OhHello with Jeremy Bloom

Hosted by Jeremy Bloom

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145

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Oct 2026

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About the show

OhHello with Jeremy Bloom is a no-BS career mentorship and leadership podcast for people who want to get better at what they do — and enjoy the process. Hosted by Jeremy Bloom, founder of OhHello.ai and co-founder of Marketecture Media, the show features unfiltered conversations with executives, founders, and creatives who have learned to navigate change, uncertainty, and reinvention in their careers. Each episode offers a look into the real stories behind the titles — how leaders overcome burnout, how they stay human while managing growth, and how vulnerability and curiosity shape modern leadership. Whether you’re leading a team, scaling a startup, or figuring out your next move, OhHello gives you actionable insights from people who’ve been there. No fluff. No jargon. Just human connection, better questions, and stories that remind us how mentorship — and honest conversation — can change everything. Why listen + watch: Learn from today’s most empathetic and high-impact leaders. Discover practical frameworks for growth, decision-making, and resilience. Hear what modern mentorship looks like in a world of AI, remote work, and constant change.

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60 recent

October 27, 202622 min

OhHello Ep. 142: Kate Herbert on Leadership, Executive Coaching & Career Growth

Jeremy Bloom sits down with Kate Herbert, Executive Coach, Leadership Coach, and former ad tech executive, to explore her journey through DoubleClick, Google, MoPub, and Oracle. Kate shares valuable lessons on leadership, mentorship, career development, and building lasting professional relationships. From navigating global teams to advising AI startups, she explains why great leaders ask powerful questions, build trust, and empower others to succeed. Takeaways - Leadership Is About Asking the Right Questions: Great leaders empower teams through curiosity, collaboration, and shared vision rather than having all the answers. - Build Relationships That Last: Strong professional networks and trusted mentors can open doors and create opportunities throughout your career. - Take Ownership of Your Career: Setting boundaries, recognizing blind spots, and making intentional decisions are essential for professional growth. - Mentorship Accelerates Success: Honest feedback, trust, and executive coaching help professionals become more confident and effective leaders. - Embrace New Opportunities: Career growth often comes from taking risks, exploring unfamiliar roles, and learning from every experience. - AI Is Transforming Advertising: Emerging AI technologies are reshaping ad tech, but human creativity, strategic thinking, and decision-making remain essential. Chapters 00:00 Introduction to Kate Herbert and OhHello 00:31 Kate Herbert's Background in Ad Tech and Coaching 01:29 Global Leadership Experience at DoubleClick and Google 03:27 From Solutions Consulting to Leadership 05:21 Building MoPub and Growing Professional Networks 07:52 The Mentors Who Shaped Kate's Career 09:34 Trust, Honest Feedback, and Executive Coaching 11:32 Leadership Lessons from Oracle 12:54 The Journey from Ad Tech Executive to Coach 13:31 Redefining Leadership and Empowering Teams 15:50 Advising Startups and Supporting Founders 18:11 AI Innovation and Emerging Advertising Technologies 19:50 The Future of AI Agents in Advertising 20:36 Career Advice and Taking the Next Step 21:54 Closing Remarks

October 20, 202632 min

Episode 141: Ian Schafer on Building with Issa Rae, the Creator Economy, and the Power of Mentorship

Jeremy Bloom sits down with Ian Schafer, co-founder of Ensemble, to explore entrepreneurship, leadership, mentorship, and the future of the creator economy. Ian shares his journey from founding Deep Focus to building entertainment ventures with Issa Rae, the rise of creator-led content, and why meaningful relationships are essential to long-term success. Discover valuable lessons on innovation, audience-first storytelling, networking, and the power of helping others succeed. Takeaways - Ian Schafer shares his journey from founding Deep Focus to building creator-led entertainment businesses. - The creator economy is reshaping how brands, audiences, and entertainment companies connect. - Building successful content starts with understanding audiences and prioritizing authentic storytelling. - Strong mentors and professional relationships help entrepreneurs navigate challenges and opportunities. - Generosity, meaningful connections, and helping others are essential to lasting success. chapters 00:00 Introduction to Ian Schafer 01:14 Ian's Career in Media and Advertising 02:18 Founding Deep Focus and Reinventing Digital Advertising 04:43 Building HoRaye Media and Ensemble with Issa Rae 07:34 The Rise of the Creator Economy 09:42 Issa Rae's Journey from YouTube to Hollywood 11:09 Audience-First Storytelling and Brand Partnerships 14:45 The Power of Access and Early Mentorship 19:00 Challenging Industry Norms and Learning from Mentors 24:33 Post Credits: The Future of Hollywood and Creators 27:15 Career Advice, Networking, and Giving Back 30:36 Why Generosity and Mentorship Matter 31:42 Closing Remarks

October 13, 202623 min

Episode 140: Career Confidence, Leadership & Defining Success on Your Own Terms

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

October 6, 202642 min

OhHello Ep. 103: Finding Your Path: A Journey of Self-Discovery with Jason DaWayne Smith

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. Takeaways The importance of authenticity in personal and professional life. Living a life of service can lead to fulfillment. A mindset of abundance can enhance one's zest for life. Overcoming challenges can lead to personal growth and self-discovery. Community support is vital for achieving personal and professional goals. Mentorship should involve challenging perspectives, not just comfort. Daring to be dull means starting without the pressure of perfection. Access to opportunities can change the trajectory of one's career. Disrupting your own narrative is essential for growth. Building genuine relationships is key to success. Chapters 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

September 29, 202638 min

OhHello Ep 139: Leadership, Discipline and Finding Your Purpose with Marc Grabowski

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

September 15, 202632 min

OhHello Ep. 138: Alex Sherman on Leadership, Mentorship & Building Bluefish

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 Build teams around trust, intelligence, and kindness. Reputation and relationships compound throughout your career. Mentorship remains valuable at every career stage. Great leaders focus on outcomes without micromanaging. High performance doesn’t require toxic startup culture. 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

September 8, 202627 min

OhHello Ep. 137 Building Brands That Feel Human with Josh Rangel of Ogilvy

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

September 1, 202634 min

OhHello Ep. 136 Evan Shapiro on Personal Branding, Data & the Future of Media

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 Build your brand by consistently delivering value. Great decisions start with healthy data. Mobile is now the center of media consumption. Stay curious and "wake up stupid" every day. Success comes from consistent daily habits. 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

August 25, 202631 min

OhHello Ep. 106: Empathy in Leadership: The Sightly Approach

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 Kara Grenier emphasizes the importance of culture in attracting talent. Adam Katz believes in leading with empathy and respect for employees. The relationship between the CEO and Chief People Officer is crucial for company culture. A distributed workforce requires leaders who are confident and secure in their roles. Mentorship is vital for personal and professional growth. Creating a culture of continuous learning is essential for employee retention. Asking for help should come from a place of security, not insecurity. Community and collaboration enhance workplace dynamics. Diverse voices in leadership lead to better decision-making. Both leaders value the role of mentors in their careers. Chapters00:00 Introduction to Sightly and Its Leaders02:39 The Dynamic Duo: CEO and Chief People Officer05:23 Building a Distributed Workforce08:49 Leadership and Employee Well-being11:30 Cultivating Growth and Development14:50 The Importance of Asking for Help17:27 Mentorship and Community Building20:29 Personal Growth and Learning23:32 Closing Thoughts and Reflections

August 11, 202624 min

OhHello Ep. 135 Nirit Cohen on the Future of Work, AI & Leadership

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 Nirit Cohen shares her 30-year journey at Intel and how it led her to become a leading voice on the future of work. Why work should be integrated with life instead of balanced against it. The concept of the "future of less work" and focusing on what truly matters. How AI is transforming expertise, creativity, and professional value. Why storytelling remains a uniquely human advantage in the age of AI. Practical advice for experienced professionals on collaborating effectively with AI. Why younger professionals should learn from people, not just AI tools. Leadership lessons for managing hybrid and distributed teams. The career-changing power of mentorship, sponsorship, and unexpected opportunities. Why building a strategic network creates long-term career growth. 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

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