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Build a custom CFO dashboard with a simple prompt, then roll it out to every client at once - all from their real QuickBooks data. Watch how Pineapple Analyst turns a plain-language prompt into a full CFO dashboard - trailing 13-month gross and net profit, revenue KPIs, client concentration, and a growth scenario planner - then gets shared to your entire client roster in one click. Turn a simple prompt into a full custom CFO dashboard Pull trailing 13-month gross profit and net profit trends Get KPIs like revenue per client and top 20% customer concentration Build a scenario planner to model future growth Match your dashboard to your brand colors and style Share one template to all clients, pulling each client's own data automatically Try for free - https://www.pineappleanalyst.ai/get-started / Learn more - https://pineappleanalyst.ai / Questions - support@pineapplecf.com Want chapter timestamps for this one too, or is that covered separately?

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 growth. She grew up in a family of six kids and lifelong entrepreneurs, was homeschooled, and worked her way from executive assistant to COO before launching Compass two years ago. In this episode, Jack and Beata dig into scrappy LinkedIn outreach that actually works, why she keeps her overhead lean, and the one thing every founder needs to rally a team around a single goal. Chapters: 0:00 - Intro and the sophisticated vs scrappy question 1:28 - Growing up in a family of six entrepreneurial kids 4:00 - What Compass Consulting actually does 6:41 - Early jobs, grades, and life homeschooled 12:09 - From executive assistant to founding Compass 15:49 - ICP evolution and landing the first client 20:51 - Scrappy LinkedIn marketing that actually works 24:32 - Cash flow, bartering, and staying lean 30:46 - The one goal every team should rally around 34:41 - Lightning round: scrappy or sophisticated Connect with Beata: https://heycompass.co https://www.linkedin.com/in/beata-rouleau/ 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

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 firm. Debbie shares the story of temping for Anderson Consulting, discovering change management, and eventually helping HUB International win a Stevie's Gold Award for Best Employer. She and Jack dig into why teams (not individuals) are where real business transformation happens, her sweet spot serving $100M-$700M middle market companies, and how she is scaling from 1:1 coaching into a vetted team coaching model. Then it's a scrappy vs sophisticated lightning round covering everything from lap desks to asking for referrals. Chapters: Chicago Roots and the Scrappy Verdict (00:00) Bootleggers, Mathematicians, and Zero Entrepreneurs (01:51) Medieval History to Anderson Consulting (04:21) Serf to Yeoman: Finding Change Management (05:36) The Best Employer Award and Summer Camp During COVID (12:59) Why Teams Are Where Work Happens (32:24) Lightning Round Begins: Scrappy vs Sophisticated (32:57) Scrappy Early Days and Saving the Marriage with a Cleaner (35:04) LinkedIn Only: Scrappy Marketing That Worked (36:04) Finding the $100M-$700M Sweet Spot (38:41) Final Verdict and Where to Find Debbie (44:36) Guest Links: Website: https://www.theplagergroup.com/ LinkedIn: https://www.linkedin.com/in/dsplager/ 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

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 mid-market companies and private equity backed brands turn supply chains into a competitive advantage instead of a liability. In this episode, Anna and Jack dig into why "anti-fragile" beats "resilient," how she built a negotiating edge without cigars, golf, or poker, and the real story of leaving a W-2 paycheck to bet on herself, twice. Chapters: Meet Anna McGovern, founder of Pondview Consulting Growing up the daughter of immigrant entrepreneurs Psychology major to Unilever procurement, the unlikely path 23 years at Unilever, from local to global supply chains What she teaches college students about supply chain careers Anti-fragile vs resilient, the thesis behind her book Building trust with suppliers without cigars, golf, or poker Starting Pondview, COVID, and the leap to going all in How relationships built her client base from day one Scrappy vs sophisticated lightning round Connect with Anna: Website: https://pondviewconsulting.com/ LinkedIn: https://www.linkedin.com/in/annamcgovern/ X: https://x.com/annamcgovern_sc Instagram: https://www.instagram.com/anna_supplychainexpert 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 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 she fired her first client within four months, why every small business hits a wall at 4-5 employees, her strict "get paid up front" policy, and how she has built her team so the company runs smoothly whether she is in the office or not. They also dig into her take on EOS, the scrappiest marketing moves she has tried, and a rapid-fire round covering monitors, business cards, and inbox habits. Chapters: - 00:00 - Sophisticated or Scrappy? Susan's Opening Answer - 01:33 - Growing Up in a Family of Entrepreneurs - 06:38 - Starting Beyond the Chaos in 2016 - 08:48 - Firing Her First Client in Four Months - 11:33 - Why Businesses Break at 4-5 Employees - 16:21 - Delegate vs Abdicate and Setting Expectations - 17:10 - Susan's Take on EOS - 22:38 - The First Hire and Getting Out of the Weeds - 23:23 - Getting Paid Up Front and Tapping the Line of Credit - 27:54 - Lightning Round: Monitors, Business Cards, and Inbox Habits - 41:11 - Where to Find Susan and Beyond the Chaos Guest Links: [FLAG: Bio and Links section in Susan's prep doc is blank - Jack should confirm the correct links before publishing] Website: https://beyondthechaos.biz LinkedIn: https://www.linkedin.com/in/susanfennema/ 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

Tired of AI dashboards that guess which accounts count as COGS or marketing? Here's how to fix that for good. In this video, we walk through building a custom knowledge base for each client in Pineapple Analyst. Once it's set up, every AI chat and dashboard you build references that knowledge base automatically, so the AI stops guessing and starts building exactly what you meant. Define exactly how you want accounts classified, like payroll or marketing Install a knowledge base on a per-client basis in just a few clicks Cut down on AI guesswork across every future dashboard and chat Build a full dashboard from a single simple prompt Watch it generate KPIs, trends, and account breakdowns in minutes Save and share the finished dashboard directly with your client Perfect for bookkeepers adding advisory services or CFOs going AI-forward with clients. Try for free - https://www.pineappleanalyst.ai/get-started Learn more - https://pineappleanalyst.ai Questions - support@pineapplecf.com

Customize the knowledge for your clients to make custom dashboards! In this video, we walk through building a custom knowledge base for each client in Pineapple Analyst. Once it's set up, every AI chat and dashboard you build references that knowledge base automatically, so the AI stops guessing and starts building exactly what you meant. Define exactly how you want accounts classified, like payroll or marketing Install a knowledge base on a per-client basis in just a few clicks Cut down on AI guesswork across every future dashboard and chat Build a full dashboard from a single simple prompt Watch it generate KPIs, trends, and account breakdowns in minutes Save and share the finished dashboard directly with your client Perfect for bookkeepers adding advisory services or CFOs going AI-forward with clients. Try for free - https://www.pineappleanalyst.ai/get-started Learn more - https://pineappleanalyst.ai Questions - support@pineapplecf.com

Building custom dashboards with Claude or other AI is easier than ever - but not all tools are equal. Here's how Claude stacks up against Pineapple Analyst AI across all 7 steps. Try for free - https://www.pineappleanalyst.ai/get-started Learn more - https://pineappleanalyst.ai Questions - support@pineapplecf.com