Business lessons don’t always come from polished plans — most come from figuring it out as you go. Jack pulls up a chair with Cassandra D’Alessio, founder and Chief Content Strategist at Next Page Brand Strategies, for a real, funny, and honest conversation about what actually builds a sustainable consulting business. Most successful consultants didn’t start with confidence, clarity, or perfect systems. They started scrappy. Cassandra shares how growing up constantly moving, working early retail jobs, navigating teaching and corporate life, and eventually launching her own business shaped the adaptability and boundaries she relies on today. This conversation weaves through early career missteps, confidence-building moments, tough client lessons, and the reality of enforcing contracts when it matters. Jack and Cassandra also dig into how storytelling and data work together, why boundaries are essential for consultants, and how to grow without burning out or losing what makes your business you. Along the way, there’s plenty of laughter, rapid-fire personality questions, and those “oh wow, that’s me” moments — especially if you’ve ever wondered whether everyone else is secretly figuring it out as they go too. *What Comes Up When Consultants Talk Shop:* 🍍 Cassandra’s unconventional path from teaching to entrepreneurship 🍍 How moving constantly as a kid built scrappiness and adaptability 🍍 Early retail jobs that shaped her work ethic (flowers, liquor, and life lessons) 🍍 Business lessons from difficult client relationships — and enforcing contracts 🍍 Why onboarding meetings still matter (and when in-person is worth it) 🍍 Inbox habits, productivity quirks, and real-life consultant systems 🍍 How storytelling and data work together in smart marketing 🍍 Cassandra’s content strategy for service-based businesses 🍍 A rapid-fire look at consultant personalities, boundaries, and working styles *Key Moments:* 00:00 Intro 08:55 The First Jobs That Quietly Shaped How She Works Today 16:40 What Finally Pushed Her to Start Her Own Business 25:20 The Moment She Realized Scrappy Alone Wasn’t Enough 33:45 Learning the Hard Way How to Handle Client Boundaries 42:10 How Data and Storytelling Actually Work Together 51:05 What Being Scrappy but Successful Looks Like Now If you’re a consultant, business owner, or entrepreneur navigating client boundaries, confidence, and growth — this episode will feel like sitting in on a conversation you wish you could have behind the scenes. 🎧 Listen, subscribe, and share if this episode hits close to home. ABOUT CASSANDRA D’ALESSIO: Founder & Chief Content Strategist, Next Page Brand Strategies Learn more about Cassandra and connect at https://www.turnthenextpage.com/ ABOUT JACK TOMPKINS & PINEAPPLE CONSULTING FIRM Jack (aka "Pineapple Jack") is the host of Scrappy but Successful, a professional speaker, and the founder of Pineapple Consulting Firm. As one of the early Fractional Analysts, Jack brings his clients' data to life with storytelling visuals and impactful insights while adding a sense of humor that makes analytics actually fun. You’ll see that fun come through in spades on Scrappy but Successful as he aims to bring out the guest’s personality through laughter and stories, while giving listeners some pretty useful takeaways along the way. Head to https://www.pineapplecf.com/ to turn your data into visual, understandable, decision-driving insights.

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