The Thoughtful Entrepreneur
byJosh Elledge · UpMyInfluence.com & PodVerified.com
BusinessEntrepreneurshipManagementMarketing
The Thoughtful Entrepreneur features candid, commercial-free conversations with the founders, CEOs, and B2B leaders building the companies and ideas shaping their industries. Each episode runs 15-25 minutes, built for busy professionals who want substance without the filler. Guests include agency owners, consultants, coaches, and executives with real stories, hard-won lessons, and specific insight for business leaders focused on growth. Host Josh Elledge has conducted 3,000+ interviews, helped launch 300+ podcasts, and has been directly involved in generating $40M+ in client results through relationship-driven media. He knows what makes a guest worth featuring and what makes an appearance actually worth the guest's...
Episodes(40 episodes)
2376 - Safety Tips for Biking and Marketing in Inclement Weather with Andigo's Andrew Schulkind
Aligning Mission and Marketing: Strategic Insights from Andrew Schulkind of AndigoIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Andrew Schulkind, the Digital Strategist and Web Developer behind Andigo. Their conversation explored the critical intersection of high-level digital strategy and mission-driven business growth. Andrew shares how organizations—particularly B Corps and public benefit corporations—can bridge the gap between their core purpose and their marketing execution. This episode serves as a masterclass for leaders looking to move beyond tactical "noise" to build an authentic, long-term digital presence that reflects their true...
Published: Mar 5, 2026Duration: 17m 1s
2375 - How Leaders Can Create Connection and Joy in the Workplace with Amy Leneker
Cultivating Joy: Leading with Less Stress and More Connection with Amy LenekerIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Amy Leneker, Founder and CEO of Amy Leneker, to discuss the urgent need for a shift in workplace culture. As a leadership consultant and author of the book Cheers to Monday, Amy brings a wealth of knowledge on how to dismantle the staggering human and financial costs of workplace stress. Their conversation dives into the "crisis of connection" facing modern teams and provides a roadmap for leaders who want to...
Published: Mar 4, 2026Duration: 17m 40s
2374 - The Canadian Email Marketing Playbook for Compliance and Engagement with Cyberimpact's Geoffrey Blanc
Navigating the Digital Shift: Maximizing Engagement and Delivery with Geoffrey BlancIn a world where digital communication is the heartbeat of business growth, the challenge for modern entrepreneurs is no longer just sending a message—it’s ensuring that message resonates and actually arrives. In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Geoffrey Blanc, the General Manager of Cyberimpact, to discuss the evolving landscape of email marketing and Canadian anti-spam legislation (CASL). Their conversation dives deep into the strategic necessity of choosing platform partners that prioritize compliance and deliverability, particularly for...
Published: Mar 3, 2026Duration: 17m 1s
2373 - Unlocking Talent and the Magic Behind Successful Recruiting with Magic Talent Solutions' Robert Howard
Navigating Talent Optimization: Strategic Staffing and Leadership with Robert HowardIn this episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge speaks with Robert Howard, Director of Recruiting Operations and Executive Leadership Coach at Magic Talent Solutions, about the evolving complexities of the modern workforce. As a military veteran and seasoned business owner, Robert brings a unique perspective to the high-stakes world of recruitment, offering deep dives into bridging staffing gaps and upskilling internal teams. This conversation serves as a strategic guide for founders and executives who are navigating the post-pandemic market correction and seeking to balance...
Published: Mar 2, 2026Duration: 15m 5s
2372 - Quilting Your Way to Business Success and Stitching Together Joy and Achievement with Everyday Effectiveness' Gwen Bortner
Building the Business You Really Want: Strategic Alignment and Intentional Success with Gwen BortnerIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Gwen Bortner, the founder of Everyday Effectiveness, to explore the vital intersection of business strategy and personal fulfillment. With a career spanning over four decades and 47 different industries, Gwen brings a master-level perspective to organizational design and leadership accountability. Their conversation serves as a roadmap for entrepreneurs—particularly women leaders—who find themselves achieving traditional milestones of "success" yet feeling disconnected from the joy and purpose that originally spar...
Published: Mar 1, 2026Duration: 17m 36s
2371 - Networking Beyond Followers and Creating Value Through Meaningful Relationships with Ultimate Networking's George Dubec
Mastering the Human Connection: Networking Secrets from George DubecIn this episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sits down with George Dubec, the founder of Ultimate Networking and a man widely recognized as "The Ultimate Networker." George shares his transformative journey from being a high-level athlete to a business leader who realized, later in life, that his greatest asset wasn't his technical skill, but the depth of his relationships. This conversation dives deep into the tactical and philosophical shifts required to move from transactional "business card swapping" to becoming a high-value resource center. Whether...
Published: Feb 28, 2026Duration: 17m 16s
2370 - Why Building a Business Is Like Racing and How to Avoid Crashing with Beta Ventures' Ike Eze
Unlocking Entrepreneurial Success: Achieving Strategic Alignment with Ike EzeIn this episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sits down with Ike Eze, the Managing Partner at Beta Ventures and author of The Founder Fit: Finding the Business That's Right For You. They explore Ike’s journey from mechanical engineering into the high-stakes world of venture capital, specifically focusing on the booming startup ecosystem in Africa. This conversation provides a masterclass for founders and investors alike, emphasizing that while a great idea is a start, long-term success is ultimately determined by the deep alignment between a...
Published: Feb 27, 2026Duration: 17m 26s
2369 - Practical Steps for Leaders to Foster Engagement and Connection with HEARTnomics' Hanna Bauer
Leading with Heart: Transforming Organizational Culture through Alignment and TrustIn a world where organizational trust is at an all-time low and executive burnout has become the silent epidemic of the boardroom, the need for heart-centered leadership is no longer a "soft" luxury—it is a strategic necessity. In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Hanna Bauer, the Founder and CEO of heartnomics, to discuss a revolutionary approach to professional excellence. Drawing from her harrowing personal journey of surviving terminal heart disease through a pioneering medical procedure, Hanna offers a...
Published: Feb 26, 2026Duration: 20m 48s
2368 -Avoiding Design Disasters in Product Development with Deeney Enterprises' Dianna Deeney
Navigating Innovation: How to Pierce the "Design Fog" with Dianna DeeneyIn the high-stakes arena of product development, the bridge between a brilliant idea and a successful launch is often shrouded in ambiguity. In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Dianna Deeney, the Founder and Consultant at Deeney Enterprises, to discuss her mission of bringing clarity to the creative process. Dianna, the author of Pierce the Design Fog, explores how entrepreneurs and engineering teams often succumb to "solution jumping"—rushing to build before they truly understand the problem. Their co...
Published: Feb 25, 2026Duration: 16m 0s
2367 - Revolutionizing Inspection Processes in Regulated Industries with VirtuSpect's Tim Harris
Revolutionizing Compliance: Modernizing Inspection Workflows with Tim HarrisIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Tim Harris, the Chief Executive Officer of VirtuSpect, to explore how digital transformation is finally reaching the heavily regulated world of physical inspections. Tim shared how VirtuSpect is dismantling the traditional, slow-moving inspection model—particularly in the banking sector—by replacing manual third-party visits with a secure, automated SaaS platform. Their conversation dives into the critical intersection of speed and compliance, revealing how financial institutions and regulated enterprises can close loans faster and reduce oper...
Published: Feb 24, 2026Duration: 14m 51s
2366 -Practical Strategies for Effective Delegation and Engagement with ABC Delegation's Stefan Feuerstein
Mastering the Shift from Micromanagement to Empowerment with Stefan FeuersteinIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Stefan Feuerstein, the founder of ABC Delegation and author of the framework by the same name. Their conversation dives deep into the psychological and structural barriers that prevent leaders from effectively letting go of control. Stefan shares how his methodology helps managers move beyond the "abdication vs. micromanagement" trap, offering a clear system to foster genuine employee engagement and organizational scalability. This episode is an essential guide for any leader feeling overwhelmed...
Published: Feb 23, 2026Duration: 15m 47s
2365 - Enhancing Your Storytelling with Artificial Intelligence While Staying Authentically You with Aleya Harris
Mastering Authentic Storytelling in the Age of AI: Insights from Aleya HarrisIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Aleya Harris, the strategic storytelling consultant and powerhouse founder behind Aleya Harris, to discuss the evolving landscape of brand authority. As artificial intelligence becomes a standard for content creation, Aleya argues that the "human element"—the raw, lived experiences we often hesitate to share—is the only remaining competitive advantage for leaders and speakers. Their conversation explores how to bridge the gap between digital efficiency and emotional resonance, offering a mast...
Published: Feb 22, 2026Duration: 16m 49s
2364 - Rochelle Carrington
2364 - Rochelle Carrington
Published: Feb 21, 2026Duration: 20m 10s
2363 - Maximizing Impact Through Effective Altruism with Amstadd's Claus Geissendoerfer
From Success to Significance: Claus Geissendoerfer on Effective Giving and Purposeful LeadershipIn this episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge speaks with Claus Geissendoerfer, the Director of Programme & Change Management at Amstadd, about the profound shift from professional achievement to personal significance. Claus, an ambassador for the effective altruism movement, shares how his background in high-level change management helped him navigate his own midlife transition toward a life rooted in impact and data-driven philanthropy. Their conversation serves as a masterclass for high-achieving entrepreneurs who find themselves questioning the deeper meaning of their success and...
Published: Feb 20, 2026Duration: 20m 54s
2362 - The Winning Pair That Future-Proofs Your Business with Optimus' Brad Hart
Future-Proofing Leadership: Masterminds and the AI Revolution with Brad HartIn this episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sits down with Brad Hart, the Founder of Optimus, to discuss the critical intersection of high-level peer communities and the rapid advancement of artificial intelligence. Brad, a seasoned entrepreneur who has launched over 25 mastermind groups globally, shares how curated human connection serves as the ultimate safeguard against the isolation and disruption of the digital age. This conversation provides a strategic roadmap for small and medium-sized enterprise (SME) leaders looking to integrate AI into their operations while...
Published: Feb 19, 2026Duration: 21m 2s
2361 - Proven Strategies That Transform Businesses with ProfitX's Daniel Strohli
Systematizing Growth: Scaling to Eight Figures with Daniel StrohliIn this episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge speaks with Daniel Strohli, the Founder of ProfitsX, about the specialized strategies required to bridge the gap between mid-sized success and massive scale. Daniel shares his expertise in helping companies in the $5M to $15M revenue range move beyond scattered, founder-dependent operations and into the world of repeatable, process-driven machines. This conversation offers a deep dive into the "connective tissue" of business—the processes that empower people and products to perform at their peak—while providing a mast...
Published: Feb 18, 2026Duration: 15m 18s
2360 - The Doctor’s Playbook for Standing Out in Today’s Healthcare Market with GrassRoots Medical Marketing's Laura Woodard
Revitalizing Private Practice: Strategic Medical Marketing with Laura WoodardIn this episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge speaks with Laura Woodard, the Founder of Grass Roots Medical Marketing, about the intensifying pressures facing independent physicians today. With corporate consolidation and administrative burdens causing an exodus of private practitioners, Laura shares her thirty years of expertise to help doctors reclaim their local authority and compete effectively with hospital-owned entities. This conversation provides a high-level roadmap for healthcare providers to bridge the gap between their clinical excellence and their digital presence, ensuring they can reach the...
Published: Feb 17, 2026Duration: 19m 29s
2359 - A Deep Dive into Merchant Services with JELA Payments' Jimmy Estrada
Human-Centric Merchant Services: Optimizing Payment Systems with Jimmy EstradaIn this episode ofThe Thoughtful Entrepreneur Podcast, host Josh Elledge sits down with Jimmy Estrada, the Founder and Owner ofJELA Payments Systems, to demystify the complex world of merchant services. Jimmy shares how his firm bridges the gap between massive, faceless payment processors and the independent business owners who often find themselves stranded when technical glitches or funding holds arise. This conversation offers a strategic look at how a high-touch, consultative approach to payment systems can help B2B firms and retailers reclaim their profit margins, mitigate risk...
Published: Feb 16, 2026Duration: 19m 15s
2358 - Enhancing Marketing and Operations Without Losing the Human Touch with Unlucky Umbrella Studio's Kasandra Murray
Bridging the Gap: Integrating Marketing and Operations for Scalable Growth with Kasandra MurrayIn this episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sits down with Kasandra Murray, the Founder and Owner of Unlucky Umbrella Studio, to discuss the critical intersection of lead generation and operational fulfillment. Kasandra shares her expertise on why even the most aggressive marketing campaigns are doomed to fail if a business lacks the back-end systems to support an influx of new interest. This conversation provides a strategic roadmap for entrepreneurs who are tired of "leaky buckets" in their sales funnels and...
Published: Feb 15, 2026Duration: 16m 15s
2357 - How Passion Fuels Business Innovation with Smartfinds Internet Marketing's Melih Oztalay
Future-Proofing B2B Marketing: AI, Omnichannel Strategies, and Decades of Wisdom with Melih OztalayIn this episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sits down with Melih Oztalay, the CEO of SmartFinds Marketing, to explore the seismic shifts currently reshaping the B2B landscape. With a marketing career spanning back to 1987, Melih offers a rare perspective on how to bridge the gap between traditional advertising principles and the hyper-accelerated world of AI-driven engagement. This conversation serves as a strategic roadmap for leaders looking to move beyond single-channel tactics and embrace a holistic, 360-degree approach that...
Published: Feb 14, 2026Duration: 21m 56s