『Scrappy but Successful [Consultant's Personalities When No One's Watching]』のカバーアート

Scrappy but Successful [Consultant's Personalities When No One's Watching]

Scrappy but Successful [Consultant's Personalities When No One's Watching]

著者: Pineapple Jack
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概要

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.2026 マネジメント マネジメント・リーダーシップ リーダーシップ 経済学
エピソード
  • Ep. 5 When Profit Leaks Hide in Plain Sight with Diane Gardner
    2026/03/16

    What happens when someone who grew up in a tiny mining town of 1,500 people ends up becoming a trusted profit strategist for home service businesses? Diane Gardner's story is a scrappy one. She didn't grow up around entrepreneurs. Her dad worked in the mines and believed in practical skills like learning to drive a manual truck on a hillside before she could ever take the wheel.


    A chance connection with an accountant in her small town set Diane on a path that has now turned into a decades-long career. Today she is a tax strategist, Profit First coach, author, and host of the Profitable Home Services Podcast. She works with contractors and blue-collar business owners who are working hard but want to see more of that effort turn into real profit.


    Along the way we talk about the early days of building a business from scratch, the lessons that shaped her approach to money, and the mindset shifts that help owners build businesses that are not just busy, but truly profitable.

    What Comes Up When Consultants Talk Shop:

    • Growing up in a tiny mining town, and how a chance connection led Diane into accounting

    • The scrappy early years of entrepreneurship, from ramen noodles to door-to-door client hunting

    • Why many hardworking business owners still struggle to turn revenue into real profit

    • The hidden "profit leaks" quietly draining home service businesses

    • Why the classic December spending spree is terrible tax planning

    • Creative tax strategies most small business owners have never heard about

    • How the Profit First system changes the way businesses manage cash flow

    • Simple ways to generate more revenue from existing customers instead of chasing new ones

    • How Diane helps blue-collar business owners become wildly profitable and proud of it

    ABOUT Diane Gardner:

    • Your Profit & Tax Coach

    • Host of the Profitable Home Services Podcast

    • Learn more about Diane and connect at https://profitcoach4you.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 comes 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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    48 分
  • Ep. 4 The Raving Fans Playbook For "Boring" Businesses with Isaac Alexander
    2026/02/19

    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 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.

    You will hear how he reframed a "commodity" IT business into a customer service company with standards that actually move the needle. We also touch on succession, acquisition goals, and the systems behind sustainable growth. It is a practical look at what happens when scrappy ambition meets intentional structure.

    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

    • Why anxiety hit hard during rapid growth 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"

    • The 15-minute response standard that crushed industry averages

    • Why most MSPs lose clients without realizing it and how to make switching frictionless

    • How EOS scorecards and forward-looking KPIs prepare you to acquire another business

    • What it really means to dream big enough that your team's goals fit inside yours

    • The scrappy traits Isaac still carries today and the sophisticated systems he had to build around them

    ABOUT ISAAC ALEXANDER:

    • President of Quo Vadis Inc.

    • 13 years in the mortgage industry

    • https://quo.cc/

    • https://www.linkedin.com/company/quovadis-it

    • https://x.com/QuoVadisInc

    • Charlotte's Best Award Winner

    • Award celebration

    • https://www.facebook.com/people/Quo-Vadis/61578842335195/#

    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 comes 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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    45 分
  • Ep. 3 The Shift From Diet Rules To Real-Life Nutrition with Kasey Strouse
    2026/02/19

    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

    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/

    • Instagram: @normallynourished

    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 comes 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.

    続きを読む 一部表示
    49 分
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