Insights

Melissa Leavitt started out as a dental assistant, spent 15 years in corporate finance, and now runs Keystone Advisors, a fractional CFO advisory firm for independent dental practice owners. She's a Certified Management Accountant who will happily tell you algebra was her nemesis - which is exactly why she's so good at making practice finances easy to understand. Melissa and Jack cover her Air Force upbringing, saving lawn-mowing money for a $1,000 Ford Taurus, spotting a $10,000 casket purchase while working credit card fraud, and why insurance is the real cash flow clog in dentistry. Plus how she left the dental niche, came back to it, and finally embraced her snarky side in her branding. Scrappy or sophisticated? Stick around for the verdict. Chapters: 0:00:00 Scrappy or sophisticated? Meet Melissa Leavitt 0:01:27 Air Force kid, lawn mowing at 11, and a $1,000 Ford Taurus 0:04:32 The CFO whose nemesis was algebra (plus CMA vs CPA) 0:08:58 From dental assisting to accounting 0:12:17 Unlearning frugality and mac and cheese budgets 0:15:29 Credit card fraud and storytelling with data 0:19:02 Why dental cash flow gets clogged 0:22:06 Launching Keystone Advisors and finding the dental niche 0:29:32 Niching back down, rebranding, and embracing snark 0:34:12 AI, KPIs, lightning round, and the verdict Connect with Melissa: LinkedIn: https://www.linkedin.com/in/melissaleavitt/ Keystone Advisors: https://yourkeystone.co/ 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

Deb Defer is the Director of Client Advisory Services (CAS) at Woodard, where she helps accounting firms modernize and build real advisory practices instead of stopping at compliance. She was named one of Accounting Today's 2026 People to Watch, but her path there was anything but traditional: selling her parents' cigarettes in fifth grade, keeping the books (and delivering foals) on a thoroughbred racehorse farm, driving a rescue squad, and teaching herself QuickBooks while managing the finances of 23 families in Cleveland before landing in public accounting and leading the tech team at BDO. In this episode, Deb shares why firms need the right people and processes in place before buying the next shiny piece of tech, how to define an ideal client profile for CAS, and the $12,000 tool rollout that failed and what it taught her about buy-in and pilots. We also get into why AI rollouts should "slow down to speed up," whether outside hires are an expense or an investment, and why great advisors listen 80% of the time. She wraps with the scrappy vs. sophisticated lightning round, from 5am airport runs for cash to the client she finally fired. Chapters: 0:00:00 Welcome and the scrappy vs. sophisticated question 0:01:22 Adopted twins and selling cigarettes in fifth grade 0:04:54 Racehorse books, rescue squad, and becoming Dr. QuickBooks 0:10:48 Mentors and the lesson of keeping your A+ 0:14:06 People, process, then tech 0:16:48 Defining the ICP for CAS 0:21:20 The $12K rollout that failed 0:25:31 Rolling out AI: slow down to speed up 0:30:18 Why advisory is 80% listening 0:34:04 Scrappy vs. sophisticated lightning round Connect with Deb: LinkedIn: https://www.linkedin.com/in/deborah-defer-5ab40715/ X: https://x.com/DeborahDefer Woodard CAS Consulting: https://www.woodard.com/cas-consulting 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

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Sandra Carlisle has been an entrepreneur since she was 10 years old, hemming pants and lining a customer's jeans with flannel. From there she cleaned houses on a moped, built and sold a cleaning company called Maid in Philly, earned five FINRA licenses, and served as a chief compliance officer at Nationwide Financial. Today she's the founder of Wealthy Palette, a business operations and brand marketing firm for founder-led trade businesses. In this episode, Sandra and Jack dig into Vera, her AI voice agent that answers calls, books jobs, and drops every lead into a CRM for contractors who are on a roof or under a sink when the phone rings. Sandra breaks down her 5-gear Authority Operating System, why every business should be built to be sold, how she accidentally invented value-based pricing as a teenager, and how she went from ketchup sandwiches in a studio apartment to owning 32 acres in Tioga County. Verdict: 100% scrappy. Chapters: 0:00:00 Intro - scrappy or sophisticated? 0:01:50 Growing up in North Jersey and sewing at age 10 0:04:28 Wealthy Palette and the birth of Vera 0:09:10 The meatball call - stress-testing an AI agent 0:11:44 Call recordings, alerts, and the CRM contractors don't have 0:13:57 Cleaning houses on a moped and Maid in Philly 0:15:53 From FINRA licenses to chief compliance officer 0:19:09 Systems, SOPs, and building a business you can sell 0:26:14 Finding the right ICP and the 5-gear Authority Operating System 0:33:18 Ketchup sandwiches, 32 acres, and what's next Connect with Sandra: LinkedIn: https://www.linkedin.com/in/sandra-carlisle/ Website: https://wealthypalette.com/ VERA: https://veraresponsehq.com/ 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

Erin Daiber is the founder and CEO of Well Balanced Accountants, a boutique consulting firm staffed entirely by people with accounting and finance backgrounds. She helps independent CPA firms (roughly $2M to $50M in revenue) free up capacity, build firm value, and stay independent. She is also a CPA and certified coach who started in audit at EY, spent time as an in-house financial analyst, and then went out on her own after burning out as a high-performing accountant. In this episode, Erin takes us from a Cleveland family tool company (and a grandmother who kept money in the linen closet) to coaching paying clients from her car in a parking lot at lunch. We dig into the professor who talked her into accounting, why so many CPAs end up "recovering," what she wildly overthought in the early days, and why she believes the profession needs small and mid-sized firms to stay independent instead of selling to private equity. She also shares why AI without a strategy is just another subscription, and she takes on the scrappy vs. sophisticated lightning round, where she finds out if the data agrees with her. Chapters: 0:00 Welcome and the scrappy vs. sophisticated question 2:08 Growing up in a family tool company 6:02 What Well Balanced Accountants does today 8:08 From graphic design to accounting 13:49 Burnout at EY and the "recovering CPA" problem 19:34 Coaching from a parked car to starting a business 23:16 Finding the niche and what she overthought 31:01 Why independent firms should stay independent 35:14 AI strategy and the capacity diagnostic 42:31 Scrappy vs. sophisticated lightning round Connect with Erin: Well Balanced Accountants: https://wellbalancedaccountants.com LinkedIn: https://www.linkedin.com/in/cpacoacherin/ 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

A Charlotte marketing agency owner stopped getting the "What have you done for me lately?" question, raised her prices, and her clients were genuinely happy to pay more. Here is the 4-step process that got her there in a matter of days: Automated all her client data across every marketing platform Built a custom dashboard with every client's metrics and trends in one place Gave clients their own login so they can see their results Opened the door to advisory conversations backed by real numbers Raised prices once clients could see the strategy and roadmap working Learn more - https://www.pineappleanalyst.ai/fractional-cmos Questions - support@pineapplecf.com

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