#009 — José Caballer

#013 — Kasey Devine

Kasey Devine is a Midwest-based entrepreneur and former HR and sales leader who’s spent over a decade inside the payroll, benefits, and PEO world, helping teams grow through complexity, change, and scale. After rising through leadership roles at companies like ADP and TriNet—and realizing he’d outgrown traditional corporate paths—Kasey left to build Entravia, a venture-backed HR tech startup designed to simplify one of the most opaque industries small business owners face. Grounded in faith and driven by problem-solving, his work focuses on removing friction, restoring clarity, and building tools that actually help the people keeping the economy running. Summary In this conversation, Kasey Devine shares his unique journey from a sales role to becoming an entrepreneur and the founder of Entravia. He discusses the challenges and lessons learned throughout his career, particularly during the COVID-19 pandemic. Kasey emphasizes the importance of resilience, problem-solving, and ethical leadership in business. He also delves into the significance of PEOs for small businesses and how technology can streamline complex processes. The conversation highlights Kasey's mission-driven approach to entrepreneurship and his vision for the future of Entravia. In this conversation, Kasey Devine and Kevin Mooney explore various themes related to leadership, problem-solving, and the dynamics of startups. They discuss the importance of execution, building cohesive teams, understanding personality types, and the art of hiring. The conversation also delves into the challenges of navigating the startup landscape, funding strategies, and the evolution of technology in development, particularly through the lens of vibe coding and AI. Throughout, they emphasize the significance of communication, networking, and learning from failures as essential components of personal and professional growth. Find Kasey: https://entravia.co/ https://www.linkedin.com/in/kaseydevine/ Affiliate Links: Webflow: https://try.webflow.com/1p91anb2byd3 Bloom: https://bloom.cello.so/hXX9A7c0zQc Chapters: 00:00 Introduction and Background 05:31 Learning and Growth at ADP 08:02 Leaving ADP and New Opportunities 10:54 Understanding PEOs and Their Importance 13:46 Challenges in the Startup Environment 16:26 The Entrepreneurial Mindset 19:31 Building a New Venture 22:08 Reflections on Employment and Entrepreneurship 27:40 Finding Purpose and Taking Risks 29:20 The Birth of Entravia 30:16 Identifying Industry Gaps 32:04 Leveraging Technology for Small Businesses 33:27 The Mission Behind Entravia 36:25 Data Ownership and Accessibility 38:38 Business Model Evolution 40:27 The Importance of Problem Solving 41:10 Capitalism and Problem Solving 48:16 Navigating Investor Relationships 50:29 Building a Values-Driven Team 58:52 The Importance of Communication in Startups 01:01:39 Building a Cohesive Leadership Team 01:04:39 Understanding Personality Types in Hiring 01:06:47 The Art of Effective Communication 01:10:01 Navigating the Challenges of Hiring 01:12:11 The Role of Trust and Alignment in Business Success 01:12:35 Funding and Growth Strategies for Startups 01:16:07 Exploring Vibe Coding and Its Impact 01:22:15 The Role of AI in Startup Development 01:29:05 Understanding the Sales Perspective 01:32:32 Building Relationships for Investment 01:34:25 Identifying Market Needs and Solutions 01:38:05 Listening to the Inner Voice 01:41:41 Adapting Business Models 01:45:39 The Importance of Customer Discovery 01:51:47 Personal Growth Through Challenges 01:55:33 Final Thoughts and Wisdom

#012 — Felice Della Gatta

For the past fifteen years, Felice has worked with small teams all over the world to design brands, products, and marketing and advertising campaigns that are beautiful, impactful, and meaningful. But all he really cares about is doing good work with good people. He facilitates, researches, empathizes, creates systems, writes, scribbles, daydreams, picks colors, and pushes pixels while juggling business goals, handling project constraints, and designing for excellence — all with ethics. Summary: In this conversation, Felice Della Gatta and Kevin Mooney explore the nuances of design, branding, and the evolution of a freelancer into a collaborative role. They discuss the importance of understanding clients, the balance between product and brand marketing, and the challenges of defining what 'right' means in design. The dialogue emphasizes the need for creative confidence, the value of community, and the significance of feedback in the design process. In this conversation, Felice Della Gatta and Kevin Mooney explore the intricacies of client relationships in the design industry, emphasizing the importance of respect and understanding in the creative process. They discuss the challenges freelancers face in maintaining authority while managing client expectations and feedback. Find Felice: https://felicedellagatta.com/ https://www.linkedin.com/in/felicedellagatta/ Affiliate Links: Webflow: https://try.webflow.com/1p91anb2byd3 Bloom: https://bloom.cello.so/hXX9A7c0zQc Chapters: 00:00 The Informal Podcasting Approach 00:00 Building Connections Through Conversations 00:20 The Value of Casual Conversations 02:50 Understanding Clients Beyond Design 05:37 The Role of Product in Branding 08:33 Brand Marketing vs. Product Marketing 11:14 The Journey of a Freelancer 13:55 Shifting Perspectives on Freelancing 16:38 The Desire for Community and Collaboration 19:31 Defining 'Right' in Design 21:59 The Challenges of Team Dynamics 24:42 Finding the Right Fit in Hiring 27:22 Reaping the Benefits of Experience 29:59 Navigating Client Relationships 38:16 The Nuances of Branding and Perception 40:51 The Importance of Input in Creative Processes 43:54 Selling Ideas vs. Selling Products 51:23 Creative Confidence and Responsibility 57:12 Navigating Client Relationships and Feedback 01:07:38 Client Relationships and Respect 01:11:53 The Role of the Consultant 01:16:52 Working with Small Businesses 01:22:55 Balancing Operations and Authority 01:30:13 Lead Generation Strategies 01:41:49 The Value of Conversations 01:44:27 Creating Meaningful Content 01:51:47 Navigating the 7-11-4 Rule 01:55:43 Finding Purpose in Change 02:06:15 Embracing New Opportunities Takeaways: - Casual conversations can lead to valuable insights. - Understanding clients' backgrounds is crucial for effective design. - Product quality often outweighs brand in early stages. - Brand marketing should complement product marketing. - Freelancing can evolve into collaborative opportunities. - Community and connection are vital for growth. - Design excellence requires teamwork and shared values. - Team dynamics can significantly impact project outcomes. - Defining 'right' in design is subjective and challenging. - Input quality is essential for creative output. I have the utmost respect for my clients, all of them. - I am very selective with my clients because I've worked in companies that were creating misery. - Clients are very close to the work, which can be both good and bad. - I have a very good example of what not to do, who not to work with. - I share with you everything that I know, and then I step back. - I want to enable people and help them get to their goals. - Everything in business comes down to lead generation. - I want to create content that aligns with my values. - I want to uncover opportunities and enable people. - I trust that I am where I need to be right now.

#011 — Marcelo Russo

Marcelo Russo is an Argentine-born visionary dedicated to helping people and ideas find each other — blending technology, empathy, and strategy to make others smarter and more connected. He is the Co-founder of Fri3nds Agency. Find Marcelo: Website: www.fri3nds.com [https://www.fri3nds.com] Instagram: @themarcerusso [https://www.instagram.com/themarcerusso/] X: @themarcerusso LinkedIn: Marcelo Alejandro Russo [https://www.linkedin.com/in/themarcerusso/] Affiliate Links: Webflow: https://try.webflow.com/1p91anb2byd3 Bloom: https://bloom.cello.so/hXX9A7c0zQc Chapters: 00:00 Admiring Brilliance: A Conversation About Leadership 05:21 From Tech to Creativity: Marcelo's Journey 10:25 Building a Creative Agency: The Friends Agency 15:14 Navigating Growth: From 17 to 4 20:33 The Challenge of Scaling: Retaining Talent 29:45 Navigating the Challenges of Agency Management 35:30 Establishing Guiding Principles for Team Dynamics 42:25 The Role of Organizational Health in Business Success 52:57 Learning from Past Mistakes: Growth and Adaptation 01:01:19 Ego and Opportunity: Expanding Business Verticals 01:07:44 The Importance of Cohesion in Teams 01:13:40 Navigating Client Engagements 01:20:23 Creating Productive Friction 01:28:21 Transformative Relationships and Personal Growth 01:39:18 Dog Tales and Personal Connections 01:46:25 Networking Adventures in New York 01:50:53 The Value of Authentic Connections 01:58:50 Breaking the Ice: Vulnerability in Conversations 02:06:01 The Nature of Conversations 02:11:15 The Role of Hobbies in Life 02:19:58 The Pressure of Monetizing Hobbies 02:26:49 Finding Joy in the Process Takeaways: * The importance of networking and relationship building in business. * The significance of protecting and supporting your team as a leader. * The balance between technology and creativity in agency work. * The transition from a large team to a smaller, more efficient core team. * The importance of trust and transparency in team dynamics. * Navigating challenges during downsizing and maintaining growth. * The role of accountability in business relationships. * Hiring principles that prioritize cultural fit and friendship. * The value of building personal relationships in business. * The significance of organizational health in team success. * The intersection of business strategy and creativity in agency work. * The importance of open communication with clients. * Learning from mistakes and viewing them as growth opportunities. * The need for strategic thinking in client engagement. * The balance of creativity and operations in agency work. * The importance of client retention and relationship management. * Overcoming the fear of public speaking can lead to new opportunities. * Networking can be transformational and energizing. * Community connections can provide endless optimism for the future. * It's important to focus on personal connections rather than just business. * Balancing creativity with business demands is crucial for satisfaction. * Hobbies should be pursued for joy, not just as potential businesses. * Finding the right partners can enhance personal and professional growth. * Your network can significantly impact your success and happiness. * Pursuing passions can lead to unexpected opportunities and connections.

#010 — Maruo Medina Susarrey

Mauro Medina Susarrey is a Brand Designer & Creative Director with over 15 years of experience working at the intersection of creativity and strategy. His career has been guided by curiosity and a willingness to explore the unknown—qualities that have taken him across industries, disciplines, and countries. Early in his journey, Mauro co-founded a design studio (2009–2014) where he collaborated with clients in entertainment, tech, data analysis, medical, sports, food supplements, consumer goods, festivals, and non-profits. During this time, he also worked as a production designer on commercials and music videos, including projects for The Format and Pontiac. These experiences exposed him to the many layers of design and storytelling, inspiring him to see brands not as one-dimensional but as living, breathing ecosystems. Over the years, Mauro has worked across photography, film, motion graphics, sound design, web development, and brand strategy. This multidisciplinary background gives him a 360° perspective on how brands come to life across different mediums and contexts. His portfolio spans global collaborations with clients such as ConsenSys, CoinMarketCap, Formosa Group, and Facebook, and his projects have taken him to cities like Los Angeles, New York, San Francisco, London, Singapore, Paris, and Mexico. Today, Mauro runs a design studio alongside his wife, an architect and interior designer. Together, they focus on bridging the Gap of the tangible and intangible sides of branding—crafting strategies, environments, and experiences that bring brands to life in a holistic way. Find Mauro: Website: https://kult.mx Linkedin: www.linkedin.com/in/maurodesigner Instagram: https://www.instagram.com/bymauro.mx/ Instagram Kult: https://www.instagram.com/studiokultmx/ Affiliate Links: Webflow: https://try.webflow.com/1p91anb2byd3 Bloom: https://bloom.cello.so/hXX9A7c0zQc Chapters: 00:00 The Journey Begins. From Mexico to Graphic Design 09:52 Facing Challenges: The Impact of ESL Classes 20:05 The Shift to Strategy: Learning and Unlearning 30:08 Deepening Understanding: The Role of Client Relationships 33:14 The Birth of a Brand 34:05 Navigating Client Relationships 37:21 From Jack of All Trades to Specialization 43:31 Transitioning to Ensenada 46:14 Cultural Shifts in Design 51:49 Building Relationships in Business 01:05:40 Emotional Connections in Branding 01:09:28 Reading Visual Cues for Emotional Connection 01:10:44 The Importance of Authentic Client Relationships 01:12:00 Cultural Shifts in Design and Branding 01:14:02 Challenges in the Tech Industry 01:15:55 The Role of Empathy in Tech Branding 01:16:50 Navigating Software Limitations and Client Needs 01:23:00 The Frustration with Automated Customer Service 01:24:42 The Ethical Dilemma of AI in Design 01:29:39 Generational Perspectives on Technology and Relationships 01:39:30 The Cynical Nature of Brands and Consumer Relationships 01:40:28 Revisiting Brand Ethics and Responsibility 01:43:50 The Ethics of Design in Modern Society 01:47:29 Resilience and Sticking to Your Principles 01:50:33 Navigating Client Relationships and Strategy 01:57:23 The Importance of Context in Strategy 02:08:45 The Power of Design and Community Influence Takeaways: - Recognizing effective strategies can be challenging. - Shifting perspectives is crucial for achieving better results. - Initial skepticism is common when encountering new strategies. - Mindset shifts require effort and awareness. - It's important to acknowledge when something is better. - The conversation highlights the difficulty of change. - Effective strategies often come with a learning curve. - Understanding the point of contention is key to progress. - Embracing new ideas can lead to significant improvements. - The journey of recognizing better strategies is ongoing.

#009 — José Caballer

José Caballer is Designer, creative director, educator, and entrepreneur, known for blending design thinking with business processes to help organizations and creative professionals thrive.With over 28 years of experience in design and digital technology, Jose started his journey at the Art Center College of Design and became a Design Director at Razorfish during the dot-com boom in 1997. In 2001, he founded The Groop, a creative agency that earned recognition as one of the Inc 500 fastest-growing companies.In 2012, José pivoted towards education with the launch of The Skool, an innovative platform that later became The Futur, where he focused on teaching business skills to creatives. His work at the intersection of design, business, and technology led him to ConsenSys in 2017, where he integrated blockchain solutions into design frameworks.José founded The Systm, focusing on developing high-performance work methodologies, inspired by design thinking, startup frameworks, and his passion for aligning personal growth with business success. Through The Systm, José coaches creative leaders on optimizing workflows and building sustainable, innovative businesses.As a coach, facilitator, and mentor, José’s mission is to revolutionize how work is done by empowering individuals to align their mind, body, and spirit with their professional pursuits, creating high-fidelity, collaborative teams that thrive in the 21st century. Find José: https://thesystm.co/ https://www.linkedin.com/in/josecaballer/ https://www.instagram.com/josecaballer/ Affiliate Links: Webflow: https://try.webflow.com/1p91anb2byd3 Bloom: https://bloom.cello.so/hXX9A7c0zQc Chapters: 00:00 Navigating Burnout: A Personal Journey 14:00 Lessons from the Universe: Co-Creation and Self-Discovery 27:43 Building Community: The Intersection of Purpose and Connection 30:59 Cultural Reclamation and Film Development 31:24 Pursuing Passion Projects 32:22 Life Transitions and Daily Rituals 33:22 The Great Reset: Finding Clarity 35:12 The Joy of Podcasting 36:37 Sacrifices for Passion 37:01 Building a Community and Finding Value 38:40 Launching a School and Creating Value 41:02 The Importance of Belief and Execution 42:45 Providing Value and Asking for Money 43:42 Unique Perspectives on Brand Strategy 45:30 Building Cohesive Teams 48:14 The Playground of Ideas 50:02 Collective Health and Organizational Purpose 52:31 Future-Proofing Through Community 55:35 Defining Purpose in a Collective 57:12 Navigating Imposter Syndrome 58:54 The Role of Community in Execution 01:01:14 Navigating Identity and Accountability 01:03:33 Understanding Organizational Dynamics and Personal Trauma 01:07:09 The Evolution of Creative Work and Personal Growth 01:11:02 Redefining Work and Life Around Essence 01:14:01 Creating Community and Sharing Stories 01:16:15 Developing Core Concepts and Personal Goals Takeaways: - Burnout can stem from overwhelming responsibilities and lack of self-care. - Coaching can provide valuable insights and support during personal crises. - Creating a community can foster collective growth and accountability. - Self-discovery is a continuous journey that requires vulnerability and honesty. - Authenticity in one's work leads to greater fulfillment and impact. - Setting boundaries is crucial for maintaining mental health and well-being. - The importance of sharing personal stories to connect with others. - Navigating the complexities of identity and societal expectations is essential for growth. - Embracing change and uncertainty can lead to new opportunities. - Collaboration and co-creation can enhance personal and professional development.