Think You’re Set Up For Success As A New Entrepreneur? Not Without A Mentor

Tony DiSilvestro

Running a business is hard, and the early days of getting it off the ground can be rough. 

I worked over 100 hours a week for years. I missed the first five years with my oldest daughter. I ran myself ragged, and it affected everything about my life. 

I also wanted to grow, and I soon learned that I couldn’t do it burning the candle at both ends. Something had to give. But I didn’t have a mentor. I didn’t have anyone coaching me or teaching me how to market, delegate, train, and scale my business. I had to figure all of that out on my own – at least until I made one of my wisest decisions.

Are you a business owner or an entrepreneur?

As a young man in the early days of my business, I thought I was an entrepreneur, but the fact was, I wasn’t an entrepreneur at all. I was just a business owner. And a stressed out and busy one at that.

The main thing I wish I’d had in my early days is a coach. I suffered so many losses in the first years of business that could have been cut by at least 50 percent if I’d had someone guiding me. It wasn’t until I was 10 years into business that a mentor came into my life. His name was Don and he worked for one of the first marketing companies I worked with. He would sit with me and go over business trends. 

When I first met Don I wasn’t growing. Eventually, I had to admit that. I had hit a ceiling, and to achieve my growth goals, I had to try something different. I was trying to do everything myself. The business was entirely dependent on me, and I’m only one person. So one day I took his advice and started looking at the big picture, thinking bigger. A huge part of this was learning to trust the systems I had in place and to begin delegating and trusting my employees to do the work without me. For years, Don had given me that advice over and over, but it wasn’t until I had a mindset shift that I followed it.

I’ve told him it was the best advice he’s ever given me. The most rewarding thing I do now is to be that mentor for others and to help them avoid making many of the mistakes that I did. 

So if you’re ready, I’ll say the same thing to you: If you want to grow and scale, you have to move from a business owner to an entrepreneur and know the mindset that shift requires.

Willingness to fail leads to success

“Failing well” sounds like an oxymoron, but it’s part of the path to business success. One must take risks to push their business forward, and failing is inevitable within that process. Learning to fail well is essential to becoming an entrepreneur.

For me, there are two types of failures: micro and macro. A micro failure is something that won’t cripple your business. It could look like trying a new product, depending on how much your products cost, of course. At my store, adding a new menu item that does not do well is a micro failure. But a macro failure will sink you. I almost experienced a macro failure when I opened a bakery when I was young. I wasn’t prepared, and I didn’t have a coach guiding me.

A good business coach helps you avoid macro failures and will often push you toward micro failures. Too often we associate failure with negative outcomes, but failure teaches us so much. And most important for entrepreneurs, failure builds confidence. Often, to make the jump from business owner to entrepreneur, you need to get your feet wet with failure. You need to experience some small bumps and learn that you’ll survive so that you can get back up and try again.

Business owners who haven’t yet jumped into entrepreneurship are usually risk-averse and overly cautious. Entrepreneurs want to scale and grow. They know their business cannot depend solely on them. Thank goodness Don entered my life and got me to understand that critical point. 

Everybody needs something a little different from a business coach. If you skew toward the business owner’s end of the spectrum, you likely need a coach to help grow your confidence and light a fire under you. If you’re more of a serial entrepreneur like me, you need someone to rein you in and help you make wise choices. Either way, one of the wisest decisions you can make is to have a mentor to help you on your journey. 

About Tony DiSilvestroTony DiSilvestro ( is the Forbes Books author of The Business Scaling Blueprint: Building a Foundation to Grow Your Brand. He has founded over 31 businesses and employs over 450 people. An award-winning entrepreneur, renowned international business and leadership trainer, and profitable real estate investor, he is also part of the Virginia Beach Vision Board, which involves the top 125 business owners in the area. DiSilvestro is the founder of Ynot Enterprises, and his background includes work experience in manufacturing, consulting, a SaaS training company, and residential and commercial construction. Distinction Magazine named him Entrepreneur of the Year. 




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