How Owners Sabotage Their Own Success | Episode 340

If you are ready to level up personally and professionally, go to joinrbo.comVery few are willing to become the person required to make that true.In this episode, Trevor breaks down why setting big goals isn’t the problem—your daily standards are. Instead of chasing outcomes, this conversation challenges you to focus on the actions, habits, and environments that actually create results over time.This is a no-BS episode about discipline, consistency, and why the next six months matter more than the next six years.If you’ve been busy but not moving forward… this one will hit.

Leadership isn’t motivational quotes and applause. It’s pressure, loneliness, conflict, and responsibility — and most people aren’t prepared for that reality.In this solo episode, Trevor Cowley breaks down 10 harsh truths every leader needs to hear if they actually want to grow, scale, and sustain success. Whether you run a business, lead a team, or are trying to become a better version of yourself, this episode cuts through the fluff and tells you what leadership really costs — and why it’s still worth it.This is about standards, discipline, perspective, and learning how to carry the weight when things get heavy.If you are ready to level up personally and professionally, go to joinrbo.com

In this episode, Justin Brennan breaks down how he went from watching his family lose everything in a $60M bankruptcy to rebuilding a $200M multifamily portfolio. Trevor and Justin dive into the mechanics of commercial real estate, how to protect yourself in volatile markets, and the deeper psychological work required to level up in business.This isn’t just a real estate episode. It’s about breaking generational patterns, rewiring the subconscious, and understanding how big players build, and keep, wealth.If you are ready to level up personally and professionally, go to joinrbo.com

In this solo episode, Trevor breaks down the real reason most business owners stay stuck: they sabotage their own team. From micromanaging to refusing to document systems to hiring without standards, Trevor walks through the ten deadly sins that destroy employee performance and keep your business chained to you. If you want a company that can grow without you, this episode is a blueprint for how to stop being the bottleneck and start building a team that actually wins.If you are ready to level up personally and professionally, go to joinrbo.com

In this episode, Trevor sits down with Jacob Lawson to break down what it really takes to reinvent yourself, push through discomfort, and build a life that actually means something. Fresh off a half-marathon they ran together that morning, the conversation dives into discipline, mindset rewiring, escaping the collapsing middle class, and the brutal but necessary truth about honoring your commitments.This is a conversation about becoming the person capable of the life you want—no shortcuts, no sugarcoating.If you are ready to level up personally and professionally, go to joinrbo.com

In this episode, Trevor sit down with Inner Circle member and HVAC business owner Carter Henry, who went from drowning in debt, self-sabotage, and burnout to building momentum, scaling his team, and finding real purpose. This is the story of a business owner who hit rock bottom, cut out the excuses, rebuilt his standards, and transformed his life and business in under a year.If you’ve ever felt stuck, overwhelmed, or one bad month away from shutting the doors. This is the episode you need to hear.If you are ready to level up personally and professionally, go to joinrbo.com

In this solo episode, Trevor Cowley breaks down what to do when you hit a low point in business and life.
Whether you’re mentally burned out, feeling stuck in a loop, or questioning your purpose, this episode is your wake-up call.Trevor dives into how to regain momentum, shift your perspective, and reignite the fire that once drove you.
He reminds listeners that discipline, commitment, and purposeful friction are the only way out of mediocrity and into your true potential.If you are ready to level up personally and professionally, go to joinrbo.com

In this solo episode, Trevor breaks down real-world tax strategies that most accountants won’t tell you about. From choosing the right business entity to leveraging legal tax loopholes, this episode is packed with information that can help you keep more of the money you earn. Trevor explains what questions to ask your CPA, how to structure your business the smart way, and what moves you can make before tax season to protect your profits.This isn’t financial advice—it’s insight from someone in the trenches who’s tired of watching business owners overpay Uncle Sam.If you are ready to level up personally and professionally, go to joinrbo.com

Every business hits that wall—the moment when momentum slows, motivation fades, and you start questioning if you’re even built for this. Trevor breaks down why regression is not the end, but the necessary reset before your next breakthrough.Through raw stories from his own businesses, he explains how struggle, friction, and even doubt can be the greatest teachers—if you hold the line and stay in the fight long enough to adapt.This episode is a blueprint for any entrepreneur who feels stuck, frustrated, or ready to throw in the towel.If you are ready to level up personally and professionally, go to joinrbo.com

What happens when you build a 5,000+ employee company and sell it?
Trevor sits down with entrepreneur and former fleet management CEO Kelly Meredith to unpack his journey — from coaching football to creating an industry-changing business, selling it to private equity, and rediscovering purpose through his new Icelandic Marine Collagen venture.This episode dives deep into how ambition, discipline, and integrity can take you to the top — and what happens when you realize money isn’t the real measure of success.If you are ready to level up personally and professionally, go to joinrbo.com