The Thoughtful Entrepreneur

Josh Elledge · UpMyInfluence.com & PodVerified.com
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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. 20H 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

  2. 1D 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

  3. 2D 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

  4. 3D 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

  5. 4D 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

  6. 5D AGO

    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

  7. 6D AGO

    2381 - Boosting Advertising Performance Through AI with Plurio’s Seva Ustinov

    Revolutionizing Digital Advertising: Strategic Insights into AI-Driven Campaign Management with Seva UstinovIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Seva Ustinov, the Founder and CEO of plurio, to discuss the seismic shift occurring within the digital advertising landscape. As managing ad spend across Google, Meta, and TikTok becomes increasingly fragmented and complex, Seva shares how autonomous AI agents are moving beyond simple data reporting to active execution. This conversation provides a masterclass for high-growth founders and marketing executives who are looking to bridge the gap between surface-level platform metrics and true bottom-line business outcomes. Navigating Complexity: The Rise of Autonomous Ad OptimizationThe primary bottleneck for modern marketing teams is the sheer volume of data generated across diverse sales funnels and advertising platforms. Seva explains that while traditional ad platforms optimize for immediate conversions—like a simple lead form submission—they often lack the visibility into deeper business goals, such as closed-loop sales or long-term subscriptions. This disconnect forces marketers into a grueling cycle of manual analysis and constant dashboard toggling. By implementing an autonomous agent that aggregates performance data across all channels, businesses can finally align their digital spend with their actual revenue cycles, ensuring that every dollar is attributed to a meaningful customer journey. Adopting AI in advertising is not about replacing human creativity, but rather acting as a force multiplier for strategic talent. An AI agent can handle the "grunt work" of identifying creative fatigue, reallocating budgets in real-time, and pausing underperforming segments across thousands of campaigns simultaneously. This level of granular management allows agencies and in-house teams to shift their focus away from repetitive tactical adjustments and toward high-level creative strategy and client relationship management. When the machine handles the math, the humans can focus on the mission, resulting in a more agile and responsive marketing engine that scales without a proportional increase in headcount. Ultimately, the goal of integrating autonomous agents like Plurio is to achieve a superior Return on Ad Spend (ROAS) through continuous, data-driven learning. Seva emphasizes the importance of the "human-in-the-loop" model, where the AI provides transparent, human-readable reasoning for every recommendation it makes. This transparency builds trust and allows marketers to maintain strategic oversight while the agent executes daily optimizations. For enterprises and growth-stage startups managing significant monthly spend, this approach transforms digital advertising from a cost center into a predictable, high-performance asset that evolves as quickly as the market does. About Seva Ustinov: Seva Ustinov is a tech visionary and the Founder and CEO of Plurio. With a background in building scalable marketing technologies, Seva is dedicated to helping companies navigate the complexities of digital acquisition through the power of autonomous AI agents. About plurio: plurio is an innovative AI platform that revolutionizes digital ad management by combining unified analytics with autonomous optimization. The platform connects to major ad accounts to analyze performance, identify inefficiencies, and execute campaign adjustments, helping businesses maximize their ROI with minimal manual intervention. Links Mentioned in This Episode: plurio Official WebsiteSeva Ustinov on LinkedIn Key Episode HighlightsThe Full-Funnel Gap: Why standard ad platforms often fail to optimize for long-term business goals and how AI bridges that data void.Autonomous Execution: The shift from passive dashboards to active agents that can pause, scale, and reallocate spend in real-time.Force Multiplying Creativity: How AI frees up marketing agencies to focus on high-level strategy rather than manual spreadsheet analysis.Combating Creative Fatigue: Using AI to proactively spot when ad assets lose effectiveness and rotating them before ROI drops.Transparency and Trust: The "Human-in-the-Loop" model that provides clear reasoning for every AI-driven campaign adjustment. ConclusionThe conversation with Seva Ustinov makes it clear that the future of digital advertising lies in the synergy between human strategy and autonomous execution. By leveraging AI to handle the complexity of multi-channel optimization, leaders can ensure their growth is driven by data rather than guesswork. 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

  8. MAR 9

    2380 - Smart Tax Strategies for Business Owners Using Trusts with Sally Gimon

    Unlocking Advanced Tax Savings: How Strategic Trusts Empower Entrepreneurs with Sally GimonIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Sally Gimon, a dedicated Investor and tax strategist at The Trust is You, to dismantle the common frustrations business owners face during tax season. Despite having experienced CPAs, many entrepreneurs find themselves blindsided by massive tax bills—a pain point Sally knows intimately from her own early days in real estate. Their conversation dives into the specialized world of non-grantor irrevocable spendthrift trusts, a legal framework used by America’s wealthiest dynasties to protect assets and defer taxes. This episode serves as a vital resource for high-achieving founders looking to move beyond basic deductions and into the elite level of wealth preservation. Beyond Compliance: Why Your CPA Might Be Missing Millions in SavingsMost business owners rely solely on their CPAs for tax advice, but there is a fundamental gap between tax compliance and specialized trust law. CPAs are expertly trained in the tax code, yet only a tiny fraction of professionals are versed in the nuances of contract law and the specific IRS codes that govern complex trusts. This often leads to a "compliance trap" where entrepreneurs follow the rules perfectly but still overpay because they aren't utilizing the same legal structures as the Rockefellers or the Kennedys. By bridging this gap, business owners can move from a reactive state of paying what they're told to a proactive state of legally shielding their hard-earned capital. The core of Sally’s strategy revolves around Tax Code 643(b), which allows certain types of trusts to defer capital gains and passive income legally. While the IRS may issue memos expressing disapproval of aggressive strategies, it is important to remember that only Congress has the power to change the tax code itself. For business owners with appreciating assets like real estate or intellectual property, these trusts offer a dual benefit: significant tax deferral and robust asset protection from creditors or lawsuits. Implementing these structures requires a shift in mindset, moving away from "income management" toward "asset orchestration" within a protected legal entity. Ultimately, the goal of advanced tax planning is to provide the founder with more liquidity to reinvest in their mission and legacy. Sally emphasizes that these tools are not "loopholes" but are established parts of the American legal system designed to encourage long-term investment and wealth stability. By leveraging educational resources and weekly masterminds, entrepreneurs can demystify these complex structures and determine if they are ready to implement a spendthrift or beneficial trust. Taking control of one's tax destiny is about more than just numbers; it’s about ensuring that the value created by the business remains within the family or the organization for generations to come. About Sally GimonSally Gimon is an experienced Investor and a leading advocate for tax education through her platform, The Trust is You. After facing a nearly six-figure tax bill early in her real estate career, she dedicated herself to uncovering the wealth-preservation secrets of the ultra-wealthy. Today, she helps business owners across 165 countries understand trust law to protect their assets and slash their tax burdens. About The Trust is YouThe Trust is You is an educational and strategic resource center focused on democratizing advanced tax-saving tools. The company provides video courses, weekly mastermind sessions, and specialized consulting on non-grantor irrevocable spendthrift trusts. Their mission is to empower entrepreneurs with the knowledge to legally minimize taxes and protect their legacy using proven trust frameworks. Links Mentioned in This EpisodeThe Trust is You Official WebsiteSally Gimon on LinkedIn Key Episode HighlightsThe CPA Limitation: Understanding why compliance-focused accounting often overlooks advanced wealth-preservation strategies.The Power of 643(b): How this specific tax code allows for the legal deferral of capital gains and passive income within a trust.Asset Protection: Why spendthrift trusts are the gold standard for shielding your business and personal assets from litigation.The "Rockefeller" Strategy: Lessons from America’s wealthiest families on using contract law to maintain multi-generational wealth.Democratizing Knowledge: How Sally’s free resources are making elite tax strategies accessible to small and medium-sized business owners. ConclusionThis conversation with Sally Gimon highlights that while the tax code is complex, it contains powerful provisions for those willing to look beyond standard accounting. By integrating trust law into your financial strategy, you can transform your relationship with the IRS and keep more of your wealth working for you. 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
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4.9
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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

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  • Creator
    Josh Elledge · UpMyInfluence.com & PodVerified.com
  • Years Active
    2018 - 2026
  • Episodes
    2K
  • Rating
    Clean
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    © https://upmyinfluence.com/privacy/
  • Show Website
    The Thoughtful Entrepreneur