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)
2396 - A New Approach to Recruitment for Veterans and Employers with Red Balloon's Andrew Crapuchettes
Building a Values-Driven Workforce: Strategic Hiring Insights with Andrew CrapuchettesIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Andrew Crapuchettes, CEO of RedBalloon and owner of MilitaryHire.com, to tackle one of the most significant pain points for modern business owners: the talent crisis. As the labor market becomes increasingly fragmented by shifting cultural expectations and automated screening tools, Andrew shares a contrarian approach to recruiting that prioritizes merit, work ethic, and cultural alignment over mere technical keywords. Their conversation offers a strategic roadmap for employers looking to move beyond "...
Published: Mar 25, 2026Duration: 23m 4s
2395 - Leo Young
2395 - Leo Young
Published: Mar 24, 2026Duration: 16m 38s
2394 - Jared T. Ross
2394 - Jared T. Ross
Published: Mar 23, 2026Duration: 21m 42s
2393 - Ron Netanel
2393 - Ron Netanel
Published: Mar 22, 2026Duration: 20m 50s
2392 - Ohad Shaked
2392 - Ohad Shaked
Published: Mar 21, 2026Duration: 18m 3s
2391 - Serge Kuznetsov
2391 - Serge Kuznetsov
Published: Mar 20, 2026Duration: 20m 7s
2390 - Omer Gotlieb
2390 - Omer Gotlieb
Published: Mar 19, 2026Duration: 18m 20s
2389 - Putting the Human Side Back into Management with Manager Method’s Ashley Herd
The Manager Method: Practical, Human-Centered Leadership for a Changing WorkplaceIn a world where technology and AI are transforming the workplace at breakneck speed, the fundamentals of great leadership remain rooted in human connection and intentional action. In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Ashley Herd, the Founder and CEO of Manager Method, to explore the core of effective management. Drawing on her diverse background in legal and HR leadership at organizations like McKinsey, Ashley shares how to move beyond abstract theory into actionable behaviors. This conversation provides a...
Published: Mar 18, 2026Duration: 22m 34s
2388 - The Playbook for a Winning Team Culture with BH Consultancy’s Bobby Humes
Mastering the Human Side of Leadership: Lessons in Agility with Bobby HumesIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Bobby Humes, Lead Consultant & CEO of BH Consultancy, to discuss the shifting paradigms of modern management. Bobby, widely known as "Coach Bobby," brings a unique perspective to the table, blending his high-level executive experience with lessons learned from coaching youth basketball. Their conversation explores the vital transition from technical expertise to people-centric leadership, the necessity of documenting institutional knowledge in a post-"Great Resignation" world, and how thoughtful leaders can...
Published: Mar 17, 2026Duration: 17m 17s
2387 - Why the Toughest Challenges Can Lead to Purpose-Driven Success with Patrick Mork
Building Purpose-Driven Companies: Leadership Wisdom with Patrick MorkIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Patrick Mork, a renowned leadership speaker, executive advisor, and author of Step Back and Leap: Nine Keys to Unlock Your Life and Make Change Happen. Drawing from his high-octane background as a tech founder and a three-time Chief Marketing Officer, Patrick shares how the modern leadership landscape requires more than just technical acumen—it demands a foundation of purpose. This conversation explores the psychological and operational hurdles of the startup journey, providing a strategic ro...
Published: Mar 16, 2026Duration: 20m 36s
2386 - Stirring Corporate Talent into Nonprofit Board Service with Cause Strategy Partners’ Whitley Richards
Empowering Professionals and Corporate Culture Through Nonprofit Board Service: Insights from Whitley RichardsIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Whitley Richards, the CEO of Cause Strategy Partners, to explore the high-impact intersection of corporate talent and social good. Their conversation highlights how nonprofit board service is no longer just an act of charity; it is a strategic vehicle for leadership development and corporate social responsibility (CSR). Whitley explains how her organization bridges the gap between major corporations and the nonprofit sector, ensuring that professionals from companies like Google...
Published: Mar 15, 2026Duration: 15m 37s
2385 - Finding Balance Between Tactical Hobbies and Business Growth with CJAM's Behdad Jamshidi
Navigating the Marketing Agency Maze: Strategic Matchmaking with Behdad JamshidiIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Behdad Jamshidi, the Founder & CEO of CJAM Marketing, to discuss the critical challenges business leaders face when trying to scale their marketing efforts. With over 160,000 agencies in the market, founders often find themselves trapped in a cycle of "agency hopping" that drains resources and kills momentum. Their conversation dives into the necessity of strategic matchmaking, the value of intentional leadership, and how to find the less than 5% of agencies that actually align...
Published: Mar 14, 2026Duration: 26m 3s
2384 - Empowering Entrepreneurs Everywhere Through Democratized Business Education with BOS-UP's Scott Abbott
Mastering Business Scalability: Scott Abbott on Fusing AI, Systems, and Human GrowthIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Scott Abbott, the serial entrepreneur, investor, and Founder & CEO of BOS-UP. The conversation explored the critical intersection of modern technology and timeless business principles, focusing on how Scott’s "Boss Up" framework helps startups and mid-market companies scale effectively. By integrating AI-driven insights with high-level coaching and human-centered development, Scott provides a roadmap for leaders who want to move beyond mere "hustle" and toward a structured, engineering-minded approach to growth. Th...
Published: Mar 13, 2026Duration: 17m 54s
2383 - Lisa Sharapata
2383 - Lisa Sharapata
Published: Mar 12, 2026Duration: 18m 59s
2382 - Wyatt Kirby
2382 - Wyatt Kirby
Published: Mar 11, 2026Duration: 16m 28s
2381 - Boosting Advertising Performance Through AI with Plurio’s Seva Ustinov
Revolutionizing Digital Advertising: Strategic Insights into AI-Driven Campaign Management with Seva UstinovIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Seva Ustinov, the Founder and CEO of plurio, to discuss the seismic shift occurring within the digital advertising landscape. As managing ad spend across Google, Meta, and TikTok becomes increasingly fragmented and complex, Seva shares how autonomous AI agents are moving beyond simple data reporting to active execution. This conversation provides a masterclass for high-growth founders and marketing executives who are looking to bridge the gap between surface-level platform metrics...
Published: Mar 10, 2026Duration: 15m 52s
2380 - Smart Tax Strategies for Business Owners Using Trusts with Sally Gimon
Unlocking Advanced Tax Savings: How Strategic Trusts Empower Entrepreneurs with Sally GimonIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Sally Gimon, a dedicated Investor and tax strategist at The Trust is You, to dismantle the common frustrations business owners face during tax season. Despite having experienced CPAs, many entrepreneurs find themselves blindsided by massive tax bills—a pain point Sally knows intimately from her own early days in real estate. Their conversation dives into the specialized world of non-grantor irrevocable spendthrift trusts, a legal framework used by America’s weal...
Published: Mar 9, 2026Duration: 16m 43s
2379 - Stacey Bailey
2379 - Stacey Bailey
Published: Mar 8, 2026Duration: 14m 45s
2378 - Carl Manlan
2378 - Carl Manlan
Published: Mar 7, 2026Duration: 18m 53s
2377 - The Transformative Power of Asking and Listening with Empathy with Lushin's Shad Tidler
Mastering the Human Element of Sales and Leadership with Shad TidlerIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Shad Tidler, a senior consultant and coach specializing in Sales and Leadership/Management at Lushin. The conversation dived deep into the psychological barriers that often prevent talented entrepreneurs from scaling their sales organizations and leading with true impact. Shad’s expertise lies in dismantling the "head trash" that complicates the sales process, helping leaders transition from a state of reactive management to one of proactive, high-performance coaching. For any founder feeling st...
Published: Mar 6, 2026Duration: 19m 0s