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
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 abo...
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 ...
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 a...
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 fr...
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...
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 episod...
Russ Sorrells has bought, built, and sold six businesses, starting with a machine shop he ran out of his garage as a 21 year old with one electrical outlet and a rotary phase converter that sounded like it was going to take off. Today he is the founder of Beyond the Grind, a certified Pinnacle Business Guide who helps owners get out of the weeds so their teams can actually thrive.
In this episode Russ trac...
Ron Latz is the founder of LegalFenix, a fractional CMO and marketing advisory firm that works exclusively with law firms. After more than 15 years in legal marketing, including stints at FindLaw and Mockingbird Marketing, Ron built LegalFenix into a vendor-neutral shop that helps firms sort out what is actually working in their marketing and what is not.
In this episode, Ron and Jack cover Ron's path from a metal band and umpiring...
Katie Bedford spent seven years as an aerospace engineer building space robotics before pivoting through digital agencies, project management, and five years as a fractional COO to land where she is today: a strategic advisor and thinking partner for agency leaders. She's the founder of K Bedford Consulting in Vancouver, and her whole approach is built on giving business owners the honest, unbiased conversation they can't get from ...
Aaron Gutowski is a Partner and Chief Sales Officer at Chief Outsiders, an "Executives-as-a-Service" firm that places fractional CMOs and CSOs inside mid-market companies. He was one of the first CSOs to join the firm, and he brings more than 20 years of sales leadership experience across data, research, and industrial services to every engagement.
In this episode, Aaron traces his sales instincts back to a Detroit News paper route...
Tina Ruark-Baker has already built and sold two companies, spent two decades climbing to the C-suite, and then walked away from the corner office to start a third business from scratch. Today she runs TRB Creative, coaching small businesses, entrepreneurs, and nonprofits on the one channel she believes almost nobody uses correctly: LinkedIn.
In this episode, Tina and Jack trace her path from a staffing company she started at 18 in ...
John Buckner is the founder of Insightful Selling and a Fractional VP of Sales advisor at Sales Xceleration, bringing a thirty-year corporate sales and marketing career to small businesses that need to grow. His resume includes DuPont, Chick-fil-A, 7-Eleven, Walmart, and Home Depot, but John calls himself an "accidental salesman" - his path started on his father's land surveying crew in the North Carolina foothills, not a sales flo...
Jocelyn Singer-Sargent is the founder of Jocelyn Singer-Sargent Consulting, known as "the work whisperer." She's an HR consultant, coach, and speaker based in Santa Fe, New Mexico, dual-credentialed as a Licensed Clinical Social Worker and a SHRM-certified HR professional. Her practice spans fractional HR leadership, manager training, employee engagement, and coaching for leaders who want to build people strategies that actually wo...
Rob Bankey is the founder of Bankey & Co., a Washington, DC fractional CFO and transaction advisory practice serving growth-stage SaaS, fintech, and AI companies. He led Contactually through its acquisition by Compass and steered Opower through its NYSE IPO before Oracle bought the company, and in 2023 DCA Live named him one of DC's Tech CFO Stars.
In this episode, Rob and Jack trace his path from an Arthur Andersen offer that ...
Cris D'Annunzio believes the greatest enemy of performance isn't failure, it's drift. He's the founder of Mettle & Method, and his resume reads like four different careers stitched together: NFL player, Wall Street broker, Hollywood actor, and high performance sales coach. Along the way he built "The Standard," a philosophy built on a simple idea: everything decays without deliberate maintenance, so you measure where you are, s...
Alison Jeffrey is the founder of Alison Jeffrey Consulting, a fundraising strategy practice working exclusively with nonprofits. After 25+ years in the sector, including years spent in-house, she left a permanent role five years ago to build a boutique consulting practice, working deeply with about 15 clients instead of chasing volume. On this episode, Alison and Jack dig into what it actually means to ask people for money for a li...
Oscar Casanova is the founder of Eververdant Growth Partners, a fractional CFO advisory firm helping lower middle-market business owners make sharper financial decisions. Before starting his own firm, Oscar closed over $30 billion in deals across Goldman Sachs, high-growth startups, and Shopify - and he brings that same rigor to the small businesses that make up the backbone of the economy.
In this episode, Jack and Oscar dig into ...
Mark Dunaway spent 30+ years leading finance and operations for some of the country's top residential homebuilders - and then walked away from all of it to build a fractional CFO market from scratch on the Gulf Coast. As Area President and Fractional CFO for FocusCFO, he covers coastal Alabama and Pensacola, FL, a territory with zero prior FocusCFO presence and a market that often can't distinguish a CFO from a CPA. In this episode...
Sean McColl is the founder of Trusted Business Advisors in Charleston, South Carolina. After more than 20 years as a top-performing sales leader - selling pagers in Washington, DC during the crack epidemic, building accounts at AT&T, and growing a promotional products company from a tiny startup to a successful acquisition - he went independent as an outside advisor. Today he works with owners, successors, and key leaders to br...
Marcus Gaughan started his entrepreneurial journey at 19 with a portable eye therapy device that nearly launched with Iris as a strategic partner - until a single email ended it all. From there he built Minds on Fire through incubators, a CNC manufacturer marketplace, and a pandemic-era pivot that took him from Southern Ontario to investor conferences in the Middle East - picking up a client who happened to be the son of the govern...
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