5 Hard Truths to Becoming a Business Owner

The Realities of Becoming a Business Owner: Lessons from ‘the Trenches’

Harry Catrakilis shares hard-earned lessons on becoming a business owner from his years managing CKH, offering insights on what it truly takes to run a company. From handling stress to finding fulfillment in developing others, his experiences shed light on the realities of business ownership—beyond the surface level success to which many aspire.

“Some of my former staff who read these blogs ask, “Are you always complaining? Can’t you write something with a positive spin?” It’s true, I have high standards for myself and my industry, so I can be critical at times. That said, I’m up for the challenge. So, here’s my take on what I’ve learned as a business owner, hopefully from a more optimistic perspective.

When I was younger, maybe around 21, my family threw me a birthday party. My dad and his siblings were all business owners, while I worked for a big corporate firm. I remember telling my uncle Steve, my dad’s brother, “You guys are so lucky to own your own businesses. I have so much stress working for a large company!” It was the only time I remember Steve raising his voice at me, essentially telling me I didn’t know what I was talking about; a ‘young buck’ talking with ignorance. Now that I’ve been in business myself, I understand why.

Here are five truths to business ownership I’ve learned over the years.

1. Business ownership means everything is on the line.

When you’re running a business, especially if you’re trying to build wealth, every major decision could make or break you. While corporate employees may lose a job and quickly find another, for a business owner, the stakes are higher. I’ve spent many sleepless nights wondering, “If this goes wrong, we’re done.” The upside? That pressure can fuel incredible focus and drive. If channeled properly, it pushes you to do remarkable things.

2. Sweating payroll never goes away.

I once had a client who sold his highly successful business to a public company. During our celebration, I asked, “Rick, how does it feel?” His reply was unexpected: “Harry, for the first time in my life, I don’t have to sweat payroll.” That struck with me because I assumed someone at his level wouldn’t worry about payroll. But as I’ve grown my company, I’ve learned that no matter how successful you get, counting cash flow before every payroll run remains part of life- that certain stressors don’t just go away with success. Sure, you can borrow or set up credit lines, but regularly sweating payroll is a hallmark of serious businesspeople versus those who aren’t making it.

3. You can outwork failure.

In the U.S., if you work hard enough and have some talent, you can get ahead. But make no mistake—success is not about having a lax schedule or escaping a boss. I’ve heard people say, “I want to start my own business so I can work whenever I want.” They don’t realize that as a business owner, you never really stop working. Yes, I can choose to watch my daughter play soccer, but then I’ll be up working until 2 a.m. afterward. Even on vacations, my family often enjoys their time while I turn our kitchen into what my nephew once called “The Situation Room.”

If you want the lifestyle, you must be willing to make those sacrifices: hard work is the vital ingredient to setting your business apart from others.

4. Courage is essential—but it’s not reckless.

Courage is key to business, but it’s different from recklessness; courage does not make up for being unprepared or thoughtless. My dad’s family had five siblings, all immigrant small business owners who would tell me when I was younger that I must go into business.

So, when I decided to start my own business at 28, I went to my boss at the time, a CEO named Alan. I told him I was resigning to launch my own venture. He asked, “Do you know what it takes to start a business?” I rattled off what I thought were the right answers—money, a good business plan, and connections. Alan looked at me and said, “Harry, you need BALLS. Do you have balls? If so, go for it. If not, stay working for someone else.” That conversation stuck with me. Courage means taking risks, but not without preparation.

5. The best feeling is helping others succeed.

One of the most rewarding parts of business is seeing someone you’ve mentored grow and succeed. Taking someone whom others may have overlooked, a ‘rough diamond’, and helping them achieve a part of the American dream is one of the coolest experiences in life. It doesn’t happen often, but when it does, it’s a feeling like no other.

Conclusion:

Business ownership comes with immense challenges and countless sleepless nights, but it also offers rewards that are hard to find elsewhere. From navigating payroll stress to the satisfaction of mentoring others, these lessons have shaped my perspective on what it really takes to succeed in business. It’s not always glamorous, but the hard work and perseverance are worth it for those who have the courage to keep pushing forward.” -Harry Catrakilis

The above article only intends to provide general information and reflection. It is not designed to provide specific advice or recommendations for any individual. It does not give personalized tax, financial, or other business and professional advice. Before taking any form of action, you should consult a financial professional who understands your particular situation. CKH Group will not be held liable for any harm/errors/claims arising from the blog. Whilst every effort has been taken to ensure the accuracy of the contents, we will not be held accountable for any changes that are beyond our control.