WTF Is Up?

Omar Garriott + Jeremy Schifeling
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Two entrepreneurs, former tech execs, and bestselling authors here help you understand...WTF is going on. So you can be a smarter friend, colleague, and partner. Each episode, we give you the quick hits on an important but slightly-under-the-radar topic. And not just tell you WTF is going on, but tell you WTF you can actually DO about it. Unlike most every other podcast. News + views you can use! Email us: WTFIsUpShow@gmail.com.

  1. 1d ago

    Entrepreneurship's Moment?

    Discussing the future of work (spoiler: it’s DIY!) and the future of college with our former LinkedIn colleague, startup evangelist, and friend of the pod John Hill. Summary: In this episode, John Hill shares his insights on the evolving landscape of employment, higher education, and entrepreneurship. We explore how AI, the creator economy, and innovative university models are shaping the work – and learning to prepare for work. Key Topics: The importance of building your own job in a changing marketHow universities can support entrepreneurship and AI literacyThe role of authenticity, soft skills, and in-person experiences in the AI eraNew approaches to higher education, including buying and reinventing collegesPractical advice for students, entrepreneurs, and university leaders Timestamps: 00:37 - John Hill’s diverse career in higher ed, startups, and corporate roles 02:02 - The shift from finding jobs to creating them in today’s economy 04:12 - Why entrepreneurs should focus on building their personal and professional brand 05:20 - The impact of gig economy, creator economy, and AI on entry-level jobs 06:07 - Universities supporting entrepreneurship and AI literacy 08:16 - Hands-on entrepreneurial education with WAP platform at Michigan State 09:29 - Leveraging AI for experiential learning and soft skills development 10:08 - The relevance of LinkedIn in an AI-driven landscape 12:19 - Authenticity and trust as currency in the future workforce 13:34 - The importance of soft skills in a screen-dominated world 15:20 - The decline of small and liberal arts colleges and innovative solutions 16:00 - John Hill’s real-life venture in buying and reinventing a college 18:46 - Strategic priorities for LinkedIn’s future relevance 20:00 - How universities can foster community and collaboration instead of competition 21:21 - Advice for parents preparing their teens for an uncertain future 22:22 - Closing thoughts: embracing AI, entrepreneurship, and kindness

    23 min

  2. Jun 19

    The Job Market for New Grads: Q&A with Christian Garcia

    Christian Garcia has built a career helping young people build theirs. He shares his incredible journey and his insights on the evolving job market and the enduring value of college. This conversation offers practical advice for recent graduates, educators, and anyone navigating career transitions amidst rapid change. Summary: The episode underscores the importance of adaptability, lifelong learning, and the social mission of higher education in empowering individuals and society amidst economic and technological shifts. Key Topics: Christian Garcia’s inspiring career path from media aspirations to higher education leadershipThe importance of pivoting, resilience, and mentorship in career developmentImpact of economic downturns and current market challenges on recent graduatesEssential skills for future-proof careers: communication, critical thinking, adaptability, and understanding AIThe value of liberal arts education and interdisciplinary learning in today’s economyHow employers are adjusting expectations and the gap between student skills and industry needsInnovative ideas for reimagining higher education for shorter, experiential, and industry-integrated programsPractical advice for recent grads: job search strategies, networking, and mindset shiftsThe long-term social mobility and transformative power of college education Chapters: 00:00 - Introduction and Christian Garcia’s career highlights 02:14 - The pivotal moments and inflection points in Christian’s career journey 06:11 - The value of mentorship and pivoting in professional growth 10:10 - Transition from student affairs to career services at UVA 12:03 - The current state of the job market and adaptation strategies 16:31 - Advice for students seeking their North Star amid chaos 19:07 - Skills for future-proof careers: soft skills and AI literacy 20:58 - Employer perspectives on the class of 2026 and beyond 24:04 - The enduring value of college for social mobility and personal growth 27:40 - Rethinking higher education: shorter, industry-connected, interdisciplinary models 32:56 - The importance of integrating industry experience into curricula 35:31 - Imagining a new university embodying innovation and flexibility 39:05 - Fun rapid-fire questions on UVA vs. University of Miami, nightlife, and community

    40 min

  3. May 12

    For-Profit or For-Impact?

    For-profit, not-for-profit, for-impact...What's the difference anymore? We talk with former edtech exec and founder Matt Haldeman about building a cross-sector career, entrepreneurship pro tips, and whether non-profit products can be monetized. Summary: In this episode, Matt shares insights on leveraging capital in the non-profit space, managing career pivots, and blending mission with financial sustainability — valuable lessons for aspiring changemakers. Takeaways: An impact-driven career is possible across sectorsEntrepreneurs must navigate various legal structures (non-profit, B-Corps, public benefit corporations, etc.), but these traditional lines are blurringEarly-stage founders must first focus on solving one person for one problem Chapters: 01:03 - A black-and-white view of impact 02:24 - From the classroom to corporate leadership 05:02 - Inflection points and defining impact 07:56 - Lessons from a successful entrepreneur's sector pivot 09:27 - Advice for young professionals: planning versus adaptability 11:55 - The importance of testing careers early 13:10 - An impact investing thesis 16:36 - The role of capital in scaling non-profit products and innovations 20:12 - Differences and similarities between non-profits and for-profit entities 22:45 - The future of blended models: Non-profit, B-Corps, and C-Corps 27:00 - Start small, solve for one, iterate 29:10 - Examples of innovative for-impact products

    33 min

  4. May 2

    WTF is up with recruiting?

    A behind-the-scenes look at the state of corporate recruiting and the hiring outlook for new grads and old grads alike! Summary: In this episode of "WTF is Up," Jeremy and Omar chat with William Chichester, a seasoned talent acquisition leader with 20 years of experience across industries from Target to Peloton. William shares insider insights on university recruiting, market trends, and practical strategies for job seekers navigating today’s competitive landscape. Takeaways: AI is disrupting entry-level hiring, but we must separate reality from mythEconomic fluctuations drive hiring. Everything is cyclicalNetworking as career cheat code: Practical tips for career starters to build relationships and stand outSoft skills drive success Chapters: 00:00 - Introduction to William Chichester: A career in talent acquisition 02:07 - Highlights of William’s diverse recruiting career including Target and Peloton 04:29 - The importance of attitude and mindset in career progression 06:43 - How university recruitment has evolved and the significance of core schools 09:03 - Impact of macroeconomic factors versus AI on hiring practices 11:13 - Similarities between today’s market and the 2008 financial crisis 12:26 - The relevance of college degrees in the current hiring landscape 14:28 - The "Silver Tsunami" and demand for blue-collar skills in the future 16:42 - Practical advice for students: leveraging university career services and networking 18:01 - Building a personal brand and relationship currency for job hunting 20:35 - Strategies for introverts to network effectively on LinkedIn 22:13 - Developing durable professional skills like resilience and empathy 25:12 - The critical role of empathy in talent acquisition and working relationships 28:48 - How to succeed in a tight job market with limited opportunities 30:52 - William’s personal story of overcoming barriers through networking and grit 34:47 - The importance of authentic relationship building over reliance on ATS 37:02 - Counterintuitive advice and “career cheat codes” for current students 38:57 - Using AI to craft personalized outreach and elevator pitches 42:22 - William’s final thoughts on resilience, patience, and taking control of your career 44:10 - Connecting with William for further insights Resources & Links: ⁠⁠LinkedIn - William Chichester⁠⁠⁠⁠Podcast: Bald, Bold, & Hired⁠⁠⁠⁠Book: "Linked"⁠⁠⁠⁠University of Virginia Career Services⁠

    45 min

  5. Apr 13

    Who Moved My Career?

    Real talk with longtime tech and nonprofit exec Nicole McNamara about job success, job loss, job security, job searching, and jobs as identity. Summary Omar and Nicole discuss her 25-year career journey, navigating corporate leadership, career pivots, and the emotional impact of job loss. She offers practical advice on self-awareness, storytelling, and adapting to the rapidly changing future of work, emphasizing the importance of human-centered skills in an AI-driven world. Takeaways Self-awareness as a foundation for career growthStorytelling as a tool for resilience and connection"Mack Truck Moments” and the mindset needed to effectively navigate change Chapters 00:00 Introduction to Nicole McNamara's Career Journey 01:46 Pivots and Career Decisions 04:35 Reinventing Through Education 08:56 Navigating Job Loss and Identity 12:38 The Impact of Grief and Love on Career 15:38 Podcasting as a Tool for Healing 18:14 Lessons Learned from the Job Market 21:44 The Importance of Self-Discovery 24:40 The Future of Work and Career Management 30:16 The Shift in Corporate Loyalty 37:27 Preparing for Inevitable Career Changes Resources Nicole McNamara's LinkedIn - https://www.linkedin.com/in/nicollemcnamara/Future of Work Reports - World Economic Forum - https://www.weforum.org/reports/the-future-of-workStorytelling in Career Development - Harvard Business Review - https://hbr.org/2020/01/the-power-of-storytelling-in-career-development

    40 min

  6. Mar 27

    Unbreakable: AI-proofing your career

    The cheat code for how professionals—and job seekers—can find success in an AI-driven world. (Spoiler: It’s all goes back to humans.) Summary Takeaways AI is changing job roles, especially entry-level and technical positions.There are four key skills you need amidst these changes.Leveling up your skills involves mastering human connection, AI integration, and building support networks.Show, don't just tell, your skills through proactive actions and storytelling.Referrals have become even more valuable in an AI-saturated application process.Diversify your income streams and career pursuits to build resilience. Chapters 00:00 Introduction to Unbreakable: AI and Career Resilience 02:45 The Four Human and AI Skills for Success 05:37 Becoming an Indispensable Team Member 07:39 Job Search Strategies in the Age of AI 10:00 The Importance of Referrals and Trust 12:38 Connecting with Recruiters and Hiring Managers 15:23 Diversifying Your Career Options

    20 min

  7. Mar 16

    How to Hack Work

    Let’s hack work! Tips for getting ahead in a job (and getting the job in the first place), getting noticed, and getting in good with the people that matter most. About this episode: Summary In this episode, Omar and Jeremy discuss work hacks that can help individuals navigate their careers more effectively. They emphasize the importance of working smarter rather than harder, building relationships, and understanding what truly matters in the workplace. The conversation covers practical tips for networking, engaging with colleagues, and preparing for interviews, all while highlighting the significance of empathy and human connection in professional settings. Takeaways Work smarter not (necessarily) harder.Focus on what matters to your boss to prioritize tasks.Building relationships through lunch invites can expand your network.In-demand skills include communication and a proactive attitude.Show your hunger and initiative by sharing work in progress.Always aim to add value and solve problems independently.Engagement in meetings is crucial; always contribute something.Empathy is key in understanding your boss's challenges.Use specific examples in interviews to demonstrate your capabilities.Finding meaning in work enhances job satisfaction and performance. Chapters 02:31 Working Smarter, Not Harder 06:51 The Middle School Lunch Effect 10:14 In-Demand Skills and Attitude 11:56 Demonstrating Hunger and Initiative 15:35 Building a Positive Reputation 18:36 Engagement and Contribution 26:25 Empathy in the Workplace 28:38 Interviewing Faux Pas 36:52 Finding Meaning in Work

    31 min

  8. 12/23/2025

    WTF is up with 2025--and 2026?

    From AI bubbles and slop to economic and job market roller coasters, WTF did we all just live through in 2025? And what's in store for 2026? About this episode: Summary In this episode, Jeremy and Omar reflect on the significant events of 2025, discussing economic trends, the impact of AI, the rise of entrepreneurship, and the challenges faced by tech giants. They also explore cultural shifts and make predictions for 2026, emphasizing the importance of human involvement in the evolving landscape. Takeaways 2025 was marked by economic uncertainty and job market challenges.AI's progress has plateaued, raising concerns about its future utility.Entrepreneurship is on the rise, especially among Gen Z.Tech giants faced minimal consequences in antitrust trials.Cultural and political shifts are influencing public sentiment.Predictions for 2026 include ​peak AI, potential downturns in the job market​, and a temporary preservation of human roles.​Affordability​ will be a central political message​, and the common touch will be political gold.​Final predictions: The ​2026 World Cup​! Chapters 2025 Year in Review: Highlights and Reflections 05:34 The Economy: Trends and Predictions 11:18 AI: Progress, Challenges, and Future Outlook 17:26 Entrepreneurship: The Rise of the Side Hustle 21:11 Cultural and Political Shifts: A Year of Change 21:38 Navigating Political Discontent 23:41 The Future of AI: Predictions and Impacts 36:26 Job Market Outlook for 2026 39:41 Cultural Shifts and the 2026 World Cup

    43 min
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About

Two entrepreneurs, former tech execs, and bestselling authors here help you understand...WTF is going on. So you can be a smarter friend, colleague, and partner. Each episode, we give you the quick hits on an important but slightly-under-the-radar topic. And not just tell you WTF is going on, but tell you WTF you can actually DO about it. Unlike most every other podcast. News + views you can use! Email us: WTFIsUpShow@gmail.com.

Information

  • Creator
    Omar Garriott + Jeremy Schifeling
  • Years Active
    2025 - 2026
  • Episodes
    18
  • Rating
    Explicit
  • Copyright
    © 2025 Omar Garriott + Jeremy Schifeling
  • Show Website
    WTF Is Up?