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. 5H 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

  2. 1D 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

  3. 2D 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

  4. 3D AGO

    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

  5. 4D AGO

    2379 - Building Organizational Health Through Leadership and Team Culture with The Intention Collective’s Stacey Bailey

    Building Healthy Leadership Teams: Strategic Insights from Stacey Bailey of The Intention CollectiveIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Stacey Bailey, Senior Consultant at The Intention Collective, to explore the foundational elements of high-performing organizational culture. Stacey, an expert executive coach, shared how small to medium-sized businesses can move past the friction of "moving goalposts" to establish sustainable growth through clear strategic planning. Their conversation provides a masterclass for founders and executives on how to bridge the gap between visionary thinking and daily execution by fostering deep clarity and robust accountability rituals. Cultivating Operational Excellence Through Clarity and 90-Day RhythmsFor many entrepreneurs, the greatest barrier to scaling is not a lack of vision, but a lack of consistent operational rhythm. Stacey explains that clarity is the cornerstone of a healthy leadership team; without it, ambiguity breeds resentment and stalls momentum. When leaders fail to be explicit about expectations, they inadvertently create "unkind" environments where team members feel set up for failure. By adopting a "clear is kind" philosophy, organizations can eliminate the hidden friction that slows down decision-making and project delivery, allowing the team to move in unison toward a shared objective. A central framework discussed in the episode is the implementation of 90-day planning rhythms. Human attention spans and motivation levels naturally fluctuate, often waning after approximately three months. By breaking down annual visions into quarterly sprints, leaders can maintain high levels of engagement while remaining agile enough to pivot based on real-world data. This structure prevents the common visionary trap of constantly shifting priorities mid-stream, which often leads to team burnout. Instead, a defined 90-day finish line provides the team with a predictable cadence of "doing" and "reflecting," ensuring that progress is documented and celebrated before the next set of goals is established. Ultimately, building a resilient leadership team requires a commitment to "frustration tolerance" and a growth mindset. Stacey uses the metaphor of learning a new craft to describe the leadership journey—it requires patience, a willingness to make visible mistakes, and the discipline to stick with a process until it yields results. Accountability in this context isn't about micromanagement; it is about creating a "system and soul" toolkit where feedback loops and weekly check-ins become the lifeblood of the culture. When leaders model vulnerability and invite honest critique, they build the psychological safety necessary for their teams to innovate and take the calculated risks required for long-term market leadership. About Stacey Bailey: Stacey Bailey is a Senior Consultant and executive coach at The Intention Collective. With a background in helping diverse organizations navigate growth and change, she specializes in helping leadership teams align their internal culture with their external strategic goals. She is a proponent of using structured rhythms to drive both professional excellence and personal fulfillment. About The Intention Collective: The Intention Collective is a consultancy dedicated to helping small and medium-sized businesses build healthy, high-performing cultures. By combining strategic planning with leadership development, they provide organizations with the tools to create clarity, implement accountability, and drive sustainable growth. Their "System and Soul" approach ensures that both the tactical and human elements of a business are optimized for success. Links Mentioned in This Episode: The Intention Collective Official WebsiteStacey Bailey on LinkedIn Key Episode HighlightsFrustration Tolerance in Leadership: Why embracing the "messy middle" of learning new skills builds the resilience needed to lead through uncertainty.The Clarity Mandate: Implementing Brené Brown’s "Clear is Kind" principle to eliminate team resentment and improve execution.90-Day Sprint Rhythms: How to align organizational goals with natural human attention spans to maintain year-round momentum.Defining "Done": Strategies for founders to stop moving the goalposts and start celebrating measurable milestones with their teams.System and Soul Toolkit: Creating feedback rituals that move accountability from a chore to a core cultural value. ConclusionThe conversation with Stacey Bailey highlights that organizational health is a continuous practice, not a destination. By committing to clear communication and structured planning cycles, leaders can transform their teams from a group of individuals into a cohesive, high-impact leadership unit. 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!

    15 min

  6. 5D AGO

    2378 - Compassionate Leadership and Grief Support in the Workplace with AGRA’s Carl Manlan

    Navigating Grief, Leadership, and Global Opportunity: Strategic Insights from Carl ManlanIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Carl Manlan, a prolific Author and the Head of Partnerships and Business Development at AGRA. Their wide-ranging conversation delved into the profound intersection of personal loss, empathetic leadership, and the immense economic potential within African markets. Carl, who also co-hosts the Inside the Blueprint Podcast with his daughter, shares how his poetry collection, I Can Breathe, serves as a vessel for processing grief and transforming it into a leadership strength. This episode provides a masterclass for executives and founders on how to cultivate more humane, resilient workplaces while staying attuned to the intergenerational shifts shaping the future of global business. From Personal Reflection to Empathetic Organizational DesignThe modern executive often operates at a pace that leaves little room for the "inner work" required to lead with true empathy. Carl Manlan advocates for a radical return to self-reflection, citing his own practice of a 120-day writing course as the foundation for his professional clarity. By dedicating time to pause and reconnect with formative experiences, leaders can dismantle the stoic barriers that often hinder authentic connection with their teams. This process isn't merely therapeutic; it is a strategic alignment tool that allows a leader to recognize that their employees are whole people who carry invisible burdens—including grief—into the workspace every day. Creating an empathetic work environment requires moving beyond performative sympathy toward structural support. Carl emphasizes that grief is a manifestation of love and a universal human experience that doesn't simply vanish at the office door. Leaders must normalize conversations around mental well-being and loss, providing "space rather than just sympathy." This means building flexibility into operational workflows and fostering a culture where vulnerability is modeled from the top down. When a leader acknowledges their own humanity, it gives the entire organization permission to be resilient, ultimately reducing burnout and increasing long-term employee engagement. Furthermore, the conversation highlighted the necessity of intergenerational dialogue in future-proofing an organization’s culture. Through his work with his daughter, Carl demonstrates that the next generation of innovators—particularly in emerging markets like Africa—view the world through a lens of digital fluency and social impact. For businesses looking to tap into the "Africa that exists"—a continent of 1.4 billion people driven by youth and entrepreneurship—the approach must be one of partnership rather than paternalism. By bridging the gap between established leadership wisdom and the fresh curiosity of the youth, organizations can unlock new narratives of hope, healing, and unprecedented economic opportunity. About Carl ManlanCarl Manlan is a celebrated Author, poet, and international development professional. As the Head of Partnerships at AGRA, he works at the nexus of agriculture, finance, and economic transformation in Africa. He is the author of the moving poetry collection I Can Breathe and a dedicated advocate for mental health and intergenerational mentorship. About Carl Manlan OfficialCarl Manlan’s official platform serves as a hub for his creative and professional endeavors. It features his published works, including I Can Breathe, and provides resources for those interested in the Inside the Blueprint Podcast. The platform emphasizes the power of storytelling to bridge cultural and generational divides, fostering global conversations on leadership and resilience. Links Mentioned in This Episode: Carl Manlan Official WebsiteCarl Manlan on LinkedIn Key Episode HighlightsThe 120-Day Reflection: How a structured daily writing habit can sharpen executive decision-making and emotional intelligence.Grief as a Leadership Asset: Transforming personal loss into a catalyst for building high-trust, empathetic organizational cultures.The "Africa That Exists": Moving beyond risk-aversion to identify high-growth opportunities in African agriculture and tech-enabled entrepreneurship.Intergenerational Synergy: Lessons from co-hosting a podcast with a 13-year-old on how to mentor and learn from Gen Z.The Metaphor of Breath: Using poetry as a practical tool for healing and maintaining professional momentum during seasons of adversity. ConclusionCarl Manlan’s insights remind us that the most effective leaders are those who stay connected to their own humanity. By embracing reflection, honoring the grieving process, and looking toward emerging markets with humility, you can build a legacy that is both personally fulfilling and globally impactful. 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

  7. 6D AGO

    2377 - The Transformative Power of Asking and Listening with Empathy with Lushin's Shad Tidler

    Mastering the Human Element of Sales and Leadership with Shad TidlerIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Shad Tidler, a senior consultant and coach specializing in Sales and Leadership/Management at Lushin. The conversation dived deep into the psychological barriers that often prevent talented entrepreneurs from scaling their sales organizations and leading with true impact. Shad’s expertise lies in dismantling the "head trash" that complicates the sales process, helping leaders transition from a state of reactive management to one of proactive, high-performance coaching. For any founder feeling stuck in the "doer" role, this episode provides a masterclass in shifting perspective to unlock sustainable business growth. Bridging the Gap Between Sales Strategy and Leadership ExecutionA common struggle for growing businesses is the disconnect between the desire for higher revenue and the actual leadership behaviors required to support a sales team. Many founders are excellent at closing deals themselves but struggle to replicate that success within their team because they treat management as an administrative task rather than a coaching discipline. To bridge this gap, leaders must first achieve clarity on their own "sales DNA"—the underlying beliefs and habits that dictate how they interact with prospects and employees. By addressing these foundational elements, a leader can stop micromanaging the "what" and start influencing the "how," creating a culture where accountability is embraced rather than feared. Developing a high-performance sales culture also requires a fundamental shift in how we view the sales process itself: it is not about "convincing" people, but about qualifying them through rigorous discovery. Shad points out that many sales teams fail because they spend too much time chasing low-probability prospects due to a psychological need for approval. By implementing a structured, repeatable sales system, organizations can remove the emotional guesswork from the pipeline. This allows leadership to accurately forecast growth and identify specific skill gaps within their team. When sales becomes a predictable system rather than an emotional rollercoaster, the entire organization benefits from increased stability and focus. Ultimately, the most successful leaders are those who invest in their own development to stay ahead of the challenges that come with scaling. Leadership and sales are both skills that require continuous refinement and a willingness to confront uncomfortable truths about one's own performance. This is where external coaching becomes a vital asset; it provides the objective mirror necessary to spot the "head trash" that internal teams are often too close to see. By focusing on the intersection of mindset and methodology, entrepreneurs can build resilient teams that are equipped to thrive in competitive markets, ensuring that the mission of the business is supported by a robust, self-sustaining engine of growth. About Shad TidlerShad Tidler is a seasoned consultant and coach at Lushin, specializing in sales, management, and leadership development. With a background in helping businesses navigate complex growth phases, Shad focuses on the human side of business—addressing the beliefs, behaviors, and techniques that drive or hinder professional success. He is passionate about helping individuals and teams overcome psychological barriers to reach their full potential. About LushinLushin is a sales and leadership consulting firm dedicated to helping businesses achieve predictable, sustainable growth. By focusing on the psychology of sales and management, Lushin provides the training, coaching, and systems necessary to build high-performing organizations. They work with companies to refine their sales processes, develop effective leaders, and create cultures of high accountability and performance. Links Mentioned in This EpisodeLushin Website: www.lushin.comShad Tidler on LinkedIn: https://www.linkedin.com/in/shadtidler Key Episode HighlightsOvercoming "Head Trash": Understanding the psychological barriers and limiting beliefs that prevent sales professionals from asking the tough questions.The Manager vs. Coach Distinction: Why the most successful sales leaders spend their time coaching behavior rather than just managing metrics.Sales DNA and Belief Systems: How your underlying beliefs about money and authority impact your ability to close deals and lead teams.Systematizing the Discovery Process: The importance of a structured sales methodology to remove emotional bias and improve lead qualification.Cultivating Accountability: Shifting organizational culture so that team members take ownership of their results and growth. ConclusionShad Tidler’s approach reminds us that business growth is as much about personal evolution as it is about strategy. By refining the "human engine" behind your sales and leadership, you create a foundation for success that can withstand the pressures of scaling. 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 5

    2376 - Safety Tips for Biking and Marketing in Inclement Weather with Andigo's Andrew Schulkind

    Aligning Mission and Marketing: Strategic Insights from Andrew Schulkind of AndigoIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Andrew Schulkind, the Digital Strategist and Web Developer behind Andigo. Their conversation explored the critical intersection of high-level digital strategy and mission-driven business growth. Andrew shares how organizations—particularly B Corps and public benefit corporations—can bridge the gap between their core purpose and their marketing execution. This episode serves as a masterclass for leaders looking to move beyond tactical "noise" to build an authentic, long-term digital presence that reflects their true impact and drives sustainable performance. Beyond the Hype: Strategic Marketing for Mission-Driven SuccessFor many mission-driven organizations, the greatest challenge isn't a lack of purpose, but a disconnect between their internal values and their external marketing. Andrew explains that marketing is fundamentally a promise-making engine; if the operational reality of the business fails to deliver on those promises, the brand erodes. High-achieving founders often find that their digital presence has become a "snapshot" that no longer reflects the "moving picture" of their evolving company. To solve this, businesses must transition from one-off projects to a model of continuous improvement, where messaging and operations are in constant lockstep to ensure every customer interaction reinforces the brand's integrity. In an era dominated by the rapid rise of AI and automation, the competitive advantage for B2B firms is shifting away from mere content production toward high-level strategy and radical authenticity. While AI can act as a powerful productivity expander, it cannot replace the strategic direction required to navigate complex market shifts. Andrew advocates for a "flight to strategy," where leaders use technology to automate repetitive tasks while leaning deeper into the human nuances of storytelling and relationship-building. Audiences today crave a real human voice behind the brand, and businesses that leverage AI to free up their team's creative capacity—rather than simply replacing it—will be the ones that build lasting trust. Success in the digital landscape also requires a shift in how agencies and clients collaborate. Rather than transactional vendor relationships, Andrew emphasizes the value of flexible, long-term partnerships that allow for agile pivots as market conditions change. By implementing robust measurement systems and maintaining a focus on transparency, organizations can ensure their marketing investments are yielding a tangible return on impact. This approach allows mission-driven leaders to stay focused on their "double bottom line"—profit and purpose—knowing that their digital strategy is robust enough to support both without compromising the authenticity that defines their brand. About Andrew SchulkindAndrew Schulkind is a veteran Digital Strategist and Web Developer with a deep passion for helping mission-driven businesses thrive. As an avid year-round cyclist and advocate for B Corps, Andrew brings a unique perspective on resilience and alignment to every project. He is known for his ability to translate complex technical requirements into clear, strategic growth paths for organizations that prioritize impact. About AndigoAndigo is a digital strategy and web development agency that specializes in working with B2B firms, public benefit corporations, and mission-driven organizations. The agency focuses on building long-term, flexible partnerships that prioritize continuous improvement, authentic storytelling, and strategic alignment. Andigo helps clients move beyond surface-level marketing to create digital systems that truly reflect and amplify their organizational mission. Links Mentioned in This EpisodeAndigo Official WebsiteAndrew Schulkind on LinkedIn Key Episode HighlightsThe Promise-Delivery Loop: Why marketing alignment is the foundation of brand trust and long-term customer retention.The "Flight to Strategy": How to utilize AI as a task-automation tool while doubling down on human-led strategic direction.Resilience in Motion: Lessons from year-round cycling on preparation, visibility, and adapting to harsh environmental shifts.Mission-Driven Storytelling: Leveraging a company's "why" to create more compelling, authentic B2B narratives.Project vs. Partnership: The benefits of moving toward a continuous improvement model rather than stagnant, one-off web projects. ConclusionThis conversation with Andrew Schulkind highlights that in a world of increasing automation, the most successful brands are those that remain anchored in their mission and human connection. By aligning your operations with your marketing promises, you create a resilient foundation for growth that transcends digital trends. 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
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

Information

  • 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