
The Thoughtful Entrepreneur
You’re gonna love this DAILY, commercial-free entrepreneur spotlight show. We feature CEOs and founders of 6-9 figure B2B companies. Agencies, coaches, consultants, and other leaders share not only their success stories - but their advice for business leaders focused on business growth.
You’re going to hear real stories from real people all in 15-25 minutes time - perfect for your commute.
On this podcast, your host, Josh Elledge encourages entrepreneurs to share not only their expertise but their stories and their hearts.
We believe that every person has a unique message which can positively impact the world. Even YOU! If you’d like to be featured on The Thoughtful Entrepreneur, apply here: https://UpMyInfluence.com/guest/
Latest episodes

Apr 25, 2025 • 21min
2162 - Transforming Your Expertise into High-Ticket Services with Level Up Creators' Amanda Northcutt
Building Recurring Revenue Businesses: Insights from Amanda Northcutt🎧 Listen to this episodeIn this episode of The Thoughtful Entrepreneur, host Josh Elledge engages in a dynamic conversation with Amanda Northcutt, founder and CEO of Level Up Creators. Amanda shares her expertise in helping coaches, consultants, and creators build businesses with stable, recurring revenue streams. This episode provides invaluable insights for anyone looking to establish a sustainable income model and grow their business in a way that doesn’t burn them out.Level Up Creators: Helping Experts Build Sustainable BusinessesAmanda Northcutt is deeply passionate about helping subject matter experts—especially those in coaching, consulting, and the creator space—build businesses that rely on predictable, recurring revenue. Through her company, Level Up Creators, Amanda works with experienced coaches and consultants to help them scale by focusing on long-term client relationships and high-ticket services, rather than one-off engagements. This approach to business ensures entrepreneurs can focus on sustainability and stability instead of constantly chasing the next client.At the core of Level Up Creators' methodology is the MRA (Monthly Recurring Revenue) Method, which helps clients generate a steady income stream through high-value, high-touch offerings. Additionally, Amanda’s MRA Accelerator program is designed to help clients achieve multi-five-figure monthly recurring revenue within just seven months. These programs emphasize building long-term relationships with clients, providing continuous value, and setting up systems that allow for predictable business growth.Amanda's focus on long-term client relationships instead of short-term profits helps business owners reduce the stress associated with inconsistent income and promotes growth that lasts. This approach is not only about financial stability but also about creating a more fulfilling and sustainable business model.About Amanda NorthcuttAmanda Northcutt is a seasoned entrepreneur and the founder of Level Up Creators, where she helps coaches, consultants, and creators build businesses with recurring revenue streams. With 22 years of experience in consulting, start-ups, and marketing strategy, Amanda is a key figure in teaching others how to achieve sustainable wealth and business success. She also co-hosts The Level Up Creators Podcast, where she shares insights on business strategies and growth.About Level Up CreatorsLevel Up Creators is committed to empowering coaches, consultants, and creators to build long-term, recurring revenue. Their services include the Level Up Creator School, MRA Accelerator, and personalized coaching to help entrepreneurs scale their businesses while maintaining high-touch engagement with their clients. Their mission is to make recurring revenue accessible to creators and experts at all stages of business development.Links Mentioned in this Episode:Level Up Creators WebsiteAmanda Northcutt’s LinkedIn ProfileLevel Up Creator School WebsiteKey Episode Highlights:Building Recurring Revenue: Amanda explains why recurring revenue is the foundation of sustainable business growth and how to implement this model.Client Retention: Focus on understanding your customers' ongoing needs and providing solutions to keep them coming back.Genuine Client Relationships: Emphasizing authenticity over automation in lead generation and client relationships.Down-Market Expansion: Amanda discusses how to scale services to reach a broader audience while maintaining high-touch interactions.Value-Based Pricing: Aligning your pricing with the value you provide rather than the amount of time spent.ConclusionThis episode offers a wealth of insights into building a consulting business that thrives on recurring revenue and strong client relationships. Amanda Northcutt’s approach shows how focusing on long-term value, personalization, and strategic scaling can lead to a sustainable and fulfilling business. By implementing the strategies discussed, entrepreneurs can build predictable income streams and reduce the stress of traditional business models.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Apr 25, 2025 • 21min
2161 - The Joy Formula: 12 Steps to True Fulfillment with Keren Eldad
Breaking Free from the Cage of Ambition: Insights from Keren Eldad🎧 Listen to this episodeIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Keren Eldad, an executive coach, professional speaker, and author of the book Gilded: Breaking Free from the Cage of Ambition, Perfectionism, and the Relentless Pursuit of More. Keren shares profound insights on the pressures faced by high achievers, societal expectations that often lead to feelings of entrapment, and the importance of prioritizing happiness and well-being over constant work and external success markers. The conversation serves as a roadmap for anyone looking to break free from the cycle of ambition and perfectionism to live a more fulfilling and joyful life.The Essence of Keren's Work: Helping High Achievers Find FulfillmentKeren Eldad, also known as "Coach Keren," has dedicated her career to helping high achievers break free from the cycles of ambition, perfectionism, and the relentless pursuit of "more." Her clients include Olympic athletes, politicians, Hollywood stars, supermodels, Special Forces operatives, and serial entrepreneurs. Additionally, global organizations like Estée Lauder, J.P. Morgan, and Nike trust her expertise.Her coaching approach focuses on identifying the self-imposed cages many high achievers find themselves in, where success is pursued relentlessly at the cost of happiness and fulfillment. Keren teaches that true success lies not in the relentless pursuit of more but in creating balance, realigning goals, and finding joy in the present. She emphasizes the importance of self-reflection, helping clients regularly assess their motivations and desires to determine whether they are aligned with their true selves or simply driven by societal pressures.Keren’s book Gilded presents a 12-step program inspired by Alcoholics Anonymous, designed to guide individuals toward a more fulfilling existence. The book challenges the notion that success must come at the expense of happiness, offering readers a structured approach to reclaim their well-being and live a life that honors their true values.About Keren EldadKeren Eldad, known as "Coach Keren," is a renowned executive coach, speaker, and author of Gilded. Recognized as a Top Ten Executive Coach by the International Coaching Federation (ICF), Real Leaders Magazine, and Goop, Keren has made a significant impact on the coaching world. She works with high achievers globally, helping them overcome perfectionism and create more meaningful, balanced lives.Keren’s clients range from Hollywood celebrities and Olympic athletes to leaders in major corporations like Estée Lauder, J.P. Morgan, and Nike. As a former C-suite executive with experience in 17 countries across four continents, Keren coaches in English, Spanish, Hebrew, and French. She also reaches a global audience through her TEDx talks, which have garnered half a million views.Keren resides in Austin, Texas, with her husband, Ryan, and their many beloved pets.About Gilded*Keren Eldad’s book, Gilded: Breaking Free from the Cage of Ambition, Perfectionism, and the Relentless Pursuit of More, offers a transformative approach to helping individuals break free from the chains of relentless ambition and the pursuit of perfection. The 12-step program, inspired by the principles of Alcoholics Anonymous, guides readers toward achieving a balanced and fulfilling life by aligning their actions with their deeper, more authentic values. Gilded challenges the belief that success must be sacrificed at the cost of happiness and shows how true fulfillment comes from living authentically, in alignment with one’s personal desires and goals.Links Mentioned in this Episode:Keren Eldad’s WebsiteKeren Eldad's LinkedIn ProfileGilded: Breaking Free from the Cage of Ambition, Perfectionism, and the Relentless Pursuit of MoreKey Episode Highlights:Breaking Free from Perfectionism: Keren explains how high achievers often become trapped by the cycle of perfectionism and how to break free from it.Redefining Success: True success comes not from endless achievement but from building meaningful relationships and finding joy in the present.The Importance of Happiness Now: Keren emphasizes the need to choose happiness in the moment, rather than postponing it for future goals.Workaholism as an Addiction: Keren highlights how workaholism is a form of addiction, driven by societal beliefs about hard work equating to success.Coaching for Clarity: The value of coaching is to gain self-awareness and align personal goals with deeper, more fulfilling desires.ConclusionIn this episode, Keren Eldad provides invaluable insights into breaking free from ambition, perfectionism, and the relentless pursuit of “more.” By focusing on self-reflection, embracing happiness now, and redefining success, listeners can create lives of greater joy and fulfillment. Whether through Keren’s coaching or her book Gilded, the journey to a more balanced and meaningful life starts with recognizing the need for change and taking the first step toward living authentically.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Apr 24, 2025 • 26min
2160 - Mastering Economic Change and Leadership Insights with GrowthSource Coaching's Steve Smith
Personal Growth and Leadership Insights with Steve Smith: A Comprehensive Guide🎧 Listen to this episodeIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Steve Smith, the founder and Business & Executive Coach of GrowthSource Coaching. Together, they dive into insightful discussions on personal growth, leadership, and how coaching can help entrepreneurs and business leaders thrive, especially in challenging times. Steve shares his expertise in leadership development and how it plays a pivotal role in achieving long-term success.Embracing Change and Lifelong LearningSteve Smith’s journey into coaching was marked by his willingness to embrace change and adapt. After spending 30 years in the consumer products industry, including stints with well-known companies like General Mills and Carter Wallace, Steve made a bold decision to transition into coaching. This shift wasn’t just a career move—it was a commitment to lifelong learning and personal growth. He shares that even with years of experience under his belt, he had to reframe his mindset to pursue something entirely new.His story is a powerful reminder that embracing new challenges can unlock new levels of potential, no matter where you are in your career. Steve speaks about the critical role persistence plays in personal development. Whether it’s learning a new skill or shifting your professional focus, staying committed to continuous growth is a theme Steve lives by. As he learned from his own experiences, pushing past the discomfort of change can lead to deeper fulfillment and success.Steve also reflects on the importance of coaching, explaining that business leaders often face challenges that can feel isolating. However, having the right guidance and support—whether from a coach or mentor—can significantly enhance clarity and performance. This rings especially true for entrepreneurs, who may be juggling multiple roles and responsibilities while trying to scale their businesses.About Steve SmithSteve Smith is a seasoned Business & Executive Coach and the founder of GrowthSource Coaching. With over 30 years of experience in consumer products manufacturing, including stints at top companies like General Mills and Carter Wallace, Steve transitioned into coaching in 2008 to help business owners, executives, and entrepreneurs realize their full potential. He has successfully worked with over 950 clients across various industries, helping them enhance their leadership and strategic thinking.About GrowthSource CoachingGrowthSource Coaching specializes in coaching business owners, executives, and leadership teams to unlock their potential and achieve long-term success. With a focus on personalized strategies, Steve and his team help clients navigate the challenges of leadership, business growth, and personal development.Links Mentioned in this Episode:GrowthSource Coaching WebsiteSteve Smith’s LinkedIn ProfileSteve’s Podcast: The Business WingmenKey Episode Highlights:Embrace Lifelong Learning: Steve shares his journey of picking up the guitar, demonstrating that it’s never too late to learn a new skill.The Power of Persistence: Success is often about showing up consistently and putting in the effort, regardless of the initial challenges.Focus on Your Strengths: Steve emphasizes the importance of identifying and leveraging your unique strengths for professional growth.Adapt and Evolve: Rebranding and repurposing your business can help you stay relevant and grow through adversity.Calm Leadership: In times of uncertainty, effective leaders maintain a calm demeanor and rely on trusted advisors to guide decisions.ConclusionIn this insightful episode, Steve Smith offers invaluable advice on personal growth, leadership, and how to navigate the complexities of today’s business environment. By embracing lifelong learning, focusing on self-awareness, and continuously adapting, listeners can take actionable steps toward becoming more effective leaders and achieving long-term success.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Apr 24, 2025 • 24min
2159 - A Guide to Storytelling That Attracts Clients with The Story Engine's Kyle Gray
The Power of Storytelling in Business: Insights from Kyle Gray🎧 Listen to this episodeIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Kyle Gray, an entrepreneur, bestselling author, and the founder of The Story Engine. Together, they explore how storytelling can be a game-changer for businesses, offering strategies to help professionals communicate effectively, inspire action, and drive growth. Kyle shares his journey, key lessons on personal expression, and actionable advice for leveraging storytelling to make a real impact in business.Why Storytelling Matters in BusinessStorytelling is often seen as an art, but Kyle Gray believes it’s a critical business skill that can drive both personal fulfillment and professional success. Throughout the conversation, Kyle emphasizes how a well-crafted story can differentiate your brand, inspire action from your audience, and ultimately lead to greater business growth. But why is storytelling so important in business?One key reason is that stories are much more memorable than facts alone. Our brains are wired to remember stories because they evoke emotion, creating a connection that data points simply cannot. For businesses, this connection means deeper engagement with your audience, and a higher chance of turning potential leads into loyal customers. Whether you're speaking directly to your audience, crafting a website message, or even pitching an idea, effective storytelling allows you to communicate more clearly and impactfully.Kyle shares that many businesses and experts struggle to connect with their audience because they become overly immersed in their technical knowledge. Instead of focusing on what the audience needs to hear, they overload them with complex jargon and information. The key to great storytelling, according to Kyle, is to distill complex ideas into relatable, human stories that inspire trust and action. This, in turn, can significantly boost lead generation, sales, and overall business growth.About Kyle GrayKyle Gray is a world-class presentation coach, story strategist, and author who helps coaches, startups, and executives use storytelling to better communicate their unique value and improve sales with their audience. He combines timeless storytelling with cutting-edge marketing to ensure clients have the right story to tell—whether presenting, on a sales call, or in conversation, both online and offline.About The Story EngineThe Story Engine empowers entrepreneurs to craft and communicate their stories in a way that resonates with their audience, builds trust, and inspires action. Kyle’s business helps individuals distill complex concepts into clear, impactful messages, enabling them to create deeper connections with their customers and achieve business success.Links Mentioned in this Episode:The Story Engine WebsiteKyle Gray's LinkedIn ProfileKyle’s Storytelling PodcastEpisode Highlights:Pursue Passion with Purpose: Kyle’s journey highlights the importance of aligning passion with purpose to find personal fulfillment while achieving business success.Embrace Personal Expression: Whether through music or storytelling, finding an outlet for self-expression can unlock greater creativity and satisfaction.Master the Learning Process: Just like learning a musical instrument, storytelling requires consistent practice and patience to refine.Cut Through the Noise: Focus on the key messages that will inspire action, rather than overwhelming your audience with excessive information.Show Vulnerability: Authenticity and vulnerability in storytelling create deeper, more genuine connections with your audience.ConclusionIn this episode, Kyle Gray offers invaluable insights into the power of storytelling and its impact on business success. He demonstrates how embracing vulnerability, focusing on key messages, and sharing personal stories can transform your communication and drive meaningful results. By applying these strategies, entrepreneurs can build trust, inspire action, and ultimately grow their businesses.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Apr 23, 2025 • 24min
2158 - Mastering AI Literacy Essential Skills for the Modern Workforce with Bizzuka's John Munsell
Embracing AI Literacy in the Workplace: Insights from John Munsell🎧 Listen to this episodeIn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with John Munsell, CEO of Bizzuka, about the critical need for AI literacy in today’s workforce. John brings a unique perspective to the conversation, blending his Southern charm—complete with barbecue anecdotes—with forward-thinking insights on how businesses can thrive by embracing AI strategically. As AI continues to reshape industries, John’s mission is to ensure companies not only adopt the technology but fully understand how to implement it ethically, effectively, and at scale.From Brisket to Business Intelligence: Understanding and Implementing AI in the Modern WorkplaceJohn’s journey from software entrepreneur to AI education leader is as flavorful as the barbecue he serves during his annual Mardi Gras tradition, Pork Palooza. His passion for community and precision in cooking mirrors the attention to detail he now brings to AI training. Just as thick steel helps maintain consistency in a smoker, John argues that well-structured frameworks are essential for maintaining clarity and effectiveness when deploying AI in an organization. Through Bizzuka, he helps business leaders avoid confusion and inefficiencies by teaching scalable prompt engineering—a method of breaking down complex AI inputs into simpler, more reliable components.During the episode, John and Josh explore how AI literacy is no longer optional—it’s essential. Both believe that every employee, regardless of role, should understand how to interact with AI tools. Josh shares how his team is trained on prompt engineering and natural language processing, setting a precedent for AI readiness. John agrees and explains the differences between tools like ChatGPT and Microsoft Copilot, noting that success often hinges on the user’s ability to clearly communicate with the AI. A well-known misstep? Vague prompts that accidentally train chatbots to talk like pirates—a real-life example John recalls with a laugh.The conversation takes a serious turn when discussing the legal implications of AI use. John warns against blindly relying on AI for content creation without understanding copyright laws. He recommends that businesses develop policies around AI-generated content and consult legal experts to mitigate risks. Bizzuka addresses these challenges through its structured training programs, which include modules on ethics, security, and safe content generation. Beyond corporate training, John is also committed to preparing the next generation. He recently partnered with professors at Louisiana State University to educate future leaders on practical AI use, ensuring the workforce of tomorrow is equipped for the AI-driven economy of today.About John MunsellJohn Munsell is the CEO of Bizzuka and a recognized leader in AI education and digital transformation. With a career that began in software development and evolved through digital marketing, John has spent the last several years focused on helping companies harness the power of AI safely and strategically. His work includes developing enterprise-level training programs and building scalable systems for prompt engineering. John’s down-to-earth approach combines technical depth with an emphasis on collaboration, ethics, and continuous learning.About BizzukaBizzuka is a consulting and training organization that helps companies implement AI tools responsibly and effectively. Through a blend of foundational training, department-specific skill tracks, and a free online community, Bizzuka empowers teams to become AI-literate and future-ready. Their programs emphasize ethics, prompt engineering, and collaboration, ensuring that AI becomes a trusted asset—not a mystery—in every organization.Links Mentioned in this Episode:Visit BizzukaJoin the Bizzuka AI CommunityJohn Munsell on LinkedInEpisode Highlights:Why AI literacy is essential for all employees—not just IT teamsHow structured prompt engineering improves AI output and collaborationKey legal considerations when using AI-generated contentThe difference between AI tools like ChatGPT and Microsoft CopilotThe role of community, ethics, and education in preparing for an AI futureConclusionThis episode is a compelling reminder that embracing AI is not just about adopting tools—it’s about understanding how to use them wisely. John Munsell’s insights offer a roadmap for business leaders who want to stay ahead of the curve, create empowered teams, and navigate the ethical and legal nuances of AI in the workplace. Whether you’re a corporate executive, small business owner, or educator, this conversation encourages you to take AI literacy seriously—and maybe enjoy some good barbecue along the way.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Apr 23, 2025 • 22min
2157 - Empower Your Future in Real Estate & Crypto Strategies with Damion Lupo
Damion Lupo on Entrepreneurship and Innovative Housing Solutions: A Deep Dive🎧 Listen to this episodeIn this episode of The Thoughtful Entrepreneur, host Josh Elledge engages in a dynamic conversation with Damion Lupo, a Financial Mentor and Author, about entrepreneurship, financial literacy, and personal empowerment. Damion offers powerful insights that can guide entrepreneurs on their journey to success, covering topics from innovative construction methods to financial freedom. This post breaks down the key takeaways from the episode, providing actionable advice for listeners looking to elevate their entrepreneurial game.Entrepreneurial Insights: Perseverance, Innovation, and Financial FreedomDamion shares his personal journey from financial struggle to empowerment, offering valuable lessons for entrepreneurs. After making and losing millions, including a period of homelessness, Damion found his purpose in helping others achieve financial freedom. His experiences taught him the importance of purpose-driven entrepreneurship—building businesses that not only generate profits but also provide solutions to real-world problems. He stresses that financial setbacks, while challenging, often provide transformative lessons that shape long-term success.A key takeaway from Damion’s journey is the importance of perseverance and authenticity in entrepreneurship. Just like the gritty characters in the TV series Yellowstone, Damion draws parallels between the tough realities of life and business, emphasizing that true success is earned through hard work, resilience, and staying true to your values. For entrepreneurs, understanding that the road to success involves challenges, embracing them rather than avoiding them, leads to deeper fulfillment and meaningful results.Damion also discusses how innovative housing solutions, particularly through advanced construction methods like Frame Tech, are revolutionizing the real estate industry. By utilizing controlled environments to manufacture components like walls, floors, and trusses, this approach is not only four times faster than traditional construction but also drastically reduces waste by 99%. This focus on efficiency, sustainability, and innovation is something Damion encourages all entrepreneurs to consider, especially in industries with complex challenges.About Damion LupoDamion Lupo is a Financial Mentor, Author, and entrepreneur passionate about empowering individuals to take control of their financial futures. With a wealth of experience in business development, financial literacy, and cryptocurrency, Damion has helped countless individuals break free from financial constraints. He is the founder of Financial Freedom University and the author of The Ten Steps to 10 Million, a guide to achieving financial independence. Damion advocates for active engagement in investments, the value of continuous learning, and taking a purpose-driven approach to entrepreneurship.About Financial Freedom UniversityFinancial Freedom University is an educational platform offering tools and resources for individuals seeking financial independence. Damion Lupo’s approach focuses on educating entrepreneurs and investors on how to actively engage in their investments, create real value, and make informed financial decisions. The platform provides courses, mentorship, and resources designed to help individuals create long-term wealth and live financially empowered lives.Links Mentioned in this Episode:Visit Financial Freedom UniversityDamion Lupo on LinkedInDamion Lupo’s PodcastEpisode Highlights:The importance of perseverance and authenticity in entrepreneurshipHow innovative housing solutions can revolutionize the real estate industryThe significance of purpose-driven entrepreneurship and financial empowermentWhy active participation in investments leads to greater wealth creationDamion's insights into achieving financial freedom and setting realistic goalsConclusionThis episode serves as a powerful reminder that success in entrepreneurship requires resilience, innovation, and a commitment to solving real problems. Damion Lupo’s insights into financial literacy, cryptocurrency, and purpose-driven business models provide entrepreneurs with a comprehensive roadmap for achieving financial freedom. By embracing the principles of perseverance, active engagement, and value creation, entrepreneurs can overcome obstacles and build sustainable, impactful businesses.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Apr 22, 2025 • 22min
2156 - Sustainable Sales Mastery with The Diamond Group's Theresa Bassett
Strategies for Small Business Growth: Insights from Theresa Bassett🎧 Listen to this episodeIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Theresa Bassett, CEO of The Diamond Group, to explore the strategies small business owners can use to scale beyond the seven-figure revenue threshold. With her extensive experience in sales and marketing, Theresa offers actionable insights into the challenges many entrepreneurs face as they aim for sustainable growth. She dives deep into the complexities of creating effective sales and marketing systems that drive predictable results.The Importance of a Structured Approach to Business GrowthTheresa introduces Momentum, a multi-phase system developed by The Diamond Group to help small businesses build structured, sustainable marketing systems. The process begins with goal setting, market research, and strategy development to establish a clear direction. In the execution phase, businesses focus on creating high-quality content, managing campaigns across multiple channels, and monitoring performance using analytics tools. This structured approach ensures businesses stay organized and aligned with their growth goals, making it easier to scale operations while maintaining control over their marketing efforts.Theresa emphasizes the importance of building a collaborative team to accelerate business growth. She highlights the need for entrepreneurs to focus on the “who” rather than the “how,” trusting their team to handle specific tasks. By bringing together professionals such as strategic account managers, marketing coordinators, and digital creative specialists, businesses can delegate effectively and maintain momentum. This collaboration enables business owners to concentrate on strategic decisions, rather than getting bogged down by day-to-day tasks, which ultimately leads to more efficient and impactful growth.About Theresa BassettTheresa L. Bassett is the CEO of The Diamond Group, specializing in digital marketing and sales strategy for professional service firms. With over $550M in marketing, advertising, and personal development transactions, she has helped legal, financial, and consulting firms refine their client acquisition strategies and elevate their brand presence. Theresa has developed a proprietary sales and marketing framework that helps professional service providers attract high-value clients while optimizing operational efficiency. She is the author of Uplevel: Sprint Your Way to the Next Level in Your Life and Business, offering a roadmap for professionals seeking growth and success.About The Diamond GroupThe Diamond Group is a leading consultancy that helps professional service firms, including legal, financial, and consulting businesses, grow by refining their sales and marketing strategies. The Diamond Group’s proprietary systems enable businesses to attract high-value clients, increase operational efficiency, and develop marketing systems that drive long-term success. Their results-driven approach ensures that clients can scale their firms effectively, even in challenging economic climates.Links Mentioned in this Episode:Visit The Diamond Group WebsiteFree Resources from The Diamond GroupTheresa Bassett on LinkedInEpisode Highlights:How to implement structured systems for scaling your businessThe importance of collaborating with a talented team to drive growthWhy a clear marketing strategy is essential for long-term successThe key phases of The Diamond Group’s Momentum systemHow to use analytics tools to optimize marketing effortsConclusionThis episode is packed with valuable advice for small business owners looking to break through growth barriers and achieve sustainable success. Theresa Bassett’s insights into creating structured marketing systems and building collaborative teams provide entrepreneurs with the tools they need to achieve consistent, predictable growth. With the right approach, any business can break through growth plateaus and achieve the seven-figure revenues they aim for.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Apr 22, 2025 • 23min
2155 - Entrepreneurial Mindset Lessons with Coach Bob Regnerus
Unlocking Potential: Insights from Coach Reg on Entrepreneurship and Personal Development🎧 Listen to this episodeIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Bob Regnerus, known as Coach Reg, to explore the powerful intersections between sports, entrepreneurship, and personal development. Drawing on his extensive background as a marketing coach, author, and speaker, Coach Reg shares actionable insights that can help entrepreneurs elevate their game—whether on the field or in the boardroom. From mental resilience to continuous growth, this episode offers valuable guidance for anyone looking to harness their full potential.The Parallels Between Sports and EntrepreneurshipCoach Reg begins by drawing key connections between athletes and entrepreneurs, emphasizing the relentless drive for improvement that both groups share. He explains how athletes like Michael Jordan and Tiger Woods continue to work with coaches despite their already impressive skill levels, illustrating the importance of ongoing development and seeking expert guidance. Just like top athletes, entrepreneurs must constantly hone their skills, push their limits, and seek new ways to grow. This drive for continuous improvement, Coach Reg argues, is a hallmark of success in both fields.In the world of entrepreneurship, the parallels to sports are evident. Both athletes and entrepreneurs are driven by ambitious goals and a deep desire to improve. They dream big and visualize their success, which fuels their daily efforts. Coach Reg highlights how these traits—along with resilience and a willingness to embrace challenges—are what ultimately lead to lasting success. Whether it’s on the field or in business, dreaming big and staying committed to personal growth are key to overcoming obstacles and reaching new heights.Navigating Uncertainty with a Calm and Focused MindsetAddressing the current uncertainties in the business landscape, Coach Reg shares his perspective on how entrepreneurs can thrive amidst chaos. He encourages listeners to view uncertainty as an opportunity to grow rather than a threat. Entrepreneurs who can remain calm and connected to their inner wisdom will navigate challenging times more successfully. By practicing stoic leadership and maintaining focus, leaders can stabilize their teams and keep moving forward, even in turbulent circumstances.Mental hygiene plays a critical role in maintaining a clear and effective mindset. Coach Reg emphasizes the importance of prioritizing mental well-being and avoiding distractions, particularly from social media, which can introduce chaos and negativity. By focusing on what truly matters and staying grounded, entrepreneurs can enhance their creativity, clarity, and overall effectiveness. For Coach Reg, embracing this disciplined approach to mental health is essential for success in both business and life.About Bob Regnerus (Coach Reg)Bob Regnerus, also known as Coach Reg, is a seasoned marketing coach, author, and speaker with a passion for personal development. With years of experience helping entrepreneurs unlock their potential, Coach Reg uses a holistic approach to coaching, focusing on business, relationships, health, and life purpose. He is the founder of bobregnerus.com, where he offers valuable resources to entrepreneurs seeking guidance in all areas of their lives.About Coach Reg’s Coaching ApproachCoach Reg’s coaching philosophy is rooted in personal connection and tailored support. He prefers one-on-one sessions and small group settings to offer deep, focused attention to each client’s unique needs. His coaching offerings include Spark Sessions, a 90-minute deep dive into specific challenges, and the Full-Day Experience, where clients map out their life goals and create actionable plans to achieve them. Through these personalized sessions, Coach Reg helps individuals clarify their purpose, overcome obstacles, and build a life and business they love.Links Mentioned in this Episode:Visit Coach Reg’s WebsiteCoach Reg on LinkedInEpisode Highlights:How relentless improvement drives both athletes and entrepreneurs to succeedThe importance of dreaming big and visualizing successWhy entrepreneurs should view uncertainty as an opportunity for growthThe significance of mental hygiene for maintaining clarity and creativityHow Coach Reg’s personalized coaching approach helps clients unlock their potentialConclusionThis episode is a must-listen for entrepreneurs who want to elevate their mindset, improve their leadership, and take their personal development to the next level. Coach Reg’s insights into the parallels between sports and entrepreneurship, his approach to navigating uncertainty, and his emphasis on mental well-being make this conversation invaluable for anyone looking to unlock their full potential. Whether you're working on your business or personal growth, the principles Coach Reg shares will help you perform at your best.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Apr 21, 2025 • 19min
2154 - High-Impact Strategies That Turn Marketing Into Sales with Far Beyond Marketing's Amber Gaige
Unlocking the Power of Digital Marketing with Amber GaigeIn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Amber Gaige, the Chief Marketing Advisor and Founder/CEO of Far Beyond Marketing. With over 15 years of experience in the marketing field, Amber shares her expertise on leveraging digital marketing strategies to drive business growth. She reveals the transformative power of Over-The-Top (OTT) advertising and her proven system, "The Four C’s of Effective Marketing," offering entrepreneurs practical insights to elevate their marketing efforts.The Power of OTT Advertising and Data-Driven MarketingAmber opens the conversation by discussing the significant shift in consumer behavior—how more people are now consuming television content online. This change makes it crucial for businesses to establish a strong digital presence. As traditional SEO methods become less effective, Amber emphasizes the importance of leveraging data-driven marketing strategies to stay ahead in a competitive marketplace. She delves into Over-The-Top (OTT) advertising, which allows businesses to target audiences through streaming platforms rather than traditional TV. Amber explains how OTT provides precision targeting, allowing brands to serve ads based on specific demographics, behaviors, and interests, offering an unparalleled opportunity to drive brand growth at a lower cost than traditional TV ads.Crafting Your Brand Story with The Four C’s of Marketing SuccessThroughout the episode, Amber shares her unique framework, The Four C’s of Marketing Success, which has helped hundreds of entrepreneurs clarify their messages and improve their marketing efforts. These pillars include Clear Copy, Consistent Branding, Customer Demographics, and Channel Management. Amber stresses the importance of crafting a clear, compelling narrative through storytelling—something she’s mastered as a certified StoryBrand Guide. Whether you’re working with a large team or just starting out, applying these four principles can help businesses better engage their audience and drive measurable results.About Amber GaigeAmber Gaige is a seasoned marketing strategist and the Founder/CEO of Far Beyond Marketing. With over 15 years of experience, Amber helps businesses across various industries develop digital marketing strategies that drive growth. She is also the author of two books: The Far Beyond Marketing Guidebook and Walking by Faith – Even When It Hurts. Amber’s unique approach combines storytelling with data-driven tactics, helping entrepreneurs connect with their target audiences and achieve measurable success.About Far Beyond MarketingFar Beyond Marketing specializes in helping businesses optimize their marketing strategies through a combination of storytelling, precision targeting, and consistent branding. Amber’s proven system, "The Four C’s of Marketing Success," empowers entrepreneurs to clarify their messaging, build their brand, and drive business growth using data-driven techniques.Links Mentioned in this Episode:Visit Far Beyond MarketingConnect with Amber Gaige on LinkedInMarketing Toolkit: A comprehensive set of tools to enhance your marketing effortsMarketing Quiz: An assessment to evaluate your current marketing strategiesAnnual Planner: A planner to help businesses organize their marketing throughout the yearBook Chapter: A chapter from Amber's bestselling book, providing guidance on navigating the marketing landscapeEpisode Highlights:How OTT advertising is revolutionizing digital marketingAmber’s “Four C’s of Marketing Success” and how they can help clarify your brand messageThe power of storytelling in marketing and how to craft a compelling narrativeThe importance of data-driven decisions in today’s competitive marketing environmentAffordable and effective marketing tactics for businesses of all sizesConclusionThis episode is packed with insights for entrepreneurs looking to level up their marketing strategies. Amber Gaige provides actionable advice on how to use OTT advertising, create a compelling brand story, and implement data-driven marketing tactics to boost business growth. Whether you're a small business owner or a larger enterprise, Amber's proven strategies and unique approach to marketing can help you unlock the full potential of your digital marketing efforts.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Apr 21, 2025 • 25min
2153 - Optimizing Your B2B Website Through A/B Testing with Spiralyze’s Sahil Patel
A/B Testing Strategies and Website Optimization Insights with Sahil PatelIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Sahil Patel, CEO of Spiralyze, a high-performance agency specializing in A/B testing and website optimization. Sahil brings his unique background as a musician and marketer to the conversation, offering powerful insights on how businesses—especially in the B2B space—can dramatically improve their conversion rates by letting data, not guesswork, guide their design decisions.Spiralyze is known for its bold promise: a 30% increase in conversions within 90 days. In this episode, Sahil breaks down the process behind that guarantee, shares lessons from major enterprise projects, and gives actionable advice for business owners and marketers looking to turn their website into a true revenue-generating asset.Why A/B Testing is the Hidden Engine of GrowthSahil explains that while many companies focus on driving traffic to their websites, far fewer pay attention to what happens once users arrive. This is where A/B testing shines. By comparing two versions of a page—whether it's changing a headline, a call-to-action, or even a product image—businesses can make evidence-based decisions that directly impact revenue. Sahil likens the process to a clinical trial: form a hypothesis, run the test, analyze the data, and implement the winner. He emphasizes that even small changes can lead to significant increases in performance—something Spiralyze has proven time and again with clients like Netflix and Pepsi.Lessons in UX, Content Strategy, and Conversion PsychologyFor B2B businesses especially, Sahil points out that the key to better conversions lies in understanding the customer journey. He advises against placing high-production videos on homepages, noting that many users never scroll past the initial hero section. Instead, businesses should place educational content deeper in the site, where visitors are more actively seeking information. He also emphasizes the importance of transparency, including clear pricing and detailed solution pages, and the power of social proof—testimonials and case studies—to build trust and credibility. Sahil’s message is clear: show, don’t just tell, and make your value immediately clear to every visitor.From Creative Instincts to Data-Driven DecisionsSahil’s background as a musician surprisingly informs his approach to optimization. Just as musicians respond to audience energy, marketers must tune into user behavior—and that’s where data plays a starring role. He challenges outdated design conventions, like the use of generic stock photos, and instead recommends showing real products and benefits upfront. Sahil also debunks the overuse of video, advocating for clear messaging and conversion-focused layouts. At the end of the day, the strongest websites are not just visually appealing—they’re built to perform, backed by data, and relentlessly tested.About Sahil PatelSahil Patel is the founder and CEO of Spiralyze, a leading conversion optimization agency helping brands grow through strategic A/B testing. With experience spanning enterprise, mid-market, and startup environments, Sahil brings a unique blend of creativity and analytics to the CRO space.About SpiralyzeSpiralyze specializes in data-driven design and A/B testing for companies looking to increase website conversions. With a focus on B2B and enterprise clients, Spiralyze delivers measurable results—guaranteeing a 30% lift in conversions in just 90 days.Links Mentioned in this Episode:Visit SpiralyzeConnect with Sahil Patel on LinkedInEpisode Highlights:How A/B testing works and why it’s critical for scalingThe biggest mistakes B2B websites make with content and layoutWhy clear messaging outperforms flashy design every timeThe role of user behavior in crafting high-converting experiencesSahil’s unique blend of music and marketing—and how it shapes his strategyConclusionThis episode offers a masterclass in using data to drive smarter marketing. Sahil Patel shares a refreshing and practical approach to CRO that cuts through the noise and focuses on what actually moves the needle. Whether you're a startup founder or an enterprise marketer, you’ll leave this conversation with clear, proven tactics to optimize your website and convert more visitors into customers.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!