OhHello with Jeremy Bloom

Hosted by Jeremy Bloom

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133

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Jun 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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June 16, 202625 min

OhHello Ep. 129 The Career Advice Nobody Follows: Networking, Reinvention & Building Your Career Today

In Part 1 of this special mentor roundtable episode of OhHello.ai, Jeremy Bloom sits down with Marni Gordon, Career & Executive Coach and Founder of Midlife Marketers; Rose Steinberg, Founder and CEO of People Obsessed; and Marc Goldberg, Founder of Stages Collective. Together, they discuss the career advice people struggle to follow, why networking remains one of the most valuable professional assets, the importance of authentic relationships, and how careers have evolved from linear paths into dynamic journeys. From building meaningful connections and navigating career transitions to creating opportunities through trust and reputation, this conversation is packed with practical insights for professionals at every stage of their careers. Tune in for Part 1 of this candid discussion on mentorship, networking, and long-term career success. Takeaway Relationships create more career opportunities than resumes alone. Build your network before you need it. Networking is a long-term investment, not a transactional activity. Authenticity and curiosity strengthen professional relationships. Clear asks make it easier for others to help you. Careers today require adaptability and continuous reinvention. Internal networking is just as important as external networking. Your reputation is built in rooms you're not present in. Giving value first creates stronger professional connections. Career success is a journey, not a destination. Chapter 00:00 Introduction to the mentor roundtable featuring Marni, Rose, and Marc. 01:52 Why mentoring and giving back matter. 06:30 The best career advice people rarely follow. 06:45 Why building your network is essential. 08:12 Relationships matter more than most people realize. 10:14 Networking as a long-term investment. 11:28 Why careers are a journey, not a destination. 13:31 Common networking mistakes professionals make. 15:24 Building influence inside your organization. 17:31 What authentic professional relationships really mean. 20:56 How mentorship creates meaningful career impact. 21:15 What's changed about careers over the decades? 22:50 Reinvention and the rise of portfolio careers. 24:20 Why adaptability is the ultimate career skill.

June 9, 202618 min

OhHello Ep. 128: Abby Lovett on Trust, Reputation & Human-Centered Success

In this episode, Jeremy Bloom sits down with Abby Lovett, Founder of CTP and author of Superhuman: 8 SMALL Ways to be Super at What you Do and Human While You Do It. Abby shares the personal experiences that shaped her career, lessons from decades in PR and marketing leadership, and why trust, reputation, and human connection matter more than ever in an AI-driven world. From mentorship and authentic leadership to avoiding burnout and building credibility, this conversation offers practical wisdom for professionals navigating change and uncertainty. Takeaways Personal hardships can shape lifelong leadership values and career decisions. Success at work should never come at the expense of your health. Great leaders build trust by matching actions with their words. Recognition and appreciation are critical to employee engagement. Mentorship often comes through small, memorable moments. Burnout is frequently a sign of neglected personal well-being. AI provides the average, but humans create exceptional outcomes. Reputation remains one of the most valuable professional assets. Authentic communication strengthens leadership credibility. Taking care of each other is a leadership responsibility. Chapters 00:00 Jeremy welcomes Abby Lovett and introduces her background in PR, marketing, and mentorship. 01:00 Abby explains her firm's focus on credibility, trust, and reputation in the age of AI. 02:00 Abby discusses the human challenges professionals face alongside rapid technological change. 03:30 A personal story that shaped Abby's views on health, independence, and career success. 05:00 Abby shares why professionals shouldn't sacrifice basic well-being for performance. 07:20 Abby recalls a memorable leadership lesson from an early career experience. 11:10 The importance of action, accountability, and earning trust through follow-through. 13:00 Abby explains why honesty and responsiveness matter during uncertainty. 15:20 Many professionals struggle more with feeling undervalued than with the work itself. 16:20 Abby highlights the importance of self-care as the first step toward career clarity. 17:15 Why mentorship, relationships, and creativity remain irreplaceable. 18:00 Abby explains how people elevate ideas beyond what AI can generate. 18:45 Why reputation management is becoming even more critical in the AI era. 19:20 Abby's closing message on leadership, kindness, and community.

June 2, 202631 min

OhHello Ep. 127: Freestar CEO Kurt Donnell on Transparent Leadership and Building Human-First Teams

Freestar CEO Kurt Donnell joins Jeremy Bloom to discuss leadership, transparency, mentorship, and building resilient remote cultures in the age of AI. Kurt shares lessons from law firms, scaling teams, navigating uncertainty, and why curiosity is the ultimate leadership trait. From hiring decisions to AI adoption, this episode is packed with practical advice for modern leaders. Takeaways Transparency builds trust during uncertainty. Curiosity is the #1 trait Kurt hires for. Great leaders show up as real humans, flaws included. AI should remove the mundane so people can do meaningful work. Delaying tough people decisions hurts the entire team. Remote culture requires intentional connection points. Work-life balance is really work-life integration. Human-in-the-loop AI creates stronger adoption and better outcomes. Leaders should focus on clarity, not panic, during disruption. Mentorship creates impact for both mentor and mentee. Chapters 00:00 Intro to Kurt Donnell and Freestar 01:40 Why mentorship matters in leadership 02:30 Early career experiences that shaped Kurt’s leadership style 04:20 From law school to ad tech and Freestar 08:00 The hardest leadership lesson: making tough people decisions 11:00 Building trust during uncertainty and pressure 13:30 The mentor who shaped Kurt’s career most 15:00 Why work-life balance doesn’t exist 19:20 Building culture in a remote-first company 22:00 The qualities Kurt looks for in future leaders 24:40 Avoiding reactive leadership during AI disruption 28:15 Using AI without losing humanity 31:20 Final leadership advice: show up as a human being

May 26, 202631 min

OhHello Ep. 126: Victoria Usher on Leadership, Listening & High-Performance Tech PR Teams Strategies

Jeremy Bloom sits down with Victoria Usher, CEO of GingerMay, to discuss leadership, mentorship, communication, and the future of work in a rapidly evolving tech landscape. Victoria shares lessons from her unconventional career path spanning nursing, politics, and PR, along with insights on active listening, managing high-pressure situations, building empowered teams, and why face-to-face connection matters more than ever in an AI-driven world. Takeaways Great leadership comes from leading by example and staying involved. Active listening is one of the most underrated business skills. Strong teams are built through shared ownership and clear communication. Gut instinct is often pattern recognition built through experience. Face-to-face communication still matters deeply in a digital world. Mentorship should guide people toward finding their own answers. High-performing leaders stay calm and decisive during stressful moments. Honest communication creates trust and clarity within organizations. Businesses need clearer boundaries and expectations post-COVID. Emotional intelligence is critical for leadership and client relationships. Chapters 00:00 Intro and Jeremy welcomes Victoria Usher 01:42 Victoria’s journey as CEO of GingerMay 03:02 Why working in tech and innovation is exciting 04:03 What great leadership actually means 06:03 Balancing team input with gut instinct 09:15 Mentorship and learning from Michelle Norman 12:28 How nursing and politics shaped Victoria’s leadership style 14:47 The power of active listening and mentorship 19:05 What companies get wrong about enablement 22:18 Honest communication and leading with clarity 24:10 Why face-to-face interaction matters more than ever 27:15 Thriving under pressure and crisis leadership 30:45 Victoria’s final advice on listening and communication

May 19, 202624 min

OhHello Ep.125 Carrie Kramer on vulnerability, growth, and knowing when to move forward with clarity

Carrie Kramer joins Jeremy Bloom on the OhHello.ai pod to reflect on nearly nine years of building Future Proofed, a sales training and consulting company focused on the media and advertising industry. Carrie shares the realities of entrepreneurship, the emotional highs and lows of running a business, the importance of vulnerability in leadership, and the lessons she learned about partnership, values, and progress over perfection. Takeaways Building a business means becoming a salesperson, even if you’ve never sold before. Progress over perfection creates momentum and growth. Strong partnerships can be the most rewarding part of entrepreneurship. Vulnerability helped Carrie build trust and credibility online. Entrepreneurship is often glamorized, but it is not for everyone. Aligning personal and business values can strengthen partnerships. Repeat clients are a reflection of trust and strong collaboration. Leadership requires asking for help and letting go of perfectionism. Chapters 00:00 Carrie Kramer joins the OhHello.ai pod. 00:40 Carrie explains the evolution of Future Proofed. 03:17 How Carrie and Bo Davis decided to merge businesses. 04:47 The biggest misconceptions about starting a company. 06:52 Learning how to sell for the first time. 08:16 The highs of entrepreneurship and client wins. 10:10 The lowest lows of running a business. 11:50 Leadership lessons and asking for help. 13:24 Why progress over perfection matters. 13:56 Becoming more vulnerable on LinkedIn. 16:01 What Carrie is most proud of after nine years. 18:05 Advice for people thinking about starting a business. 21:04 The importance of personal and business values. 22:48 What Carrie is excited for next. 23:47 Final reflections on growth and entrepreneurship

May 12, 202628 min

OhHello Ep.124 Jes Santoro on Leadership, Mentorship, and the Human Side of Revenue Growth

Jes Santoro, Chief Revenue Officer at Cadent, joins Jeremy Bloom for a candid conversation about leadership, mentorship, emotional intelligence, and building high-performing teams in today’s fast-changing media and advertising landscape. Jes shares lessons from nearly three decades in the industry, why mentorship goes beyond training, and how great leaders balance data-driven decision making with empathy and authenticity. From career growth to accountability and company culture, this episode is packed with practical insights for modern leaders. Takeaways Mentorship is about support, inspiration, and helping people grow. Training develops skills, mentorship develops people. Great leaders balance emotional intelligence with data-driven decision-making. Career growth is rarely linear, and curiosity matters most. Accountability works best when built on trust and authenticity. Strong leadership starts with self-awareness and surrounding yourself with great people. People stay where they feel supported, valued, and connected to purpose. Positivity and calm leadership create stronger teams. Chapters 00:00 Jeremy welcomes Jes Santoro to the podcast. 01:24 Jes shares his career journey from agencies to CRO at Cadent. 03:42 How leadership changed after COVID and remote work. 06:28 Jes explains his three-step mentorship philosophy. 09:27 The mentor who shaped Jes’s leadership approach. 12:38 The difference between training and true mentorship. 14:37 Why emotional intelligence matters more than ever. 18:37 Self-awareness and building balanced leadership teams. 20:48 Career growth is not linear. 23:11 Creating accountability without fear-based leadership. 26:05 The importance of purpose, trust, and authenticity. 27:07 Final leadership advice and reflections on the industry.

May 5, 202622 min

OhHello Ep.123 The “CMO Whisperer” Reveals What Marketing Leaders Won’t Say Publicly with Steve Olenski

Steve Olenski, Founder of The CMO Whisperer Advisory, joins Jeremy Bloom to share what CMOs really think behind closed doors on credibility, AI pressure, career growth, and why marketing is still misunderstood in the C-suite. Takeaways CMOs struggle with credibility, not creativity Marketing is still undervalued in the C-suite AI is increasing pressure on marketing teams Alignment matters more than “great work.” Everyone thinks they understand marketing The best leaders embrace humility and empathy Authenticity is critical for long-term success Career growth comes from understanding business impact Relationships are built with genuine intent Paying it forward is a leadership responsibility Chapters 00:00 Intro & Meeting the “CMO Whisperer” 01:00 The Origin Story at Forbes 04:10 What CMOs Really Say Behind Closed Doors 05:45 What the Industry Gets Wrong About Marketing 07:00 Why CMOs Have the Shortest Tenure in the C-Suite 08:25 What Marketers and Executives Don’t Understand 09:15 “Everyone Thinks They Know Marketing” 11:00 Breaking Down Silos in the C-Suite 11:25 Building Real Relationships & Access 13:45 What Keeps CMOs Up at Night 15:20 Mentorship & Career Growth 17:25 Lessons from Great Leaders 19:25 Hiring Smart People & Letting Them Lead 21:10 Common Career Mistakes 23:50 Advice for Younger Professionals 24:30 Final Thoughts: The Human Side of Business

April 21, 202618 min

OhHello Ep. 122 Why Salespeople Burn Out And How to Actually Succeed with Dr. Deepak Bhootra

Dr. Deepak Bhootra, Chief Executive Officer of Jabulani Consulting, shares hard truths about sales and leadership, and why so many professionals struggle despite all the tools, training, and technology available today. Takeaways Sales success is less about adding skills and more about removing internal noise Mindset and attitude matter more than technique Many salespeople burn out not from failure, but from pressure and emotional strain Leaders often focus on metrics but ignore the human behind performance Coaching people is more effective than managing numbers Asking for help is difficult because of fear and perceived expectations Self-compassion is critical for long-term growth and resilience Career growth often requires having difficult, avoided conversations Chapters 00:00 Introduction to Dr. Deepak Bhootra 01:20 Background, purpose, and personal journey 03:14 What most people get wrong about sales 04:22 Why salespeople burn out early 05:45 The importance of leading indicators 06:06 Why salespeople get stuck 07:39 Why people struggle to ask for help 09:00 Burnout, mental health, and career shifts 11:01 The power of coaching and mentorship 11:53 What leaders get wrong in enablement 13:29 Coaching people vs managing numbers 13:53 Mentors that shaped Deepak’s career 16:33 Advice for those feeling stuck 18:27 Final thoughts and closing

April 14, 202622 min

OhHello Ep. 121 From Finance to Community Builder: Amelia Tran on Grit, Mentorship & Career Growth

Amelia Tran, General Manager at Marketecture Media and Founder, Asteria Collective, shares her journey from finance to marketing, the power of community, and how grit, mentorship, and relationships shaped her career. Discover actionable insights on networking, trust-building, and navigating career growth. Takeaways Relationships should be built before asking for help Action matters more than perfection Consistency builds trust over time Mentorship can completely change your career path Grit comes from turning nothing into something Growth requires stepping outside your comfort zone Feedback helps you understand your true strengths Strong relationships make asking for help easier Chapters 00:15 Introduction and welcome 00:52 Amelia shares who she is and what she does 01:22 Running communities and building opportunities 02:23 Starting in finance and career pivot 03:00 Mentorship that changed her path 04:25 Early career and agency experience 06:24 Where her grit comes from 10:25 Building trust and credibility 13:24 Realizing she could operate at a higher level 16:20 Key mentors and influence 17:58 How to ask for help effectively 20:12 How high performers handle friction 21:45 Advice for when you feel stuck 23:02 Final thoughts on relationships and growth

March 31, 202616 min

OhHello Ep. 120 Brad Jaehn on Mentorship, Leadership, and the Future of Work

Brad Jaehn shares his recent experience of being unexpectedly terminated over mentoring activities, explores the importance of human connection in leadership, and discusses the evolving role of AI and distributed teams in the workplace. Takeaways: The importance of mentorship and human connection in leadership The impact of organizational culture on employee development The role of AI in the future of work and human guidance Challenges and opportunities of distributed teams The significance of asking for help and mentorship in career growth Chapters 00:00 Introduction and Personal Connection 01:03 Brad Jaehn's Background and Career Highlights 02:05 Recent Termination Over Mentoring Activities 03:25 Reflections on the Impact of Mentoring and Giving Back 06:18 Organizational Investment in People and Leadership Development 07:56 The ROI of Employee Development and Mentorship 09:18 Mentoring as a Leadership Skill and Organizational Priority 09:52 Mentors Who Influenced Brad’s Career 11:20 The Role of Human Guidance in the Age of AI 13:34 Leading Distributed Teams and External Perspectives 15:02 The Future of Leadership and External Help 15:55 Advice for Aspiring Leaders and Mentorship 16:46 Closing Remarks and Final Thoughts