Practical Pivots

In this episode of Practical Pivots, host Steve Pockross sits down with serial scale-up CEO John Allen to explore how to take over companies from founders, and lead them from stagnation to growth, and then exit. John shares his approach to stepping into investor-backed companies, building trust with boards, and making decisions by first understanding the financial model and the people involved. The conversation also digs into the difference between a thoughtful pivot and a reactive scramble, the importance of rev ops and operational discipline, and the story behind EzaLife, his current medical device startup creating disposable securement devices that help prevent painful, costly complications for patients and families.

On this episode of Practical Pivots, host Steve Pockross rewinds the sharpest go-to-market lessons from the show’s most insightful guests to help founders navigate a world where software is cheap, AI is everywhere, and attention is scarce. Drawing on 12 hard-won insights from operators, VCs, and AI leaders, Steve breaks down why being more human is the real competitive edge, why distribution now beats product, how to define product-market fit in plain English, and why clarity and focus will outlast every stunt and channel hack. If you’re stuck on plateaus, over-investing in tactics, or wondering where AI truly belongs in your GTM motion, this highlight reel gives you a crisp playbook for building trust, proving demand, and scaling what actually works in 2026.

Steve Pockross sits down with Marc Nager, co-founder and general partner at Howdy, a rural Colorado-focused venture fund breaking ground with its unconventional name and a bold, investment approach. From keen insights on growth investing lessons that span the tech market to specific insights on building rural-focused tech startups, Marc shares how connecting talent, capital, and vision far from traditional tech hubs is reshaping what success looks like. Together, they explore the importance of founder self-awareness, overcoming growth plateaus, the evolving landscape of impact investing, the key to a great rebrand, and how AI is rewriting the rules for entrepreneurs and investors alike. Get ready for a playful and insightful conversation about capital, community, and the power of building companies in unexpected places.About MarcMarc Nager is the co‑founder and Managing Partner at Howdy Partners (formerly Greater Colorado Venture Fund), a venture firm backing early‑stage rural tech companies in Colorado and beyond. Previously, he oversaw global startup efforts as CEO of Startup Weekend and UP Global — programs that helped mobilize hundreds of thousands of entrepreneurs in 700+ cities around the world. Before that, Marc served as Chief Community Officer at Techstars and Managing Director of the Telluride Venture Accelerator, giving him deep experience in accelerator‑led startup growth and community‑driven ecosystems. He now lives in Southwest Colorado and dedicates his work to proving that top‑tier startups — even rocket‑science level ones — can be built far from traditional tech hubs. 

On this episode of Practical Pivots, marketing veteran Rachel Shayne, of B2B R&D, unpacks why “brand is your moat” and how the real challenge isn’t besting your competitors, but cutting through marketplace confusion. From her insights working with technical founders, Shayne lays out her playbook for building resilient, memorable brands in complex industries. Whether you’re leading a high-growth tech venture or steering strategy in a legacy sector, this interview offers the candid perspective and actionable inspiration today’s business decision-makers crave.About Rachel Rachel Shayne is a fractional CMO and brand strategist known for translating complex clean-tech and energy science into market conviction. She has helped create entirely new categories across methane monitoring, geothermal baseload power, and other frontier sectors—using disciplined storytelling to move customers, investors, and industries.Her career spans global consumer powerhouses such as P&G, Nestlé, and Sephora, as well as some of the most innovative climate-tech and deep-tech companies, including GreenFire Energy, LongPath Technologies, Project Canary, Sionic Energy, and TrelliSense. That blend of Fortune-50 rigor and venture-backed scrappiness shapes a unique approach few CMOs can match.Shayne is widely recognized for aligning founders, boards, and teams around clear narratives that fuel growth, culture, and category leadership. Her work has supported more than $200M in capital raised, driven market share above 60%, and positioned multiple brands as leaders in the energy transition.She also serves as a mentor with Blackstone Entrepreneurs’ Network, TechStars, and CU Leeds—reflecting a commitment to developing the people who will lead the next generation of markets.

In a departure from his usual role as host, Steve Pockross—accomplished CEO and fractional Chief Growth Officer—takes the guest seat in this episode, with the insightful Suneet Bhatt stepping in as interviewer. This special conversation highlights Steve’s frameworks and philosophy for instigating growth in the hyper-complex startup environment. Drawing from a wealth of executive experience, Steve elucidates the subtle art of diagnosing organizational stagnation, orchestrating strategic pivots, and cultivating a culture of continuous learning. As Steve reflects, “The real work of building a company comes from the 1000 micro interactions every single week.” With 1000s of customer and interactions, how do you iterate your way toward the North Star of growth - and still make it feel like this ongoing hard work has the drama of pivots? This episode is essential listening for founders, operators, and investors seeking not just growth, but enduring transformation.About SteveSteve Pockross is a seasoned CEO and fractional Chief Growth Officer renowned for guiding founders and leadership teams through the ambiguous, high-stakes moments that follow early startup success. His unique expertise lies in diagnosing the root causes of stalled growth—whether in sales, marketing, leadership, or product-market fit—and crafting practical, actionable strategies that drive real results. Steve’s approach is both analytical and empathetic: he excels at building cultures of trust, aligning teams around a clear North Star, and breaks down complex challenges into manageable footholds. He is especially effective with founders who are “stuck” after initial traction, ambitious to scale, and open to transformative change. Steve’s ideal clients are growth-stage startups or founder-led companies seeking a trusted advisor to help them prioritize, pivot, and unlock their next phase of sustainable growth. www.practicalpivots.co

Startup advisor Hunter Albright says the secret to early-stage growth is cutting through the complexity and finding where real momentum lives. On the latest episode of Practical Pivots, Albright, who’s worked at the crossroads of technology, business strategy and human behavior, explains that while AI is just a tool, the explosion in data and compute power has changed the game for founders. He urges entrepreneurs to focus on building consistency and warns against chasing every new trend. Albright also highlights a surprising shift: “People are swinging away from digital products and services, and wanting to get back to things that are more analog and face to face.” For startups looking to scale, he recommends frameworks like EOS to bring “calm to the chaos” and help teams prioritize what matters most.About Hunterhttps://www.linkedin.com/in/hunteralbright/

Adam Burrows, co-founder of Range Ventures, breaks down the elusive keys to success of early-stage startup investing, from the qualities that set standout founders apart to the challenges of navigating today’s venture capital landscape. How do you know what to invest in when the company you’re investing in might barely have a product? The conversation explores common missteps in early startup fundraising, the hype and hazards of AI-driven investments, and the unique strengths of Colorado’s tech community. Burrows emphasizes the critical role of clearly communicating what your product does, noting, “If I get off a call with a founder and I don’t immediately understand what they’re doing, it’s a no.” His candid insights offer a rare look into the mindset of an investor who values both conviction and practical execution. Check out the interview on our new YouTube Channel too! About Adam Burrows: https://range.vc/https://www.linkedin.com/in/burrowsadam/

Join host Steve Pockross as he sits down with executive coach and former CEO Derek Pilling to explore the real-world impact of values-based leadership in startups and high-growth companies. This episode continues the discussion from the recent episode with Kellogg School of Management Professor Harry Kraemer on values-based leadership as we focus on applying those principles in the real world. In this episode, Derek shares why aligning your actions with your deepest values isn’t just a personal pursuit, but a business imperative for effective leadership. Discover practical tools for identifying your core values, actionable strategies for living them out—even in the chaos of company building—and hear real-life stories of how authentic leadership can transform teams and drive organizational success. Whether you’re a founder, executive, or aspiring leader, this episode offers research-backed insights and hands-on advice to help you lead with integrity and purpose. Learn more about Derek and his work at https://derekpilling.com/ or https://www.linkedin.com/in/dpilling/

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 RobertsonNiel 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/

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 ColoradoMick 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