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

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

By: Pineapple Jack
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 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 Economics Leadership Management Management & Leadership
Episodes
  • 12. From the Mug Bug to CX Expert - The Scrappy Path of Ryen Salo

    12. From the Mug Bug to CX Expert - The Scrappy Path of Ryen Salo
    Apr 26 2026
    Ryen Salo is the Client Experience Manager at CherryBecker, a 10-year CX veteran, Association for Accounting Marketing (AIM) board member and speaker, Finnish sauna enthusiast, and self-described "one and fun" mom living just outside Portland, Oregon. In this episode, Ryen takes us from selling candy and running a seven-dollar blackberry stand in Grants Pass, to driving a 50-mph Mug Root Beer VW Bug for Pepsi Cola, to dropping in and out of college for years before finally finishing her degree through an adult completion program - all while working full-time and being newly married. She breaks down what client experience actually requires (spoiler: it's curiosity), why you have to stop making it about yourself, and why she and Jack are both speaking at the AIM Summit in Palm Springs this May. In this episode: 00:00 - Intro and the bell pepper bump fun fact you will never forget02:42 - Growing up scrappy in Grants Pass, Oregon and a mom who quietly ran the school08:15 - Learning differently, the teachers who really saw her, and why grades don't tell the whole story11:21 - Raising her son in a Title I school and celebrating neurodiversity in 202516:06 - The winding college road - Eugene to California to Portland, food stamps, and finally finishing18:50 - Driving the Mug Bug - Pepsi Cola's 50-mph soda car and sampling at events26:46 - Working at The Climb (while not outdoorsy at all) and winning the guac off two years running28:50 - What client experience actually requires - curiosity, listening, and getting out of your own way33:28 - The CX partnership philosophy - becoming an extension of the client's team35:45 - The Jefferson Memorial and the five whys - how Jack and Ryen both think about root causes37:20 - AIM (Association for Accounting Marketing) and what to expect at the Palm Springs summit42:28 - Lightning round - airports, inbox philosophy, JBL earbuds, and the final scrappy vs. sophisticated verdict Connect with Ryen Salo: LinkedIn: https://www.linkedin.com/in/ryen-salo/AAM (Association for Accounting Marketing): https://accountingmarketing.org/ Listen on: Spotify: https://open.spotify.com/show/3zSMlS41U0FfttadYBYbri?si=f856281edcae4c53Apple Podcasts: https://podcasts.apple.com/us/podcast/scrappy-but-successful-consultants-personalities-when/id1878384628 Connect with Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/Pineapple Consulting Firm: https://www.pineapplecf.comSpeaking: https://www.pineapplejacktompkins.com/YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng
    Show More Show Less
    51 mins
  • 11. From Paper Routes to $2 Billion - The King of Capital Breaks It All Down with Brad Blazar

    11. From Paper Routes to $2 Billion - The King of Capital Breaks It All Down with Brad Blazar
    Apr 20 2026

    What do a $180 driveway shoveling gig, a fake million dollar bill at the Houston airport, and raising over $2 billion in capital all have in common? Brad Blazar. This week on Scrappy But Successful, Jack sits down with the founder of Capital Connections - a knighted speaker, bestselling author, podcast host, and genuinely one of the most interesting people to ever sit across from Jack. Brad breaks down his trademarked philosophy "Beliefology," the psychology behind raising capital without desperation, and some legendary scrappy moves that prove you don't always need a marketing budget - just a Starbucks tab and the right mindset.

    In this episode:

    • (00:03) Intro - Snails, scrappiness, and meet Brad Blazar
    • (01:55) Moving city to city as a kid and becoming a social chameleon
    • (06:51) Paper routes, snow shoveling, and the $180 driveway hustle
    • (10:17) Investing, philanthropy, and why distributions beat W-2 income
    • (16:27) Beliefology - the trademarked philosophy and the story of Jack going from 480 lbs to Men's Fitness cover
    • (20:19) Fear = False Evidence that Appears Real - and why comfort is your worst enemy
    • (24:02) How to raise capital without sounding desperate - slow down, discovery first, pitch last
    • (33:05) The $3 Starbucks strategy that unlocked Dallas's wealthiest doors
    • (40:24) Lightning round - first class, Centurion Lounge, and metal business cards
    • (43:43) The million dollar bill, AirTag luggage hacks, and surviving CrowdStrike Day in flip flops

    Learn more about Brad: https://www.bradblazar.com

    Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Company: https://www.pineapplecf.com Speaking: https://www.pineapplejacktompkins.com/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng
    Show More Show Less
    49 mins
  • 10. The Supply Chain Consultant Who Testifies in Court with Steve Hopper

    10. The Supply Chain Consultant Who Testifies in Court with Steve Hopper
    Apr 13 2026
    Steve Hopper spent years climbing the corporate ladder before a toxic work environment - and a nudge from his wife - pushed him to bet on himself. In 2004, he founded Inviscid Consulting, a supply chain and warehouse operations firm that has since worked with clients ranging from $80B corporations to PE-backed startups. What started as turning over rocks with a small network has grown into 21 years of steady upward trajectory, a thriving expert witness practice across 65-plus legal cases, and a side life as the drummer for the Falls Brothers Band. Steve breaks down exactly how to think about consulting ROI (a client once passed on a 200% return because of the wrong budget bucket), why the mid-market is where the real opportunity lives, and the difference between being accountable and being set up to fail. How a Ben Franklin pros/cons list convinced Steve to turn down a corporate offer and start his own firm in 2004The "authority and accountability relationship" framework Steve teaches every client - and lived through himselfBreaking down the market pyramid: why Steve ignores the top and bottom and focuses everything on the $200M-$2B middleWhy Inviscid has been on 65-plus expert witness cases - and what it actually means to "advocate for the truth" on the standThe $31M jury verdict, 1,000+ documents, and why this work is nothing like the TV versionHow to calculate real consulting ROI - and the auto parts company that wouldn't act on a 6-month paybackLightning round: timewithsteve.com, 4-5 phone numbers (one for band bookings), 100+ unread emails, and Googling someone mid-meeting Chapters: 0:00 - Intro and Fun Fact: Ducks Have Regional Accents1:44 - Growing Up in Charlotte and Atlanta3:40 - The Entrepreneurial Bug and Cub Scout Sales5:23 - Turning Down the Corporate Offer and Taking the Leap7:57 - The Early Days of Inviscid: Turning Over Rocks11:44 - Stability vs. Control: The Real Trade-off of Entrepreneurship14:30 - Authority, Accountability, and Driving Your Own Destiny19:13 - KPIs in Warehousing: From DC-Level to Individual Workers21:08 - The Market Pyramid: Why Steve Focuses on the Mid-Market27:03 - Consulting ROI: The Auto Parts Company That Passed on 200%32:59 - The Expert Witness Practice: 65+ Cases, $31M Verdicts, Advocating for Truth40:14 - Lightning Round: timewithsteve.com, Band Bookings, and Googling Mid-Meeting Guest: Steve Hopper - Founder, Inviscid Consulting Website: https://inviscidconsulting.com Host: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Company: https://www.pineapplecf.com Speaking: https://www.pineapplejacktompkins.com/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng
    Show More Show Less
    51 mins
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