Insights

Most accountants and advisors spend hours putting together a monthly report their clients never even open. Here's how to flip that into a dashboard clients actually use, and happily pay you more for. Pull all your client financials into one automated spot Build an AI analyst that understands the data it's looking at Roll out a dashboard so each client sees their own performance Turn that into a true advisory offer, not just reporting Charge 250 dollars a month on a platform that costs you 50 Some clients pay over 1,000 dollars a month for a great dashboard It's called Pineapple Analyst, and it's already built for you. Try for free - https://www.pineappleanalyst.ai/get-started Learn more - https://pineappleanalyst.ai

If you're a fractional CFO using AI, you're probably three steps away from it feeling truly game-changing - and you're not alone. Most advisors hit the same wall: building one report and rolling it out to every client, giving clients their own login to see just their data, and pulling in more than financials in one spot. Build one report and share it across your entire client roster with a click Publish reports so clients log in and see only their own information See every client's data yourself while they only see theirs Link financial and non-financial data - forecasts, sales, marketing - in one spot Skip the manual rebuild-per-client workflow entirely Get these as default features, not a custom build Pineapple Analyst AI was built for exactly these gaps. Try it for free. Try for free - https://www.pineappleanalyst.ai/get-started Learn more - https://pineappleanalyst.ai Questions - support@pineapplecf.com

Pulling one report across dozens of QuickBooks clients shouldn't eat your whole day - but it does. Here's what that actually looks like, and the faster way to get it done. Jack breaks down a real example: manually pulling the total bank accounts line item across 10 clients took 30 minutes. With 96 clients on the roster, that's a full day of work just for one report - and QuickBooks AI still only works one client at a time. In this video you'll see: The manual QuickBooks process for pulling one line item across multiple clients Where QuickBooks AI helps and where it still falls short for multi-client work Consolidated views in Pineapple Analyst showing every client's data in one place Line-by-line comparisons generated by AI from a single prompt Building one report and sharing it to every client with one click Why this problem shaped how Pineapple Analyst was built Try for free - https://www.pineappleanalyst.ai/get-started Learn more - https://pineappleanalyst.ai Questions - support@pineapplecf.com

Ron Latz is the founder of LegalFenix, a fractional CMO and marketing advisory firm that works exclusively with law firms. After more than 15 years in legal marketing, including stints at FindLaw and Mockingbird Marketing, Ron built LegalFenix into a vendor-neutral shop that helps firms sort out what is actually working in their marketing and what is not. In this episode, Ron and Jack cover Ron's path from a metal band and umpiring Little League games in New Jersey to running a marketing consultancy built entirely around law firms. They dig into why Ron refuses to take referral fees, how his hiring process still ends with him flying out to meet every candidate in person, and the KPIs his team leans on to prove value to clients month after month. Along the way: dot-net domains, the credit card timing game, and eating cereal out of clean Tupperware. Chapters: 0:00 Welcome and the scrappy or sophisticated question 1:08 Growing up in New Jersey and an early love of hockey 3:31 Garage sales, fundraising calls, and a band in the emo days 7:42 What LegalFenix does for law firms today 8:47 Landing on legal marketing and staying vendor neutral 10:39 From Xerox to FindLaw to starting Athlete Consulting 14:30 Three name changes and finally landing on LegalFenix 16:35 Leaving agency life and going vendor neutral for good 27:01 Proving value to clients and the KPIs that matter 32:01 Scrappy versus sophisticated lightning round 43:40 Where to find LegalFenix and final thoughts LegalFenix website: https://legalfenix.com Ron Latz on LinkedIn: https://www.linkedin.com/in/ronlatz/ Jack Tompkins on LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Pineapple Consulting Firm: https://www.pineapplecf.com Pineapple Analyst AI: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Katie Bedford spent seven years as an aerospace engineer building space robotics before pivoting through digital agencies, project management, and five years as a fractional COO to land where she is today: a strategic advisor and thinking partner for agency leaders. She's the founder of K Bedford Consulting in Vancouver, and her whole approach is built on giving business owners the honest, unbiased conversation they can't get from anyone else on their team. In this episode, Katie and Jack dig into how an engineering brain wired for risk and rigorous logic became the perfect training ground for advisory work, why so many small businesses mistitle their staff, the real difference between AI-as-pattern-finder and AI-as-judgment-maker, and the emotional weight of helping leaders make the calls they already know they need to make. Katie also shares two tools she built herself using AI (a custom CRM and a cash flow forecaster) and makes a genuinely useful case for why chasing AI tools without a centralized dataset is putting the cart before the horse. Chapters: 0:00 Scrappy or sophisticated: Katie's answer 1:29 Cinder blocks, jewelry, and Katie's non-entrepreneurial roots 4:13 What a thinking partner actually does 7:33 How the advisory relationship gets structured 9:41 Why small companies over-title their people 13:40 From grade one space obsession to aerospace engineer 14:41 NASA, the Canada Arm, and getting the "get out of jail free" layoff 16:43 The pivot into agency life and finding the thinking partner niche 20:36 Where AI actually helps (and where it can't) 24:04 Building her own CRM and cash flow tool with AI 27:23 The overbuilt website and the box of unused business cards 29:20 Her one scrappy money story: fighting for a business credit card 34:02 The Steve Martin mindset and Katie's rotating hobbies 36:08 Broadening her niche beyond digital agencies 43:09 The Thinking Partner ROI calculator Katie Bedford: LinkedIn: https://www.linkedin.com/in/katie-bedford/ Jack Tompkins: 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

Your clients think you're just the person who sends the report - here's how to become their true advisor instead. If you're managing 20-200 clients and want to scale advisory services, this breaks down the exact approach that works. Jack (aka Pineapple Jack) shares the two-step framework for repositioning your firm: making advisory services the headline offering instead of a bookkeeping add-on, and giving clients their entire company performance in one visual dashboard they'll actually check. In this video you'll see: Why clients put advisors into a "good, bad, or ugly" bucket - and how to get out of it A live look at a default QuickBooks dashboard with KPIs, trends, and AI-generated insights How the built-in AI analyst preps you for advisory conversations before they happen Building fully custom dashboards from a simple prompt, no coding required White-labeled, automated daily updates so clients always see current data Combining financial and CRM (HubSpot) data for the complete company picture This is built for accountants and bookkeepers serious about growing advisory revenue with centralized client data - not for firms looking to stay purely in bookkeeping, tax, or Excel. Try for free - https://www.pineappleanalyst.ai/get-started Learn more - https://pineappleanalyst.ai Questions - support@pineapplecf.com

Aaron Gutowski is a Partner and Chief Sales Officer at Chief Outsiders, an "Executives-as-a-Service" firm that places fractional CMOs and CSOs inside mid-market companies. He was one of the first CSOs to join the firm, and he brings more than 20 years of sales leadership experience across data, research, and industrial services to every engagement. In this episode, Aaron traces his sales instincts back to a Detroit News paper route as a kid, then walks through the hustle that got him his first real sales job selling computers at a company that's now Verizon, including the time he secured a shipment of Apple computers with a PO number made up of his own birthday. He and Jack dig into how Aaron landed his first major client at Chief Outsiders, why the single most important KPI in any sales org is the number of new first meetings (not total meetings), and why honest, sometimes uncomfortable conversations with clients build more trust than telling them what they want to hear. Chapters: 0:00:00 Intro and meet Aaron Gutowski 0:01:10 Scrappy all the way, growing up in Detroit 0:03:13 The Detroit News paper route hustle 0:06:09 What a fractional CSO actually does 0:09:43 Landing HBS Solutions, his first big client 0:14:45 Selling Apple computers and the birthday PO hustle 0:29:47 Coaching honesty into hard sales conversations 0:31:15 The one KPI that predicts sales success 0:35:10 Lightning round and Chief Outsiders AI program Connect with Aaron Gutowski: LinkedIn: https://www.linkedin.com/in/aarongutowski/ Chief Outsiders profile: https://www.chiefoutsiders.com/profile/aaron-gutowski Connect with Jack Tompkins: 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

Tina Ruark-Baker has already built and sold two companies, spent two decades climbing to the C-suite, and then walked away from the corner office to start a third business from scratch. Today she runs TRB Creative, coaching small businesses, entrepreneurs, and nonprofits on the one channel she believes almost nobody uses correctly: LinkedIn. In this episode, Tina and Jack trace her path from a staffing company she started at 18 in her dad's basement, through 20 years in New York City, to her current life at the beach in a golf community outside Charlotte. She breaks down why personal LinkedIn profiles outperform company pages, why she said yes to painting an entire medical office (20 canvases, zero prior experience), and how nine different revenue streams stay connected through a single referral-driven philosophy: make the connection, then get out of the way. Chapters: 0:00 Intro and the scrappy vs sophisticated verdict 1:35 From Detroit hustle to two exits by 1999 3:25 New York, a chance encounter, and 20 years in the city 6:32 Walking away from corporate to coach LinkedIn 9:11 Landing first clients through networking 14:23 Saying yes to a 20-painting art commission 18:18 Nine revenue streams and the power partner network 21:13 Finding the real ICP and ditching marketing-only work 25:23 Scrappy marketing, golf, and keynote speaking 30:45 How Tina measures success and builds client trust Connect with Tina Ruark-Baker: LinkedIn: https://www.linkedin.com/in/tina-ruark-baker/ TRB Creative: https://www.trbcreative.com/ Connect with Jack Tompkins: 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