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
Adrian Betts is the founder of Xpandur, where he helps mid-market warehouses unlock hidden capacity and drive profitability without adding headcount, equipment, or new technology. With a background leading high-volume, tight-margin operations, he specializes in eliminating bottlenecks, aligning teams, and turning chaotic warehouse floors into consistently high-perf...
Bill Wilson has built and sold two companies, helped dozens of B2B SaaS founders fix their pricing, and started a brand-new business while walking through a market in southern Spain. He joins Jack to break down why most pricing problems are actually positioning problems, what scrappy founders get wrong about churn math, and how to start a testable company in a sing...
Piyanka Jain has been building AI models since 2002 - before "AI" was a buzzword. Today she's the CEO of AskEnola, an agentic AI platform that automates the entire CFO workflow: closing books, P&L reporting, MRR schedules, and investor reporting - all with high-fidelity output that doesn't hallucinate. In this episode, Piyanka talks about what 25,000 hours of b...
Drew Dowd has built his career walking into broken businesses and finding the one thing everyone else missed. As founder of D2 Operations Consulting, he works with early and growth-stage companies on revenue operations, team execution, and GTM strategy - and his take is that most business problems aren't execution problems. They're information problems wearing an e...
Donny Mashiach is the Founder and CEO of Warrior Group, a finance services firm helping founder-led, scaling businesses install stronger financial infrastructure through fractional CFO, bookkeeping, controller, and strategic consulting services. Donny started his entrepreneurial journey running a kosher food concessions operation at Wrigley Field befo...
From candy dealer to fractional CFO to AI SaaS founder - Joe Siegel, founder of Greenlight Financial Group, has been hustling since he was slinging pixie sticks and sodas out of his middle school locker. In this episode, Joe takes us through one of the wildest origin stories we've had on the show: dropping out of high school at 15, getting his GED, ba...
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 bui...
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 S...
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 ...
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...
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 th...
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.
<...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, Ja...
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 st...
Nick Reich is the co-founder of Abundant Empowerment and the founder of CoLab - a peer-powered community for consultants and leaders. A first-gen college kid from Evansville, Indiana, Nick went from school social worker to building the fastest state championship basketball program in Indiana high school history, and then spent the next 15 years turnin...
Ryen Salo is the Client Experience Manager at CherryBecker, a 10-year CX veteran, Association for Accounting Marketing (AAM) member and speaker, Finnish sauna enthusiast, and self-described "one and fun" mom living just outside Portland, Oregon. In this episode, Ryen takes us from selling candy and running a seven-dollar blackberry stand in Grants Pas...
What do a $180 driveway shoveling gig, a fake million dollar bill at the Houston airport, and raising over $2 billion in capital all have in common? Brad Blazar. This week on Scrappy But Successful, Jack sits down with the founder of Capital Connections - a knighted speaker, bestselling author, podcast host, and genuinely one of the most interesting p...
Steve Hopper spent years climbing the corporate ladder before a toxic work environment - and a nudge from his wife - pushed him to bet on himself. In 2004, he founded Inviscid Consulting, a supply chain and warehouse operations firm that has since worked with clients ranging from $80B corporations to PE-backed startups. What started as turning over ro...
La Tonya Roberts has always had a plan - and the grit to execute it. From running a lemonade stand outside a military base in Alaska at age 7 to pitching her parents with formal PowerPoint presentations for Christmas gifts, La Tonya's scrappiness has always been strategic. Today she's the founder of Harmony Consulting Group, a fractional COO, AI strat...
What happens when a near-death experience on a Manhattan construction site becomes the catalyst for a career in sales — and eventually a global consulting company? Stephen Steers, founder of Steers Consulting Group, comedian, keynote speaker, and author of Superpower Storytelling, joins Jack to trace the scrappy origins of an unlikely entreprene...
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