The Cost of Ego - with Eric Oberembt - EP 446
365 Driven | Entrepreneurship
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...
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She Scaled to $10 Million in 3 Years - with Jesse Jackson - EP 445
365 Driven | Entrepreneurship
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...
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Visualization: See It, Build It - with Tony Whatley - EP 444
365 Driven | Entrepreneurship
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...
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Build a Strong Personal Brand - with Henry Sims - EP 443
365 Driven | Entrepreneurship
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...
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Escape the Poor Mindset - with Tony Whatley - EP 442
365 Driven | Entrepreneurship
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...
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From MLB to Movies - with Daryl Jones - EP 441
365 Driven | Entrepreneurship
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...
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Invest In Yourself - with Adam Lamb - EP 440
365 Driven | Entrepreneurship
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,...
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Do It Scared - with Frank Sell - EP 439
365 Driven | Entrepreneurship
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...
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AI Is Your Competitive Edge - with Austin Armstrong - EP 438
365 Driven | Entrepreneurship
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...
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The Truth About Peptides - with Alex Spinoso - EP 437
365 Driven | Entrepreneurship
What happens when the “safe” career path starts to feel like a prison? In this episode of 365 Driven, host Tony Whatley sits down with Dr. Alex Spinoso, a physician, entrepreneur, and founder of Genesis Lifestyle Medicine. Alex brings a powerful combination of medical expertise and real-world business experience, holding both a medical degree and an MBA. After beginning his career as a physician in the California prison system, Alex quickly realized that the traditional path of a stable six-figure career, pensions, and predictable comfort was not enough. He wanted challenge, growth, and...
info_outlineWhat if the biggest thing holding your business back isn’t your competition — but your fear of charging what you’re truly worth? In this powerful solo episode of the 365 Driven podcast, host Tony Whatley tackles one of the most uncomfortable yet critical topics for entrepreneurs: raising your prices with confidence.
Tony breaks down the psychology behind why so many business owners undercharge, delay price increases, and attract difficult customers by trying to compete at the bottom of the market. From money mindset limitations to fear of customer reactions, he explains how entrepreneurs unknowingly sabotage their own growth by pricing based on personal comfort rather than the actual value they create.
Throughout the episode, Tony shares real-world examples from his own entrepreneurial journey and client success stories — including attorneys, laboratory owners, and service providers who dramatically increased profits simply by repositioning their value and raising their rates strategically. He also reveals why cheap customers often demand the most, while premium clients respect expertise, efficiency, and quality.
You’ll learn:
- How to know when it’s time to raise your prices
- Why waiting too long silently destroys profit margins
- The connection between pricing and perceived value
- How premium pricing attracts better customers
- The biggest mistakes business owners make when announcing price increases
- Why confidence matters more than apologizing
If you’ve been overworked, underpaid, or hesitant to charge what your expertise deserves, this episode will challenge your mindset and help you step into the role of a true CEO. Tony delivers practical strategies, tough love, and actionable insights designed to help entrepreneurs build stronger, more profitable businesses without burnout.
Connect with Tony Whatley:
- Website: 365driven.com
- Instagram: @365driven
- Facebook: 365 Driven