EP.41 - Why Entrepreneurship Feels So Lonely (And How to Fix It)

EP.41 - Why Entrepreneurship Feels So Lonely (And How to Fix It)

In this episode of Inside the 90, Jami and Andrew discuss the often-overlooked reality of entrepreneurship: loneliness and the critical need for intentional community. Andrew shares his journey of relocating from Michigan to Greenville, SC, rebuilding his business network from scratch, and discovering how empathy, accountability, and growth-focused relationships are essential for visionary leaders. The conversation explores co-working spaces, peer groups, networking with purpose, and how meaningful entrepreneurial communities can dramatically impact both business success and personal well-being. Key Topics - Entrepreneurship can feel isolating without intentional community. - Relocating a business and rebuilding relationships from scratch. - The importance of empathy and accountability in leadership. - Why entrepreneurs need to leave the office and engage with others. - Building authentic relationships instead of transactional networking. - The role of co-working spaces in growth and energy. - Peer groups, EOS, and mastermind communities for entrepreneurs. - Balancing vulnerability, business pressure, and personal growth. - How introverts and extroverts approach community differently. - Creating communities that support both giving and receiving. Chapters 00:00 - Introduction to entrepreneurship and loneliness. 02:15 - Andrew’s move from Michigan to Greenville and rebuilding community. 05:40 - Defining the type of entrepreneurial community they wanted. 10:05 - Why entrepreneurs must leave the office to grow. 14:20 - Networking versus authentic relationship building. 19:35 - The value of empathy and accountability groups. 24:10 - How co-working spaces fuel growth and collaboration. 29:50 - Stories of entrepreneurial support and vulnerability. 35:30 - The importance of committing to communities consistently. 41:45 - Breakdown of the groups and communities Andrew participates in. 48:10 - Jami’s leadership, mentorship, and creative communities. 54:20 - Supporting entrepreneurs through giving, not just receiving. 58:10 - Introverts, extroverts, and finding the right community fit. 01:01:30 - Final encouragement to entrepreneurs seeking connection. Mentions & Credits - EOS (Entrepreneurial Operating System) — https://www.eosworldwide.com/ - Flywheel Co-working — https://flywheelcoworking.com/ - Strategic Coach — https://www.strategiccoach.com/ - Grow Forum — https://growforum.io/- C12 Business Forums — https://www.c12forums.com/ - Agency Management Institute — https://agencymanagementinstitute.com/ - Chris Cloud — https://www.linkedin.com/in/chriscloud/ - Benton Woodring — https://www.linkedin.com/in/bentonwoodring/

EP.40 - From Idea to App in Hours: How Entrepreneurs Use Lovable & AI - Part 2

In this episode of Inside the 90, Jami and Andrew continue their AI conversation by exploring how they use ChatGPT, custom GPTs, and AI-powered workflows in leadership, EOS implementation, coaching, and marketing. They discuss practical ways AI enhances conversations—not replaces them—while also diving into the future of SEO, Answer Engine Optimization (AEO), and what they call “vibe marketing.” The episode highlights how entrepreneurs and leaders can thoughtfully integrate AI into culture, communication, and strategy without losing the human element. Key Topics - Why this episode serves as Part 2 of the AI and vibe coding discussion. - Using custom GPTs for EOS coaching, leadership, and quarterly conversations. - How Kolbe and Working Genius data improve AI-assisted communication. - The difference between enhancing conversations vs. replacing conversations with AI. - AI as a tool for intentional leadership and management development. - The accidental cultural impact AI experimentation had inside Wonder. - SEO vs. AEO (Answer Engine Optimization) and how search behavior is changing. - “Vibe Marketing” and how AI is transforming copywriting and content creation. Chapters 00:00 - Intro: Continuing the AI conversation from Part 1. 03:00 - How Jami uses ChatGPT, Grok, and Gemini differently. 07:00 - Creating custom GPTs for EOS coaching and leadership support. 14:00 - Using Kolbe and Working Genius inside AI conversations. 22:00 - Enhancing conversations vs. replacing conversations with AI. 30:00 - Leadership, EOS, and using AI to improve quarterly conversations. 38:00 - How AI experimentation impacted Wonder’s company culture. 45:00 - Introducing “vibe marketing” and the shift in search behavior. 52:00 - SEO vs. AEO (Answer Engine Optimization). 59:00 - AI-assisted copywriting, brand voice, and FAQs. 01:06:00 - Responsible AI governance and recommendations from Jeff Yelton. 01:11:00 - Final thoughts on AI adoption and staying relevant. Mentions & Credits Grok — https://grok.x.ai/ Kolbe Corp — https://www.kolbe.com/ Working Genius — https://www.workinggenius.com/ EOS Worldwide — https://www.eosworldwide.com/J eff Yelton — https://www.linkedin.com/in/jeffyelton/ Wonder — https://workwithwonder.com/

EP.39 - From Idea to App in Hours: How Entrepreneurs Use Lovable & AI

In this episode of Inside the 90, Jami and Andrew dive deep into AI, vibe coding, and the rapid evolution of tools like Lovable, Claude, and Google AI Studio. They share real-world examples of building internal software, automating workflows, replacing spreadsheets, and creating custom business tools without traditional development teams. The conversation focuses on how entrepreneurs can use AI to solve operational gaps, improve efficiency, and rethink the future of software, workflows, and business systems. Key Topics - The three groups of people reacting to AI: excited, curious, and unaware. - What “vibe coding” is and how non-developers are building real software. - Using Lovable and Google AI Studio to create custom business applications. - Replacing spreadsheets and bloated SaaS tools with focused AI-powered apps. - Wonderbread: building an internal operational dashboard for an agency. - Creating stress assessments, recruiting systems, portals, and internal tools with AI. - How AI enhances workflows instead of replacing strategic thinking and process. - Why entrepreneurs need to experiment with AI now to avoid falling behind. Chapters 00:00 - Intro: Why Jami and Andrew are excited about AI. 03:00 - The three camps of AI adoption in business today. 07:00 - Jeff Yelton’s books and responsible AI leadership. 11:00 - Discovering vibe coding and early experiments with AI Studio. 17:00 - Building Wonderbread and replacing spreadsheets with custom software. 26:00 - How Lovable enables entrepreneurs to build software without coding. 34:00 - Creating stress assessments, grading tools, and single-use applications. 42:00 - Building recruiting systems, intranets, and operational dashboards. 50:00 - AI-powered quoting systems and manufacturing use cases. 58:00 - Why focused internal tools outperform bloated SaaS products. 01:05:00 - Security, scalability, and knowing when to pause AI projects. 01:11:00 - Advice for entrepreneurs experimenting with AI and vibe coding. Mentions & Credits Lovable — https://lovable.dev/ Jeff Yelton — ttps://www.linkedin.com/in/jeffyelton/ Strategic Coach — https://www.strategiccoach.com/ Dan Sullivan — https://www.strategiccoach.com/coach/dan-sullivan/ Flywheel Co-Working — https://flywheelgreenville.com/

EP. 38 - How to Run Effective Meetings and Get More Done

In this episode of Inside the 90, Andrew talks about how to fix ineffective meetings and move from “ugly and bad” to better. The conversation breaks down why most meetings fail, lack of structure, purpose, and follow-through, and how implementing a consistent cadence, clear outcomes, and simple rules can dramatically improve productivity. Andrew and Jami highlight EOS meeting rhythms, practical scheduling tactics, and cultural habits that turn meetings into a powerful tool for alignment, accountability, and execution. Key Topics - Why most meetings fail and how poor structure leads to wasted time. - The importance of meeting cadence: annual, quarterly, and weekly (L10). - Difference between “working on” vs. “working in” the business meetings. - Why adding meetings initially can actually lead to fewer meetings long-term. - Practical rules: 15/45-minute meetings, no meetings on Fridays, and time buffers. - Setting clear meeting outcomes to improve efficiency and focus. - Using L10 principles across all meetings, including client meetings. - Building a meeting culture that prioritizes accountability and execution. Chapters 00:00 - Intro: The “ugly, bad, and better” of meetings. 02:00 - Why meetings matter and common frustrations teams face. 05:00 - Root causes of bad meetings: no agenda, no structure, no outcomes. 09:00 - EOS meeting cadence: annual, quarterly, and weekly L10s. 14:00 - Working “on” vs. “in” the business meetings explained. 20:00 - Why adding meetings can lead to fewer meetings over time. 25:00 - Practical scheduling rules: 15/45-minute meetings and no Fridays. 32:00 - Writing clear outcomes for every meeting. 36:00 - Using L10 principles in all meetings (internal and external). 42:00 - Creating meeting rhythms and accountability systems. 48:00 - Closing the loop: buffers, to-dos, and meeting follow-through. 52:00 - How to roll out better meeting practices across your organization. Mentions & Credits Death by Meeting by Patrick Lencioni — https://www.tablegroup.com/product/death-by-meeting/ EOS Worldwide — https://www.eosworldwide.com/ Level 10 Meeting (EOS) — https://www.eosworldwide.com/blog/level-10-meeting

EP. 37 - What Is Kolbe? Unlock Team Performance and Hiring Success

This episode of Inside the 90 dives into the Kolbe assessment and how it helps individuals and teams understand instinctive strengths, reduce friction, and improve performance. Jami shares his journey discovering Kolbe and explains how it differs from personality tests by measuring instinct (conative behavior). The conversation breaks down the four Kolbe indexes, how to use Kolbe A, B, and C together, and how pairing Kolbe with tools like Working Genius can transform hiring, team dynamics, and leadership effectiveness. Key Topics - What Kolbe is and how it differs from personality and IQ assessments. - The three parts of the brain: cognitive, affective, and conative. - The four Kolbe indexes: Fact Finder, Follow Through, Quick Start, and Implementer. - How instinct-driven behavior impacts team dynamics and communication. - Using Kolbe A, B, and C to evaluate individuals, roles, and expectations. - Identifying tension vs. strain and how misalignment leads to burnout. - Avoiding “cognitive cloning” and building balanced teams. - Pairing Kolbe with Working Genius to optimize hiring and team performance. Chapters 00:00 - Intro: Why this episode applies to individuals, teams, and organizations. 02:00 - Jami’s journey discovering Kolbe and early assessment tools. 06:00 - The “aha moment” using Kolbe to improve team relationships. 10:00 - The three parts of the brain and what Kolbe actually measures. 15:00 - Kolbe A, B, and C explained (individual vs role expectations). 20:00 - Breaking down the four Kolbe indexes (Fact Finder, Follow Through, Quick Start, Implementer). 30:00 - Real-world examples of how Kolbe shows up in work and leadership. 38:00 - Team dynamics: tension, strain, and avoiding cognitive cloning. 45:00 - Using Kolbe in hiring and building high-performing teams. 52:00 - How to implement Kolbe in your organization step-by-step. 58:00 - Final thoughts and upcoming EOS Conference meetup. Mentions & Credits Kolbe A Index — https://www.workwithwonder.com/store Wonderlic Test — https://wonderlic.com Strategic Coach — https://www.strategiccoach.com Working Genius — https://www.workinggenius.com CliftonStrengths — https://www.gallup.com/cliftonstrengths DISC Assessment — https://www.discprofile.com Enneagram — https://www.enneagraminstitute.com Wonder — https://workwithwonder.com