The Real Side of Entrepreneurship with Jeff Lamphere & Steph Vavonese

In the debut episode of The DG Legacy Files, guest host Matt Masur sits down with entrepreneur Jeff Lamphere and special guest Steph Vavonese, founder of SMV Recruiting, to talk about the real journey of building businesses.

They dig into the side of entrepreneurship you don’t see on Instagram: long nights, failures, self-doubt, and the constant pressure to prove yourself. Jeff opens up about his earliest ventures (including a surprising first “business” at age 12), scaling side hustles while working full-time in engineering, and the lessons he’s learned about failure, delegation, and surrounding yourself with the right people.

Key takeaways from this episode include:

• Why entrepreneurship isn’t always glamorous—and why that’s okay
• How failure and setbacks fuel growth
• The importance of community, mentorship, and the people you keep close
• Lessons from balancing corporate life with building multimillion-dollar businesses

This conversation sets the tone for The DG Legacy Files: authentic, practical, and rooted in building a legacy that goes far beyond money.