Scaling With People

Hosted by Gwenevere Crary

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Episodes

147

Latest episode

Aug 2026

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EN-US

About the show

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!

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60 recent

August 19, 202629 min

How to Scale Without Becoming the Bottleneck with Jason Henneberry

Send us Fan Mail Guest: Jason Henneberry LinkedIn: https://www.linkedin.com/in/jasonhenneberry/ Website: dependencydesign.com Your Business Shouldn’t Depend on You: How to Scale Without Becoming the Bottleneck Growth is supposed to make your business stronger—but what happens when every new client, employee, decision, and problem makes the business feel heavier ? In this episode of Scaling with People , Gwenevere Crary sits down with Jason Henneberry, entrepreneur and author of Dependency Design , to unpack one of the most common—and often invisible—problems facing growing businesses: Founder dependency. You may think you're leading by stepping in to solve problems. But every time you become the person who fixes what goes wrong, your business can learn that it can't operate without you . Jason shares how to recognize that pattern, why it can damage both your business and your culture, and what founders and leaders can do to build organizations that don't depend on heroic intervention. In this episode, you'll learn: Why successful growth can actually make a business feel heavier The difference between handing off tasks and handing off responsibility How founders accidentally become the "system" their business depends on Why stepping in to save the day can undermine employee confidence, innovation, and morale The four areas where dependency commonly appears: revenue, fulfillment, operations/process, and decision-making The different types of dependency that can exist within each area How to recognize accidental dependency versus intentionally designed dependency Why frustration is one of the best signals that a dependency problem exists How to identify where a problem belongs within your business Why SOPs and processes matter before you hire The difference between progress and transition —and why true accountability is harder to delegate How leaders can stop solving every problem and instead help their teams develop judgment How AI can help founders think through problems, ask better questions, and identify hidden dependencies The biggest belief about scaling that Jason thinks founders have completely wrong A powerful question for founders When something lands on your desk and your first reaction is: "Why is this back on me?" Don't just solve it. Look at it. That frustration may be a signal that your business has developed a dependency on you. The goal isn't to eliminate dependency. Every business depends on people, processes, systems, and outside relationships. The goal is to make those dependencies intentional by design rather than accidental by default. About Jason Henneberry Jason Henneberry is an entrepreneur in the residential real estate finance industry who has experienced the journey from solo operator to building a substantial organization supporting approximately 600 mortgage agents and teams across Canada. His book, Dependency Design , explores how businesses can identify and intentionally design the dependencies that allow them to scale without becoming overly reliant on their founder or individual leaders. Learn more and download the book at dependencydesign.com . About Scaling with People Scaling with People is your weekly playbook for turning chaos into compounding growth. Host Gwenevere Crary, executive advisor and fractional CHRO at Guide to HR, goes under the hood with founders and battle-tested experts across people, leadership, sales, marketing, operations, finance, product, and technology. No fluff. Just practical strategies, systems, and lessons you can put to work as you scale. Scale isn't just about speed. It's about people. Learn more at guide2hr.com . Support the show

August 12, 202627 min

Why You're Making More Money But Not Getting Richer with Ethan Heisey

Send us Fan Mail Guest: Ethan Heisey LinkedIn: https://www.linkedin.com/in/ethan-heisey-atlanta/ Website: https://ethanheisey.com/ Every founder wants to grow revenue—but what if the fastest way to build wealth isn't making more money? In this episode of Scaling with People , Gwenevere Crary sits down with tax strategist Ethan Heisey to uncover why many business owners pay far more in taxes than they legally need to—and how proactive tax planning can become one of the most powerful growth strategies in your business. Instead of treating taxes as an annual chore, Ethan explains how founders can make tax strategy part of their year-round financial plan, helping them keep more capital to reinvest into growth. In this episode, you'll learn: • Why tax planning should happen long before April • The difference between tax preparation and tax mitigation • When traditional deductions stop being enough • How high-income founders can legally reduce their tax burden • Why your advisor team can have a bigger impact on your wealth than your investments • How to evaluate whether your CPA is helping you grow—or simply filing paperwork • Practical next steps founders can take over the next 30 days If you're growing your business but wondering why your bank account isn't growing at the same pace, this conversation will change how you think about taxes, advisors, and long-term wealth. Key Takeaway: The best founders don't just earn more—they structure their business so they keep more of what they earn. Connect with Scaling with People Follow the show for weekly conversations with founders and experts on leadership, systems, AI, operations, finance, and the people strategies that help companies scale without breaking. If this episode helped you, share it with another founder who's working hard but wants to keep more of the wealth they're creating. Support the show

August 5, 202632 min

Your Leadership Isn't Breaking Trust. Your Communication Is with Kim Bohr

Send us Fan Mail Guest: Kim Bohr LinkedIn: https://www.linkedin.com/in/kimbohr/ Website: https://sparkeffect.com/ Your employees aren't resisting change. They're resisting uncertainty. Most founders think trust is something you either have or you don't. The reality? Trust is a measurable business asset—and one of the fastest things to disappear when communication breaks down. In this episode of Scaling with People , Kim Bohr, CEO of Spark Effect, explains why AI isn't the real threat to your culture. Poor leadership during change is. We unpack why employees disengage long before they resign, how leaders unknowingly create low-trust environments, and the practical frameworks that help organizations navigate growth, AI adoption, and disruption without losing their people. If you're scaling a company, implementing AI, or leading through uncertainty, this conversation will help you protect the one asset every growing business depends on: trust. In this episode you'll learn: Why trust directly impacts retention, revenue, and business performance The communication mistakes that quietly destroy culture How AI exposes weak leadership instead of causing it The warning signs that trust is eroding before employees leave A simple framework for leading change without creating fear Why founders should measure trust like any other business KPI Practical ways to rebuild trust after it's been damaged Three actions leaders can implement this week to strengthen trust across their teams Key Takeaway People don't leave because change happens. They leave when leaders fail to explain why the change matters, what it means for them, and how they'll be supported through it. Trust isn't soft. It's a competitive advantage—and one of the most valuable growth levers inside your business. If this episode helped you... Follow Scaling with People so you never miss weekly playbooks on scaling your company through better leadership, smarter systems, AI, and people strategies. Know another founder or executive leading through rapid growth? Share this episode with them—they'll thank you later. Support the show

July 29, 202629 min

Your Leadership Team Doesn't Have a Strategy Problem. It Has a Language Problem with Randy Lyman

Send us Fan Mail Guest: Randy Lyman LinkedIn: https://www.linkedin.com/in/iamrandylyman/ Website: https://randylyman.com/ Most founders think their biggest growth challenge is strategy. Randy Lyman says it's something far less obvious. After building multiple eight-figure companies, Randy realized that the biggest constraint on growth wasn't sales, marketing, or execution—it was the emotional patterns driving leadership decisions. In this episode of Scaling with People , host Guinevere Curry sits down with Randy to explore how leaders unknowingly create cultures that either accelerate growth or quietly hold it back. You'll learn why blame destroys performance, how psychological safety fuels innovation, and why the best leaders balance accountability with empathy. Randy also shares practical habits any founder can implement immediately to build stronger teams and better business outcomes. In this episode, you'll learn: Why leadership—not strategy—is often the real bottleneck to growth The three things every employee needs before they'll perform at their best How blame quietly erodes trust, innovation, and profits Why praise is one of the highest-return leadership tools you can use Practical ways to become a better listener and create stronger teams How emotional patterns affect company culture and business performance Why taking ownership builds credibility and trust faster than assigning blame The balance between logic, discipline, empathy, and collaboration that separates good leaders from great ones Memorable Quotes "People drive the numbers. Numbers don't drive people.""I always give credit for success and take the blame for failure.""When people know you believe in them, they show up as the best version of themselves." About Randy Lyman Randy Lyman is a physicist, entrepreneur, leadership coach, and the author of The Third Element . After building multiple eight-figure companies, he developed a leadership philosophy that combines business strategy with emotional intelligence to help leaders create healthier cultures, stronger teams, and more sustainable growth. Connect with Randy 🌐 Website: randylyman.com If you're a founder, CEO, or executive trying to scale without burning out your team—or yourself—this episode will challenge how you think about leadership and give you practical ways to build a company people genuinely want to be part of. If you enjoyed this conversation, follow Scaling with People for weekly conversations with founders and operators sharing practical strategies for building companies that grow through people, systems, and leadership—not chaos. Support the show

July 22, 202628 min

Your Leadership Team Doesn't Have a Strategy Problem. It Has a Language Problem with Mike Damphousse

Send us Fan Mail Guest: Mike Damphousse LinkedIn: https://www.linkedin.com/in/damphoux Website: https://www.categorydesignadvisors.com/ Most companies don't fail because of bad strategy. They fail because every executive is telling a different story. Sales has one message. Marketing has another. Product builds toward something different. HR hires for a vision no one can clearly explain. The result? Growth slows, execution gets messy, and leadership spends more time aligning than building. In this episode of Scaling with People , host Gwenevere Crary sits down with serial entrepreneur, investor, and co-author of The Category Creation Formula , Mike Damphousse , to explore why leadership alignment starts with language—not another strategic planning session. You'll learn: Why leadership misalignment quietly kills growth long before it shows up in revenue The "airplane pitch" every CEO should use to test whether their executive team is truly aligned Why category-leading companies focus on defining markets instead of chasing competitors How to evolve your company's positioning without disrupting what's already working Why sales, marketing, and product teams must speak the same language to accelerate growth The balance sheet metric founders should pay more attention to when measuring long-term value If your leadership team feels busy but disconnected, this conversation will help you identify the warning signs before they become expensive. Key Takeaway: Scaling isn't just about having the right strategy. It's about ensuring every leader can clearly communicate the same vision. If you enjoyed this episode, follow Scaling with People for weekly conversations with founders and experts who share practical strategies for scaling companies through stronger leadership, smarter systems, and better people practices. Support the show

July 15, 202626 min

The Financial Lies Founders Tell Themselves with Chris Everett

Send us Fan Mail Guest: Chris Everett LinkedIn: https://www.linkedin.com/in/chris-everett-a534174/ Website: https://everettwealthsolutions.com/ Most founders obsess over business metrics but rarely apply the same discipline to their personal finances. Instead, they make decisions based on stories: "My exit will take care of it." "Next year will be my breakthrough." "I'll deal with it later." Those assumptions can quietly cost hundreds of thousands of dollars over a lifetime. In this episode of Scaling with People , fiduciary financial planner Chris Everett , founder of Everett Wealth Solutions, explains why intelligent entrepreneurs often make emotional money decisions—and how to build a financial plan grounded in reality instead of hope. We explore why your earliest beliefs about money still influence your decisions today, how identity can drive unnecessary spending, and why many founders unknowingly take risks that leave their families and businesses exposed. Chris also challenges popular financial advice that isn't always right for entrepreneurs, including the 4% rule, maxing out a 401(k), and defaulting to a 529 plan. You'll also learn why tax planning, beneficiary designations, insurance, and asset protection deserve as much attention as your investment portfolio—and the simple exercise you can do this week to uncover one of the biggest gaps in your financial plan. In this episode, you'll learn: Why founders often make emotional—not rational—financial decisions What "financial future faking" is and how to avoid it How childhood beliefs shape your relationship with money Why your business should never be your retirement plan Common financial advice that doesn't fit many entrepreneurs The overlooked planning mistakes that can create major financial risk One simple review that could protect your family and your future If you're building a business, your personal financial strategy deserves the same intentionality as your growth strategy. This conversation will help you think differently about wealth, risk, and what financial security really means. Enjoyed this episode? Follow Scaling with People , leave a review, and share this conversation with another founder who's focused on building both a successful business and a secure future. Support the show

July 8, 202633 min

The Marketing Mistakes Costing Founders Customers with Lauren Schafer

Send us Fan Mail Guest: Lauren Schafer LinkedIn: https://www.linkedin.com/in/lauren-m-schafer/ Website: https://thelakehousedigital.com/podcasts/ If your marketing isn't generating qualified leads, the problem probably isn't your budget—it's your strategy. In this episode, Lauren Schafer shares why so many businesses waste money on marketing that never converts and what founders should do instead. From Google Ads and landing pages to LinkedIn, AI search, and employee advocacy, you'll learn practical strategies that help your business get found when buyers are actually ready to make a decision. In this episode, we discuss: • Why sending paid traffic to your homepage is one of the most expensive marketing mistakes you can make • How to improve Google Ads performance through better targeting, monitoring, and conversion-focused landing pages • The biggest reasons marketing campaigns fail—even with a healthy budget • How to build a consistent LinkedIn strategy that increases reach and credibility • Why employee advocacy often outperforms company pages on social media • How to turn your company culture into content that attracts both customers and top talent • What AI search tools like ChatGPT and Gemini look for when recommending businesses • The SEO strategies that still matter in an AI-driven world • If you had to cut your marketing budget in half, where you should—and shouldn't—spend it Whether you're a founder, CEO, or marketing leader, this conversation will help you stop wasting marketing dollars and start building a strategy that creates visibility, trust, and qualified leads. If you enjoyed this episode, follow Scaling with People , leave a review, and share it with another founder who wants to grow smarter—not just spend more. Support the show

July 1, 202631 min

The Trust Problem Founders Don't Know They're Creating with Patrick Farran

Send us Fan Mail Guest: Patrick Farran LinkedIn: https://www.linkedin.com/in/patrickfarran/ Website: https://adlucemgroup.com/ Trust is one of the most important assets in a growing company—and one of the easiest to damage without realizing it. This week, we sit down with Patrick Farran , founder of Ad Lucem Group, former SAS Institute consulting leader, and former Notre Dame MBA faculty member, to unpack what trust actually means inside a scaling organization and why it often becomes the hidden bottleneck to growth. Patrick breaks trust into four practical dimensions every leader can evaluate: Competence Integrity Transparency Psychological Safety We discuss why many founders treat trust as something people either have or don't have, when in reality it's built—or damaged—through hundreds of small leadership decisions. You'll learn how micromanagement silently communicates distrust, why asking for feedback on decisions you've already made can destroy credibility, and how unclear communication creates friction that leaders often mistake for performance problems. We also dive into one of the most overlooked leadership tools for scaling companies: the one-on-one meeting. Patrick shares how great leaders transform one-on-ones from status updates into conversations that build trust, accelerate development, and improve accountability. We explore practical frameworks for creating more meaningful discussions, using appreciation to strengthen relationships, and ending meetings with clear commitments that eliminate ambiguity. Know more here: https://www.amazon.com/Intentional-Executive-Purpose-Driven-Transform-Leadership-ebook/dp/B0GMLJLBDM/ref=sr_1_1?crid=3QS1NR59LV0M1&dib=eyJ2IjoiMSJ9.Jhq5N5umvndKN8x0AN7tZghw1VaeY4SIshkzMWZzjQLbLoajtc7ahIWrcSFNA-XsMofeUrD63RJT_e8nWmadJmdfkmKGoSFMuJ4kD5_K8wUZpJush54zOOI-AOJb4qJ4HmEzfskXjlh-AavDlq2hF1U8uXMYB6oNv7yDc8csAdaypKhLGYIQ6JM3G0I1M0eowW7J3CdbYLVLm9ivc0wdtUn_wXDukNN89WSl13umBv4.0apIumuubPDnK6t62OumnO7smlrlkalsgVFiKJ-vvSg&dib_tag=se&keywords=the+intentional+executive&qid=1782828622&sprefix=the+intentional+executive%2Caps%2C175&sr=8-1#averageCustomerReviewsAnchor In this episode, you'll learn: ✅ The four dimensions of trust every leader should measure ✅ Why micromanagement damages culture faster than most founders realize ✅ How leaders unintentionally lose credibility with their teams ✅ A simple framework for running more effective one-on-ones ✅ How trust impacts accountability, performance, and execution ✅ Why culture is built through daily behaviors—not mission statements If you're building a company that needs to scale beyond constant founder oversight, this conversation offers practical strategies for creating stronger leaders, healthier teams, and a culture people actually want to be part of. Follow Scaling with People for more conversations on leadership, culture, and building companies that grow without breaking. Support the show

June 24, 202627 min

Leadership Isn't Charisma. It's Knowing Which Lever to Pull with Marissa McCourry

Send us Fan Mail Guest: Marissa McCourry LinkedIn: https://www.linkedin.com/in/marissamccourry/ Website: https://www.icf-coaching.org/mfluence/ Charisma gets too much credit and clarity gets ignored. We sit down with executive coach and leadership development expert Marissa McCourry to unpack what actually creates influence when the stakes are high: knowing which lever to pull, and doing it consistently when things feel fast, messy, and uncertain. We walk through Marissa’s “seven levers” framework, built from academic research, enterprise leadership development, and years of coaching Fortune 500 leaders. First, we get honest about what leadership is (and what it isn’t): not a title, not prescriptive authority, and not “having all the answers.” From there we dig into self-leadership levers like inner wisdom (calm and decision quality under pressure), values-based leadership (your moral compass in chaos), and strategic confidence (moving without perfect data and escaping analysis paralysis). Then we shift to leading others: your internal brand and the reality of what your team experiences day to day, plus how anonymous 360 feedback can surface the truth without eroding trust. We also make the case for emotional intelligence as the multiplier lever, because EQ determines your relational impact and whether people feel safe enough to speak up. Finally, we connect leadership to execution, including vocal precision in communication and the hidden strengths that are often sitting right under your nose. If you’re a founder, manager, or executive working on leadership development, executive presence, communication, and high-performance execution, this is a practical playbook you can apply immediately. Subscribe, share it with a leader who needs it, and leave a review with the lever you’re going to pull first. Support the show

June 17, 202626 min

Should You Raise Capital? What Growth Investors Really Look For with Isabelle Tashima

Send us Fan Mail Guest: Isabelle Tashima LinkedIn: https://www.linkedin.com/in/isabelle-tashima-780065135/ Website: https://www.volitioncapital.com/ Most founders spend too much time asking how to raise capital and not enough time asking whether they should raise at all. In this episode, I sit down with Isabelle Tashima from Volition Capital to unpack one of the most misunderstood topics in startup growth: growth equity. We break down what growth equity actually is, how it differs from private equity and venture capital, and what founders need to know before taking outside investment. Isabelle explains why capital should accelerate a business that's already working—not fix one that isn't. We discuss the signals growth investors look for, how founders should think about timing a raise, and why maintaining control is often less about ownership percentages and more about choosing the right partner. We also dive into what makes a company truly investable: • Repeatable and scalable revenue growth • Strong unit economics • Customer retention and expansion • Clear go-to-market execution • The ability to explain growth drivers beyond headline metrics And, of course, we tackle AI. Isabelle shares why simply saying "we use AI" is no longer a differentiator, how AI is changing capital efficiency for growing companies, and the question every founder should ask: "If the underlying AI model became a commodity tomorrow, would your business still have an advantage?" In this episode, you'll learn: ✓ When growth capital makes sense—and when it doesn't ✓ How investors evaluate founder-led businesses ✓ What separates investable companies from the rest ✓ How to think about ownership, control, and long-term partnerships ✓ Why AI alone won't create a durable competitive advantage Whether you're considering raising capital, staying bootstrapped, or preparing for future investor conversations, this episode provides a practical framework for making better growth decisions. Follow Scaling with People for more conversations on building companies that scale without breaking. Support the show