The non-traditional path that built real freedom with Dave gilbert episode artwork

EPISODE · Jul 28, 2026 · 29 MIN

The non-traditional path that built real freedom with Dave gilbert

from Scaling the Gap · host Madeleine MacRae

DescriptionIs building the biggest company possible really the definition of success?In this episode of Bold Enough, Madeleine MacRae speaks with entrepreneur David Gilbert about his unconventional career across technology, real estate, business acquisitions, fractional consulting, and engineering.David explains why starting a company and purchasing an established business come with completely different challenges. He also challenges the growth-at-all-costs mindset, sharing why sustainable growth, strong culture, quality service, and a healthy life can matter more than chasing unicorn status.The conversation also explores the emotional reality of leaving a company you helped build. David shares how closely a founder’s identity can become connected to their business, why an exit can create an unexpected period of grief, and how he learned to redefine success beyond professional achievement.For David, real success means having the freedom to choose how you spend your time, building meaningful relationships, remaining grateful, and creating a life that allows your family to thrive.Connect with David Gilbert:LinkedIn: https://www.linkedin.com/in/davidmgilbert/Follow Madeleine:Website:https://madeleinemacrae.com/books/LinkedIn:https://www.linkedin.com/in/macraemadeleineInstagram:https://www.instagram.com/madeleine.macrae/Book:The Tenacious Pursuit of Peace: Where to Go When Success Isn’t Enough

Episode metadata supplied by the publisher feed · Published Jul 28, 2026

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