In the Season 2 opener, Robert Sherrill and I sit down for an honest talk (and I mean real honest) about what it takes to be an entrepreneur. Robert will share his long journey to becoming a businessman, and we’ll both reveal some of the mistakes we made along the way, so you don’t have to.

Not everything is rainbows and sunshine in the world of entrepreneurship. Every business leader knows that there are bumps in the road, mistakes to be made, and uphill battles to climb. 

Robert Sherrill, the CEO and founder of Imperial Cleaning Systems and the author of many books on business including “My Journey to Now”, knows intimately what it means to work your way to the top. When he was released from federal prison in 2012, he gave it his all to make his own future.

“Everything that I have been through up until this point, especially my childhood, is definitely an advantage for me today,” said Sherrill.

Now, Sherrill shares the honest truth of what it took to become a boss. In this episode, host Elliott Noble-Holt and Sherrill tackle how to make the right decisions for your company, the importance of mentorship, and the real cost of getting started.

Starting the journey

Many times, people underestimate the work it takes to begin and run your own business. While many CEOs and business leaders are quick to tell you the awesome perks, not many are quick to share the ugly truth: it takes a lot of work.

“You need to make sure that you have great footing and understanding of what entrepreneurship is and what it comes with,” Sherrill said.  “Because there are a lot of sleepless nights and a lot of times where you can’t pay your own bills because you have to make sure your employees are straight.”

Even business leaders as successful as Sherrill have run into problems when first beginning a business. Mistakes are an inevitable part of the process while you learn the financial realities of running a business.

“I’ve been on contract and didn’t understand payroll taxes,” said Sherrill. “I was paying my employees $13 an hour but I didn’t know I had to send Uncle Sam a portion of that. At the end of the year, the IRS hit me hard. They shut my account down.”

That’s why Sherrill encourages business leaders to be ready and willing to share their knowledge with young entrepreneurs. Sherrill does consultations and works with aspiring entrepreneurs to help them overcome the most difficult parts of building a business.

Sherrill advises every successful entrepreneur to see their experience as important capital. Never underestimate the value of what you learned in your early days of entrepreneurship. 

“With mistakes as a CEO, you got to pay for them. The mistakes I’ve made with IRS, the mistakes I’ve made in the company buying the wrong equipment, not being able to get refunds, just everything I’ve paid for in this journey, it’s cost me a lot,” said Sherrill. “I’m trying to shorten the learning curve for other individuals.”

Staying grounded

Once you’ve made it to the top, it can be tempting to think of only yourself. But, Sherrill says the best bosses consider their employees in every decision they make.

“As a leader, you have to put yourself in other people’s shoes all the time,” said Sherrill. “Your employees have to buy into your vision as well. You can’t ask people to come in every day and bust their behind for you, if they don’t feel invested.”

Part of investing in your employees is returning to that key cornerstone of a successful business: honesty. 

If you’re focused on presenting yourself as perfect, you’re not doing it right. You should be willing to be transparent about both the ups and downs of what’s happening within your business. 

“Be authentic. Sell your strengths and buy your weaknesses,” said Sherrill. “If you’re going to put yourself out there as a figurehead in this entrepreneurship journey, then you at least need to be honest.”

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