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
