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Hosted by Pineapple Jack · 🇺🇸 US · EN-US · 40 episodes
Established thought leaders with verified media credentials.
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
Pineapple Jack hosts Scrappy but Successful [Consultant's Personalities When No One's Watching], a business show with 40 episodes published.
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 fi
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 grow
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 sh
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 mi
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 busi
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 bo
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
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 strategie
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 C
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 shar
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 Consul
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 revenu
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, t
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
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 schedule
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,
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 strat
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,
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 launc
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 sp
Phil Risher
Phlash Consulting
1 appearance on this show
Brad Blazar
Capital Connections
1 appearance on this show
Steve Hopper
Pratt Plumbing and Heating
1 appearance on this show
La Tonya Roberts
founder · Harmony Consulting Group
1 appearance on this show
Dr. Michele Williams
Head of School · Scarlet Thread Consulting
1 appearance on this show
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Scrappy but Successful [Consultant's Personalities When No One's Watching] is hosted by Pineapple Jack. The show is categorised under business (entrepreneurship) and has published 40 episodes.
Scrappy but Successful [Consultant's Personalities When No One's Watching] has published 40 episodes.
Scrappy but Successful [Consultant's Personalities When No One's Watching] regularly covers business, entrepreneurship, management. It sits in the business category, with a entrepreneurship focus.
Scrappy but Successful [Consultant's Personalities When No One's Watching] is accessible for guests with genuine business expertise. A personalised, episode-aware pitch will still outperform a generic one every time.
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Episodes of Scrappy but Successful [Consultant's Personalities When No One's Watching] average 46 minutes. a focused format where a clear narrative arc and tight preparation matter most.
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