Jess Dewell
Bold Business Podcast
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.
Where to listen?
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Episodes
Leadership Transitions: From Change and Resistance to Resilient Teams 09.07.2026 44:19
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 st...
CEO Confessions: Loneliness, Building the Right Team & Bold Growth 02.07.2026 41:25
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 reck...
ENCORE: How To Avoid The Hidden Costs Of Growing Your Business 25.06.2026 50:35
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 inf...
Clarity, Fairness, and Care: The Secret to High Trust Organizations 18.06.2026 41:41
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. Trust isn't an intangible value or a soft skill. It's measurable, concrete operational infrastructure....
Productive Struggle and Joyful Leadership: Redefining Success in Business 11.06.2026 45:33
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 business landscape. Dr. Berry challenges the "go it alone" approach to leadership, making the case that...
Surviving Algorithm Shifts: Clear Messaging and Smart Advertising 04.06.2026 35:59
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 when algorithm shifts, shrinking social ROI, and an AI-saturated ad landscape all arrive at the same tim...
Workplace Legal Issues Every Company Leader Needs to Know 28.05.2026 38:56
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 h...
The Business Evolution Roadmap: Bridging the Gap from Here to There 21.05.2026 51:23
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 pract...
Guiding Growth: How to Keep Your Team, Tech, and Strategy Relevant 14.05.2026 41:15
"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 stopp...
ENCORE Mindfulness and Creativity: Unlock Your Business Potential 07.05.2026 49:15
"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 t...
ENCORE: Why Talent Alone Isn't Enough for Success 30.04.2026 54:26
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...
Scale and Pivot: How Hard Decisions Shape Business Evolution 23.04.2026 43:47
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...
Why Guilt and Shame Affect Your Business Strategy 16.04.2026 51:11
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 t...
ENCORE: Trust Your Purpose Through Times of Change 09.04.2026 34:33
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 shar...
ENCORE: Commit to Yourself: Defy Norms to Reach Your Goals 02.04.2026 50:04
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. ...
Stop Future-Proofing: The Mid-Market Guide to Future-Making 26.03.2026 51:39
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 - Dean...
ENCORE Business Mindset: Learning From Your Experience 19.03.2026 35:03
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...
From Vision to Execution: Why CEOs Must Rethink Success in the Age of AI 12.03.2026 49:05
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 minds...
From Friction to Growth: How Self-Reflection Drives Success 05.03.2026 45:28
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 navigating...
ENCORE: Make Decisions with Imperfect Information 26.02.2026 46:34
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...
Empower Teams and Lead Innovation in the Age of Automation 19.02.2026 53:00
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...
UNCHARTED: The Real Power of Knowing What You Can Control and Influence 12.02.2026 52:53
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...
Cut Through the Noise and Build Resilience as an Entrepreneur 05.02.2026 46:12
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 distancin...
The CEO Evolution: Re-Engineering Your Role to Unlock 10x Value 29.01.2026 46:59
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 Advi...
Investor Insights: Business Scaling, Conflict, and Operational Excellence 22.01.2026 44:09
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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