Insights

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

John Buckner is the founder of Insightful Selling and a Fractional VP of Sales advisor at Sales Xceleration, bringing a thirty-year corporate sales and marketing career to small businesses that need to grow. His resume includes DuPont, Chick-fil-A, 7-Eleven, Walmart, and Home Depot, but John calls himself an "accidental salesman" - his path started on his father's land surveying crew in the North Carolina foothills, not a sales floor. In this episode, John and Jack dig into why the best salespeople act as guides instead of salesmen, with the customer as the hero of their own story. John shares the data-driven pitch that won Chick-fil-A's coffee business away from 23 other roasters, the pharmacy counter interaction that taught him what trust-based selling actually looks like, and why he built his whole practice around single, focused solutions instead of overwhelming clients with everything he offers. Chapters: 0:00 Welcome and the Lake Norman monster fun fact 0:42 Scrappy or sophisticated - John's 300 CEO outreach push 6:03 Family roots - a land surveyor dad and the family entrepreneurial itch 10:32 Reframing sales - the customer as hero, John as guide 13:44 The shingles shot story - trust-based selling in action 18:24 Early sales instincts - basketball, retail spiffs, and rapport 22:02 Winning Chick-fil-A's coffee business with data and insight 28:20 Getting out of the box - curating your offer instead of overwhelming clients 34:46 Lightning round - garage sales, cash flow games, and inbox habits 40:22 Final takeaway - make the customer your true north John W. Buckner brings a broad sales and growth background from a thirty-year corporate career, including leadership roles as VP of marketing and SVP of sales, spanning Fortune 500 companies, national middle-market firms, and major retailers including DuPont, Georgia-Pacific, Simpson Strong Tie, Chick-fil-A, Taco Bell, Sonic, 7-Eleven, Walmart, Target, Home Depot, and Lowe's. His firm, Insightful Selling, helps small businesses win through people, process, and technology. https://LinkedIn.com/in/johnwbuckner https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

This isn't another line item you eat the cost of - it's a new tier you can charge for. Offer bookkeeping only, bookkeeping plus dashboards, or full advisory on top. Priced low so you can mark it up and package it as a differentiator. Built for advisors, not against their margins Three tiers: bookkeeping, dashboards, or full advisory Pass the cost through with a markup Position it as a premium package, not an add-on Charge more for the value you already deliver Try for free - https://www.pineappleanalyst.ai/get-started Learn more - https://pineappleanalyst.ai Questions - support@pineapplecf.com

Clients ignore reports because they're a static snapshot that feels like accounting class. Here's what actually gets checked. An interactive dashboard tells the full story in 15 seconds - and once clients see it, they come back for more. Why static reports get ignored What makes a dashboard actually engaging Clients becoming accidentally data-driven Why they start checking it like a notification How to be the advisor they actually want to hear from Try for free - https://www.pineappleanalyst.ai/get-started Learn more - https://pineappleanalyst.ai Questions - support@pineapplecf.com