Insights

Mark Dunaway spent 30+ years leading finance and operations for some of the country's top residential homebuilders - and then walked away from all of it to build a fractional CFO market from scratch on the Gulf Coast. As Area President and Fractional CFO for FocusCFO, he covers coastal Alabama and Pensacola, FL, a territory with zero prior FocusCFO presence and a market that often can't distinguish a CFO from a CPA. In this episode, Mark unpacks what strategic financial leadership actually looks like for small businesses, why hope is not a strategy, and how he's doing it all the old-fashioned way: five to seven face-to-face meetings a week. We cover Mark's path from a Baptist minister's son in southeastern Kentucky to bagging groceries, doing a six-hour solo Sunday radio show, and eventually running divisions for some of the largest homebuilders in the country. Along the way, he learned that great CFOs don't just live in spreadsheets - they have to understand the field, the bank's perspective, and the owner's vision all at once. If you're a small business owner trying to figure out whether you need a CPA, a bookkeeper, or something more, this episode is the clearest explanation you'll find. Chapters: 0:00:00 Intro and Mobile Mardi Gras Fun Fact 0:01:23 From Kentucky to the Coast: Mark's Background 0:02:57 What Fractional CFOs Do (and the Three-Headed Monster) 0:07:38 CFO Mindset vs. Accounting: Two Different Worlds 0:12:31 First Jobs: Bagging Groceries and a Six-Hour Radio Show 0:18:54 Building FocusCFO's Gulf Coast Market from Scratch 0:24:11 CFO vs. CPA: Keeping the Plates Spinning 0:27:18 Breaking Goals into Weekly Wins - Hope Is Not a Strategy 0:30:56 Finance's Role in Sales Strategy 0:33:05 Lightning Round: Scrappy vs. Sophisticated Connect with Mark Dunaway: Mark's LinkedIn: https://www.linkedin.com/in/mark-dunaway/ 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

Sean McColl is the founder of Trusted Business Advisors in Charleston, South Carolina. After more than 20 years as a top-performing sales leader - selling pagers in Washington, DC during the crack epidemic, building accounts at AT&T, and growing a promotional products company from a tiny startup to a successful acquisition - he went independent as an outside advisor. Today he works with owners, successors, and key leaders to bring the objectivity that insiders can't generate on their own, helping businesses find their blind spots and build sustainable growth. In this episode, Sean takes us from early childhood hustles - cutting lawns at 11, running a babysitting operation with his sister, and learning hard lessons as a 14-year-old dishwasher at an Italian restaurant - all the way through decades of high-stakes sales leadership and into what it really means to be a "business therapist" who helps CEOs sleep better at night. He shares why the very traits that make great entrepreneurs successful are often what hold them back as they scale, how the Who Not How principle shows up in his daily advisory work, and why an outside perspective is the most undervalued asset any growing business can have. Chapters: 0:00:00 Welcome + Sean's Entrepreneurial Roots 0:04:13 From Lawn Mowing to Babysitting Dynasties 0:07:02 First Real Job and the Restaurant Reality Check 0:09:58 Selling Pagers in 1990s DC - Scrappy by Necessity 0:18:26 Building Trusted Business Advisors 0:21:05 Coaching Owners Out of Their Own Way 0:29:17 Who Not How - Building the Right Team 0:31:32 The "Business Therapist" + Proving Value 0:34:31 Scrappy vs. Sophisticated Lightning Round 0:40:14 What's Next + Final Thoughts Connect with Sean McColl: LinkedIn: https://www.linkedin.com/in/seanmccoll1/ Website: https://trustedbizadv.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

Marcus Gaughan started his entrepreneurial journey at 19 with a portable eye therapy device that nearly launched with Iris as a strategic partner - until a single email ended it all. From there he built Minds on Fire through incubators, a CNC manufacturer marketplace, and a pandemic-era pivot that took him from Southern Ontario to investor conferences in the Middle East - picking up a client who happened to be the son of the governor of Riyadh along the way. Today Marcus runs Minds on Fire as a scaling agency focused on agentic AI, building custom tools that help businesses save time (defensive AI) and drive growth (offensive AI). His take: the real money is in the defensive side, and getting AI into your business doesn't have to break the bank or replace anyone. He's building a self-serve agent platform to prove it. Chapters: 0:00:00 Welcome & Meet Marcus Gaughan 0:00:36 Scrappy or Sophisticated? 0:02:35 Growing Up in Ontario's Startup Scene 0:05:36 First Startup: Portable Eye Therapy Device 0:11:01 A Decade of Business Partners 0:21:00 2020 Reset: Pandemic Pivot 0:24:38 Fake It Till You Make It in Bahrain 0:33:39 Minds on Fire: Agentic AI Agency 0:37:19 Offensive vs. Defensive AI 0:39:15 Lightning Round Connect with Marcus: https://agent.mindsonfire.ca/ https://www.linkedin.com/in/marcusgaughan/ 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

Priscilla McKinney is the CEO ("Momma Bird") of Little Bird Marketing, a LinkedIn influencer, a trained cultural anthropologist, and the host of her own podcast, 450-plus episodes deep. She joins Jack to unpack her take on the show's central question: you personally have to be scrappy, but your systems need to be sophisticated, meaning simple, clear, and pared down, not loaded up with bells and whistles. That distinction runs through everything from how she sets up her team's scope of work to how she rebuilt her agency from the ground up. From selling her mom's tulips door to door at age seven to surviving a 2011 tornado that leveled a third of her town, followed three weeks later by her studio burning to the ground, Priscilla has bet on herself again and again. She talks candidly about nearly losing the business three times, what entrepreneurship really costs a marriage and a family, and why being busy is not a badge of honor. Then Jack hits her with a scrappy vs sophisticated lightning round covering credit card timing games, scope creep, and the messiest client mistakes. Chapters: 0:00 Welcome and the Scrappy vs Sophisticated Question 3:23 Building a Team That Runs Itself 6:13 Born to Sell: From Tulips to the Drive-Thru 14:56 From Credit Card Hacks to Little Bird Marketing 19:04 Rising From the Ashes After the Tornado 20:19 Meet C Suite Stacy, the ICP That Never Changed 22:47 The Real Cost of Betting on Yourself 31:22 Boundaries, Trust, and the Entrepreneurial Curse 35:28 Lightning Round and Office Confessions 43:19 Final Verdict and Where to Find Priscilla Priscilla McKinney: LinkedIn: https://www.linkedin.com/in/priscillamckinney Website: https://littlebirdmarketing.com Resources and Freebies: https://littlebirdmarketing.com/resources Priscilla's Podcast: https://podcast.littlebirdmarketing.com/ 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

Joel Salomon spent years managing hundreds of millions of dollars on Wall Street, including a stretch at Citigroup where he generated positive returns in 2008 while the market fell 40%. Today he's a Prosperity Coach known as "The Money Doctor," helping heart-centered entrepreneurs (yoga teachers, energy healers, coaches) fix their money mindset and finally charge what they're worth. In this episode, Joel and Jack talk about the "money thermostat" that keeps people stuck at whatever income they grew up believing was normal, why undercharging is really a self-worth problem, and the wild story of launching his own hedge fund with zero committed capital and faking it until the money actually showed up. Chapters: 0:00 Intro and scrappy vs sophisticated 1:47 Growing up with entrepreneurial parents and a shifting money mindset 8:49 Early jobs, first money memories, and lessons on the value of a dollar 15:32 Landing the dream job at Citigroup right before the 2008 crash 21:41 Getting laid off and launching a hedge fund with no money lined up 25:01 Acting as if: faking momentum until the funding came through 27:54 From managing $700 million to coaching a $50-an-hour rate increase 31:54 The money mindset issue behind clients who don't track their own numbers 36:39 Gratitude, happy habits, and rewiring your brain for prosperity 39:59 Lightning round and final scrappy vs sophisticated verdict Joel Salomon: Website: https://www.salaurmor.com/ LinkedIn: https://www.linkedin.com/in/joel-salomon/ Facebook: https://www.facebook.com/JoelProsperitySalomon Facebook: https://www.facebook.com/thejoelsalomon Instagram: https://www.instagram.com/joelprosperitysalomon/ TikTok: search "joelprosperitysalomon" TEDx Talk: https://www.youtube.com/watch?v=0QgT2FmqmfA 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

Lindsey Wagnon left a thriving corporate marketing career in 2019 to build Lindsey Wagnon Marketing, and she has spent the years since helping small and mid-sized businesses break through what she calls the "Valley of Death" - the revenue plateau that stalls so many founders. In this episode, Jack and Lindsey dig into her Southwest Virginia upbringing, the sales instincts she picked up from her dad, why she walked away from a promising corporate marketing role six months before COVID hit, and how her practice evolved from full-service execution into true fractional CMO leadership. They also get into the difference between lead generation and client generation, the clients she wishes she'd never taken on, and a lightning round covering inboxes, docking stations, and office quirks (yes, there's a piano involved). Chapters: 00:00 - Intro and the scrappy vs sophisticated question 03:17 - Growing up in Southwest Virginia and her dad's sales instincts 08:22 - Networking anxiety and how to exit a conversation gracefully 12:16 - Leaving corporate in August 2019 to go out on her own 19:41 - Pushing back in corporate and why she'd be a bad employee now 24:05 - Finding her ideal client and what the Valley of Death looks like 29:14 - Systems, ownership, and lead generation vs client generation 35:36 - Lightning round: inbox habits, desk setup, and office quirks 43:51 - Scrappy vs sophisticated verdict and what's next for her business Connect with Lindsey Wagnon: https://www.linkedin.com/in/lrwagnon/ https://lindseywagnon.com https://www.instagram.com/lindseywagnonmarketing Connect with Jack Tompkins: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Mark Masquelier is the founder of Owl Point, a fractional CFO and COO advisory firm helping CEOs and boards navigate business growth through financial planning, cost-saving initiatives, profitability, and strategic organizational efficiency. Mark started his career at PricewaterhouseCoopers before moving through Chicago, Tucson, and now Oceanside, California, building his consulting practice through three iterations along the way. In this episode, Mark and Jack talk about what it really means to prove your value as a fractional executive every single week, why Mark always tries to make himself replaceable, and how a stint in stand up comedy and a Saturday morning radio show became some of his scrappiest lead generation tools. They also dig into contracts versus trust, the ants that humbled his RV lifestyle, and how OwlPoint got its name. Chapters: 00:00 Introduction and fun fact about Oceanside 01:14 Scrappy on the inside, sophisticated on the outside 02:37 Six weeks in an RV and an ant invasion 09:40 Growing up one of six entrepreneurial siblings 16:33 From CPA to fractional CFO and COO 18:02 Proving weekly value to CEOs and boards 24:38 Scrappy marketing: flyers, cold calls, and a radio show 30:00 Naming OwlPoint and the CFO to COO pivot 34:20 Lightning round: contracts, mornings, and cracked screens 43:41 Closing thoughts and where to find Mark Mark Masquelier LinkedIn: https://www.linkedin.com/in/mark-masquelier-cpa-296984196/ Consulting: https://owlpoint.net/ 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

Andy Brown grew up carrying shingles up a ladder at eleven years old on his family's roofing crew in North Louisiana. Thirty years later, he's a Fractional COO and Executive Coach who built LULO Coaching from zero to eighteen clients in three months, then had to figure out how to scale a coaching business without burning himself out in the process. In this episode, Andy walks through his path from Walmart shop manager at twenty years old to commercial roofing COO to founder, the exact three-step process he used to land his first clients after getting laid off, and why he decided to give away half his revenue to hire other coaches instead of staying a solo practitioner. He also breaks down the faith-based operating system he's building to fill gaps he sees in EOS, and previews the executive forums LULO is launching this year as a lower-time-commitment alternative to groups like EO and Vistage. Chapters: 00:00 - Intro and scrappy vs sophisticated 00:58 - Growing up on job sites in North Louisiana 02:08 - Carrying shingles at eleven, roofing by thirteen 05:17 - Walmart, promoted at twenty, and his father's death 09:52 - Turning around a last-place store in six weeks 16:19 - Getting laid off and starting LULO in seven weeks 19:08 - Three-step process for landing first clients 21:04 - Scaling past 18 clients by hiring other coaches 24:19 - Building Vital, a faith-based alternative to EOS 27:13 - Launching executive forums as a rival to EO and Vistage 34:01 - Lightning round: books, couches, and celebrating wins Andy Brown: LinkedIn: https://www.linkedin.com/in/andybrown220/ Website: https://lulocoach.com/ 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