OhHello with Jeremy Bloom

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 

Brad Jaehn, a 30-year digital and tech leader (Orbitz, GoGo, McDonald’s), reflects on being fired over mentoring and why human connection matters in leadership. He discusses organizational investment in people, the role of AI alongside human guidance, and the challenges and skills needed to lead distributed teams. Short, candid, and thought-provoking.

Jackelyn 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

Jason 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.

Jay Wolff, digital advertising leader and president of 212 NYC who champions mentorship and human-centered management. He discusses leading by connecting people. He describes learning to let go and empower teams. He shares how genuine, reciprocal networking and small gestures build lasting relationships. He urges involvement in local communities to grow and give back.

Ajinkya “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.

Jeremy Bloom and Scott Hess, Chief Marketing Officer of Starcom and Chief Marketing Officer of Publicis Media, discuss the significance of the Chicago Advertising Federation's Career Day, the importance of mentorship and networking in the advertising industry, and personal experiences that shaped their careers. They reflect on the joy of working in advertising and the opportunities available for young professionals entering the field. Takeaways Scott Hess is the Chief Work Officer of Publicis Media. The Chicago Advertising Federation's Career Day is crucial for networking. Mentorship can significantly impact career paths in advertising. Career Day demystifies the advertising industry for young people. Networking events provide access to industry leaders and opportunities. Scott's son found joy in advertising after initially pursuing engineering. The advertising industry offers diverse career paths and opportunities. Personal connections can lead to job opportunities and mentorship. The excitement of young professionals can reinvigorate seasoned veterans. Chicago's winter can be a downside, but the city has much to offer. Chapters 00:00 Introduction and Background 02:43 The Importance of Career Day 05:37 Mentorship and Networking in Advertising 08:50 Personal Experiences and Career Paths 11:38 The Joy of Working in Advertising 14:37 Conclusion and Upcoming Events

Heather Macaulay, President of MadConnect, joins Jeremy Bloom to talk about simplifying complexity in ad tech, making career decisions across different life seasons, and why the best leaders focus on problem solving, listening, and connecting people behind the scenes. Takeaways Heather Macaulay is the president of MadConnect. MadConnect automates connectivity in the advertising ecosystem. Presenting a clear message is crucial for success. Entrepreneurship requires taking risks and trusting oneself. Sales should focus on problem-solving rather than transactions. Mentorship plays a vital role in career development. Balancing career and family requires conscious decisions. Building a personal brand involves genuine connections. Listening is key to effective mentorship. Your network is essential for success in any industry. Chapters 00:00 Introduction to Heather Macaulay 02:41 Understanding MadConnect and Its Role 05:52 The Journey to Entrepreneurship 08:33 Sales Strategies and Problem Solving 11:38 Mentorship and Guidance 14:37 Balancing Career and Family Life 17:20 Building Trust and Personal Brand 20:39 Parting Words and Industry Insights

Jeremy Bloom and Lida Tohidi explore the intersection of product management and coaching, discussing the importance of balancing work and personal well-being. Lida shares her journey from being a med school dropout to a successful product manager and coach, emphasizing the need to recognize burnout and set boundaries. They delve into the fears that many professionals face in the tech industry and the significance of human connection in overcoming these challenges. Lida also highlights effective mentorship strategies and the lessons she has learned from her own mentors, concluding with a call to action for listeners to pause and reflect on their own lives. Takeaways Lida transitioned from med school to tech, finding her niche in product management. Balancing technical skills with coaching is essential for success. Burnout is a common issue in tech, and setting boundaries is crucial. Many professionals feel an impending sense of doom due to an unsustainable work pace. Intentionally slowing down can lead to better outcomes. Effective mentorship involves accountability and co-creating goals. Lida emphasizes the importance of human connection in tech roles. Taking breaks and resting is vital for long-term productivity. Self-reflection and pausing can enhance personal well-being. Trusting your team is essential for effective leadership. Chapters 00:00 Introduction and Background 02:37 Balancing Product Management and Coaching 05:17 Recognizing Burnout and Setting Boundaries 07:58 Traits of Successful Leaders 11:07 Effective Mentorship and Guidance 13:41 Lessons from Mentors and Personal Growth 16:32 Final Thoughts and Advice

In this engaging conversation, siblings Hannah Bloom and Walter Bloom, along with their father Jeremy Bloom, explore various themes such as personal interests, mentorship, aspirations, and the importance of being true to oneself. They share insights on how to navigate challenges, the significance of role models, and the value of pursuing one's passions. The discussion also touches on the impact of peer pressure and the importance of kindness and support in relationships. Ultimately, they emphasize living life to the fullest and staying authentic in a world that often encourages conformity. Takeaways Hannah and Walter express their interests in acting, DJing, and biking. Mentorship plays a crucial role in their lives, with family and teachers as key figures. Living life to the fullest and seizing opportunities is essential. It's important to pursue what makes you happy, regardless of others' opinions. Being yourself means being a leader and not a follower. Peer pressure can be challenging, but individuality is important. Advice for adults includes being supportive and understanding in the workplace. Legacy is about being remembered as a good person and making a positive impact. Both siblings aspire to help others and support causes they believe in. The conversation highlights the importance of family support and open communication. Chapters 00:00 Introduction and Meet Hannah and Walter 02:10 What Dad Does for Work 03:20 Personifying Oh, Hello 04:00 Mentors and Role Models 05:30 Advice for the World 07:00 Handling Peer Pressure and Confidence 09:20 Asking for Help and Learning from Others 13:10 What They Want to Be When They Grow Up 17:10 Starting a Business and Giving Back 19:10 Finding What You’re Good At 20:25 What It Means to Be Yourself 22:00 Teasing, Bullying, and Respect 24:50 Advice for Grownups at Work 27:10 Advice to Their Future Selves 28:40 Legacy and Impact 30:20 Questions for Dad 36:30 Final Words of Wisdom