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The Thoughtful Entrepreneur

The Thoughtful Entrepreneur

Author: Josh Elledge of UpMyInfluence.com

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You’re gonna love this DAILY, commercial-free entrepreneur spotlight show. We feature CEOs and founders of 6-9 figure B2B companies. Agencies, coaches, consultants, and other leaders share not only their success stories - but their advice for business leaders focused on business growth.

You’re going to hear real stories from real people all in 15-25 minutes time - perfect for your commute.

On this podcast, your host, Josh Elledge encourages entrepreneurs to share not only their expertise but their stories and their hearts.

We believe that every person has a unique message which can positively impact the world. Even YOU! If you’d like to be featured on The Thoughtful Entrepreneur, apply here: https://UpMyInfluence.com/guest/
2288 Episodes
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Mastering B2B Lead Generation in the Age of AI: Expert Insights from Bill RiceIn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Bill Rice, founder of Bill Rice Strategy Group and Kaleidico. Bill shares his expertise in B2B marketing, lead generation, and the evolving role of AI in shaping how businesses attract and convert clients. Drawing from decades of experience in fintech, mortgage lending, and legal industries, Bill offers actionable insights for executives and agencies looking to thrive in a rapidly changing digital landscape.The New Rules of B2B Lead GenerationBill explains that B2B marketing has evolved beyond traditional methods like cold outreach and Google Ads. Today’s success depends on creating digital surface area—the online footprint of content, profiles, and engagement that helps AI and algorithms recognize your expertise. He emphasizes that consistent, clear messaging across blogs, websites, and social platforms allows both search engines and large language models (like ChatGPT) to identify and recommend your brand as an authority.A key part of Bill’s strategy is leveraging LinkedIn for executive visibility. He encourages business leaders to post regularly, engage thoughtfully, and use the platform as a stage for thought leadership. Sharing authentic stories, insights, and industry perspectives humanizes your brand while establishing credibility. This kind of visibility not only attracts potential clients but also builds trust and familiarity long before the sales conversation begins.Bill also discusses how AI and large language models are reshaping the buyer’s journey. AI-driven referrals are becoming more influential than traditional SEO, as they provide context-aware recommendations tailored to user needs. He advises business owners to ensure their digital content is well-structured, easy to interpret, and consistently reinforces their niche expertise. By combining thoughtful content creation, AI awareness, and genuine personal branding, companies can build scalable, first-party lead generation systems that produce sustainable results.About Bill RiceBill Rice is the Founder of Bill Rice Strategy Group and Kaleidico, two leading agencies specializing in B2B marketing and lead generation. With over 20 years of experience across finance, law, and senior living sectors, Bill helps executives and organizations develop first-party lead systems, optimize digital presence, and harness AI for measurable business growth. He is also the creator of The Executive Brief, a weekly newsletter featuring actionable insights for leaders navigating the intersection of marketing and technology.About Bill Rice Strategy GroupBill Rice Strategy Group is a marketing consultancy that helps businesses build first-party lead generation systems through strategy, content creation, and AI-driven insights. With a focus on long-term growth and client ownership of marketing assets, the firm empowers organizations to elevate their brand authority, generate consistent leads, and adapt to the rapidly evolving digital landscape.Links Mentioned in this EpisodeBill Rice Strategy GroupBill Rice LinkedIn ProfileThe Executive Brief NewsletterKey Episode HighlightsHow AI is reshaping B2B lead generation and client discoveryWhy digital surface area boosts visibility and credibilityThe power of LinkedIn for executive thought leadershipBuilding sustainable, first-party lead...
Realigning Your Business with Passion: Expert Insights from Kara DuffyIn this episode of The Thoughtful Entrepreneur, host Josh Elledge interviews Kara Duffy, CEO and Founder of KDCC International, who helps entrepreneurs and business owners realign their work with their passions and strengths. Kara shares how reconnecting with what you love can reignite purpose, boost profitability, and prevent burnout. Through her experience coaching creative leaders and building businesses, she offers clear, actionable steps to simplify operations, find your “zone of genius,” and create a company that feels as good as it performs.Building a Passion-Aligned BusinessKara believes that success starts with alignment—when your business reflects your purpose and energizes you daily. She explains that many entrepreneurs drift from their passion over time, taking on clients or projects that drain creativity and joy. Her “lemonade stand” philosophy encourages founders to strip back to what they do best and build from that foundation. By focusing on a single core offering, simplifying operations, and delegating distractions, business owners can regain clarity, increase profitability, and rediscover fulfillment in their work.Operating in your “zone of genius,” Kara says, means spending most of your time on high-value, joyful activities. She urges leaders to delegate or eliminate everything outside that zone and to audit weekly tasks for alignment. Through this lens, even niche businesses—like boutique creatives or specialists serving small, passionate audiences—can thrive when they stay authentic and focused. When clarity replaces clutter, it becomes easier to attract dream clients who align with your mission and values.Kara also emphasizes that business is a lifestyle, not just a job. She encourages entrepreneurs to design companies that support their personal rhythms and long-term well-being. Whether it’s taking “mini holidays” to recharge or fostering genuine client relationships, the goal is to create a sustainable balance. Her signature mantra—“Stop Selling, Start Sharing”—captures her belief that authenticity and generosity are the true engines of business growth. When you lead with purpose and share what you love, success follows naturally.About Kara DuffyKara Duffy is the CEO and Founder of KDCC International, a business coaching and consulting firm dedicated to helping entrepreneurs and creative leaders build businesses that are both profitable and purposeful. With extensive experience guiding founders through growth and realignment, Kara helps clients simplify, scale, and reconnect with their mission. She is also the author of Stop Selling, Start Sharing, a guide to authentic, purpose-driven business.About KDCC InternationalKDCC International empowers entrepreneurs and teams to build high-impact, passion-driven businesses through strategic coaching, workshops, and consulting. From clarity and culture to profitability and purpose, KDCC helps leaders align their operations with their vision—creating companies that thrive from the inside out.Links Mentioned in this EpisodeKDCC InternationalKara Duffy LinkedIn ProfileKey Episode HighlightsHow to simplify your business using the “lemonade stand” approachWhy working in your “zone of genius” leads to sustainable successHow to declutter your business like the KonMari MethodTurning your business into a lifestyle you loveBuilding authentic connections through sharing, not sellingConclusionAs Kara Duffy reminds us, business success isn’t just about growth—it’s about alignment. When your...
When Is Your Business Ready for a Fractional CFO? Expert Insights from Laresa McIntyreAs your business scales, the financial landscape becomes increasingly complex. Many founders find themselves overwhelmed by cash flow management, forecasting, and financial decision-making—realizing their passion alone isn’t enough to sustain growth. In this episode, host Josh Elledge interviews Laresa McIntyre, fractional CFO and Founder of Rockbridge CFO, who shares her insights on when to bring in a fractional CFO, how to prepare for that step, and how doing so can transform your business operations and confidence.The Right Time to Hire a Fractional CFOLaresa explains that a fractional CFO is a part-time financial executive who provides strategic planning, forecasting, and financial insight—without the cost of a full-time hire. Businesses typically benefit when revenue reaches the $1M–$2M mark or when decision-making starts to rely too heavily on gut instinct instead of data. She highlights clear signs that a company is ready for financial leadership: outgrowing basic tools like QuickBooks, feeling uncertain about profitability, or needing clarity around cash flow and personnel costs.A fractional CFO doesn’t just manage numbers—they partner with founders to bring order, foresight, and peace of mind. Laresa shares how implementing more detailed financial reporting and proactive cash flow forecasting helps business owners understand where their money is going, where it should go next, and how to allocate it efficiently. This support allows leaders to step back from financial stress and focus on strategy, growth, and innovation instead.For founders still below seven figures, Laresa recommends starting early by setting up robust accounting systems and forecasting tools. Preparation ensures a fractional CFO can deliver maximum value once engaged. By building these systems in advance, founders avoid reactive decisions and gain clarity on how each financial move impacts long-term scalability.About Laresa McIntyreLaresa McIntyre is the Founder and Fractional CFO at Rockbridge CFO, where she helps businesses gain financial clarity, improve profitability, and scale strategically. With years of experience supporting founders and executive teams, she specializes in transforming financial chaos into actionable growth strategies.About Rockbridge CFORockbridge CFO provides strategic financial leadership for growing companies through fractional CFO services. The firm focuses on forecasting, profitability analysis, and cash flow management—empowering business owners to make confident, data-driven decisions without the expense of a full-time CFO.Links Mentioned in this EpisodeRockbridge CFOLaresa McIntyre LinkedIn ProfileKey Episode HighlightsSigns your business is ready for a fractional CFOHow financial forecasting improves decision-makingCommon gaps in accounting systems for scaling companiesThe emotional and strategic benefits of CFO partnershipHow to prepare your financial foundation before reaching seven figuresConclusionHiring a fractional CFO isn’t just about managing your finances—it’s about reclaiming your time, focus, and confidence as a leader. As Laresa McIntyre explains, the right time to bring in a CFO is when you’re ready to grow with clarity and strategy instead of stress and guesswork. Whether your business is at $500K or $5M, proactive financial leadership can set the foundation for sustainable, scalable success.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of...
Navigating the 2025 SMB Landscape: Proactive Tax Strategies and Expert Insights from Adam WilliamsSmall and medium-sized business owners are facing unprecedented challenges in 2025, from rapid legal changes to AI-driven disruption. In a recent episode, Josh Elledge sat down with Adam Williams, author and Co-founder of Pennywise Tax Strategies, to explore actionable strategies for SMB founders navigating complex tax, legal, and operational environments. Adam shared insights on proactive tax planning, leveraging expert advisors, and adapting to technological changes to help businesses thrive in an increasingly dynamic landscape.The Power of Proactive Tax PlanningAdam emphasizes that reactive tax preparation is no longer sufficient for SMBs looking to maximize profits and future-proof their businesses. Forward-thinking strategies like auditing profit and loss statements, employing family members, leveraging the Augusta Rule, choosing the right business entity, and utilizing cost segregation can save businesses significant money while maintaining compliance. He also highlights the importance of ongoing education and expert advisors, ensuring owners can confidently navigate new laws, AI integration, and changing economic conditions.Proactive planning goes beyond minimizing taxes—it’s about optimizing operations and leveraging every available advantage. SMB owners can use these strategies to automate processes, structure their teams effectively, and ensure every deduction, credit, or exemption is captured. Adam’s guidance demonstrates how combining thoughtful planning with expert support allows businesses to remain agile, profitable, and competitive in 2025 and beyond.Entrepreneurs who implement these strategies not only reduce risk but also position their businesses for sustainable growth. From cost-saving opportunities to AI-driven efficiency improvements, the insights Adam shared provide a clear roadmap for SMB founders seeking long-term success. By taking a proactive approach, business owners can reclaim control over their finances, optimize operations, and confidently scale their enterprises.About Adam WilliamsAdam Williams is the Co-founder of Pennywise Tax Strategies and a seasoned author focused on actionable tax and business advice for small and medium-sized enterprises. With deep expertise in tax planning, business law, and strategic consulting, Adam empowers SMB owners to make informed decisions that maximize profits and minimize risk.About Pennywise Tax StrategiesPennywise Tax Strategies helps small and medium businesses implement proactive tax planning, optimize deductions, and leverage financial strategies to grow efficiently. Their team specializes in forward-looking solutions that combine expert knowledge with practical, actionable tactics for entrepreneurs navigating a rapidly evolving business environment.Links Mentioned in this EpisodePennywise Tax StrategiesAdam Williams LinkedInKey Episode HighlightsHow SMBs can navigate complex tax and legal changes in 2025Strategies for proactive tax planning and financial optimizationLeveraging expert advisors and mastering profit and loss statementsTips for employing family members, leveraging the Augusta Rule, and entity selectionInsights on cost segregation and maximizing deductions for SMBsConclusionThe 2025 SMB environment demands proactive planning, strategic partnerships, and a keen understanding of tax and operational opportunities. Adam Williams’ insights provide a roadmap for entrepreneurs seeking to thrive amid uncertainty by optimizing finances, leveraging expert guidance, and positioning...
Growth Through Acquisition: Lessons from Navy Veteran and Entrepreneur Gary MacDermidEntrepreneurship often requires both discipline and strategic vision, and few embody that combination like Gary MacDermid—a Navy veteran turned successful business acquirer, investor, and author. In a recent episode of The Thoughtful Entrepreneur, host Josh Elledge sat down with Gary to discuss his journey from military service to civilian business leadership, offering actionable strategies for veterans and entrepreneurs alike. This post distills key insights from the conversation, focusing on growth through acquisition, creative financing, and the importance of intentional goal-setting.Accelerating Growth Through Acquisition and Strategic Goal-SettingGary emphasizes that acquiring businesses—rather than relying solely on organic growth—can rapidly scale revenue, talent, and operational capacity. By identifying complementary businesses and overlaying high-value services, entrepreneurs can unlock immediate opportunities and enhance client value. Creative financing options, such as seller financing, SBA loans, and private investors, make acquisitions accessible even without deep upfront capital, allowing business owners to pursue strategic growth without overextending resources.Veterans, in particular, benefit from leveraging military discipline and intentional goal-setting, which Gary details in his book Set Your Own Goals or Someone Else Will. He recommends defining clear milestones, breaking down actionable steps, and seeking mentorship or peer accountability to navigate complex business decisions effectively. Beyond acquisition strategies, Gary stresses the importance of cultural integration and communication to ensure smooth transitions for both clients and staff, ensuring that growth is sustainable rather than just rapid.For all entrepreneurs, Gary underscores the value of overlaying high-ticket services on acquired businesses, continuously learning from new markets, and integrating processes that drive efficiency. Whether transitioning from military service or expanding an existing business, the principles of acquisition, strategic financing, and clear goal-setting serve as powerful levers to accelerate success.About Gary MacDermidGary MacDermid is a Navy veteran, investor, business acquirer, and author of Set Your Own Goals or Someone Else Will. He leverages his military experience and entrepreneurial expertise to help veterans, career changers, and business leaders strategically grow and scale their businesses.About Gary’s CompanyGary specializes in growth through acquisition, creative financing, and advisory services that empower entrepreneurs to expand efficiently while maintaining operational and cultural integrity. His methods help businesses unlock hidden value and pursue strategic opportunities with confidence.Links Mentioned in This EpisodeGary MacDermid Website: https://garymacdermid.comBook: Set Your Own Goals or Someone Else WillKey Episode HighlightsGary’s journey from Navy service to entrepreneurshipBenefits of growth through acquisition over organic growthStep-by-step approach to buying and integrating a businessCreative financing strategies: seller financing, SBA loans, private investorsOverlaying high-ticket services to maximize revenueIntentional goal-setting framework for veterans and career changersConclusionGary MacDermid’s insights demonstrate that disciplined strategy, smart acquisition, and intentional goal-setting are essential tools for accelerating growth. By leveraging military experience, creative financing, and high-value service overlays, entrepreneurs and veterans alike can unlock...
Mastering Social Media Advertising in 2024: Expert Insights from Madison Hollimon of Mad Marketing HouseIn the rapidly evolving world of social media marketing, staying ahead of platform trends, AI tools, and audience expectations is critical. In a recent podcast episode, Josh Elledge interviewed Madison Hollimon, CEO and Founder of Mad Marketing House, who shared her expertise in content creation, paid advertising, and user-generated content (UGC) strategies. This post breaks down key insights and actionable tips for businesses looking to optimize their social media campaigns and maximize engagement in 2024.Navigating Paid Ads, UGC, and AI in Social Media MarketingMadison emphasizes that effective social media marketing requires blending creativity with data-driven strategy. By leveraging authentic UGC, businesses can increase engagement and build trust, while paid advertising helps amplify reach and drive conversions. Combining AI tools with human oversight ensures campaigns are optimized efficiently without losing the personal touch that resonates with audiences.She also highlights the differences between B2B and B2C advertising, explaining that B2B campaigns require precise targeting on platforms like LinkedIn, while B2C campaigns rely on broad reach across Meta and TikTok. Madison stresses that paid advertising is most effective when aligned with strategic goals, proper budgeting, and ongoing monitoring, emphasizing that quick wins come from smart investments rather than guesswork.Finally, Madison encourages brands to embrace authenticity and storytelling while adopting AI and automation cautiously. Keeping content relatable and visually appealing ensures campaigns stand out amid algorithm changes and evolving consumer behavior. Businesses that blend technology with creativity are positioned to achieve higher ROI and long-term brand loyalty.About Madison HollimonMadison Hollimon is the CEO and Founder of Mad Marketing House, a full-service social media marketing agency specializing in content creation, paid advertising, and strategic campaigns for both B2B and B2C brands. With a focus on combining creativity, strategy, and data, Madison helps businesses scale their social presence and engage audiences effectively.About Mad Marketing HouseMad Marketing House is a creative agency that helps businesses craft authentic content and implement high-performing social media campaigns. Leveraging UGC, AI tools, and strategic paid advertising, the agency works with entrepreneurs, product-based businesses, and personal brands to maximize engagement, conversions, and ROI.Links Mentioned in this EpisodeMad Marketing House WebsiteMadison Hollimon LinkedInInstagram: @madmarketinghouseKey Episode HighlightsThe importance of authentic user-generated content for engagement and trust.How AI and automation can optimize campaigns without replacing human oversight.Strategic differences between B2B and B2C social media advertising.Tips for paid ad budgeting, targeting, and monitoring to maximize ROI.Future trends in social media marketing and content strategy.ConclusionSocial media marketing in 2024 demands a balance of creativity, strategy, and technological savvy. Madison Hollimon’s insights highlight how brands can leverage UGC, paid advertising, and AI tools to drive engagement and achieve measurable results while staying authentic and audience-focused.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful...
Sustainable Digital Advertising: How Purpose-Driven Brands Can Reduce Their Carbon Footprint and Boost PerformanceDigital advertising powers much of the online economy, but it comes with a hidden cost: a significant environmental impact. In a recent podcast, Josh Elledge spoke with Avril Tomlin-Hood, CEO & Founder of boa, a strategic sustainable digital media buying agency. They explored how brands can take meaningful action to reduce emissions while improving ad performance, offering practical strategies for purpose-driven marketing.Making Digital Advertising Sustainable Without Sacrificing PerformanceAvril explains that digital ads consume energy across servers, data centers, and real-time bidding platforms, creating “scope 3” emissions that many brands overlook. She emphasizes the importance of auditing campaigns, measuring emissions, and eliminating waste in the media supply chain. By optimizing targeting, frequency, and placements, companies can reduce unnecessary impressions and improve return on ad spend.Choosing sustainable partners and platforms is another key step. Boa encourages brands to prioritize agencies and publishers that use renewable energy and have verified carbon reduction goals. Communicating these efforts authentically—through case studies, blog posts, and social media—helps brands build trust and demonstrate real commitment to sustainability.Finally, Avril highlights the growing role of AI and the challenges of “walled gardens” like Google and Meta, which can complicate planning while increasing energy consumption. She advises marketers to stay agile, evaluate environmental impact alongside campaign effectiveness, and start with small improvements that scale over time. Sustainable advertising isn’t just responsible—it’s often more efficient and profitable.About Avril Tomlin-HoodAvril Tomlin-Hood is CEO & Founder of boa, a strategic sustainable digital media buying agency. With a focus on purpose-driven brands, she helps businesses reduce their digital carbon footprint while optimizing advertising performance and audience engagement.About boaBoa partners with companies to deliver eco-conscious media buying solutions that prioritize both performance and sustainability. Their services include auditing digital campaigns, optimizing targeting, and guiding brands toward greener platforms and practices.Links Mentioned in This Episodeboa WebsiteAvril Tomlin-Hood LinkedInKey Episode HighlightsUnderstanding the carbon footprint of digital advertisingAudit, measure, and reduce emissions in ad campaignsOptimizing targeting and frequency to improve efficiencyChoosing sustainable partners and platformsCommunicating sustainability efforts authenticallyConclusionSustainable digital advertising is no longer optional for brands that want to thrive in a resource-conscious world. By reducing emissions, eliminating waste, and partnering with eco-conscious platforms, marketers can achieve better performance, build trust with audiences, and make a meaningful impact on the environment.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here »
Unlocking Business Growth: Expert Insights from Sandy Moll, CEO of Advanced Business SolutionsIn a recent episode of The Thoughtful Entrepreneur, host Josh Elledge interviewed Sandy Moll, CEO and founder of Advanced Business Solutions (ABS). With nearly two decades of experience guiding banks, credit unions, and small to medium-sized businesses, Sandy shared her unique approach to leadership, operational excellence, and sustainable business growth. This post distills the main insights from their conversation, offering practical strategies for founders, business owners, and leaders looking to scale effectively while keeping their teams engaged.The ABS Approach: People, Processes, and Strategic ClaritySandy emphasizes that real business growth begins with a clear understanding of the problem you solve and the unique value you bring. ABS helps clients identify their core challenges, streamline operational processes, and implement strategic frameworks that allow teams to execute effectively. By combining personalized coaching with actionable systems, ABS ensures that businesses are set up for both immediate results and long-term scalability.Another key aspect of ABS’s methodology is the focus on people. Sandy highlights the importance of aligning team members with the company’s mission, developing leadership at every level, and fostering a culture that encourages accountability and innovation. This people-first approach reduces friction, increases productivity, and empowers employees to contribute meaningfully to the organization’s success.Finally, ABS integrates technology and modern tools to enhance business efficiency without overwhelming leadership or teams. From leveraging AI to automate repetitive tasks to using project management platforms to track outcomes, Sandy demonstrates how combining human expertise with smart systems drives clarity, better decision-making, and sustainable growth. This balanced approach allows founders to focus on high-impact initiatives while trusting their teams to execute effectively.About Sandy MollSandy Moll is the CEO and founder of Advanced Business Solutions (ABS), bringing nearly 20 years of experience in helping SMBs, credit unions, and banks achieve clarity, efficiency, and scalable growth. She is passionate about combining operational strategy, leadership coaching, and technology to create sustainable, people-centered business solutions.About Advanced Business Solutions (ABS)ABS is a consulting and business solutions firm specializing in operational efficiency, leadership development, strategic planning, and interim staffing. With a client-first approach, ABS helps organizations streamline processes, develop high-performing teams, and implement strategies that drive measurable growth.Links Mentioned in this EpisodeABS WebsiteConnect with Sandy Moll on LinkedInKey Episode HighlightsThe power of identifying the problem your business solvesAligning team members with organizational mission and cultureIntegrating technology to improve efficiency without overcomplicating operationsLeadership strategies for sustainable growth and accountabilityTips for founders navigating uncertainty and scaling effectivelyConclusionSandy Moll’s insights provide a clear roadmap for leaders seeking growth without sacrificing culture or clarity. By combining strategic frameworks, people-first leadership, and technology integration, founders and executives can scale their businesses sustainably while empowering their teams to perform at their best.🎧 More from UpMyInfluence🎙️ Want to be featured on The Thoughtful...
How Gelt is Transforming Tax Services: Insights from Founder Tal BinderIn a recent episode, Josh Elledge interviewed Tal Binder, CEO and Founder of Gelt, to discuss how his tech-driven tax company is redefining tax compliance, planning, and strategy for high net worth individuals and businesses. Tal shared his journey, the integration of AI and human expertise, and the practical ways Gelt delivers superior service in a fast-evolving tax landscape. This post highlights key takeaways, actionable insights, and tips for anyone considering a modern approach to tax services.The Gelt Approach: Blending AI with Human ExpertiseGelt’s model is centered on combining advanced technology with expert human oversight. Tal Binder emphasized that AI acts as a productivity multiplier, enabling tax professionals to work faster and more accurately, while a senior tax manager reviews all filings to mitigate risk and ensure precision.The company focuses on three core services: tax compliance, planning, and strategy, allowing clients to proactively manage obligations, optimize deductions, and structure finances for maximum efficiency. By automating repetitive tasks, Gelt’s platform frees experts to deliver higher-value analysis and guidance tailored to each client’s situation.Tal also stressed the importance of client experience and transparency. Every client receives a dedicated point of contact, Gelt partners with complementary service providers when necessary, and pricing is structured to reflect complexity and value. These elements make Gelt a unique alternative to traditional firms, ensuring both high-tech efficiency and personalized service.About Tal BinderTal Binder is the Founder and CEO of Gelt, a Tampa-based company focused on delivering tech-enabled tax solutions for high net worth individuals and businesses. Tal combines extensive experience in finance, technology, and entrepreneurship to streamline tax compliance, planning, and strategy.About GeltGelt is a modern tax services firm that integrates AI with human expertise to provide high net worth clients and businesses with accurate, efficient, and actionable tax solutions. Their approach emphasizes compliance, strategic planning, and personalized client service, positioning them as an innovative alternative to traditional firms.Links Mentioned in this EpisodeGelt WebsiteTal Binder LinkedIn ProfileKey Episode HighlightsHow Gelt combines AI and human expertise to enhance tax servicesThe three core services: compliance, planning, and strategyDedicated senior tax managers for personalized client serviceTransparent pricing and partnership approach for businesses and individualsPractical guidance on engaging with tech-enabled tax solutionsConclusionGelt demonstrates that modern tax services can be both high-tech and highly personal, enabling clients to optimize their financial outcomes while reducing complexity. By integrating AI with expert oversight, Gelt provides a scalable, accurate, and proactive approach to tax compliance, planning, and strategy.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here »
Unlocking Scalable Leadership and Culture: Expert Insights from Esther Weinberg of The Ready ZoneIn a rapidly evolving business landscape, founders and executive teams face the dual challenge of scaling operations while retaining their top talent and organizational sanity. In a recent episode, Josh Elledge interviewed Esther Weinberg, Founder & Chief Leadership Development Officer of The Ready Zone, who shared actionable strategies for building resilient leadership, cultivating strong culture, and preparing teams for sustainable growth. Drawing from her experience across entertainment and international development, Esther provides a practical roadmap for leaders navigating fast-growing organizations.Building Leadership Depth and Organizational ResilienceEsther emphasizes the “Three Ts”—Talent, Traction, and Technology—as the core pillars of scalable leadership. Talent focuses on attracting, developing, and retaining the right people, while Traction ensures that execution aligns with strategy. Technology acts as both an enabler and a source of stress, and leaders must help teams integrate digital tools without compromising culture.Scaling effectively requires recognizing the leadership gap that often emerges as companies grow. Founders cannot do it alone; mid-level and senior leaders need development, clear expectations, and accountability frameworks. Esther advises using structured approaches like the Five A’s—Aware, Accurate, Acquire, Accountability, and Action—to empower leaders to reflect, learn, and implement change systematically.Practical application of these principles is critical. Esther recommends auditing your leadership team, clarifying expectations, investing in development, adopting the Five A’s in everyday operations, and fostering open, tough conversations. Balancing people and technology ensures that teams stay engaged while adapting to AI and digital transformation pressures, creating a resilient and high-performing organization.About Esther WeinbergEsther Weinberg is the Founder & Chief Leadership Development Officer of The Ready Zone. With a career spanning entertainment and international development, she specializes in helping high-growth organizations build leadership depth, cultivate culture, and scale sustainably while keeping teams engaged and effective.About The Ready ZoneThe Ready Zone equips leaders and executive teams with practical frameworks, tools, and coaching programs designed to improve leadership effectiveness, team alignment, and organizational resilience. Their programs combine actionable strategies, personalized coaching, and change management guidance for leaders navigating complex growth challenges.Links Mentioned in This EpisodeEsther Weinberg LinkedIn ProfileThe Ready ZoneKey Episode HighlightsThe Three Ts framework: Talent, Traction, and TechnologyLeadership gaps in scaling organizations and the importance of mid-level developmentThe Five A’s framework for personal and team leadership transformationPractical steps for auditing and developing leadership talentBalancing AI, digital transformation, and people-first leadershipConclusionScaling a business successfully requires more than strategy—it requires depth in leadership, intentional culture building, and the courage to have tough conversations. Esther Weinberg’s frameworks provide actionable guidance for founders and executive teams to grow sustainably while keeping their people and performance aligned.🎧 More from UpMyInfluence🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule
Unlocking the Power of Email & SMS Marketing for E-Commerce: Expert Insights from Nikita VakhrushevIn the fast-paced world of e-commerce, many brands focus heavily on acquisition channels like TikTok, Google Ads, and Instagram, often overlooking one of their most valuable assets: their existing customer list. In a recent episode, Josh Elledge spoke with Nikita Vakhrushev, CEO & Chief Strategist of Aspekt, about how e-commerce businesses can maximize revenue and retention through smart email and SMS marketing. Nikita shared actionable strategies to engage warm audiences, optimize backend flows, and leverage design and segmentation for scalable growth.The Value of Backend Marketing for E-CommerceFocusing on existing customers is often more profitable than constantly chasing new ones. Nikita emphasizes that a well-maintained warm list—subscribers who have opted in—can drive repeat purchases and boost engagement. By auditing current flows, segmenting audiences, and sending value-driven communications, brands can increase revenue while fostering long-term loyalty.Modern email and SMS marketing also demands careful attention to privacy, consent, and deliverability. Platforms must respect double opt-ins, frequency preferences, and regulatory compliance to maintain subscriber trust. Nikita recommends staying current with evolving regulations and testing messaging to optimize engagement.Finally, leveraging strategic agency support can multiply results. Agencies like Aspekt provide audits, segmentation, automation, and expert design to ensure every message is impactful. Clear communication, transparency, and personalized service are key to achieving measurable ROI and scaling backend marketing efficiently.About Nikita VakhrushevNikita Vakhrushev is the CEO & Chief Strategist of Aspekt, a leading agency specializing in email and SMS marketing for e-commerce brands. With years of experience managing hundreds of accounts, he focuses on helping businesses increase revenue, engagement, and customer retention through backend marketing strategies.About AspektAspekt provides white-glove email and SMS marketing services for direct-to-consumer brands. Their team specializes in audits, segmentation, automation, and visually compelling campaigns designed to convert and scale, while maintaining transparency and measurable results.Links Mentioned in this EpisodeAspekt WebsiteNikita Vakhrushev LinkedinKey Episode HighlightsThe importance of backend marketing over constant customer acquisition.Leveraging warm lists and subscriber segmentation for higher ROI.Privacy, consent, and deliverability trends impacting email and SMS.Case study: Transforming a legacy brand’s email revenue.Choosing agencies that provide transparency, personalization, and measurable results.ConclusionEmail and SMS marketing are powerful, revenue-driving tools when approached strategically. By focusing on your warm audience, optimizing backend flows, and embracing modern design and compliance standards, e-commerce brands can unlock sustainable growth and maximize lifetime customer value.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here »
The CEO’s Journey: Actionable Insights from Patrick Thean on Leadership, Strategy, and ExecutionIn a recent episode of The Thoughtful Entrepreneur, host Josh Elledge interviewed Patrick Thean, co-founder of Rhythm Systems®, bestselling author, and executive coach. Patrick shared actionable strategies for CEOs to scale high-growth companies, build strong cultures, and implement practical frameworks for leadership success. This blog distills key insights, providing guidance for leaders seeking to elevate their organizational performance and personal impact.The Real Role of a CEO: Beyond the Job TitlePatrick emphasizes that the CEO role evolves with company size: startup CEOs are hands-on with day-to-day operations, mid-market leaders focus on vision and enabling teams, and enterprise CEOs prioritize strategy, culture, and executive team alignment. He outlines seven practices for CEO success, including personal growth, curiosity, building early warning systems, aligning teams, fostering culture, developing talent ecosystems, and crafting customer-centric strategies. Implementing these practices helps CEOs empower their teams, prevent costly misalignment, and drive sustainable organizational growth.Personal development is foundational to effective leadership. Patrick recommends regular self-assessment, working with coaches or peer groups, and committing to continuous learning to ensure personal growth keeps pace with company expansion. A strong culture and aligned talent ecosystem amplify the CEO’s impact, enabling teams to execute effectively while sustaining engagement, morale, and performance.Tools like Rhythm Systems® act as a “CEO’s software,” providing a platform for strategy execution, goal tracking, and real-time performance visibility. By combining practical frameworks with software support, CEOs can transform high-level vision into operational reality, enhance accountability, and maintain clarity across their organization. The integration of personal growth, structured practices, and strategic tools equips leaders to thrive in high-growth environments.About Patrick TheanPatrick Thean is a serial entrepreneur, executive coach, and co-founder of Rhythm Systems®, a SaaS platform designed to help CEOs execute strategy, align priorities, and drive performance. His books, podcast, and coaching provide actionable insights for leaders navigating growth, culture-building, and organizational alignment.About Rhythm Systems®Rhythm Systems® provides a platform that helps CEOs and leadership teams implement strategy, track execution, and maintain alignment across departments. The software combines strategic planning, measurable goals, and real-time performance tracking, supporting sustainable business growth.Links Mentioned in this EpisodeRhythm Systems®Patrick Thean LinkedInKey Episode HighlightsThe CEO role changes depending on company size and growth stage.Seven practices for CEO success: self-growth, curiosity, early warning systems, alignment, culture, talent, and customer strategy.Personal development and accountability are crucial for effective leadership.Culture and talent ecosystems drive sustained organizational performance.Tools like Rhythm Systems® enhance execution, alignment, and clarity.ConclusionPatrick Thean’s insights provide CEOs with a roadmap to balance personal growth, strategic leadership, and operational alignment. By implementing his seven practices and leveraging tools like Rhythm Systems®, leaders can empower teams, sustain high performance, and drive long-term business success.🎧 More from UpMyInfluence:🎙️...
Bridging the Gap: How Snow Leopard AI Empowers Enterprises with Real-Time Data for AI AgentsIn today’s fast-paced business world, the ability to connect AI agents to real-time, operational data is crucial for decision-making and efficiency. In a recent episode, host Josh Elledge interviewed Deepti Srivastava, Founder and CEO of Snow Leopard AI, to discuss how enterprises can leverage AI agents effectively while ensuring access to accurate, actionable data. Deepti shares practical guidance for integrating AI, overcoming technical challenges, and maximizing the value of AI-driven workflowsThe Role of Real-Time Data in AI Agent SuccessAI agents are transforming how businesses operate, but their effectiveness hinges on real-time, accurate data. Deepti explains that AI is only as strong as the data it consumes, and fragmented or outdated data can lead to poor outcomes. Enterprises face challenges integrating AI into existing infrastructures, bridging gaps between AI teams and operational systems, and maintaining data security and freshness.Snow Leopard AI provides a platform that abstracts these infrastructure complexities, allowing AI teams to focus on business logic instead of plumbing. By connecting AI agents directly to operational data sources—ranging from SQL databases to SaaS APIs—companies can automate workflows, improve decision-making, and unlock insights that were previously siloed.For organizations beginning their AI journey, Deepti recommends starting with high-impact, low-risk use cases such as customer support, internal knowledge agents, or finance operations. Once proven, the deployment can expand to more complex workflows, leveraging both structured and unstructured data to maximize AI’s value.About Deepti SrivastavaDeepti Srivastava is the Founder and CEO of Snow Leopard AI and a seasoned expert in AI infrastructure. She draws on her experience at Google and Oracle to help enterprises connect generative AI agents with real-time business data, enabling faster, more accurate decisions across industries.About Snow Leopard AISnow Leopard AI provides a platform that bridges AI agents with operational enterprise data, simplifying integration, ensuring security, and supporting scalable AI deployment. The platform empowers businesses to automate workflows, improve decision-making, and harness AI across finance, healthcare, SaaS, and legal sectors.Links Mentioned in this EpisodeWebsite: snowleopard.aiLinkedIn: Deepti SrivastavaKey Episode HighlightsUnderstanding the critical role of real-time, operational data for AI agentsOvercoming enterprise integration challenges and infrastructure gapsPractical steps for deploying AI agents across customer support, finance, and internal systemsLeveraging unstructured data for multimodal AI applicationsExpert recommendations for governance, data quality, and phased adoptionConclusionIntegrating AI agents with real-time enterprise data is no longer optional—it’s essential for business agility and competitive advantage. Deepti Srivastava’s insights and Snow Leopard AI’s platform provide a roadmap for enterprises to connect AI effectively, automate complex workflows, and unlock new value from existing systems.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral
How CEO Concierge is Revolutionizing Virtual Assistant Services for Entrepreneurs: Insights from Jana FranklinIn this episode, host Josh Elledge sits down with Jana Franklin, Founder and CEO of CEO Concierge, to discuss how her company is transforming virtual assistant services for entrepreneurs. Jana shares her personal journey, the challenges she faced as a business owner, and how CEO Concierge helps clients delegate tasks effectively, embrace technology, and maximize productivity. Listeners will gain actionable insights for scaling their businesses while maintaining balance and efficiency.The Power of Personality and Skill MatchingOne of the key differentiators at CEO Concierge is the rigorous approach to matching clients with virtual assistants—not only based on skill but also on personality and work style. Jana explains that understanding a client’s preferences, autonomy, and attention to detail ensures a productive, long-term partnership. A strong personality fit reduces friction, improves communication, and allows VAs to anticipate client needs effectively.Beyond personality, skill alignment is critical to ensure the VA can hit the ground running, whether it’s managing schedules, handling administrative tasks, or mastering specific business tools. CEO Concierge conducts assessments to ensure compatibility between client needs and VA expertise, which enhances efficiency from day one. For entrepreneurs managing multiple stakeholders or teams, this careful matching ensures that all interactions run smoothly and expectations are met consistently.Finally, CEO Concierge invests in ongoing training for both VAs and clients, keeping skills current and adaptable to evolving business needs. From learning new software to mastering AI tools, the company empowers VAs to provide higher-value support while educating clients on delegation strategies. This continuous development ensures that both parties grow together, resulting in stronger partnerships and better business outcomes.About Jana FranklinJana Franklin is a seasoned entrepreneur and franchisee of Fantastic Sams and Jimmy John’s. With years of experience managing multi-location businesses, she understands the importance of delegation, productivity, and leveraging talent to achieve growth. Jana founded CEO Concierge to provide entrepreneurs with a trusted, efficient, and personalized virtual assistant service that addresses real-world business challenges.About CEO ConciergeCEO Concierge is a boutique virtual assistant service that matches business leaders with highly trained VAs from the Philippines. The company emphasizes personality and skill matching, ongoing training, and a concierge-level onboarding experience to ensure every client-VA relationship is a perfect fit. By providing entrepreneurs with trusted support, CEO Concierge allows clients to focus on growth, innovation, and leadership rather than administrative tasks.Links Mentioned in This EpisodeCEO Concierge WebsiteKey Episode HighlightsThe importance of delegating tasks outside your zone of geniusPersonality and skill matching for long-term VA-client successContinuous VA training and client education to enhance efficiencyLeveraging technology and AI tools to maximize productivityOvercoming the founder’s dilemma of letting go to grow your businessCEO Concierge onboarding process ensures the perfect matchConclusionJana Franklin’s insights reveal how a well-matched, well-trained virtual assistant can transform the way entrepreneurs operate. By focusing on personality alignment, skill development, and embracing technology, CEO Concierge empowers clients to delegate with confidence, reclaim their time, and...
Unlocking the Power of Voice AI: Insights from Mohan GulatiVoice technology is transforming the way we interact with digital platforms, making communication more natural, efficient, and human-like. In a recent episode of The Thoughtful Entrepreneur, host Josh Elledge interviewed Mohan Gulati, Founder and CEO of Thinkrr.AI, about his journey and the innovative ways his company is leveraging voice AI. This episode is packed with actionable insights for businesses, entrepreneurs, and tech enthusiasts eager to harness voice technology for growth and efficiency.How Voice AI is Changing Business CommunicationVoice AI is more than just a futuristic concept—it’s a practical tool that can streamline operations and enhance customer experiences. Mohan Gulati highlighted that voice technology allows businesses to handle tasks like inbound calls, appointment scheduling, and lead qualification without constant human intervention. By deploying voice agents, companies can maintain 24/7 availability while reducing operational bottlenecks.Beyond efficiency, voice AI creates a more natural and engaging interaction with customers. Conversational interfaces mimic human speech, conveying nuance, tone, and emotion that text-based communication often lacks. This human-like quality strengthens connections, builds trust, and improves satisfaction in ways traditional methods can’t match.For businesses ready to scale, voice AI offers versatility and easy integration. From small agencies to large enterprises, platforms like Thinkrr.AI allow companies to deploy customized solutions quickly, train voice agents with real customer data, and continuously optimize performance. The result is a seamless, scalable system that enhances both efficiency and customer experience.About Mohan GulatiMohan Gulati is the Founder and CEO of Thinkrr.AI, a company dedicated to making voice technology accessible, intuitive, and effective for businesses of all sizes. With a passion for solving everyday problems through AI, Mohan combines technical expertise with a deep understanding of how businesses can leverage emerging technologies to drive growth.About Thinkrr.AIThinkrr.AI is a voice AI platform that enables businesses to deploy conversational agents on websites, phone systems, and other digital channels. Designed for speed, accuracy, and scalability, Thinkrr.AI helps companies automate routine tasks, improve customer engagement, and expand their service offerings. Its solutions are suitable for businesses, resellers, and entrepreneurs looking to integrate cutting-edge voice technology into their operations.Links Mentioned in this EpisodeThinkrr.AI: https://thinkrr.aiKey Episode HighlightsThe vision behind Thinkrr.AI and the inspiration from real-world challengesHow voice AI enhances efficiency, reduces cognitive load, and creates human-like interactionsPractical applications for businesses, including customer support, appointment booking, and lead qualificationBenefits of voice AI: 24/7 availability, operational efficiency, enhanced customer experience, and scalabilityTips for deploying voice AI: start small, train...
The Art of Authentic Speaking: Lessons from Marianne HickmanIn a world increasingly dominated by automation and AI, genuine human connection is more valuable than ever. In this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Marianne Hickman—speaker coach, top 1% podcaster, and advocate for authentic expression. They explore the power of vulnerability, the nuances of public speaking, and how leading with authenticity can create lasting impact.Rediscovering Authenticity in SpeakingMarianne emphasizes that in a digital world filled with AI-generated content, audiences crave realness. She encourages speakers to show their humanity, share personal passions, and let their creative process shine. Transparency and effort create trust that technology can never replicate.She also addresses the common pitfall of overconfidence, highlighting the Dunning-Kruger effect in the speaking industry. Marianne advises aspiring speakers to seek honest feedback, embrace humility, and focus on substance over style. By prioritizing growth over ego, speakers can steadily develop true expertise.Finally, Marianne underscores the importance of connecting with one person at a time. Real influence comes from seeing your audience as individuals, inviting feedback, and serving others rather than chasing viral moments. This relationship-focused approach is the foundation for a sustainable speaking career.About Marianne HickmanMarianne Hickman is a speaker coach, podcaster, and passionate advocate for authentic communication. She guides aspiring speakers and leaders to find their unique voice, connect with audiences meaningfully, and grow their influence without sacrificing their humanity.About Marianne’s CompanyThrough her coaching and resources, Marianne Hickman helps speakers and professionals cultivate authenticity, confidence, and resilience. She empowers individuals to lead with purpose and build influence that is both impactful and sustainable. Learn more at mariannehickman.com.Links Mentioned in This EpisodeMarianne Hickman Website: mariannehickman.comInstagram: @mariannehickmanKey Episode HighlightsThe value of authenticity in a digital, AI-driven world.Recognizing and overcoming the Dunning-Kruger effect in speaking.How vulnerability builds trust and deep connection with audiences.Practical strategies for coaching and guiding others side by side.Actionable steps for aspiring speakers to grow with integrity and impact.ConclusionBecoming a powerful speaker isn’t about chasing followers or viral fame—it’s about authenticity, humility, and serving others. Marianne Hickman demonstrates that leading with your real voice, walking alongside your audience, and investing in relationships creates influence that lasts.🎧 More from UpMyInfluence🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here » https://go.upmyinfluence.com/leader-intros📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who now land dream guests (and clients)...
How to Transition from 1:1 Coaching to Profitable Group Programs: Insights from Cailen AscherFeeling stuck trading time for money as a coach or consultant? In this episode, Josh Elledge interviews Cailen Ascher, founder of Success Made Simple, to explore how she transitioned from one-on-one coaching to scalable, high-impact group programs. Cailen shares actionable strategies to create transformational group offers, price them for profit, and attract clients ready to invest—all while reclaiming your time and building a business that supports your lifestyle.Why Group Coaching WorksCailen’s shift to group programs was driven by a need for freedom and flexibility as a new mom. One-on-one coaching required constant client calls, leaving little time for family or personal pursuits. By designing group programs, she was able to serve more clients in less time, reclaiming 90% of her schedule while still delivering real results.Group programs also increase income potential without requiring more hours. With a structured curriculum, coaches can generate six- or seven-figure revenue while providing deeper transformation for participants. Peer learning, accountability, and community dynamics make group programs more impactful than individual coaching alone.To make the transition successful, Cailen recommends auditing your current 1:1 work. Identify tasks and content that can be systematized, define the transformation you provide, and design a framework that works for multiple clients simultaneously. Intentional program design is the key to scaling without sacrificing quality or client experience.About Cailen AscherCailen Ascher is a business coach and founder of Success Made Simple. She helps coaches, consultants, and service providers move from time-intensive one-on-one work to profitable group programs, emphasizing efficiency, leverage, and client transformation.About Success Made SimpleSuccess Made Simple is a coaching and training platform dedicated to helping entrepreneurs scale their businesses, streamline their processes, and design programs that generate both income and freedom. The company focuses on actionable strategies, systems, and support to help clients achieve results faster.Links Mentioned in This EpisodeSuccess Made SimpleCailen Ascher LinkedInKey Episode HighlightsHow to transition from 1:1 coaching to group programsDesigning transformational group offers that scalePricing strategies for profit without compromising resultsAttracting high-commitment clients with outcome-driven messagingCreating a business model that supports lifestyle freedomConclusionCailen Ascher’s insights demonstrate that scaling your coaching business doesn’t mean sacrificing quality or client results. By leveraging group programs, coaches can achieve greater impact, increased income, and more personal freedom—all while delivering meaningful transformation to clients.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here » https://go.upmyinfluence.com/leader-intros📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who now land dream guests...
Unlocking Leadership and Decision-Making: Insights from Rick WilliamsIn this episode, Josh Elledge sits down with Rick Williams—keynote speaker, author of Create the Future: Powerful Decision Making Tools for Your Company and Yourself, and experienced board member—to explore actionable strategies for leaders. Rick shares how diverse experiences, effective board governance, and structured decision-making can accelerate organizational success and personal leadership growth.Leadership Lessons and Decision-Making FrameworksRick emphasizes that leadership is a blend of strategy, personal growth, and practical execution. Drawing lessons from sailing and photography, he explains how diverse interests can sharpen decision-making, improve adaptability, and foster creative problem-solving. Leadership skills are not confined to the office; they develop through varied experiences that challenge perspective and enhance judgment.He also highlights the strategic value of a well-structured board of directors. Beyond governance, boards provide accountability, offer new perspectives, and serve as a catalyst for organizational growth. Rick shares best practices for selecting board members, defining clear roles, and maintaining open communication to ensure boards function as true strategic partners.Finally, Rick walks listeners through his five-step decision-making framework: understand the opportunity, define success, explore creative options, assess risks, and make choices aligned with organizational goals and values. By following this structured approach, leaders can navigate complex decisions confidently while aligning their teams and resources toward meaningful outcomes.About Rick WilliamsRick Williams is a physicist-turned-entrepreneur, author, and seasoned board member. His career spans roles in consulting, real estate, and technology leadership, giving him a unique perspective on organizational strategy and decision-making. Rick is passionate about helping leaders create high-impact results through structured processes, personal growth, and strategic board governance.About Rick Williams LeadershipRick Williams Leadership provides insights, tools, and resources for executives and board members to improve decision-making, enhance governance, and accelerate organizational performance. The platform offers thought leadership content, training, and coaching that equips leaders to navigate complex challenges with confidence and clarity.Links Mentioned in this EpisodeRick Williams LeadershipRick Williams LinkedInKey Episode HighlightsDiverse hobbies like sailing and photography can strengthen leadership and decision-making skills.Career evolution shows how different experiences contribute to effective leadership.Boards are strategic assets that add value beyond daily operations.Rick’s five-step decision-making framework helps leaders tackle high-stakes choices.CEOs succeed by orchestrating strategy, delegating tasks, and empowering their teams.ConclusionRick Williams’ insights provide a practical roadmap for leaders who want to make better decisions, leverage boards effectively, and grow personally and professionally. His approach shows that leadership is not just about executing tasks but about cultivating perspective, strategic thinking, and organizational impact.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » a...
Why Writing a Book in 2025 Is a Game-Changer for Entrepreneurs: Expert Insights from Book Coach Jennifer CrosswhiteIn today’s fast-moving business world, standing out as a thought leader requires more than just expertise—it requires authority. In this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Jennifer Crosswhite, seasoned book coach, editor, and CEO and Owner of Tandem Services Inc., to discuss why writing a book in 2025 is one of the most powerful moves an entrepreneur, coach, or CEO can make. Jennifer shares her experience navigating both traditional and self-publishing, revealing actionable strategies for turning your ideas into a book that builds credibility, influence, and lasting impact.Why a Book is Your Ultimate Authority ToolWriting a book in 2025 is not just about putting words on a page—it’s about creating a strategic asset that can transform your business and personal brand. Jennifer emphasizes that a book functions as a tangible symbol of authority, often called a “$10 business card,” and provides a global platform for your message. Beyond credibility, books open doors to speaking engagements, media appearances, consulting opportunities, and strategic partnerships that would otherwise be out of reach.Another important point Jennifer makes is that publishing today is democratized. With self-publishing, hybrid models, and AI tools, entrepreneurs now have unprecedented access to producing high-quality content while directly connecting with their audience. AI can help with research, outlining, and drafting—but the unique voice and expertise of the author remain irreplaceable.Finally, a book is not about filling pages—it’s about transformation. Jennifer stresses the importance of curating ideas, reverse-engineering your content for impact, and keeping your audience’s journey front and center. When done strategically, a book becomes a tool to guide, inspire, and educate readers, creating measurable business growth and influence.About Jennifer CrosswhiteJennifer Crosswhite is a seasoned book coach, editor, and CEO and Owner of Tandem Services Inc., with extensive experience in traditional publishing, self-publishing, and coaching first-time authors. She helps entrepreneurs, thought leaders, and business owners craft books that establish authority, attract opportunities, and create lasting impact for readers and their businesses.About Tandem Services Inc.Tandem Services Inc. is a full-service coaching and publishing company dedicated to guiding authors from concept to published work. From strategic planning and outlining to editing and coaching, Tandem Services empowers business leaders to write books that not only position them as experts but also open doors to new opportunities, audiences, and revenue streams.Links Mentioned in this EpisodeTandem Services Inc. WebsiteJennifer Crosswhite on LinkedInKey Episode HighlightsWhy writing a book is the ultimate authority and credibility builder in 2025.How self-publishing and AI tools are changing the modern publishing landscape.Common misconceptions about book writing: it’s not about page count, it’s about transformation.Jennifer’s two-step brainstorming process: brain dump and organization for maximum impact.The benefits of working with a book coach: accountability, expert feedback, and positioning your book for success.ConclusionWriting a book in 2025 is more than a creative project—it’s a strategic business move that can set you apart, build authority, and expand your reach globally. Jennifer Crosswhite’s...
Transforming Lives and Businesses: The Power of Remote Teams with ZimWorXIn a world where remote work is reshaping the way companies operate, ZimWorX is leading the charge by combining operational excellence with social impact. In a recent episode of The Thoughtful Entrepreneur, host Josh Elledge spoke with JW Oliver, CEO and Co-founder of ZimWorX, about how the company is transforming lives in regions with high unemployment while delivering top-tier remote workforce solutions. This post highlights actionable insights and strategies from their conversation for leaders looking to grow their business and make a meaningful impact.The Mission and Impact of ZimWorXZimWorX operates with a clear mission: “Transforming lives to make a global impact.” JW Oliver shared how the company focuses on creating employment opportunities in countries like Zimbabwe, Zambia, and Costa Rica, where unemployment rates are high and economic opportunity is limited. By giving 51% of profits back to ministries and causes worldwide, ZimWorX has embedded social impact directly into its business model, creating a triple win for team members, clients, and global causes.Remote teams with ZimWorX offer unique advantages that go beyond cost savings. Team members are highly educated, proficient in English, and motivated to excel, ensuring high performance and low attrition. Their time zones align closely with U.S. clients, making collaboration smooth, and their strong work ethic guarantees reliability and dedication. JW emphasizes that the right people in the right roles can transform both business operations and the lives of employees.For companies considering remote teams, ZimWorX provides a straightforward process: discovery calls, interviews with pre-vetted candidates, direct hires, and ongoing support, including HR and workplace wellness programs. By treating team members as integral parts of the organization, businesses can leverage remote teams not only for efficiency but also for sustained growth and positive impact on communities abroad.About JW OliverJW Oliver is the CEO and Co-founder of ZimWorX, a global remote workforce solutions company. With extensive experience in leadership, operational management, and purpose-driven business, JW combines his professional expertise with a personal mission to create jobs, empower individuals, and drive global impact.About ZimWorXZimWorX is a remote workforce solutions provider that specializes in staffing highly skilled professionals in countries such as Zimbabwe, Zambia, and Costa Rica. The company focuses on delivering exceptional talent for industries like healthcare, accounting, executive support, and dental services while prioritizing employee well-being, cultural training, and social impact.Links Mentioned in This EpisodeZimWorXJW Oliver LinkedInKey Episode HighlightsThe ZimWorX mission: profit with purpose and creating jobs in high-unemployment regionsAdvantages of hiring remote teams in Zimbabwe, Zambia, and Costa RicaRoles and industries where remote teams excel, including healthcare, accounting, and executive supportAddressing common concerns: security, time zones, and contract flexibilityStep-by-step onboarding process for remote teamsWorkplace wellness programs that boost engagement and retentionLeadership insights from JW Oliver: adaptability, purpose-driven leadership, and storytellingConclusionJW Oliver’s conversation with Josh Elledge showcases how a business can balance profit, purpose, and people to create meaningful impact. ZimWorX proves that remote teams can do more...
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Comments (3)

District 7 Toastmasters

Jennifer was wonderful and friendly when interviewing District Seven Toastmasters for The Thoughtful Entrepreneur. This was the first time I had been on a podcast, and she made me feel very at ease.It was a great way to be able to talk about what Toastmasters is and our Spring Conference. It was a wonderful experience, especially right after going through the Podcast Guest Mini-Mastery Course.

Jun 2nd
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Josh

Thank you SO much for listening to our show!! 🤓. You are welcome to check out our other UpMyInfluence podcast, Authority Confidential https://bit.ly/2U5xMol and Josh’s other podcast, The SavingsAngel Show https://bit.ly/2tBe4oR

Feb 25th
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Carrie Caulfield Arick

Love this show!

Jun 30th
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