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Bold Business Podcast

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Rating
★★★★★
5
from
25 reviews
This podcast has
502 episodes
Language
English
Publisher
Jess Dewell
Explicit
No
Date created
2017/06/21
Latest episode
2026/04/23
Average duration
47 min.
Release period
7 days

Description

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.

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Podcast episodes

Check latest episodes from Bold Business Podcast podcast


Scale and Pivot: How Hard Decisions Shape Business Evolution
2026/04/23
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.  
Why Guilt and Shame Affect Your Business Strategy
2026/04/16
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.
ENCORE: Trust Your Purpose Through Times of Change
2026/04/09
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.
ENCORE: Commit to Yourself: Defy Norms to Reach Your Goals
2026/04/02
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.   This discussion focuses on demonstrating your commitment to yourself and the people around you. It emphasizes the importance of embracing your truth and building a life that reflects your core values. The foundation of strong self-discipline may begin with the promises you make to others.   It involves letting go of the acceptable, mastering the subtleties of time and energy management, and cultivating the skills essential to success. The resulting advantage is reaching your most significant long-term objectives while remaining authentic to yourself throughout the journey.   Jess Dewell talks with Bolanle Williams-Olley, CFO of Mancini Duffy, about the significance of challenging 'norms' to achieve one's ambitions and why it takes courage to break away from them.   -------------------   Is the Daily Grind Clouding Your Business Instinct? Check out Present Retreat: a repeatable leadership practice designed to strengthen business instinct and strategic clarity, Download your FREE GUIDE here. -------------------- You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.
Stop Future-Proofing: The Mid-Market Guide to Future-Making
2026/03/26
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 Barta, Founder and CEO of Barta Business Group - Jess Dewell, Managing Partner and Growth Strategist at Red Direction   Tune in to explore the differences between playing defense and offense, the unintentional growth throttling that can occur, the power of curiosity, and how true accountability fuels progress.    This episode offers practical insights—from empowering teams and celebrating small victories to building a business that supports succession and growth. You'll find valuable tips to shift your mindset, prioritize effectively, and cultivate a culture that embraces the future.   Your business's success hinges on the decisions you make today. Each small victory, combined with a commitment to accountability, accelerates your momentum. Whether you're focusing on staying competitive or planning an exit strategy, this episode provides a bold perspective and actionable strategies to help you become a true future-maker.   --------------------   If you want to move from daily uncertainty to unwavering confidence, lead with clarity, make sharper decisions, and build a business that not only survives but thrives through change, check out the Driving Solutions Strategic Intensive program.   -------------------- You can get in touch with Jess Dewell on Twitter,  LinkedIn or Red Direction website.
ENCORE Business Mindset: Learning From Your Experience
2026/03/19
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 the right risks.   Get ready to uncover three vital steps for managing mistakes, understand the feeling of being poised to take bold action, and learn about three critical areas you need to watch to protect your business from potential failure.   Join Jess Dewell and her guest, Bew White, Executive Chairman of Summer Classics/Gabby, as they discuss the crucial role of decision-making in business.    They explore the ups and downs of valuable experiences, revealing that while the journey may be tumultuous, the rewards can be incredibly satisfying!   --------------------   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.
From Vision to Execution: Why CEOs Must Rethink Success in the Age of AI
2026/03/12
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 only to survive in business, but also to significantly increase your impact in the years to come.   In this program, you will learn about the traits necessary to grow your business 300 times with AI, the three steps to embrace and integrate AI into your operations, and the importance of understanding what NOT to do amidst a multitude of choices.   Jess Dewell speaks with Steve Brown, an AI futurist, about why humility, experimentation, and vision have become essential superpowers for modern executives. They discuss how small and mid-sized companies can lead in an AI-first economy rather than keep up, and how to be BOLD and strategically prepare for the next evolution of your company, even when it feels unimaginable.   --------------------   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.
From Friction to Growth: How Self-Reflection Drives Success
2026/03/05
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 uncertainty. A crucial takeaway from this discussion is that the concept of "enough" is a personal measure rather than a comparative one.   In this program, Jess Dewell engages with Marnie Stockman and Nick Coniglio, Co-Founders and Co-Authors of "The Business of You," as they explore the tough questions that drive growth. They emphasize strengthening your connection to core values and using your character skills to address uncertainty head-on.    You'll discover how to take greater ownership in times of challenge, how to lead yourself effectively, and what it truly means to be BOLD as you navigate friction to propel your success forward.   —-----------------   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: Make Decisions with Imperfect Information
2026/02/26
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 embracing whatever challenges and opportunities come your way.    Building a robust network of peers is crucial. Whether it's through a mastermind group or a board of directors, surrounding yourself with trusted allies allows you to brainstorm ideas, share experiences, and seek expert guidance when trying to steer your growth journey.   In this program, Jess Dewell sits down with Geneve Huxley, the Founder and CEO of Huxley CPA Consulting. They discuss the common obstacles companies face and explore how to harness powerful financial insights to overcome them.   Tune in for practical advice on how to track what truly matters, discover three dynamic tools to amplify the effectiveness of your decisions, and learn how to firmly establish your business goals.    --------------------   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.
Empower Teams and Lead Innovation in the Age of Automation
2026/02/19
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 customers — even if you haven't established a perfect system yet.   In this episode, you'll discover that managing energy is just as crucial as having the right systems in place, how to eliminate barriers, and the importance of letting go of processes that hinder growth.    Jess Dewell welcomes Solomon Thimothy, Co-founder and CEO of oneIMS, exploring his journey to uncover BOLD growth opportunities within his company and to redefine the CEO growth strategy through continuous adaptation.   —-----------------   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.
UNCHARTED: The Real Power of Knowing What You Can Control and Influence
2026/02/12
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 effectively in any situation, you gain greater control over your circumstances.   In this episode, you'll discover the importance of acknowledging what you want to avoid, allowing you to eliminate unproductive tasks. When faced with situations beyond your control, shift your focus to how you can influence outcomes. You'll also learn to reframe setbacks, using them as opportunities to strengthen your foundation and achieve your goals.   Jess Dewell welcomes Apollo Emeka, Managing Director of Apollo Strategy Group, to discuss how to infuse fulfillment into your major decisions and why it's BOLD to master the basics, ultimately leading to a sense of satisfaction as you act on your aspirations.   —-----------------   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.
Cut Through the Noise and Build Resilience as an Entrepreneur
2026/02/05
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 yourself from loved ones, is essential for determining your success.    Remember, who you were yesterday doesn't dictate who you need to be to fully embrace life and take action toward your biggest dreams.   In this episode, you'll discover the power of sharing your story, even while you're still living it. You'll learn that releasing what doesn't serve you makes room for gratitude, and that sacrifice isn't about what you lose — it's about filtering out the noise.   Jess Dewell chats with Benny Mobley, a Legacy Coach, about the importance of reclaiming your authority through small, consistent daily efforts. They explore how to overcome limiting beliefs and embrace authenticity to build the resilience needed to thrive as an entrepreneur.   —-----------------   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.
The CEO Evolution: Re-Engineering Your Role to Unlock 10x Value
2026/01/29
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 Advisors, and Dean Barta from Barta Business Group have an open discussion about how you might be the bottleneck hindering your business growth.   Here are key notes you don't want to miss:    ** Assess and sharpen your focus - The greatest obstacle to growth often lies in avoiding tough decisions. Failing to make a choice is still a choice — and it can dilute your impact. Set aside dedicated time (like a focused retreat) to review your priorities, clarify the true value you provide, and eliminate the "busywork" that distracts from strategic advancement.   ** Differentiate your roles for clarity and growth - Many business owners find themselves unintentionally wearing the CEO hat, which can pose challenges. Ask yourself: would you hire yourself for this role? Establish clear job descriptions for both CEO and Owner to define your responsibilities, promote effective delegation, and identify where you can add the most value — then focus relentlessly on those areas.   ** Unleash your greatest asset: YOU - Sustainable and exponential growth begins when leaders evolve authentically, delegate tasks that no longer align with their strategic vision, and cultivate habits that keep them in their zone of genius. Keep in mind: the value you realize for yourself directly influences the value your company delivers to customers and prospective buyers.   After the discussion, your expert panel shared their biggest takeaway:   Dean Barta: Separating the roles of owner and CEO: Assess whether you would hire yourself to be the CEO of your company.   Christy Maxfield: This about making sure that you can unlock more value for your customer, about unlocking more value for you as an owner, about unlocking more value for a future buyer.   Jess Dewell: Your ability to make decisions will get easier, stronger, and clearer. That ensures that you are evolving and assessing as you go.   --------------------   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.
Investor Insights: Business Scaling, Conflict, and Operational Excellence
2026/01/22
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.    You, your team, and your investor partners will achieve the most significant milestones by collaborating through difficulties.   In this program, you'll learn how to address the "stay in your lane" mindset that might be holding you back, why it's essential to disrupt your own company before the market does, and how to achieve strategic clarity.   Jess Dewell and Melanie Nabar, Vice President at Volition Capital, unpack how unclear objectives and scattered initiatives can waste resources and opportunities. They provide actionable steps to help maintain your momentum and emphasize how BOLD founders challenge themselves as leaders to embrace continuous learning and transformation.   --------------------   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.
UNCHARTED: Energize Your Team: The Power of Curiosity and Brave Belonging
2026/01/15
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 to unlock your team's best ideas. It is the intangible connections that transform how your business scales, grows, and belongs together.    Embrace experimentation — after all, we all do it already. Be intentional about tuning in to the people around you, and work to overcome any feelings of shame or embarrassment that may hold you back from acknowledging how interesting each person is.    Jess Dewell talks with Heather Hester, Founder of More Human More Kind, about being BOLD and acting with courage even when it feels uncomfortable or risky, and about being brave and honest about mistakes and strategic challenges to reach your growth potential.    Tune in to explore what you're already doing successfully, which will help you enhance those efforts and demonstrate positive energy management and trust-building behaviors. You'll also learn about the concept of "Brave Belonging" and how cultivating curiosity can energize your team.   --------------------   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.

Podcast reviews

Read Bold Business Podcast podcast reviews


5 out of 5
25 reviews
★★★★★
Life is Precious 304093 2024/12/04
Always a great podcast!
I listen to the Bold Business Podcast frequently. What I like about it is the optimism of the podcast tempered by practical real world business acumen...
★★★★★
Dr. Savannah 2024/08/09
Practical, strategic, inspiring
The Bold Business Podcast inspires (and teaches) me to continuously uplevel my business. I love it! Jess brings into this podcast her depth of experie...
★★★★★
cool ac 2024/05/23
Great Resource for Business Owners
I enjoy listening to this podcast to inspire me and give me ideas for how to better operate my business. As a Seattle business owner, it is also fun f...
★★★★★
Snow snob 2023/08/28
Unparalleled information
If you are looking to truly drive results and get focused on what truly matters, look no further than the Bold Business Podcast by Jess Dewell!
★★★★★
David Shriner-Cahn 2022/08/12
Growing with wisdom and compassion
If you want to succeed in business today, your ability to flex and adapt is more important than ever. It may take boldness to maneuver wisely. The B...
★★★★★
Dr. KPH 2021/05/28
Fantastic!
This is a must listen to podcast! Jess brings a wealth of knowledge and information to every episode!
★★★★★
RWlistens 2021/03/22
Fantastic
Jess is clearly passionate about these topics and wants to normalize these issues that people in business face. Just a great show all around.
★★★★★
tommye w-c 2021/03/22
Great!!
Absolutely amazing insights and information!
★★★★★
Joshill:) 2021/03/22
Really breaks it down
Great show that explains larger business concepts in a practical, simple way. Awesome production!
★★★★★
LiveBlissedOut 2021/02/10
Very Informative
Jess is so full of life and her passion comes through in every episode. I always learn great information and have fun listening! Thank you, Jess :)
check all reviews on apple podcasts

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