OhHello with Jeremy Bloom

Jeremy Bloom
  • 5.0 (11)
  • CAREERS
  • UPDATED SEMIWEEKLY

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.

  1. OCT 28

    OhHello Ep. 108: Mike Hauptman on Building Culture Without Walls and Leading Remote Teams

    In this episode, Jeremy Bloom sits down with Mike Hauptman, founder and CEO of AdLib, to explore how he’s redefining access to the programmatic advertising ecosystem and reshaping what leadership looks like in a remote-first world. Mike shares how AdLib evolved from a bootstrap experiment to a thriving global team of 20, serving independent agencies and brands with a unified platform that simplifies campaign execution across every DSP, SSP, and retail media network. The conversation dives deep into leadership, culture, mentorship, and resilience, as Mike reflects on lessons learned from building a company through industry disruption, maintaining connections across continents, and fostering trust in a world without office walls. Takeaways AdLib was built to solve a long-standing problem in ad tech: fragmented access across programmatic platforms. Mike and co-founder Dan Bogert turned a shared frustration into a company through persistence, patience, and self-funding. The collapse of MediaMath became a turning point that forced AdLib to evolve quickly and expand its reach. Leadership, for Mike, is about trust, not control, and giving people the space to deliver their best work. Running a remote team means finding new ways to create closeness and connection beyond office walls. A strong culture starts with empathy, small gestures of care, and genuine investment in people’s wellbeing. Transparency and vulnerability are core to how Mike communicates, both in success and in struggle. Mentorship and family values have shaped his belief in showing up, working hard, and staying grounded. Mike’s advice to future founders: take the leap, stay curious, and don’t let fear of failure hold you back. Chapters 00:00 Introductions and Mike’s Background 01:55 What AdLib Does and Its Purpose 03:22 The Journey from MediaMath to Founding AdLib 05:17 Early Iterations and Lessons from Bootstrapping 07:22 Evolving Leadership and Culture in a Remote World 09:47 Building Trust and Accountability Across Teams 11:23 Attracting Global Talent and Creating Belonging 13:59 Investing in People and Wellbeing 15:18 Fostering Vulnerability and Openness Remotely 17:17 Preparing for Growth and Staying Agile 19:22 Leading with Empathy Through Life’s Highs and Lows 20:14 Mentors, Work Ethic, and Life Lessons 22:35 Hard Lessons in Trust and Perseverance 24:01 Advice for Aspiring Entrepreneurs

    26 min

  2. OCT 14

    OhHello Ep. 107: From Advertising to Academia vs Adtech

    In this conversation, Jeremy Bloom and Kevin Kowalick discuss Kevin's significant career pivot from a successful ad tech career to academia and coaching. They explore the motivations behind such a change, the importance of mentorship, and the challenges faced by emerging leaders. Kevin shares personal anecdotes about his journey, the impact of coaching on individuals feeling stuck in their careers, and the value of investing in people within organizations. The discussion emphasizes the need for leaders to recognize and support their teams, fostering an environment where individuals feel seen and heard. Takeaways Kevin Kowalick made a bold decision to pivot from ad tech to academia. The concept of a 'multipreneur' reflects a desire for diverse career experiences. Coaching is about helping individuals unlock their potential and overcome fear. Mentorship plays a crucial role in shaping leadership styles and approaches. Emerging leaders often lack the training needed to transition from doers to leaders. Real-world examples enhance learning and engagement in the classroom. Fear is a common barrier to career advancement and change. Investing in employee development is more cost-effective than replacing talent. Leaders should prioritize making their team members feel valued and heard. Personal experiences in the industry can inform and enrich teaching and coaching. Chapters 00:00 The Bold Career Pivot 02:33 The Journey to Academia and Coaching 05:46 Support Systems and Family Dynamics 08:38 Influential Mentors and Leadership Lessons 11:44 Transitioning from Doer to Leader 14:31 Real-World Impact of Coaching 17:42 Bridging Theory and Practice in Education 20:28 Preparing Emerging Leaders 23:38 Overcoming Fear and Career Stagnation 26:13 Investing in People and Coaching

    29 min

  3. OCT 1

    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

    31 min

  4. SEP 16

    OhHello Ep. 105: Unlocking Potential Through Mentorship with Breck Mahoney

    In this conversation, Breck Mahoney, a senior account executive at Attain, discusses his experiences with mentorship and professional growth through the OhHello platform. He emphasizes the importance of intentionality and support in the workplace, highlighting how access to mentors has positively influenced his career. Breck shares insights on the culture at Attain and the value of investing in employee development, ultimately advocating for the benefits of mentorship and networking in achieving one's full potential. Takeaways Breck has been with Attain for nearly three years. Mentorship has helped Breck solidify a plan for career growth. Access to mentors has shifted how colleagues view Breck. Having support allows for taking more risks in the workplace. OhHello is filled with experienced individuals who want to invest in others. Companies not using OhHello miss out on potential growth. Breck encourages others to ask their employers for OhHello access. Attain's leadership prioritizes employee development. Support and intentionality are key themes in Breck's experience. Fresh perspectives from mentors can be very impactful. Chapters 00:00 Introduction to Breck Mahoney and Attain 01:19 The Impact of Mentorship on Career Growth 03:25 Access to Expertise and Its Influence 05:04 The Value of OhHello for Professional Development 07:06 Support and Intentionality in the Workplace 07:57 Final Thoughts on Mentorship and Growth

    9 min

  5. SEP 3

    OhHello Ep. 104 Riding the Waves of Change: Lessons from Advertising & Tech Leader Sam Bloom

    Sam Bloom’s career spans over two decades at the forefront of advertising, marketing, and technology. From launching digital units before the industry even recognized their value, to leading partnerships at PMG, to learning lessons from influential mentors, Sam has lived through the rapid evolution of media and tech. In this conversation with Jeremy Bloom, he reflects on leadership, mentorship, adaptability, and the importance of both doing and unlearning to thrive in a fast-moving industry. Takeaways Advertising roots: Third-generation advertiser shaped by family legacy. Digital pioneer: Built one of the first digital units at Camelot Tech lessons: Learned agility and speed in the early days of digital media. Mentorship: Guided by key figures throughout his career. Unlearning: Success comes from adaptability and letting go of old methods. Leadership style: Leads with empathy, trust, and open communication. Doer’s mindset: Believes growth comes from action and hands-on learning. Chapters 0:13 Introductions & Journey: Jeremy and Sam kick off with humor and Sam’s path from Camelot to PMG. 03:18 Mentors: Lessons from early influences and family roots in advertising. 07:01 Leadership & Pressure: Building trust, empathy, and resilience in a results-driven industry. 13:27 Pivots & Satisfaction: Career-defining moves from consulting to Blockbuster, and finding personal fulfillment. 20:00 Mentorship & Curiosity: Paying it forward, asking better questions, and thriving in the media's fast-changing world. 25:33 Unlearning & Advice: Adapting to change, embracing new waves, and encouraging young pros to go do.

    34 min

  6. AUG 19

    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

    43 min

  7. AUG 5

    OhHello Ep. 102: The Journey of an Accidental Entrepreneur with Andrew Yeung

    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 Andrew moved to New York during the pandemic to start a new life. He founded Fibe, a tech events business, to connect people. Community building was essential during the isolation of COVID-19. Andrew emphasizes the importance of kindness in networking. The 'third door' concept highlights alternative paths to success. Mentorship has played a crucial role in Andrew's journey. Creating a supportive work environment fosters alignment and growth. Taking small actions can lead to significant opportunities. It's important to embrace uncertainty in entrepreneurship. Now is a great time to start experimenting with ideas. Chapters00:00 Introduction to Andrew Yeung02:44 The Birth of Fibe and Early Challenges05:34 Building Community and Connection08:38 The Concept of the Third Door11:46 The Role of Mentorship in Growth14:33 Creating a Supportive Work Environment17:28 Encouragement for Aspiring Entrepreneurs20:32 Reflections on Career Choices23:17 Final Thoughts and Advice

    25 min

  8. JUL 29

    OhHello Ep. 101 The Rebound Effect: Understanding BuyerExperience with Brian Hamor

    🎙️ In this episode of The OhHello Pod, Jeremy Bloom, founder of OhHello.ai, sits down with Brian Hamor, founder of BuyerExperience shares his journey from a basketball career to becoming a successful entrepreneur and founder of BuyerExperience. He discusses the importance of understanding buyer feedback, the impact of mentorship, and the core values that drive his business. Brian emphasizes the significance of empathy, preparation, and skill acquisition in both personal and professional growth, while also reflecting on how his experiences in sports have shaped his leadership style. Takeaways ✔️ Brian's journey from basketball to entrepreneurship is inspiring. ✔️ Understanding buyer feedback is crucial for sales success. ✔️ Leadership requires adapting to different personality types. ✔️ Empathy in business is rooted in preparation and understanding. ✔️ Mentorship plays a vital role in personal and professional growth. ✔️Trustworthiness is a key value in sales and business. ✔️Skill acquisition is essential in the age of AI. ✔️ Preparation for meetings can lead to unexpected opportunities. ✔️ Core values shape the culture and direction of a business. ✔️ Continuous learning is important at any stage of life. Chapters00:00 Introduction and Background of Brian Hamor02:47 The Concept of BuyerExperience05:39 Leadership Lessons from Basketball08:45 The Importance of Preparation and Empathy11:42 The Role of Mentorship in Personal Growth14:44 Core Values Driving Buyer Experience17:22 Future of B2B Growth and Skill Acquisition

    19 min
See All (112)

5
out of 5
11 Ratings

About

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.

Information

You Might Also Like