365 Driven | Entrepreneurship

Host Tony Whatley interviews Brian Bogert about what it looks like when real freedom arrives—beyond money or status—and how it comes from living without the need to justify, protect, defend, or prove yourself. Brian shares his origin story of being run over by a truck at age seven, losing his left arm and enduring 24 surgeries, and how his parents' approach shaped his philosophy of embracing pain to avoid suffering. They discuss identity, vanity versus self-care, and Brian's "strong spine, soft front" framework, including how protection creates disconnection. Tony reflects on leaving a prestigious corporate oil-and-gas career after a near-fatal racing accident to pursue impact, and they close with questions and a calibration tool: whether your words, actions, and behaviors move you closer to or further from who you are and what you want.   00:00 Welcome 00:47 Brian's Origin Story 01:17 The Walmart Accident 02:10 A Nurse's Choice 04:20 Surgeries and Recovery 06:09 Parents and Resilience 08:36 How Upbringing Shapes Us 12:05 Scars Tattoos and Identity 17:36 Vanity as Self Care 21:09 Freedom Strong Spine Soft Front 24:28 Learning From Past to Grow 28:07 Victim Mindset and Change 30:44 No More Excuses 31:57 Protection Disconnects 32:32 Two Questions Pause 33:00 Marriage Trigger Example 34:48 Redefining Real Freedom 34:50 Success Without Freedom 36:53 Losses And Rebuild 39:49 Choosing Values Daily 40:53 Golden Handcuffs Trap 45:09 Leaving Corporate Leap 50:29 Facing Mortality Calmly 52:16 Simplicity In Chaos 54:45 Freedom Calibration 56:49 Self Actualization Journey 58:12 Resources And Farewell

Back in the studio after a vacation to New York City and a cruise to Bermuda! Tony Whatley explains why many people avoid world travel, sharing how he overcame a scarcity mindset from growing up with limited means with help from his wife, who was raised traveling.   Having visited 38 countries and 48 U.S. states, he outlines travel's benefits: richer experiences, broader perspective, personal growth, less judgment, stronger relationships, mental resets, and creativity—illustrated by lessons from time spent in Africa and work in France and the UK. He argues waiting until retirement can create regret, citing a coworker who died before traveling.    He announces 2027 Iceland and 2028 Vietnam/Cambodia cruises and mentions an upcoming Japan trip.   00:00 Back From Vacation 00:56 Travel Scarcity Mindset 03:14 Why Americans Avoid Travel 05:18 Lisa Sparks Wanderlust 06:36 Experiences Over Stuff 08:13 History Through Travel 09:31 Africa Happiness Lesson 12:54 France Work Life Balance 19:31 Tech Makes Travel Easy 23:56 Relationships Reset Creativity 29:10 Dont Wait To Retire 31:39 Money Returns Time Doesn't 33:06 The Someday Trap 35:16 Travel by Life Stages 37:35 Experiences Beat Screens 39:07 Plan Ahead Travel Smarter 41:21 Avoid Overpacked Itineraries 43:28 Flexible Routes No Backtracking 47:53 Unplug and Stay Present 49:51 Spend Less Enjoy More 50:53 Points Strategy for Travel 54:15 Upcoming 365 Driven Group Trips 55:20 Stop Postponing Life  

What if the business idea you're excited about could never actually give you the income, freedom, or lifestyle you want? In this solo episode of the 365 Driven Podcast, host Tony Whatley breaks down one of the most important questions every entrepreneur eventually faces: What business should I start—and is the business I'm already running actually the right one? Rather than chasing trends, getting attached to an exciting idea, or building a company that ultimately becomes another job, Tony shares a practical framework for evaluating business opportunities based on where you actually want to go. Tony explains why ideas alone have very little value without execution and challenges entrepreneurs to start with the end in mind. What income are you trying to create? How much time freedom do you want? Do you eventually want to sell the company, build a family legacy, or simply replace your current expenses? Your destination should determine the business vehicle you choose. Throughout the episode, Tony walks through how to brainstorm and evaluate business ideas using your existing skills, knowledge, resources, relationships, and interests. He also explains why entrepreneurs need to stop obsessing over revenue and instead understand profit, margins, scalability, and the basic math behind their business model. A million-dollar company means very little if there's no profit left at the end of the year. For established business owners, Tony offers a different challenge: Would you start your current business again today knowing what you know now? He explores profitability, time investment, scalability, industry changes, the self-employment trap, and the sunk-cost thinking that can keep entrepreneurs committed to the wrong path for too long. Most importantly, this episode is about taking action. Your dream business may be several businesses away, but you can start building the staircase today. Instead of spending months perfecting a plan, determine which opportunity aligns with your goals, run the numbers, identify your next move, and execute. If you're considering starting a business, questioning the one you already own, or looking for a smarter way to evaluate your next opportunity, this episode will give you a practical framework for deciding what deserves your time, money, and energy. Key highlights: How to choose the right business idea Why ideas are worthless without execution Aligning your business with your goals Why profit matters more than revenue How to test an idea with simple math Avoiding the self-employment trap When to pivot or walk away Turning business ideas into action Connect with Tony Whatley: Website: 365driven.com Instagram: @365driven Facebook: 365 Driven

What if the biggest thing standing between you and your next level of success isn't a lack of knowledge, opportunity, or resources—but your own ego? In this episode of the 365 Driven Podcast, host Tony Whatley sits down with Eric Oberembt, CEO of D&M Roofing and Siding and host of the Be Authentic or Get the Fck Out* podcast, for a raw conversation about overcoming adversity, building better relationships, protecting your time, and becoming the kind of leader capable of reaching the next level. Eric shares his remarkable transformation from facing a fourth felony DUI, addiction, and the possibility of prison to rebuilding his life and becoming a successful entrepreneur. His turning point came when he finally realized that instead of believing he had all the answers, he needed to stop talking, start listening, and become willing to learn from people who had already walked the path he wanted to take. Tony and Eric translate those hard-earned lessons directly into entrepreneurship. They discuss why the people you surround yourself with can either accelerate your growth or hold you back, and Eric shares how he intentionally changed his circle by seeking relationships with people who challenged him to become better. They also explore one of an entrepreneur's most valuable resources: time. Eric explains why being constantly busy isn't the same as being productive and why successful leaders must establish boundaries, control access to their time, and focus on becoming more efficient and effective. Ultimately, success isn't just about accumulating more money—it's about creating the freedom and choices that money can provide. Most importantly, Eric challenges entrepreneurs to drop their egos and ask for help from people who have actually achieved what they're trying to accomplish. Asking for advice isn't enough—you also have to listen, execute, and be willing to change. This episode is a powerful reminder that growth often begins when you stop trying to be the smartest person in the room. Whether you're struggling with your business, relationships, health, or direction in life, sometimes the next breakthrough starts by getting quiet, asking better questions, and actually listening to the answers. Key Highlights: Why growth starts with dropping your ego How your inner circle impacts success The importance of asking for help Why listening is a leadership advantage How to protect your time and energy Why busy doesn't mean productive Redefining success around freedom and choice Turning adversity into personal and business growth Connect with Eric Oberembt: website: ericoberembt.com Connect with Tony Whatley: Website: 365driven.com Instagram: @365driven Facebook: 365 Driven

Host Tony Whatley interviews Jesse Jackson, CEO of Mango Automotive, which scaled to over $10M revenue in its first three years and now operates eight shops across New Mexico, Arizona, and Texas. Jackson shares her path from environmental engineering to software product leadership, selling an automotive detail shop management app in 2021, and pivoting into brick-and-mortar auto repair due to an aging owner base and opportunity to improve customer experience (the "pink wall effect," clean lobbies). She explains why software profitability can suffer from heavy customization, how Mango uses AI and custom internal tools to centralize metrics and task checklists, and how acquisitions require systems to function without constant owner presence. Jackson discusses sourcing off-market deals, frequent owner financing tailored to seller needs, focusing on shop size (6–7 bays minimum) and location, and retaining talent by offering benefits and growth opportunities through "Mango University," with a goal to reach nine figures in five years using added capital.  00:00 Meet Jesse Jackson 01:14 From Engineer to Software 02:51 Why Software Burns Out 03:36 Custom Tools With AI 06:36 Why the App Wasnt Profitable 09:27 Spotting the Shop Opportunity 11:40 Pink Wall Customer Experience 13:11 First Shop Christmas Sprint 17:00 Finding Deals Off Market 21:33 Owner Financing Retirements 22:02 Scaling Fast Eating Glass 23:30 Systems Slow Day Checklist 26:13 McDonalds Ops Lessons 27:11 Extreme Shop Organization Ideas 27:53 Shop Workflow Mindset 28:43 Checklist Driven Consistency 29:30 Acquisition Sweet Spots 31:27 Labor Shortage Reality Check 32:37 Benefits First Hiring 37:20 Pricing Above Bottom 38:01 Promoting From Within 39:38 Growth Mindset Training 41:51 Culture In Acquisitions 44:06 Nine Figure Growth Plan 46:12 Just Start And Delegate 49:22 Hiring Before You Can 51:10 Closing And Contact Info