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. 6d ago

    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

  2. Aug 6

    From Self-Doubt to Bold Impact: Lessons in Leadership and Industry Disruption

    Stepping up is essential for you, your team, your customers, and your service to create real impact. In this episode, Jess Dewell talks with Heather Gibson, Owner at Big Hearted Breeders, about how recognizing self-doubt is necessary for self-acceptance in the process of facing industry disruption. She shares that she is BOLD in order to meet the self-doubt that arises by remembering her purpose.   More than challenging misconceptions, outdated traditions, and external judgment is your dedication to your work. And that your work has value. Profit is not a dirty word. It is survival. You can indeed run a profitable business, stand in your power, and share your passion with on-purpose work.   In this episode, you will discover:   How the "invisible committee" of unseen opinions impacts your self-perception and business decisions Why unsolicited criticism can undermine your confidence — and how to stay grounded in your purpose The power of morning and evening rituals to maintain clarity and direction How new tools and technologies are leveling the playing field for business owners Three questions to ask to discover what no longer works so you can let things go Why finding commonality with others creates greater impact and change The importance of regular reflection to ensure you're intentionally moving toward your vision How stepping back from daily operations protects your bandwidth and positions you as the visionary your industry needs   Remembering your purpose is a powerful ally when self-doubt shows up. The way to create real change is to find commonality with others as you move along your path. —--------- 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.

    From Self-Doubt to Bold Impact: Lessons in Leadership and Industry Disruption

  3. Jul 30

    Rewarding Hidden Contributions: The Future of Talent Measurement

    You just invested in the latest feedback tool, the best collaboration platform, the smartest productivity software. And nothing changed. Not because the tools are bad — but because you're still measuring the wrong things. You're still rewarding the visible. You're still missing the people who quietly hold your organization together. The future of work isn't about better tools. It's about measuring what actually matters. And what actually matters — reliability, leadership, attitude, the intangibles that move teams — has been invisible to your reward systems for too long. Jess Dewell talks with Jacob Chase, Founder & CEO of The INFIN, on how organizations can stop chasing innovation for innovation's sake and start measuring the human contributions that technology can't replace. Jacob has built systems that capture what traditional evaluation misses: the peer-recognized strengths that drive real organizational change. In this episode, you'll discover: Why innovative tools fail to drive change — and the real hurdle isn't the technology, it's understanding how people actually want to work. How to build feedback systems that tell you the truth — and why anonymity and safety are non-negotiable for honest insights. Why it's time to redesign your entire measurement and reward infrastructure — not just tweak the old system. How autonomy, initiative, and transparent reward systems create sustainable growth without chaos. Why real-time, continuous feedback outperforms annual reviews — and what that looks like in practice. How to measure the intangibles — leadership, reliability, attitude — that have the biggest impact on team performance. What a decentralized feedback system can capture that traditional metrics miss entirely. It is BOLD to reimagine culture and measuring formerly intangible value for all stakeholders. The organizations winning today aren't the ones with the fanciest tools. They're the ones measuring what matters. They're recognizing contributions that numbers alone can't capture. They're willing to look beyond job titles and formal roles to see who's actually driving value. They've built systems where peer recognition and transparent rewards amplify the strengths that move culture forward. The disconnect between tools and culture is growing. Companies invest heavily in platforms for feedback but still rely on outdated evaluation methods. They claim to value collaboration but reward individual achievement. They say culture matters but measure only output. That gap is costing you talent, innovation, and resilience. If your feedback systems feel disconnected from reality, if your best people aren't getting recognized for their true contributions, or if you're wondering how to measure the intangible qualities that are actually holding your team together, this conversation will reorient 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.

    Rewarding Hidden Contributions: The Future of Talent Measurement

  4. Jul 23

    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

  5. 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

  6. 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

  7. 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

  8. 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
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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
    518
  • Rating
    Explicit
  • Copyright
    © Red Direction, LLC
  • Show Website
    Bold Business Podcast