Bold Business Podcast

Jess Dewell
  • 5.0 (26)
  • Management
  • Updated Weekly

The Voice of Bold Business Radio talks about skills to ask better questions, solve problems and take action. The result is effectively handling: tough situations; changing culture; adding new products or markets; setting goals; reviewing people; evaluating business; setting priorities; building strategy; and more.

  1. 2d ago

    Prioritize, Ship, Repeat: Mastering Efficiency and Team Happiness

    Your team is tired. Not because they're working hard — it's because nothing finishes. Projects linger. Code stays half-baked. Strategy documents gather dust. Trust frays. And the worst part? Nobody can name what's actually wrong. Because the real problem isn't the work itself. It's that half of it never ships. It just sits there, unfinished, invisible, draining energy from everyone who touches it. Efficiency isn't about doing more. It's about finishing what matters. Team happiness isn't a perk you add on — it's what happens when people see their work actually ship, when they're focused on one thing instead of scattered across ten, when they know their contribution landed. The resistance you're sensing isn't that your team doesn't want to move fast. It's that they can't see progress. Because progress isn't a milestone. It's evidence of successful, ongoing delivery. What creates capacity while making progress are small, iterative cycles so that goals remain relevant in disruptive environments. Making work visible can transform your organization's internal strengths into real competitive advantage. In this episode of the BOLD Business Podcast, Jess Dewell talks with Thanos Diacakis, CEO and Chief Troublemaker at Cosmic Teacups, about why the teams moving fastest aren't the ones chasing arbitrary milestones — they're the ones who learned to name what's unfinished and architect a resilient delivery system. In this episode, you'll discover: Why humility and questioning assumptions is foundational to progress. The power of constructive conflict in establishing shared language and driving innovation. Why premature standardization hinders innovation and adaptation. The critical importance of finishing work before moving to something new. How prioritizing completion and minimizing context switching improves efficiency and team happiness. The value of limiting focus to what truly matters most. Why naming discomfort directly enables honest problem-solving. The teams that scale fastest aren't the ones with the best plans. They're the ones who can see where work actually gets stuck and aren't afraid to name it. They've learned that conflict isn't dysfunction — it's how you surface what teams actually need. They've discovered that when people finish work and see it shipped, everything changes. Efficiency goes up. Happiness goes up. Energy returns because there's forward momentum. Thanos has spent years on the frontlines where this plays out every single day. He's seen what happens when leaders try to do everything themselves and what shifts when they instead create space for teams to own completion. He's watched rigid plans crumble and resilient delivery systems take their place. The lesson: stop chasing arbitrary milestones. Start shipping real work. If your team is stuck in half-finished mode, if you're wondering why efficiency initiatives aren't creating happiness, if momentum has stalled and you're unsure whether the problem is strategy or delivery, or if you're ready to move from managing chaos to architecting a system that lets teams actually finish what matters, this conversation will reorient what's possible. --------------------   If you want to identify business bottlenecks, the necessary skills, the initial actions to take, the expected milestones, and the priorities for achieving growth, try the "Growth Framework Reset" approach. This will help you keep learning and growing while working strategically on your business. --------------------   You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.

    Prioritize, Ship, Repeat: Mastering Efficiency and Team Happiness

  2. Jul 16

    Scaling Smart: Why Executive Bottlenecks Erode High-Growth Companies

    Growth plateaus aren't inevitable — they're a signal. In this episode, Jess Dewell, Growth Strategist at Red Direction and host of the BOLD Business Podcast, reveals why even high-performing CEOs and founders hit a ceiling and how to break through it. The cycle of hustle is real, but scaling with intention requires more than speed — it demands strategy, self-awareness, and the courage to evolve. Jess explores the hidden bottlenecks and comfort zones that sabotage teams, keep decisions reactive, and erode competitive advantage. What makes it BOLD: Being BOLD means transforming your proven business practices through Business Instinct — the fusion of data-driven logic, emotional intelligence, and intuitive leadership. It's the courage to step back, challenge what's working, and align your company with evolving markets before disruption forces your hand. What You'll Hear: Why strategies that built your business won't scale it further The 11 Resources for Dynamic Growth every leader needs How to develop your Business Instinct for smarter decisions Why action-first approaches outpace endless planning The power of combining logic, emotion, and gut instinct How living tools like SWOT keep your strategy nimble Why reflection and disengagement drive breakthrough clarity How the Driving Solutions Strategic Intensive helps you implement sustainable growth without overwhelm Learn how to unlock your team's next level of performance, command strategic clarity, and build lasting business relevance — without burning out. Perfect for: Founders, CEOs, and ambitious leaders ready to move beyond the hustle cycle and scale with intention.

    Scaling Smart: Why Executive Bottlenecks Erode High-Growth Companies

  3. Jul 9

    Leadership Transitions: From Change and Resistance to Resilient Teams

    The resistance your team is showing isn't about your direction. It's about being left out of the story. You have the vision. You have the answers. You know exactly where this needs to go. And that's precisely where you're losing them. Because a vision that lives only in your head isn't a company vision. It's a founder's private project. And teams don't sign up to be passengers in someone else's story. Leadership transitions aren't about pivoting strategy or restructuring org charts. They're about inviting your team into the narrative so they actually own the outcome. The resistance you're feeling? It's not a sign you need better answers. It's a sign you need better listeners, and you need to be one of them. Jess Dewell talks with Nellie Lester, Advisor at WS & Co. Advisory, on how founders can move from being the hero of the story to being the architect of collective success. Nellie has seen what happens when leaders try to control every answer and what shifts when they instead create space for others to step into their strengths. In this episode, you'll discover: Why your personal ambitions can actually create disconnects in your team, even when your intentions are good How founders accidentally hoard the company narrative and why that kills alignment The power of collective problem-solving during crisis, and why humility is a competitive advantage, not a weakness Why inclusive dialogue isn't a nice-to-have; it's how you prevent tunnel vision and build real ownership What to look for in hiring to prevent future friction: aligning on values before skills How to recognize when a role, relationship, or process has served its purpose, and why letting go is essential to growth The difference between being indispensable and building an indispensable organization The leaders navigating change successfully aren't the ones with all the answers locked in their heads. They're the ones who stepped back enough to see that everyone at the table builds the organizational story together. They invited strengths they didn't have. They admitted what they didn't know. They created space for others to lead. Resistance to change often isn't resistance to the direction, it's resistance to being excluded from shaping it. The teams that move through transitions with resilience aren't the ones that follow orders. They're the ones that co-create the path forward. That's the human side of leadership. That's what builds organizations that endure. If your team is stuck in resistance mode, if momentum has stalled and you're wondering whether the problem is the strategy or how it's being communicated, or if you're ready to move from managing everything yourself to leading a team that owns the outcome, this conversation will reorient what's possible. —--------- If you're ready to build the organizational foundation that supports real growth, check out the Business Base Camp Consultation designed for owners who need to do the right work and lead growth at the same time, building the processes and market clarity to move from management oversight to systems-led execution. --------------------   You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.

    Leadership Transitions: From Change and Resistance to Resilient Teams

  4. Jul 2

    CEO Confessions: Loneliness, Building the Right Team & Bold Growth

    You started your company because you were exactly what it needed. Then your company grew, and suddenly you became the problem. No one tells founders this part of the story — not in the highlight reels, not in the fundraising pitch decks, not until you're standing alone at 2 a.m. wondering if you're the one holding the business back. Scaling isn't just an operational challenge. It's a personal reckoning. The skills that got you here won't get you there. The team that was scrappy and loyal will need to be rebuilt. And the exhaustion you're feeling? That's not a weakness. That's a signal you're not supposed to ignore. Jess Dewell talks with Alexis Sikorsky, Founder at Sikorsky Consulting and KnightScale Partners, on the confessions founders rarely make and the hard truths about what it actually takes to scale. Alexis has walked founders through the $5-15 million inflection point — where self-transformation becomes non-negotiable, and the cost of staying the same exceeds the cost of changing. In this episode, you'll discover: Why founders risk becoming liabilities if they don't actively transform as the company scales The specific revenue milestone where this shift typically happens — and what to watch for Why trust must trump skills when building your leadership team — and what that actually means in practice How early team members who got you here often can't take you where you're going Why spending less is a more sustainable growth lever than obsessively raising more capital The power of saying no — and why declining work that isn't a mutual fit protects your reputation and runway How to recognize exhaustion as a founder signal, not a personal failure The friction that's actually necessary for real growth — and how to distinguish it from noise The founders scaling successfully aren't the ones chasing the next funding round or surrounding themselves with resume stars. They're the ones willing to get uncomfortable. They're the ones who looked in the mirror and changed. They're the ones who built leadership teams based on trust, not credentials. They controlled their burn. They said no more than they said yes. Loneliness in entrepreneurship is real. The pressure to do more, raise more, prove more — it's relentless. But the founders who make it through aren't the ones who pretend the exhaustion isn't there. They're the ones who claim it, get strategic about it, and use it as information instead of a weakness. If you're at that inflection point where something needs to shift, if you're wondering whether the problem is the team or you, or if you're feeling the weight of scaling in a way nobody prepared you for, this conversation will give you permission to get honest about what's actually required. —---------   If you want to identify business bottlenecks, the necessary skills, the initial actions to take, the expected milestones, and the priorities for achieving growth, try the "Growth Framework Reset" approach. This will help you to keep learning and growing while working strategically on your business.   --------------------   You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.

    CEO Confessions: Loneliness, Building the Right Team & Bold Growth

  5. Jun 25

    ENCORE: How To Avoid The Hidden Costs Of Growing Your Business

    Are you your own biggest roadblock to success? In this episode, Jess Dewell (Managing Partner and Growth Strategist at Red Direction) , Christy Maxfield (President and CEO at Purpose First Advisors), and Dean Barta (Founder and CEO at Barta Business Group, have a candid conversation about what growth really looks like — and what it costs.   Growth isn't just about revenue. It means building infrastructure, developing talent, entering new markets, and making hard choices — planned and unplanned. But before any of that, it starts with mindset.   Your inner dialog has real-world consequences, and knowing where you're being held back — by external forces or by yourself — is the first step toward designing intentional action.   Together, Jess, Christy, and Dean explore:   How to stay with the problem when it shows up Why you don't need all the data — just the right data How tools like SWOT analysis can normalize smarter decision-making When and how to approach client diversification The power of starting with the end in mind How to let go of the stories holding you back   If you're ready to transform challenges into opportunities and build a business that is both successful and sustainable, this episode is for you.   -------------------   If you want to identify business bottlenecks, the necessary skills, the initial actions to take, the expected milestones, and the priorities for achieving growth, try the "Growth Framework Reset" approach. This will help you keep learning and growing while working strategically on your business.  --------------------   You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.

    ENCORE: How To Avoid The Hidden Costs Of Growing Your Business

  6. Jun 18

    Clarity, Fairness, and Care: The Secret to High Trust Organizations

    Here's what kills growth quietly: not bad strategy or tired teams, but leaders who stop showing up with intention. When you're busy, when uncertainty rises, when the pressure mounts — that's exactly when trust starts to leak. And by the time you notice, it's already become your biggest liability. Trust isn't an intangible value or a soft skill. It's measurable, concrete operational infrastructure. And when leadership is stretched thin, self-care gets deprioritized, and uncertainty becomes the norm, the organizations still standing are the ones who never let trust get blurry in the first place. Jess Dewell talks with Kim Bohr, CEO at SparkEffect, on how high-trust organizations outpace uncertainty and build the resilience that allows businesses to scale. Kim has seen what happens when managers are left to navigate change alone, and what it takes to rebuild credibility with teams that have grown skeptical of leadership. In this episode, you'll discover: Why continuous re-evaluation of systems and priorities isn't a luxury — it's how leaders stay credible and effective How trust between team members and self-trust are deeply connected and directly impact organizational performance Why measuring trust matters — it moves trust beyond concept and into actionable improvement The real cost of ignoring your own limits and energy — and how self-care directly affects your credibility with your team What transparency and fairness look like during organizational change — and why employees notice the gap between stated values and actions. How tailored leadership and adapted communication prevent misunderstandings and strengthen team alignment Why manager enablement isn't a side project — it's the primary strategic infrastructure for scaling trust The organizations winning when uncertainty rises aren't the ones with the most sophisticated systems or the largest budgets. They're the ones with trust and discipline. They resisted the pressure to chase every new initiative. They invested in their frontline managers. They built credibility through intention, not volume. Distrust in organizations is growing, and the companies feeling it most are the ones that prioritize tactical execution at the expense of people's investment. Trust is the competitive advantage that holds. And in a landscape increasingly driven by change and complexity, choosing to slow down and develop your managers is itself a bold business decision. If your organization's growth has plateaued, your team is reacting to changes instead of leading with strategy, or you're wondering whether your current manager development investment is actually moving the needle, this conversation will reorient your thinking. —--------- If you're ready to build the kind of organization that doesn't just survive uncertainty but leads through it, check out the Present Retreat, your weekly practice that reclaims executive bandwidth, sharpens business instinct, and replaces reactive goal chasing with strategic compounding, all with measurable reduction in decision-cycle time. --------------------   You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.

    Clarity, Fairness, and Care: The Secret to High Trust Organizations

  7. Jun 11

    Productive Struggle and Joyful Leadership: Redefining Success in Business

    What if your routines are quietly stifling your company's growth? In this episode of the BOLD Business Podcast, host Jess Dewell sits down with Dr. Jennifer Berry, CEO of SmartLab, to explore a rebellious mindset shift that disrupts burnout and drives fresh thinking in today's fast-changing business landscape.   Dr. Berry challenges the "go it alone" approach to leadership, making the case that lasting impact is built through collaboration, belonging, and the willingness to face discomfort together. From her Stop, Walk, and Think process to the power of tiny acts of rebellion, she offers practical ways to break mental ruts, spark innovation, and reconnect with what truly matters.   You'll walk away understanding how celebrating effort fuels both immediate momentum and long-term goals, why joy isn't forced positivity but a practice worth designing into your culture, and how productive struggle — for your team and your clients — is one of the boldest moves a leader can make.   In this episode: Why identity and self-worth get tangled up in workplace change — and how to navigate it How hands-on, project-based environments unlock natural curiosity and real growth Making KPIs flexible enough to reflect shifting goals without losing structure Reflection rituals that sharpen focus and reduce distraction How micro-changes in daily habits fuel bigger innovation Cultivating joy as a resilience strategy, not a feel-good afterthought   If you're ready to redefine success to include joy and productive struggle, this conversation is your starting point.   —---------   If you want to identify business bottlenecks, the necessary skills, the initial actions to take, the expected milestones, and the priorities for achieving growth, try the "Growth Framework Reset" approach. This will help you to keep learning and growing while working strategically on your business.   -------------------- You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.

    Productive Struggle and Joyful Leadership: Redefining Success in Business

  8. Jun 4

    Surviving Algorithm Shifts: Clear Messaging and Smart Advertising

    Most companies don't lose ground because their product weakens or their team stops working. They lose ground because the message drifted - gradually, quietly - while everyone was busy chasing the next platform update. A clear message isn't a marketing asset. It's operational infrastructure. And when algorithm shifts, shrinking social ROI, and an AI-saturated ad landscape all arrive at the same time, the companies still standing are the ones who never let the message get blurry in the first place. Jess Dewell talks with Rihab Abouzaki, Expert in GCC–US Advertising at This N That Communications, on advertising strategies that hold up when conditions change. She's seen what happens when businesses outsource their message clarity to whatever platform is trending, and what it takes to rebuild trust with audiences that have grown skeptical of everything digital. In this episode, you'll discover: Why a single, well-defined message consistently outperforms multi-channel complexity in advertising ROI What it actually means to choose the right medium — and why streaming TV is outpacing social platforms for authentic reach in the US market How to rebuild an advertising strategy when your current process has stalled or stopped producing results Why customers don't adapt as fast as AI-driven platforms expect them to, and how to use that gap to your advantage The cost of emotional attachment to your own ideas — and how daily testing without ego creates sustainable advertising performance How business seasonality should drive spending decisions, and why ignoring natural cycles drains budget without building momentum What starting from the desired result looks like in practice — and why reverse-engineering your strategy is the move most companies skip The businesses winning in today's advertising environment aren't the ones with the most sophisticated tools or the largest ad budgets. They're the ones with message discipline. They resisted the pressure to chase every algorithm update. They built credibility through consistency, not volume. Distrust in the online world is growing, and the companies feeling it most are the ones that chase reach at the expense of message. Clarity is the competitive advantage that holds. And in a landscape increasingly driven by automation and AI, choosing to prioritize human connection over algorithmic optimization is itself a bold business decision.  If your advertising results have plateaued, your team is reacting to platform changes instead of leading with strategy, or you're wondering whether the ROI on social spend is still worth defending, this conversation will reorient your thinking. —--------- If you're ready to build the kind of business that doesn't just survive uncertainty but leads through it, check out the Driving Solutions Strategic Intensive program, designed to support leadership teams through high-stakes strategic decisions.    -------------------- You can get in touch with Jess Dewell on Twitter, LinkedIn, or Red Direction website.

    Surviving Algorithm Shifts: Clear Messaging and Smart Advertising
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5
out of 5
26 Ratings

About

The Voice of Bold Business Radio talks about skills to ask better questions, solve problems and take action. The result is effectively handling: tough situations; changing culture; adding new products or markets; setting goals; reviewing people; evaluating business; setting priorities; building strategy; and more.

Information

  • Creator
    Jess Dewell
  • Years Active
    2017 - 2026
  • Episodes
    515
  • Rating
    Explicit
  • Copyright
    © Red Direction, LLC
  • Show Website
    Bold Business Podcast