OhHello with Jeremy Bloom

By Jeremy Bloom

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.a... more

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FAQs about OhHello with Jeremy Bloom:

How many episodes does OhHello with Jeremy Bloom have?

The podcast currently has 131 episodes available.

OhHello with Jeremy Bloom episodes:

June 02, 2026OhHello 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
...more
32min
May 26, 2026OhHello 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
...more
32min
May 19, 2026OhHello 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
...more
25min
May 12, 2026OhHello 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.
...more
29min
May 05, 2026OhHello 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
...more
23min
April 21, 2026OhHello 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
...more
19min
April 14, 2026OhHello 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
...more
23min
March 31, 2026OhHello 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
...more
17min
March 24, 2026OhHello Ep. 119 On Confidence, Career Pivots & Choosing Movement Over Comfort
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
...more
23min
March 17, 2026OhHello Ep. 118 Jason Loehr, Data & AI Advisor: How Empathy, Curiosity & Data Drive Better Leadership
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.
...more
18min

FAQs about OhHello with Jeremy Bloom:

How many episodes does OhHello with Jeremy Bloom have?

The podcast currently has 131 episodes available.