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

CEO Bros - After Hours

Release Date: 11/21/2025

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

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 WORKS*

• Purpose beats profit: Impact over the easy sports car

• Legal matters: 2018 code changes opened markets

• Show don't tell: Navy Pier proved doubters wrong

*WHO THIS PERSON IS* Rory Rubin founded S.I. Container Builds after careers in social work and consulting. She's turning an environmental crisis into affordable housing, licensed in all 50 states. S.I. Container Builds is a woman-owned, certified manufacturer creating sustainable steel structures built to code. They combat the housing crisis with economical ADUs and community developments. To learn more, visit https://www.sicontainerbuilds.com/

*WHO THESE GUYS ARE* Brian Balduf co-founded and sold VHT Studios. Brad Balduf runs By Your Side Autism Therapy with 550 employees across 11 centers. Matt Croke keeps it honest and pulls out the chaos. They've been there, survived it, and have the scars to prove it.

*THE UNCOMFORTABLE TRUTH* "My husband said are you sure you don't just want a sports car because that would be a lot easier. Now I look back, maybe that was easier." Ever take the hard path when everyone said there was an easier option? 

👇 SUBSCRIBE for new episodes every Friday. Real stories, real disasters, no LinkedIn energy. ———————————— *

TIMESTAMPS*

1:42 - The midlife crisis that started a company

4:44 - From social worker to manufacturing CEO

5:24 - 26 million containers and nowhere to go

7:19 - Legal since 2018 (people don't realize that's new)

30:22 - Navy Pier: First transient marina in Chicago history

32:04 - The bros want to build their studio in a container 

*ABOUT CEO BROS AFTER HOURS* CEO BROS: After Hours is raw business talk from CEO brothers Brian Balduf (VHT Studios) and Brad Balduf (By Your Side Autism Therapy) with host Matt Croke. Every Friday they share what actually happens building companies: brutal failures, scaling disasters, and the messy truth about leadership. No corporate polish. No LinkedIn energy. Just honest stories from the trenches. ————————————

🍸 *WIND DOWN WITH THE BROS: THIS WEEK'S COCKTAILS* Four drinks for four builders. Pick the one that matches your approach.

🍸 *THE STEEL STRUCTURE* Rory Rubin - Turned scrap into sustainable housing Recipe: • 2 oz silver tequila • 1 oz fresh grapefruit juice • 0.5 oz lime juice • 0.5 oz simple syrup • Pinch of salt • Grapefruit peel • Shake with ice, strain over fresh ice The Vibe: Clean, sharp, repurposed into something better. Rory takes what others throw away and builds something code-compliant. This drink's got structure underneath.

🍸 *THE SPORTS CAR* Brian Balduf - Sold VHT Studios Recipe: • 2 oz cognac • 0.75 oz lemon juice • 0.5 oz honey syrup • Champagne float • Lemon twist • Shake first three with ice, strain into flute, top champagne The Vibe: The easier choice. Looks impressive, costs more, everyone knows what it is. Brian picked entrepreneurial over corporate. Sometimes flashy isn't right.

🍸 *THE GRAVEYARD* Brad Balduf - The operator running 11 centers with 550+ employees Recipe: • 2 oz Irish whiskey • 0.75 oz coffee liqueur • 0.5 oz simple syrup • Orange peel • Stir with ice, strain into rocks glass The Vibe: 26 million containers sitting in shipyards going nowhere. Dark, underutilized, waiting for someone to see the potential. Brad knows what it's like to find value others overlook. 🍸

 *THE TRANSIENT MARINA* Matt Croke - The host keeping it real and pulling out the chaos Recipe: • 2 oz vodka • 1 oz blue curaçao • 0.75 oz lime juice • Splash soda • Lime wheel • Shake first three with ice, strain, top soda The Vibe: First of its kind in Chicago. Boaters from Wisconsin and Michigan finally have somewhere to dock. Bold, visible, makes a statement. Make all four.

Which one are you? Building from scrap? Taking the flashy route? Finding overlooked value? Creating something that never existed? Tag us. 

*JOIN THE CONVERSATION* https://x.com/CeoBrosAH https://www.instagram.com/ceobrosah/ https://www.facebook.com/CEOBrosAH https://www.linkedin.com/company/ceo-bros

 #entrepreneurship #manufacturing #startuplife #sustainability  Music: "Back to Black" by Rockin' For Decades (licensed through Epidemic Sound)