Entrepreneur to Employer - The Playbook for Scaling from Solopreneur to Employer

Entrepreneur to Employer - The Playbook for Scaling from Solopreneur to Employer

Building a successful business means managing a constantly shifting target, especially when assembling a high-performance team that drives revenue, enhances the bottom line, and meets expectations. The Entrepreneur to Employer podcast is here to help. Tailored for entrepreneurs, this show delivers practical insights across three critical areas: time, money, and people operations. From developing sales systems to creating an operations manual or even preparing your business for sale, Entrepreneur to Employer has you covered with actionable strategies. Expect monologue episodes with direct insights, interviews with industry experts, and founder stories to inspire your journey as an entrepreneur. If you enjoy the podcast, please subscribe to get notified of new episodes. If you find it especially helpful, leave a 5-star review and a comment—we appreciate the feedback! Questions? Please email me at brianm@scaleocityworks.com

Episodes

May 27, 2025 8 mins

Are your business foundations helping you scale, or silently holding you back?

In this episode, we break down the six critical areas every first-time founder needs to stabilize to grow: people clarity, operations, hiring, systems, culture, and finance. Whether you're building your first team or stuck in reactive mode, this is the episode to help you step into leadership with clarity.

Join Brian Montes, your Fractional People &am...

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In this episode, we’re tackling a mission-critical topic that too many mid-market companies overlook—Business Continuity Planning (BCP). Whether you’re leading a $50M company or approaching $500M in annual revenue, disruptions can strike without warning—from cyberattacks and natural disasters to supply chain failures and major IT outages.

Join us as we break down:

  • What a Business Continuity Plan is (and what it isn’t)
  • Why mid-mark...
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In this episode of the Entrepreneur to Employer podcast, host Montes tackles a topic many business owners avoid until it’s too late: workplace dating policies. Whether you're running a small business or scaling a growing team, creating clear policies around romantic relationships at work is essential to protecting your culture, reducing risk, and promoting professional conduct.

You’ll learn why you must establish a workplace da...

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What if your business could grow without you being involved in every little decision? In this episode of the Entrepreneur to Employer podcast, we're diving into the game-changing mindset and strategy shift every founder must make to build a profitable company that doesn’t depend on them 24/7.

From shifting from operator to CEO, to hiring for outcomes (not just tasks), and building invisible systems that drive performance, this ...

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In this episode, Brian Montes interviews Todd Zive, a business consultant and author of 'The Mensch Method.' Todd shares his journey from the medical technology industry to becoming a strategic advisor and author. 

He discusses the inspiration behind his book, the importance of resilience in leadership, and the core principles that guide his approach to business and personal development. The conversation also delves into t...

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Workplace investigations are high-stakes for business owners, CEOs, and HR leaders. If they are mishandled, you risk legal action, employee distrust, and damage to company culture. In this episode of the Entrepreneur to Employer podcast, we discuss how to structure and conduct a fair, unbiased workplace investigation, ensuring compliance, protecting your business, and maintaining trust within your team.

You'll learn:
✅ Why ...

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Scaling your business sounds exciting, but if you don’t have the proper foundation, growth can break your business instead of building it. In this episode, Montes walks you through five foundational principles every business owner must establish before attempting to scale.

If you want to grow your business sustainably—without chaos, burnout, or financial instability—this episode is a must-listen!

Key Takeaways:

✅ Why profitability mat...

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Are you constantly saying, “I don’t have enough time to get everything done”? Are your employees maxed out, leaving you thinking about hiring someone new? Before deciding, listen to this episode and discover the 5-Hour Challenge.

In this episode, we’ll break down a game-changing process designed to help business owners and their teams free up time, eliminate unnecessary tasks, and refocus on what truly matters.

You’ll learn:

  • What ...
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Welcome to another insightful episode of the Entrepreneur to Employer podcast! In today’s episode, we explore how building effective business systems can empower your team, streamline operations, and set the stage for scalable growth. Whether you’re already running a thriving business or preparing to take your operations to the next level, this episode is packed with actionable insights to help you confidently scale.

What You’ll Lea...

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In this episode of the Entrepreneur to Employer podcast, we explore one of the most overlooked but essential steps in the hiring process: crafting a great job description. A well-crafted job description is more than just a list of duties—it sets the stage for attracting the right talent, aligning expectations, and ensuring hiring success.

We’ll walk you through a comprehensive checklist to help you create job descriptions that stand...

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Is your business hitting a growth plateau, and you’re unsure why? The answer might be YOU. In this episode of the Entrepreneur to Employer podcast, host Montes dives into the common challenge many business owners face: becoming the bottleneck in their operations.

If you’ve built your business from the ground up, it’s easy to fall into the trap of needing to oversee everything. But to scale your business and reclaim your time, you mu...

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In this episode of the Entrepreneur to Employer podcast, we dive into the five non-negotiable building blocks every small business owner and first-time CEO needs to create a scalable and effective People Operations system. Whether you’re just starting or looking to fine-tune your processes, these foundational elements will set your business up for long-term success.

What You’ll Learn in This Episode:

  • Why a strong People Operation...
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In this episode of the Entrepreneur to Employer podcast, Brian Montes discusses the importance of reflecting on the past year as a business owner. He shares ten key questions entrepreneurs should ask themselves to ensure they progress, learn, and make impactful decisions for the upcoming year. 

The conversation emphasizes the significance of mindset, risk-taking, value creation, and building meaningful relationships in ach...

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In this episode of the Entrepreneur to Employer podcast, Brian Montes guides you through one of the most challenging decisions business owners face: letting go of an underperforming employee. If you've been struggling with whether to fire someone now or wait, this episode provides a clear, step-by-step framework to make the process less daunting and more strategic.

You’ll learn:

  • How do you decide whether to fire now or wait?
  • ...
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Efficient business operations are the cornerstone of growth and profitability, yet many business owners resist implementing systems. Why? In this episode of the Entrepreneur to Employer podcast, we explore the four biggest reasons entrepreneurs avoid creating operational systems and how overcoming these challenges can transform your business.

If you’ve ever felt overwhelmed by the thought of delegation, worried about losing control,...

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Brian Montes discusses the challenges of managing underperforming employees in this episode of the Entrepreneur to Employer podcast. He shares personal experiences and emphasizes the importance of addressing performance issues to maintain workplace morale and culture.

Brian introduces a three-part test to help business owners evaluate underperforming employees and make informed decisions about their future with the compan...

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In the Entrepreneur to Employer Podcast episode, Brian Montes dives into employee retention by uncovering the seven signs your top performers are about to quit. Losing your best employees can devastate your business, especially when you’re a first-time founder or small business owner trying to scale. 

But how can you spot the early warning signs before it’s too late?

Tune in as Brian explores the telltale signs that your to...

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In today’s episode of the *Entrepreneur to Employer* podcast, we’re diving into one of the most crucial steps in building a successful business: creating a hiring process that brings in your ideal employees. We’ll guide you through designing a hiring strategy that fills open roles and attracts candidates who align with your company culture, values, and goals. 

From writing job descriptions that attract high-quality applica...

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Brian Montes discusses the importance of overcoming fear-based decisions as a business owner in this episode. He explains that fear can hinder business growth and lead to reactionary and cautious decision-making. Common triggers of fear in business include financial instability, intense competition, and sudden market changes. Brian provides ten steps to help business owners embrace fear and make it an asset, including understanding...

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In this episode, Brian Montes discusses the importance of creating a sales system for business growth. He emphasizes that hiring salespeople is not always the best solution and instead recommends focusing on developing a strategic sales system. He outlines seven steps to create a scalable sales system, including identifying the target customer, defining the value proposition, developing lead generation strategies, mapping out the s...

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