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ep 29 Avoiding the three biggest unforeseen pitfalls in starting a business

CEO Bros - After Hours

Release Date: 08/29/2025

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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More Episodes

Entrepreneurial Misconceptions: Money, Time, and External Forces

The guys emphasize the critical importance of financial preparedness in starting a new business, discussing the challenges of managing cash flow, especially with fluctuating pay periods and seasonal business models. 

They highlight the necessity of having personal savings to sustain oneself during the initial, revenue-scarce phases of a startup. Furthermore, they stress the importance of being "all in" and realistic, acknowledging that failure is often a part of the entrepreneurial journey and that plans inevitably encounter external disruptions requiring adaptation. 

The conversation concludes by advising new business owners to consider money, time, and external influences when developing their strategies.

The discussion highlights the often-overlooked challenges and misconceptions that can lead to business failure, emphasizing the importance of preparation, financial prudence, and adaptability.

 

I. The Reality of Cash Flow: Beyond Revenue

A significant misconception for new entrepreneurs is the sole focus on revenue without understanding the impact of cash flow.

 

  • Example: Three Pay Periods in a Month: 

  • Bridge Loans and Short-Term Solutions: 

"I've seen many successful businesses go out of business because you run out of cash... When you're out of cash, game's over. It's like running out of gas in your car."

 

II. Personal Financial Preparedness and Self-Compensation

A critical, yet frequently overlooked, aspect of entrepreneurship is the founder's personal financial situation and the timing of their own compensation.

  • The "Stash" and Moonlighting: 

  • Investor Expectations (Shark Tank Example): 

  • Family Discussions:

 

III. The Myth of "Get Rich Quick" and the Importance of Due Diligence

The podcast strongly refutes the prevalent social media narrative of overnight success, stressing the need for hard work and realistic expectations.

  • Social Media Deception: 

  • Hard Work and Due Diligence: 

  • Commitment and "All In": 

 

IV. Time as a Finite Resource and the Concept of "Runway"

Time is another critical resource that entrepreneurs often mismanage or underestimate.

  • Limited Timeframe: 

  • The "Runway" Concept: 

  • Commitment vs. Thinking: 

  • Components of Runway Calculation: 

 

 

V. External Influences and the Necessity of Pivoting

Entrepreneurs often focus solely on their product or service, neglecting the significant impact of external factors and the need for adaptability.

  • 50% External Factors: 

  • Unforeseen Challenges: 

  • "No Plan Survives Contact with the Enemy": 

  • Mental and Financial Preparation: 

  • Agility and Nimbleness: 

  • Employee Turnover: 

 

VI. The Inevitability and Value of Failure

Failure is presented not as a definitive end, but as a crucial learning experience on the entrepreneurial journey.

  • High Failure Rates: 

  • Failure as a Teacher: 

  • Calling It Early: 

  • The value of Objective Third Parties: 

  • Avoiding Blind Optimism: 

 

In conclusion, becoming a successful entrepreneur requires a deep understanding of financial realities, personal sacrifice, unwavering commitment, strategic planning for contingencies, and the flexibility to adapt to unforeseen challenges. The journey is rarely a straight line, and learning from setbacks is an integral part of growth.