26. How B2B SaaS Companies Leave Money on the Table with Bill Wilson

30. Why Most Small Business Marketing Misses the Mark with Jen Best

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

31. Stop Building Yourself Another Job: Fractional CXO Company Building with Natalie Hoop

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/ [http://nataliehoop.com/] https://www.linkedin.com/in/nataliehoop/ [https://www.linkedin.com/in/nataliehoop/] https://www.instagram.com/nataliehoop_ops/ [https://www.instagram.com/nataliehoop_ops/] Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ [https://www.linkedin.com/in/jack-tompkins/] https://www.pineapplecf.com [https://www.pineapplecf.com] https://www.pineappleanalyst.ai/ [https://www.pineappleanalyst.ai/] https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng [https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng]

29. Why More Leads Won't Fix Your Sales Problem with Paul Pompeo

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.prolanconsulting.com] https://www.linkedin.com/in/paulvpompeo/ [https://www.linkedin.com/in/paulvpompeo/] https://breakthroughsellingwithpaul.com [https://breakthroughsellingwithpaul.com] Connect with Jack Tompkins: https://www.linkedin.com/in/jack-tompkins/ [https://www.linkedin.com/in/jack-tompkins/] https://www.pineapplecf.com [https://www.pineapplecf.com] https://www.pineappleanalyst.ai/ [https://www.pineappleanalyst.ai/] https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng [https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng]

28. Building a Business That Doesn't Run Through You with Shay Prosser

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.north12partners.com] https://www.linkedin.com/in/shayprosser [https://www.linkedin.com/in/shayprosser] Jack's Links: https://www.linkedin.com/in/jack-tompkins/ [https://www.linkedin.com/in/jack-tompkins/] https://www.pineapplecf.com [https://www.pineapplecf.com] https://www.pineappleanalyst.ai/ [https://www.pineappleanalyst.ai/] https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng [https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng]

27. How to Unlock Hidden Warehouse Capacity Without Spending a Dime with Adrian Betts

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, Adrian drops analogy after analogy - and every single one lands. Chapters: 00:00 - Intro and scrappy or sophisticated 01:04 - Growing up scrappy: Atlanta roots and a family of entrepreneurs 03:51 - Early jobs, bad grades in science, and learning to show your work 07:47 - Unlearning perfectionism and the baseball batting average mindset 10:37 - From aviation dreams to consulting: the 2004 start and 2017 restart 14:23 - Building a client base through word of mouth and water cooler credibility 20:46 - ICP evolution: why Adrian now says no to Enterprise and SMB 23:39 - How Adrian actually unlocks capacity in a warehouse - the full method 27:06 - Measuring performance with throughput rates, order accuracy, and cube 32:48 - Scrappy vs sophisticated: airports, inbox chaos, and the file naming system Adrian Betts / Xpandur: https://www.linkedin.com/in/adrianbetts/ [https://www.linkedin.com/in/adrianbetts/] https://xpandur.com [https://xpandur.com] Jack Tompkins / Pineapple Consulting Firm: https://www.linkedin.com/in/jack-tompkins/ [https://www.linkedin.com/in/jack-tompkins/] https://www.pineapplecf.com [https://www.pineapplecf.com] https://www.pineappleanalyst.ai/ [https://www.pineappleanalyst.ai/] https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng [https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng]