

Scaling With People
Gwenevere Crary
Tired of spinning your startup wheels but never gaining traction? Buckle up, founders and CEOs, because this podcast is your rocket fuel to profitability! Every week, we ignite explosive conversations with bold-faced founders, brainy experts, and even a few out-of-this-world vendors. Get ready to crack the code on growth, master employee engagement, and blast through your scaling goals. We’re talking real-world strategies, actionable tips, and perspectives that’ll make your business do a cosmic dance. So, strap in and prepare for lift-off!
Episodes
Mentioned books

Sep 3, 2025 • 26min
Rewriting Your Leadership Story: From Childhood Patterns to Business Growth with Dr. Sharon Spano
Send us a textWhat if the biggest obstacle to your business success isn't your strategy, market, or team—but the narrative written decades ago in your childhood?Dr. Sharon Spano joins Gwendolyn McCreary to reveal how our earliest experiences create patterns that silently shape our leadership decisions. These subconscious scripts influence everything from hiring practices to work-life integration, often creating what Sharon calls "the emptiness of success"—when leaders achieve their business goals but feel profoundly unfulfilled.This conversation goes beyond surface-level business advice to explore the deeper human systems at work in leadership. Sharon shares powerful insights on recognizing harmful patterns, embracing growth opportunities, and staying present whether at work or with family. She challenges the concept of work-life balance, suggesting instead that we aim for integration through intentional choices and full presence.For founders struggling with perfectionism, relationship patterns, or simply feeling that something's missing despite outward success, this episode offers both validation and practical steps forward. Sharon's approach combines systems thinking with developmental psychology to help leaders grow alongside their businesses rather than being outpaced by them.The discussion provides concrete tools for identifying childhood narratives, setting realistic expectations, and creating meaningful success that encompasses both business achievement and personal fulfillment. Sharon emphasizes that growth isn't about self-criticism but opportunity—each challenge offers a chance to evolve into a more effective leader.Ready to discover what might be holding you back and rewrite your leadership playbook? Take Sharon's Leader's Edge Quiz at sharonspano.com/scalingwithpeople to identify where you are in the 12 stages of human development and unlock your next level of growth.

Aug 27, 2025 • 26min
Building Flexibility at Scale: The New Survival Strategy for Modern Business with James Terry
Send us a textWorkforce flexibility isn't what you think it is. While most businesses scramble to plug staffing gaps when demand spikes, true flexibility comes from strategic planning that anticipates shifts before they happen.James Terry, a workforce transformation leader at Indeed Flex, reveals how businesses can build resilience through data-driven labor planning. "Flexibility actually starts with being able to do effective labor planning," Terry explains. "Understanding operationally what's happening on the ground level, how many orders you're getting from customers, and how demand increases or decreases over time." This approach creates a powerful flywheel effect, where each adjustment provides insights that improve future staffing decisions.The podcast dives deep into how employee expectations have fundamentally changed. Today's workers expect the same convenience and options in their employment that they experience as consumers. Just as we can order products online and have them delivered within hours, employees want flexibility in when, where, and how they work. Smart companies are adapting by rethinking traditional scheduling patterns and exploring more responsive approaches to workforce management.Perhaps most eye-opening is Terry's perspective on Employer Value Propositions. "Your EVP doesn't start after someone's been there for a year," he emphasizes. "It starts the first time they put eyeballs on your job posting." With nearly half of applicants abandoning the process if they don't hear back within a week, companies must recognize that every touchpoint shapes their ability to attract talent. The discussion also tackles AI's role in recruiting (hint: it's not about getting more applications), the importance of rating systems over resumes, and practical strategies for future-proofing against labor shortages.Ready to stop playing defense and start dominating your market through workforce innovation? Listen now and discover how flexibility at scale becomes your competitive advantage in chaotic times. As Terry advises: "Fail often and fall forward." Your workforce strategy depends on it.

Aug 20, 2025 • 24min
The Entrepreneur's Guide to Financial KPIs and Business Growth with Kyle Smith
Send us a textWhat's the real difference between profit and cash flow? For many founders without finance backgrounds, this distinction remains frustratingly opaque—yet understanding it could mean the difference between securing crucial funding or watching growth opportunities slip away.Kyle Smith, a former professional poker player who pivoted to become a CPA and co-founder of Strata Cloud Accountants, breaks down this financial conundrum with remarkable clarity on our latest episode. His journey from poker tables to spreadsheets taught him a profound lesson: unlike the zero-sum nature of gambling, business finance offers the opportunity to create genuine value for others.When Kyle and his co-founders launched their company three months into the pandemic, they faced extraordinary uncertainty. Yet this crisis presented a rare opportunity they knew wouldn't come around again. Their leap of faith offers powerful lessons about recognizing pivotal moments amid chaos and having the courage to act despite imperfect conditions.The heart of our conversation explores the most critical financial metrics business owners should track. Kyle shares a fascinating case study of a client repeatedly denied bank loans despite having consistent cash in their accounts. The culprit? A ballooning accounts payable balance that created a dangerous disconnect between their profit statements and cash position. This real-world example illustrates why founders must regularly compare net income against net cash flow and investigate any significant discrepancies.We also dive into practical KPIs that directly impact profitability—from revenue tracking that revealed a $40K monthly shortfall for one service-based business to the delicate balance between operational expenses and revenue growth during scaling phases. Kyle offers actionable advice on auditing recurring expenses (those sneaky subscription services add up fast!) and emphasizes that financial literacy isn't just for "numbers people"—it's an essential language every entrepreneur can and should learn.The episode concludes with Kyle's powerful reminder that resonates regardless of your business stage: "Don't let perfection be the enemy of progress." Ready to gain financial clarity and make more confident scaling decisions? Listen now and transform how you view your business numbers.

Aug 13, 2025 • 21min
Human Connection Wins When AI Content Floods the Market with Tye DeGrange
Send us a textTrust has become the scarcest resource in the digital marketplace. As consumer skepticism grows and advertising costs skyrocket, brands are discovering that third-party validation isn't just nice to have—it's essential for survival and growth.Digital growth strategist Tye DeGrange pulls back the curtain on how affiliate marketing has evolved from a misunderstood, often maligned tactic into a sophisticated trust-building ecosystem. "Affiliate is probably the most misunderstood and the most underrated part of performance marketing," he explains, detailing how his agency Roundbarn Labs has helped technology companies like Nextdoor, MetaQuest, and Grammarly build authentic performance marketing programs that deliver measurable results.The conversation takes a fascinating turn when exploring the intersection of AI and affiliate marketing. Brands are now seeking partnerships not just to reach consumers directly but to secure citations in AI systems like ChatGPT and Google's various LLMs. With AI-generated influencers gaining millions of followers (sometimes without disclosure), the premium on genuine human connection continues to grow. DeGrange predicts platforms facilitating authentic communication—particularly YouTube—will dominate by 2025 precisely because they're difficult for AI to replicate convincingly.For founders and marketing leaders, DeGrange offers practical guidance on when to implement affiliate strategies (typically after achieving product-market fit, around the $5M revenue mark) and how to approach matchmaking between brands and potential partners. The key? Authentic alignment that audiences can feel. As he puts it, "Kim Kardashian might be great for skincare, but maybe not for a tire company." This thoughtful approach to partnerships creates the foundation of trust that makes modern affiliate marketing effective.Ready to transform your marketing strategy from chasing clicks to building authentic trust? Listen now to discover how performance marketing can scale both your reach and your credibility in an increasingly skeptical digital landscape.

Aug 6, 2025 • 24min
From Founder to CEO: The Messy Journey of Scaling Leadership with Aviva Leebow
Send us a textEver wonder what happens when your startup outgrows its scrappy beginnings? The transition from founder to CEO isn't just about a new title – it's a fundamental shift in how you lead, who you hire, and sometimes, the painful decisions about who stays on the journey.Gwendolyn R. Curry sits down with Aviva Leebow, a Vistage Chair who coaches ambitious CEOs, to explore the leadership evolution necessary for sustainable growth. Their conversation dives into the uncomfortable truth that the people who helped build your company from nothing might not be the right ones to take it to the next level. They share strategies for having these difficult conversations while preserving relationships and respecting the contributions of early team members.The discussion highlights a critical mistake most growing companies make: promoting skilled individual contributors without providing management training. "We do not train and coach people to become good managers," Curry notes, pointing out that leadership development remains the most overlooked investment in scaling organizations. Lebo emphasizes the importance of peer groups and external resources to help leaders grow beyond their current capabilities.Perhaps most compelling is their exploration of founder self-awareness. Knowing when you've reached your leadership capacity – and being willing to surround yourself with experienced executives or even step aside – can be the difference between stagnation and continued growth. As Lebo shares through powerful examples, sometimes the greatest act of leadership is recognizing when someone else can better realize your vision.Ready to evolve your leadership approach as your company scales? Listen now to gain insights that will help you navigate the messy, inspiring journey of growing with your business rather than just alongside it.

Jul 30, 2025 • 30min
Culture as Your Competitive Edge with Lilith Christiansen
Send us a textEver wonder why some startups scale smoothly while others struggle despite having great products and funding? The secret weapon might be hiding in plain sight: organizational culture.When you're racing to build your product and secure your next funding round, culture can feel like a luxury you'll address "someday." But as our conversation with Lilith Christiansen, founder of Human Genuity, reveals, this mindset could be costing you far more than you realize.Culture isn't just about fancy values painted on your office walls. It's the invisible operating system determining how decisions get made when you're not in the room. It's how feedback flows, problems get solved, and ultimately, how your company functions at its core. Even with just five team members, you already have a culture—the question is whether you've shaped it intentionally.The stakes are surprisingly high. Christensen shares compelling stories of culture gone wrong, including a multicultural team where different feedback styles led to six months of misalignment and frustration. On the flip side, she highlights how one founder's commitment to work-life balance—demonstrated through delayed email delivery—created authentic alignment between values and actions that employees could trust.Perhaps most practical is Christensen's advice on recruiting: communicate "the way it is today versus the aspirational." Too many founders oversell their current reality during interviews, leading to disappointed new hires who expected something different. Being transparent about your challenges not only attracts the right candidates but helps you identify people with the skills to solve your specific problems.Whether you're hiring your first employee or your fiftieth, this episode offers actionable insights for building a culture that becomes your competitive advantage. Because in the end, your culture will either accelerate your growth or become the invisible barrier holding you back.

Jul 23, 2025 • 23min
The Business Blueprint: From Struggling to Scaling Successfully with James Brown
Send us a textWhat truly separates struggling businesses from thriving ones? Is it just about having a great product or brilliant marketing? According to James Brown, retired attorney and business growth expert who scaled his law firm to $8 million annually with offices in four states, success comes down to mastering seven essential components found in every successful business.This eye-opening conversation reveals how these building blocks create a framework for sustainable growth regardless of industry or company size. Brown walks us through his profound realization that "every business has the same seven working parts—the only thing that's different is what we sell." From defining clear personal income goals that inform your entire business plan to making data-driven decisions that prevent costly mistakes, this framework provides a comprehensive roadmap for scaling profitably.Brown shares compelling stories from his experience working with over 450 businesses, including nearly hiring an unnecessary $75,000 attorney based on an emotional reaction rather than reviewing the actual data. He explains why maintaining proper financial ratios (like the "rule of thirds") is critical for profitability and how differentiating your marketing prevents the race-to-the-bottom price competition that kills margins. His example of the divorce attorney whose ad asked "Is he sleeping with her right now?" perfectly illustrates how breaking convention can dramatically improve results.Whether you're just starting out or looking to take your established business to new heights, Brown's practical advice on escaping "the weeds" of day-to-day operations, avoiding emotional decision-making, and thinking bigger will transform your approach to business building. Ready for consistent 35-40% annual growth while maintaining profitability? The answers are waiting in this must-listen episode. Get James's free book "Top 10 Mistakes That Will Destroy Your Business" and schedule a complimentary 30-minute discovery call at businessacceleratorinstitute.com/scalingpeople.

Jul 16, 2025 • 23min
Your Board Can Make or Break Your Company's Growth with Keith Dorsey
Send us a textBoards have the power to transform your company's trajectory, but founders often struggle to leverage them effectively. Dr. Keith Dorsey, author of "The Boardroom Journey" and boardroom expert with experience spanning military service, corporate leadership, and academic research, joins Gwyneth Beaver-Crary to decode what truly makes a high-functioning board.Drawing from his experience serving on five different boards and his doctorate research on corporate governance, Dr. Dorsey dismantles the common founder mindset that views boards as obstacles rather than assets. He outlines the three critical functions boards should serve: management support, advisory service, and governance oversight. The most effective boards operate with a "noses in, fingers out" philosophy—asking thought-provoking questions without micromanaging operations.Beyond structure and function, this conversation tackles the often-overlooked importance of board composition. Traditional approaches focused on filling seats with familiar faces and fellow CEOs create dangerous echo chambers. Instead, Dr. Dorsey advocates for cognitive diversity and strategic alignment, explaining how to assess both visible skills (the 10% above the iceberg) and underlying competencies (the 90% below). His practical advice on conducting board assessments and facilitating difficult transitions offers founders a roadmap for building boards that evolve alongside their companies.Perhaps most valuable is Dr. Dorsey's guidance on vulnerability in board interactions. By sharing "the good, bad, and ugly" rather than carefully orchestrating presentations, founders can transform board meetings from obligatory check-ins to powerful strategic sessions that genuinely accelerate growth. Ready to stop dreading your board meetings and start leveraging them as true assets? This episode provides the blueprint you need.Looking to strengthen your board or find your place in the boardroom? Connect with Dr. Dorsey at boardroomjourney.com or check out his book to continue your boardroom journey.

Jul 8, 2025 • 25min
The Membership Model: Growth Strategies and Pitfalls with Dominique Waples
Send us a textWhat happens when businesses truly prioritize people over profits? Is it sustainable? Or just idealistic thinking? Dominique Waples, CEO of Restore Medical Spa, dispels the myth that successful scaling requires putting revenue before relationships."Customers are people, employees are people, vendors are people. If you don't understand people, you don't understand business." This guiding philosophy has helped Dominique build a thriving multi-location medical spa over 13 years, but not without significant challenges along the way.The conversation delves into the reality that scaling with a people-first approach is "the long game" – requiring patience, persistence, and significant upfront investment. We explore the post-pandemic reality where employees bring their whole selves to work, and how leaders must balance genuine empathy with business requirements.Dominique vulnerably shares a cautionary tale about how her wildly popular membership program nearly bankrupted her business due to a critical pricing mistake. Despite an incredible 85% conversion rate, they were losing money on every transaction by restricting benefits to their least profitable service. This led to a powerful realization: "Memberships aren't speedboats; they're cruise ships – seemingly small adjustments can have massive impacts."For entrepreneurs considering membership models, Dominique offers invaluable guidance on proper pricing (hint: whatever you think you should charge, add 20%), simplifying options (no more than three tiers), and the benefits of creating a negative cash flow cycle where customers fund operations. She also reveals how personality assessment tools transformed her ability to place team members in roles they naturally excel in and enjoy.Have you considered how a people-first approach might transform your business growth? Share your experiences or questions in the comments and subscribe for more insights on sustainable scaling strategies!

Jun 25, 2025 • 23min
Your business is either a star or it's struggling - learn why with Perry Marshall
Send us a textWant to build a business moat so powerful competitors can't touch you—without the headache of chasing VC funding? Perry Marshall reveals a game-changing approach to market dominance that's hiding in plain sight.Marshall, author of "80-20 Sales and Marketing," introduces us to what he calls "Network Effect for Mere Mortals"—the overlooked feedback loops that transform ordinary businesses into unstoppable forces. Through the story of a roofing company that systematically cultivated review velocity, Marshall demonstrates how simple flywheels create compounding advantages that make your competition irrelevant. The conversation takes a fascinating turn when Marshall unpacks the AI opportunity most entrepreneurs are missing. Forget using AI as a fancy search engine—the real goldmine lies in creating proprietary knowledge systems that continuously improve. The companies already building these systems aren't just more efficient; they're establishing moats that will become increasingly impenetrable as time goes on.Perhaps most valuable is Marshall's explanation of the "Star Principle," a forgotten business framework from 1960 that explains why most businesses struggle despite good execution. His blunt assessment—"If your market is not growing and you're not number one, your life sucks"—cuts through the noise of conventional business advice. As markets shift from 80-20 to 90-10 distribution online, positioning yourself among the vital 10% becomes even more critical.Ready to stop exhausting yourself chasing marketing fads and build something with lasting power instead? Visit perrymarshall.com/podcast for special resources including his book that will transform how you see business fundamentals forever.