CEO Journeys

Ray Drew started originating SBA loans at 23 with no book, no mentor, and no institutional support. He built the largest podcast in SBA lending, then a media network modeled on Barstool, then a video agency that failed, and in April 2026 he walked away from the W-2 entirely to become a partner at Lendesca.We get into the part nobody talks about: he ended his flagship podcast before he quit his job, not after, which is a strange order of operations for someone whose whole leverage was the audience. He explains why. We also cover the team he recruited at Truliant that went on to win a major industry award after he left and the obvious tension in a guy who built a brand as the indispensable human dealmaker joining a company selling AI-driven speed.

In 2015, Drew Carrick was an auditor at Grant Thornton who recorded a rap about public accounting. It went viral, and instead of firing him, the firm put him on its Innovation Council. Eleven years later he is still the Rapping CPA, and still arguing that accounting has a marketing problem rather than a math problem.We get into what it costs to build a career on one breakout moment, why he splits himself across three separate social accounts because the personas can't share a page, and what he learned standing in a live Netflix dating lineup on Pop the Balloon after a decade of controlling every frame of his own content. He also explains how a one-day consulting gig on FloQast's scripted comedy PBC turned into two weeks as technical advisor next to Danny Trejo and half the cast of The Office.If you've ever wondered whether the profession can actually rebrand itself, or whether the gimmick eventually becomes the ceiling, this one is worth your time.Find Petty Ca$h: https://www.instagram.com/therappingcpa/

Ben Starling III uncovers his secrets to gift-giving within the world of Philanthropy. As a professional fundraising consultant, Ben understands the ins and outs of managing donor relations and what it takes for non-profits to raise money. He’s also know Paul since Paul was around 14 years old. A friendship almost 30 years in the making. Ben has seen Paul grow up, get married, have children, start a career and eventually start VXIT.https://southernphilanthropy.com/

States Hines is now a Vistage leader and one of Paul’s mentors. Vistage is the world's largest executive coaching and peer advisory organization for chief executive officers, business owners, and key corporate executives. Founded in 1957, it operates in 40 countries and helps leaders solve business problems, improve decision-making, and scale their companies through structured group collaboration. States is in his 90s now and plans to live until 120+ years old. States has lived through vast change in business and technology as showcased on this episode where we talk about the evolution the madmen era business to AI. 

Sean and Kristen Shea built a business together. Kristen is the brains. Sean is the muscle. And they turn their house into a nightly Christmas show every year. In this episode, Sean and Kristen walk us through what it actually takes to build a business with your spouse, work out of your house, and stay sane doing both. They split roles cleanly: Kristen runs strategy, Sean runs execution. It works because the lanes are clear. The home-office angle is the part most husband-and-wife teams get wrong. Sean and Kristen talk through the upside (cost, control, time together) and the downside (boundaries, switching modes, never closing the laptop). The unfiltered version of what working out of your home with your spouse and partner is really like. Then there's the Christmas thing. They don't just decorate. They start months in advance and host nightly shows during the season. The kind of operation that has its own production schedule. Listen for what that obsession reveals about how they work together everywhere else. If you run a business with your spouse, want to, or have ever wondered how the couples who do it well actually pull it off, this is the conversation.

Solo episode. No guest. Just me, my story, and why this podcast exists. This show is built on conversations with founders, sales operators, family business owners, and the people who run them. This is the episode where I hand the mic to myself: where I came from, what I've learned along the way, and what made me hit record on this show in the first place. The thread running through every conversation here is the same one running through my own career: the people who win in business, in sales, in marriage, in everything, are the ones willing to look honestly at how they're wired and what it actually takes to grow. That's the conversation I want to keep having, on tape, with people worth learning from. If you've listened to a few episodes and wondered who's behind the questions, this is your answer. If this is your first one, start here. The rest of the show makes more sense once you know where the host is coming from. 

My wife Robin is the calm to my chaos. In this episode, we sit down for the conversation about marriage, mindset, and what it actually takes to keep a household running when one of you is wired like a CEO and the other is not. Robin is a stay-at-home mom to our two daughters, Bethany and Gwen, both 6th graders she homeschools. She runs our household. I run a company. Different jobs. Different temperaments. Same partnership. In this conversation, we go back to where we started. How we grew up. What we learned about growth mindset along the way, and what we got wrong. And what it actually feels like, day to day, to be the easygoing one married to someone running at full throttle. If you're a founder, a CEO, or just a Type-A operator, your spouse has a perspective on you that you don't get to hear out loud very often. This episode is that perspective, and the conversation that comes from finally sitting down to have it on record.

Anthony Bobba the serial entrepreneur! Finance. Insurance. After-intimacy wipes. Yes, really. A serial entrepreneur who's wired to win. Some people sell because they need to. Anthony sells because he can't not. In this episode, he walks us through a career that's moved through finance, insurance, and yes, after-intimacy wipes. The product changes. The operator doesn’t. What makes Anthony interesting isn't the variety. It's what the variety reveals. The category is irrelevant. The competitive instinct is the asset. He picks a market, learns the language, and goes. The win is the win. If you've ever wondered whether great salespeople are made or born, Anthony's case argues for born. Wiring matters. So does loving the scoreboard.

Keith Carley swept the shop floor at Air Compressor Works. Then he ran the company. Then he sold it. The family business arc, told straight. In this episode, Keith walks through what it actually looks like to grow up inside a business his father and uncle built from nothing. The lessons came on the floor: show up early, work harder than anyone else in the room, and the rest sorts itself out. Decades later, Keith took over Air Compressor Works. Years after that, he sold it. The conversation goes where most family-business stories don't: what changes when you stop being the owner and start being the operator inside someone else's structure. Keith is still in the seat, but the equity belongs to a larger partner now. That's a different job. Different incentives. Different conversations at home. If you grew up in a family business, you've thought about the exit. If you're staring down a sale right now, you've thought about it harder. Keith has lived both sides.