Scrappy but Successful [Consultant's Personalities When No One's Watching]

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 owner...

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. In this episode, John walks through his unusual path: a disciplined, "sophisticated" start in...

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 sta...

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 Barthele...

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...

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 Borders to startups, fractional operations, and coaching. Along the way, she tells wild behind-the-scenes stories abou...

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. In this episode, Paul takes us...

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 to scale. Shay steps in as that em...

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-performing systems. In this episode,...

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 single afternoon with AI. Chapters: 0...

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 building actually looks like, why she...

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 execution costume. Jack and Drew d...

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 before moving through investment banking on Wall St...

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, bartending through his 20s while waiting on finan...

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 built one of the most practical, data-driven sales...

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 Storytellers and recognized as the world's leadi...

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 late), walks through his 6-component Functional Mar...

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 Specialists (BGES) in Sydney, where he now hel...

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 this episode, Tina and Jack dig into conscious ca...

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. Tanner breaks down how he built the Brand Operat...

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, Jack and Phil trace the full origin story - from...

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 th...

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 turning those lessons into a people first framework f...

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 Pass, to driving a 50-mph Mug Root Beer VW Bug for...

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 people to ever sit across from Jack. Brad breaks...