In this episode of How I Started, host Andrew Kappel interviews Greg DiFraia, the CEO of Inlayer and a longtime technology leader with a career spanning Dell EMC, Turbonomic, Scality, and beyond. Greg shares his remarkable journey from starting in sales and operations roles at small tech resellers to leading emerging technology groups inside one of the world’s largest tech companies—and eventually stepping into the CEO seat at a fast-growing startup.

Greg dives into the experiences that shaped his leadership philosophy, including the critical role of mentorship, the importance of building deep technical knowledge even with a marketing degree, and how he navigated the transition from big corporate environments to scrappy startup life.

He also shares his philosophy on building company culture, scaling innovation, the reality of raising capital as a CEO, and why relentless self-development is at the core of his career journey.

Greg’s story offers incredible insights for anyone passionate about leadership, technology innovation, startups, or personal growth.

Takeaways

- Greg started his tech career in Rhode Island, working for value-added resellers before moving to Dell EMC.

- Transitioned from a marketing background to technical leadership by investing in certifications, mentorship, and relentless self-education.

- Helped scale Dell EMC through major milestones, including the VMware acquisition and rapid employee growth.

- Embraced the startup world with Turbonomic and Scality, helping companies innovate, grow alliances, and drive strategic partnerships.

- Took the leap to an early-stage company, now leading Inlayer’s growth as CEO.- Highlights the importance of networking, mentorship, and proactive career planning.

- Shares how startup leadership requires flexibility, relationship-driven execution, and personal ownership of company success.

- Talks about building work culture that is both performance-driven and deeply human-centered.- Focuses on constant learning—even (and especially) when outside the comfort zone.- Believes in balancing professional ambition with intentional personal growth and life balance.

Chapters

00:00 – Welcome to Rhode Island and Greg’s Career Overview

01:45 – Starting in Tech with Resellers and Integrators

03:30 – Moving from Marketing Degree to Technical Roles

06:00 – Scaling with Dell EMC and Mentorship Lessons

08:45 – Transitioning to Startups: Turbonomic and Scality

11:30 – Joining Early-Stage Companies and Building from Scratch

14:00 – Challenges and Opportunities of Startup Leadership

16:45 – Building a Strong Company Culture and Team

19:20 – Developing New Skills as a First-Time CEO

21:00 – Managing Growth, Fundraising, and Personal Development

23:30 – Work-Life Balance Challenges at High-Growth Companies

26:00 – Where to Learn More About Inlayer

Leadership, technology startups, career growth, mentorship, innovation, tech sales, startup CEO, professional development, Inlayer, network management, venture capital, self-development, technical sales, Rhode Island tech, EMC, Dell EMC, Turbonomic, Scality, startup culture, entrepreneurship, SaaS, API platforms, human-centered leadership, How I Started Podcast, career planning, building companies, executive leadership, scaling startups, emotional intelligence

📍 Learn more about Inlayer: ⁠https://inlayer.com/⁠

🌐 Learn more about Phonism (product): ⁠https://phonism.com/⁠

🔗 Connect with Greg DiFraia: ⁠https://www.linkedin.com/in/greg-difraia-7914704/⁠

Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/andrewkappel/