365 Driven | Entrepreneurship

Hosted by Tony Whatley

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440

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Aug 2026

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The 365 Driven Podcast helps entrepreneurs, business owners, executives, and aspiring leaders build successful businesses and fulfilling lives. Host Tony Whatley interviews top entrepreneurs, CEOs, athletes, authors, and industry leaders while sharing practical strategies for entrepreneurship, business growth, leadership, personal development, wealth creation, and success mindset.

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September 21, 2026Episode 4471 hr 16 min

What Business Should You Start? - with Tony Whatley - EP 447

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

September 7, 2026Episode 4461 hr 5 min

The Cost of Ego - with Eric Oberembt - EP 446

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 F ck 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

September 2, 2026Episode 44552 min

She Scaled to $10 Million in 3 Years - with Jesse Jackson - EP 445

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

August 24, 2026Episode 44441 min

Visualization: See It, Build It - with Tony Whatley - EP 444

What if the goals you're chasing aren't out of reach—you just haven't trained your mind to recognize the path to them yet? In this episode of the 365 Driven Podcast , host Tony Whatley explores the power of visualization and why creating a clear picture of your future can influence the opportunities you notice, the decisions you make, and the actions you take. But this isn't about simply wishing for success. Tony explains why visualization only becomes powerful when it's paired with consistent action, patience, and the willingness to keep moving forward when results aren't immediate. Drawing from his own life, Tony shares how vision boards have been part of his mindset since childhood and tells the stories behind goals that took more than a decade to become reality—including owning the exact types of dream cars he once pictured when they seemed financially impossible. He also breaks down the concept of the Reticular Activating System (RAS) and how setting specific goals can help you become more aware of opportunities, people, information, and resources that may move you closer to what you want. For entrepreneurs, Tony takes the conversation even deeper by introducing the idea of "significance value." Business owners are constantly forced to prioritize what is urgent and important, but some of the most transformational work you can do today may not produce results for months—or even years. Tony uses his own bestselling book as an example of how completing something that wasn't necessarily urgent ultimately changed the trajectory of his career, opening doors to stages, interviews, coaching opportunities, and greater influence. This episode is a reminder that entrepreneurship is a long game. The actions you take today may seem small, but when you combine a clear vision with relentless consistency, those actions compound. Five or ten years will pass either way—the question is who you'll become and what you'll have built when you get there. Key Highlights: The power of visualization in achieving goals How vision boards keep goals top of mind Using your RAS to recognize opportunities Why visualization must be paired with action The importance of consistency and patience Understanding the "significance value" of your work Why most people quit too soon How small daily actions create long-term success Connect with Tony Whatley: Website: 365driven.com Instagram: @365driven Facebook: 365 Driven

August 11, 202658 min

Build a Strong Personal Brand - with Henry Sims - EP 443

What if the reason your business isn't growing has nothing to do with your product—and everything to do with your personal brand? In today's crowded marketplace, trust has become one of the most valuable business assets you can build. In this episode of 365 Driven, host Tony Whatley sits down with Henry Sims, personal branding strategist, marketing expert, and founder of HenrySims.com, to uncover the practical systems business owners can use to build authority, attract ideal clients, and create a brand that converts attention into revenue. Drawing from his engineering background and years spent helping build the internationally recognized personal brand of his late father, entrepreneur Brad Burton, Henry brings a refreshingly analytical approach to branding that replaces hype with proven strategy. Tony and Henry break down why personal branding isn't about becoming an influencer—it's about shortening the sales cycle by building trust before a prospect ever reaches out. They explore why authenticity consistently outperforms imitation, how entrepreneurs can identify the personality traits that make them memorable, and why trying to appeal to everyone is one of the fastest ways to become forgettable. Henry also introduces the "Character Diamond" framework, explaining how successful brands combine strengths, personality, purpose, and vulnerability to create genuine human connection. The conversation also tackles one of the biggest fears entrepreneurs face: putting themselves on camera. Tony and Henry discuss overcoming criticism, why the loudest critics are rarely your ideal customers, and how many of your biggest supporters are quietly watching behind the scenes. They reveal why long-form content like podcasts and YouTube videos are becoming increasingly valuable in today's AI-driven search landscape, and how business owners can turn one piece of content into an entire week's worth of marketing. Whether you're just beginning to build your personal brand or looking to generate more trust, leads, and sales, this episode delivers practical, actionable strategies that will help you stand out, connect with the right audience, and grow your business with confidence. Key highlights: Why personal branding is the ultimate business growth strategy. The Character Diamond framework for building an authentic brand. How to attract ideal clients by embracing your unique personality. Why trust—not followers—is the key to more sales. The 7-11-4 Rule for building credibility and shortening the sales cycle. How long-form content outperforms chasing viral posts. Overcoming the fear of criticism and showing up consistently. Creating a content system that builds authority without burnout. Connect with Henry Sims: Visit HenrySims.com to book a complimentary Brand Audit and discover how to build a personal brand that attracts the right clients. Follow Henry on Instagram @henrydsims Connect with Tony Whatley: Website: 365driven.com Instagram: @365driven Facebook: 365 Driven

August 3, 2026Episode 44241 min

Escape the Poor Mindset - with Tony Whatley - EP 442

What if the biggest thing holding your business back isn't the economy, your competitors, or rising costs—but your own mindset? In this solo episode of 365 Driven , host Tony Whatley challenges business owners and entrepreneurs to rethink how they view problems, success, and personal growth. Drawing from his own journey of growing up in a lower-middle-class family, working construction to pay his way through engineering school, and eventually building and selling multi-million-dollar businesses, Tony shares the mindset shifts that helped him escape scarcity thinking and create lasting success. Throughout the episode, Tony explains why so many people stay trapped in a "poor mindset" by giving too much emotional energy to small problems while ignoring the bigger opportunities that can transform their lives. Using practical examples—from arguing over gas prices to stressing about restaurant menus—he illustrates how successful entrepreneurs learn to assign value to their problems, focus on what they can control, and continually "graduate" to solving larger, higher-value challenges. You'll also discover why increasing your income is less about working harder and more about developing the skills to solve bigger problems, why companies pay more for people who can manage greater risk, and how investing in knowledge—not excuses—creates long-term wealth. Tony also dives into the principles of Stoicism, emotional discipline, and personal accountability, offering practical strategies to stop reacting to distractions and start responding like the person you aspire to become. If you're a business owner who wants to stop wasting energy on low-value distractions, build a stronger mindset, and focus on the opportunities that truly move the needle, this episode will challenge the way you think—and help you level up both your business and your life. Key highlights: How to escape a poor mindset and think like a successful entrepreneur. Why small distractions keep business owners from bigger opportunities. The concept of "graduating" to solving higher-value problems. How emotional discipline and Stoicism improve business decision-making. Why increasing your income starts with developing valuable skills. The connection between solving bigger problems and earning more. How to stop wasting energy on things outside your control. Practical mindset shifts to create more focus, peace, and long-term success. Connect with Tony Whatley: Website: 365driven.com Instagram: @365driven Facebook: 365 Driven

July 20, 2026Episode 44152 min

From MLB to Movies - with Daryl Jones - EP 441

What if your greatest setback could become the foundation for your biggest comeback? Every entrepreneur will face adversity—but the ones who succeed are those who refuse to let failure define them. In this episode of 365 Driven , host Tony Whatley sits down with former Major League Baseball player, motivational speaker, actor, performance coach, and entrepreneur Daryl Jones . After being drafted by the St. Louis Cardinals out of high school and reaching the Major Leagues, Daryl appeared to be living the dream. But career-ending injuries, personal struggles, financial hardship, and losing everything forced him to reinvent himself from the ground up. Today, he inspires audiences through public speaking, coaches young athletes, and continues building a career in film while helping others develop confidence and resilience. In this powerful conversation, Tony and Daryl explore what it takes to rebuild your identity after losing the career or business you thought would define your life. Daryl shares the emotional realities of transitioning from professional sports, overcoming depression, addiction, and setbacks, and ultimately choosing to take responsibility for creating a better future. His story is a reminder that success isn't about avoiding failure—it's about deciding to keep moving forward when everything around you falls apart. Business owners will also gain practical leadership lessons on building confidence through small, repeatable actions, focusing on strengths instead of weaknesses, and embracing the struggles that inevitably come with growth. Tony and Daryl discuss why confidence is built through consistent action, how great coaches position people to maximize their unique abilities, and why simplicity often creates the greatest momentum when you're feeling stuck. The conversation also dives into public speaking, personal branding, networking, acting, and the importance of continually reinventing yourself as new opportunities arise. Whether you're recovering from a major setback, navigating uncertainty in your business, or simply looking for the motivation to take your next step forward, this episode will remind you that your past doesn't determine your future. Sometimes your greatest comeback begins the moment you decide to stop looking backward and start building what's next. Key highlights: From Major League Baseball to public speaking and acting. How to rebuild your life after career-ending setbacks. Why confidence is built through small, consistent actions. The power of focusing on your strengths instead of your weaknesses. Leadership lessons from sports that apply to business. Turning failure into fuel for your next chapter. Reinventing yourself after losing your identity. How resilience creates long-term success. Connect with Daryl Jones: Instagram: @thedaryljones Connect with Tony Whatley: Website: 365driven.com Instagram: @365driven Facebook: 365 Driven

July 13, 2026Episode 44053 min

Invest In Yourself - with Adam Lamb - EP 440

What if the biggest thing holding your business back isn't your strategy—but your mindset? Success in business isn't built on tactics alone. It's built on discipline, self-awareness, leadership, and the willingness to invest in your own growth. In this episode of 365 Driven, host Tony Whatley welcomes entrepreneur, healthcare innovator, business consultant, and leadership expert Adam Lamb. As the founder of a nationwide telemedicine company, advisor to healthcare organizations, partner in launching Life Force with Tony Robbins, and consultant to multi-million-dollar healthcare businesses, Adam has spent years helping entrepreneurs and medical professionals build companies that create lasting impact. Adam shares his remarkable journey from barely graduating high school and working in Detroit nightclubs to becoming one of the most respected consultants in the healthcare industry. Along the way, he explains how challenging limiting beliefs, staying relentlessly focused on one area of expertise, and continuously investing in personal development opened doors he never imagined possible. For business owners constantly chasing the next opportunity, Adam offers a compelling case for mastering your lane before expanding into new ventures. Tony and Adam also dive into the characteristics of authentic leadership, discussing why integrity matters more than image, how successful entrepreneurs evaluate partnerships, and why taking ownership of your life is the foundation for long-term success. They explore the importance of hiring mentors who align with your current stage of growth, avoiding information overload, and understanding the true return on investing in yourself. The conversation also covers entrepreneurship, local leadership, stoicism, accountability, and building a life where your personal values and business decisions are fully aligned. Whether you're launching your first company, scaling an existing business, or searching for greater clarity in your leadership journey, this episode is filled with practical wisdom that will help you focus on what truly matters. If you're ready to stop making excuses, lead with authenticity, and build a business that reflects your values, this conversation is one you won't want to miss. Key highlights: Why authentic leadership starts with leading yourself first. The mindset shift that turns excuses into opportunities. How to stay focused instead of chasing every business idea. Why investing in yourself delivers the highest return. The importance of choosing mentors for your current stage of growth. How personal accountability drives business success. Building a business that aligns with your values and purpose. Practical strategies for creating long-term success and freedom. Connect with Adam Instagram: @AdamLamb33 Connect with Tony Whatley: Website: 365driven.com Instagram: @365driven Facebook: 365 Driven

July 6, 2026Episode 43956 min

Do It Scared - with Frank Sell - EP 439

What if the only thing standing between you and the business you've always wanted is the courage to take the first step? Many aspiring entrepreneurs spend years waiting for the perfect time, the perfect plan, or someone else's permission to start. But what if success isn't about having all the answers—it's about taking action before you feel ready? In this episode of 365 Driven, host Tony Whatley sits down with entrepreneur Frank Sell, founder and CEO of Get Shit Done Coffee, successful paintless dent repair business owner, and lifelong builder of multiple brands and businesses. From leaving the security of a steady welding career to creating thriving companies fueled by grit, resilience, and relentless self-improvement, Frank shares the lessons that transformed his life and entrepreneurial journey. Tony and Frank dive deep into what it really takes to bet on yourself, overcome fear, and build a business from the ground up. Frank explains why most people are waiting for validation they don't need, why the marketplace—not opinions—should determine your next move, and how taking imperfect action creates opportunities that careful planning never will. You'll also hear the remarkable story behind the accidental creation of Get Shit Done Coffee, proving that some of the best business ideas come from simply paying attention and saying "yes" when opportunity appears. The conversation goes far beyond entrepreneurship, exploring the importance of personal development, choosing the right relationships, protecting your reputation, and creating a legacy that extends far beyond financial success. Frank shares powerful analogies from motocross that perfectly illustrate why entrepreneurs must "do it scared until they can do it skilled," while Tony offers practical wisdom on overcoming fear, embracing growth, and building a life of purpose. Whether you're still working a traditional job, preparing to launch your first business, or looking for renewed motivation to keep pushing forward, this episode is packed with practical advice, inspiring stories, and mindset shifts that will challenge you to stop waiting and start building the future you truly want. Key highlights: Why waiting for permission is holding entrepreneurs back. How Frank Sell turned a trade into multiple successful businesses. The mindset shift that helps you overcome fear and take action. The surprising story behind the creation of Get Shit Done Coffee. Why personal development is every entrepreneur's greatest investment. Lessons on building a strong personal brand and lasting legacy. How to recognize opportunities others overlook. Practical advice for anyone ready to leave their 9-to-5 and start a business. Connect with Frank Sell: Learn more about Frank's entrepreneurial journey and check out GetShitDoneCoffee.com for his coffee brand. Connect with Tony Whatley: Website: 365driven.com Instagram: @365driven Facebook: 365 Driven

June 29, 2026Episode 4381 hr 1 min

AI Is Your Competitive Edge - with Austin Armstrong - EP 438

What if the biggest competitive advantage your business could gain this year costs less than dinner for two? Artificial intelligence is no longer a futuristic concept—it's a tool that forward-thinking entrepreneurs are using today to save time, increase revenue, and outpace the competition. In this episode of 365 Driven , host Tony Whatley sits down with digital marketing expert, AI educator, and SaaS founder Austin Armstrong to explore how business owners can leverage AI without getting overwhelmed by the endless stream of new tools and trends. With more than 20 years of digital marketing experience and millions of followers across social media, Austin has become one of the most trusted voices in the AI space by helping entrepreneurs cut through the hype and focus on what actually works. Together, Tony and Austin dive into practical strategies for adopting AI, building a personal brand, and creating content that generates real business—not just vanity metrics. Austin shares why entrepreneurs should stop fearing failure, embrace experimentation, and learn to pivot quickly when the market speaks. You'll also discover how AI agents are transforming the way businesses operate, why conducting a time audit may be the smartest first step before investing in new technology, and how entrepreneurs can automate repetitive work while focusing on high-value activities that drive growth. The conversation also explores the future of AI, from autonomous agents and robotics to the evolution of marketing, content creation, and software itself. Whether you're just beginning to explore AI or you're looking to gain a competitive edge, this episode delivers actionable insights that can help you work smarter, market more effectively, and future-proof your business. If you're a business owner who wants to stay ahead instead of getting left behind, this episode is packed with strategies you can start applying today. Key highlights: Why AI is the biggest competitive advantage for entrepreneurs today. How AI agents can save hours of work every week. The simple time audit that reveals what to automate first. Why consistency beats going viral on social media. How to build a personal brand that attracts high-paying clients. The mindset shift every entrepreneur needs to embrace AI. Austin's predictions for the future of AI, automation, and robotics. Practical AI tools every business owner should start using today. Connect with Tony Whatley: Website: 365driven.com Instagram: @365driven Facebook: 365 Driven Connect with Austin Armstrong: Website: AustinArmstrong.ai