Podcast
OhHello with Jeremy Bloom
Hosted by Jeremy Bloom · EN
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.
20episodes
Episodes
Newest firstAll episodes
OhHello Ep.125 Carrie Kramer on vulnerability, growth, and knowing when to move forward with clarity
2w ago00:24:03Tap to summarizeCarrie 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
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OhHello Ep.124 Jes Santoro on Leadership, Mentorship, and the Human Side of Revenue Growth
3w ago00:28:10Tap to summarizeJes 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.
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OhHello Ep.123 The “CMO Whisperer” Reveals What Marketing Leaders Won’t Say Publicly with Steve Olenski
4w ago00:22:51Tap to summarizeSteve 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
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OhHello Ep. 122 Why Salespeople Burn Out And How to Actually Succeed with Dr. Deepak Bhootra
Apr 2100:18:12Tap to summarizeDr. 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
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OhHello Ep. 121 From Finance to Community Builder: Amelia Tran on Grit, Mentorship & Career Growth
Apr 1400:22:56Tap to summarizeAmelia 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
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OhHello Ep. 120 Brad Jaehn on Mentorship, Leadership, and the Future of Work
Mar 3100:16:07Tap to summarizeBrad 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
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OhHello Ep. 119 On Confidence, Career Pivots & Choosing Movement Over Comfort
Mar 2400:22:30Tap to summarizeJackelyn Keller, a marketing leader, strategist, and educator—and Founder of Jackwell Partners, a marketing consultancy—shares her journey from sales assistant to CMO and what it taught her about trusting your instincts. Known for translating complex technology into clear, actionable strategy, she explores career pivots, building confidence without certainty, and why mentorship and relationships often matter more than resumes. Takeaways Confidence isn’t about having all the answers–it’s trusting that you’ll figure it out. Career growth comes from trying new things rather than staying where you’re comfortable. Relationships often matter more than what’s on your resume. Mentorship works best when it’s rooted in empathy and active listening. Taking care of yourself shapes how you show up at work and in life. Chapters 00:00 Introduction to Jackelyn Keller and her background 02:30 Building a career across marketing, teaching, and entrepreneurship 06:10 Knowing when to push through versus when to pivot 07:45 Taking risks before feeling ready 10:00 Redefining confidence as self-trust 11:40 Overcoming fear of public speaking through teaching 14:15 Mentors who shaped her career 16:20 What makes a great mentor 17:20 Why leaders struggle to ask for help 18:20 Managing self-doubt and personal pressure 20:00 The importance of outside perspectives 22:20 Advice for early-career professionals 23:15 The value of mentorship and community
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OhHello Ep. 118 Jason Loehr, Data & AI Advisor: How Empathy, Curiosity & Data Drive Better Leadership
Mar 1700:17:16Tap to summarizeJason Loehr, a data and AI advisor with experience across companies like Camping World and Brown-Forman, joins Jeremy Bloom to discuss how leaders can combine technology, empathy, and critical thinking to navigate digital transformation. They explore Jason’s early experience launching one of the first online catalogs, how consumer-first thinking shaped his career, and why AI should empower people rather than replace them. Jason also shares insights on leadership, curiosity, and how organizations can use data and learning agendas to make better decisions. Takeaways Early digital innovation showed Jason that understanding customer lifetime value can reshape how companies view new technology. Successful digital transformation happens when organizations prioritize consumer experience over internal convenience. AI should free up human time for deeper critical thinking rather than replace human roles. Empathy and creative friction are essential for solving complex problems and building better ideas. Organizations make better decisions when they focus on the questions they need answered before gathering data. Democratizing data helps teams collaborate and solve problems faster across the organization. Leaders should automate predictable work, elevate human judgment, and optimize decision velocity. Technology itself is not the disruptor but the tool that enables meaningful disruption. Chapters 00:00 Jeremy welcomes Jason and introduces his background in digital transformation and marketing. 01:00 Jason shares his career journey from early e-commerce to working with major global brands. 03:30 Why consumer-centric thinking should guide technology and digital decisions. 05:30 Leadership traits, including curiosity, relationship building, and humility. 08:30 How AI and empathy work together in the future of work. 10:20 Using data and learning agendas to improve decision making. 13:00 A leadership framework automates predictable tasks, elevates human insight, and optimizes velocity. 14:00 The mentors and relationships that shaped Jason’s career. 16:00 Why leaders must stay intentional when adopting new technologies.
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OhHello Ep. 117 From Hustle to Human-Centered Leadership: Jay Wolff on Letting Go and Lifting Others
Mar 300:24:34Tap to summarizeIn this engaging conversation, Jeremy Bloom and Jay Wolff explore the intricacies of leadership, mentorship, and the importance of human connection in the digital advertising industry. Jay shares his journey from the early days of digital advertising to his current role, emphasizing the significance of empowering others and building meaningful relationships. The discussion highlights the value of networking, the role of mentorship, and practical advice for motivating teams and fostering a supportive work environment. Takeaways Leadership is about connecting people and empowering them. The journey to leadership involves learning through experience. Mentorship can come from various sources, including family and colleagues. Networking should be genuine and reciprocal, not transactional. Small gestures can have a significant impact on relationships. Understanding individual motivations is key to effective leadership. Creating a supportive environment fosters psychological safety. Involvement in local organizations can enhance career growth. Building a personal brand is essential in today's professional landscape. Empowering others leads to a more successful and cohesive team. Chapters 00:00 Introduction and Background 02:42 Defining Leadership and Team Building 05:40 The Journey to Leadership 08:41 Mentorship and Influences 11:44 The Importance of Networking 14:21 Motivating and Empowering Teams 17:31 Final Thoughts and Advice
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OhHello Ep. 116 Ajinkya “Jinx” Joglekar, ex-CMO Dish & Sling, on mentorship and curiosity
Feb 1000:25:12Tap to summarizeAjinkya “Jinx” Joglekar joins Jeremy Bloom to share what he learned leading marketing at Dish and Sling, why he decided to take the leap into consulting after 20+ years in corporate, and how curiosity became the skill that helped him “punch above his weight” early in his career. They also dig into what real mentorship looks like, how leaders can build a culture of learning across teams, and why great advertising is not just creative and media but also the sales experience. Takeaways Your corporate career can be the venture capital that funds your future risk-taking. Curiosity lets you lead and influence even before you have a title or direct reports. Great advertising only works when creative, media, and the sales experience are connected. Leaders build learning cultures by meeting every level of the team and making collaboration unavoidable. Mentorship programs work best when they are supported from the top but driven organically from the ground. Chapters 00:00 Jinx introduces himself and his background leading marketing at Dish and Sling. 03:05 Why he left the CMO seat to bet on himself and start consulting. 06:40 The mentor who gave him his first real marketing start and taught him scrappy fundamentals. 12:10 The moment he realized curiosity is a career advantage that helps you punch above your weight. 14:40 How to build a culture of learning through one-on-ones and cross-team collaboration. 18:10 Advice for emerging marketers and sellers: don’t stay in your lane and use your network. 20:05 How organizations can create mentorship programs that work without feeling forced.
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