Bold Business Podcast
by Jess Dewell
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.
Episodes
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Recognizing Stress and Redefining Normal in High-Pressure Businesses
Does your company's forward momentum hide burnout blind spots? Burnout isn't just a buzzword. For many high-performing leaders, it builds quietly beneath the surface, invisible until it isn't. Every setback you push past without pausing adds to an emotional debt that eventually comes due. In this...
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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...
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Outdated Plans, Exhausted Teams: How to Regain Momentumand Navigate Market Volatility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...
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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...
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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...
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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...
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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…
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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...
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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...
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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...
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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...
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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...
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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,...
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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…
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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...
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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…
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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...
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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...
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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…
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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...
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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....
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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...
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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...
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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...
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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…
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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...
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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....
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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...
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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…
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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…
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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...
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ENCORE: Commit to Yourself: Defy Norms to Reach Your Goals
Stop attempting to fit into a mold that was never intended for you. Your dreams may need a reality check to prevent them from slipping away, ensuring you don't unintentionally drift further from them. Following a plan, establishing habits, and achieving goals may seem straightforward, but if…
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Stop Future-Proofing: The Mid-Market Guide to Future-Making
Many mid-market companies tend to hit a wall around the eighth year. The very processes that helped you get to this point are now what's holding you back from moving forward. This panel discussion aims to break the cycle of 'future-proofing' and focus on what it takes to stay relevant.…
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ENCORE Business Mindset: Learning From Your Experience
Making decisions is more than just picking an option; it's an art that influences your path forward, impacts your relationships, and challenges your values. By embracing your unique personality and strengths while being mindful of your leadership weaknesses, you can discover the best ways to...
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From Vision to Execution: Why CEOs Must Rethink Success in the Age of AI
The era of having all the answers is over. Today, it is becoming the norm for founders and management teams to lead without knowing exactly where they are headed. Change is occurring across every aspect of business and how we conduct it, and it will continue to impact the workforce. This...
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From Friction to Growth: How Self-Reflection Drives Success
Your character and skills often outweigh your credentials in today's ever-evolving world. True growth stems from the challenges of difficult conversations, and effective leaders can use these moments of discomfort to tap into the potential that already exists within their systems, processes, and...
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ENCORE: Make Decisions with Imperfect Information
In a world where every choice is navigated with limited information, you may find yourself stepping into the unknown, missing key insights, or even underestimating potential risks. However, the clarity of your vision and your commitment to your goals will ultimately dictate your journey to…
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Empower Teams and Lead Innovation in the Age of Automation
Transform complaints into golden opportunities and bring enthusiasm to your customers by empowering your team to swiftly address friction points. Embracing change is essential, and it's perfectly fine to reconsider past decisions. Flexibility is key to successfully navigating today's growth...
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UNCHARTED: The Real Power of Knowing What You Can Control and Influence
Are you underestimating your actual level of control? Learn why redirecting your attention from the obstacles you can't change to the factors you can influence can transform your business growth. "Control the controllables" is more than just a saying; it's a powerful mindset. Not only does it…
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Cut Through the Noise and Build Resilience as an Entrepreneur
True sacrifice involves letting go of distractions and negative influences, rather than letting go of the people or things you truly care about. Our personal stories — both the ones we share and those we keep to ourselves — play a crucial role in shaping our leadership. Establishing boundaries…
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The CEO Evolution: Re-Engineering Your Role to Unlock 10x Value
If your job as CEO hasn't changed in three years, your company might be outgrowing you. To elevate your business 10x, it's essential to reassess your role as CEO, make tough calls, and prioritize with unwavering focus. These are the key areas where you can unlock significant value for yourself,...
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Investor Insights: Business Scaling, Conflict, and Operational Excellence
A fuzzy strategy comes with real costs, and that lack of clarity can diminish true value. Think you're scaling well? Think again. It's crucial to support a bold vision with clear direction and regular reality checks. Identifying your unique growth factor while staying focused on the core problem...
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UNCHARTED: Energize Your Team: The Power of Curiosity and Brave Belonging
Being curious and stepping into new dynamics are tangible signs of bold leadership. It requires committing to courageous practices that ultimately make the greatest impact both in business and beyond. And it starts with you, as an authentic individual. Bringing more of yourself to every moment of...
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ENCORE: Embrace Endings and Create Powerful Beginnings
Endings often go unnoticed. It's easy to push back project deadlines and adjust our expectations for results, but calling for a definitive stop to review our progress can be much harder. We might feel the urge to dive right into tactics to achieve results, yet what we're truly after is a clear,...
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ENCORE: Modern Leadership Development (Goal Chat)
This episode originally aired on GoalChat, hosted by Debra Eckerling, a goal strategist and the creator of The DEB Method. The panel features Jess Dewell, Managing Partner at Red Direction, who specializes in operations and strategy; Jeannette Seibly, a results-driven leadership coach; and Isioma...
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ENCORE: Leverage Your Expertise to Grow Profitable Businesses
The depth of your knowledge opens up new opportunities. The more you learn, the more you realize there's so much left to explore, which is why curiosity is key. Asking questions like, "What's going on behind this process?" or "What discoveries can help our industry improve?" is crucial. Also,...
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Leading Through Uncharted Territory: Lessons for CEOs in Fast-Changing Markets
Yesterday's playbook is useless for tomorrow's problems. Smart companies evolve their people, keep clarity around priorities, navigate uncertainty and grow. The Gauntlet of Growth for sustainable growth has six parts: sharpening focus, calibrating culture, strengthening leadership, elevating...
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UNCHARTED: The Role of Gut Feelings: Transforming Shame into Strength and Assertive Action
Are you responsible FOR your team or TO them? It takes courage to confront and transform the internalized shame and disgust that can affect our ability to harness anger as a force for good. The next time you experience feelings of anger or shame, take a moment to pause and ask yourself, "Is this...
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Become a Conscious Creator: Elevate Your Life and Business With Positive Belief
Business teams thrive or struggle based on the attitude of their leadership. As a leader, you have the power to influence and uplift your team's environment, creating a significant impact through clear internal communication and a strong external presence. Are you building an opportunity or...
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Seeds of Wisdom: Power is the pause
In the pursuit of success, many people become fixated on future goals, often missing a vital ingredient for achievement: the power of taking a pause. How we manage our time dramatically influences what we can really accomplish. Welcome to an exciting ENCORE episode of the BOLD Business Podcast!...
About this show
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.
Hosted by
Jess Dewell
Categories