Cindy Ashton

Cindy Ashton is an energetic Canadian, that's making a name for herself in NY, NY with her Toronto charm. Cindy owes her success to her gift of gab and her fearlessness. For Cindy fearlessness wasn't really a choice, it was a necessity. Growing up Cindy wasn't only the pink sheep of her family but also a person living with chronic heart failure. She was born with a 20% chance of living and had three heart surgeries by the time she was 14. The left side of her body was structurally damaged and she needed casts on her legs in order for them to grow out properly. Under those circumstances, one can't afford fear. I knew that within the first five minutes this was going to be a great conversation and looking back, she’s definitely one of my favorite entrepreneurs thus far. I'm going to tell you about a little girl that almost didn't make it at birth. Who grew up into a woman who's training corporate executives to do what she does better than anything else: stand in front of a room full of listeners and be her “best self”.

Originally from Toronto, Cindy always knew that it wasn't the city that would allow her to reach her full potential. Though it has and always will have a special place in her heart. She knew that the group she belonged to, the ambitious creatives, were somewhere else. Being from Northern Virginia myself, I can relate to that feeling. She describes Toronto as smart, hard working and conservative. She describes herself, as the pink sheep of the family. Neither of her parents were entrepreneurs. Her father ran a limo service and her mother was an accountant. They emigrated from the Middle East and were firm believers of getting a job. Taking the less risky route; as many parents are.  

In college, or University as they call it in Canada, she double majored in music and Kinesiology.  Half the school day she sang opera and the second half she dissected bodies. Her Kinesiology degree comes in very handy for her to this day, mainly for her own health. Cindy made a great point during our conversation when discussing her health. Being an entrepreneur allows her to maintain her health. If she had a job, she feels that her career could have been negatively impacted by her health problems. Being her own boss, she controls her schedule and workload. She encourages anyone who suffers from health problems to pursue entrepreneurship. As an entrepreneur, if she isn’t feeling good she just doesn’t work and doesn’t have to ask for permission from anyone. This became most important to Cindy some years ago. After three years of working hard, traveling and conducting between 5-10 speaking engagements a month. She had over worked herself so much that she had to return to Toronto and not work for one year. She was so drained that all she did was rest. Which again didn’t require her to ask for permission from anyone. This experience required her to think differently and change her business model. Instead of doing many engagements a month for a decent amount of money she decided to limit it to 4 events a month and take nothing less than $5,000. Know your worth. Today Cindy works part time hours and makes a six-figure income. If she had not gotten sick she wouldn’t have been forced to think differently and create a business that works best with her health. For that, she is grateful.  For that, she is awesome.

“Go where the energy goes.”

How did Cindy get her start in public speaking? It was quite organic. After college she got started in professional singing and educational consulting: teaching teachers how to teach. She started getting requests from various folks who wanted to invite Cindy to speak about education. Things really took off when she released her first album as a musician. People were very interested in the story behind the music. This interest lead to media interviews, which lead to requests to speak about overcoming obstacles. Sometimes you don’t choose your business, but it chooses you. In Cindy’s case, public speaking chose her. It pays to pay attention and not miss your window of opportunity.

“We have openings of opportunity all of the time and we don’t walk through those doors because we don’t see them. We’re too busy standing in the struggle. If something feels easy and it’s open and it feels good, it’s probably the better direction than staying in the struggle and trying to fight and put your head against a wall, when something is not working. It’s more important to go for the opportunities that show up for you and be open to that maybe something will show up in a way that you never thought about before.”
 "It’s a tricky balance of going where you are being lead to go but also knowing that you’ve got to take the risk and take the action that it’s going to take to get you there.”

When was a time when you were the most uncomfortable but you knew that this was the best route for you to take?

“Let’s talk about when I moved to California. It was 2008, I knew I had to be in California. I had two really big contracts signed, for when I came and I started immigration. When you do immigration you need to show that you have work. So I sold my beautiful condo that I had on Queens Quay, Toronto. Right on the lake. On September 30th, I closed on my condo. I was sleeping on my mom’s couch waiting on immigration to come through and on October 2nd of 2008, was the big economic crash. Within a month after that I lost my two big contracts and my work visa came through. I had no house, I sold all my furniture, my piano of 25 years. I cried my eyes out on that one because that’s part of my body, my piano. But I knew I had to stick it through, I mean I had given it all up. So I literally moved to California knowing only one person, with no contracts and at one of the worst economic times, ever. Talk about having to be uncomfortable, right!”

I believe that that’s the epitome of discomfort. When Cindy arrived to Orange County, California she was very upset and worried that she had made a mistake. On the sixth day of being in California she decided to take the bull by the horns. She attended a networking event, shook some hands and found some clients that had her booked as a speaker in no time. She described it as, “Do or die.”

“It was an amazing time, I still don’t know how I ever did it and I don’t want to do it ever again. It was major hustle man, you gotta do what you gotta do!" 
"I’m not here to be entertaining for a day or two, I’m here to make a damn difference in someone’s life for a long time. I want to leave a legacy, I don’t want to just inspire people for one day.”

What is some advice that you would give to entrepreneurs in regards to branding?

“People will pay more for an experience than a product. When you think of Nike, are you buying strong shoelaces or victory? You’re buying victory. Ask yourself ‘what experience are you bringing to people?’ and ‘how can I shape my business and everything that I do in my business to give that experience?'” 

When it comes to branding your business, everything should be considered. Branding is really important. It’s almost the most over looked thing by most business owners and leads to so many missed opportunities. Due to that customers can’t get a feel for who your company is outside of the service or product line. Everything from the color scheme of your website, to the color of the clothing you and your employees wear should be considered. The words that you use, your etiquette. Pay attention to it all because your potential customers definitely are. “Are they buying shoe laces or are they buying victory?”

What is one piece of advice that you would give, if nothing else, to aspiring business owners?

“Be open, be humble, be open to learn. While trusting yourself.”

I thoroughly enjoyed speaking with Cindy and learning more about her story. If you would like to learn more about Cindy or her trainings, she has some great videos on her site. You can learn more here.

Chadwick Daniel