The Thoughtful Entrepreneur

The Transformative Power of Whole-Person Mentoring: Lessons from Ryan King of Ardent Mentoring In this episode of The Thoughtful Entrepreneur, host Josh Elledge interviews Ryan King, Co-Founder and CEO of Ardent Mentoring, a nonprofit organization that connects impact-driven entrepreneurs with faith-based mentors. Ryan shares how Ardent’s “whole-person” mentoring approach helps leaders integrate faith, family, and purpose with professional growth. The conversation explores how mentorship can restore balance, build resilience, and inspire generosity in both business and life. Mentoring the Whole Person Ryan explains that true success goes beyond revenue—it’s about becoming the kind of person who can sustain success. Through Ardent Mentoring, leaders are paired with seasoned mentors who focus on faith, family, and identity alongside strategic growth. This holistic approach ensures entrepreneurs don’t just build profitable businesses—they build meaningful lives. He describes how mentorship fosters accountability, vulnerability, and emotional well-being. Entrepreneurs often operate in isolation, but having a trusted guide provides both wisdom and community. Mentors offer perspective not only on business challenges but also on personal development and spiritual alignment. Ryan also emphasizes servant leadership and generosity as cornerstones of sustainable impact. By putting others first, empowering teams, and modeling humility, leaders can create ripple effects of growth and transformation across their organizations and communities. About Ryan King Ryan King is the Co-Founder and CEO of Ardent Mentoring, a nonprofit connecting high-capacity entrepreneurs with faith-driven mentors. With a background in business leadership and spiritual development, Ryan is passionate about helping leaders integrate purpose and performance through whole-person mentoring. About Ardent Mentoring Ardent Mentoring bridges the gap between business success and personal fulfillment. Its mission is to support entrepreneurs through confidential, one-on-one mentoring relationships that integrate professional strategy, faith, and life purpose. Learn more or get involved at ardentmentoring.org. Links Mentioned in This Episode Ryan King on LinkedInArdent Mentoring Website Key Episode Highlights Conclusion Ryan King’s perspective on whole-person mentorship challenges leaders to redefine success—not as achievement alone, but as alignment of purpose, relationships, and service. His work through Ardent Mentoring demonstrates that when leaders grow in both heart and skill, they build businesses that create lasting impact. True transformation begins when we lead with humility, connect with community, and measure success by how much good we do in the world. 🎧 More from UpMyInfluence: 🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here »

The Power of Purpose-Driven Storytelling: Expert Insights from Renee Frojo In this episode of The Thoughtful Entrepreneur, host Josh Elledge interviews Renee Frojo, Founder of A Good Reputation and a leading brand storyteller and content strategist. Renee shares her journey from journalism to entrepreneurship and explains how purpose-driven storytelling helps brands build emotional connections, inspire loyalty, and stand out in a crowded marketplace. Her insights empower business owners and marketers to create narratives that not only attract attention but also drive authentic engagement and trust. Building an Authentic Brand Through Storytelling Renee’s career began in journalism, where she learned the value of clarity, truth, and empathy in communication—skills that now fuel her approach to brand storytelling. She believes that every business has a deeper purpose beyond its products or services, and uncovering that “why” is key to building lasting resonance with customers. Through workshops, interviews, and strategic messaging, Renee helps clients craft stories that humanize their brands and communicate meaning with consistency and confidence. She emphasizes that storytelling is not about marketing spin—it’s about emotional truth. By sharing real experiences and values, businesses can inspire action without relying on sales-driven language. Renee illustrates this through client success stories, such as a small bakery that turned its founder’s personal journey into a powerful brand mission about resilience and second chances. Renee also encourages entrepreneurs to prioritize rest and intentional reflection as part of the creative process. Taking time to recharge—something she personally practices through travel and mindfulness—fuels fresh perspectives and long-term creativity. Building a purposeful business means designing space for both inspiration and sustainability. About Renee Frojo Renee Frojo is a brand storyteller, content strategist, and founder of A Good Reputation, where she helps purpose-driven companies clarify their messaging, strengthen their reputations, and tell stories that connect deeply with their audiences. Drawing from her background in journalism and marketing, she bridges authenticity and strategy to help brands grow through the power of story. About A Good Reputation A Good Reputation is a strategic storytelling consultancy that works with entrepreneurs, startups, and established brands to develop authentic narratives, content strategies, and messaging frameworks. The firm’s mission is to help businesses communicate with empathy and purpose, fostering connection and credibility in every story they tell. Learn more at agoodreputation.com. Links Mentioned in This Episode Renee Frojo on LinkedInA Good Reputation Website Key Episode Highlights Conclusion Renee Frojo’s approach reminds us that effective branding starts with empathy, self-awareness, and storytelling rooted in purpose. When businesses tell stories that reflect their values and impact, they don’t just stand out—they inspire...

Navigating Payroll and HR in the Cannabis Industry: Insights from Marc Rodriguez of Green Leaf Payroll & Business Solutions Inc. The cannabis and hemp industries are growing rapidly but face some of the most complex compliance and regulatory challenges in business today. In this episode, host Josh Elledge speaks with Marc Rodriguez, Co-founder and CEO of Green Leaf Payroll & Business Solutions Inc., about how cannabis companies can overcome payroll, HR, and benefits hurdles. Marc shares how his firm helps businesses navigate industry-specific issues like federal restrictions, Section 280E taxation, and labor peace agreements—offering a roadmap for building compliant, scalable operations. Building Compliance and Resilience in a Complex Industry Marc explains that cannabis companies operate in an environment where traditional payroll providers often refuse service, leaving them vulnerable. Green Leaf was founded to fill that gap—helping businesses stay compliant while managing payroll, HR, and benefits seamlessly across vertically integrated operations. The company’s experience in taxation, union reporting, and state-specific labor requirements allows clients to focus on growth rather than administrative chaos. Beyond compliance, Marc draws parallels between his personal CrossFit discipline and business health, stressing that consistent “maintenance” is key. Just as injury prevention requires intentional effort, so does building a company that can weather regulatory shifts and operational challenges. Green Leaf’s approach blends proactive compliance with strategic consulting, ensuring clients have both protection and flexibility. He also emphasizes technology and leadership involvement in decision-making. From implementing user-friendly HR platforms to developing transparent 401(k) options for cannabis employees, Green Leaf helps clients elevate both operations and culture. Marc encourages CEOs to view HR and payroll as strategic assets, not afterthoughts, and to surround themselves with specialized partners who understand their industry’s nuances. About Marc Rodriguez Marc Rodriguez is the Co-founder and CEO of Green Leaf Payroll & Business Solutions Inc., specializing in payroll, HR, benefits, and recruiting solutions for the cannabis and hemp industries. A recognized leader in regulated markets, Marc is passionate about helping business owners build compliant, efficient, and sustainable organizations through expertise and transparency. About Green Leaf Payroll & Business Solutions Inc. Green Leaf Payroll & Business Solutions Inc. provides comprehensive HR, payroll, and benefits services tailored specifically for cannabis and hemp businesses. The company partners with clients across cultivation, manufacturing, and retail to streamline operations, ensure compliance, and manage growth effectively. Learn more at greenleafbizsolutions.com. Links Mentioned in This Episode Marc Rodriguez on LinkedInGreen Leaf Payroll & Business Solutions Inc. Key Episode Highlights

How AI and No-Code Tools Are Transforming Business: Insights from Sean Weisbrot of We Live to Build Technology is evolving faster than ever, and businesses that don’t adapt risk falling behind. In this episode, host Josh Elledge interviews Sean Weisbrot, Founder and CEO of We Live to Build, to explore how artificial intelligence and no-code tools are revolutionizing business operations and software development. Sean, who has interviewed more than 260 founders and investors, shares powerful insights on how these tools are reshaping entrepreneurship, empowering non-technical founders, and creating scalable opportunities for growth. Building Smarter, Faster, and More Accessible Businesses Sean explains that AI is not just improving efficiency—it’s transforming how companies think and operate. From automating manual processes to enabling rapid data-driven decision-making, AI is now a core component of modern business strategy. Sean also discusses the mindset shift among founders who are embracing automation and using AI as a strategic partner, not just a productivity tool. He introduces the concept of “vibe coding,” where AI is used to build and iterate software faster than ever before. Through tools like Cursor, Lovable, and Bubble, founders can now develop full-fledged applications in days, eliminating traditional barriers to innovation. These no-code and low-code platforms are democratizing access to technology, allowing visionaries without deep technical backgrounds to test ideas and build products with speed and confidence. Sean emphasizes that while AI agents and automation offer incredible potential, success depends on customization, trusted implementation, and ethical use. He warns against one-size-fits-all solutions and stresses the importance of choosing partners who understand your business goals. His message to founders is clear—stay curious, experiment boldly, and use technology to create meaningful, scalable impact. About Sean Weisbrot Sean Weisbrot is the Founder and CEO of We Live to Build, a media and consulting platform focused on empowering entrepreneurs through AI, automation, and community. As a serial entrepreneur and host of the We Live to Build podcast, Sean has interviewed hundreds of founders, executives, and innovators, distilling their lessons into actionable insights for business leaders worldwide. About We Live to Build We Live to Build is an entrepreneurial education platform and podcast that helps founders grow, automate, and scale their businesses using modern technology. The brand offers interviews, tutorials, and consulting focused on AI, no-code development, and business systems that drive sustainable growth. Learn more at welivetobuild.com. Links Mentioned in This Episode Sean Weisbrot on LinkedInWe Live to Build Website Key Episode Highlights Conclusion AI and no-code platforms are opening new doors for innovation, scalability, and entrepreneurship. As Sean Weisbrot explains, success in this new era comes from pairing curiosity with strategy—using tools wisely,...

How to Scale and Exit Your Business the Right Way: In-Depth Insights from Josh Davis Many founders and CEOs find themselves caught in the day-to-day grind, unsure how to grow their business sustainably—or how to prepare for an eventual exit. In this episode, host Josh Elledge interviews Josh Davis, five-time founder, Chairman and CEO of JL Davis Enterprises, and one of Canada’s Top 40 Under 40. Drawing from his own entrepreneurial journey and experience selling a fast-growing logistics company, Josh shares a step-by-step guide for scaling, systemizing, and ultimately creating a business that can thrive independently of its founder. Building for Scalability and Exit Success Josh emphasizes that every entrepreneur should build their business as if they plan to sell it, even if they never do. A “sale-ready” company—one with clear processes, reliable systems, and strong leadership—is not only more valuable to buyers but also far easier to manage. Founders who invest early in documentation, automation, and leadership development create companies that can grow sustainably and operate smoothly without their constant involvement. A critical part of scaling is having the right people in the right roles. Josh explains that businesses often plateau because of leadership gaps or founder dependency. He recommends regularly auditing your organizational structure, empowering key hires, and fostering a culture of ownership across all levels. By delegating effectively, founders free themselves to focus on strategy rather than daily operations. When it comes to exits, planning years in advance is key. The best outcomes happen when founders clean up financials early, minimize founder reliance, and work with experienced advisors well before they’re ready to sell. Josh’s firm helps business owners navigate this process, whether they’re preparing for acquisition, seeking investors, or simply aiming for a more autonomous company. About Josh Davis Josh Davis is a five-time founder and the Chairman & CEO of JL Davis Enterprises, where he helps entrepreneurs scale and position their businesses for successful exits. Recognized as one of Canada’s Top 40 Under 40, Josh has led multiple ventures in logistics, consulting, and investment, combining hands-on leadership with a passion for mentorship and sustainable business growth. About JL Davis Enterprises JL Davis Enterprises partners with founders and CEOs to optimize growth, streamline operations, and prepare businesses for sale or succession. The firm offers consulting, advisory, and acquisition services designed to help companies become more scalable, profitable, and self-sufficient. Learn more and access free resources at jldavisenterprises.com. Links Mentioned in This Episode Josh Davis on LinkedInJL Davis Enterprises Website Key Episode Highlights Conclusion Scaling and exiting a business successfully requires vision, structure, and discipline. As Josh Davis...

Unlocking E-Commerce Success: Expert Insights on Shopify, AI, and B2B with Mac King of Domaine In today’s fast-changing digital landscape, success in e-commerce requires more than great products—it demands innovation, strategy, and adaptability. In this episode, host Josh Elledge interviews Mac King, Co-Founder and Chief Revenue Officer of Domaine, a leading Shopify agency, to explore the latest trends transforming online retail. From the power of AI-driven shopping and B2B growth on Shopify to the revival of branded mobile apps, Mac shares proven strategies for brands aiming to elevate their digital presence and thrive in 2025 and beyond. How AI and Shopify Are Reshaping the Future of E-Commerce Mac King emphasizes that artificial intelligence is revolutionizing how consumers discover, compare, and purchase products. AI-powered assistants like ChatGPT are becoming personal shopping guides, meaning brands must optimize their Shopify stores for visibility in these new AI-driven discovery channels. Structured data, schema markup, and detailed product descriptions are no longer optional—they’re essential for ensuring your brand appears in AI-generated recommendations. Beyond search, AI also enables personalization that rivals the in-store experience. With tools that track preferences, sizes, and purchase histories, online retailers can now deliver tailored recommendations, dynamic content, and real-time support. Mac advises brands to think like a trusted in-store associate: anticipate customer needs, use data wisely, and make every online interaction feel personal. He also highlights Shopify’s growing role in the B2B space. With new features such as wholesale portals, custom pricing, and ERP integrations, Shopify empowers businesses to serve both direct consumers and trade buyers from a single platform. Combined with the resurgence of branded mobile apps—offering direct engagement through push notifications and loyalty rewards—these innovations position brands for long-term growth and customer retention. About Mac King Mac King is the Co-Founder and Chief Revenue Officer (CRO) of Domaine, where he leads revenue strategy and client partnerships. With years of experience in digital commerce and Shopify development, Mac helps brands integrate technology, storytelling, and customer experience to drive measurable growth. His expertise spans DTC, B2B, and omnichannel strategy. About Domaine Domaine is a top-rated Shopify Plus agency specializing in strategy, design, and custom development for growing e-commerce brands. The company partners with clients across industries to optimize digital storefronts, streamline backend systems, and create seamless, revenue-driving customer experiences. Learn more at meetdomaine.com. Links Mentioned in This Episode Mac King on LinkedInDomaine Website Key Episode Highlights Conclusion The future of e-commerce is intelligent, integrated, and deeply personal. As Mac King explains, embracing AI, optimizing for new discovery channels,...

Mastering Personal Branding in the Age of AI: Insights from Lauren Davis In a world increasingly shaped by digital visibility and AI-driven search, personal branding has become a necessity—not a luxury. In this episode, host Josh Elledge interviews Lauren Davis, Founder of Lauren Davis Creative, who shares her five-step framework for building an authentic, memorable, and future-proof personal brand. From storytelling and search visibility to nurturing community and staying adaptable, Lauren offers actionable advice for professionals and entrepreneurs who want to stand out and connect meaningfully in 2024 and beyond. Building a Personal Brand That Grows with You Lauren Davis’s approach to personal branding is rooted in intentionality and authenticity. Drawing on her experience as a record store owner turned branding consultant, she emphasizes that branding isn’t about perfection—it’s about connection. Every interaction online contributes to your personal narrative, and managing that narrative proactively ensures your audience sees the real you. Her five-step process begins with being findable online—optimizing search results, claiming your digital space, and differentiating your name or identity. Next, she highlights curating your brand experience: ensuring your website, visuals, and messaging reflect who you are today. From there, it’s about nurturing relationships through value-driven content, genuine engagement, and consistent communication. Lauren also underscores the power of storytelling, urging professionals to build community through shared experiences. Finally, she recommends auditing your brand regularly to stay relevant as trends, technology, and your personal goals evolve. Lauren points out that AI is reshaping how personal brands are discovered, with search engines and chatbots pulling from public content to form impressions. To stay ahead, professionals must be proactive—keeping profiles current, managing reputation across platforms, and using keywords and narratives that align with how they want to be found. The key takeaway? A personal brand isn’t built overnight; it’s cultivated through clarity, consistency, and connection over time. About Lauren Davis Lauren Davis is a personal branding strategist, speaker, and Founder of Lauren Davis Creative, where she helps entrepreneurs and professionals build impactful, human-centered brands. Known for her practical frameworks and genuine approach, Lauren has guided thousands of clients in defining their identity, refining their messaging, and increasing visibility through storytelling, strategy, and community building. She is also the host of The Real Personal Branding Podcast. About Lauren Davis Creative Lauren Davis Creative is a brand development and personal growth consultancy helping professionals and business owners establish and evolve their digital presence. The firm’s mission is to empower clients to take control of their narrative through personalized brand strategy, visibility coaching, and creative storytelling that authentically connects with audiences. Links Mentioned in This Episode Lauren Davis on LinkedInLauren Davis Creative Website Key Episode Highlights

Mastering LinkedIn in 2024: Expert Strategies from MAIA Digital LinkedIn has become more than just a job-hunting platform—it’s now the go-to space for business growth, personal branding, and professional influence. In this episode, host Josh Elledge interviews Shay Thieberg and Eli Igra Serfaty, co-founders of MAIA Digital, to discuss how individuals and companies can maximize their visibility and results on LinkedIn. They explore the platform’s latest features, user behavior trends, and actionable strategies that turn casual networking into meaningful business opportunities. The Future of LinkedIn: Engagement, Authenticity, and Opportunity According to Shay and Eli, LinkedIn has evolved into a powerful ecosystem for professionals, executives, and business owners who want to establish thought leadership. Unlike other social platforms, most LinkedIn users are senior decision-makers—and yet only 1% create content. This creates a huge opportunity for consistent, authentic voices to stand out and build authority. The duo emphasizes that engagement is the new currency on LinkedIn. Thoughtful comments and conversations often generate more visibility than standalone posts, as they demonstrate credibility and spark genuine interaction. They also discuss LinkedIn Sales Navigator as a high-ROI tool when used to build relationships instead of sending mass messages. In addition, features like LinkedIn newsletters and optimized company pages are underused assets that can rapidly expand reach, SEO visibility, and brand trust. Ultimately, Shay and Eli highlight that success on LinkedIn requires consistency, community, and clarity of purpose. Whether you’re growing a business, nurturing partnerships, or positioning yourself as an industry expert, being authentic, data-informed, and strategically visible are the keys to long-term impact on the platform. About MAIA Digital MAIA Digital is a LinkedIn-first marketing and branding agency founded by Shay Thieberg and Eli Igra Serfaty. The agency specializes in helping founders, executives, and companies amplify their presence through optimized content strategies, profile makeovers, and engagement-driven growth campaigns. MAIA Digital’s mission is to help professionals move from passive users to active influencers who attract business organically. About Shay Thieberg & Eli Igra Serfaty Shay Thieberg and Eli Igra Serfaty are LinkedIn growth experts and co-founders of MAIA Digital. With backgrounds in marketing, communications, and business development, they help clients convert online visibility into real-world opportunity. Together, they’ve developed frameworks that merge analytics, psychology, and storytelling to help professionals grow faster and more authentically on LinkedIn. Links Mentioned in This Episode Shay Thieberg on LinkedInEli Igra Serfaty on LinkedIn Key Episode Highlights Conclusion The insights shared by Shay and Eli make one thing clear:...

How to Build a High-Performing Sales Team in a Founder-Led Business: Insights from Nicholas Loise For many small and midsize business owners, sales can be both the engine and the bottleneck of growth. Founder-led sales will only take a company so far before scalability demands process, structure, and leadership. In this episode, host Josh Elledge speaks with Nicholas Loise, Founder of Sales Performance Team, who shares practical strategies for transitioning from founder-driven selling to building a high-performing, self-sustaining sales organization. Building a Scalable Sales System Nicholas Loise explains that most founders struggle with hiring salespeople because they underestimate how different it is to sell for a small business compared to a large enterprise. Without the backing of a big brand, sales success depends on grit, creativity, and adaptability. He emphasizes that before hiring, founders must document their entire sales process—from prospecting and discovery to objection handling and closing—so new hires have a clear roadmap to follow. Once the playbook is in place, Nicholas recommends hiring two salespeople at once to increase the chances of success, benchmark performance, and encourage healthy collaboration. He also stresses the importance of investing heavily in the first 90 days, creating structured onboarding, shadowing opportunities, and clear milestones to ensure quick ramp-up and retention. Compensation should be simple and transparent, typically a mix of base salary plus commission that motivates results while providing stability during onboarding. Finally, Nicholas discusses how to maintain oversight without micromanaging. Delegating sales effectively requires trust—but also process. Regular reviews, feedback loops, and continuous updates to your playbook keep the system strong. By using objective assessment tools and focusing on cultural fit, founders can build sales teams that scale sustainably and deliver consistent performance long after they’ve stepped out of the front-line role. About Nicholas Loise Nicholas Loise is the Founder of Sales Performance Team and a seasoned sales strategist who helps founder-led businesses build scalable, high-performing sales teams. With decades of experience in sales leadership, Nicholas specializes in designing sales playbooks, recruiting and onboarding top-performing reps, and aligning compensation structures that drive profitable growth. About Sales Performance Team Sales Performance Team helps $1M–$25M companies transition from founder-led selling to a system-driven sales organization. The firm provides fractional sales leadership, sales team recruitment, onboarding systems, compensation design, and proven frameworks that help founders replace intuition with strategy—and build a sales team that consistently delivers results. Links Mentioned in This Episode Sales Performance Team WebsiteNicholas Loise LinkedIn Profile Key Episode Highlights

Navigating Digital Transformation in Construction: Expert Insights from Huw Roberts, CEO of PMWEB The construction industry is evolving at a critical pace—balancing traditional processes with the rise of AI, automation, and digital transformation. In this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Huw Roberts, CEO of PMWEB, to discuss how construction firms can modernize operations, improve efficiency, and adopt outcome-driven technology strategies. Huw shares actionable insights for leaders navigating uncertainty, highlighting the need for clear goals, practical innovation, and consistent learning to build resilient, future-ready organizations. The Digital Shift in Construction The construction industry is one of the largest in the world but also among the slowest to digitize. Huw Roberts explains that while many sectors have embraced automation and AI, much of construction still depends on manual workflows, spreadsheets, and outdated systems. This creates inefficiencies that technology can help solve—if applied with purpose. Huw stresses that digital transformation isn’t about adopting the latest tool; it’s about aligning technology with specific outcomes. Whether the goal is faster project delivery, better collaboration, or improved forecasting, success starts with defining measurable results and working backward from there. Companies should begin with small pilot projects, gather feedback, and scale successful initiatives across the organization. Ultimately, balancing innovation with caution is essential. Large enterprises can absorb the risks of experimentation, while small and mid-sized businesses must focus on clear returns. By adopting an outcome-focused mindset and continuously learning from both wins and failures, construction firms can achieve meaningful transformation without sacrificing stability. About Huw Roberts Huw Roberts is the CEO of PMWEB, where he leads a global team dedicated to transforming how organizations plan, manage, and deliver construction and real estate projects. With a background in architecture and decades of experience in technology leadership, Huw bridges design, innovation, and business strategy to help clients improve performance and embrace the digital future of project management. About PMWEB PMWEB is a leading enterprise software platform that streamlines construction and real estate portfolio management. Designed for performance and transparency, PMWEB equips organizations with the tools to manage costs, schedules, and outcomes through data-driven decision-making. The company’s integrated approach enables project teams to operate more efficiently and deliver measurable business results. Links Mentioned in This Episode Huw Roberts LinkedInPMWEB Website Key Episode Highlights Conclusion Huw Roberts’ insights reveal that digital transformation in construction isn’t just about technology—it’s about clarity, adaptability, and purpose. By focusing on measurable outcomes, leveraging AI strategically, and empowering teams with the right tools, leaders can drive lasting...

Building a High-Performance Workplace Culture: Insights from Matthew Person’s “Four I’s” Methodology In this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Matthew Person, business strategist, M&A advisor, and Founder & Managing Director of Town Square Business Advisors. Matthew shares his framework for building a high-performance workplace culture—one that blends structure with freedom and aligns values with execution. His “Four I’s” methodology—Identity, Instruction, Intercommunication, and Information Feedback—helps companies create environments where clarity, collaboration, and accountability thrive. Rethinking Culture: The Four I’s Framework Matthew Person explains that too many companies try to copy “Best Places to Work” models without understanding what makes their own teams unique. He emphasizes that culture is not about perks or imitation—it’s about clarity of purpose and alignment with organizational identity. The first pillar, Identity, defines who you are as a company and why you exist, serving as a foundation for decisions, relationships, and results. The next two pillars, Instruction and Intercommunication, address how organizations operate and communicate. Instruction provides structure—ensuring that processes, roles, and expectations are clear—while intercommunication builds trust by encouraging open, consistent dialogue. When both elements are strong, teams move cohesively, information flows effectively, and leaders can focus on strategy rather than micromanagement. Finally, Information Feedback turns culture into a living, adaptive system. Feedback, Matthew explains, should be consistent, transparent, and actionable—not reserved for annual reviews. Together, the Four I’s create what he calls constrained independence—a balance between freedom and boundaries that empowers innovation without chaos. The result is a culture that performs with purpose, resilience, and shared accountability. About Matthew Person Matthew Person is the Founder and Managing Director of Town Square Business Advisors, where he works with executives and business owners to enhance strategy, leadership, and organizational culture. With decades of experience in mergers, acquisitions, and business growth advisory, Matthew developed the Four I’s framework to help leaders build clarity, cohesion, and confidence into every level of their company. About Town Square Business Advisors Town Square Business Advisors partners with business leaders and organizations to create sustainable growth through strategic clarity, operational excellence, and people-centered culture. The firm specializes in M&A advisory and executive consulting, helping companies align their leadership, systems, and communication for long-term success. Links Mentioned in This Episode Matthew Person on LinkedIn:https://www.linkedin.com/in/matthewdperson/Town Square Business Advisors:www.townsquare-advisors.com Key Episode Highlights Four I’s

Building Authentic Connections: Daniel Andrews on Friendship, Hospitality, and Low-Barrier Networking In this episode of The Thoughtful Entrepreneur, host Josh Elledge talks with Daniel Andrews, serial entrepreneur, connector, and mentor, about transforming both personal and professional relationships through authenticity and intentional hospitality. Daniel shares how small, simple actions—like inviting people over for dinner or scheduling short, genuine networking calls—can create powerful, lasting connections. His approach replaces the pressure of traditional networking with openness, generosity, and genuine curiosity, helping people connect more meaningfully in an increasingly digital world. Building Relationships Through Simplicity and Hospitality Daniel Andrews believes that hospitality is not about perfection but presence—making people feel seen, valued, and welcomed. He and his wife regularly host dinners to strengthen friendships, emphasizing that consistency and simplicity make connection sustainable. Whether in business or personal life, Daniel says hospitality creates space for trust, conversation, and belonging. Beyond hosting, Daniel encourages using technology to remove barriers to connection. He creatively uses Calendly for dinner invites, allowing friends to pick a convenient date and eliminating the friction of group planning. His philosophy: make it easy for people to say “yes” by lowering the stakes and setting clear expectations. Daniel also applies these principles to business networking. Instead of formal sales meetings, he prefers 20-minute, no-pressure “get-to-know-you” calls that prioritize relationship-building over pitching. He calls introductions the “currency of trust,” explaining that when you thoughtfully connect two people, you share your credibility and strengthen all three relationships. For Daniel, connection is not about collecting contacts—it’s about building a network of genuine, mutually beneficial relationships. About Daniel Andrews Daniel Andrews is a seasoned entrepreneur, mentor, and relationship builder who champions authentic connection in both business and life. Known for his thoughtful approach to hospitality and low-barrier networking, Daniel has helped countless leaders and entrepreneurs strengthen relationships, expand their communities, and find deeper fulfillment through intentional connection. Links Mentioned in This Episode Daniel Andrews on LinkedIn Key Episode Highlights presenceCalendlyshort, intentional conversations Conclusion Daniel Andrews reminds us that meaningful connection doesn’t require grand gestures—it starts with small acts of intentionality. By simplifying invitations, embracing hospitality, and focusing on authenticity over perfection, we can nurture relationships that enrich both business and life. Genuine networking isn’t about volume; it’s about trust, presence, and care. 🎧 More from UpMyInfluence: 🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your story in front of 50,000+ listeners. 👉 Schedule your guest spot here. 🤝 Consultant or agency doing 6+ figures? Let us

How Business Owners Can Scale and Thrive in the Age of AI: Insights from Dan Goodstein In this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Dan Goodstein, Founder of The Business Therapist and President of IRPA AI, to explore how business owners can scale smarter and thrive amid rapid technological change. With years of experience in tech, marketing, media, and coaching, Dan offers practical advice on leveraging AI, building community, and creating systems that support sustainable growth in today’s fast-paced environment. Scaling Smarter in the AI Era Dan emphasizes that too many business owners are working in their businesses rather than on them. He highlights the importance of stepping back, joining peer communities, and embracing outside accountability through coaching or masterminds. These practices create space for strategy, innovation, and balance—especially critical as AI reshapes how we work. AI, he explains, is now leveling the playing field for small and midsize businesses, giving them access to tools once reserved for large corporations. From AI-driven sales assistants to automated lead generation and CRM integrations, these technologies help streamline operations, enhance personalization, and improve ROI. Dan also encourages owners to adopt a “pilot-first” approach—testing tools on a small scale before company-wide implementation to ensure measurable results. Finally, Dan shares actionable strategies for using AI in sales, from automating outreach to personalizing follow-ups, while maintaining the human connection that drives lasting relationships. His advice is clear: start small, stay consistent, and focus on impact over volume. AI isn’t about replacing people—it’s about empowering them to spend more time on high-value, strategic work. About Dan Goodstein Dan Goodstein is the Founder of The Business Therapist, a platform helping entrepreneurs build scalable, resilient companies through coaching, peer networks, and strategic support. He also serves as President of IRPA AI, a global association focused on intelligent automation and digital transformation. Dan is the host of The Digital Leader Show and a frequent speaker on AI, business growth, and leadership innovation. About The Business Therapist The Business Therapist provides business owners with the community, coaching, and resources they need to scale sustainably. Through mastermind groups, advisory programs, and peer-to-peer learning, the organization helps leaders step back from daily operations to focus on vision, systems, and growth strategy. Links Mentioned in This Episode The Business Therapist WebsiteIRPA AI WebsiteDan Goodstein LinkedIn Profile Key Episode Highlights Conclusion Dan Goodstein’s message is simple but powerful: you can’t scale by doing more—you scale by doing smarter. By stepping back, building support systems, and embracing AI-driven tools, business owners can transform the way they grow and operate. The future belongs to leaders...

Building B2B Authority in the AI Era: Actionable Strategies from Kathleen Lucente of Red Fan Communications In this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Kathleen Lucente, Founder and CEO of Red Fan Communications, to explore how B2B companies can build lasting authority and credibility in the AI-driven digital landscape. Kathleen shares her expertise in modern PR, brand storytelling, and thought leadership, offering a roadmap for high-growth companies to adapt to the era of zero-click searches and AI-powered visibility. Building B2B Authority in the Age of AI Kathleen explains that traditional SEO strategies are no longer enough. With nearly 60% of Google searches ending without a click, brands must now focus on being discoverable through AI summaries, thought leadership, and digital authority—not just website traffic. She introduces her “Revenue Bridge” framework, built around three pillars: authority, credibility, and reputation. Authority opens doors, credibility converts, and reputation sustains long-term growth. To stand out in this new environment, Kathleen encourages businesses to refresh their brand narratives, ensuring they reflect what truly differentiates them in the market. She emphasizes multi-channel storytelling and the importance of developing multiple internal thought leaders who can each represent distinct aspects of a company’s expertise. The goal isn’t just visibility—it’s being referenced, quoted, and trusted by both humans and AI systems alike. Finally, she underscores that thought leadership is now a direct revenue driver. By educating your audience, securing media coverage, and engaging authentically online, companies can strengthen their digital footprint and boost conversions. Kathleen’s message is clear: in the AI era, influence happens before the click. B2B leaders must build public credibility that algorithms and audiences alike can recognize and trust. About Kathleen Lucente Kathleen Lucente is the Founder and CEO of Red Fan Communications, a strategic communications firm based in Austin, Texas. With over two decades of experience, she has helped startups and Fortune 500 companies alike transform their PR and marketing strategies. Her firm specializes in brand narrative development, executive thought leadership, and communications strategies that drive measurable business growth. About Red Fan Communications Red Fan Communications is a full-service strategic communications agency that helps high-growth B2B companies stand out in crowded markets. The firm partners with clients to elevate authority, strengthen reputation, and connect PR efforts directly to revenue. Through storytelling, content strategy, and media relations, Red Fan ensures brands remain relevant, discoverable, and influential in the AI-powered age. Links Mentioned in This Episode Red Fan Communications WebsiteKathleen Lucente LinkedIn Key Episode Highlights Conclusion Kathleen Lucente’s insights reveal that building authority today means adapting to the invisible influence of AI. By...

Mastering Productivity: How to Treat Time Like Cash and Build Sustainable Success In this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Andrew Hartman, Founder and CEO of Time Boss, to explore a transformative approach to productivity. Andrew challenges the traditional hustle mindset, advocating instead for sustainable focus, intentional time management, and a “time-as-cash” philosophy. Their discussion reveals how leaders can achieve meaningful results by aligning energy, setting boundaries, and working smarter—not harder. Rethinking Productivity: Sustainability Over Hustle Andrew explains that productivity isn’t about staying busy—it’s about getting the right things done. He encourages founders and executives to treat time like a limited resource, allocating it intentionally toward high-impact work. By setting a weekly “time budget,” business leaders can prioritize key results, prevent burnout, and maintain clarity around what truly matters. He also highlights the importance of sustainability over short-term sprints. Hustle can drive short bursts of progress, but without recovery, it leads to exhaustion. Instead, Andrew recommends anchoring to a steady baseline of work hours and recharging regularly to stay consistent. He reminds leaders that “boundaries aren’t restrictive—they’re empowering.” The discipline of protecting your time actually frees you to focus more deeply on creative and strategic work. Lastly, Andrew emphasizes the power of working in your zone of genius—the tasks that energize you and align with your strengths. Delegating draining work and using simple, familiar tools for time management (like a calendar or to-do list) can dramatically boost both productivity and satisfaction. True efficiency, he says, comes not from shiny new apps, but from consistent habits and clear priorities. About Andrew Hartman Andrew Hartman is the Founder and CEO of Time Boss, a productivity training company that helps entrepreneurs and executives design intentional, sustainable schedules for success. With years of experience coaching business owners, Andrew has developed frameworks like “time-as-cash” and “intentional time budgeting” to help clients achieve more by doing less—without burnout. About Time Boss Time Boss is a coaching and training platform dedicated to helping professionals reclaim their time and focus on meaningful results. Through masterclasses, workshops, and personalized consulting, Time Boss equips individuals and teams to set clear priorities, align their energy with their goals, and create balance between work and life. Links Mentioned in this Episode Time Boss WebsiteAndrew Hartman LinkedIn Profile Key Episode Highlights Conclusion Andrew Hartman’s insights remind us that success isn’t built on endless work—it’s built on intention, focus, and balance. By treating time as your most valuable currency, setting boundaries, and operating in your strengths, you can create both sustainable productivity and a fulfilling lifestyle. 🎧 More from UpMyInfluence: 🎙️ Want to be featured on The Thoughtful Entrepreneur?...

Mastering B2B Lead Generation in the Age of AI: Expert Insights from Bill Rice In this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Bill Rice, founder of Bill Rice Strategy Group and Kaleidico. Bill shares his expertise in B2B marketing, lead generation, and the evolving role of AI in shaping how businesses attract and convert clients. Drawing from decades of experience in fintech, mortgage lending, and legal industries, Bill offers actionable insights for executives and agencies looking to thrive in a rapidly changing digital landscape. The New Rules of B2B Lead Generation Bill explains that B2B marketing has evolved beyond traditional methods like cold outreach and Google Ads. Today’s success depends on creating digital surface area—the online footprint of content, profiles, and engagement that helps AI and algorithms recognize your expertise. He emphasizes that consistent, clear messaging across blogs, websites, and social platforms allows both search engines and large language models (like ChatGPT) to identify and recommend your brand as an authority. A key part of Bill’s strategy is leveraging LinkedIn for executive visibility. He encourages business leaders to post regularly, engage thoughtfully, and use the platform as a stage for thought leadership. Sharing authentic stories, insights, and industry perspectives humanizes your brand while establishing credibility. This kind of visibility not only attracts potential clients but also builds trust and familiarity long before the sales conversation begins. Bill also discusses how AI and large language models are reshaping the buyer’s journey. AI-driven referrals are becoming more influential than traditional SEO, as they provide context-aware recommendations tailored to user needs. He advises business owners to ensure their digital content is well-structured, easy to interpret, and consistently reinforces their niche expertise. By combining thoughtful content creation, AI awareness, and genuine personal branding, companies can build scalable, first-party lead generation systems that produce sustainable results. About Bill Rice Bill Rice is the Founder of Bill Rice Strategy Group and Kaleidico, two leading agencies specializing in B2B marketing and lead generation. With over 20 years of experience across finance, law, and senior living sectors, Bill helps executives and organizations develop first-party lead systems, optimize digital presence, and harness AI for measurable business growth. He is also the creator of The Executive Brief, a weekly newsletter featuring actionable insights for leaders navigating the intersection of marketing and technology. About Bill Rice Strategy Group Bill Rice Strategy Group is a marketing consultancy that helps businesses build first-party lead generation systems through strategy, content creation, and AI-driven insights. With a focus on long-term growth and client ownership of marketing assets, the firm empowers organizations to elevate their brand authority, generate consistent leads, and adapt to the rapidly evolving digital landscape. Links Mentioned in this Episode Bill Rice Strategy GroupBill Rice LinkedIn ProfileThe Executive Brief Newsletter Key Episode Highlights

Realigning Your Business with Passion: Expert Insights from Kara Duffy In this episode of The Thoughtful Entrepreneur, host Josh Elledge interviews Kara Duffy, CEO and Founder of KDCC International, who helps entrepreneurs and business owners realign their work with their passions and strengths. Kara shares how reconnecting with what you love can reignite purpose, boost profitability, and prevent burnout. Through her experience coaching creative leaders and building businesses, she offers clear, actionable steps to simplify operations, find your “zone of genius,” and create a company that feels as good as it performs. Building a Passion-Aligned Business Kara believes that success starts with alignment—when your business reflects your purpose and energizes you daily. She explains that many entrepreneurs drift from their passion over time, taking on clients or projects that drain creativity and joy. Her “lemonade stand” philosophy encourages founders to strip back to what they do best and build from that foundation. By focusing on a single core offering, simplifying operations, and delegating distractions, business owners can regain clarity, increase profitability, and rediscover fulfillment in their work. Operating in your “zone of genius,” Kara says, means spending most of your time on high-value, joyful activities. She urges leaders to delegate or eliminate everything outside that zone and to audit weekly tasks for alignment. Through this lens, even niche businesses—like boutique creatives or specialists serving small, passionate audiences—can thrive when they stay authentic and focused. When clarity replaces clutter, it becomes easier to attract dream clients who align with your mission and values. Kara also emphasizes that business is a lifestyle, not just a job. She encourages entrepreneurs to design companies that support their personal rhythms and long-term well-being. Whether it’s taking “mini holidays” to recharge or fostering genuine client relationships, the goal is to create a sustainable balance. Her signature mantra—“Stop Selling, Start Sharing”—captures her belief that authenticity and generosity are the true engines of business growth. When you lead with purpose and share what you love, success follows naturally. About Kara Duffy Kara Duffy is the CEO and Founder of KDCC International, a business coaching and consulting firm dedicated to helping entrepreneurs and creative leaders build businesses that are both profitable and purposeful. With extensive experience guiding founders through growth and realignment, Kara helps clients simplify, scale, and reconnect with their mission. She is also the author of Stop Selling, Start Sharing, a guide to authentic, purpose-driven business. About KDCC International KDCC International empowers entrepreneurs and teams to build high-impact, passion-driven businesses through strategic coaching, workshops, and consulting. From clarity and culture to profitability and purpose, KDCC helps leaders align their operations with their vision—creating companies that thrive from the inside out. Links Mentioned in this Episode KDCC InternationalKara Duffy LinkedIn Profile Key Episode Highlights Conclusion As Kara Duffy reminds us, business success isn’t just about growth—it’s about alignment. When your...

When Is Your Business Ready for a Fractional CFO? Expert Insights from Laresa McIntyre As your business scales, the financial landscape becomes increasingly complex. Many founders find themselves overwhelmed by cash flow management, forecasting, and financial decision-making—realizing their passion alone isn’t enough to sustain growth. In this episode, host Josh Elledge interviews Laresa McIntyre, fractional CFO and Founder of Rockbridge CFO, who shares her insights on when to bring in a fractional CFO, how to prepare for that step, and how doing so can transform your business operations and confidence. The Right Time to Hire a Fractional CFO Laresa explains that a fractional CFO is a part-time financial executive who provides strategic planning, forecasting, and financial insight—without the cost of a full-time hire. Businesses typically benefit when revenue reaches the $1M–$2M mark or when decision-making starts to rely too heavily on gut instinct instead of data. She highlights clear signs that a company is ready for financial leadership: outgrowing basic tools like QuickBooks, feeling uncertain about profitability, or needing clarity around cash flow and personnel costs. A fractional CFO doesn’t just manage numbers—they partner with founders to bring order, foresight, and peace of mind. Laresa shares how implementing more detailed financial reporting and proactive cash flow forecasting helps business owners understand where their money is going, where it should go next, and how to allocate it efficiently. This support allows leaders to step back from financial stress and focus on strategy, growth, and innovation instead. For founders still below seven figures, Laresa recommends starting early by setting up robust accounting systems and forecasting tools. Preparation ensures a fractional CFO can deliver maximum value once engaged. By building these systems in advance, founders avoid reactive decisions and gain clarity on how each financial move impacts long-term scalability. About Laresa McIntyre Laresa McIntyre is the Founder and Fractional CFO at Rockbridge CFO, where she helps businesses gain financial clarity, improve profitability, and scale strategically. With years of experience supporting founders and executive teams, she specializes in transforming financial chaos into actionable growth strategies. About Rockbridge CFO Rockbridge CFO provides strategic financial leadership for growing companies through fractional CFO services. The firm focuses on forecasting, profitability analysis, and cash flow management—empowering business owners to make confident, data-driven decisions without the expense of a full-time CFO. Links Mentioned in this Episode Rockbridge CFOLaresa McIntyre LinkedIn Profile Key Episode Highlights Conclusion Hiring a fractional CFO isn’t just about managing your finances—it’s about reclaiming your time, focus, and confidence as a leader. As Laresa McIntyre explains, the right time to bring in a CFO is when you’re ready to grow with clarity and strategy instead of stress and guesswork. Whether your business is at $500K or $5M, proactive financial leadership can set the foundation for sustainable, scalable success. 🎧 More from UpMyInfluence: 🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of...

Navigating the 2025 SMB Landscape: Proactive Tax Strategies and Expert Insights from Adam Williams Small and medium-sized business owners are facing unprecedented challenges in 2025, from rapid legal changes to AI-driven disruption. In a recent episode, Josh Elledge sat down with Adam Williams, author and Co-founder of Pennywise Tax Strategies, to explore actionable strategies for SMB founders navigating complex tax, legal, and operational environments. Adam shared insights on proactive tax planning, leveraging expert advisors, and adapting to technological changes to help businesses thrive in an increasingly dynamic landscape. The Power of Proactive Tax Planning Adam emphasizes that reactive tax preparation is no longer sufficient for SMBs looking to maximize profits and future-proof their businesses. Forward-thinking strategies like auditing profit and loss statements, employing family members, leveraging the Augusta Rule, choosing the right business entity, and utilizing cost segregation can save businesses significant money while maintaining compliance. He also highlights the importance of ongoing education and expert advisors, ensuring owners can confidently navigate new laws, AI integration, and changing economic conditions. Proactive planning goes beyond minimizing taxes—it’s about optimizing operations and leveraging every available advantage. SMB owners can use these strategies to automate processes, structure their teams effectively, and ensure every deduction, credit, or exemption is captured. Adam’s guidance demonstrates how combining thoughtful planning with expert support allows businesses to remain agile, profitable, and competitive in 2025 and beyond. Entrepreneurs who implement these strategies not only reduce risk but also position their businesses for sustainable growth. From cost-saving opportunities to AI-driven efficiency improvements, the insights Adam shared provide a clear roadmap for SMB founders seeking long-term success. By taking a proactive approach, business owners can reclaim control over their finances, optimize operations, and confidently scale their enterprises. About Adam Williams Adam Williams is the Co-founder of Pennywise Tax Strategies and a seasoned author focused on actionable tax and business advice for small and medium-sized enterprises. With deep expertise in tax planning, business law, and strategic consulting, Adam empowers SMB owners to make informed decisions that maximize profits and minimize risk. About Pennywise Tax Strategies Pennywise Tax Strategies helps small and medium businesses implement proactive tax planning, optimize deductions, and leverage financial strategies to grow efficiently. Their team specializes in forward-looking solutions that combine expert knowledge with practical, actionable tactics for entrepreneurs navigating a rapidly evolving business environment. Links Mentioned in this Episode Pennywise Tax StrategiesAdam Williams LinkedIn Key Episode Highlights Conclusion The 2025 SMB environment demands proactive planning, strategic partnerships, and a keen understanding of tax and operational opportunities. Adam Williams’ insights provide a roadmap for entrepreneurs seeking to thrive amid uncertainty by optimizing finances, leveraging expert guidance, and positioning...

Growth Through Acquisition: Lessons from Navy Veteran and Entrepreneur Gary MacDermid Entrepreneurship often requires both discipline and strategic vision, and few embody that combination like Gary MacDermid—a Navy veteran turned successful business acquirer, investor, and author. In a recent episode of The Thoughtful Entrepreneur, host Josh Elledge sat down with Gary to discuss his journey from military service to civilian business leadership, offering actionable strategies for veterans and entrepreneurs alike. This post distills key insights from the conversation, focusing on growth through acquisition, creative financing, and the importance of intentional goal-setting. Accelerating Growth Through Acquisition and Strategic Goal-Setting Gary emphasizes that acquiring businesses—rather than relying solely on organic growth—can rapidly scale revenue, talent, and operational capacity. By identifying complementary businesses and overlaying high-value services, entrepreneurs can unlock immediate opportunities and enhance client value. Creative financing options, such as seller financing, SBA loans, and private investors, make acquisitions accessible even without deep upfront capital, allowing business owners to pursue strategic growth without overextending resources. Veterans, in particular, benefit from leveraging military discipline and intentional goal-setting, which Gary details in his book Set Your Own Goals or Someone Else Will. He recommends defining clear milestones, breaking down actionable steps, and seeking mentorship or peer accountability to navigate complex business decisions effectively. Beyond acquisition strategies, Gary stresses the importance of cultural integration and communication to ensure smooth transitions for both clients and staff, ensuring that growth is sustainable rather than just rapid. For all entrepreneurs, Gary underscores the value of overlaying high-ticket services on acquired businesses, continuously learning from new markets, and integrating processes that drive efficiency. Whether transitioning from military service or expanding an existing business, the principles of acquisition, strategic financing, and clear goal-setting serve as powerful levers to accelerate success. About Gary MacDermid Gary MacDermid is a Navy veteran, investor, business acquirer, and author of Set Your Own Goals or Someone Else Will. He leverages his military experience and entrepreneurial expertise to help veterans, career changers, and business leaders strategically grow and scale their businesses. About Gary’s Company Gary specializes in growth through acquisition, creative financing, and advisory services that empower entrepreneurs to expand efficiently while maintaining operational and cultural integrity. His methods help businesses unlock hidden value and pursue strategic opportunities with confidence. Links Mentioned in This Episode https://garymacdermid.comSet Your Own Goals or Someone Else Will Key Episode Highlights Conclusion Gary MacDermid’s insights demonstrate that disciplined strategy, smart acquisition, and intentional goal-setting are essential tools for accelerating growth. By leveraging military experience, creative financing, and high-value service overlays, entrepreneurs and veterans alike can unlock...