As the year closes, one powerful question rises to the surface. What does it take for someone to walk away from the comfort of a Wall Street career, the predictable salary, and the traditional definition of success, and instead choose the wild, uncertain, and incredibly rewarding path of entrepreneurship?In this powerful episode, Madeleine MacRae sits down with Dave Gilbert, a founder whose entire entrepreneurial journey refuses the traditional script. After two decades in tech, real estate, and e-commerce, and after building a company from two people to 5,000 employees, Dave discovered that success was not about chasing unicorn valuations or 100 hour weeks. It was about freedom, meaningful relationships, and building companies where people actually love working.Dave opens up about his winding career, the emotional cost of selling a company, the grief that follows identity loss, and the joy of building his fractional executive firm where world class leaders bring 20 to 30 years of experience to companies that could never afford them full time. He also talks about redefining ambition, designing a life you want to live, and choosing work that aligns with who you are, not just what you can build.As we step into 2026, Dave's story is the reminder we all need: success is not about scale. It is about intention. And this year, you deserve a life that feels as good on the inside as it looks on the outside.Wishing you a grounded, purpose filled, deeply joyful start to 2026. More transformative guests on the way!Key TakeawaysWhy non-traditional careers are becoming the new norm and why that is a giftWhy fractional executives are becoming the future of growth for small and mid sized businessesThe hidden grief founders experience when they exit their companiesWhy chasing unicorn status creates unhealthy pressure and what sustainable success actually looks likeHow to build companies where people stay because they want to, not because they have toWhy success is less about money and more about freedom, family, and meaningful relationshipsIn This Episode[00:00] Introduction to David Gilbert[04:43] Validating career paths and startup hiring[05:08] Tech startup exit and business growth[05:56] Fractional executive firm vision and passion[06:37] Benefits of fractional executives[09:39] Challenges of buying vs building companies[11:56] Service vs product business models[12:27] Growth mindset: unicorns vs sustainable companies[13:41] Redefining success and profit[16:16] Identity and grieving after exiting a company[19:59] Defining personal success[23:58] Closing thoughts and contact informationNotable Quotes[15:34] “Who you are is how you treat people and what you do with your life and how you spend your time. It's not what you did in your career or the company that you grew.” – David[21:01] “Spending time with people that we want to spend time with that we choose to spend time with, to me, is the ideal success story.” – DavidOur GuestDave Gilbert is a tech founder, entrepreneur, and owner of multiple companies including a fractional executive firm and an engineering company. After two decades building businesses across tech, real estate, and e-commerce, Dave now leads a 30 person team that delivers fractional CFO, HR, and back office services. His passion is sustainable growth, meaningful relationships, and building companies where people truly thrive.Resources and LinksDavid GilbertEmail: Dave@ProvenCoLinkedIn: ⁠linkedin.com/in/davidmgilbert⁠Madeleine MacRaeWebsite - ⁠https://mmmacrae.com/making-changes-training-motivating/⁠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

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