Scrappy but Successful [Consultant's Personalities When No One's Watching]
This isn't your typical business podcast. It's a business-and-comedy crossover for consultants, fractional CFOs, advisors, and service-based entrepreneurs who are building real consulting businesses. We talk entrepreneurship, make jokes, and actually enjoy the conversation. We start with where our guest came from, dig into the early (often messy) days of their career, and unpack how their personality shows up in their business today — from client relationships and boundaries to pricing decisions and growth strategy. We'll determine whether they're scrappy or sophisticated through a series of fun stories and rapid-fire questions that reveal how they really operate behind the scenes. Along the way, we pull random questions, laugh at corporate nonsense, solve an actual data or analytics problem, and get to know their business in a way they've never described it before. You'll hear real conversations about consulting challenges, scope creep, decision-making, and how data-driven thinking supports smarter business growth. No fluff. No canned answers. Just fun, genuine conversation, with a dash of entrepreneurial lessons you can actually apply to your own consulting business. Because people listen more when you're having fun. And people do business with people they actually like. 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.
Episodes
What happens when a self-proclaimed lazy kid who once walked out of high school ends up running an award-winning IT company? That is exactly what Isaac Alexander unpacks in this conversation.
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...
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 ...
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 Matriek Solutions, we unpacked how that moment cha...
Jack pulls up a chair with Cassandra D'Alessio, founder and Chief Content Strategist at Next Page Brand Strategies, for a conversation that proves most successful consulting businesses don't start polished; they start scrappy.
Cassandra shares how growing up constantly moving, working early retail jobs, navigating teaching, corporate life, and eventually launching her own business all built the adaptabilit...
This isn't your typical business podcast.
It's a business-and-comedy crossover where we talk entrepreneurship, make jokes, and actually enjoy the conversation. We start with where our guest came from, dig into the early (often messy) days, and unpack how their personality shows up in their business today.
We'll determine whether they're scrappy or sophisticated through a series of fun stories.
Along the wa...
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