Bold Business Podcast

Bold Business Podcast

Our roles as leaders constantly evolve, as does our business – whether from changes in the market, adjusting course to stay on the company vision or even to the number of hats worn. Problems reveal themselves when we understand people and read situations well. However, sometimes the chatter within our own mind, expectations of others and our own limiting thoughts … add complexity. Here on the Voice of Bold Business Radio we talk 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. You will find reflections on what worked within real situations … and what didn't. You will find ideas discussed that apply to your situation and spark curiosity. These conversations deliver possibility. In every program, we acknowledge there is more than one way to reach the end goal. Action matters. Bold Business includes strategy, ideas, leadership, promotion, operations, prioritizing, confidence, problem-solving, solutions, communication, marketing, values, goals, efficiency, responsibility, sustainability, accountability, manners, rules of engagement, vision, mission, business, transitions, management, crisis management, character, soft skills, core competencies, tactical skills, what works (and doesn't) – all from Business Advocate Jessica Dewell. Transcripts, highlights and immediately useful show notes are available for each episode. Go to VoiceOfBoldBusiness.com for show archives. The Voice of Bold Business is brought to you by Red Direction.

Episodes

May 28, 2026 38 mins

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 wha...

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The Two-Year Test: Would You Still Want to Own Your Company?
Forget distant five- and ten-year plans—if you picture your role two years from now, what would need to change? Hear the mindset and tactical pivots that make the next 24 months transformative for you and your business.

Whether you are steering a boutique firm, scaling a mid-market powerhouse, or navigating a large enterprise, reducing operationa...

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"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...

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"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 do...

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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, ...

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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 shi...

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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 reali...

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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 ...

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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 you're not genuinely engaged in the journey, you're likely confined by standards that don't serve you.

 

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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.

 

Introducing your Future-Maker panel:

 

- Christy Maxfield, President and CEO of Purpose First Advisors

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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 support your company and uplift your team.

 

In this exciting episode, you'll explore whether you're truly taking th...

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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 transformation isn't solely about achieving efficiency and cutting costs. It also involves adopting new mindsets not o...

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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 teams. 

 

Honest self-reflection is essential for setting goals, adapting to changes, and navigat...

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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 success.

 

Your business strategy should be aimed at the long-term — fostering growth and profitability while embracin...

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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 landscape. Take proactive steps by delegating responsibilities, launching experiments, and truly listening to your ...

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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 help you excel in your field, but also it reveals the best path forward. By recognizing how to use your resources...

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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 and being ruthless in your priorities, even if it means stepping outside your comfort zone or distancing yoursel...

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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, your team, and your customers.

 

Jess Dewell from Red Direction, Christy Maxfield of Purpose First A...

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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 can be quite a challenge, particularly as your company faces new constraints and friction points. 

 

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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 your day will give you MORE energy. 

 

You can have "space" in your meetings, conversations, or company culture...

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