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

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 Leadershiphttps://harrykraemer.org

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 OrganCEO 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 Showhttps://www.categorynauts.comhttps://www.linkedin.com/in/markorgan

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/therealbobwoldhttps://www.quantumrings.com

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 Linkedinplymouthgp.com

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.

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 ShannonFounder & CEO: StoryvineCo-Founder & President: AI SalonCreator & Host: AI Learning Lab (TikTok)Author: Collective Intelligence in the Age of AI & AI Futures: An AnthologyQuantum CipherSydney, An Artificial Love Story PodcastSydney Soundtrack Preview

In the first episode of the rebooted podcast, business coach Eric Marcoullier shares his expertise on innovation and startup growth. He discusses navigating funding cycles, the significance of curiosity, and his coaching methods for CEOs facing economic challenges. www.marcoullier.comwww.linkedin.com/in/obviousstartupadvice

Devin Bramhall and Margaret Kelsey, the co-hosts of Don't Say Content, bring their frank perspectives to bear on everything from how we should be measuring brand marketing, to the uncanny valleys of AI, to why marketers need to stop blaming their orgs.

Suneet is an industry veteran who has led marketing teams, successfully earned B Corp certifications, and dabbled in venture capital.  This conversation is a masterclass on what positive, effective leadership looks like in the current age. 

4x CMO and current Chief Marketing Officer at Rembrand, Cory Treffiletti joined Yes, and Marketing for a deep dive into the ways AI is influencing his data-driven storytelling approach. (Plus, some tough love for execs, a look at his must-try AI tools, and a few life lessons we can all learn from.)

As CEO of Volume 9, a Denver-based marketing agency, Natalie Henley stays on the ball when it comes to marketing trends to follow (and which ones are just passing fads.) Tune in to hear how her agency approaches the AI revolution and prioritizes winning organic traffic for their clients in an ever-evolving landscape by keeping it old-school.

Ty Magnin, CEO of Animalz, isn't interested in pretending to be Nostradamus. The marketing world is constantly evolving, so rather than try to predict the future, he's changing with it. Hear how he and the Animalz team are adjusting their strategies for success, finding inventive ways to incorporate AI into their workflows, and exploring distribution channels beyond SEO to cultivate results for their clients. 

Co-founder of the Content Marketing Institute, current Chief Troublemaker at The Content Advisory, and author of Content Marketing Strategy: Harness the Power of Your Brand’s Voice, Robert Rose is a marketing powerhouse. This bona fide industry legend digs into how we should be using AI to create profitable workflows, the impact of AI on search and SEO, and how brand influences our content strategies. 

CEO of Agency Management Institute Drew McLellan brings over thirty years of expertise to dive deep into how agencies are finding success in the current economic climate by deploying AI in inventive ways. 

Leading AI ethicist Olivia Gambelin shares insights on the adoption of generative AI, how synthetic data preserves the privacy of the public, and the strategic development and implementation of AI as it impacts marketers. 

Greg Head, who has spent the past 30 years leading, growing, and advising software companies, shares why VC funding is misunderstood and over-prescribed, how AI will change the future of marketing, and explains the world of practical founders.

Caitlin Bartley, CEO of female-only marketing agency cred, shares her approach to digging deep with clients, the importance of staying flexible, and how to find creative solutions in the wild world of PR and event marketing.

Ken "Magma" Marshall, Chief Growth Officer at RevenueZen, explains the secret sauce of B2B growth, how he transitioned from entrepreneur to agency owner to agency seller, and how to achieve legitimate fame on LinkedIn.

Gordon Boyes, CEO of Concept3D, shares learnings from his "three and several halves" CEO gigs, including how to choose career opportunities that play to your strengths and how to manage long sales cycles.

As host of the Marketing Book Podcast, Doug shares his picks for the best marketing books of 2022, including the best books to read during a recession and some classics we can all read again.

Lily explains how brands of different sizes should be thinking about EAT, what SEOs have deciphered from Google patents, and the new search technologies she's most excited about.

Pearl discusses the current state and future of content marketing, the challenges of building YMYL content at scale, how CEOs can prioritize tasks to better achieve growth, and offers advice for aspiring leaders.

Rachel discusses leading tech startups, investing strategies, writing her memoir, the importance of process, and how lessons from all these activities have made her a better marketer.

Ashley shares what it took to turn Cuties into a lunchbox phenomenon, plus other strategies for marketing commodities from her experience heading marketing at brands like The Wonderful Company and SunFed Ranch.

The president of Applied Brand Science shares what every brand's buyer distribution looks like and most common mistakes we make with consumer research.

Hope shares what marketing teams are getting wrong with video marketing today, how to prepare for the future of video marketing, and the best part of having a co-founder at video marketing firm Lemonlight.

Andrea explains the seven values of agile marketing and the philosophy behind AgileSherpas. She also shares how Eminem helped her become an entrepreneur.

Paddy shares the biggest trends in link-building today, what agencies need to be doing differently, and what he's learned as the co-founder of superstar agency Aira.

David Cancel of Drift, Peep Laja of Wynter, Chris Savage of Wistia, Niel Robertson of Influence.co, Stephen Lease of Goodr, Gary Swart, formerly of Upwork, Shafqat Islam of NewsCred, Sean Griffey of Industry Dive, Vaibhav Jain of Hublio, Rand Fishkin of Sparktoro, Jimmy Daly of Superpath, and Eric Remer of EverCommerce share wisdom of all sorts based on their experiences as founders and CEOs.

As a DEI+ expert, Ashley shares what she's seeing companies get right (and wrong) with equity and inclusion initiatives. She also explains why perfectionism is a product of white supremacy culture.

The co-founder of Impact Museums explains how Ticketmaster's best-selling event of 2021 came to be and forecasts future trends in immersive entertainment.

The founder of EverCommerce shares his lessons from various stages of startup growth, how he knew it was time to start acquiring other businesses, and what it takes to market to SMBs.

As the founder of CMO Huddles and award-winning agency Renegade, Drew shares the four characteristics of successful CMOs, the conversation to have with your CFO, and how to make a rebrand stick.

Amanda explains how to create newsworthy content and breaks down the role of earned media and PR, based on her experience as a journalist and as head of marketing at Stacker.

Author and professor Nancy Lee shares what social marketing is, how most government agencies could be doing it better, and some of the toughest campaigns she's worked on to influence public behavior.

Hawke Media founder Erik talks TikTok over Facebook, explains the key to marketing to Gen Z, and gives advice for wannabe agency owners.

Evelyn explains what brand adolescence is, how to identify the symptoms, and how to navigate it successfully.

Andy Crestodina, Tim Riesterer, Ashley Faus, Dave Kellogg, Cassidy Shield, Rand Fishkin, Ritesh Patel, Sean Griffey, Denise and Jim Franklin, Doug Kessler, Kait Creamer, and Melanie Deziel take down some of marketing's most accepted wisdom.

The Franklins explain what they look for when investing in a startup. They also share the structure for their own marriage OS and why marriage offsites should be a thing.

Dan talks growth strategies, innovation, and why most brands aren't as special as they think. He also shares the most important job a marketer has.