The Thoughtful Entrepreneur

Josh Elledge of UpMyInfluence.com

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/

  1. 16시간 전

    2332 - What Swimming Teaches About Direct Mail Success with Zairmail's Wilson Zehr

    The Enduring Power of Direct Mail: Expert Insights from Zairmail’s Wilson ZehrIn this episode of The Thoughtful Entrepreneur, host Josh Elledge welcomes Wilson Zehr, Founder and CEO of Zairmail, for a deep exploration into why direct mail is still one of the most effective marketing channels in today’s digital-first world. Wilson draws from decades of experience—plus a surprising connection to competitive swimming—to illustrate how businesses can blend digital convenience with physical mail for unmatched engagement and ROI. This episode offers a practical, insightful guide for any leader looking to leverage direct mail to scale their business. Direct Mail as a Competitive Advantage in a Digital EraWilson opens the conversation by comparing the discipline of competitive swimming to the discipline required to launch successful marketing campaigns. New swimmers must warm up, refine their technique, and focus on continuous improvement—principles that apply seamlessly to businesses exploring direct mail for the first time. He emphasizes the importance of starting with small, targeted campaigns and refining strategy over time. The discussion then highlights how Zairmail’s platform blends the ease of digital workflows with the impact of physical mail. Businesses can upload documents, preview their mail in real time, and send campaigns with a single click. With next-day processing and a nationwide production network, Zairmail ensures speed, scalability, and reliability across every campaign. Wilson also breaks down why direct mail continues to outperform expectations in 2024. From owning the “mail moment” to delivering strong ROI and enabling precise demographic targeting, physical mail creates a level of attention and trust that digital ads struggle to achieve. Whether using postcards, letters, snap packs, or self-mailers, choosing the right format can dramatically improve response rates and engagement. About Wilson ZehrWilson Zehr is the Founder and CEO of Zairmail and a seasoned marketing expert with 26+ years of experience helping organizations execute high-impact direct mail campaigns. Wilson’s background in both technology and traditional media uniquely positions him to bridge the gap between digital tools and physical marketing performance. Connect with Wilson on LinkedIn. About ZairmailZairmail is a leading direct mail platform that makes sending physical mail as simple as sending an email. With next-day processing, nationwide facilities, real-time previews, and data-driven targeting tools, Zairmail empowers businesses of all sizes to launch fast, reliable, and high-ROI direct mail campaigns. Links Mentioned in This EpisodeZairmail WebsiteWilson Zehr LinkedIn Profile Key Episode Highlights:How swimming principles translate into better marketing executionWhy direct mail continues to deliver high ROI in 2024The four main direct mail formats and when to use eachHow Zairmail blends digital workflows with physical mail for unmatched efficiencyExpert tips on targeting, creative, testing, and integrating digital channels ConclusionWilson Zehr reinforces that direct mail isn’t outdated—it’s a powerful, underutilized differentiator. By integrating digital...

    18분
  2. 1일 전

    2331 - The Essential Guide to Understanding Your Nervous System and Enhancing Performance with Sondera's Kristen Boss

    Mastering Stress and Nervous System Regulation for High Performance: Insights from Kristen BossIn this episode of The Thoughtful Entrepreneur, host Josh Elledge welcomes Kristen Boss, Founder of Sondera, executive coach, keynote speaker, and host of The Kristen Boss Podcast. Kristen dives deep into the power of nervous system regulation, helping high achievers and leaders understand how to perform sustainably under pressure. Her approach bridges neuroscience, leadership, and emotional intelligence—offering strategies that empower professionals to thrive without burning out. How Nervous System Intelligence Fuels Resilient LeadershipKristen opens by revealing how intentional stillness, creativity, and mindful hobbies—like skiing or crafting—help her stay grounded. These moments of calm, she explains, are not indulgences but essential tools for recovery and innovation. High achievers often push through stress, but learning to slow down can enhance clarity and unlock creativity. She also introduces the concept of stress types—fight, flight, and freeze—explaining how each reflects an automatic safety response that shapes our behavior in business and leadership. Recognizing these patterns allows leaders to manage reactivity, strengthen decision-making, and create more emotionally intelligent teams. Throughout the conversation, Kristen emphasizes that sustainable high performance isn’t about pushing harder—it’s about learning to regulate your internal state. By calming your nervous system, you unlock greater focus, empathy, and resilience, enabling you to lead with intention rather than impulse. About Kristen BossKristen Boss is an executive coach, keynote speaker, and Founder of Sondera. A sought-after thought leader on high performance and nervous system intelligence, Kristen has built a global brand helping professionals and entrepreneurs master sustainable success. She is also the host of The Kristen Boss Podcast, where she explores leadership, mindset, and emotional resilience. Connect with Kristen on LinkedIn. About SonderaSondera is dedicated to helping leaders, teams, and organizations integrate nervous system intelligence into their approach to business and life. Through coaching, programs, and training, Sondera equips high achievers with the tools to perform at their best—without sacrificing wellbeing or fulfillment. Links Mentioned in This EpisodeSondera WensiteKristen Boss on LinkedIn Key Episode Highlights:Why intentional stillness enhances creativity and performanceHow to identify your unique stress type (fight, flight, or freeze)Practical regulation tools—breathwork, micro-pauses, and reflectionThe role of empathy and curiosity in effective leadershipWhy nervous system intelligence is the foundation of sustainable growth ConclusionKristen Boss reminds us that in a world obsessed with doing more, the real edge lies in being regulated, present, and self-aware. Nervous system intelligence isn’t just a wellness trend—it’s a leadership essential. By mastering emotional balance and responding rather than reacting, leaders can build trust, inspire teams, and sustain success in the long run. 🎧...

    21분
  3. 2일 전

    2330 - Key Insights for Building High-Performing Organizations with Ninety's Mark Abbott

    Mastering Business Growth: Insights from Mark Abbott, Founder & CEO of Ninety, on Operating Systems, Culture, and Organizational MaturityIn this episode, host Josh Elledge sits down with Mark Abbott, Founder and CEO of Ninety, for a deep dive into business operating systems, organizational culture, and the journey of scaling small and mid-sized companies. Mark—drawing on decades of experience in entrepreneurship, software development, coaching, and workplace culture—explains how leaders can build high-performing, resilient organizations by implementing the right frameworks at the right time. This blog breaks down the episode’s key insights and practical guidance to help business owners navigate their company’s growth stages with clarity and confidence. Building Mature, Aligned, and High-Trust OrganizationsMark begins by explaining what a Business Operating System (BOS) truly is: a combination of tools, disciplines, and concepts that help organizations stay aligned, accountable, and scalable. He emphasizes that every company already has an operating system—whether intentional or accidental—and the goal is to consciously design one that matches the business’s stage of development. Popular frameworks like EOS, Scaling Up, and The Great Game of Business offer structured paths, but each company must adopt the tools most appropriate for their maturity level. He breaks down the five stages of business development—Formation, Early Growth, Expansion, Maturity, and Legacy—and stresses that leaders must avoid skipping steps. For example, documenting every process too early is counterproductive; focusing instead on clarity, roles, and early team alignment yields better results. As businesses grow, they often mistake size for maturity, creating organizations that look impressive on the outside but lack foundational discipline internally. Mark also highlights the importance of culture, trust, and forgiveness. High-performance organizations assume goodwill, set clear expectations, and use trust as a guiding principle—while also acknowledging that not all behaviors should be tolerated. He references research from Dr. Paul Zak to explain how trust chemically fuels team performance and why leaders must foster environments where transparency and accountability thrive. Platforms like Ninety help reinforce these practices by providing tools for meetings, scorecards, vision alignment, and process documentation, ensuring companies build habits that support long-term excellence. About Mark AbbottMark Abbott is the Founder and CEO of Ninety, a platform designed to help small and mid-sized businesses implement and sustain business operating systems. With decades of experience across entrepreneurship, leadership development, and organizational design, Mark has coached countless teams on building trust-based cultures and operational excellence. Connect with Mark on LinkedIn. About NinetyNinety is a comprehensive software platform built to help organizations adopt, implement, and sustain a Business Operating System such as EOS. With tools for meetings, scorecards, rocks, issues, processes, and organizational clarity, Ninety equips leadership teams with everything they need to run a healthy, aligned, and scalable business. The platform supports both coach-led and self-directed implementations and includes extensive resources for long-term growth and accountability. Links Mentioned in This EpisodeMark Abbott LinkedIna...

    19분
  4. 3일 전

    2329 - How to Communicate Worth in Your SaaS Pricing Using the Value Equation with Product Tranquility's Dan Balcauski

    Mastering B2B SaaS Pricing: Expert Strategies from Dan Balcauski of Product TranquilityIn this episode, host Josh Elledge sits down with Dan Balcauski, Founder and Principal Consultant of Product Tranquility, to uncover the true science behind effective B2B SaaS pricing. With over two decades in software and deep expertise in pricing strategy, Dan explains why pricing is often misunderstood, what founders consistently overlook, and how SaaS leaders can turn pricing from a liability into a powerful growth lever. This blog breaks down the episode’s most actionable insights to help SaaS founders and product leaders build value-driven, scalable pricing systems. Why Most SaaS Pricing Fails—and What to Do InsteadDan explains that the biggest mistake in SaaS pricing is choosing numbers before validating whether customers actually perceive value. Founders often rush to set a price—$49, $99, $1,000—without first understanding the customer’s pain, alternatives, or what makes the product meaningfully different. Instead, Dan recommends charging something early, engaging customers in honest conversations about value, and validating willingness to pay through real-world interactions rather than internal assumptions. He emphasizes that pricing is ultimately about value, not features. Early-stage founders frequently offer too much for too little, or price too high without proving outcomes. Avoiding these pitfalls requires asking the right questions, initiating value conversations early, and documenting everything customers say about cost, alternatives, and perceived ROI. Dan also stresses the importance of selecting a pricing model that aligns with how the customer receives value. Whether subscription-based, usage-based, or outcome-based, the model must match customer expectations and internal economics. This approach helps avoid unnecessary friction in the buying process while increasing expansion potential over time. About Dan BalcauskiDan Balcauski is the Founder and Principal Consultant of Product Tranquility, where he helps B2B SaaS companies build value-based pricing and packaging strategies. With over 20 years of experience in product management and pricing, Dan works with SaaS CEOs and product leaders to align pricing with customer value and business goals. Connect with Dan on LinkedIn. About Product TranquilityProduct Tranquility is a boutique consulting firm specializing in pricing, packaging, and product strategy for B2B SaaS companies. Through proven frameworks and deep market analysis, Product Tranquility helps SaaS founders create pricing systems that accelerate revenue, improve customer alignment, and scale sustainably across growth stages. Links Mentioned in This EpisodeDan Balcauski LinkedInProduct Tranquility Website Key Episode HighlightsPricing must begin with validating customer value—not picking numbersWhy charging something early leads to stronger product feedbackHow to start pricing conversations earlier in the customer journeyChoosing the right pricing model based on value deliveryWhy packaging and tiered pricing increase conversionsHow to use the Van Westendorp Price Sensitivity MeterCommon pricing pitfalls (anchoring too low, freemium overuse, feature-based pricing)Why pricing is an iterative, evolving process—not a one-time...

    28분
  5. 4일 전

    2328 - Overcoming Skepticism in Hiring Senior Talent Overseas with Rekruuto's Sid Jashnani

    Unlocking Global Talent and Founder Freedom: Insights from Sid Jashnani of RekruutoIn this episode, host Josh Elledge talks with Sid Jashnani, Founder of Rekruuto and certified EOS implementer, about how founders can reclaim their time, scale with confidence, and access high-performing global talent. Sid shares his personal leadership journey, his frameworks for effective delegation, and his expert perspective on hiring senior-level overseas professionals—revealing practical, repeatable systems founders can apply immediately. The Power of Global Hiring and Delegation for FoundersSid’s story begins on the golf course with his 14-year-old son during a period of serious illness—an experience that reshaped how he leads both at home and in business. Instead of defaulting to advice or correction, Sid embraced curiosity, asking open-ended questions that encouraged deeper connection. This same leadership principle applies directly to business: when founders listen more and prescribe less, teams become empowered, engaged, and more accountable. Sid also challenges the common belief that overseas hiring should be limited to entry-level roles. Drawing from his experience in the Philippines, he explains why many mid- and senior-level professionals abroad bring global expertise, strong process orientation, and cultural adaptability—making them strong fits for operations, marketing, finance, and management roles within EOS-driven companies. With proper onboarding and context-sharing, these hires integrate seamlessly and provide exceptional value at a fraction of the cost. To help founders free themselves from burnout and low-value tasks, Sid offers his four-quadrant time audit: a simple but powerful system for categorizing activities based on skill and enjoyment. By identifying tasks you are good at but dislike—or those you neither enjoy nor do well—leaders can delegate strategically, reinvesting their energy into high-impact work that drives revenue, growth, and clarity. About Sid JashnaniSid Jashnani is the Founder of Rekruuto, a global hiring agency specializing in matching U.S. companies with senior-level talent from overseas. As a certified EOS implementer and seasoned entrepreneur, Sid helps founders streamline their operations, delegate effectively, and scale sustainably. Connect with Sid on LinkedIn. About RekruutoRekruuto helps founders and business owners hire skilled global talent through a risk-free, flexible model. Specializing in mid-level and senior overseas professionals—particularly from the Philippines—Rekruuto provides vetted candidates, trial periods, and month-to-month engagement options. Their mission is to help founders reclaim their time by delegating confidently and scaling with the right people in the right seats. Links Mentioned in This EpisodeSid Jashnani LinkedIn ProfileRekruuto website Key Episode HighlightsWhy curiosity-based leadership strengthens both family and team relationshipsThe advantages of hiring mid- to senior-level overseas talentCultural adaptability and global experience of Filipino professionalsSid’s four-quadrant time audit for identifying delegation opportunitiesHow to calculate the value of your time as a founderRekruuto’s risk-free hiring model and month-to-month flexibilityHow to start small and scale confidently with global...

    20분
  6. 5일 전

    2327 - Elevate Your Business Performance through Nearshoring and AI with WorkBetterNow's Rob Levin

    Unlocking the Power of Nearshore Talent: Insights from Rob Levin of WorkBetterNowIn this episode, host Josh Elledge talks with Rob Levin, Chairman and Co-Founder of WorkBetterNow, about how nearshore talent is transforming the way small and mid-sized businesses scale and strengthen their teams. Rob—also the host of the Great Talent Great Business podcast and author of the forthcoming New Talent Playbook—explains why nearshoring offers a competitive advantage and how companies can use it to build high-performing, culture-aligned teams. Why Nearshore Talent Is Transforming the Modern WorkforceRob explains that U.S. companies continue to battle a persistent talent shortage, rising salaries, and intense competition for high-performing professionals. Nearshoring solves these challenges by giving leaders access to highly skilled, English-proficient team members across Latin America who work in real time, align culturally, and bring strong loyalty and work ethic. He shares examples of how roles such as executive assistants, estimating support, inside sales, marketing, finance, and customer service can dramatically increase organizational capacity. When leaders delegate operational tasks to nearshore professionals, they free themselves to focus on strategy, revenue, and growth. WorkBetterNow further strengthens this advantage by training all talent in AI, boosting efficiency, accuracy, and innovation. Rob also highlights how nearshoring simplifies HR for business owners. WorkBetterNow handles payroll, compliance, and all employment-related responsibilities, eliminating legal risk and administrative burden. Companies see the best results when they treat nearshore professionals as integrated team members—with clear expectations, cultural inclusion, and strong communication rhythms. About Rob LevinRob Levin is the Chairman and Co-Founder of WorkBetterNow and a respected authority on hiring, talent strategy, and small business growth. As host of the Great Talent Great Business podcast and author of The New Talent Playbook, Rob helps leaders build effective, scalable teams with clarity and confidence. Connect with Rob on LinkedIn. About WorkBetterNowWorkBetterNow provides full-time, dedicated nearshore professionals from Latin America to U.S.-based companies. Through its Precision Match Process and rapid onboarding, WorkBetterNow delivers culturally aligned, highly skilled talent while managing all HR, payroll, and compliance. Their mission is to help small and mid-sized businesses scale smarter by integrating exceptional nearshore team members. Links Mentioned in This EpisodeRob Levin’s LinkedIn ProfileWorkBetterNow Website Key Episode HighlightsWhy nearshoring is becoming essential for SMB growthThe top roles where nearshore professionals deliver the most impactHow WorkBetterNow trains its talent in AI for increased productivityThe importance of cultural fit and team integration in remote teamsHow nearshoring reduces hiring risk, compliance pressure, and administrative loadA breakdown of WorkBetterNow’s Precision Match Process ConclusionRob’s insights reveal the growing importance of nearshoring as a long-term workforce strategy. With the right partner and processes in place, leaders can build deeply committed,...

    18분
  7. 6일 전

    2326 - The Power of Stacking Great Weeks for Lasting Impact with 2b Limitless' Mick Todd

    From Chaos to Clarity — How To Be Limitless Helps You Lead with Discipline and ImpactIn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Mick Todd, high-performance coach and Founder of To Be Limitless. Mick shares powerful insights on how to unlock clarity, discipline, and high performance to create lasting success—both personally and professionally. With his background in elite coaching and leadership development, Mick helps entrepreneurs and executives design lives filled with purpose, intentionality, and measurable progress. Stack Great Weeks, Build a Limitless LifeMick Todd believes success doesn’t come from dramatic overhauls—it comes from consistently stacking great weeks. In this episode, he shares how the To Be Limitless method helps leaders move from chaos to clarity through structured weekly execution, self-discipline, and aligned behaviors. His framework is grounded in practical performance science and designed to help people focus on what truly matters. One of Mick’s core philosophies is that clarity drives discipline—and discipline drives results. Through coaching, leadership intensives, and team engagement strategies, To Be Limitless works with clients to improve time ownership, foster accountability, and drive alignment between vision and action. Mick also emphasizes the importance of compliance—not as a restriction, but as a powerful way to stay committed to personal and team goals. Whether you're leading a team or trying to better manage your own energy, Mick’s advice is clear: create structure, define what a "great week" looks like, and repeat. With intention and consistency, you can build a life and business that feel truly limitless. About Mick ToddMick Todd is a globally respected high-performance coach and the Founder of To Be Limitless. He works with leaders, entrepreneurs, and elite teams to cultivate clarity, structure, and intentional living. His mission is to help individuals and organizations unlock their full potential through meaningful discipline and powerful personal development. Connect with Mick on LinkedIn. About 2b Limitless2B Limitless is a high-performance coaching and leadership development firm that helps individuals and teams transform how they think, work, and lead. With a focus on clarity, compliance, and elite execution, the company offers 1:1 coaching, executive retreats, and corporate programs designed to deliver sustainable success. Links Mentioned in This Episode2b Limitless WebsiteMick Todd on LinkedIn Episode HighlightsHow stacking “great weeks” leads to lasting performance and clarityWhy clarity and discipline are the cornerstones of successHow To Be Limitless supports both personal and professional transformationThe role of compliance and structure in driving high performanceStrategies for increasing engagement and alignment within teams ConclusionMick Todd’s approach to high performance is both simple and profound: start with clarity, execute with discipline, and build momentum week after week. Through his work with To Be Limitless, Mick empowers leaders to live and work with greater purpose,...

    19분
  8. 11월 21일

    2325 - Transform Your Relationships and Sales through Ethical Persuasion Techniques with Patrick Van Der Burght

    The Science of Ethical Persuasion — Strategies to Hear “Yes” More Often with Patrick Van Der BurghtIn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Patrick Van Der Burght, SHIELD Certified Coach, Sydney Institute licensed trainer, and founder of Ethical Persuasion. Patrick shares how ethical persuasion—rooted in behavioral science—can drastically improve how you communicate, sell, and lead. He explains why persuasion isn’t about manipulation but about building trust, creating clarity, and helping others say “yes” to what’s right for them. Master the Psychology of Persuasion Without ManipulationPatrick Van Der Burght’s approach begins with reframing what persuasion really is: not trickery, but a science-based method to guide decision-making ethically and effectively. Drawing on the seven universal principles of persuasion—reciprocity, commitment and consistency, social proof, authority, liking, scarcity, and unity—Patrick shares how understanding these can significantly improve conversations, sales, and influence. He emphasizes that persuasion must be built on relationship, clarity, and trust. If those elements are missing, objections arise and conversions stall. From using specific data to build credibility, to helping clients make public commitments that increase follow-through, Patrick lays out actionable, research-backed strategies anyone can use. He also encourages business owners and consultants to stop chasing “more follow-ups” and instead fix the relationship and clarity gaps first. Whether you’re presenting offers, coaching clients, or leading teams, this episode shows how ethical persuasion can lead to stronger relationships, more impact, and consistent results—without pressure or pushiness. About Patrick Van Der BurghtPatrick Van Der Burght is the founder of Ethical Persuasion, a certified SHIELD Coach, licensed Sydney Institute trainer, and author of How to Hear Yes More Often. He teaches entrepreneurs, consultants, educators, and teams how to ethically apply behavioral science to become more persuasive, trusted, and effective communicators. Connect with Patrick on LinkedIn. About Ethical PersuasionEthical Persuasion offers practical, science-based training and resources to help business owners, consultants, and professionals master the art of influence with integrity. From free tools and workshops to in-depth coaching and educational programs, the company equips leaders with the skills to ethically inspire action and build trust. Links Mentioned in This EpisodeEthical Persuasion WebsitePatrick Van Der Burght on LinkedIn Key Episode HighlightsWhy ethical persuasion is more effective than traditional “sales tactics”The 7 universal persuasion principles every business leader should knowHow trust, clarity, and relationship reduce objections and increase conversionsHow to apply commitment, social proof, and loss aversion effectivelyWays to build goodwill with genuine value before making an offer ConclusionPatrick Van Der Burght proves that the most persuasive people aren’t pushy—they’re precise. By understanding the psychology of influence and applying it...

    28분
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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/