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

    ENCORE: Best Leaders Add Value to Their Team and Business

    Your commitment to yourself determines everything else. Most leaders show up for their clients and team with unwavering dedication—yet struggle to honor the same promises they make to themselves. This gap is where potential goes to die. In this episode, Jess Dewell talks with Paul D. Casey, Coach and Author at Growing Forward Services, about why reflection, intentional decision-making, and personal accountability are the foundation of massive business growth. Intentionally adding value—to your business, your team, your clients—starts with a non-negotiable commitment to yourself. When you know how you want to show up, when you have clear filters for the opportunities you pursue, and when you pause regularly to assess what's working, everything shifts. The discipline of reflection separates leaders who chase shiny objects from those who build lasting momentum. And the secret? It's not about having more time. It's about using the time you have with intention, asking yourself the hard questions, and knowing when things need to end so growth can begin. In this episode, you'll discover: ✓ Why your commitment to yourself directly impacts how you show up for others ✓ The power of the "Big Three" daily goals and why this framework transforms overwhelm into clarity ✓ How the Four Tendencies assessment reveals why you succeed with external commitments but struggle with personal ones ✓ The relationship between your health, relationships, and business success—and why they're connected ✓ How to overcome fear with intentional action and a growth mindset ✓ Why "supposed tos" pull you off-track and how to reclaim how you want to actually show up ✓ The critical filters to assess which opportunities are worth your time right now ✓ Why asking yourself difficult questions before asking them of your team creates better leadership ✓ How the Personal Retreat framework turns reflection into discerned decisions and real results ✓ The discipline of knowing when things need to end so you can move forward The depth of your reflection determines the quality of your decisions. Leaders who build breakthrough growth aren't chasing more opportunities—they're getting clearer about which ones matter most. They're asking themselves hard questions. They're pausing to celebrate wins. They're using solitude and structure to access their best thinking. It is BOLD to dedicate time to personal reflection, to commit to yourself the way you commit to others, and to let the discipline of intentionality guide your business forward. —--------- 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.

    ENCORE: Best Leaders Add Value to Their Team and Business

  2. Sep 24

    How Business Instinct and Routine Drive Strategic Success in Scaling

    Your growth strategy is already outdated. That's not a failure — it's a reality. In this episode, Jess Dewell talks with John Sansoucie, CEO at CogNet, about what it takes to scale from startup to enterprise while staying aligned with a market that never stops changing. CogNet grew 600x. Along the way, John learned that the most dangerous assumption leaders make is thinking their strategy is static. Modern leadership isn't about having all the answers — it's about removing barriers, supporting your team, and adapting fast enough to keep pace with your market. That requires both Business Instinct and disciplined Routine. The challenge of scaling isn't just about technology or headcount. It's about building a culture where people trust their instincts, where experimentation is embraced, and where strategic pauses are valued as much as rapid growth. John shares insider lessons on evolving your tech stack, shifting from people-based to technology-based value propositions, and pacing growth to match your internal capabilities — not your ambitions. What you will discover in this episode: Why scaling from 67 to 600 employees requires upgrading leadership and formalizing practices How to balance autonomy, structure, and security when integrating AI and new technology solutions Why some teams thrive with permission to experiment — and why traditional IT gatekeeping can slow innovation The critical shift from charging for people to charging for technology and process improvements How to find the right pace of change — balancing urgency with the practical realities of execution Why client-focused operations demand adaptability and incremental improvements matter more than perfect solutions How cultivating experimentation and resilience in your workplace drives real innovation Why failing in pursuit of progress is a key learning tool for individuals and the company The importance of strategic pauses: scaling too quickly without infrastructure strains your business How to pace organizational growth to align with your internal readiness, not just market opportunity Why Business Instinct matters more than ever — real critical thinking is required in every role today How turning your strategic engagement cadence into routine is the precursor to sustainable success Getting comfortable with "no" might be your most profitable decision ever It is BOLD to declare to your team that staying true to your company's Growth Strategy means uncomfortable acknowledgment that your current strategy is already changing. The leaders who thrive aren't clinging to yesterday's plans — they're building the systems and culture to evolve intelligently, instinctively, and intentionally. If you're a CEO, operations leader, or scaling entrepreneur navigating rapid growth while trying to keep your team aligned and your systems stable, this conversation 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.

    How Business Instinct and Routine Drive Strategic Success in Scaling

  3. Sep 17

    How Self-Awareness and Mindset Fuel Bold Moves in Business

    Intentionally investing in your own and your team's personal brand is the single most powerful advantage to scale your company—especially during the high pressure and rapid change you face today. In this episode, Jess Dewell talks with Anne Candido and April Martini, Co-Founders at ForthRight People, about how self-awareness fuels BOLD moves in business and how aligning behaviors with your truest self creates real momentum, even as circumstances shift. Achieving big ambitions requires being bold, vulnerable, and taking responsibility for shaping perceptions and building supportive relationships. It's more important than ever for leaders and managers to show up authentically and harness your unique strengths. From this place of authenticity, you begin to be intentional about cultivating the experience others have of you—specifically, the way you want to be known. The key isn't adopting an external persona; it's embracing and expressing who you actually are, because that's where trust, influence, and lasting relationships are built. In this episode, you will discover: ✓ Why authenticity—not external personas—is the foundation of successful personal branding amidst competition and constant change ✓ How self-awareness and situational awareness enable you to intentionally manage how you show up and are perceived ✓ Why core beliefs rarely change, but behaviors and presentation can be strategically managed ✓ The critical disconnect between organizational values and individual interpretations that blocks achievement ✓ How clear definitions and ongoing dialogue align values across leadership, management, and employees ✓ Why slowing down to intentionally invest in foundational work creates faster, more effective future results ✓ How to manage organizational demands by setting boundaries and having honest conversations about priorities ✓ The importance of taking the first step—however small—to improve mindset and kick-start transformation ✓ Why overextending empathy drains energy and how maintaining emotional boundaries increases your effectiveness ✓ How managing trust issues begins with understanding the experience gap between stated values and lived experience It is BOLD to prioritize and actively embody your personal brand despite challenges, creating empowered authenticity and inspiring transformation in those around you. —--------- 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.

    How Self-Awareness and Mindset Fuel Bold Moves in Business

  4. Sep 10

    Deep Story, One Objective: The Secret to BOLD Brands

    Find out if your brand is built to last — or just chasing the next trend. Thinking with a longer horizon (even 20 years!) is the edge your business needs to withstand today's constant change. In this episode, Jess Dewell talks with Bob Rogers, Founder at BRC Imagination Arts and Author of "Deep Story A Masterclass in Experiential Story Making," about how practicing ruthless focus around one objective is what separates BOLD brands from the rest. There is an art to the discipline of editing and removing all except the most essential elements from a project. This includes planning for where you expect the future to be going, and recognizing that true hospitality is helping people find the magic within themselves. The emotional heart of your brand and the people you serve is a timeless element, and designing experiences that speak to that will perform better and last years to decades. In this episode, you will discover: Why the first step is determining your objective before any ideas or task lists are made (Don't skip this step. Ever!) How reciprocal kindness and emotional experience create meaningful brand experiences that endure Why lasting transformational experiences require a precise vision for your desired outcome How to avoid fuzzy language and instead articulate specific, observable outcomes Why people make decisions with their hearts first — and how storytelling is your primary lever How authentic hospitality places the focus on your guest's journey, not your expertise The power of designing experiences that empower participants to discover new capabilities Why building trust through partnership and collaboration is essential for transformational change How to claim your informed intuition and listen to it Why you must be focused to the point of ruthlessness — there can only be ONE objective It is BOLD to let go of linear planning and instead practice focused, ruthless clarity around one objective. The secret of bold brands is their ability to connect to a shared emotional truth with their customers. When you lead with that truth and edit everything else away, you create experiences that last. --------------------   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.

    Deep Story, One Objective: The Secret to BOLD Brands

  5. Sep 3

    Rethinking Hustle: Why Brute Force Work Is Outdated in the Age of AI

    In the age of AI, the traditional concept of hustle and brute force work is becoming outdated. Jess Dewell talks with Duncan Brand, Author of Mind the Gap and Effectiveness Advisor, about why it is BOLD to build systems-led execution and make themselves obsolete in day-to-day operations.   Uncover the secret weapon top leaders use to break out of overwhelm, refocus priorities, and drive lasting achievement — without burning out. Your calendar is your biggest tool.   We all have the same amount of time in a day. Planning your week and maintaining a cadence maximize impact. So, if you choose to muster the courage to step back from daily operations, you can further adjust where you add the most value. The impact of communication style on asking "why" in organizations. The long-term importance of a people-centric approach in adopting AI. Adapting to work-life integration in a technology-driven world.   Duncan shares insights on the Golden Pause for big decisions, building your week around top priorities, and the three ways you will get in your own way and what to do about it. The discussion also covers prioritising weekly goals and personal passions for effectiveness; the value and practice of intentional listening; the significance of inner core values and self-awareness in leadership; and common leadership identity traps that affect delegation and execution.   In the era of AI, it is BOLD for a CEO to step back and trust a systems-led execution, making themselves obsolete in the day-to-day operations. Tune in to learn how to accelerate achievement towards your 36-month initiatives by leveraging the secret weapon of top leaders and rethinking the outdated concept of hustle in the age of AI. —--------- 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.

    Rethinking Hustle: Why Brute Force Work Is Outdated in the Age of AI

  6. Aug 27

    Building, Buying, and Scaling Businesses for Modern Entrepreneurs

    You hired the best team, invested in the latest tools, and built what looks like a scalable operation. And nothing changed. Not because your people aren't talented — but because you're still playing the wrong role. You're still doing work that someone else could do better. The future of scaling isn't about building bigger teams or buying the next tool. I''s about knowing yourself — truly knowing where you drive the most value. And what actually matters to scaling — your clarity on role, your willingness to learn constantly, your ability to attract complementary talent — has been invisible to most entrepreneurial playbooks for too long. Jess Dewell talks with Tracy Holland, Founder at InnerFifth and Goodwillbrands, on how entrepreneurs can stop trying to do everything and start building businesses designed around their greatest strengths. Tracy has scaled multiple businesses by knowing exactly what she does best — and what to delegate, buy, or hire for everything else. In this episode, you'll discover: Why talent is your greatest asset above capital — and how to attract and retain it without bloated payrolls. How continuous learning keeps you ahead — and what it actually means to learn something new every week. Why livestreaming and personal brand building matter across every industry — and how this directly impacts your bottom line. How to delegate everything except your core strength — and why this accelerates growth exponentially. Why your best role in the business might not be CEO — and how to recognize it. How structured operating agreements and the right partners prevent years of hardship and misalignment. When buying an existing business is faster than building from scratch. What women entrepreneurs actually need to scale — and why traditional business groups are missing the mark. It is BOLD to acknowledge and claim the clunkiness of learning the skills needed to scale. The entrepreneurs scaling successfully know exactly what only they can do — and they've built everything else around that clarity. They partner strategically based on integrity, not just enthusiasm. They invest in personal brands because they understand it's a business asset. Growth accelerates when you stop trying to be CEO, operator, salesperson, and strategist all at once. If your business feels stuck despite your hard work, if you're wondering whether you're in the right role, or if you're ready to scale by design, this conversation will show you what's possible. —--------- 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.

    Building, Buying, and Scaling Businesses for Modern Entrepreneurs

  7. Aug 20

    Eliminating Strategic Debt and Boosting Team Productivity

    Align your actions with desired business outcomes, even when it requires challenging current habits. In this episode, Jess Dewell talks with Chris McShanag, CEO and Founder at Virtual Teammate, about boldly confronting distraction debt and using growth levers to scale. He shares proven strategies that help owners and executives ditch low-value work, redeploy talent, and fuel business growth — while delivering real client results. Today it is necessary to actively shape your company because there are challenges you must face to create the future relevance of your business. Prioritizing impact, and ensuring you have time to think before taking action, guarantees you are designing a path forward that puts decision-making and execution responsibilities with the right people on your team. In this episode, you will discover: The evolution of distributed workforces and how virtual teams enable growth without expanding physical overhead Why client experience should be the focal point for all business processes How to design operations in reverse from the ideal client experience, not from internal processes The reality of AI adoption and how it augments work rather than replaces it How to free up skilled professionals from administrative tasks so they can focus on highest-value work Why managing energy is as important as managing systems The proven way to evaluate how you spend your time for maximum impact How to remove friction and get out of your own way  The power of undoing or ending processes that hold growth back Why clarity of roles and accountability — not location — are core to team effectiveness and scalable growth It is BOLD to confront your own strategic debt and leverage your current leadership to grow and scale.  Managing distraction debt directly impacts your ability to lead effectively and scale intentionally. By removing what doesn't serve your vision and empowering the right people with the right responsibilities, you create the foundation for sustainable growth and real business transformation.   —-----------------   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.

    Eliminating Strategic Debt and Boosting Team Productivity

  8. Aug 13

    Achieve More by Doing Less: Effective Processes and Smart Financial Choices

    Prepare for the worst, hope for the best. Scenario planning isn't just for financials. Whether markets drop or your business faces adversity, having thought about the worst-case lets you operate with confidence. In this episode, Jess Dewell talks with Jack Oujo, Founder at Oujo Wealth Strategies, about why it is BOLD to embrace the concept of less is more — especially in today's fast-changing world. The toughest leadership calls are often the ones we delay. Welcoming peer feedback and brutal self-assessment catapults businesses to top-tier success. Embracing worst-case scenarios in decision-making and strategic planning is necessary to navigate recessions, market crashes, and disruption. You'll discover: Why focusing on existing clients drives growth far more than chasing new ones How career transitions can open unexpected doors when you embrace curiosity and risk Why process and scenario planning outperform rigid sales goals How culture and non-financial aspects determine long-term business stability The confidence that comes from preparing for worst-case scenarios Why financial independence matters more than following buzzwords like "retirement" How internal insights often outweigh endless external meetings What it means to make decisions based on deeply held principles Success is determined by how you choose to use the extra time you have. What you choose to carry forward from your biggest learning experiences shapes how you take calculated risks and move forward with intention. Take this work and focus on your client experience for connection and retention through change. —--------- 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.

    Achieve More by Doing Less: Effective Processes and Smart Financial Choices
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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
    525
  • Rating
    Explicit
  • Copyright
    © Red Direction, LLC
  • Show Website
    Bold Business Podcast