living a life of service, the zest for life that comes from overcoming challenges, and the role of community in personal and professional development. Jason shares his experiences with climbing, building businesses, and the impact of mentors in his life, emphasizing the need for genuine connections and the courage to disrupt one's narrative for growth.
00:00 Introduction and Friendship Dynamics
02:44 The Importance of Authenticity and Leadership
05:46 Zest for Life and Personal Growth
08:36 The 29,029 Challenge: A Journey of Self-Discovery
11:31 Community and Mentorship: Building Connections
14:37 Chicago Brothers: Empowering Multicultural Men
21:55 Community Support and Professional Development
23:55 Building Businesses and Overcoming Fear
30:29 The Importance of Mentorship
39:44 Disrupting Your Narrative for Growth
Jeremy Bloom sits down with Marc Grabowski, Chief Operating Officer at Integral Ad Science, to reflect on more than 25 years in ad tech and the lessons that shaped his career. Marc shares his perspective on the responsibilities of CEOs and COOs, the importance of mentors and strong teams, and why leadership requires trust, communication, and understanding what motivates people. He also connects lessons from ultramarathons to career growth, explaining how discipline, preparation, and community contribute to long-term success. The conversation explores mentorship, becoming an expert in your field, curiosity as a leadership strength, and why finding purpose beyond titles and promotions can lead to a more meaningful career.
Takeaways
- Great leadership requires ownership and trust.
- Discipline creates opportunities for long-term growth.
- Strong leaders understand what motivates their teams.
- Becoming an expert can open new career opportunities.
- Purpose matters beyond titles and promotions.
Chapters
00:00 Introduction
01:51 Marc’s Ad Tech Career
03:19 CEO vs. COO Leadership
06:26 Mentors and Career Influences
09:39 Talent and Opportunity
10:26 Lessons from Ultramarathons
13:58 Common Leadership Mistakes
17:09 Leading Teams at Scale
19:16 Boss, Coach, and Mentor
23:02 Discipline and Career Growth
28:02 Becoming an Expert
29:25 Curiosity as a Superpower
32:07 The OhHello Mission
35:06 Finding Your Purpose
38:08 Closing
Alex Sherman, Co-Founder & CEO of Bluefish, joins Jeremy Bloom to discuss entrepreneurship, mentorship, leadership, AI startup culture, and why success doesn’t require sacrificing kindness or strong relationships.
Takeaways
Chapters
00:00 Meet Alex Sherman
01:17 Building Bluefish
05:21 Building With People You Trust
08:13 The Power of Mentorship
11:30 Reputation and Relationships
14:33 Building a “Smart and Kind” Culture
22:09 Evolving as a Leader
25:33 Advice for Young Founders
26:39 Toxic AI and Startup Culture
29:37 Winning Without Being a Jerk
31:36 Closing Thoughts
Josh Rangel, Senior Director of Social Strategy at Ogilvy, joins host Jeremy Bloom to discuss his journey from traditional PR to leading social strategy for some of the world’s most recognizable brands. Josh shares how authenticity, mentorship, calculated risks, and a people-first leadership style shaped his career. He also explains why brands should stop overengineering content and start communicating in ways that genuinely connect with their audiences.
Takeaways:
- How Josh transitioned from traditional PR to social media strategy
- Why developing an authentic professional voice can create new opportunities
- The mentors who helped shape Josh’s career and leadership approach
- Why brands often overthink and overproduce social content
- How Ogilvy refreshed Mastercard’s Priceless message for Gen Z
- Lessons Josh learned after being laid off following an 18-year tenure
- Why leaders should focus on what they can control and lead with empathy
Chapters:
00:00 Meet Josh Rangel of Ogilvy
02:12 From Traditional PR to Social Media
03:08 Launching Klondike on Twitter
04:44 Leading Social Strategy for Major Brands
05:51 How PR Shaped an Earned-First Mindset
07:23 Finding an Authentic Professional Voice
10:33 Mentors Who Shaped Josh’s Career
13:15 Leadership Through Confidence and Empathy
15:21 Why Brands Overcomplicate Social Content
18:29 Taking Creative Risks with Mastercard
21:44 Recovering and Rebuilding After a Layoff
24:53 Career and Leadership Advice
27:04 Final Thoughts and Closing
Evan Shapiro shares his journey from leading major media companies to becoming a successful creator and industry thought leader. Learn why personal branding, data-driven decision-making, and staying endlessly curious are essential for growth. Whether you're a marketer, founder, creator, or business leader, this conversation offers practical insights on leadership, the future of media, and how to stay ahead in a rapidly evolving industry.
Takeaways
Chapters
00:00 Introduction
00:22 Meet Evan Shapiro
03:38 From Executive to Creator
11:37 Personal Branding
19:09 Why Companies Struggle
23:34 The Power of Good Data
30:02 The Future of Media
31:25 Career Advice
36:11 Closing
In this engaging conversation, Jeremy Bloom hosts Kara Grenier, Chief People Officer, and Adam Katz, CEO of Sightly. They discuss the unique dynamics of their leadership roles, the importance of company culture, and the challenges of managing a distributed workforce. The conversation highlights the significance of mentorship, the need for continuous growth, and the value of community in the workplace. Both leaders share personal insights and experiences that shape their approach to leadership and employee development.
Takeaways
Chapters
00:00 Introduction to Sightly and Its Leaders
02:39 The Dynamic Duo: CEO and Chief People Officer
05:23 Building a Distributed Workforce
08:49 Leadership and Employee Well-being
11:30 Cultivating Growth and Development
14:50 The Importance of Asking for Help
17:27 Mentorship and Community Building
20:29 Personal Growth and Learning
23:32 Closing Thoughts and Reflections
Jeremy speaks with Nirit Cohen, former Intel executive and Forbes contributor, about how AI is reshaping careers, leadership, and workplace culture. They explore mentorship, hybrid work, storytelling, and why building a strong professional network remains one of the most valuable career investments.
Takeaways
Chapters
00:00 Introduction
00:19 Meet Nirit Cohen
00:53 30 Years at Intel & The Future of Work Journey
02:49 The Future of Less Work Explained
05:46 Why Work and Life Should Be Integrated
07:54 Career Lessons, Mentorship & Networking
10:15 From Finance to HR: A Career-Changing Opportunity
12:30 The Mentors Who Shaped Nirit's Career
15:12 Leadership in the Age of AI & Hybrid Work
16:36 How AI Is Changing Expertise and Human Value
18:56 Why Storytelling Still Matters More Than AI
19:59 Advice for Professionals Feeling Left Behind by AI
23:59 Building a Strategic Network for Career Growth
25:27 Final Thoughts & Closing
In this conversation, Andrew Yeung shares his journey from moving to New York during the pandemic to founding Fibe, a tech events business. He discusses the importance of community, mentorship, and the concept of the 'third door' in accessing opportunities. Andrew emphasizes the value of building supportive environments and encourages aspiring entrepreneurs to take action on their ideas.
Takeaways
Chapters
00:00 Introduction to Andrew Yeung
02:44 The Birth of Fibe and Early Challenges
05:34 Building Community and Connection
08:38 The Concept of the Third Door
11:46 The Role of Mentorship in Growth
14:33 Creating a Supportive Work Environment
17:28 Encouragement for Aspiring Entrepreneurs
20:32 Reflections on Career Choices
23:17 Final Thoughts and Advice
Jeremy Bloom speaks with Adam Kleinberg, CEO and Founder of Traction, about AI, leadership, Tai Chi principles, agency transformation, and why listening, adaptability, and continuous learning are essential for business success.
Takeaways
Chapters
00:00 Introduction
01:48 Meet Adam Kleinberg and Traction
03:33 Leadership lessons from Tai Chi
05:54 Reinventing the agency model with AI
08:52 Why companies must embrace AI
12:53 Building competitive advantage beyond AI tools
14:17 Mentorship and developing future leaders
18:15 Learning through failure and vulnerability
22:12 Final advice on embracing change
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