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    Home»Business & Economy»US Business & Economy»After 10+ Years as a CEO, These 5 Issues Still Challenge Me
    US Business & Economy

    After 10+ Years as a CEO, These 5 Issues Still Challenge Me

    News DeskBy News DeskMarch 5, 2026No Comments8 Mins Read
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    After 10+ Years as a CEO, These 5 Issues Still Challenge Me
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    Opinions expressed by Entrepreneur contributors are their own.

    Key Takeaways

    • Some of my best business thinking doesn’t happen in the office. It happens on long walks with my dog, Baxter.
    • As an entrepreneur and CEO, those walks become a running mental audit of the decisions that matter most, including where my industry is heading, how to grow profitably, when to trust AI and how to build a team that lasts.

    I don’t know about you, but when I’m performing tasks at home or around the office, there are hundreds of thoughts running through my mind. However, the time I think about the most critical items facing my company seems to be when I’m walking my dog, Baxter.

    Baxter is a cool dog. Not only is he a fantastic companion, but he’s also my sounding board for business ideas and for venting about my day. Unlike my employees or most challenging customers, Baxter doesn’t cause problems or talk back. He simply listens intently and patiently as I verbally ponder life as an entrepreneur and CEO.

    While Baxter offers patience and admiration, he unfortunately can’t offer suggestions or advice on the myriad issues that we discuss. Given that most readers of this article are entrepreneurs or C-suite executives, I would be interested in knowing which subjects are constantly on your mind. Below are the 5 CEO issues I think about when walking my dog:

    What will my industry look like in 5 years?

    Do you remember the rise and fall of Blockbuster Video? Founded in 1985 by an oil and gas software engineer, Blockbuster grew to over 9,000 locations by the early 2000s. I vividly recall driving to my local Blockbuster store to find a just-released blockbuster video that I had been patiently waiting to secure.

    Interestingly, a significant percentage of the chain’s revenue stream came from late fees, which, admittedly, I contributed to. However, Blockbuster’s C-suite failed to recognize new strategies and technologies that would dramatically change their business model.

    Redbox was their first threat. Instead of making an additional trip to a Blockbuster location, individuals could quickly and conveniently select DVDs (albeit with a limited selection) at local pharmacies and grocery stores. Next came Netflix. Now, movie fans can pay a monthly subscription to watch movies and documentaries to their heart’s content without suffering the sticker shock of returning a DVD found between the sofa cushions.

    Why didn’t Blockbuster executives adapt to changing consumer desires and shift to online streaming or offer pop-up movie vending at strategic locations? I have no idea. However, Baxter and I often ponder what changes we may need to adapt to meet our clients’ needs.

    How to profitably grow my business

    Practically every entrepreneur struggles with how to grow their business. What I struggle with the most is how to profitably grow my company.

    With over a decade as an entrepreneur and CEO, I’ve dealt with tons of issues common to most upstart businesses. Thankfully, I successfully navigated the most significant challenges that most entrepreneurs face.

    My transcription company is profitable, and I have a competent and educated core staff that can handle most situations. Since my company still fits neatly within the “small business” category, I obviously handle the most crucial tasks such as marketing, interviewing and hiring higher-level employees, and resolving major customer service issues.

    The AI monster in the room

    In previous articles, I touched on the impact of AI across many industries. At first glance, you may think that AI has all but wiped out the transcription industry. It hasn’t, and for one simple reason: Most AI-generated speech recognition programs are only about 62% accurate. Since we offer a 99% accuracy guarantee, AI programs have a long way to go before they can come close to a trained and experienced human transcriptionist.

    Because my company employs dozens of employees, labor costs are always a primary concern. And since we only hire U.S.-based transcriptionists, my labor costs are obviously higher than those of my competitors who rely on foreign-based subcontractors who work for much less.

    In addition, we conduct extensive criminal and employment background screenings to ensure our transcriptionists can handle sensitive files. Legal audio files, such as depositions and court proceedings, obviously contain confidential information. Law enforcement suspect interviews are equally as sensitive. That’s why we are a CJIS-certified law enforcement provider.

    We have embraced and use AI tools on a daily basis. What skills and strategies should I develop, and which ones can my employees use to perform their jobs more efficiently?

    How to retain and recruit the right employees

    I’m fortunate to have a well-trained and qualified staff. Our turnover rate is low, and we have several seasoned employees who seem to enjoy their roles.

    Nonetheless, the job market is evolving. Recruiting and retaining qualified employees may be more challenging in the years ahead. All of our transcriptionists work from home, which is a benefit for anyone who values flexibility. We pay our employees competitive rates while offering steady work.

    Like many of you, I’m concerned about the work ethic of our younger generations.

    • Are they willing to invest the time and resources into learning viable skills?

    • Do they have the discipline to work independently and complete assignments in a timely and professional manner?

    • At what point will AI technology advance and make human transcriptionists obsolete?

    So far, I’ve been fortunate to find quality employees. Maintaining a reasonable labor cost percentage and keeping it from escalating too quickly presents several challenges.

    How to counter industry misinformation

    My guess is that most entrepreneurs struggle with misinformation within their industry. I’ve already touched on the inefficiencies and challenges AI has in accurately converting audio to a written transcript.

    AI transcription may work for your grocery or weekend to-do list, but it isn’t effective for complex projects. Overcoming that objection is challenging until a client learns their own lesson.

    Another issue arises when I hear potential clients suggest that all transcription services are the same. Do you believe that your company is the same as your competitors? I certainly hope not.

    My staff and I work hard to set ourselves apart from inferior competitors. However, it isn’t always easy. Our pricing structure is based on audio minutes, with general projects ranging from $1.50 to $5.00 per audio minute. Factors such as whether clients want verbatim transcription (every word and sound is captured), how many speakers are on the file, audio quality and response times are the main factors we consider in our pricing.

    Seeing competitors advertise their services at rates I know are incorrect is an ongoing challenge. Sometimes, allowing customers to experience poor service or deceptive pricing strategies works to our benefit. I simply wish I could convince them not to make costly mistakes on the front-end.

    How do I effectively educate our customer base?

    First, not all providers are the same. I have the utmost respect for fellow competitors who are trying to provide quality service at a competitive price.

    What bothers me the most are companies in our industry that I believe intentionally mislead customers into purchasing products or services that are inferior or will not meet their expectations. I spend several hours each week walking customers through what they believed they were buying from a competitor and why they were disappointed with the product they received.

    Our company’s rates are competitive. We are not the cheapest, nor do we advertise such. For example, medical transcription is what I consider “rate or price-sensitive.” Health care professionals, such as doctors and nurse practitioners, spend several hours each week recording audio notes of procedures and patient charts, which are then transcribed into permanent records.

    It’s one thing to make an error transcribing corporate sales numbers presented at a regional company meeting. It’s an entirely different situation when a foreign-based transcriptionist misinterprets a doctor’s orders for eight units of insulin to 80 units. That actually happened in 2012, resulting in a huge settlement for the surviving family.

    How can I convince a physician earning $500 per hour treating patients and spending eight to 10 hours weekly transcribing charts that he could spend less time transcribing charts and more time seeing patients? Baxter and I are still trying to tackle that challenge.

    What issues are you concerned about?

    Sign up for the Entrepreneur Daily newsletter to get the news and resources you need to know today to help you run your business better. Get it in your inbox.

    Key Takeaways

    • Some of my best business thinking doesn’t happen in the office. It happens on long walks with my dog, Baxter.
    • As an entrepreneur and CEO, those walks become a running mental audit of the decisions that matter most, including where my industry is heading, how to grow profitably, when to trust AI and how to build a team that lasts.

    I don’t know about you, but when I’m performing tasks at home or around the office, there are hundreds of thoughts running through my mind. However, the time I think about the most critical items facing my company seems to be when I’m walking my dog, Baxter.

    Baxter is a cool dog. Not only is he a fantastic companion, but he’s also my sounding board for business ideas and for venting about my day. Unlike my employees or most challenging customers, Baxter doesn’t cause problems or talk back. He simply listens intently and patiently as I verbally ponder life as an entrepreneur and CEO.

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