Scaling With People

Gwenevere Crary
  • 5.0 (27)
  • MANAGEMENT
  • UPDATED WEEKLY

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!

  1. 4D AGO

    Why Most Branded Podcasts Fail Before Episode One with Roger Nairn

    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 marketing wallpaper and why “just start a podcast” is some of the worst advice founders and marketing teams hear. We get into:  Why trust is the real advantage of podcasting  What audiences actually connect with  The authenticity problem killing branded content  Why polished but safe conversations don’t retain listeners  How executive-focused podcasts drive thought leadership and pipeline  The metrics that matter beyond downloads  What listen-through rate reveals about audience engagement  How internal podcasts strengthen culture across hybrid teams  Where AI and video are changing podcast production and distribution Roger also explains why the best podcasts are designed with a clear business objective from day one, whether that’s recruiting, customer trust, brand authority, or long-term relationship building. If you’re a founder, operator, or marketing leader trying to create content that compounds instead of disappears, this episode is for you. Follow Scaling with People for more conversations on leadership, growth, systems, and building companies that scale without breaking. Support the show

    28 min

  2. MAY 13

    Premium Clients Don’t Buy Hype. They Buy Certainty with Esther Stewart

    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 Continel , who transitioned from Fortune 500 finance roles at Morgan Stanley and Merrill Lynch into building multi-five-figure monthly businesses using one focused offer and a disciplined acquisition system. We break down why low-ticket marketing tactics often fail in premium markets, how sophisticated buyers evaluate trust, and what founders get wrong when trying to move upmarket. Inside this episode:  Why “clients buy certainty” changes everything in high-ticket sales  The hidden pricing hesitation buyers can hear immediately  How to structure a premium offer starting with the outcome first  Why vague messaging kills conversions with sophisticated buyers  The difference between attention and actual buyer intent  A simple AI-assisted workflow for improving your messaging and emails  How premium funnels should guide trust, not pressure people  Why showing pricing earlier can improve qualified calls and show-up rates  What makes video sales letters actually convert premium buyers We also unpack the psychology behind premium positioning and why founders often sabotage conversions without realizing it. From unclear timelines to weak conviction in pricing, Esther explains how uncertainty quietly leaks into sales conversations and lowers trust. If you’re trying to attract better clients, increase high-ticket conversions, and build a premium offer people trust quickly, this episode gives you the framework. Follow Scaling with People for more conversations on leadership, growth, systems, and the people side of scaling a business. What’s the biggest place uncertainty is showing up in your sales process right now? Support the show

    28 min

  3. MAY 6

    Revenue Isn’t Your Problem. AI Is Exposing Your Broken Systems with Ali Manki

    Send us Fan Mail If you think revenue is your problem, you’re already behind. This is what happens to most companies: the pipeline finally clicks, deals start closing, and then everything behind the scenes begins to crack. Delivery slips. Hiring lags. Systems break under the weight of “success.” In this episode, we sit down with enterprise sales leader Ali Manki to unpack what actually drives scalable growth—and where most founders get it wrong. We break down: Why selling more doesn’t fix a broken system (it exposes it)How top performers earn C-suite trust through deep account alignmentThe hidden deal killer: wasting time on the wrong stakeholdersWhy overcomplicated proposals stall decisions and cost you revenueThen we go deeper into the part no one wants to talk about: operational efficiency. Because growth doesn’t fail in the pipeline—it fails in execution. We cover: Where companies quietly bleed money (tool sprawl, disconnected systems, manual handoffs)Why “more tools” usually means less clarityHow to simplify operations so growth actually sticksFinally, we get practical about AI in sales: Turning call transcripts into objective coaching toolsCutting follow-up time from hours to minutesWhere AI helps—and where human judgment still mattersIf your company is growing but starting to feel strained, this episode will show you why—and what to fix before it breaks. Follow Scaling with People for real conversations about what it actually takes to grow without losing control. And if this episode hits, share it with a founder who’s in the middle of it right now. Support the show

    33 min

  4. APR 29

    Your Growth Isn’t Broken. Your Marketing Is the Bottleneck with Tim Padgett

    Send us Fan Mail Founder-led growth works… until it doesn’t. Pipeline gets unpredictable. Hiring slows down. And suddenly, everything depends on the founder — their relationships, their credibility, their time. That’s not scale. That’s a bottleneck. In this episode, we break down what’s really happening when companies hit that wall with Tim Pat of Pepper Group, who has spent decades helping mid-sized and private equity-backed companies turn marketing into a real growth engine. We get specific about what changes as you move from $5M to $10M, and what it actually takes to reach $50M and beyond. Tim explains why marketing isn’t a support function — it’s the system that makes sales easier — and why adding more reps won’t solve a demand problem. We also unpack:  Why most companies underinvest in marketing at exactly the wrong time  How to treat marketing like an investment with clear ROI  The simple dashboards and metrics leaders actually trust  How to create early wins with messaging, A/B testing, video, and customer proof Then we go deeper into something most founders miss: brand doesn’t just impact revenue — it shapes who wants to work for you. A weak brand quietly repels great candidates. We break down how employer brand really works, why it can’t sit inside HR, and what it takes to build a culture and story that attracts both customers and talent. Tim shares practical next steps you can implement immediately:  Run a voice-of-customer survey  Upgrade your careers page  Let customers tell your story through proof and testimonials If your growth feels inconsistent or overly dependent on you, this episode will show you where to fix the system. Follow the show for more conversations on scaling with people, and share this with a founder who’s trying to make growth repeatable. Support the show

    35 min

  5. APR 22

    Your Team Isn’t the Problem. Your Leadership Is. with David Miller

    Send us Fan Mail The fastest way to stall a growing company isn’t bad strategy. It’s treating people like “soft stuff” and trusting the numbers to tell the whole story. In this episode, David Miller breaks down what actually compounds in small business growth—and why most founders avoid it. We get into the uncomfortable truth behind energy, trust, and culture, and how ignoring them quietly slows everything down. David shares the moment he realized pure grind wasn’t sustainable—and how shifting to energy management and mental discipline changed how he leads. We unpack his “inside-out leadership” approach, why busywork feels productive while killing momentum, and how taking control of your calendar protects the work that actually drives growth. On the people side, this gets even sharper. We talk about hiring and rewarding based on earned trust, using core values as a real operating system—not wall art—and how to spot early signs of culture breakdown before they cost you. David also explains how to quantify the true cost of a toxic employee—and why your best people won’t tolerate misalignment for long. From an investor lens, we go inside the signals that show up in the first 3 to 90 days, how outside capital changes team dynamics, and what it actually means to respect capital when you’re building for the long term. If you’re building a company where people—not just numbers—decide the outcome, this episode will change how you think about growth. Follow the show for more conversations on how founders actually scale without breaking—and share this with someone who’s feeling the pressure behind the scenes. Support the show

    31 min

  6. APR 15

    Your Business Isn’t Worth What You Think with Gregory Kovsky

    Send us Fan Mail You can build a great company and still leave millions on the table when it’s time to sell. In this episode, I sit down with Gregory Kovsky, President and CEO of International Businesas Associates, who has personally closed 300+ transactions. We break down what actually drives valuation, how deals really happen, and the quiet mistakes founders don’t realize they’re making until offers come in lower than expected. One of the biggest myths in business is that there’s a single “correct” valuation. There isn’t. The same company can sell for very different numbers depending on the buyer, the market, and how well your financial story holds up under scrutiny. We get into the real drivers that show up in diligence: Why documented systems and processes increase value How customer concentration can quietly kill your multiple What clean financials actually mean—and how messy books destroy trust fast The hidden cost of running personal expenses through the business or keeping revenue off the books This conversation also goes beyond the numbers. Selling a business isn’t just a transaction—it’s identity, responsibility, and transition. We talk about what happens after the deal, how to protect employees and customers, and how professionals run a confidential process using NDAs, financial vetting, and controlled outreach—especially in a world where AI makes it easier than ever to expose sensitive information. If you’re thinking about selling in the next 12–24 months, this episode will change how you prepare—and how much you walk away with. Follow the show for more conversations on how to scale with people without breaking your business. And if this episode hits, share it with a founder who’s building toward an exit. Support the show

    33 min

  7. APR 8

    AI Won’t Fix Your Messy Company. It Will Expose It Faster with Karen Zeigler

    Send us Fan Mail Most founders think AI will make their company faster. It will. But if your systems are messy, your workflows are unclear, and your team is running on workarounds, AI won’t fix that. It will amplify it. In this episode, we sit down with Karen Zeigler, CEO of HumanScore, to break down what actually happens when companies try to automate broken operations and why “faster” quickly becomes riskier if your business isn’t built to handle the speed. We get specific about what needs to be fixed before you touch AI:  The workflows that look good on paper but don’t reflect how work actually happens  Data silos that confuse even the smartest models  Hidden decision-making norms that quietly run your company Because here’s the reality:  AI doesn’t remove the need for strong leadership. It raises the standard. If your team is surviving on patches and workarounds, AI will scale every gap unless you redesign how your company actually operates. We also go deeper into what human-centered leadership really means in an AI-driven world. Not perks. Not programs. But fixing the real friction that slows teams down and drains execution. And we draw a clear line on what should stay human, no matter how advanced the tools get:  Critical thinking  Real connection  Creativity Karen frames this moment as a workplace reset. A shift as big as the printing press. One that can elevate people, if leaders stop managing through control and start co-creating how work gets done. If you’re:  Planning an AI rollout  Scaling operations that feel increasingly fragile  Trying to improve employee experience without losing performance This episode will challenge how you’re thinking about growth. Follow + Share If you’re building a company that needs to scale without breaking, follow the show so you don’t miss what’s next. And if this episode hit, share it with a founder or leader who’s about to “move faster” without fixing the foundation. Support the show

    25 min

  8. APR 1

    Merchandise Your Value with Joe Frankie III

    Send us Fan Mail Your leadership can be strong and still go unnoticed if you don’t know how to position it. That’s the battlefield we step into with Joe Frankie III, a former U.S. Army commander turned executive advisor who’s helped hundreds of executives, veterans, and students build a bridge to their next role. We talk about what separates leaders who quietly stall from leaders who compound trust, influence, and opportunity. We start with the basics that many leaders skip: you don’t become a great leader until you learn to be a great follower. From there we get concrete about servant leadership, “leadership by walking around,” and why the best leaders think of themselves as resource providers. We also dig into prioritization when everything is urgent, plus a memorable distinction that changes how you delegate: calculated risk versus gambling. Then we move into modern executive presence and personal branding on LinkedIn. Joe breaks down what it means to merchandise your IQ and EQ, why a resume is a black-and-white snapshot, and why your LinkedIn profile is the color portrait that does covert networking on your behalf. We get tactical on building influence without feeling salesy, writing your About section in first person, and the small trust signals that matter fast, including a professional headshot where people can see your eyes. Know more about Joe here: https://www.linkedin.com/in/joefrankieiii/ https://www.facebook.com/joefrankieiii/ https://x.com/JoeFrankieiii If you’re a founder, executive, or veteran translating your experience into the civilian market, this is a practical guide to being found, being understood, and being trusted. Subscribe, share this with a leader who needs it, and leave a review with the biggest change you’re making to your LinkedIn presence. Support the show

    34 min
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5
out of 5
27 Ratings

About

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!

Information

  • Creator
    Gwenevere Crary
  • Years Active
    2023 - 2026
  • Episodes
    134
  • Rating
    Clean
  • Copyright
    © 2026 Scaling With People
  • Show Website
    Scaling With People