Scrappy but Successful [Consultant's Personalities When No One's Watching]
By Pineapple Jack
Categories: Business, Entrepreneurship, Management
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.
67 episodes indexed on podsearch.
Recent episodes
- 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…
- 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…
- 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…
- 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…
- 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…
- 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…
- 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…
- 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…
- 58. Reality Is Undefeated: Lessons from Six Exits with Russ Sorrells
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…
- 57. From Metal Bands to Legal Marketing: The LegalFenix Story with Ron Latz
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…
- 56. Space Robotics to Strategic Advisor with Katie Bedford
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…
- 55. Fractional CSO Secrets from Chief Outsiders with Aaron Gutowski
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…
- 54. Nine Revenue Streams and One Referral Rule with Tina Ruark-Baker
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…
- 53. The Accidental Salesman Who Won Over Chick-fil-A with John Buckner
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…
- 52. Six Months on the Floor, Then a Business with Jocelyn Singer-Sargent
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…
- 51. Lawyer, Auditor, Fractional CFO: The Scrappy Path with Rob Bankey
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…
- 50. The NFL, Wall Street, Hollywood, and The Standard with Cris D'Annunzio
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…
- 49. Turning Donor Gifts Into Loyalty That Lasts with Alison Jeffrey
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…
- 48. From Goldman Sachs to Fractional CFO for Small Business with Oscar Casanova
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…
- 47. From Homebuilder to Fractional CFO: 30 Years of Scrappy Lessons with Mark Dunaway
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…
- 46. Blind Spots, Business Therapy, and the Art of Scrappy Leadership with Sean McColl
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…
- 45. From CNC Shops to Saudi Royalty: How Minds on Fire Got Here with Marcus Gaughan
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…
- 44. From Tornado to Thriving Agency with Priscilla McKinney
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 on the show's central question: you personally have to be scrappy, but your…
- 43. Stop Chasing Leads and Start Generating Clients with Lindsey Wagnon
Lindsey Wagnon left a thriving corporate marketing career in 2019 to build Lindsey Wagnon Marketing, and she has spent the years since helping small and mid-sized businesses break through what she calls the "Valley of Death" - the revenue plateau that stalls so many founders. In this episode, Jack…
- 42. Why Your Money Mindset Is Costing You Six Figures with Joel Salomon
Joel Salomon spent years managing hundreds of millions of dollars on Wall Street, including a stretch at Citigroup where he generated positive returns in 2008 while the market fell 40%. Today he's a Prosperity Coach known as "The Money Doctor," helping heart-centered entrepreneurs (yoga teachers…
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