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What happens when a self-proclaimed lazy kid who once walked out of high school ends up running an award-winning IT company known for creating raving fans? That is exactly what Isaac Alexander unpacks in this conversation about customer service mastery, business strategy, and sustainable growth. Isaac is the President of Quo Vadis, Charlotte’s Best IT Provider for 2025, and a former mortgage sales leader who helped scale a company from four people to more than one hundred almost overnight. From a father-in-law challenge that changed his trajectory to leading through rapid growth and rebuilding with discipline, Isaac shares the inflection points that shaped him. This conversation dives into how to improve customer service, shift customer perception, and turn a so-called “commodity” service into a competitive advantage. Isaac explains how improving customer experience through measurable response times and service standards drives customer satisfaction, customer engagement, and long-term loyalty. You will also hear how forward-looking KPIs, EOS scorecards, and disciplined business strategy support sustainable growth, scaling strategies, and smart acquisition planning. It is a practical look at customer service psychology, growth strategies, and overcoming real business obstacles without losing your edge. *What Comes Up When Consultants Talk Shop:* 🚀The father-in-law conversation that forced Isaac to level up and leave the restaurant world behind 🚀What scaling from 4 people to 100 in under two years feels like on the inside and the business obstacles that come with rapid growth 🚀Why anxiety hit hard during expansion and how discipline became the reset button 🚀The mindset shift from “we do IT” to “we are a customer service company that happens to do IT” and how that improved customer perception 🚀The 15-minute response standard that elevated customer satisfaction and changed the entire service experience 🚀Why most MSPs lose clients without realizing it and how frictionless onboarding improves customer engagement 🚀How EOS scorecards and forward-looking KPIs prepare you for scaling strategies and acquisition 🚀What it really means to dream big enough to support sustainable growth for your team and your clients 🚀The scrappy traits Isaac still carries today and the structured systems that support customer service mastery *Key Moments:* 00:00 Intro 02:10 Early Career Plot Twist And The Moment Things Got Real 14:35 The First Time She Realized Growth Creates New Problems 27:50 When Leadership Stops Being About You And Starts Being About The Team 41:20 The Conversation That Forced A Hard Business Decision 55:45 What Actually Moves The Needle In A Service Business 71:30 The Data Check That Changed How They Measured Success 88:40 The Perspective Shift That Ties It All Together ABOUT ISAAC ALEXANDER: President of Quo Vadis Inc. 13 years in the mortgage industry Learn more about Isaac Alexander and connect at https://quo.cc/ https://www.linkedin.com/company/quovadis-it https://www.facebook.com/people/Quo-Vadis/61578842335195/# https://x.com/QuoVadisInc Charlotte’s Best Award Winner: https://www.votedcharlottesbest.com/listing/2025/it-computer-services 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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Ever find yourself staring into the fridge after a long day, trying to figure out what you should eat, only to give up and grab whatever is easiest? That tug-of-war between eating healthy and just surviving the week is exactly what this conversation gets into. For this episode of Scrappy But Successful, I’m joined by longtime friend and registered dietitian Kasey Strouse, founder of Normally Nourished. We dig into how her scrappy path through restaurant jobs, tough college classes, and hospital nutrition work eventually led her to build a thriving non-diet nutrition practice. Along the way, Kasey shares how growing up with an entrepreneur dad and seeing firsthand how health challenges impact families shaped her passion for helping people build healthier, less stressful relationships with food. Kasey offers practical, judgment-free advice that makes eating well feel doable again. If you’re trying to balance real life with healthier habits without turning food into another stressful project, this episode delivers both laughs and useful takeaways. *What Comes Up When Consultants Talk Shop:* 🍍Growing up with an entrepreneur parent and how that shaped Kasey’s own business journey 🍍Why restaurant jobs teach communication skills that show up later in business and client work 🍍How organic chemistry almost derailed her plans and what she did to push through 🍍The reality of working in clinical nutrition and realizing it was not the right long-term fit 🍍Why most diets fail and what actually helps people build sustainable habits 🍍What it really means to be a “non-diet dietitian” 🍍How to eat well when you’re busy, burned out, or just don’t feel like cooking 🍍The Sunday planning habit that makes weekday meals easier 🍍Why stressing over food choices can sometimes do more harm than the food itself 🍍The truth about protein trends and why fiber deserves more attention 🍍Real-life meal ideas that work when motivation is low and schedules are packed 🍍How Kasey balances running a practice while keeping life and nutrition realistic and flexible *Key Moments:* 00:00 Intro 03:20 Growing Up With An Entrepreneur And Why That Matters Later In Business 12:45 How Kasey Found Nutrition Through Family Health And Personal Experiences 26:10 The Reality Check Of Clinical Nutrition And Knowing When To Pivot 39:30 Eating Healthy When Life Is Busy And Meal Prep Feels Impossible 54:05 The Truth About Diet Culture And Why Quick Fixes Keep Failing People 01:08:40 Protein Hype Vs What Your Body Actually Needs More Of 01:28:15 Letting Go Of Food Guilt And Why Sometimes You Just Eat The Muffin ABOUT KASEY STROUSE: Registered dietitian and an Iaedp Approved Certified Eating Disorder Specialist - Consultant/Supervisor Learn more about Kasey and connect at https://www.normallynourished.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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You can work your tail off… and still lose money in your “dream job.” That’s the uncomfortable realization Michele Williams had after years of doing work she loved, only to discover she wasn’t actually charging for the most valuable part of it: her thinking. When I sat down with Michele, a two-time founder and the force behind Scarlet Thread Consulting and Metrique Solutions, we unpacked how that moment changed everything. She grew up in a blue-collar mill town where you figured things out instead of hiring experts. That scrappy mindset helped her build businesses, but it also led to underpricing, overworking, and way too many spreadsheets. We talk about why “charge what you’re worth” misses the point, how businesses will gladly take every ounce of your time if you let them, and why your strategy and financials have to line up if you want profit and a life. If you’ve ever said yes too quickly or felt busy but not profitable, this conversation will feel uncomfortably familiar, in a good way. *What Comes Up When Consultants Talk Shop:* 📊 How Michele’s scrappy upbringing shaped her instinct to figure it out first and charge later 📊 The moment she realized she was losing money in her dream job—and why it forced a major pricing shift 📊 Why “charge what you’re worth” is bad advice (and what to focus on instead) 📊 The hidden mistake most consultants make when pricing work that comes easily to them 📊 How spreadsheets went from a helpful tool to a full-blown nightmare—and sparked the creation of a SaaS platform 📊 Why data for data’s sake is useless without a clear strategy and life goal behind it 📊 How to stop letting your business consume all your time, energy, and attention 📊 The importance of building a business that supports your life—not one you need to escape from 📊 Why profitability, planning, and joy actually do belong in the same conversation *Key Moments:* 00:00 Intro 02:30 Scrappy Roots And Growing Up In A Fix-It-Yourself Town 11:45 The Early Hustles And Saying “Sure, I’ll Do It” Before Knowing How 24:10 The Moment She Realized She Was Losing Money In Her Dream Job 37:50 Why “Charge What You’re Worth” Never Sat Right With Her 52:20 When Data Stops Being Helpful And Starts Getting In The Way 1:06:40 Building A Business That Supports Life Instead Of Consuming It 1:22:15 Using Numbers To Think Forward Instead Of Judging The Past ABOUT Michele Williams: Scarlet Thread Consulting and Metrique Solutions Learn more about Michele, and connect at https://www.scarletthreadconsulting.com and https://www.metriquesolutions.com IG - @scarletthreadatl, @Metrique Solutions Facebook – Scarlet Thread Consulting, Metrique Solutions LinkedIn - https://www.linkedin.com/in/michele-williams-business-coach/ 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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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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