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ep36 What got us here Wont get us where we need to go next

CEO Bros - After Hours

Release Date: 10/17/2025

Entrepreneur's Journey - Rory Rubin, CEO of S.I. Container Builds show art Entrepreneur's Journey - Rory Rubin, CEO of S.I. Container Builds

CEO Bros - After Hours

Social worker turns 26 million stranded shipping containers into housing. Rory's husband offered a solution to her midlife crisis: "Just buy a sports car." She started a manufacturing company instead. Seven years later, she's built a two-story structure on Lake Michigan. This is episode 41. When the easier path isn't the right one. *YOU'LL DISCOVER* • Why 26 million shipping containers sit in US graveyards • How a clinical social worker became a manufacturing CEO • The Navy Pier project that made Chicago history • Why containers weren't legal for housing until 2018 *WHAT ACTUALLY...

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Productive Friction show art Productive Friction

CEO Bros - After Hours

Sales vs. Legal. Operations vs. Compliance. You vs. your Co-founder at 2am. Brad encourages friction. Brian lets it run longer than most CEOs. They both know something most entrepreneurs miss: the uncomfortable tension between departments isn't killing your business. Avoiding it is. Sales wants to close the deal. Legal wants to protect the company. Operations needs flexibility. Compliance needs rules. Most CEOs try to eliminate the friction. Brad and Brian? They promote it. This is episode 40: Let’s Get Ready To Rumbbbbbbbble! *YOU'LL DISCOVER* • Why "copacetic" environments produce lazy...

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Pros and Cons of Remote Work ep 39 show art Pros and Cons of Remote Work ep 39

CEO Bros - After Hours

Remote work introduced problems offices never had. Dogs barking. Contractors arriving. Kids at the door. Cameras off or multitasking? Working in PJs or logging extra hours? Brad thinks remote work kills his 550-employee culture. Brian cleaned out VHT's fridge in March 2020 and never came back for two years. COVID forced the experiment. Some companies stayed remote. Others are dragging people back. AT&T doesn't have enough parking spaces. Microsoft's thriving. Brad can't imagine meetings with cameras off. This is episode 39. Remote versus in-office, and why nobody's figured it out. You'll...

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Intuitive vs Analytic decision making ep 38 show art Intuitive vs Analytic decision making ep 38

CEO Bros - After Hours

Making decisions fast? Making them careful? Or just frozen between the two? Brian spent three months analyzing a new product line nobody in the industry had ever done. Endless scenarios that led nowhere. He finally said screw it and pulled the trigger anyway. Now people ask him how he decided to do something nobody else can replicate. Brad runs the opposite problem. His team moves so fast they don't think through consequences. This is episode 38. How to know when to trust your gut and when to slow down. In this conversation, you'll discover: • The two questions that determine instinct versus...

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ep 37 Budgeting - It's a show art ep 37 Budgeting - It's a

CEO Bros - After Hours

Budget Battle Royale: The Smackdown Between Growth vs. Profit (+ The $250K Contest Catastrophe)* Two CEOs reveal the brutal truth about budgeting, why "set it and forget it" destroys businesses, and how to turn budget fights into innovation. Think you know how to budget? Think again. In this raw, unfiltered conversation, Brian and Brad (two CEOs who've built, scaled, and sold companies) destroy the myths around business budgeting and reveal why most entrepreneurs are doing it completely wrong. You'll discover: • Why the "baseline vs. zero-up" debate could make or break your company • The...

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ep36  What got us here Wont get us where we need to go next show art ep36 What got us here Wont get us where we need to go next

CEO Bros - After Hours

What got us here, won’t get us where we are going next.   The guys discuss the business philosophy that "What got us here won't necessarily get us there." The conversation focuses on the evolution of a growing business, emphasizing the need for change in leadership, systems, processes, and people to reach the next level of success. Both CEOs share personal examples. Ultimately, they conclude that bold, sometimes unpopular decisions are necessary for a company to scale effectively. This discussion centers on a fundamental challenge faced by every growing business: the skills,...

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ep 35 Do the Little Things Really Make or Break a Business? show art ep 35 Do the Little Things Really Make or Break a Business?

CEO Bros - After Hours

A spirited discussion about the critical importance of attention to detail in business. The guys share anecdotes, including a story about an easily forgotten rental car in Las Vegas and an example of poorly implemented office doors, to illustrate the consequences of overlooking small details. A central theme is the contrasting perspectives on leadership, with Brad emphasizing the need to "inspect what you expect" and Brian trusting employees to handle details, and they explore how details significantly influence the customer experience and overall business success, citing examples like the...

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ep 34 He said what?  The essentials of business presentations show art ep 34 He said what? The essentials of business presentations

CEO Bros - After Hours

Public Speaking for Business Leadership   This episode of ‘CEO Bros - after hours’ synthesizes key insights on public speaking as an essential leadership skill, derived from a discussion among business leaders and a communications expert. The central argument is that while public speaking is a common and significant fear, it is a non-negotiable and masterable competency for anyone in a leadership role. Effective speaking hinges on three pillars: meticulous preparation, controlled delivery, and a relentless focus on a clear, memorable message. Key strategies include knowing the...

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Did minimum wage policies kill entry level jobs? show art Did minimum wage policies kill entry level jobs?

CEO Bros - After Hours

5 Surprising Ways Raising the Minimum Wage Can Backfire, According to Two CEOs The Well-Intentioned Policy with Hidden Costs Raising the minimum wage is often seen as a direct and compassionate solution to help low-income workers. The logic seems simple: pay people more, and their quality of life will improve. However, for business leaders on the front lines of managing payrolls and profit margins, the reality is far more complex. They argue that this well-intentioned policy is fraught with hidden costs and unintended consequences. One CEO bluntly describes the policy as a "big heart, small...

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New Client Experience - Make or Break show art New Client Experience - Make or Break

CEO Bros - After Hours

Many businesses focus on a single question: How do we get new clients? However, a more critical question is how you keep them once you have them. This episode opens with a comical but eye-opening story about a truly terrible first-time experience at a dentist’s office. Despite spending a lot on advertising to attract new patients, this practice had a disorganized, impersonal process that left the patient confused, disrespected, and unsure about what procedures were even being performed. This is a powerful lesson for any business: a first impression, especially for a new client, is not just a...

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What got us here, won’t get us where we are going next.

 

The guys discuss the business philosophy that "What got us here won't necessarily get us there." The conversation focuses on the evolution of a growing business, emphasizing the need for change in leadership, systems, processes, and people to reach the next level of success. Both CEOs share personal examples. Ultimately, they conclude that bold, sometimes unpopular decisions are necessary for a company to scale effectively.



This discussion centers on a fundamental challenge faced by every growing business: the skills, strategies, and systems that fuel initial success are often insufficient to propel the company to its next stage of growth. The core maxim of the conversation is a powerful reminder that evolution is not optional.  "What got us here won't necessarily get you there." 

 

This concept applies to every facet of a business, forcing leaders to constantly re-evaluate their leadership style, their team's capabilities, the operational systems they rely on, and the very processes that define their workflow.

 

1. The Ultimate Test: Evolving Leadership

 

2. Building the Right Team for the Right Time

The principle that past performance doesn't guarantee future success applies to every member of the team. As a company evolves, the required skill sets for key roles change dramatically. 

 

3.. Upgrading the Engine: Adapting Systems and Processes

Beyond personnel, a company's growth is dependent on the evolution of its internal infrastructure. The software, systems, and core processes that work for a small startup will inevitably buckle under the weight of a larger, more complex organization.

Key areas of system and process change discussed include:

• Operational Systems: 

• Proactive Technological Adoption: 

• Mindset Shifts: 

 

4. The Leader's Playbook for Driving Change

Successfully navigating these transitions requires a specific set of actions from leadership. It involves recognizing the triggers for change, communicating the vision clearly, and making bold, sometimes unpopular, decisions.

 

Regardless of the trigger, clear communication is non-negotiable. A CEO must articulate when the company is at an "inflection point" (11:36). This helps employees understand the reasoning behind disruptive changes, reducing confusion and fostering buy-in for the new direction.

 

While making these decisions is one of the hardest parts of leadership, they are often the catalyst for the company's greatest breakthroughs.

 

5. The Positive Outcomes of Necessary Disruption

While these evolutions are challenging, they are a prerequisite for growth and often lead to unexpectedly positive results. The disruption caused by changing people, processes, or systems creates new opportunities for the entire organization.

 

The key positive outcomes of embracing necessary change include:

• Unlocking Hidden Talent: 

• Enabling a Major Leap: 

• Creating Space for Growth: 

 

The final takeaway for aspiring leaders is a clear and direct message: to elevate your company, you will inevitably face situations where the right decisions are not the most popular ones, but they are essential for reaching the next level.