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

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.

  1. 4 days ago

    66. From Sewing Jeans at 10 yrs old to Building a Blue Collar AI Agent with Sandra Carlisle

    Sandra Carlisle has been an entrepreneur since she was 10 years old, hemming pants and lining a customer's jeans with flannel. From there she cleaned houses on a moped, built and sold a cleaning company called Maid in Philly, earned five FINRA licenses, and served as a chief compliance officer at Nationwide Financial. Today she's the founder of Wealthy Palette, a business operations and brand marketing firm for founder-led trade businesses. In this episode, Sandra and Jack dig into Vera, her AI voice agent that answers calls, books jobs, and drops every lead into a CRM for contractors who are on a roof or under a sink when the phone rings. Sandra breaks down her 5-gear Authority Operating System, why every business should be built to be sold, how she accidentally invented value-based pricing as a teenager, and how she went from ketchup sandwiches in a studio apartment to owning 32 acres in Tioga County. Verdict: 100% scrappy. Chapters: 0:00:00 Intro - scrappy or sophisticated? 0:01:50 Growing up in North Jersey and sewing at age 10 0:04:28 Wealthy Palette and the birth of Vera 0:09:10 The meatball call - stress-testing an AI agent 0:11:44 Call recordings, alerts, and the CRM contractors don't have 0:13:57 Cleaning houses on a moped and Maid in Philly 0:15:53 From FINRA licenses to chief compliance officer 0:19:09 Systems, SOPs, and building a business you can sell 0:26:14 Finding the right ICP and the 5-gear Authority Operating System 0:33:18 Ketchup sandwiches, 32 acres, and what's next Connect with Sandra: LinkedIn: https://www.linkedin.com/in/sandra-carlisle/ Website: https://wealthypalette.com/ VERA: https://veraresponsehq.com/ Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

  2. 18 Oct

    65. Why Independent CPA Firms Should Think Twice About Private Equity with Erin Daiber

    Erin Daiber is the founder and CEO of Well Balanced Accountants, a boutique consulting firm staffed entirely by people with accounting and finance backgrounds. She helps independent CPA firms (roughly $2M to $50M in revenue) free up capacity, build firm value, and stay independent. She is also a CPA and certified coach who started in audit at EY, spent time as an in-house financial analyst, and then went out on her own after burning out as a high-performing accountant. In this episode, Erin takes us from a Cleveland family tool company (and a grandmother who kept money in the linen closet) to coaching paying clients from her car in a parking lot at lunch. We dig into the professor who talked her into accounting, why so many CPAs end up "recovering," what she wildly overthought in the early days, and why she believes the profession needs small and mid-sized firms to stay independent instead of selling to private equity. She also shares why AI without a strategy is just another subscription, and she takes on the scrappy vs. sophisticated lightning round, where she finds out if the data agrees with her. Chapters: 0:00 Welcome and the scrappy vs. sophisticated question 2:08 Growing up in a family tool company 6:02 What Well Balanced Accountants does today 8:08 From graphic design to accounting 13:49 Burnout at EY and the "recovering CPA" problem 19:34 Coaching from a parked car to starting a business 23:16 Finding the niche and what she overthought 31:01 Why independent firms should stay independent 35:14 AI strategy and the capacity diagnostic 42:31 Scrappy vs. sophisticated lightning round Connect with Erin: Well Balanced Accountants: https://wellbalancedaccountants.com LinkedIn: https://www.linkedin.com/in/cpacoacherin/ Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

  3. 11 Oct

    64. How a Marketer Ended Up Selling Spray Drones to NASA with Aruna Inalsingh

    Is Aruna Inalsingh successful because she's sophisticated or because she's a little bit scrappy? Jack sits down with the fractional CMO and founding member of TerraNav Spray Drones to find out. Her first answer is that it's all relative, which fits a conversation that ends up on the moon. Aruna explains what a spray drone actually is, how an engineer turned marketer ended up in agriculture, and what she saw at a NASA conference about drones built for moon base operations. She also shares why she puts process ahead of strategy, how she keeps several businesses moving at once (including a brand-new venture called Life's Guardrails that helps families plan for aging), and where TerraNav is headed as it moves toward manufacturing in Northwest Arkansas. Chapters: 0:00:00 Sophisticated or scrappy? Aruna weighs in 0:02:22 What is a spray drone, and how did a marketer end up here? 0:06:25 Space drones and moon base at NASA 0:08:42 Growing up in Trinidad and Baltimore, plus basement dance shows 0:12:00 Her businesses, including the new Life's Guardrails 0:16:16 Balancing it all: strategy vs. execution in the AI era 0:21:44 People, process, strategy, product: what comes first? 0:27:48 TerraNav's roadmap: Arkansas manufacturing and funding 0:33:27 The verdict: scrappy or sophisticated? Aruna's links: Website: https://terranav.aero LinkedIn: https://www.linkedin.com/in/arunainalsingh YouTube: https://youtube.com/@terranavspraydrones Facebook: https://www.facebook.com/share/1GWT5iMwRm/ Instagram: https://www.instagram.com/terranavspraydrones Jack's links: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

  4. 11 Oct

    63. Ethical Selling Wins: Listening, Calibration, and Human Connection with Sue Barrett

    Is Sue Barrett successful today because she is sophisticated, or because she is a little bit scrappy? In this episode of Scrappy But Successful, Jack Tompkins sits down with the founder and CEO of Barrett Consulting Group and the Selling Better movement, one of Australia's most distinctive voices on ethical, human-centered sales, who has trained over 50,000 professionals across five continents. Sue takes us from school holidays in her father's timber business, where she learned not to be intimidated by skeptical builders, to landing her first $10,000 sale in her first week in business. Along the way she explains why listening and asking better questions beats throwing information at buyers, why most businesses fail to produce content that convinces a buyer to choose them, and how consultants and small business owners can sell more effectively in the age of AI without losing the human connection. Chapters: 0:00 Welcome, an Australian fun fact, and meet Sue Barrett 3:46 Growing up in the family timber business 7:57 Selling with humanity: listening, calibrating, and the 75% content gap 15:43 The double gap: in-person conversations and online presence 19:17 Vendor-neutral matchmaking and the used car salesman problem 21:54 Testing ideas, using AI, and doing your homework first 24:09 Starting out in 1995 and landing the first $10,000 sale 31:41 What Barrett does today: go-to-market, sales process mapping, AI and CRM 33:40 Selling what you have not done yet, and unlearning stage fright 38:52 One tip for more effective selling and where to find Sue Connect with Sue Barrett: Website: https://www.suebarrett.com/ Barrett Consulting Group: https://www.barrett.com.au/ Selling Better: https://www.sellingbetter.com/ Sell Like A Woman: https://www.selllikeawoman.com/ Substack: https://suebarrett.substack.com/ LinkedIn: https://www.linkedin.com/in/suebarrett1/ Connect with Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

  5. 4 Oct

    62. AI Can't Close Your Deals: Selling Into the Trust Gap with Gus Byleveld

    Gus Byleveld is the founder of The Wondering and a former CEO and revenue operator with 25+ years of experience building and leading B2B tech companies. He started out as an architect in Cape Town, South Africa, moved into technology sales, worked through a run of startups, and today helps CEOs of growth-stage tech companies figure out why growth is harder than it should be before they decide what to change. In this episode, Jack and Gus dig into why a sales process should be built from the buyer journey, how AI is changing the way buyers size up sellers, and why the real gap in modern selling is trust. Gus shares the discovery question he swears by, why marketing, BDR, and customer success teams need one shared goal, and why activity is not quality. And the big question: is Gus more scrappy or more sophisticated? Jack's verdict: a dash of scrappiness, backed by some seriously sophisticated thinking. Chapters: 0:00 Scrappy or sophisticated? Meet Gus Byleveld 2:53 From Cape Town architect to tech sales 8:02 The Wondering and why buyer journey beats sales process 14:40 Leaving corporate for a mobile trading card startup 19:18 Two schools of thought on AI, then and now 24:25 The trust gap in modern selling 27:23 The discovery question: what does your world look like when I solve this? 34:29 One shared goal for marketing, BDRs, and customer success 38:16 What makes you uniquely qualified? The question AI can't outsource 43:03 Get out of the building, and where to find Gus Connect with Gus: LinkedIn: https://www.linkedin.com/in/gusbyleveld/ The Wondering: https://thewondering.net/ Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

  6. 4 Oct

    61. Hustle to Engine: Building a Sales Machine Beyond the Founder with Matt Lauro

    Is a fractional CRO scrappy or sophisticated? Matt Lauro, founder of Fractional CRO in Charlotte, NC, joins Jack Tompkins to find out. With more than a decade and a half in workforce solutions and recruitment, Matt helps founder-led companies build a sales and marketing engine that scales beyond the founder's own relationships. In this episode, Matt explains why hiring a VP of Sales is usually the wrong first move, how he prices fractional work with a flat monthly retainer instead of by the hour, where his clients come from (about a third each from referrals, LinkedIn, and his website), and why the client side of the bow tie model is the most overlooked part of revenue growth. Along the way: lemonade stands, stamp collections, a nine-year-old's Pokemon card lesson, and a scrappy or sophisticated lightning round. The final verdict: 80 percent scrappy, 20 percent sophisticated. Chapters: 0:00:00 Intro and the scrappy vs sophisticated question 0:01:43 Growing up scrappy: lemonade stands, stamps, and Pokemon cards 0:06:20 What a fractional CRO actually does 0:07:31 Why hiring a VP of Sales is usually the wrong move 0:11:44 Leaving corporate and launching on the side 0:18:31 Pricing fractional work with a monthly retainer 0:23:26 First clients, credibility, and fractional partnerships 0:31:50 KPIs and the bow tie model 0:34:41 Scrappy or sophisticated lightning round 0:42:23 The book and Substack: From Hustle to Engine Connect with Matt Lauro: Fractional CRO: https://www.fractionalcro.org LinkedIn: https://www.linkedin.com/in/mattlauro/ Connect with Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

  7. 27 Sept

    60. The People and Process Playbook for CPA Firms with Will Hill

    Will Hill spent 21 years at Thomson Reuters helping build the accounting industry's shift toward advisory services, then left to found Will Hill Consults, LLC, where he coaches CPA firm owners one-on-one at the intersection of people and process. With 25+ years in the industry and hands-on work inside 400+ accounting firms, Will has a rare read on why some firm leadership changes stick and most don't. In this episode, Jack and Will talk about why he refuses to do group coaching, the moment he had to tell two employees their jobs weren't going away even though the software was, how firms make the leap from compliance to advisory conversations, and the scrappy roots (golf-ball hustling included) behind his one-on-one approach today. Chapters: 0:00:00 Intro: scrappy or sophisticated? 0:01:37 Growing up in Flint and selling golf balls for cash 0:04:06 Coaching CPA firms at the intersection of people and process 0:06:18 Why he only coaches one-on-one, never in groups 0:08:12 From janitor and bank teller to 21 years at Thomson Reuters 0:11:38 Asking real questions and earning client trust 0:17:17 Moving firms from compliance to client advisory services 0:20:34 Leaving Thomson Reuters to launch his own consulting firm 0:26:40 Finding his ICP, firing bad-fit clients, staying collaborative 0:35:13 Scrappy vs sophisticated lightning round Will Hill: Website: https://willhillconsults.com/ LinkedIn: https://www.linkedin.com/in/wghill/ Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

  8. 19 Sept

    59. Why She Never Took a Client Outside CPG with Abby June Richards

    Abby June Richards is the founder of The CPG CFO, a fractional CFO firm helping emerging, better-for-you and sustainable CPG brands know their numbers and build businesses that last. She spent 15 years in operations before becoming a CPA, then nearly 7 years at RSM across audit, outsourced accounting, and tech implementation, before launching her own firm in 2023 focused exclusively on CPG brands in the $0-50M range. In this episode, Jack and Abby trace her path from being homeschooled as the oldest of six kids in South Texas (where she was literally running a ledger for a game of Little People) to watching her dad's engine-rebuilding business slowly fail, to finally taking the leap and starting her own firm with zero clients. She breaks down her CASH FIGHT framework for CPG cash flow, gets real about the fear and doubt in year one, and explains why she stayed locked into her niche even when easier work was on the table. Chapters: 0:00 Intro and the sophisticated vs scrappy question 3:09 Homeschooled in South Texas as the oldest of six 9:34 What The CPG CFO does for clients today 12:51 College, community college advocacy, and the CPA path 18:41 Early jobs, her dad's failed business, and the leap to starting her own firm 22:07 Zero clients and posting on LinkedIn for 600 days 24:22 Landing the first client and locking in her ICP 28:05 Cash flow, contracts, and the CASH FIGHT framework 35:30 Lightning round: scrappy habits and money mindset 37:25 Branding, the logo, and inside her home office The CPG CFO: https://www.thecpgcfo.com Abby's LinkedIn: https://www.linkedin.com/in/abbyjuner/ The CPG CFO on Instagram: https://www.instagram.com/thecpgcfo/ The CPG CFO on YouTube: https://www.youtube.com/@TheCPGCFO LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

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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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