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
Debbie Plager, Founder and CEO of The Plager Group, joins the show to talk about how a medieval history degree turned into a 25-year career in corporate talent leadership and now a coaching and organizational strategy firm. Debbie shares the story of temping for Anderson Consulting, discovering change management, and eventually helping HUB International win a Stevie's Gold Award for Best Employer. She and Jack dig into why teams (n...
Beata Rouleau is the founder of Compass Consulting, a fractional COO practice that helps tech companies between $1M and $20M in revenue build the strategies, systems, and automations that turn plans into predictable growth. She grew up in a family of six kids and lifelong entrepreneurs, was homeschooled, and worked her way from executive assistant to COO before launching Compass two years ago. In this episode, Jack and Beata dig in...
Jack sits down with Susan Fennema, the self-proclaimed "Chaos Eradicating Officer" and founder of Beyond the Chaos, to find out if she is more sophisticated or more scrappy after 10 years in business. Susan shares how she fired her first client within four months, why every small business hits a wall at 4-5 employees, her strict "get paid up front" policy, and how she has built her team so the company runs smoothly whether she is i...
Anna McGovern spent 23 years climbing the ranks at Unilever, from local supply chains all the way to global, before trading Park Avenue for her own consulting practice. As founder of Pondview Consulting, she now helps mid-market companies and private equity backed brands turn supply chains into a competitive advantage instead of a liability. In this episode, Anna a...
Eric Harrison spent his entire life in the women's shoe business, growing up in his family's wholesale distribution company before taking over from his dad in 2008, right before the financial crisis hit. He sold the business to his brother in September 2019, just six months before COVID changed everything. Now he's the Director of Business Development at DBG Advisors, where he helps business owners maximize the value of their compa...
John Rodriguez is the co-founder of Valiant, a firm that embeds Big Four level financial expertise directly into startup teams instead of operating as a black box. Valiant covers everything from fractional CFO work to bookkeeping to payroll, and they specialize in seed to Series B SaaS and tech companies.
Charlie Warden is the Managing Partner of Warden Strategy, a revenue strategy and venture-building firm based in Denver. He's a fractional CGO (Chief Growth Officer), not a CMO or CRO, and he joins Jack to talk about why that distinction matters, why he started a second fractional firm instead of scaling his first, and why he'd rather turn down growth than chase it.
From running a donut resale stand and a baseball card business in ...
Jack Tompkins sits down with Alexandra Erman, a startup operator who has spent two decades building the infrastructure that lets venture-backed companies scale without breaking. Alexandra has architected people strategies, run finance, launched entities across continents, and scaled companies from $500K to $12M in ARR across 12 countries. Before any of that, she ran art galleries in Saint Barthelemy and Paris, crashed one business ...
Jennifer Best is the founder of Copper Compass Group, a fractional marketing firm helping small businesses and startups build real marketing strategy instead of just marketing activity. She's a two-time entrepreneur, a Certified HubSpot Partner, a past SBA award winner, a Forbes Communications Council contributor, and the incoming president of the AMA's Triangle (NC) chapter. In this episode, Jen and Jack dig into her path from cor...
In this episode of Scrappy But Successful, Jack sits down with Natalie Hoop, a fractional COO and coach for fractional consultants, to unpack what it really takes to build a fractional business that works.
Natalie shares her scrappy path from retail leadership at Blockbuster and Borde...
Paul Pompeo is a New York sales guy through and through - born and raised in Queens, started his first business running a paper route crew at age eleven, and never stopped hustling from there. Today he runs Prolan Consulting, where he helps business owners, coaches, and consultants close more of the conversations they're already having instead of chasing more leads...
Hey consultants and fractional professionals - this is the episode where strategy meets scrappiness. Shay Prosser founded North 12 Partners after realizing something crucial: most growing companies (think $1M-$20M revenue) are stuck between startup chaos and corporate process. They've outgrown the founder-doing-everything phase but haven't figured out the systems t...
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...
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