Insights

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

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 embedded strategic leader - the person who helps CEOs build businesses that actually work without them doing all the work. What makes this conversation special is how Shay bridges both worlds. She grew up underneath an accounting desk in her family's truck rental business in Indiana, watched her dad sell the company at 12, then went on to run large-scale events at Microsoft before realizing her real superpower wasn't logistics - it was end-to-end strategy. She even got more money working part-time as a consultant for Microsoft than she made in her full-time salary - a perfect example of knowing your worth. In this episode, we dig into her go-to-market strategy framework, why purpose-driven growth is becoming table stakes for scaling companies, and how she helps clients avoid the trap of reactive growth. We also run through our signature Scrappy vs Sophisticated lightning round covering everything from her messy cable management setup to her approach to email (spoiler: she sends herself misspelled reminders and has a Claude coach for client interactions). Chapters: Family business roots and the mafia lie (00:00 - 03:30) From Microsoft layoffs to premium consulting rates (03:30 - 07:45) Transitioning from events to strategy and realizing what you're actually good at (07:45 - 09:06) Why she left CMO role to start North 12 Partners (09:06 - 10:30) Go-to-market strategy as the missing link for growing companies (10:30 - 15:20) Data, purpose, and intentional growth frameworks (15:20 - 20:45) Why purpose-driven business beats generic mission statements (20:45 - 25:15) The scrappy office setup, cable chaos, and O-ring lighting (25:15 - 39:30) Lightweight systems and getting client responses in one business day (39:30 - 44:00) Shay's Links: https://www.north12partners.com https://www.linkedin.com/in/shayprosser Jack's Links: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Build a custom dashboard with AI in minutes - no code, no complexity, just results in 2 steps. Whether you're doing it manually or using AI, every dashboard build follows the same core steps. Here's the full process plus the shortcut that skips most of it. What we cover: Data source connection (QuickBooks, HubSpot, and more) Building a database and automated data flow Dashboard design - visuals, interactions, and date filters The 15-second test every good dashboard should pass Publishing and one-click client sharing How Pineapple Analyst skips straight to step 5 with one prompt Chapters: 0:00 Introduction 0:24 The steps every dashboard build requires 0:57 Data infrastructure explained 1:35 Dashboard design - visuals, filters, and interactions 2:10 Publishing and client sharing 2:25 How Pineapple Analyst handles it all 3:19 Live demo - building a dashboard with one prompt 5:09 Saving and sharing with clients 5:51 Results and wrap-up Try for free - https://app.pineappleanalyst.ai/start-consulting Learn more - https://pineappleanalyst.ai Questions - support@pineapplecf.com

If you're a fractional CFO or accountant who wants to deliver AI-powered insights to your clients - and get the credit for it - Pineapple Analyst is built for you. In this demo, we walk through how Pineapple Analyst works as your white label AI analyst and CFO dashboard solution, including: - Pre-built QuickBooks dashboards ready in minutes (executive overview, P&L, balance sheet, and more) - An AI analyst your clients can ask questions to - fully customizable with client-specific context - Custom dashboard creation with a simple prompt - no code, no weeks of setup - Full white label branding so your clients associate the insights with you - Multi-client management that scales from 2 clients to 200 You stay the strategic advisor. We stay behind the scenes. Reach out: PineappleAnalyst.ai jack@pineapplecf.com

Stop building dashboards one client at a time. Pineapple Analyst lets you create a custom dashboard from a simple prompt, then push it to hundreds of clients at once - all in your branding. Build a dashboard from a simple text prompt Save and share it across your entire client roster instantly Every client sees the same branded view in their own environment Customize colors, visuals, and layout to match your firm One setup, hundreds of clients covered Try for free - https://app.pineappleanalyst.ai/start-consulting Learn more - https://pineappleanalyst.ai Questions - support@pineapplecf.com

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: 00:00 - Intro and scrappy vs sophisticated 01:09 - Growing up across Canada and the entrepreneur in the family 02:40 - First company at 18, swearing off business, then getting pulled back in 04:35 - Halifax co-working scene and the accidental birth of Mindsea 06:38 - Collaborative consortiums, committed co-discovery, and lessons from trying to share work 07:48 - How SalesRight was born from an internal tool and got acquired by FastSpring 10:19 - What Pace Pricing does - end-to-end pricing strategy for B2B SaaS 11:31 - The most common pricing problem - flatline growth, churn math, and expansion revenue 13:46 - Why pricing confidence comes from conviction, not just data 14:40 - Four levels of pricing validation and how to get there scrappily 17:32 - Jobs to be done, customer interviews, and using AI to analyze them 22:43 - AI in hiring, irresponsible NOT to use AI, and democratizing knowledge 25:40 - AI native vs AI forward, human-led AI-assisted 27:51 - Starting a business in Spain in one afternoon with Claude and landing pages 33:01 - Committed co-discovery - 90 days, 50/50, and why stealth mode is dead 35:08 - Trust as the real moat in AI businesses 37:00 - Love them, help them, pay you - the three things that matter 38:01 - Lightning round: airport anxiety, business class, couch work, inbox zero Bill Wilson Links: LinkedIn: https://ca.linkedin.com/in/wdrwilson Company: https://www.pacepricing.com Blog: https://www.pacepricing.com/blog Jack Tompkins Links: 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