Insights

Fractional CFOS: Help your clients be more data-driven and capture the opportunity on the table with our Tactical Opportunity Calculator! Great for managing your business and your clients businesses to make sure they maximize value! Access the tool here: https://pineapplecf-value-estimator.replit.app/ More on us: https://pineapplecf.com

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.

Fractional CFOs - find value for your clients and quantify the cost of *not* doing something (like hiring a Fractional CFO to help guide the roadmap. Access the tool here: https://pineapple-strategic-opportunity-calculator.replit.app/ More on us here: https://pineapplecf.com

Get the right, data-driving KPIs for your clients! This tool helps you have the best KPIs for you or your clients industry and how to build them! Test the tool here for free: https://kpi-strategy.pineapplecf.com/ More on us here: https://pineapplecf.com

If you run a consulting company, you need a dashboard to see all your operations in one spot. We use it ourselves, and we use it with a bunch of other consulting clients too! More on us: https://www.pineapplecf.com/ White label dashboards: https://www.pineapplecf.com/white-label-dashboards

In dashboard design, there are principles that matter a LOT. We go through the importance of color matching here so your dashboards can be instantly understandable. More on us here: https://www.pineapplecf.com/ Training here: https://www.pineapplecf.com/analyst-training

Here's a real life example of an L10 Scorecard for a Marketing Firm client running EOS. Stick to principles like this and you'll be data-driven the easy way! Custom L10 Scorecard: https://www.pineapplecf.com/eos-custom-l10-scorecards More on us in general: https://www.pineapplecf.com/

Consulting Leaders - Data advice for consultants checklist: • If leaders can see the story in their numbers in 15 seconds, better decisions follow naturally. • Vanity metrics do not grow businesses, tracking only what drives action does. • Content does not need massive reach to work, it needs the right audience and consistency. More on Jack and Pineapple: www.pineapplecf.com Listen to the full episode: Apple Podcasts: https://podcasts.apple.com/us/podcast/how-to-build-a-data-driven-consulting-firm-through/id1714675768?i=1000746720923 Spotify: https://open.spotify.com/episode/5a8Mv96eY1dWsfp1VaZ9NQ