Bold Business Podcast

Jess Dewell
  • 5.0 (26)
  • Management
  • 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. 1d ago

    The Art of Stepping Away: Building Systems That Let Your Business Thrive

    Stuck competing in a market where every company looks the same? In the pest control industry, where services can feel interchangeable, Tim Whitt built a business on 90% recurring revenue by mastering relationships, brand touch points, and the systems that keep them consistent. In this episode of the BOLD Business Podcast, Jess Dewell talks with Tim Whitt, Founder & CEO at Pied Piper Pest & Lawn, about how to step away from the daily operations of a 16-year-old business and trust the systems you've built. Tim shares how leveraging technology and AI in business improves customer experience, how customization of services gives customers real choices, and why delegating decisions, not just tasks, starts within your team. Strategic time management and intentionally designed business systems protect your unique selling proposition while letting you scale at a healthy rate. That's where lasting competitive advantage comes from. In this episode, you will discover: Why choosing a small-town location sped up community connections and early business momentum How moving your office away from daily operations creates space for focus and strategic thinking How AI-powered meeting notes and fewer recurring meetings improve efficiency without hurting communication Why quick, solution-focused calls beat long email chains for response time and problem-solving How blocking personal time and wellness breaks sustains leadership and models balance for your team Why delegating decisions, not just tasks, empowers your people and lets you step back How consistent reinvestment and paced expansion drive sustainable business growth Why not every investment pays off in dollars, and why goodwill and customer satisfaction still count How trust, intentionally given, becomes the foundation of smooth operations It is BOLD to step away from the daily operations of a 16-year-old business and trust the repeatable systems you've built. —---------  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 LinkedIn, Instagram or Red Direction website.

    The Art of Stepping Away: Building Systems That Let Your Business Thrive

  2. Oct 22

    Outdated Plans, Exhausted Teams: How to Regain Momentumand Navigate Market Volatility

    Stop out-hustling yesterday. Rigid roadmaps and endless checklists can keep your team busy on priorities the market has already left behind, and that's how burnout and operational drag take hold. The linear business growth trap is seductive because it feels productive, but it leaves you executing without business instinct. In this episode of the BOLD Business Podcast, Jess Dewell, Strategic Growth Advisor and host, shares how to evolve before it's too late. She draws on lessons from past guests Bob Rogers, Kim Bohr, Dr. Jennifer Berry, Alexis Sikorsky, and Tracy Holland, whose experiences show that real momentum comes from clarity of purpose, ruthless focus, and adaptability. This four-part journey covers breaking free from outdated roadmaps, finding your true north (your Red Direction), recalibrating exhausted teams, and building systems-led execution engines for scalable growth. In this episode, you will discover: Why perfect execution of the wrong plan can leave you outgrown by the market How to recognize when you're busy but not actually adapting Why experimentation beats rigid checklists when integrating AI and new technology When long-term plans need revision, and how to adjust without losing focus How to re-orient your organization around one purpose so everyone stays aligned Why open dialogue helps teams recalibrate before issues become bigger problems How reflecting on effort, not just outcomes, prevents team fatigue and decision-making exhaustion Why top talent and new tools let smaller teams achieve what used to take much larger ones Jess delivers the inspiration and practical tools you need to lead with confidence in uncertain times. It is BOLD to let go of outdated approaches and respond decisively to market volatility for competitive advantage. _____________ 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.

  3. Oct 15

    Unlock Progress: Identifying Resistance and Moving Beyond Comfort

    It's not a strategy problem. It's a comfort problem. Change feels welcome until it asks you to move into new territory, and then it can feel daunting, even when you've hired outside experts. Sometimes the stress and frustration around AI disruption, rising costs, and burnout grow big enough that change has to happen. Other times, the real issue is business resistance rooted in a future that isn't compelling enough to pull you forward. In this episode of It's Your Business, Christy Maxfield (President and CEO at Purpose First Advisors), Dean Barta (Founder and CEO at Barta Business Group), and Jess Dewell (Managing Partner and Growth Strategist at Red Direction) have a candid look at what keeps businesses stuck.  Together, they unpack the internal friction that slows change management efforts and how to bridge the gap between planning and execution one uncomfortable, necessary action at a time. In this episode, you will discover: Why uncommitted leaders stand aside and how that quietly erodes progress Why even well-made plans stall at the execution stage How unspoken issues and discomfort, not a lack of strategy, block momentum Why comparing past successes to current efforts creates new self-doubt How honest reflection and outside perspective move businesses from talk to action Why over-reliance on numbers and systems can overshadow culture and instinct How accountability becomes real through practice and clear agreements, not checklists Why someone who can't genuinely agree with the direction is free to move on Three Key Takeaways Single-Task Focus: Build momentum by focusing relentlessly on one core priority at a time. Compelling Vision: Drive people-led change by crafting a future so magnetic that it overcomes resistance. Action Despite Fear: Build mental toughness by taking decisive steps forward, even while acknowledging uncertainty, fear of failure, and fear of success. It is BOLD to name what's keeping you comfortable and take the next step anyway. —---- 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.

    Unlock Progress: Identifying Resistance and Moving Beyond Comfort

  4. Oct 8

    ENCORE: How to Perform Under Pressure Aligned with Your Goals

    Growth is uncomfortable. Amy Anderson didn't plan to become an entrepreneur—a divorce and two young children forced the decision. What she's built since then, scaling from two people to 20 while running a fully dispersed team, offers real lessons in performing under pressure while staying true to your values.  In this episode, Jess Dewell talks with Amy Anderson, Co-Founder at Wild Coffee Marketing, about how to build a culture of accountability that allows teams to perform under pressure and stay aligned with their goals. The real secret to their success is how they've built a high-performance culture internally and help clients do the same. You'll discover: ✓ Why culture is how you do your work, not what work you do ✓ How to scale a dispersed team and create connection without an office ✓ The power of specific KPIs for both clients and your team ✓ Why quarterly energy reviews matter more than annual performance reviews ✓ How to create rhythm in a remote culture—clarity breaks, precision scheduling, sacred meeting times ✓ Why sometimes contraction (raising prices, focusing on bigger clients) is the path to growth ✓ The "ugly duck" method for getting started on strategic work when perfectionism blocks you ✓ How to commit and hold on when you can't see the full path forward ✓ What it takes to perform under pressure: clarity on values, meaningful metrics, and a culture of contribution Amy shares how she made the intentional decision in 2017 to build a remote-first company so she could hire the best talent. She shares the systems and frameworks that keep a distributed team aligned and accountable. Most importantly, what performing under pressure actually requires: people who think critically, metrics that mean something, and a culture where contribution is expected. It is BOLD to strive for greatness through accountability—in your team, in your relationships with clients, and in the daily decisions about how you do your work. —--------------------------------- 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 Perform Under Pressure Aligned with Your Goals

  5. Oct 1

    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

  6. 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

  7. 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

  8. 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
See All (529)

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
    529
  • Rating
    Explicit
  • Copyright
    © Red Direction, LLC
  • Show Website
    Bold Business Podcast

You Might Also Like