Insights

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 companies before they sell. Eric and Jack get into the family business lessons Eric learned (and unlearned), what it actually felt like to hand over a company he'd run his whole adult life, and why some businesses are flat out unsellable. Eric also breaks down the real dollar difference between a business with systems and processes in place versus one running on gut instinct alone, and it's bigger than you'd think. Chapters: 00:00 Scrappy or sophisticated, Eric's early verdict 02:00 Selling newspapers and candy bars as a kid 06:20 Lessons learned and unlearned from his parents 08:06 Growing up inside the family wholesale shoe business 12:37 Taking over the company in 2008 right before the crash 13:18 Selling the business to his brother in 2019 22:05 The hardest years and the leanest budgets 24:15 What MA advisor Eric would tell business owner Eric 27:01 Bringing data and Tableau into a gut feel business 32:19 The real valuation gap between systems and chaos 40:08 Inbox habits and the scrappy vs sophisticated verdict Eric Harrison: DBG Advisors: https://dbgadvisors.com/broker/eric-harrison/ LinkedIn: https://www.linkedin.com/in/ericharrisonbam/ LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Pineapple Consulting Firm: https://www.pineapplecf.com Pineapple Analyst: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

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 Big Four public accounting that flipped into full scrappy mode once he went out on his own. He shares the wild origin story of Valiant, which started with zero employees, no business entity, and a single client at Zynga that his co-founder talked into a deal before the company even had a name. John also breaks down why startups increasingly expect dashboards and strategic analysis instead of just clean books, and why he intentionally builds his clients toward hiring their own in-house replacement instead of holding onto the relationship forever. Chapters: Intro and the sophisticated vs scrappy question Growing up in LA with an entrepreneurial mom Berkeley, working hard over being smart, and the Big Four grind Learning to disconnect from the badge of honor of overworking Why founders should delegate accounting and focus on their strengths The Zynga origin story: a company with no name, no employees, and one client Naming Valiant and finding the right ICP over time Why clients now expect analysis and outcomes, not just bookkeeping The hire your replacement model and why transparency builds trust Lightning round and the final scrappy vs sophisticated verdict Connect with John Rodriguez: LinkedIn: https://www.linkedin.com/in/john-s-rodriguez-35685916/ Website: https://www.usevaliant.com Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Company: https://www.pineapplecf.com Speaking: https://www.pineappleanalyst.ai YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

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 completely, and rebuilt from there. In this episode, Alexandra and Jack dig into her path from art dealer to fractional COO and CEO, the financial and operational chaos of running cross-border startups, and why she thinks every early-stage company needs a generalist before it needs specialists. Chapters: 00:00 - Sophisticated or scrappy: Alexandra's verdict 01:32 - Growing up in Paris and becoming an art dealer in Saint Barthelemy 07:38 - Crashing the gallery business and starting over in corporate France 11:18 - Breaking into the fractional startup world in 2005 13:46 - The cross-border medical device company and seven years untangling international finance 19:11 - Joining Agora Pulse and scaling a bootstrapped SaaS company for a decade 26:14 - The case for hiring a generalist before you hire specialists 32:23 - From Agora Pulse to StreamSets to BforeAI and the startups she runs today 40:33 - Scrappy money stories: ten euro days and pulling favors from old coworkers 49:11 - Final advice: don't wait too long to hire your key people Connect with Alexandra: https://www.linkedin.com/in/alexandraerman/ Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

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 middle school to founding his first agency on campus with free university software, Charlie's entrepreneurial roots run deep. He shares the early days of bootstrapping with his now-wife in a 600 square foot apartment, the hard lessons from a venture-backed hardware startup that took him to China, and how he eventually landed on the Chief Growth Officer model that breaks down the marketing, sales, and customer success silos most businesses get stuck in. Charlie also opens up about Warden Strategy's deliberately narrow ICP (the $1M-$10M B2B service businesses that fall below the private equity threshold), why "we need more leads" is almost never the real problem, and how he and his team built a studio arm for side projects they're genuinely passionate about. Then Jack and Charlie wrap with a scrappy versus sophisticated lightning round covering inbox habits, dryer sheets, and airport efficiency. Chapters: 00:00 - Scrappy or sophisticated: Charlie's take 03:43 - The donut stand and baseball card hustles 09:08 - Launching Lion Head Productions in college 14:11 - Bootstrapping on $80 grocery weeks 18:12 - The venture-backed hardware startup and the move to Denver 23:03 - Building Warden Strategy and the studio arm 26:11 - Why "Chief Growth Officer" instead of CMO or CRO 30:20 - The lead generation myth and what's really broken 33:18 - Defining (and defending) a narrow ICP 35:48 - Scrappy vs. sophisticated lightning round Connect with Charlie: LinkedIn: https://www.linkedin.com/in/charlie-warden/ Company: http://www.wardenstrategy.com Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

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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 about Blockbuster missing the DVD/Netflix moment, Borders handing online book sales to Amazon, and why companies often fail when they ignore the people closest to the customer. Jack and Natalie also dig into the real challenges fractional consultants face: undercharging, scope creep, weak positioning, vague ICPs, burnout, and accidentally building “another job” instead of a business. Natalie breaks down how fractionals can clarify what they solve, package their services, make better business decisions, and speak directly to the pain their clients actually feel. If you’re a fractional consultant, coach, operator, or founder trying to grow without burning out, this one is packed with practical advice. Chapters 00:00 Intro: Scrappy But Successful 00:59 Natalie’s scrappy roots and nontraditional path 03:34 How retail became Natalie’s business education 09:14 Blockbuster’s missed DVD and Netflix opportunities 13:28 Borders, Amazon, and the cost of bad strategic bets 15:00 Sunk cost fallacy and knowing when to pivot 18:04 Treating business changes like reversible decisions 23:36 Natalie’s first fractional client after being laid off 27:12 Undercharging, overdelivering, and scope creep 28:04 Building the right ICP instead of another job 34:12 Positioning fractional services around real client pain 46:54 Jack gets coached on Pineapple Analyst positioning Connect with Natalie: http://nataliehoop.com/ https://www.linkedin.com/in/nataliehoop/ https://www.instagram.com/nataliehoop_ops/ Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

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 corporate marketing into fractional work, how she defines and re-defines her ICP, why she'd rather refer out work than fake expertise she doesn't have, and how she's started layering AI agents into her own operations - then they run through a full Scrappy vs. Sophisticated lightning round covering everything from inbox management to Six Flags churros. Chapters: 00:00 - Intro and the Scrappy vs. Sophisticated Question Jack kicks off with a Raleigh fun fact and brings on Jen Best, founder of Copper Compass Group, who immediately claims the scrappy side of the spectrum. 01:10 - Family of Entrepreneurs and Early Jobs Jen traces her entrepreneurial streak back to her parents, plus stories from working at Six Flags and a string of early side jobs. 08:00 - The Pandemic Pivot Into Fractional Work How a cross-country move, a corporate pay cut, and a side project for a former colleague turned into the start of Copper Compass Group. 11:00 - Defining (and Redefining) the ICP Jen breaks down why ideal client profiles aren't static, how she approached persona-building before AI, and why critical thinking still has to come first. 15:30 - The Pandemic Ramen Noodle Years A candid look at the financial anxiety of buying a house and going fractional at the same time, and the "next normal" mindset that came out of it. 20:00 - Knowing When to Refer Instead of Fake It Why Jen would rather hand off work to a trusted partner than oversell her own skill set, and how that's paid off in long-term referral relationships. 24:30 - Putting AI Agents to Work Jen walks through the agents she's built with Zapier, ClickUp, and HubSpot to automate her own admin, and why she's holding back on rolling AI deeper into client work just yet. 29:30 - AI, Hiring, and the Human Touch A conversation about AI-run job interviews, new graduates entering an AI-disrupted job market, and why human expertise still wins long-term. 31:30 - Scrappy vs. Sophisticated Lightning Round Family reviews, childhood collections, infomercial purchases, QVC confessions, monitor setups, and how Jen escapes a networking conversation that's run its course. 43:00 - What's Next and Closing Thoughts Jen talks about upcoming training programs, building a fractional referral network, and leaves the audience with one piece of advice: take the leap. Jen Best: LinkedIn: https://linkedin.com/in/jenbest6 Website: https://coppercompassgroup.com Newsletter (LinkedIn): https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7292543398345867264 Newsletter (Substack): https://thebestbrew.substack.com/ Jack Tompkins / Pineapple Consulting Firm: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

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 from his blue-collar Queens upbringing (his grandfather built piano casings, his father ran plumbing for Manhattan high-rises) through his early hustles - paper routes, mobile bartending, demolition work - and into his real sales education: knocking on 70-80 doors a day in the boiler-room telecom era of the early 2000s. He shares how that door-to-door, phone-heavy grind shaped his approach to value-based selling, objection handling, and closing without being pushy, plus how those same principles translate for small business owners trying to sell today. Chapters: Growing up in Queens and the blue-collar work ethic his family instilled Running a paper route business with employees at age eleven High school side hustles - mobile bartending and demolition work Becoming an aeronautical engineer, then getting laid off and pivoting to sales Learning to sell by knocking on 70-80 doors a day in NYC and Brooklyn The boiler-room telecom era and surviving constant company collapses Taking the conversation off price and selling on value instead How to ask for the business without sounding pushy or desperate Scrappy vs. Sophisticated lightning round - business cards, lunch orders, and inbox habits What's next for Paul and how to connect with him Connect with Paul Pompeo: https://www.prolanconsulting.com https://www.linkedin.com/in/paulvpompeo/ https://breakthroughsellingwithpaul.com Connect with Jack Tompkins: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng