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business
Hosted by Pineapple Jack · business · EN-US · 66 episodes
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 su
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Contact path
Verified email
Booking probability
33%
Guest openness
Selective
Sign up to generate a grounded pitch for Scrappy but Successful [Consultant's Personalities When No One's Watching].
Signup to Generate a PitchThis 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.
Scrappy but Successful [Consultant's Personalities When No One's Watching] is hosted by Pineapple Jack. The show has published 66 episodes to date.
Recent episodes include "64. How a Marketer Ended Up Selling Spray Drones to NASA with Aruna Inalsingh" (11 October 2026, 35 minutes), "63. Ethical Selling Wins: Listening, Calibration, and Human Connection with Sue Barrett" (11 October 2026, 41 minutes), and "62. AI Can't Close Your Deals: Selling Into the Trust Gap with Gus Byleveld" (4 October 2026, 46 minutes).
Scrappy but Successful [Consultant's Personalities When No One's Watching] publishes roughly weekly, with episodes averaging 44 minutes across 66 episodes.
Booking probability for Scrappy but Successful [Consultant's Personalities When No One's Watching] is 33%, and the host is rated Selective on guests. Scrappy but Successful [Consultant's Personalities When No One's Watching] requires a Pod Score of 80 or higher. Scrappy but Successful [Consultant's Personalities When No One's Watching]'s contact route on record: verified email.
The strongest fits for Scrappy but Successful [Consultant's Personalities When No One's Watching] are Business & Management Consulting. Scrappy but Successful [Consultant's Personalities When No One's Watching] has a business audience.
Pineapple Jack hosts Scrappy but Successful [Consultant's Personalities When No One's Watching], a business show with 66 episodes published.
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Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
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...
Scrappy but Successful [Consultant's Personalities When No One's Watching]
Priscilla McKinney is the CEO ("Momma Bird") of Little Bird Marketing, a LinkedIn influencer, a trained cultural anthropologist, and the host of her own podcast, 450-plus episodes deep. She joins Jack to unpack her take...
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