Practical Pivots

Steve Pockross
  • 4.9 (71)
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Practical Pivots

Practical Pivots is the go-to source for startup leaders and investors asking, “What do we do next?”. Each episode, we talk with a wide array of experts to guide companies to disrupt the undisruptable, turn setbacks into scale-ups, and transform plateaus into pivots. 

  1. JUN 27

    The Great Reversal: Neil Robertson on Why Distribution Eats Product in the AI Age

    In this episode of Practical Pivots, serial entrepreneur Niel Robertson shares his deep insights into the transformative power of AI in business, drawing from his experience of co-founding seven venture-backed startups. Robertson explores the nuanced landscape of artificial intelligence, discussing everything from the Shopify CEO's AI manifesto to the critical importance of distribution in the modern tech economy. Through his current venture, Winslow, he demonstrates how AI can revolutionize HR workflows, and offers candid perspectives on workforce productivity, the evolving role of technology, and the necessity for businesses to overcome their AI adoption paralysis. With a mix of technical expertise and strategic vision, Robertson provides a roadmap for entrepreneurs and leaders navigating the complex intersection of AI, innovation, and organizational change. About Niel Robertson Niel Robertson is a serial entrepreneur and executive, currently CEO of Winslow, an AI HR software company. He previously founded and led startups including influence.co, Trada, and Service Metrics. Robertson is recognized for his expertise in building and scaling technology companies across the HR, advertising, and creator economy sectors. https://www.linkedin.com/in/nielrobertson/ https://usewinslow.com/

    44 min

  2. JUN 9

    From Product Market Fit to Exit with Mick Freeman

    In this episode of Practical Pivots, Mick Freeman, CEO of BEN Colorado, unveils the hidden challenges and untapped potential of startup ecosystems. Drawing from his diverse entrepreneurial background, Freeman candidly discusses the critical importance of bootstrapping until achieving true product market fit - which he defines simply as "somebody bought it twice" - and warns against premature fundraising that can dilute founders' equity. He reveals surprising insights about Colorado's unique collaborative startup culture, where entrepreneurs view the business landscape as an expandable pie rather than a zero-sum game. Freeman passionately advocates for entrepreneurs to break down their ego barriers and actively seek help, highlighting the mental health challenges in startup life and the transformative power of vulnerability. With provocative observations about leadership, financing strategies, and the psychological hurdles of scaling businesses, Freeman offers a raw, unfiltered look into the entrepreneurial journey that will resonate with founders navigating the treacherous waters of startup growth. About Mick Freeman, CEO & Executive Director, BEN Colorado Mick Freeman is a seasoned business leader, social entrepreneur, and strategic advisor with over six years of experience as a BEN volunteer across multiple programs. His experience spans the nonprofit, private, and public sectors, including startup, scale-up, turnaround, Fortune 500, nonprofits, and for-profit social enterprises. https://www.bencolorado.org/mick-freeman

    47 min

  3. MAY 25

    Values-Based Leadership in Turbulent Times w/ Kellogg Prof. Harry Kraemer

    In this episode of Practical Pivots, host Steve Pockross sits down with Harry Kraemer, Kellogg Professor at Northwestern University and former Baxter International CEO, to explore the critical importance of values-based leadership; especially in turbulent times like these. Kraemer shares his transformative approach to leadership, emphasizing four key principles: self-reflection, balanced perspective, true self-confidence, and genuine humility. Through personal anecdotes and practical insights, he guides listeners on how to navigate complex business environments by staying true to core values, making difficult decisions with integrity, and understanding that leadership is less about technical skills and more about emotional intelligence, team building, and personal growth. This episode offers a compelling roadmap for leaders at any stage who want to lead with purpose and authenticity in today's challenging marketplace. About Harry Kraemer  Harry Kraemer is a Professor of Leadership at Northwestern University’s Kellogg School of Management. He’s been named Professor of the Year multiple times, is the author of four best-selling leadership books, and is one of the most sought-after leaders in his field. He is the former Chairman and Chief Executive Officer of Baxter International Inc., a $12 billion global healthcare company. From Values to Action: The Four Principles of Values-Based Leadership https://harrykraemer.org

    39 min

  4. APR 24

    Category Creation in the AI Era with Mark Organ

    In this episode, we talk with Mark Organ, who created not one, but two software categories: marketing automation at Eloqua and advocate marketing at Influitive. These days, he coaches founders through the highs and lows of category creation at Categorynauts — and he specializes in deeply insightful and contrarian takes.  Mark explores the evolving landscape of AI and its potential impact on business and technology. Organ projects how AI will further transform software development, scientific research, and industry strategies. He offers a nuanced perspective on technological innovation, highlighting the importance of human insight alongside machine capabilities. With a focus on practical applications and future trends, Organ provides listeners with a strategic view of how AI could reshape product development, market creation, and professional skills. His key quote, "I'm excited about the next wave of software that really could not exist without AI," encapsulates the episode's forward-looking approach to technological innovation. About Mark  Mark Organ CEO Coach at Categorynauts, Founding CEO of Influitive and Eloqua. Author of WSJ and Amazon best-seller The Messenger is the Message, and Co-Host of The Best Half Show https://www.categorynauts.com https://www.linkedin.com/in/markorgan

    39 min

  5. APR 1

    Learnings From the Quantum Realm with Bob Wold

    Bob Wold, a first-time founder in his 40s, demystifies quantum computing and shares his unexpected journey from corporate retirement to tech innovation. Diving deep into the world of quantum technology, Bob explains how his company, Quantum Rings, is developing tools to make complex computing more accessible, while revealing the potential to revolutionize industries from healthcare to cybersecurity. Beyond the technical insights, Bob candidly discusses the challenges of startup life, the importance of personal fortitude, and how meditation helped him navigate the unpredictable entrepreneurial landscape. Join us for an inspiring conversation that proves it's never too late to reinvent yourself and pursue groundbreaking technological frontiers. https://www.linkedin.com/in/therealbobwold https://www.quantumrings.com

    40 min

  6. MAR 14

    The Messy Middle: Funding Founders Where Others Won't with Brook Critchfield

    In this episode of "Yes in Marketing," Steve sits down with Brook Critchfield from Plymouth Growth to explore the nuanced world of growth equity investing. Brooke reveals how his firm uniquely serves founder-led B2B software companies stuck between venture capital and private equity, offering a refreshing alternative to traditional funding models. With engaging sports metaphors and insights from her Midwestern roots, she shares her approach to identifying promising companies, supporting founders through growth challenges, and creating sustainable business strategies. Listeners will gain valuable perspectives on startup scaling, the importance of mentorship, and how innovative investment firms are reimagining support for emerging tech companies. Brook Critchfield  Linkedin plymouthgp.com

    53 min

  7. FEB 20

    Startup Insights From Cybersecurity Investor Joe Eandi

    Joe Eandi, a partner at the Cyber Mentor Fund, shares invaluable insights with Steve on building successful startups. He emphasizes the often under-the-radar traits for building he sees as keys to success, like the importance of "market permission" and niche expertise, as well as strategies for cultivating high-performing founding teams. Eandi's seasoned perspective as a venture capitalist, former CEO and tech executive, and attorney combine with his uniquely thoughtful perspective to create a roadmap for entrepreneurs looking to navigate the dynamic and profitable startup landscape.

    38 min

  8. JAN 22

    Exploring AI's Creative Potential with Kyle Shannon

    In this episode, Kyle Shannon, a leading expert on AI and creativity, discusses the transformative impact of AI on storytelling and the creative process. He shares his "holy crapification" moments with AI and explains why embracing these tools can actually enhance creativity rather than replace it. Kyle Shannon Founder & CEO: Storyvine Co-Founder & President: AI Salon Creator & Host: AI Learning Lab (TikTok) Author: Collective Intelligence in the Age of AI & AI Futures: An Anthology Quantum Cipher Sydney, An Artificial Love Story Podcast Sydney Soundtrack Preview

    42 min
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4.9
out of 5
71 Ratings

About

Practical Pivots is the go-to source for startup leaders and investors asking, “What do we do next?”. Each episode, we talk with a wide array of experts to guide companies to disrupt the undisruptable, turn setbacks into scale-ups, and transform plateaus into pivots. 

Information

  • Creator
    Steve Pockross
  • Years Active
    2020 - 2025
  • Episodes
    140
  • Rating
    Explicit
  • Copyright
    © 2025 Practical Pivots
  • Show Website
    Practical Pivots

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