Ashley Mason, Dash of Social & Student to CEO: Founder (Part 1)

At the age of 17 Ashley Mason began freelancing, working with companies on their social media presence. By 19 she officially started her social media management and consulting service called Dash of Social. Now at the age of 23 she runs both Dash of Social as well as Student to CEO which is a website meant to provide valuable information for aspiring entrepreneurs.

*Please note that most of Ashley Mason’s responses are paraphrased because the interview was conducted over the phone*

Can you tell me a little bit about your background and how you got to where you are today?

I always thought I wanted to be an accountant which is now far from what I would ever want to do. My company, Dash Of Social started because of the blog I created when I was 15. Because of this blog, I started working with companies in paid partnerships, and then I started realizing that not many of them were focusing on social media. I started to take an interest in social media so I helped them in their marketing campaigns. I started becoming really passionate about it, went into freelancing, and grew it from there. I definitely found that dipping my toes into different activities, and hobbies, and interests that I was intrigued with helped me realize that this is what I wanted to do for the rest of my life and I kind of took it from there. 

When I was starting a business at 19, I surrounded myself with a bunch of entrepreneurial communities, but the people in them were 2-3 times my age. It was really hard to relate to people on a personal level because I was young enough to be their daughter or granddaughter. I kind of realized that having the ability to talk to like-minded individuals around your own age is something that people truly need, and helping people from my own experience is something that I became really passionate about. There have been so many people from ages 17 to 23 who have reached out asking “what’s your advice”, “what would you suggest for getting started”, and stuff like that. People were constantly asking questions and also with the fact that I got asked to do a Ted Talk on this topic, I realized that people need something like this which is why I created Student to CEO.

How did you overcome the hurdle of people not taking you seriously while you were younger?

Fortunately, my parents have always been really supportive of me and have encouraged me to follow my dreams and do whatever I am passionate about. Since they believed that I could go ahead and be successful, that was all I needed for validation. If the two people closest to me and most important to me believed I could do it, then the opinions of others did not really matter. I think it would be a little more difficult if my parents had not been so supportive. 

One thing I did was view the nay-sayers as an organization. People kept telling me that I shouldn’t take my venture full time and that I should focus on getting an internship and a job; I decided to use these words as motivation to keep on pushing to my goal. It is almost like I thrived off of the negativity. 

Also, just being able to connect with people in the same space is another way I got through it. I truly believe that you thrive off the community you are in. I surrounded myself with other entrepreneurs who “got it” - so being able to surround yourself with people who will support you and totally understand the process was really huge. I actually have a really good friend who was my client and turned into one of my best friends. She single-handedly became a really important mentor for me these past few years of just being able to answer questions and give me advice. One thing I would recommend is find a mentor in the same type of space you are in who can provide you with advice and support.

Why do you think it is so important to start a business at a young age?

You don’t have a mortgage, you don’t have kids or any type of big responsibility that would be holding you back from making that type of decision in your life. If you fail, you can just go to the corporate world if that is really what you want. Of course I had some people say, “why are you starting a business so young” and then I had other people say, “now if things don’t work out, it’s almost like you can move on as if nothing ever happened.” People were always like, “why would you start a business, you have student loans and stuff to pay for.” Well, I paid off my loans in October, 6 months after I graduated. I never would have been able to pay off my loans that fast if I was in a 9-5. With entrepreneurship you have to look at everything with perspective - you know yourself and your dreams better than anyone else does, so not taking their opinions and not allowing others opinions negatively affect how you feel is definitely important to work on.

 I am really passionate about mindset in business. You need to be in the right mindset to be successful and grow your business and keep moving forward. When I was starting, that was one thing I didn’t realize. I thought business was all about strategy, but mindset plays a huge role in that. I never realized how important mindset was until a year or two into my business. Now I know that having the right mindset as a business owner can greatly change things for the better.

Can you talk about how you have failed and how this has helped you later in life? What have you learned?

Not listening to my gut. I wished I followed my gut instinct on somethings and didn't move forward. But I didn't listen and I moved forward anyway, causing a disaster. An example of that with my marketing firm would be speaking to someone on the phone, not really thinking that they're a great fit, but then going ahead and working with them anyway. I found out, almost every time, that the client was a headache, I was stressed out, and that they weren't worth the money. Over time I realized that it's not always about the money, It's more about your sanity and being able to not be stressed out all of the time. So if you speak to someone and you're like, “oh I don't want to work with them ever”, you need to look into your gut and realize that you need to not go forward. There have been so many times I've been put into bad situations because of the fact that I had that gut feeling yet ignored it. 

Another thing that has happened to me only once or twice but has happened to others multiple times is when they look to start to collaborate with people, but they don't actually vet the people and the people end up wanting to use them to leverage their audience, their network, and their resources - and all where it was not really a beneficial deal. Anytime I've collaborated with someone on something, I always make sure that this is something that I actually want. You need to make sure the person that you are doing it with is actually going to go 50/50 on the work with you, you need to make sure that you both have the same interest at heart, and you need to make sure you are both going to put in the same amount of time and effort.

Another mistake I've made is not understanding my worth.  There were times when I was constantly undercharging for services that should have been worth a lot more just because I felt like I wasn't worth that much. I ended up not making as much money as I could have as a result and I also ended up attracting not the right clients for me. If you feel that you're worth a certain rate, then you are - come up with a rate and make sure you stick by it. Don't undersell yourself just because you think someone might not want to pay that much or because you just want to get the money. 

Check back on Friday to see the second part of this interview!

Useful Links

Dash of Social's Website

Student to CEO's Website

Ashley Mason's LinkedIn

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