31. Stop Building Yourself Another Job: Fractional CXO Company Building with Natalie Hoop

In this episode of Scrappy But Successful, Jack sits down with Natalie Hoop, a fractional COO and coach for fractional consultants, to unpack what it really takes to build a fractional business that works. Natalie shares her scrappy path from retail leadership at Blockbuster and Borders to startups, fractional operations, and coaching. Along the way, she tells wild behind-the-scenes stories about Blockbuster missing the DVD/Netflix moment, Borders handing online book sales to Amazon, and why companies often fail when they ignore the people closest to the customer. Jack and Natalie also dig into the real challenges fractional consultants face: undercharging, scope creep, weak positioning, vague ICPs, burnout, and accidentally building “another job” instead of a business. Natalie breaks down how fractionals can clarify what they solve, package their services, make better business decisions, and speak directly to the pain their clients actually feel. If you’re a fractional consultant, coach, operator, or founder trying to grow without burning out, this one is packed with practical advice. Chapters 00:00 Intro: Scrappy But Successful 00:59 Natalie’s scrappy roots and nontraditional path 03:34 How retail became Natalie’s business education 09:14 Blockbuster’s missed DVD and Netflix opportunities 13:28 Borders, Amazon, and the cost of bad strategic bets 15:00 Sunk cost fallacy and knowing when to pivot 18:04 Treating business changes like reversible decisions 23:36 Natalie’s first fractional client after being laid off 27:12 Undercharging, overdelivering, and scope creep 28:04 Building the right ICP instead of another job 34:12 Positioning fractional services around real client pain 46:54 Jack gets coached on Pineapple Analyst positioning Connect with Natalie: http://nataliehoop.com/   / nataliehoop     / nataliehoop_ops   Connect with Jack:   / jack-tompkins   https://www.pineapplecf.com https://www.pineappleanalyst.ai/    / @pineappleconsultingfirm