The Thoughtful Entrepreneur

Josh Elledge · UpMyInfluence.com & PodVerified.com

The Thoughtful Entrepreneur features candid, commercial-free conversations with the founders, CEOs, and B2B leaders building the companies and ideas shaping their industries. Each episode runs 15-25 minutes, built for busy professionals who want substance without the filler. Guests include agency owners, consultants, coaches, and executives with real stories, hard-won lessons, and specific insight for business leaders focused on growth. Host Josh Elledge has conducted 3,000+ interviews, helped launch 300+ podcasts, and has been directly involved in generating $40M+ in client results through relationship-driven media. He knows what makes a guest worth featuring and what makes an appearance actually worth the guest's time. Want to be featured? Guests are selected through PodVerified, the platform built by podcast hosts to restore trust and quality to podcast guesting. If you're a serious B2B expert with a clear message and a story worth sharing, apply here: 👉 https://PodVerified.com/podcast

  1. 6H AGO

    2389 - Putting the Human Side Back into Management with Manager Method’s Ashley Herd

    The Manager Method: Practical, Human-Centered Leadership for a Changing WorkplaceIn a world where technology and AI are transforming the workplace at breakneck speed, the fundamentals of great leadership remain rooted in human connection and intentional action. In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Ashley Herd, the Founder and CEO of Manager Method, to explore the core of effective management. Drawing on her diverse background in legal and HR leadership at organizations like McKinsey, Ashley shares how to move beyond abstract theory into actionable behaviors. This conversation provides a roadmap for executives and founders to drive performance and talent retention through a refreshingly human-centered lens. Scaling Leadership Excellence: The "Pause, Consider, Act" FrameworkHigh-performing leaders often struggle with the "reactive trap"—the tendency to respond impulsively to the endless stream of workplace demands. Ashley Herd argues that the most effective tool in a leader’s arsenal is the intentional pause. Most management mistakes are born from quick answers that leaders later regret, especially in high-pressure environments. By taking a moment to step back before making a decision, a leader creates the space necessary to avoid bias and emotional knee-jerk reactions. This practice is the foundation of the "Manager Method," transforming leadership from a series of frantic responses into a deliberate strategy that builds trust and long-term credibility with the team. Effective leadership development must also be scalable and sustainable, rather than a one-time event that ends once a workshop concludes. Ashley emphasizes a "three-legged stool" approach to management training, which combines on-demand video learning, practical resource guides, and live cohort sessions. This model moves away from the traditional, expensive external trainer model and focuses on building internal muscle memory. By integrating bite-sized, practical lessons into a manager’s monthly routine, organizations can ensure that leadership skills are being practiced and refined in real-time. This ensures that the "human touch" remains a core differentiator, even as automation and AI begin to handle more administrative heavy lifting. Transparency remains the ultimate currency in a modern workplace defined by rapid change. Many leaders wait until they have a "perfect" plan before communicating with their teams, but this silence often breeds anxiety and speculation. Ashley advocates for a "work-in-progress" communication style where leaders acknowledge what they know, admit what they don’t, and involve the team in brainstorming solutions. Whether navigating a personnel change or integrating new AI tools, involving the team early reduces fear and empowers employees to become stakeholders in the outcome. When people feel seen and valued as human beings rather than mere resources, they are far more likely to remain engaged and productive during periods of transition. About Ashley HerdAshley Herd is the Founder and CEO of Manager Method and a highly sought-after leadership consultant. With extensive experience in HR and employment law, she has led people operations for global firms and has become a leading voice in modern management. She is the author of The Manager Method: A Practical Framework to Lead, Support, and Get Results, and is dedicated to making high-level leadership training accessible to managers at every level. About Manager MethodManager Method is a leadership development firm that provides practical, scalable training for organizations seeking to improve management performance. The company offers a mix of digital learning, resource toolkits, and facilitated sessions designed to build foundational skills in communication, feedback, and empathy. Manager Method focuses on human-centered frameworks that drive results by empowering leaders to lead with clarity and intention. Links Mentioned in This EpisodeManager Method Official Website: www.managermethod.comAshley Herd on LinkedIn: https://www.linkedin.com/in/ashleyherd/ Key Episode HighlightsThe "Pause, Consider, Act" Framework: A three-step method for reducing impulsivity and making more empathetic, informed decisions.Transparent Communication: Why admitting "I don't have all the answers yet" is more effective than silence during periods of organizational change.The Three-Legged Stool of Training: A scalable model for management development that integrates video, resources, and live peer discussion.AI and the Human Differentiator: Why the rise of automation makes human-centered management skills like empathy more valuable than ever.Leadership as a Practice: Learning from music—why consistency and foundational "basics" are more important than being a management virtuoso. ConclusionThe conversation with Ashley Herd highlights that great leadership is built on small, consistent actions rooted in empathy and transparency. By adopting the "Pause, Consider, Act" framework, leaders can navigate workplace complexity with confidence while building a culture that prioritizes human connection. More from The Thoughtful Entrepreneur🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. 👉 Schedule your guest spot here » 🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. 👉 See how here » 📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who land dream guests weekly. 👉 See the system here » 🚨 What’s Your PodVerified Score? Find out how you rank as a podcast guest — and get matched with hosts who actually want you. 👉 View the platform » 📬 Subscribe to The Thoughtful Entrepreneur New episodes daily to fuel your impact, visibility, and influence. Thanks for listening — now go build something extraordinary! To discover more strategies for scaling your impact and growing your authority, explore the resources available at UpMyInfluence.com. If you are a founder or executive with a story to share, we’d love to hear from you—click here to apply as a guest on The Thoughtful Entrepreneur Podcast!

    23 min
  2. 1D AGO

    2388 - The Playbook for a Winning Team Culture with BH Consultancy’s Bobby Humes

    Mastering the Human Side of Leadership: Lessons in Agility with Bobby HumesIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Bobby Humes, Lead Consultant & CEO of BH Consultancy, to discuss the shifting paradigms of modern management. Bobby, widely known as "Coach Bobby," brings a unique perspective to the table, blending his high-level executive experience with lessons learned from coaching youth basketball. Their conversation explores the vital transition from technical expertise to people-centric leadership, the necessity of documenting institutional knowledge in a post-"Great Resignation" world, and how thoughtful leaders can leverage AI to enhance—rather than replace—human potential. This episode serves as a strategic roadmap for founders and executives who want to build resilient cultures that thrive on innovation and intentionality. Bridging the Gap: From Technical Expert to Thoughtful LeaderThe transition from a high-performing individual contributor to an effective people leader is one of the most difficult hurdles in the professional journey. Bobby Humes explains that while technical skills may earn a seat at the table, emotional intelligence and strategic delegation are what sustain a leader’s impact. Many founders fall into the "dragon" trap—possessing so much passion and expertise that they inadvertently micromanage their team, robbing them of the opportunity to grow. Thoughtful leadership requires a shift in mindset where the goal is no longer to be the best player on the court, but to be the coach who harnesses the diverse energy of the team and directs it toward a cohesive, long-term vision. Building organizational resilience in 2026 requires more than just reactive hiring; it demands proactive succession planning and the meticulous documentation of critical knowledge. Bobby observes that many organizations were left vulnerable during recent market shifts because they lacked "desk manuals" or structured onboarding processes. When a key team member exits, the loss of institutional knowledge can be catastrophic if it hasn't been documented. By treating onboarding as a strategic priority and creating living documents of core processes, leaders ensure that their teams remain agile and capable of maintaining momentum even during periods of transition or sudden talent loss. Innovation within a company is often a byproduct of what Bobby calls a "culture of play." In this environment, experimentation is encouraged, and "failing forward" is seen as an essential step toward discovery. This spirit of play is where true innovation happens—during whiteboard sessions and open-ended brainstorming where team members feel safe to voice unconventional ideas. Integrating technology, specifically AI, into this culture can serve as a massive force multiplier for human wellness and efficiency. By setting clear guidelines—such as using AI to draft complex communications or automate repetitive administrative tasks—leaders can free up their people to focus on the high-value, creative work that truly moves the needle for the business. About Bobby HumesBobby Humes is the Lead Consultant & CEO of BH Consultancy and a highly sought-after executive coach. Known for his "Coach Bobby" persona, he specializes in helping technical experts transition into world-class people leaders. With a focus on emotional intelligence and strategic agility, Bobby works with organizations to develop leadership pipelines, improve talent retention, and foster innovative work cultures. About BH ConsultancyBH Consultancy is a premier leadership and management consultancy based in Seattle. The firm provides a holistic approach to organizational health, offering services that range from strategic planning and whiteboard innovation sessions to executive coaching and wellness integration. BH Consultancy is dedicated to helping businesses navigate the complexities of the modern workforce through thoughtful, intentional leadership. Links Mentioned in This EpisodeBH Consultancy Official WebsiteBobby Humes on LinkedIn Key Episode HighlightsThe "Dragon" Metaphor: Why leaders must resist the urge to take over and instead empower their team to bring their own creativity to the table.Emotional Intelligence in Scaling: The critical need for founders to develop soft skills as they transition from "doing" to "leading."Institutional Knowledge Audits: The importance of desk manuals and process documentation to survive sudden talent transitions.AI as a Wellness Tool: Leveraging technology to reduce administrative friction and prevent burnout among high-performing teams.The Culture of Play: How fostering a safe environment for experimentation directly leads to business innovation. ConclusionThe conversation with Bobby Humes highlights that the most successful organizations of the future will be those that prioritize human connection and intentionality. By evolving from a technical expert into a thoughtful leader, you can build a team that is not only productive but truly resilient in the face of change. More from The Thoughtful Entrepreneur🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. 👉 Schedule your guest spot here » 🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. 👉 See how here » 📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who land dream guests weekly. 👉 See the system here » 🚨 What’s Your PodVerified Score? Find out how you rank as a podcast guest — and get matched with hosts who actually want you. 👉 View the platform » 📬 Subscribe to The Thoughtful Entrepreneur New episodes daily to fuel your impact, visibility, and influence. Thanks for listening — now go build something extraordinary! To discover more strategies for scaling your impact and growing your authority, explore the resources available at UpMyInfluence.com. If you are a founder or executive with a story to share, we’d love to hear from you—click here to apply as a guest on The Thoughtful Entrepreneur Podcast!

    17 min
  3. 2D AGO

    2387 - Why the Toughest Challenges Can Lead to Purpose-Driven Success with Patrick Mork

    Building Purpose-Driven Companies: Leadership Wisdom with Patrick MorkIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Patrick Mork, a renowned leadership speaker, executive advisor, and author of Step Back and Leap: Nine Keys to Unlock Your Life and Make Change Happen. Drawing from his high-octane background as a tech founder and a three-time Chief Marketing Officer, Patrick shares how the modern leadership landscape requires more than just technical acumen—it demands a foundation of purpose. This conversation explores the psychological and operational hurdles of the startup journey, providing a strategic roadmap for founders who want to build companies that are as resilient as they are impactful. Mastering the "Soft Tissue" of High-Performance LeadershipTransitioning from a technical expert to a true leader often reveals a significant gap in what Patrick calls the "operating system" of a company: its culture and interpersonal dynamics. For many founders, the most grueling part of the journey isn't the coding or the fundraising, but the inevitable friction that arises between co-founders and senior teams. Patrick emphasizes that conflict is not a sign of failure, but a necessary component of growth—provided it is managed with intention. When leaders avoid difficult conversations, they allow small misalignments to calcify into existential threats. By implementing structured feedback loops and fostering a shared language for disagreement, founders can transform potential volatility into a catalyst for innovation and deep-seated trust. The ability to delegate is another critical threshold that separates stagnant startups from scalable enterprises. Patrick recounts the cautionary tale of successful founders who remain bogged down in administrative minutiae, such as booking their own travel, long after they should have focused on high-level strategy. This failure to let go often stems from a lack of "purpose-driven" hiring; when a team is not aligned with the core mission, trust remains elusive. Effective delegation requires a leader to communicate the "why" behind every task, empowering the team to take ownership of the outcomes rather than just following a checklist. This shift moves the founder from a micromanager to a visionary, freeing up the mental bandwidth required to navigate a rapidly changing, AI-driven market. Perhaps the most vital insight Patrick offers is the direct link between purpose and the prevention of burnout. In a world where the startup life is often likened to "chewing glass," resilience is fueled by a sense of contribution and service. Burnout rarely occurs because of hard work alone; it happens when that work is fundamentally misaligned with an individual’s core values. Using frameworks like the Japanese Ikigai method, leaders can audit their own lives and organizations to ensure their professional pursuits honor their whole selves. When a company’s mission is clearly articulated and lived through everyday behaviors, it becomes a magnet for top-tier talent and a compass that guides the organization through the inevitable emotional rollercoasters of entrepreneurship. About Patrick MorkPatrick Mork is an Executive Advisor to CEOs and Senior Leadership Teams, a leadership speaker, and the host of the Mork Unfiltered podcast. With a career spanning roles as a tech founder and three-time CMO, he specializes in helping leaders navigate change, find their purpose, and build high-performing cultures. He is the author of Step Back and Leap, a book designed to help professionals unlock their potential and lead more meaningful lives. About Patrick Mork LLCPatrick Mork LLC provides executive coaching, leadership workshops, and advisory services tailored for founders and senior executives in the tech sector and beyond. The firm focuses on the intersection of human-centered leadership and business performance, helping organizations define their purpose and develop the "soft skills" necessary for sustainable scaling and resilience. Links Mentioned in This EpisodePatrick Mork LLC Website: www.patrickmork.comPatrick Mork on LinkedIn: linkedin.com/in/patrickmorkofficial Key Episode HighlightsPurpose as a Competitive Advantage: Why purpose-driven companies attract higher-quality talent and maintain greater resilience during market downturns.The Danger of Avoiding Conflict: How unresolved co-founder friction can quietly erode a company’s foundation and how to address it proactively.The Ikigai Method for Leaders: Using this Japanese framework to align professional goals with personal values to prevent burnout.The "Chewing Glass" Metaphor: Navigating the intense emotional highs and lows of the startup journey without losing perspective.Scaling Through Delegation: Moving beyond micromanagement by building a trustworthy team aligned with the company’s mission. ConclusionThe conversation with Patrick Mork serves as a powerful reminder that the most durable companies are built from the inside out. By prioritizing self-reflection, mastering feedback, and anchoring every decision in a clear sense of purpose, founders can build a legacy that transcends mere financial success. More from The Thoughtful Entrepreneur🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. 👉 Schedule your guest spot here » 🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. 👉 See how here » 📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who land dream guests weekly. 👉 See the system here » 🚨 What’s Your PodVerified Score? Find out how you rank as a podcast guest — and get matched with hosts who actually want you. 👉 View the platform » 📬 Subscribe to The Thoughtful Entrepreneur New episodes daily to fuel your impact, visibility, and influence. Thanks for listening — now go build something extraordinary! To discover more strategies for scaling your impact and growing your authority, explore the resources available at UpMyInfluence.com. If you are a founder or executive with a story to share, we’d love to hear from you—click here to apply as a guest on The Thoughtful Entrepreneur Podcast!

    21 min
  4. 3D AGO

    2386 - Stirring Corporate Talent into Nonprofit Board Service with Cause Strategy Partners’ Whitley Richards

    Empowering Professionals and Corporate Culture Through Nonprofit Board Service: Insights from Whitley RichardsIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Whitley Richards, the CEO of Cause Strategy Partners, to explore the high-impact intersection of corporate talent and social good. Their conversation highlights how nonprofit board service is no longer just an act of charity; it is a strategic vehicle for leadership development and corporate social responsibility (CSR). Whitley explains how her organization bridges the gap between major corporations and the nonprofit sector, ensuring that professionals from companies like Google and JPMorgan Chase are not only placed on boards but are equipped with the governance training necessary to drive real systemic change. The Strategic Triple Win: Professionals, Companies, and CommunitiesFacilitating nonprofit board service creates a powerful synergy that addresses the most pressing pain points for modern business leaders: employee disengagement and the "skills gap." When a company encourages its rising talent to serve on a board, it is essentially outsourcing high-level leadership training to the real world. In the boardroom, professionals must navigate complex challenges such as financial oversight, strategic planning, and consensus-building among diverse stakeholders—all of which are "power skills" that translate directly back to their corporate roles. This hands-on experience often proves more effective than traditional classroom-style leadership retreats, as it places the individual in a position of high-stakes accountability for a cause they genuinely care about. From a corporate perspective, supporting board service is a robust retention tool that satisfies the modern worker’s hunger for purpose. Employees who feel their personal values align with their professional environment are significantly more likely to remain loyal and engaged. Furthermore, these placements act as a force multiplier for a company’s corporate citizenship. Instead of merely writing a check, a corporation is lending its intellectual capital to the community, building deeper, more authentic ties with local organizations. This proactive approach to corporate citizenship bolsters brand reputation and establishes the company as a pillar of the community, which is increasingly vital in a consumer landscape that rewards social transparency and impact. For the nonprofits involved, the influx of corporate expertise provides a level of professionalization and strategic rigor that can be difficult to acquire otherwise. Cause Strategy Partners uses a technology-driven approach to ensure these matches are based on more than just proximity; they are based on a deep alignment of skills and passion. This ensures that the professional isn't just a figurehead but a high-value contributor who can help the nonprofit navigate resource allocation and organizational direction. By shifting the narrative from "volunteering" to "strategic board service," Whitley and her team are redefining how we think about social impact, creating a sustainable model where every participant walks away with measurable growth and a renewed sense of mission. About Whitley RichardsWhitley Richards is the CEO of Cause Strategy Partners and a recognized leader in the social impact space. With an MPA from NYU Wagner, she has dedicated her career to the belief that the private sector holds the keys to solving many of the world's most difficult social challenges. She oversees the strategic direction of the firm, focusing on expanding the reach of their board placement and governance training programs to empower the next generation of social-impact leaders. About Cause Strategy PartnersCause Strategy Partners is a social enterprise that helps individuals and corporations achieve their greatest social impact. Through their flagship BoardLead program and a suite of governance resources, they match talented professionals with nonprofit board opportunities. By providing rigorous training and technology-powered matching, the firm ensures that nonprofit boards are diverse, skilled, and prepared to lead their organizations toward long-term success. Links Mentioned in This EpisodeCause Strategy Partners Official WebsiteWhitley Richards on LinkedIn Key Episode HighlightsThe "Triple Win" Framework: How board service simultaneously benefits the professional, the corporation, and the nonprofit partner.Governance as Leadership Training: Why the boardroom is the ultimate environment for developing emotional intelligence and strategic thinking.Bridging the Purpose Gap: Strategies for companies to retain top talent by facilitating meaningful social engagement.Technology in Placements: The role of data-driven matching in ensuring that board service is high-impact rather than just high-intent.The "My Cause Finder" Tool: A practical resource for individuals to identify where their skills meet the world’s needs. ConclusionThe conversation with Whitley Richards underscores that nonprofit board service is a transformative opportunity for professional and organizational growth. By aligning personal passions with strategic service, individuals can develop critical leadership skills while corporations strengthen their culture and community impact. More from The Thoughtful Entrepreneur🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. 👉 Schedule your guest spot here » 🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. 👉 See how here » 📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who land dream guests weekly. 👉 See the system here » 🚨 What’s Your PodVerified Score? Find out how you rank as a podcast guest — and get matched with hosts who actually want you. 👉 View the platform » 📬 Subscribe to The Thoughtful Entrepreneur New episodes daily to fuel your impact, visibility, and influence. Thanks for listening — now go build something extraordinary! To discover more strategies for scaling your impact and growing your authority, explore the resources available at UpMyInfluence.com. If you are a founder or executive with a story to share, we’d love to hear from you—click here to apply as a guest on The Thoughtful Entrepreneur Podcast!

    16 min
  5. 4D AGO

    2385 - Finding Balance Between Tactical Hobbies and Business Growth with CJAM's Behdad Jamshidi

    Navigating the Marketing Agency Maze: Strategic Matchmaking with Behdad JamshidiIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Behdad Jamshidi, the Founder & CEO of CJAM Marketing, to discuss the critical challenges business leaders face when trying to scale their marketing efforts. With over 160,000 agencies in the market, founders often find themselves trapped in a cycle of "agency hopping" that drains resources and kills momentum. Their conversation dives into the necessity of strategic matchmaking, the value of intentional leadership, and how to find the less than 5% of agencies that actually align with an entrepreneur's specific business goals. Protecting Your Growth: The Engineering Approach to Marketing PartnershipsFor many high-achieving founders, the struggle isn't a lack of marketing options, but a lack of clarity on which specific agency "flavor" fits their current objective. Behdad explains that the marketing industry is highly fragmented, with agencies specializing in everything from granular SEO to high-level brand storytelling. A common mistake is hiring an agency based on a polished sales pitch rather than a proven track record within a specific niche or budget bracket. By acting as a fractional CMO and partner matcher, strategic consultants help business owners bypass the expensive trial-and-error phase, ensuring that the agency selected has the exact infrastructure required to scale that specific business model. Effective marketing leadership requires an objective view of the "entire board," moving beyond tactical execution to focus on foundational strategy. Business owners often jump into paid ads or social media campaigns before their internal systems—like lead follow-up and CRM management—are ready to handle the influx. This creates a "leaky bucket" scenario where marketing spend is effectively wasted. Strategic matchmaking involves auditing these internal processes first, then pairing the business with a partner who understands the nuance of their industry and the specific stage of the entrepreneurial journey they are navigating. This alignment ensures that marketing becomes a predictable engine for growth rather than a series of disconnected experiments. Ultimately, the goal of a strategic partnership is to build long-term value and trust, which is often missing in the transactional world of digital marketing. The matchmaking process relies on deep vetting and a massive network of pre-screened providers, allowing founders to access high-level talent without the risk of a "bad hire." As companies scale, their marketing needs evolve, and having a partner who can facilitate those transitions ensures that the brand remains consistent and the momentum continues. By prioritizing the relationship and the strategic fit over the latest marketing fad, entrepreneurs can reclaim their time and focus on leading their organizations with confidence. About Behdad JamshidiBehdad Jamshidi is the Founder & CEO of CJAM Marketing, where he serves as a strategic marketing consultant and agency matchmaker. With a background in engineering, Behdad brings a technical, process-driven perspective to the creative world of advertising. He specializes in identifying the perfect marketing partners for growing businesses, helping them build scalable, high-performance marketing ecosystems while protecting them from poor investments. About CJAM MarketingCJAM Marketing is a strategic consultancy that helps businesses find and manage the right marketing partners. By leveraging a vast network of vetted agencies and providers, CJAM Marketing removes the guesswork from the hiring process. The firm provides fractional CMO services, auditing internal processes and aligning business goals with the specific technical capabilities of marketing specialists to ensure sustainable, long-term growth. Links Mentioned in This EpisodeCJAM Marketing Official WebsiteBehdad Jamshidi on LinkedIn Key Episode HighlightsThe Agency Hopping Trap: Why businesses fail when they hire based on sales pitches rather than strategic, technical fit.The Kaizen Philosophy: Applying continuous, incremental improvement to both personal leadership and business operations.Tactical Hobbies for Leaders: How hands-on activities like painting or music help founders reset their mental state for better decision-making.The 5% Rule: Navigating the crowded market to find the small fraction of agencies that are actually capable of delivering ROI.Radical Transparency: How standardized referral fees and engagement models ensure unbiased marketing recommendations. ConclusionThis conversation with Behdad Jamshidi underscores that marketing success is less about the "what" and more about the "who." By finding the right strategic partners who align with your mission and stage of growth, you can transform marketing from a source of frustration into your most powerful tool for impact. More from The Thoughtful Entrepreneur🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. 👉 Schedule your guest spot here » 🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. 👉 See how here » 📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who land dream guests weekly. 👉 See the system here » 🚨 What’s Your PodVerified Score? Find out how you rank as a podcast guest — and get matched with hosts who actually want you. 👉 View the platform » 📬 Subscribe to The Thoughtful Entrepreneur New episodes daily to fuel your impact, visibility, and influence. Thanks for listening — now go build something extraordinary! To discover more strategies for scaling your impact and growing your authority, explore the resources available at UpMyInfluence.com. If you are a founder or executive with a story to share, we’d love to hear from you—click here to apply as a guest on The Thoughtful Entrepreneur Podcast!

    26 min
  6. 5D AGO

    2384 - Empowering Entrepreneurs Everywhere Through Democratized Business Education with BOS-UP's Scott Abbott

    Mastering Business Scalability: Scott Abbott on Fusing AI, Systems, and Human GrowthIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Scott Abbott, the serial entrepreneur, investor, and Founder & CEO of BOS-UP. The conversation explored the critical intersection of modern technology and timeless business principles, focusing on how Scott’s "Boss Up" framework helps startups and mid-market companies scale effectively. By integrating AI-driven insights with high-level coaching and human-centered development, Scott provides a roadmap for leaders who want to move beyond mere "hustle" and toward a structured, engineering-minded approach to growth. This episode is a masterclass in leveraging the latest digital tools without losing the "soft tissue" of emotional intelligence and personal reflection. The Boss Up Methodology: Balancing Business Mechanics with Human Soft TissueScaling a business requires a dual focus on rigorous systems and the human factors that drive them. Scott Abbott describes this balance through the lens of "mechanics"—the essential business competencies and disciplines—and "soft tissue," which encompasses conflict resolution, anxiety management, and boundary setting. For an organization to truly thrive, it must implement a blueprint that democratizes high-level strategies once reserved only for the Fortune 500. By adopting an engineering mindset, founders can build a "Boss Up Blue" infrastructure that identifies operational gaps, while simultaneously using "Boss Up Moments" to foster the emotional resilience needed to navigate the inevitable stresses of entrepreneurship. A cornerstone of this methodology is the strategic integration of Artificial Intelligence as a partner in critical thinking rather than a replacement for it. Scott advocates for a three-dimensional learning model that fuses traditional reading and writing with AI-powered customization. Instead of using AI to generate shortcuts, leaders are encouraged to use tools like ChatGPT or NotebookLM to create personalized journaling prompts and organize complex insights. This technology-enhanced reflection allows for a deeper, more contextual understanding of business challenges, enabling a founder to show up to coaching sessions with a refined perspective that maximizes the value of human-to-human mentorship. Democratizing high-level business education is the ultimate mission behind the BOS-UP ecosystem. By offering open-source content and a social enterprise model where profits support under-resourced entrepreneurs, Scott is championing a form of humanitarian capitalism. This approach ensures that sophisticated tools for work-life integration and organizational scaling are accessible to all, regardless of their funding stage. When technology, coaching, and human-centered philosophies are fused correctly, the result is an interactive learning environment where founders can build not just successful companies, but purpose-driven lives that impact their communities and the global market. About Scott AbbottScott Abbott is a serial entrepreneur, investor, and the Founder & CEO of BOS-UP. With decades of experience building and scaling companies, he is a dedicated advocate for lifelong learning and the strategic use of technology in personal development. Scott is the author of Boss Up and the Boss Up Moments workbook, and he leads a global network of coaches focused on democratizing elite business strategies. About BOS-UPBOS-UP is a business coaching and systems firm designed to help small to mid-market companies scale with precision. The company offers a structured framework centered on nine core competencies, blending technical business engineering with human-centered growth strategies. BOS-UP operates as a social enterprise, providing accessible resources and coaching to empower entrepreneurs worldwide. Links Mentioned in This EpisodeScott Abbott Official WebsiteScott Abbott on LinkedIn Key Episode HighlightsThe "Boss Up" Framework: A deep dive into the nine core competencies required to scale a business from startup to mid-market success.AI as a Thinking Partner: How to use artificial intelligence to enhance critical thinking, generate reflective prompts, and prepare for high-level coaching.Mechanics vs. Soft Tissue: Balancing the technical systems of a business with the emotional intelligence and human factors that sustain a team.Democratizing Strategy: The social enterprise model that makes Fortune 2500-level business education accessible to under-resourced entrepreneurs.The 3D Learning Model: Integrating reading, writing, and technology to create a comprehensive and interactive ecosystem for lifelong growth. ConclusionScott Abbott’s philosophy serves as a reminder that the most successful businesses are built on a foundation of continuous learning and structural integrity. By embracing both the data-driven power of AI and the reflective depth of human coaching, leaders can navigate complexity with clarity and purpose. More from The Thoughtful Entrepreneur🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. 👉 Schedule your guest spot here » 🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. 👉 See how here » 📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who land dream guests weekly. 👉 See the system here » 🚨 What’s Your PodVerified Score? Find out how you rank as a podcast guest — and get matched with hosts who actually want you. 👉 View the platform » 📬 Subscribe to The Thoughtful Entrepreneur New episodes daily to fuel your impact, visibility, and influence. Thanks for listening — now go build something extraordinary! To discover more strategies for scaling your impact and growing your authority, explore the resources available at UpMyInfluence.com. If you are a founder or executive with a story to share, we’d love to hear from you—click here to apply as a guest on The Thoughtful Entrepreneur Podcast!

    18 min
  7. 6D AGO

    2383 - Exploring the Future of Digital Advertising Through AI, Strategy, and Human Creativity with Metadata’s Lisa Sharapata

    Revolutionizing Go-to-Market Strategy: AI-Driven Performance Marketing with Lisa SharapataIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Lisa Sharapata, the VP of AI & GTM Strategy at Metadata.io, to discuss the radical shift occurring in digital advertising. Metadata is a category-defining platform that utilizes AI agents to automate the technical execution of ad campaigns, effectively removing the manual "grunt work" that often bogs down marketing teams. Lisa shares how this transition allows marketers to shift their focus from bid adjustments and spreadsheet management to high-level media strategy and authentic creative development. Their conversation provides a strategic roadmap for B2B leaders looking to scale their demand generation without scaling their headcount. Beyond Manual Execution: The Power of Multivariate Testing at ScaleThe primary bottleneck in modern B2B advertising is the sheer complexity of testing—a human team simply cannot manually manage the permutations required to find the perfect campaign "winner" across fragmented channels. Lisa explains that Metadata solves this by running dozens or even hundreds of simultaneous experiments across platforms like LinkedIn, Facebook, Instagram, Reddit, and Bing. For example, a single campaign involving three different audiences, three unique offers, and three creatives across five channels results in 135 separate experiments; Metadata’s AI agents handle the deployment and optimization of these combinations in real-time, shifting budget to top performers instantly. This level of scale ensures that ad spend is always flowing toward the highest-converting opportunities, rather than sitting stagnant in underperforming assets. With AI handling the "doing" of marketing, the role of the modern marketer is being redefined toward strategy, entity optimization (EO), and deep audience understanding. Lisa notes that as search behavior shifts from traditional engines to AI-driven models like ChatGPT, brands must focus on "Entity Optimization"—ensuring their company is recognized as a reputable authority across the web so it is cited by these emerging AI tools. This shift requires marketers to be more present in community-led channels and multi-channel brand awareness efforts, letting AI handle the bid thresholds and technical safeguards while humans focus on the narrative and the brand’s positioning in the market. Ultimately, successful AI implementation requires a "human-in-the-loop" approach to maintain control over brand standards and financial parameters. Metadata addresses this by allowing users to set strict spend and bid limits, ensuring the AI operates within a safe "sandbox" of pre-approved strategic boundaries. As trust builds, organizations can gradually increase the autonomy of these agents, moving toward a future of vendor-agnostic optimization where the platform prioritizes what actually works for the client, rather than what benefits a specific social network's inventory. This unified data approach allows B2B firms to connect ad spend directly to pipeline and revenue, providing the transparent attribution necessary to justify marketing investment at the executive level. About Lisa SharapataLisa Sharapata is the VP of AI & GTM Strategy at Metadata.io and a seasoned marketing leader with a track record of driving growth for high-scale B2B organizations. Known for her expertise in Account-Based Marketing (ABM) and demand generation, she is a frequent speaker and thought leader on the intersection of creativity and data-driven strategy. Lisa is passionate about helping marketers reclaim their time through automation, often drawing parallels between the fluidity of her hobby in water ink painting and the organic flow of modern marketing data. About Metadata.ioMetadata.io is the leading operating system for B2B marketers, providing AI-driven automation for performance marketing and demand generation. The platform automates the repetitive, manual tasks involved in running and optimizing ad campaigns across LinkedIn, Facebook, Google, and more. By connecting ad spend to revenue data, Metadata helps organizations achieve higher ROI and provides a unified view of the go-to-market strategy. Links Mentioned in This EpisodeMetadata.io Official WebsiteLisa Sharapata on LinkedIn Key Episode HighlightsThe "Strategy Over Execution" Shift: Why AI is finally allowing marketers to abandon manual bid management and focus on creative storytelling.Multivariate Testing at Scale: How AI agents manage hundreds of campaign permutations across LinkedIn, Facebook, and Reddit to find the lowest cost per lead.From SEO to Entity Optimization (EO): Preparing your brand to be recognized and recommended by AI language models and emerging search tools.Spend Safeguards and Human Oversight: Maintaining control over automated campaigns through bid limits and "human-in-the-loop" approval workflows.End-to-End Attribution: Connecting top-of-funnel ad spend directly to bottom-of-funnel pipeline and revenue metrics. ConclusionThe conversation with Lisa Sharapata makes it clear that the future of marketing isn't about human vs. machine, but rather human and machine working in tandem. By automating the mechanical aspects of digital advertising, leaders can empower their teams to focus on the creativity and strategy that truly move the needle for the business. More from The Thoughtful Entrepreneur🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. 👉 Schedule your guest spot here » 🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. 👉 See how here » 📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who land dream guests weekly. 👉 See the system here » 🚨 What’s Your PodVerified Score? Find out how you rank as a podcast guest — and get matched with hosts who actually want you. 👉 View the platform » 📬 Subscribe to The Thoughtful Entrepreneur New episodes daily to fuel your impact, visibility, and influence. Thanks for listening — now go build something extraordinary! To discover more strategies for scaling your impact and growing your authority, explore the resources available at UpMyInfluence.com. If you are a founder or executive with a story to share, we’d love to hear from you—click here to apply as a guest on The Thoughtful Entrepreneur Podcast!

    19 min
  8. MAR 11

    2382 - Why Yelling at Referees Mirrors the Reality of Software Development Resilience with Apsis Labs' Wyatt Kirby

    Navigating Software Compliance: Strategic Custom Development with Wyatt KirbyIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Wyatt Kirby, Founder of Apsis Labs, to explore the high-stakes world of custom software in regulated sectors. As healthcare and financial industries face tightening security mandates, generic off-the-shelf tools often become more of a liability than an asset. Wyatt shares how his firm bridges the gap between the rapid efficiency of AI-driven development and the uncompromising necessity of human-led security oversight. This conversation offers a strategic roadmap for leaders who are outgrowing spreadsheets and seeking to build resilient, compliant digital infrastructures that can scale alongside their business goals. The Foundation of Digital Integrity: Custom Solutions and Regulatory RigorThe transition from "making do" with generic tools to investing in custom software is often triggered when operational complexity outpaces the capabilities of standard platforms. Wyatt explains that for businesses in the biotech or fintech spaces, software isn't just a utility; it is the primary safeguard for sensitive user data. While generic tools like Excel offer low barriers to entry, they lack the native HIPAA or PCI compliance frameworks required to protect against modern security threats. By building tailored applications, organizations can ensure that compliance is baked into the source code from day one, rather than trying to retroactively "patch" security onto a system that wasn't designed for it. Security best practices often fall by the wayside because they aren't "common practice" in the rush to market, a gap that can lead to catastrophic data breaches. Wyatt emphasizes that true resilience comes from a security-first mindset that informs every architectural decision, from database encryption to user authentication protocols. This level of rigor is especially critical as businesses begin to integrate AI into their development cycles. While AI can act as a high-speed "calculator" for developers—accelerating prototyping and reducing routine errors—it lacks the contextual awareness to verify the security implications of a complex system. Consequently, human expertise remains the indispensable final check to ensure that automated code meets the stringent legal requirements of regulated industries. Beyond the technical code, the success of a digital transformation project relies heavily on the resilience and leadership of the founders involved. Wyatt draws a fascinating parallel between software development and his experience as a high school football referee: both require the ability to make split-second decisions under scrutiny and move forward after an error. In a field as dynamic as custom development, mistakes are an opportunity for iteration rather than a reason for derailment. By combining the speed of AI with a culture of continuous improvement and expert human oversight, leaders can build software that doesn't just "fit" their business today, but empowers them to dominate their market tomorrow. About Wyatt KirbyWyatt Kirby is the Founder of Apsis Labs and a veteran in the custom software development space. With a background that spans biotech, finance, and professional sports officiating, Wyatt brings a unique perspective on precision, security, and resilience to his work. He is dedicated to helping businesses in regulated industries navigate technical complexity through tailored, high-performance software solutions. About Apsis LabsApsis Labs is a premier custom software development firm specializing in building secure, compliant web and mobile applications. Focused primarily on the healthcare and finance sectors, the firm leverages modern technology and AI-assisted workflows to deliver high-quality code that meets the strictest regulatory standards. Apsis Labs is committed to a "security-first" philosophy, ensuring that every solution is built to scale safely and efficiently. Links Mentioned in This EpisodeApsis Labs Official WebsiteWyatt Kirby on LinkedIn Key Episode HighlightsThe Scalability Wall: Why generic tools like Google Sheets eventually fail businesses in regulated industries and how custom software removes those bottlenecks.Security vs. Compliance: The distinction between "checking boxes" and embedding deep security best practices into your software architecture.AI as a Force Multiplier: How Apsis Labs uses AI to accelerate development while maintaining strict human-led verification for security and compliance.Resilience in Leadership: Lessons from the football field on owning mistakes and staying focused on long-term project goals.The ROI of Custom Apps: Why tailored workflows reduce manual labor and long-term error rates, far outweighing the initial investment. ConclusionThis conversation with Wyatt Kirby underscores that in the modern digital economy, security is the price of admission. By moving away from brittle, off-the-shelf tools and embracing custom development guided by expert human intuition, businesses can turn compliance from a hurdle into a competitive advantage. More from The Thoughtful Entrepreneur🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. 👉 Schedule your guest spot here » 🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. 👉 See how here » 📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who land dream guests weekly. 👉 See the system here » 🚨 What’s Your PodVerified Score? Find out how you rank as a podcast guest — and get matched with hosts who actually want you. 👉 View the platform » 📬 Subscribe to The Thoughtful Entrepreneur New episodes daily to fuel your impact, visibility, and influence. Thanks for listening — now go build something extraordinary! To discover more strategies for scaling your impact and growing your authority, explore the resources available at UpMyInfluence.com. If you are a founder or executive with a story to share, we’d love to hear from you—click here to apply as a guest on The Thoughtful Entrepreneur Podcast!

    16 min
4.9
out of 5
101 Ratings

About

The Thoughtful Entrepreneur features candid, commercial-free conversations with the founders, CEOs, and B2B leaders building the companies and ideas shaping their industries. Each episode runs 15-25 minutes, built for busy professionals who want substance without the filler. Guests include agency owners, consultants, coaches, and executives with real stories, hard-won lessons, and specific insight for business leaders focused on growth. Host Josh Elledge has conducted 3,000+ interviews, helped launch 300+ podcasts, and has been directly involved in generating $40M+ in client results through relationship-driven media. He knows what makes a guest worth featuring and what makes an appearance actually worth the guest's time. Want to be featured? Guests are selected through PodVerified, the platform built by podcast hosts to restore trust and quality to podcast guesting. If you're a serious B2B expert with a clear message and a story worth sharing, apply here: 👉 https://PodVerified.com/podcast