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. Workplace Legal Issues Every Company Leader Needs to Know

    5d ago

    Workplace Legal Issues Every Company Leader Needs to Know

    Growing companies often sacrifice the foundation while chasing the finish line. Culture gets built later. HR systems get installed when problems surface. Employee protections feel like a luxury for bigger budgets. And somewhere in the scaling sprint, leaders realize they've created the perfect conditions for workplace disputes, legal exposure, and the very chaos they were trying to outrun.   But here's what separates companies that thrive from those that get blindsided: the ones who treat people's systems as core infrastructure from day one.   "It is BOLD to say that you are for the people and mean it." — Jesse Weinstein, Partner at Phillips and Associates, PLLC   Jess Dewell talks with Jesse Weinstein who has spent his career untangling the mess that happens when intention and practice split apart. From startups racing to scale to established organizations with public missions focused on inclusion, he's seen where the gaps appear — and what it costs to ignore them.   In this episode, you'll discover:   How rapid growth creates blind spots in oversight that invite misconduct and legal risk Why early investment in culture and communication systems prevents costly disputes later The role transparency and visible leadership play in building employee trust and accountability How misalignment between stated values and daily practices opens the door to reputation damage and lawsuits What proactive problem-solving looks like when you're under pressure to keep moving The strategic advantage of building strong internal channels before you desperately need them   The companies winning at scale aren't the ones outworking chaos — they're the ones who built systems that prevent it. They invested in culture when it felt optional. They made communication channels visible before crises forced their hand. They aligned their words with their actions. This episode isn't about compliance theater. It's about recognizing that your people, your culture, and your legal foundation are inseparable from your growth strategy.    When leadership commits to getting this right, the payoff is both immediate and compounding: reduced turnover, stronger collaboration, and the kind of organizational stability that actually accelerates scaling.   If you're building a company that's growing faster than your systems can keep up, or you're realizing that your internal practices don't match your external promises, this conversation is for you. —----------------- Ready to build the foundation that supports real growth? The Business Base Camp Consultation is 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. It's where strategy meets culture, and where sustainable scaling actually begins. —----------------- You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.

    39 min
  2. The Business Evolution Roadmap: Bridging the Gap from Here to There

    May 21

    The Business Evolution Roadmap: Bridging the Gap from Here to There

    If you picture your role two years from now, what would need to change? That's the question 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) explore in this It's Your Business episode. These three business advisors talk about the mindset shifts and practical moves that actually matter in the next 24 months. Whether you're running a boutique firm, scaling mid-market, or managing a larger operation, reducing operational friction and getting real-time visibility into your data is something you can influence right now. The conversation moves through three key areas: the Reality Audit (really owning where your business stands), Design 2+ Years Ahead (working with your existing productivity rhythms), and the Execution Bridge (how to stack priorities and actually move forward).  They talk about why perception often doesn't match reality, how conversation can feel like progress when it isn't, and what it takes to shift from talking about change to making it happen. Key Takeaways: Christy Maxfield: "Get all your butterflies flying in the same direction." Dean Barta: "Break down goals to be able to move forward." Jess Dewell: "Be courageous and make a shift in mindset to get to a large initiative 2 years from now." —----------------- Ready to build the foundation that supports real growth? The Business Base Camp Consultation is 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. It's where strategy meets culture, and where sustainable scaling actually begins. —----------------- You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.

    51 min
  3. Guiding Growth: How to Keep Your Team, Tech, and Strategy Relevant

    May 14

    Guiding Growth: How to Keep Your Team, Tech, and Strategy Relevant

    "Stamina is a trap." Most small business owners already know it. But knowing it and actually building a business that doesn't depend on your constant intervention are two very different things.   We've normalized the grind,  the packed schedule, the heroic push through chaos, the belief that if you just work harder, longer, the growth will come. And somewhere in all that muscling through, we stopped asking the more important question: are we doing the right work, or just a lot of it?   "If you are relying on your ability to outwork the chaos, you are already losing."   Jess Dewell, Growth Strategist at Red Direction and host of the BOLD Business Podcast, introduces the Business Basecamp framework, a three-part approach designed to get you off the plateau and back into the growth zone without burning out in the process.   What emerges isn't a productivity hack or a planning template. It's a rethinking of how leaders show up — moving from constant intervention to systems-led execution, from reacting to leading, from surviving the pace of change to setting it.   In this episode: Why reflection isn't looking backwards — it's the most strategic thing you can do right now How "distraction debt" quietly suffocates growth, and how to start paying it down The real reason smart leaders don't take action — and what to do instead How to protect your "core magic" as your business scales and your role shifts What strategic accountability actually looks like when chaos is the norm   "Growth isn't about doing more. It's about becoming a responsive decision maker."   This is one of those episodes that reframes the whole game, not by adding more to your plate, but by helping you finally work on the right things.   Jess also shares the 11 Essential Resources for Dynamic Growth, a free curated collection of podcasts and articles covering everything from mastering the Intentional Pause to building your own Present Retreat.    Designed for self-starters and lifelong learners, these are the actual tools Red Direction uses to help businesses break through their strategic ceilings. You can download it here.   It is BOLD to stop muscling through and build the foundation instead. This episode shows you how.   -------------------- You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.

    41 min
  4. ENCORE Mindfulness and Creativity: Unlock Your Business Potential

    May 7

    ENCORE Mindfulness and Creativity: Unlock Your Business Potential

    "Good ideas come to me easily." It sounds almost too simple. But what if your creativity isn't actually the problem - what if it's the way you've been trained to chase it?   We've built entire careers around productivity systems, packed calendars, and the belief that output is the measure of value. And somewhere in all that busyness, we lost the thing that actually drives innovation: the ability to slow down and let ideas find us.   "You're not going to get good ideas if you're running around on the hamster wheel with your hair on fire. They just don't have any place to be."   Jess Dewell brings together three practitioners who approach this problem from very different angles - Catherine Morgan (business consultant and transitions strategist), Claire Uncapher (intuitive life coach), and Dr. Janice Campbell (acupuncturist and somatic practitioner) - for a conversation that's equal parts practical and perspective-shifting.   What emerges isn't a case for self-care. It's a case of rebuilding your relationship with time itself. For trusting the pause. Recognizing that the traits you've spent years working around - the slowness, the tangential thinking, the need for space - might be exactly where your best ideas live.   In this episode Why your physical and internal environment shapes your output more than any strategy or tool How to run a 2-minute experiment this week that can crack open creative thinking The difference between self-care and mindfulness as a genuine business practice What it actually means to trust yourself - and why most of us were trained out of it early How to reframe the traits you see as weaknesses into your sharpest creative assets   "Mindfulness is life. Not just self-care." It's "the ultimate productivity hack". This is one of those conversations that quietly shifts how you see your own work.   It is BOLD to intentionally build the conditions for creativity. This episode shows you how.   If you want to reclaim your strategic clarity, break free from reactive operations, and ensure you're focused on the right priorities for growth, explore the Present Retreat™ approach. This will help you lead with intention and make the time you already have more impactful — so you can see and seize your next big opportunity.  -------------------- You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.

    49 min
  5. ENCORE: Why Talent Alone Isn't Enough for Success

    Apr 30

    ENCORE: Why Talent Alone Isn't Enough for Success

    The leap from leading yourself to leading others is one of the most underestimated transitions in business. The self-awareness, discipline, and clarity that made you effective as an individual contributor don't disappear — they evolve. And the leaders who thrive are the ones who learn to extend those qualities outward. In this episode, Jess Dewell sits down with Tim Fortescue, Founder of 40 Watt Coaching, to explore what it really takes to build a team that moves with purpose. They dig into how honest self-knowledge becomes the foundation for trust, how the way you communicate your vision determines whether your team feels aligned or adrift, and why slowing down to reflect is often the fastest way forward. You'll also discover how to uncover your grandest ideas and plan for them — planting seeds for the future, knowing your key performance levers, and finding what keeps you going when things get hard. Because the small wins matter: they build momentum, reinforce how your company does its best work, and deepen relationships through shared success. This episode is a practical and honest look at what truly drives performance — in yourself and in the people around you — and how to build the kind of momentum that compounds over time, one small win at a time. --------------------   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.

    54 min
  6. Scale and Pivot: How Hard Decisions Shape Business Evolution

    Apr 23

    Scale and Pivot: How Hard Decisions Shape Business Evolution

    Scaling a business isn't just a strategy — it's an act of faith. It demands the willingness to change course, challenge ingrained habits, and make decisions that are uncomfortable but necessary.   What really happens when things get hard? The answer lives in the decisions most business owners avoid: narrowing focus, eliminating bottlenecks, and making bold pivots before the market forces your hand. The shift to specialization, the ability to read and respond to market signals, and the discipline to leverage systems for clarity and execution — these are what separate businesses that survive from those that scale.   Long-term business ownership is built on recognizing what others overlook. Team alignment, having the right people in the right roles, and anticipating changes in customer needs aren't soft advantages — they're the foundation of a business that remains relevant over time. And when business models must evolve to keep pace with the market, the owners who endure are those who move with intention rather than reaction. Jess Dewell talks with Erik Dodier, EOS Implementer, about being in business long term, the Business Instinct required to remain relevant, and why it is BOLD to be ruthlessly focused on scaling from $10M to $100M.   —---------   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.

    44 min
  7. Why Guilt and Shame Affect Your Business Strategy

    Apr 16

    Why Guilt and Shame Affect Your Business Strategy

    Past successes can provide valuable insights, but it's important to recognize that they belong to a different time. While experience is beneficial, the ever-changing business landscape means that relying solely on past achievements can be misleading.    It's essential to understand that perfection is not a realistic goal and can sometimes become a barrier in your leadership journey. By accepting this reality, your approach to growth can transform, allowing you to focus on what truly matters. This discussion invites you to reevaluate your perspective on risk, failure, and self-advocacy.   In this program, you will hear that undesired results are justified by numbers and metrics, that decisions are always flexible and not irreversible, and that past successes don't guarantee future achievements.    In a conversation with Jess Dewell, Coach Kevin Voisin, CEO of We Live Legend, LLC, highlights the significance of continuous learning, adaptability, and honest self-reflection. These practices help to eliminate hidden feelings of guilt and shame, ultimately paving the way for future success and exploring how to move beyond past successes and open up new possibilities, even when the outcomes are uncertain.   —---------   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.

    51 min
  8. ENCORE: Trust Your Purpose Through Times of Change

    Apr 9

    ENCORE: Trust Your Purpose Through Times of Change

    We often think of innovation as loud—the flashy announcements, the social media hype, the constant spotlight. But the most profound changes happening right now are quietly being built behind the scenes.    The real disruptors aren't chasing notoriety; they are chasing root problems.    When you align a team around a mission that actually matters, you create an invisible force. That culture of shared purpose becomes the leverage needed to challenge industry giants who have benefited from the broken system for years.    The most valuable work isn't always visible. It's the daily, intentional effort to chip away at complex issues, build technology that works seamlessly in the background, and prioritize substance over facade.    In this Bold Business Podcast episode, Jess Dewell spoke with Sufian Chowdhury, CEO and Co-Founder at Kinetik, about what it really takes to disrupt an industry. If you want to make a real impact, look for the quiet, difficult problems. That is where the future is being shaped.   --------------------   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.

    35 min
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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
    507
  • Rating
    Clean
  • Copyright
    © Red Direction, LLC
  • Show Website
    Bold Business Podcast