The Art of the Pivot: Lessons from Losing It All & Starting Over

13/10/2025 29 min Episodio 1532
The Art of the Pivot: Lessons from Losing It All & Starting Over

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Episode Synopsis

Ever felt like life knocked you flat just as things were going great? Dar Holdsworth knows that story well. From doing multi-million-dollar signage deals to building award-winning custom motorcycles for celebrities — then losing everything and starting over — Dar’s entrepreneurial journey is anything but straight. In this episode, Tyler Jorgenson and Dar dig into what it really takes to reinvent yourself, spot new opportunities, and keep moving forward even when your first (or second… or third) business doesn’t go as planned.Whether you’re riding the highs of business growth or rebuilding after a major setback, Dar’s story is a masterclass in grit, curiosity, and knowing when to pivot.What You’ll LearnThe unexpected push that got Dar to launch his first businessHow losing his biggest client — and going through a divorce — forced a total resetLessons from building custom motorcycles and scaling product sales onlineThe key difference between being great at your craft and running a profitable companyHow discovering funnels (and a free + shipping offer) changed everythingWhy Dar now helps other entrepreneurs launch AI SaaS businesses that scaleChapters00:00 Introduction to Dar Holdsworth02:07 The Entrepreneurial Journey Begins05:09 Overcoming Early Obstacles09:03 Transitioning to Custom Motorcycles12:02 Lessons from the Motorcycle Business17:04 The Shift to SaaS and AI21:00 Navigating Challenges in the Chiropractic Niche24:54 Current Ventures and Future Aspirations