Scaling With People

Send us Fan Mail Guest: Matthew Clare LinkedIn: https://ca.linkedin.com/in/matthewjclare Website: https://ujet.cx/ AI is changing customer service but automating more interactions doesn’t automatically mean better customer experiences or stronger business results. In this episode of Scaling with People , host Gwenevere Crary sits down with Matthew Clare, VP of Product Marketing at UJET and a custo...

Send us Fan Mail Guest: Sudeshna Sen LinkedIn: https://www.linkedin.com/in/sudeshnasen Website: https://joinpionyr.com/ What if the advice you’re following is actually slowing your business down? In this episode of Scaling with People, host Gwenevere Crary sits down with Sudeshna Sen, serial entrepreneur, tech veteran, and founder of Pionyr, a network supporting women founders from pre-seed throug...

Send us Fan Mail Guest: Amanda Lannert LinkedIn: https://www.linkedin.com/in/amandalannert Website: https://www.jellyvision.com/ Do you really need a technical background, millions in venture capital, or a rapidly growing headcount to build a successful tech company? Amanda Lannert, CEO of Jellyvision, challenges conventional startup wisdom. She helped transform a creative business into a profitab...

Send us Fan Mail Guest: Maximos Lih LinkedIn: https://www.linkedin.com/in/maximoslih What happens when the skills that built your company become the very things preventing it from scaling? In this episode of Scaling with People , Gwenevere Crary sits down with Maximos Lih , executive coach and founder of Embolden, whose experience recruiting engineering talent at Google and advising founders at Go...

Send us Fan Mail Revenue may look strong on paper—but if the cash isn't there when you need it, your business can still be in trouble. In this episode of Scaling with People , host Gwenevere Crary sits down with Elaine Bogart , fractional CFO and financial leadership advisor, to demystify the numbers founders need to understand before scaling. Together, they explore why revenue, profit, and c...

Send us Fan Mail Guest: Andrew Brooks LinkedIn: https://www.linkedin.com/in/andrewcarrollbrooks/ Website: https://contextual.io/ AI is everywhere. But are you actually using it to build a competitive advantage—or just adding another chatbot to the business? In this episode of Scaling with People , we sit down with Andrew Brooks , serial entrepreneur, multiple-time founder, and CEO of Contextual.io...

Send us Fan Mail How do you scale a business without losing control of quality, culture, or accountability? Brad Coleman knows the problem firsthand. A former NASCAR driver and longtime entrepreneur, Brad bought the driving school where he learned to drive and helped turn it into a growing franchise system. Today, Safeway Driving has expanded across multiple locations while keeping its focus on th...

Send us Fan Mail To celebrate the milestone 150th episode of Scaling with People , host Gwenevere Crary steps away from the standard interview format for a candid, executive-level conversation on the real business value of HR. Joined by long-time friend, mentor, and 25-year HR executive Trina White (Founder of Swift Arc Strategic), the two break down why treating HR as a cost center silently drain...

Send us Fan Mail Guest: Grace Tabib LinkedIn: https://www.linkedin.com/in/gracetabib/ Website: https://dupayme.com/ You closed the deal. You delivered the work. So why isn't the money in your bank account? In this episode of Scaling with People , Gwendaver Crury sits down with attorney and founder Grace Sabine to unpack one of the most overlooked threats to business growth: unpaid invoices ....

Send us Fan Mail Guest: Nick Avaria LinkedIn: https://www.linkedin.com/in/nickavaria/ Website: https://agencyacquisitions.io Your business can have a great strategy, strong leaders, and talented people—and still hit a growth ceiling. In this episode of Scaling with People , Nick Avaria explains why the missing middle —the layer between senior leadership and frontline employees—can quietly become t...

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 Pe...

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 t...

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 thi...

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 emot...

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 r...

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&apos...

Send us Fan Mail 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 stra...

Send us Fan Mail 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 bottlenec...

Send us Fan Mail 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 res...

Send us Fan Mail 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 w...

Send us Fan Mail Most founders don't realize they've become the biggest constraint on their company's growth until every decision, problem, and customer issue starts flowing back to them. In this episode, we sit down with CEO mentor Rajesh Nagjee to unpack the founder bottleneck—the hidden leadership trap that slows growth, overwhelms teams, and makes scaling feel harder with every...

Send us Fan Mail Most companies are approaching AI the wrong way. They buy new tools, experiment with prompts, and expect breakthrough results. Then they wonder why productivity barely moves and expensive AI initiatives quietly stall. In this episode, Ghazenfer Mansoor, CEO of Technology Rivers and author of Beyond the Download , explains why successful AI adoption has less to do with the latest t...

Send us Fan Mail Most companies don’t break because growth is happening too slowly. They break because the systems, roles, and leadership habits underneath the growth can’t handle the pressure. In this episode, we sit down with Brian Hinton to unpack what actually happens inside companies when scaling starts creating chaos instead of momentum. We talk about the hidden operational cracks that show...

Send us Fan Mail Most branded podcasts fail before episode one. Not because the audio is bad, but because there’s no strategy behind it. In this episode, we sit down with Roger Nairn, co-founder and CEO of Jar Podcast Solutions, whose team has built podcasts for brands like Amazon, Lululemon, RBC, Deloitte, and Wharton School. We break down what separates a strategic branded podcast from expensive...

Send us Fan Mail Most founders think they need more leads. What they actually need is more certainty. Premium buyers don’t choose the loudest brand. They choose the clearest one. And when your positioning, messaging, or offer structure creates confusion, high-ticket sales stall fast. In this episode, we sit down with Esther Stewart, founder of CottnOwl Agency, who transitioned from Fortune 500 fin...