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

Pineapple Jack
  • 5.0 (1)
  • Entrepreneurship
  • Updated Weekly

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.

  1. 21. The 80/20 Rule That Will Change How You Look at Your Clients with Scott Peterson

    9h ago

    21. The 80/20 Rule That Will Change How You Look at Your Clients with Scott Peterson

    Scott Peterson walked onto the Oregon State basketball team by leaving messages on the coach's home phone until someone called back. He started his sales career bribing his way into meetings with Dunkin' Donuts. He launched his consulting firm in 2014 with a non-compete, no local network, and a city he barely knew. And somewhere in all of that, he built one of the most practical, data-driven sales frameworks for founder-led businesses you'll hear about. Scott is the founder of Carver Peterson Consulting and author of "Beyond the Founder Rainmaker." This one's got hustle, hoops, and hard-won sales truth from someone who has lived every chapter of it. Chapters: 00:03 - Welcome and intro - Scott rates himself as scrappy 00:58 - Growing up in Corvallis, Oregon - a dad who built custom homes and client relationships at the dinner table 03:49 - College, Oregon State, and the walk-on story - cold calling the coach until the callback came 07:14 - Moving to Boston cold and landing a career at Aerotech 10:10 - What Carver Peterson does and who Scott helps - the Founder Rainmaker problem explained 14:06 - Getting the first client and building the network from scratch in Chicago 18:17 - ICP evolution - how "anyone who needs sales help" gets you nowhere 20:52 - Scrappy marketing moves - donuts, dollar drafts, and freezing shorts in Boston 26:45 - Proving value to clients - data-first, scorecards, and the Revenue Compass Assessment 30:36 - Breaking out of the founder stall - two types of Founder Rainmakers and how to serve each 34:52 - The 80/20 client revenue distribution - the jaw-dropper data cut that changes strategy 37:27 - Lightning round - sports cards, steak dinners, inbox zero, and getting sassy with AI 47:09 - "Beyond the Founder Rainmaker" and what Scott is looking for next Connect with Scott: https://www.carverpeterson.com/ https://scott-ynirvf8i.scoreapp.com/ https://www.linkedin.com/company/carver-peterson-consulting-llc https://www.linkedin.com/in/carverpeterson/ Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

    48 min
  2. 20. Scrappy by Design: How an Anthropologist Became the World's Innovation Storytelling Expert with Susan Linder

    6d ago

    20. Scrappy by Design: How an Anthropologist Became the World's Innovation Storytelling Expert with Susan Linder

    Susan Linder is not your typical consultant. A cultural anthropologist from the Bronx who hitchhiked through Central American war zones, trained as an AIDS epidemiologist, and stumbled into PR on a blind date, she has spent 30 years proving that the right story - told the right way - changes everything. Today she is the Founder and CEO of Innovation Storytellers and recognized as the world's leading expert on innovation storytelling. Jack and Susan trace her path from answering her dad's tool-sales phone at eight years old to working in Thai brothels in the 1990s and eventually helping Fortune 100 companies like GE, AT&T, and Citi win funding, drive acquisitions, and get their breakthrough ideas across the finish line. Along the way: why fear is a terrible long-term motivator, what it actually means to be the hero of your own story, and why innovation teams keep getting their credit stolen. Chapters: 00:00 - Introduction and the koala fingerprint fun fact 00:48 - Scrappy roots: immigrant parents, a station wagon full of tools, and the family business 05:00 - Sitting with the adults: growing up curious and always interviewing 08:00 - Phones, orders, and selling at eight years old 09:00 - Flea markets, freelance gigs, and financing college yourself 13:00 - Discovering cultural anthropology by accidentally inventing it 16:00 - Junior year abroad and hitchhiking through Central American war zones 22:00 - Thailand, HIV, and the storytelling insight that changed everything 29:00 - From the CDC to a blind date with a Forbes editor to the PR world 34:00 - Building Innovation Storytellers: the scrappy evolution from Lotus to today 37:00 - Helping innovation teams pitch the Joint Chiefs, the CFO, and everyone in between 39:00 - Lightning round: ChatGPT jokes, inbox zeros, and the font formatting confession Connect with Susan: https://www.innovationstorytellers.com https://www.linkedin.com/in/susanjlindner/ https://www.instagram.com/innovationstorytellers/ https://www.youtube.com/channel/UCId9xpyIaSwD25Z9ZsiZ3-g https://www.facebook.com/InnovationStorytellers Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

    48 min
  3. 19. The 6-Part Marketing Engine Every Indie Game Studio Needs with Jay Rooney

    May 28

    19. The 6-Part Marketing Engine Every Indie Game Studio Needs with Jay Rooney

    Jay Rooney is the founder of Spawn Point Marketing, a fractional CMO practice for indie and AA game studios, and the publisher of Game & Word - an award-winning Substack examining video games through interdisciplinary academic lenses. In this episode, Jay breaks down why most indie studios are invisible at launch (hint: they started marketing too late), walks through his 6-component Functional Marketing Framework, and shares the scrappy story of how he grew a mobile game from zero to hundreds of thousands of users without a single dollar in ad spend. Plus: the high school vending machine protest campaign that started it all. Chapters: 00:00 - Intro and fun fact: the AI personalities of Pac-Man ghosts 01:00 - Scrappy or sophisticated? Jay makes his case 01:40 - Growing up between New Orleans, Mexico City, and Miami 03:43 - Life with a foot in two worlds - and the entrepreneurial spark it lit 04:46 - The high school vending machine protest campaign 08:14 - Grades, curiosity, and learning how to think vs. what to think 10:05 - Game & Word: examining games through interdisciplinary academic lenses 14:49 - The $200B gaming industry and why discoverability is the real crisis 15:34 - The 6-component Functional Marketing Framework for indie studios 22:33 - How to get content creators to notice your game (the scrappy way) 27:34 - Wishlist momentum, revenue projections, and getting data-driven 29:25 - Favorite games growing up: Final Fantasy VII, Zelda, and Earthbound 31:37 - The founding of Spawn Point Marketing - sink or swim 36:48 - Getting first clients through inbound only (no cold outreach) 38:36 - Lightning round: desk setup, inbox chaos, and 63,403 unread emails 42:56 - What makes Jay feel sophisticated: buying the house and signing the office lease 43:43 - Three takeaways: start early, stay consistent, own your marketing 48:38 - Where to find Jay and the June 9 webinar Spawn Point Marketing: https://spawnpointmarketing.com Launch Readiness Scorecard: https://scorecard.spawnpointmarketing.com SPM Substack: https://spawnpointmarketing.substack.com Game & Word Substack: https://gameandword.substack.com Jay's Webinar (June 9): https://www.eventbrite.co.uk/e/building-a-marketing-engine-for-your-game-without-a-cmo-tickets-1988318245396?aff=jay Jay on LinkedIn: https://www.linkedin.com/in/jayrooneysf/ https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

    50 min
  4. 18. Why 45,000 Australian Business Owners Walk Away With Nothing with Eric Tjoeng

    May 25

    18. Why 45,000 Australian Business Owners Walk Away With Nothing with Eric Tjoeng

    Eric Tjoeng grew up in Indonesia in a family of seven entrepreneurs, started his first business venture at age 12 promoting a comedy show, and eventually moved to Australia to build a career starting at Deloitte. After 20+ years in senior executive roles at multinationals - including GM of a $1.4B automotive group - he founded Business Growth and Exit Specialists (BGES) in Sydney, where he now helps small and medium businesses grow strategically and exit successfully. He's 100% sophisticated, and the data agrees. Chapters: 00:00 - Intro and Australia Fun Fact: The Dingo Fence 01:11 - Scrappy or Sophisticated? Eric's Answer 02:45 - Growing Up in Indonesia with 7 Entrepreneurs 05:28 - Age 12 Comedy Show Promoter and First Investment 07:14 - Deloitte, Multinationals, and the SME Shift 10:34 - Why SME Owners Work Hard But Don't Get Returns 13:27 - The Dashboard Formula and Data-Driven Strategy 17:35 - Founding BGES and Getting That First Client 25:40 - The Australia Exit Crisis: 200K Exits, 45K Walk Away With Nothing 31:10 - The BGES Exit Formula and Business Valuation 38:44 - Speed vs. Strategy - Eric's Answer 40:27 - Lightning Round: Inbox, Celebrations, and Vetting Clients 43:39 - Final Verdict: 100% Sophisticated Guest Links: https://www.linkedin.com/in/etjoeng/ https://bges.co Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

    45 min
  5. 17. From Sheep Ranch to Amazon: Mastering the Scrappy-Sophisticated Spectrum with Tina Dao

    May 21

    17. From Sheep Ranch to Amazon: Mastering the Scrappy-Sophisticated Spectrum with Tina Dao

    What does it really take to build a business that creates higher returns AND more joy? Tina Dao, founder of Liberated Leaders, has lived the answer - from baking cupcakes for her dad's hunting camps and negotiating car loans with her grandpa at 17, to leading operations at Amazon, Fitbit, and Walmart before launching her own fractional COO firm. In this episode, Tina and Jack dig into conscious capitalism, the "silver tsunami" of business transitions, why the trades are safer than college right now, and how to know when your company needs to move between scrappy and sophisticated. Chapters: 00:00 - Intro + fun fact: butterflies taste with their feet 00:54 - Scrappy vs. sophisticated: Tina's take on the tension between the two 02:00 - Growing up in Western Colorado with sheep ranchers and serial entrepreneurs 09:04 - First hustles: baking for hunting camps, babysitting, and cleaning houses at 12 13:42 - Negotiating a car loan from grandpa at 17 - with a term sheet 15:32 - A 2.0 GPA, 98s on every test, and why the trades beat college right now 19:06 - US Navy electronics technician to corporate operations 25:32 - Starting Liberated Leaders and the case for conscious capitalism 29:25 - Landing the first client, the family bet, and the real cost of going out on your own 35:15 - Lightning round: scrappy studio, inbox limits, and corporate pet peeves 43:39 - The Liberated Leaders pitch: 5-10x returns, more delight, and the silver tsunami Tina Dao - Liberated Leaders https://www.liberatedleaders.com, https://www.linkedin.com/in/tinaldao/ Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

    48 min
  6. 16. Ending Random Acts of Marketing with a Brand Operating System with Tanner Rankin

    May 17

    16. Ending Random Acts of Marketing with a Brand Operating System with Tanner Rankin

    What happens when a corporate employee discovers Amazon, teaches himself e-commerce, becomes a CMO, and then realizes the whole agency model is broken? You get Tanner Rankin - founder of Source Approach, Referazon, and the Brand Source OS - and a seriously compelling story about turning scrappy roots into a sophisticated operating system for brands. Tanner breaks down how he built the Brand Operating System from a pile of spreadsheets, why most brands fail their agency partners (not the other way around), and what it actually looks like to make marketing predictable and repeatable. If you're tired of random acts of marketing, this one's for you. Chapters: 0:00 - Intro and fun fact 0:52 - Scrappy roots: corporate robot turned Amazon seller 4:07 - The CMO role and the cold hard look in the mirror 12:34 - Building Source Approach and the first Brand OS 19:35 - Entrepreneur ADD, Referazon, and solving the right problems 26:09 - Fake it till you make it and the MVP trap 30:44 - Who Source Approach serves today 33:06 - The woodsman in a suit: office tour and lightning round 45:42 - KPIs, client success, and what makes marketing repeatable Connect with Tanner: Website: https://www.sourceapproach.com Personal site: https://www.tannerrankin.com LinkedIn: https://www.linkedin.com/in/tannerrankin/ Referazon: https://www.referazon.com Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

    49 min
  7. 15. 3-Step Framework for Growing Home Service Businesses with Phil Risher

    May 10

    15. 3-Step Framework for Growing Home Service Businesses with Phil Risher

    Phil Risher didn't have entrepreneurs in the family - he had a single mom, a pest control dad, a rap career in high school, and eventually a school bus he lived in while figuring out his next move. Somehow it all led to Phlash Consulting, a 22-person marketing and data firm that grew home service businesses an average of 27% last year. In this one, Jack and Phil trace the full origin story - from selling autographed CDs out of a backpack to managing a $300K/month Enterprise branch at 25, to quitting corporate on his honeymoon and building something entirely his own. Topics covered: 0:00 - Intro and fun fact - the most expensive pineapple in history 0:52 - Scrappy vs. sophisticated and Phil's honest opening take 1:16 - Growing up outside DC, immigrant hustle, and the high school rap career that launched it all 7:36 - Ruby Tuesday's, commission brain, and the first real entrepreneurial unlock 8:22 - Geneva College, three majors, studying abroad in Rome and China, and $30K in student loans 10:12 - Paying off debt in 12 months, buying a condo at 25, and building zero-debt infrastructure 12:04 - Enterprise Rent-a-Car, the BMI report, and running a $300K/month branch on data alone 17:47 - The school bus trip, the duck cleaning company, and when all the worlds collided 22:08 - The three levers every home service business needs: marketing, data, and automations 25:15 - The growth thresholds - systems to 3M, data to 5M, people to 10M 27:15 - How Tom fired Phil to set him up, the name Phlash, and the private equity framework that built the whole business 35:28 - Profit First, abundance mindset, and leading a team with a vision big enough for everyone 38:13 - Minimalist office, 100% on or off, and making the Inc. 5000 Best Workplaces list Connect with Phil Risher: https://phlashconsulting.com https://www.linkedin.com/in/philrisher/ https://www.instagram.com/philrisher/ Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

    45 min
  8. 14. The Body Keeps the Score in Business with Elizabeth Rose

    May 4

    14. The Body Keeps the Score in Business with Elizabeth Rose

    Elizabeth Rose is President and Lead Coach at Garth Rose Consulting Group, where she brings 27 years of mediation experience and a decade of executive coaching to leaders and teams. But before the polished practice, there was a VW camper rolling through Europe, a Starbucks apron, and a borrowed conference room. Elizabeth's path from Long Island to law school to barista-turned-mediator is one of the scrappiest origin stories we've had on the show - and her work is as rigorous as her roots are "ready, fire, aim." In this episode, Jack and Elizabeth dig into somatic experiencing (yes, your body is keeping score), why emotional intelligence is the real ROI lever for your sales team, and why great leadership now means admitting when your two-year-old kept you up all night. Chapters: 00:00 - Intro + Fun Fact: Mangoes Rule the World 01:22 - Long Island Roots and an Accidentally Wild Upbringing 07:01 - Senior Year of High School in Hong Kong 10:47 - From Retail Buyer to Stay-at-Home Mom to Law School With Three Kids 13:14 - Three Months as a Lawyer, Then the Pivot to Mediation 15:04 - Getting Her First Client as a Starbucks Barista 16:43 - Building a Practice Out of a Borrowed Conference Room 22:32 - Where Elizabeth's Emotional Intelligence Approach Comes From 24:49 - What Is Somatic Experiencing? 30:21 - The Two-Minute Body Scan: A Practical First Step 34:04 - Somatics in the Boardroom: Executive Coaching in Practice 39:15 - Measuring the ROI of Emotional Intelligence Work 42:10 - Lightning Round: Scrappy vs. Sophisticated   Connect with Elizabeth: https://www.linkedin.com/in/elizabethroseesq https://garthrose.com   Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

    54 min
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Ratings & Reviews

About

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.

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