July 15, 2021

Ryann Halo: How A High School Dropout Became A Successful Entrepreneur

By: Gary Schoeniger



Ryann Halo joins us to talk about her entrepreneurial journey. Hear her dig into surviving tragedy and trauma, overcoming it all to become a successful business owner of two award-winning salons.

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  • Read the transcript below.

    Ryann Halo: How A High School Dropout Became A Successful Entrepreneur

    I’m speaking with Ryann DiBenedetto. What an incredible story. At age eleven, an unimaginable tragedy struck Ryann’s family. By the age of fourteen, she was a near-homeless dropout living with friends. She had a chance encounter with a mentor who opens a new door that alters the course of her life. Now, Ryann is the Founder and CEO of Salon Halo, a thriving hair salon that specializes and helping others be their best. Her story was full of inspiration and insights into the mindset that empowered her to overcome the obstacles that ultimately enabled her to succeed. Without any further ado, I hope you enjoy my conversation with Ryann DiBenedetto.

    Ryann, welcome to the show.

    Thank you for having me, Gary.

    I am super excited to dig in to learn more about your story. We met and we’ve got a little bit of your story enough to be intrigued. I want to try to jump in. Let’s start from the beginning. I want to ask you what set you on an entrepreneurial path. Before we get into what you are doing entrepreneurially, what I’m trying to figure out is, were there people in your lives that were entrepreneurs? Were you inspired by somebody? Did you jump in the pool? Did you fall in a pool? Did you wait in the pool?

    Take it back quite a bit. Growing up, I never specifically saw myself owning a business. That is not the picture that I had for my future. I was born in 1990. At least in my experience around that time, I went to college and was put on a pedestal. I was interested in honors classes from a young age and it was drilled into me that to reach my full potential or to have a stereotypical picture of success, college was the only route. That was the plan. I enjoyed school. I didn’t love it. I like to have a good balance of socialization, Art, Math, Science, all of it. I had a normal childhood for the first half of that. Mom, dad, little brother, lots of aunts and uncles, cousins, it’s stable. My mom was a nurse. All professionals in my family.

    My grandpa did own a machine shop but he was the sole employee. He’s a hard-working German immigrant but I never saw a lot of the running the business aspect of that. I went along thinking that was my path. When I was eleven years old, a tragic thing happened to my family. My father committed suicide and took the life of my six-year-old brother. As you can imagine, that would alter the course of my future and also my family’s.

    From there, things don’t feel like what they look like in the movie. I personally didn’t have that moment of breaking down and freaking out. It was all surreal. My mom was obviously the most impacted immediately. She continued to work and she was successful. She had two houses at that time and she was moving up in the nursing world. At that same time, she started dating a new person. There were a few catalysts to what happened but all of a sudden, I found myself living with someone who’s a stranger to me. My mom was in a new relationship and her head was in a few different places. I had to start taking care of myself to an extent. She was a great mom but anybody put under such traumatic events is going to affect them.

    At that point, things were okay but they did slowly start to deteriorate. My mom was going through a lot emotionally and did have some substance abuse problems going forward. When I hit about 13 or 14 years old, she was no longer working. I did not get along at all with her now-husband at that point but it became toxic and with such an unstable home life. She got to the point where she would be up for three days asleep for three days. I started becoming behind in my classes and my credits. It was completely unstable. It was so much to the point where I was worried about my safety.

    Thankfully, my mom has gotten help and is in a much better place now. I want to be honest about what I experienced at that point because it was so overwhelming and not at all what I had become accustomed to in terms of stability and it started to feel like a nightmare. We are not seeing any support from other adults and no one wanted to acknowledge what was going on because she had been through so much. I felt unsupported, alone at that point and I developed a thick skin. I would consider myself independent to the point where if I want to make something happen, I’m going to figure out a way to make it happen. If I want money for the things I want, I’m going to figure out a way to make the money. I’m going to sell candy.

    Where did that come from? Did that come from the hardship? Where did you get that attitude? You used selling candy as an example. Was that a survival mechanism?

    I’m an opportunist. If something is going on, I’m going to make the best of it. I remember the first memory I have of selling anything would be fourth grade and selling candy bars for fundraisers. I had fun with it because I would offer people something and they would take it. They enjoy the interaction and they seem to become happy. I was like, “There’s something to this.” It was a fun exchange so that showed me a lot of opportunities.

    I have to tell you, I hear that a lot as a childhood experience. There’s some experience of selling something door-to-door. I watched my mom selling flowers on the weekends or something. There was some connection with some sales experience where you can communicate and create value for other people.

    It was fulfilling. I am a people person and I like variety and it was fun. I felt that I could apply myself and see a result. That was the first memory I have of sales or any type of entrepreneurship. That grew through the years I sold knock-off purses and jerseys. I would buy candy from Sam’s Club and then sell that. I always was thinking ahead in that way but I’m not wasn’t even at a time that I had hardship. I was motivated to do that. When we come back to that timeframe, when I was about fourteen years old, things became unstable. I was concerned about my safety. When my grades were to a point where I did not feel I could recover in school, it was the most hopeless feeling I have ever felt.

    At that point, I had to leave my mom’s home. I was at a point where there was a chance I would be put into some type of program or it got dark. I took off. Especially being that I didn’t have any family members that were willing to go against her in that fragile state at that time so I was on my own. I didn’t know what my next step was going to be. I felt extremely hopeless in a way that college and what the grades you get in high school, and then going to college had always been the only path to success that I had been shown or that I believed.

    The home that I was able to now find a place to stay in was with a friend whose parents didn’t care about what anybody did. There were a lot of influences around like drugs and alcohol. I was still resisting going down that path. I was still a good kid for the most part. I didn’t have a home in the figurative sense. I didn’t have stability and consistency. I’ve got to this crossroads where I became more and more depressed. I was spending time with people that were not a good influence. There are a lot of darkness. I had to make a choice. Do I want to fall into this crowd, do these jobs, live this lifestyle and truly give up? What’s holding me back from doing that? As I thought my life was over. My oldest promise and I had been told I had since I was young seemed like there was no path to realize.

    You are seeing your dream of going to college dwindle because your grades are suffering and you feel like, “That can’t happen now. I’m too far behind. I’m lost and there’s no other path to take.” Do you remember having that conversation with yourself? “Am I going to give myself to this drug-alcohol way of life or am I going to remember that?”

    I do to an extent. I remember the overall mindset I was in. I was still holding myself above the drugs and the things I was around and chuckling at some of the behavior I saw but I remember when it got a little too dark and when I even began to entertain the idea, that’s when I knew it was serious. Something needed to change or something was going to change one way or the other.

    I get what you are saying. When you don’t have an alternative path, what do you do? What did you do?

    There was a little bit of divine intervention that I was given a path and an option showed up in front of me. There was a woman who was related to one of the people in this circle and she was his aunt. She came over one day to the house we are all at. She got to know me a little bit and asked some questions about who I was. She was a hairstylist. She was young, hip and came from New York City. She specialized in hair coloring and I had worked when I was young in my aunt’s hair salon. When I say work, I use that term loosely. I do some shampooing, hang around and sleep. That was more of a family operated a little bit more of a relaxed environment. It was in the back of my brain that I had to have that experience.

    She said, “You have done some shampoo work. Do you want to come to assist me for $25 a day?” It would have been easy to do that and say, “$25 a day? Who do you think I am,” or whatever you might take away from that. I jumped on the opportunity. I was so excited to have an outlet for my enthusiasm and a way to apply myself. Thankfully, she was a great mentor personally and professionally. She gave me somebody to look up to or have some guidance. From there, I started to understand that industry differently. The fact that not only on a technical level but the Science, the Chemistry and the Art that all goes into the field of doing hair.

    Also, on a professional level, how you can be of service to people and how fulfilling that. The more you apply yourself, the more you get back so it’s not going and working a 9:00 to 5:00 where you make an hourly rate and you have set it up whatever you do. What I was putting in, I was getting back. It was so fulfilling and rewarding. At that point, I was working at the salon for her the day she worked there and whenever she didn’t need me, I was either reading the back of the bottles or the pamphlets that have been there in the bathroom for years that nobody has looked at in forever. I was cleaning out underneath the stage, sweeping the whole salon and offering the shampoo for other stylists in the salon. I didn’t have much of a motive other than it was rewarding. When the owners saw me and how hard I worked, he offered me a job when my stylist wasn’t there for $50 a day. Right there, it reinforces the hard work. It’s paying off.

    I told you my gutter cleaning story. I love that aspect of it. In spite of all the bad stuff that happened, your hope circuit is still open. That’s what’s astonishing to me. You still have this belief deeply seated in you that, “Somehow, I’m going to find a way.” I love that story of $25 a day. That’s $3 an hour. I’ve got to tell you a side story here. I used to be afraid to do public speaking. This is what I do a lot now but I was afraid to do it. I live in Cleveland, Ohio and I went to a homeless shelter on Tuesday mornings for about six months and gave talks to homeless people because there’s a low threshold. There are 6 to 8 homeless guys there. I’m going to try to talk to them in some way that might be meaningful to them and try these ideas out.

    I met a guy there that got out of prison and he asked me to be his mentor. His name is Todd Daniels. He has since passed away. I said, “Go knock on 100 doors.” He was 38 years old and he just got out of prison. When a 38-year-old black man is applying for minimum wage jobs, that’s a tough spot to be in. Long story short, he got a job in a call center and he had the exact same attitude you did. He said, “They are only paying me for eight hours for one shift but I’m going to work two shifts because I’ve got nowhere else to go.”

    He showed up at 7:00 AM and he left at 11:00 PM. Two years later, they were sending him to South Africa and the Philippines to open training centers. It’s a similar story. I love that you are at this crossroads where you don’t want to go down the degenerate path and you are hanging around people like the lost kids. You realize that that’s not the way to go. That $25 a day thing turns out to be the opportunity. I love that. I don’t want to interrupt. Where does it go from there? The owner of the slot offers you $50 a day.

    He doubled my pay on the day that I wasn’t working for her. First of all, technically, I’m supposed to be in school at this age. It was all under the table. I eat with tips. I saw myself bringing home $100 a day in some days $1 or $2 shampoo.

    Were you 14 or 15?

    I was fifteen.

    You are seeing the connection between your effort, your attitude and outcomes. It’s an important part of the story.

    I started learning the finer points of how to do hair. There was still this little voice to me, though that certain idealized lines of work, whether it be a lawyer or CEO of some large company. Those were the pictures that I was holding on to in my head of what success meant. I was nervous about settling and being a “hairstylist” a cop-out job. I was torn between those two frames of mind but I kept that. That’s what I had so that’s what I was working with. I’ve got to a point where I had to make a choice. My mentor encouraged me to go to hair school. There’s Paul Mitchell School. It was the best school that I could go to at the time. It was about an hour away from where I lived but it was the place to go. I was resisting a little bit but I figured what, “I need to make a choice here. I’m going to go take a tour.”

    Are you going to school at this time or are you not showing up for school?

    It got to a point where I tried. I would be kept up all night with things going on in the house, oversleep, miss my bus and not be able to get there. I would stay after to try to make up credit, and then have no ride home and nobody to get ahold of for hours after the school closed. It was not possible. That was part of giving up on that. I didn’t get permission from anybody but I stopped going. At this point, you could consider me a runaway but I wasn’t reported out as a runaway. I was still in contact with my grandparents and daily, checking in with everybody but my mom was trying to have me put in a mental institution, to be honest.

    I don’t want to villainize her here because it’s understandable that we all went through a lot and we had to cope with it the way that we coped with it. For her, there’s a little bit of that deflection. She wasn’t in the right mind. That’s unfortunate. We could talk about the medical system and overprescribing of drugs and all that. Regardless, without blame, I knew that I was sane. I wasn’t a bad kid. My intentions were good and if something bad was going to happen to me if I was in that environment of toxicity and her own drug use, her need to control me and the idea of being put in a cage or some type of program until I’m eighteen was the scariest thing I have ever had to think about.

    Truly the hardest thing I went through was the idea that I could get picked up and taken away at any moment because it did happen where I’ve got taken somewhere because she said I was a danger to myself. They evaluated me and said, “You are okay to go home. We are not going to hold you here.” She kept pursuing it and that’s how I’m like, “I’ve got to get out of here.” That was a real moment. It wasn’t like, “I want to hang out with my friend.” It was like, “If I stay here, she’s determined that I’m not okay. She’s determined to make that happen.” That was when I was like, “I’m out.”

    My grandparents were very supportive. They wanted me to live with them but they were also captive to her emotions at that time. After I had gotten away and stayed at the friend’s house for a little while, I finally said, “She’s got to understand that you are going to come to live here.” I was happy to do it. At that point, I’m living with them, working this job, making money, I’m happy. It’s going well. We talked about going to hair school.

    Are your grandparents trying to get you back in school? You live with your grandparents, right?

    Yeah. They understood that the moment had passed. I was too far behind and they were supporting me in my new endeavor of working towards that career. My grandma is blind. My grandpa, I don’t remember if he was still working at the machine shop or not, either that or he was retiring at that point. They are not rich. We didn’t come from money. We are much like the lower-middle classes. There are a lot of obstacles at this point. My mom is not on board with any of this. My grandma had even said at some point, “If cops or whoever comes knocking on the door, you run out the back.” It is serious and hard to believe. Now it’s funny to me because it’s like, “I can’t believe that all this happened.”

    Even being a sane person and going into these mental institutions and then people there are like, “Why are you here?” It’s crazy. We go on a tour of the school. It’s an hour away. I do not have a GED. In the State of Florida, you can’t take a GED test until you go through six months of school. At that point, it seems counterintuitive or pointless. If I could go to school, I could go to school. I didn’t want to waste time and do a bunch of GED classes. That was not a priority. I didn’t have a license and I wouldn’t be able to get one because my mom would not have signed off on that until you are eighteen. You need a permit for a year before you can get a license. There are a lot of things holding me back there. I had saved a little bit of money so it was great but it’s $17,000 for hair school. We take a tour. I walked on that campus and I knew that that’s where I needed to be. All of those doubts went away.

    You walked into the Paul Mitchell School knowing you need a GED and you don’t have that. Knowing all those obstacles were there and you still showed up. What did you find out after the fact?

    I definitely knew that these obstacles existed and I was willing to put myself out there to figure it out.

    That’s something in and of itself. That’s what I want to draw out. For most people, we talk ourselves out of things before we even give ourselves a chance so often.

    I see that all the time. Once I set my sights on something, I do whatever it takes and that sense of being on my own even if it was more figuratively from the time that my brother and dad died. I developed that mindset that nobody is going to hand me anything. I’m going to figure out a way to get what I want.

    That’s a mindset shift right there.

    I don’t know where it comes from. I wish I could model that specifically.

    I can speculate that there. There’s some evidence that there’s a hereditary component to optimism. Some people are born naturally more optimistic than others. On the other side of the coin of the most prominent psychologist alive, who’s the Father of Positive Psychology, Dr. Martin Seligman is a self-proclaimed natural-born pessimist. You can definitely teach yourself to be optimistic but that’s an important component.

    It all happens. We toured the school. My grandpa, God bless him, drove me an hour out of town to go to this school. It’s so upbeat and it was inviting.

    You know you need a GED. You can’t get that you don’t have a high school diploma, it’s an hour away, you don’t have a car, you don’t have a way to pay for it but you still showed up to the school. I want to make sure that we put that out there. Grandpa takes you to the school and what happens?

    They take us around. It is a phenomenal school. They work with a lot of mindset training, multiple intelligence and how people learn. It was amazing. I sat down with the admissions officers and that’s where we started to make the plan. Asking for help is a big lesson that I would like people to take away from this and that I would take away. I wasn’t scared to ask for help. As much as I was independent and determined that I’m configuring things out with or without help, I was also willing to put it out there and grasp at whatever a little glimmer of hope I could find.

    Who were you asking for hope at the Paul Mitchell School?

    At the admissions, there are people in charge of getting students enrolled. The way we overcame some of these specific obstacles, the first one is the GED. They had an equivalency test that I was able to pay for. That would basically acknowledge, whether or not I could comprehend the material. Technically, I probably have a tenth-grade education and I did score college level so they accepted me on that account. In this day and age, you need a real GED so I’ve got fortunate there.

    Paying for it was financial aid. I was able to get my own student loans, under my own name. They were sent to work with my mom to try to get her to agree to my staff and some of the paperwork that we didn’t need her on. Until you are 25, it goes based on your parents but it was under my name so I felt good about getting my own student loans. She was reluctant but she agreed to me going to the school she did. Finding transportation was the big and final piece and then sure enough. Thankfully, there were 1 or 2 people that were driving from our hometown to this school that was more in the city. They asked one of them if she would be willing to have a young girl basically hitch a ride with her. We agreed to that and I would meet her every morning at a parking lot.

    My grandpa would take me up the road and we would drive together. This girl is a few years older than me. We were not a likely pair at first. I was young, enthusiastic and it’s annoying. I was talkative, young and he was a little bit older. She’s like my sister now. She was a maid of honor at my wedding. This was many years ago when this happened. We work together basically our whole careers and also have been through so much together. That opportunity and that outcome right there all lined up. I started school. I signed up when I was 16 about to be 17.

    How long did that take? Was that a two-year program?

    No. It’s a $1,200 course in the State of Florida. We went to day school, which goes fast. It’s 8 to 10 months, depending on if you miss school. Your friends there, if possible, I would show up early, I would stay late. I would volunteer for every single event and opportunity that they had. The structure of the school is such that you are partially in a classroom environment and you are personally taking clients and guests of the school for hair service. I was always looking for what opportunity there was to gain some experience or knowledge. I started doing mentoring. I would mentor the newer students coming into the class who were behind me.

    If I can get a ride home with Spring Hill at the end of the night, I would stay after for a nice school and tutor them. One of the educators at the school was an educator for the Paul Mitchell brand, which is separate, which makes it confusing but separate from the school. The company has educators that go off into the real world and asked me if I would be an assistant for him and he would take me to these different classes he was training salons at. I said yes to everything and anything, and was always grabbing the opportunity.

    If I didn’t have a client, I was following the instructor around while she trained the other students with their clients. That quadrupled the amount of learning and experience I was able to receive for my time there. I’ve got to have my honors and my Dean’s List classes. I’ve got all A’s in my testing. Getting the opportunity to feel I’m excelling in something was so fulfilling. I even kept showing up after my hours were over. I was like, “I’ve got clients in the book. I have to come back. You’ve graduated. Stop coming.”

    At that point, I was ready to do whatever this career put in front of me. A funny little story. We would have guest artists come in and speak to us. Salon owners would come in and ask, “Raise your hand if you want to own a salon one day.” I was the only one in that room most of the time that did not raise my hand. I did not want to own a salon. I had the picture in my brain that my future was going to be in editorial work and freelance being a freelance artist. I wanted glamorous travel celebrity work. That was where I was gearing up to do. That was the path I wanted to go on because, for me, that was the most success I could see in this particular industry. It’s so funny how many people did want to have a salon. It was everybody. You don’t want to go to school now to see it. 80% of the room will raise their hand if they want to have a salon. Any questions so far?

    No. I was so intrigued by this. Help me understand where you are. You graduated from this school. How old were you, seventeen?

    At that point, I was 17 going on 18.

    You are still living with grandma and grandpa, right?


    You don’t have a car yet.

    No car.

    You are thinking that you are going to become a celebrity hairstylist. What’s the next move? You are telling me, “Don’t come back to the school. You are done here. Go away.”

    My next move was going to find a city and move there. I thought about my options. My family is from New York so I’m familiar with New York but that’s a big and scary mean city for a 17 or 18-year-old. I thought about California. That’s clearly across the country. I still want to be able to fly back to see my family and friends. I am close with my grandparents and my family. I was looking around and all seems risky. I had an Uncle that was in Chicago. He said, “You will want Chicago. You should move out here.” I said, “Okay.”

    That was what I went with and I have never even seen or been there at this point but I agreed to this. I dragged my feet a little bit while I worked. I had already developed the following for hair color. I was hanging out with my friends. I was in Chicago by the time I was nineteen. I started putting myself out there. That in and of itself is quite a big path to carve out because there’s no, “You apply here and you are a freelance artist.” You have to look for avenues, create the connections and establish a portfolio. I was doing that and Chicago was fun.

    It’s interesting because kids who go to school to become lawyers, engineers or doctors once you step into that track, the system takes you. You walk out of school and firms are waiting to hire you. You step into the river and that river takes you. You are saying that’s not the case in your world. You had to go out there and make something happen. I want to point out that it’s different for different fields. You’ve got to figure out how to go out there and put yourself out there. What does that look like? You are 18 and 19 years old. You showed up in Chicago and you have never been to a big city like that. How do you put yourself out there?

    A lot of modeling websites are trying to establish relationships with photographers doing a lot of free work. I take any opportunity like I had been used to doing and grasping at whatever came my way.

    $25 a day and saying yes to everything.

    It was so much fun. It’s such a welcoming city. I met friends quickly. I’ve got a job, off the books, being a server at a patio bar. It was a welcoming, friendly and fun environment. I did whatever I had to do. I did a little commercial modeling myself. I did the serving and the hair. It was going. I was trucking along when I was there. It’s about my 21st birthday at this point. I had worked at a high-end hair salon as an apprentice. That was something important for people to understand. I had established myself as a hairstylist. I felt confident in my abilities and I was regarded well at that point.

    To get a job at a high-end hair salon anywhere, you have to apprentice, especially if you have only been doing hair for five years or less. You are earning the right to work under that name and that established brand and reputation. To charge $100 for a haircut, you’ve got to pay your dues. I humbly took a step backward to become an apprentice and to be honest, I didn’t see tons of value in the time that I was there. I didn’t have an extraordinary curriculum or anything but I was happy to do what I needed to do. There are a lot of cleaning involved in that job and hair washing. From that experience, what I didn’t know I would learn is how to structure a high-end hair salon because I had not been around that in my hometown. This was another level and a different level of service but I did get that experience.

    You are taking notes. That’s what you are saying. It was somewhat demeaning and a demotion. They weren’t apprenticing you. They were having you do menial tasks but you looked at it as an opportunity to learn about a big fancy salon. It’s all in the interpretation. That’s cool.

    I found a way to pay my bills. I didn’t need a car in Chicago. A couple of days before my 21st birthday, summertime in Chicago is no other. Everybody is so excited to get out of their apartments and over the cold. You see the city come alive. I’m so excited because I’m going to be 21 and officially legal and ready for whatever is coming my way. I had an apartment on the fifteenth floor looking at the lake. Things were awesome, then I get a phone call and it’s my grandma. She says, “Your Aunt Tammy is closing up shop.” This is my aunt that I used to shampoo for in my hometown and she had a lot of personal things going on. She had tried to sell the salon and it didn’t work out. She and my mom were there that night, unscrewing fixtures from the wall, breaking down the equipment, ready to put into storage and get out of their lease. My grandma asked me, “Do you want to buy this together?”

    Is grandma going to help back you on it?

    The going rate was $20,000. I had $10,000 when my father passed away in my Florida prepaid college account and my grandma said she would put in the other $10,000 she had that to invest. My first reaction was, “Heck no.” I am not going to be one of those people who gets stuck back into my little hometown. It’s not happening in a way so I feel good.

    You’ve got a taste of a big city salon. You saw a $100 haircut stylist. You are not going back. You didn’t say yes to that.

    My first reaction was, “Heck no.” I was at dinner with my uncle and he said, “Why don’t you go get it started and come back?”

    I’m like, “That sounds a little crazy.” We talked and the more I thought about it, the more I started to wonder what if I stay here and nothing significant comes of what I’m doing and I always have to wonder, “What if.” The idea of getting it started owning it, and then being able to do whatever I wanted was appealing and unrealistic. I said yes. As I have been doing for all this time, I always had these certain pictures of my future and success. One way or another, they kept being proved wrong, and other bigger, better opportunities were put in front of me and things that I was happy doing. I don’t want to waste an opportunity investment for me.

    Did you pack up your stuff and you went back to your hometown in Florida?


    What does this salon look like? Is it ready to roll?

    I had an apartment and the lease there. I let that sit there for a few months and didn’t take my return flight home because I had a flight for two days or a day after that call. I said yes. I was there within a day or two. I’m brainstorming and hypothesizing all of these future options. My roommate wasn’t too happy with me. I continued to pay the rent but we only had a few months left. I jumped right in. The salon, unfortunately, had deteriorated a little bit. Partially what was going on there was there weren’t any employees. There weren’t even any clients. There wasn’t anything for me to inherit other than equipment, which was what we were purchasing for and the liability of a lease. I had no idea what I didn’t know going into this. I tried to hit the ground running. I had two weeks’ worth of clients booked. After those two weeks, you are sitting there all day, every day with, “What now?”

    How did you get a week’s worth of clients?

    I had established clients in Florida in my hometown.

    People know you.

    I knew a lot of people from growing up there and I was always working to create an online presence. I would book a week or two worth of clients and fly back to Florida every month or two so I maintained a little cluster there. It’s a compliment when your clients wait for you to fly back or are willing to fly you back.

    You live in Chicago and you are flying back to Florida working in the salon for a week or two and then go back to Chicago at 21 years old.

    If I wasn’t working in a salon, I would do it out of their houses. It’s totally illegal. I’ve got to say, it’s what I had but I would line five people up and pull all their hair, “You go jump in the shower. I’m going to comb you. Come here.” I would juggle it all. I do what I’ve got to do. It was fun but I would not advise doing that again.

    What happened from there? You took over the salon in Florida but it sounds like you don’t have a clear vision yet? It’s like hobbling along.

    I had no idea where to start even. I started with the basics that come to mind when you are a hairstylist. What products are we going to have? What are we going to charge for things? I have always been good at marketing, expressing myself and putting it out there. I’ve got flyers printed up, the specials and I would walk. I have a license but I don’t have a car at that point. I would walk all up and down the roads, and the surrounding area and hand out flyers. I was hitting the ground running anyway I could.

    I didn’t have any other stylist for the first six months. I would make sure I was there when the doors said we were supposed to be there. Many times, I sit there all day with no clients. I would research a lot online try to find advice and metrics to judge my business against. If I was there all day and had no clients and three people hopped in for highlights at 5:00, I was staying until 12:00 to do them. It’s a whatever-it-takes attitude, trying to be reliable, and establishing a culture in a business that was branded in the way that I wanted this business to be branded.

    Fortunately, about six months in, my travel companion to the Paul Mitchell School, Ryon, was back from Las Vegas, which is where she had branched out to. We were reunited because we have always worked so well together and that it snowballed from there slowly and painfully. Some of the biggest challenges of starting a business with no background are not doing the technical work that I knew how to do. From doing all of the other things you don’t realize when you are running a business, whether it be always having to have your marketing hat on, be the janitor and the maintenance person, be aware of a profit and loss, and how you quantify a successful business. The biggest factor of all, for me, was my own personal development and the ability to lead a team.

    That is not something most people are born with even if they think that they are good leaders. I thought that I’m the owner, I have the experience and I have established myself as a successful hairstylist. I’m a hard-working, driven person. I’m a good leader. That does not equate to many people. Being a good leader is being able to achieve a result that you are looking to achieve with a group of people and having them feel good about it, too. For a 21-year-old, that is a strong personality and that doesn’t always translate well and half of the people I hired were older than me.

    What you are also saying that’s interesting and so many people get this wrong. The skills for being good at hairdressers to have almost no relationship whatsoever to the skills of running a successful hair salon. People make that mistake. They think that because I’m good at X, I’m going to be good at running a business that does X. The opposite is true in a lot of ways. Michael Gerber wrote a book called The E-Myth.

    He laid that out. I met him once I spoke with him at a conference. The thesis of his book was, “You are a technician having an entrepreneurial seizure.” For a lot of people, you don’t want to be bothered with the business stuff. You want to do the technical work without the inconvenience of a boss. You’ve got to figure out how to run a business, keep the lights on, motivate people, how to pay the bills and all that.

    It’s so all-consuming. Every minute of the day, there’s something I can think of that I could or need to do. It was a few years of me being the lead stylists of the highest producing stylists but as we grew, thankfully, I was able to accumulate some great team members. Slowly but surely, I started to seek the outlets that could provide the training that I needed to do a better job in my role as the leader. That meant I had to take steps away from doing the work behind the chair. You can’t do it all. I don’t want to shortchange my guests while I was thinking about other things that had to do with the business.

    You are basically developing your own curriculum. You said you stepped out of the salon to find other resources. Can you tell me a little bit more about that? Are you trying to find leadership training, training or business training? Where were you looking?

    Thank God for the internet. The software we had put out a lot of great content so I would study that. It would be quantifying the metrics of a hairstylist or a hair salon. That was the first piece of education that I worked on. It’s understanding my industry and my business. There are even more broad business concepts, profit and loss, and things like that.

    Ryann, did you at any time try to get entrepreneur training? Did you go to a Small Business Development Center? Did you write a business plan?

    No, I definitely didn’t. What I tell other people now is never start a business without a business plan or a partnership agreement. These are all huge. I have to say that my grandma and I have a lot of unnecessary conflicts even though we have all had each other’s best interests at heart. The book, The E-Myth, talks about this. It’s such a good book. I recommend that book to everyone and anyone who wants to consider owning or opening a business.

    If you go into business and you don’t have a clear vision statement on paper or picture of what the job roles are going to be for both partners, what the long-term or short-term plan for the company, you don’t realize it’s the honeymoon stage. “Everything is great. Everybody is going to do everything. This is going to work no matter what we have to do.” That will fall really quick. I wanted to grow the business consistently, long-term, reinvest everything I could and my grandma was not in a long-term state of mind. She’s older and trying to do something different, which definitely changes the way the business is going to be run and the choices we are going to make. We are 50/50 partners at this point so it created a lot of challenges by not doing the due diligence ahead of time.

    I’m fascinated by the way entrepreneurs learn and so many of us were not great students but we have this amazing ability to learn and find the information we need when we need it. There’s a point to be made here, Ryann, whether you are aware of it or not, even when you are in the darkest struggle, there’s something in your mind telling you to try, grow or figure something out. There’s a vision in your head. It might not even be a clear vision. That’s the common denominator, whether it’s a corporate vision or your personal vision. Bruce Lee said this, “The successful warrior is nothing more than a common man with a laser focus.” I’m saying the successful entrepreneur is nothing more than a common person with a compelling goal.

    If I was going to move back to Spring Hill, I was going to make this a success. I was not going to accept anything but that. There’s another book by Angela Duckworth called Grit that talks about the concept of relentlessness and even though there are going to be hard times, there are going to be times where you want to give up. The people that achieve great things are the consistent ones, keep showing up and keep with whatever they are focusing on. It’s not always the most talented or intelligent people. Pretty times, that buy the commitment long-term.

    I did decide to be talking about not being great in school and things like that. There are a lot to be said for creating your own education and cherry-picking the lessons and the things that you want to learn. We do that as a company now. One of our core values is the commitment to growth. That is a prerequisite for anybody who joins our team and that’s how we have been able to get where we are going. A lot of people do think I was crazy to start a high-end salon in a town.

    There was a place, at that point, that was charging $35 for a wash, cut and blowdry. It was fancy. That was pushing it. We have $110 haircuts at our salon. We start there but that’s where the levels go up. I’m proud of the fact that I did have a vision that we amassed a team of people that shared the vision and relentlessly worked toward it. There were definitely days where I would look in the mirror and be like, “I am so beaten down,” or overworking for me at the time. The conflict with my team members there were times that I could have easily thrown in the towel but my picture of the future was all I let guide me. I looked for mentors. That was another thing I did when you are asking how I started to build up this self-education.

    I asked the salon consultants from the different brands who are the best salon who are the picture of success to you? Who is the picture of success to you? I started cold calling them. A lot of salons were confused when I called. They are like, “What is it exactly that you are looking for?” “I’m trying to learn and I want to say hi to my friends.” One salon is cutting loose in Sarasota, the owner got right on the phone, invited me to come up there, shadow her for three days, and that’s what I did. That was fortunate because her salon was the type of salon that I aspired to have. There are a lot of great salons and businesses out there but I had a particular vision of what was important to me and how I wanted to do things that don’t always line up with how other businesses operate. That’s why I don’t compare us to any other business but this was a business that I could say, “They are doing things the way I want to be doing things.”

    I was fortunate in that way that our values lined up and our deals lined up but she was ten times my size, multilocation and everything. From there, she recommended that I get a business coach. There’s a company that I use called Inspiring Champions. That’s a coaching consulting company. At this point, we are only a couple of years in. I’m working behind the chair full-time. I’ve got a couple of other people doing the same thing as Ryon. We are hustling, working hard, booking ourselves solid and still often could not make payroll. My grandma is freaking out a little bit because she’s seeing some debt accumulate.

    We started with some debt, firstly, but we weren’t in alignment. I’m going to the seminar, not cheap and they want us to sign up for a $1,200 a month coaching package. Everything in me knew that this would be the answer to connect the missing pieces. This was going to fill in those gaps that I didn’t have as a hairstylist going into a business owner role. I was crying at this convention, saying, “We have to do this.” All the credit in the world to this company. They have a lot of integrity. There’s nothing pushy or sleazy about it, all the best intentions there. They talked to my grandma and they talked to me. They are like, “You guys got to get on the same page. We are pulling for you. How is it going to be?” I said, “I will take the money out of my pay as a stylist or whatever I have to do, I will make this work.”

    My grandma was very hesitant. We have the yin and the yang here of me being an all-in person and for being the steady, conservative person. From that point on, from not being able to make payroll sometimes or being so tight, we weren’t able to pay for that monthly coaching package. We always had enough money to pay for that in the bank when the payments came out. From there, I was able to add value, continue to work on myself, the company and have coaching outside perspective. It was such a great investment. That was the next step to transition me from a stylist trying to hold all the pieces together, not knowing what I’m doing to an informed business owner.

    There’s so much I want to dig into there, Ryann. Let me go back to the Sarasota shop. You had a vision in your head so you weren’t looking for somebody else to tell you how to do it. You were just looking for pieces and parts. You were looking for little ideas to add to your own vision. I want to come back to the mentoring thing aside from hiring a professional coach, which is awesome. I published a piece in Forbes about this. Probably the most powerful resource that’s available to anyone is reaching out to finding mentors like other successful business owners. They will want to help you and it’s free and we won’t do it. How many salons did you call where they were like, “What?”

    They didn’t even understand what I was asking because it was so foreign of a concept for people to do that.

    It’s embarrassing. Have you ever heard of this concept called rejection therapy? Do stuff every day that you are going to get rejected. It’s not a thing because, for a lot of people, that’s a paralyzing thought to call a total stranger and say, “I’m interested in what you are doing. Would you coach me? Could I come up and look at what you are doing?”

    I’m a stylist. I have to coach them through that for their work with their guests and clients. You are scared to offer somebody a solution to their problems that they might say no even if you believe that you need it. It is an unfortunate aspect of our mentality.

    I remember one time, I was trying to do a real estate deal but I had no money and I went to this real estate developer, he had these lots for sale and he was having a hard time selling them. This was in the early ‘90s. I asked him to sign over almost $500,000 worth of real estate to me with no money down. I would build houses on his land and then pay him plus a little premium every time I sold the house. I went to this guy’s office and I was totally intimidated. He was a wealthy dude. He had pictures of him golfing with celebrities and stuff. I was sure this guy was going to throw me out of the office but I was desperate. The guy said, “Yeah,” and he agreed to do it. I remember going back there. I had a lawyer draw up that paper.

    I went back to do it. I’m sitting in his office and I’m like a little kid looking around at all the celebrity pictures on the wall and whatnot. He signs the papers, he looks up, and he looks at me and goes, “Do you know why I’m doing this for you? It’s because somebody else helped me when I was coming up.” There’s so much of that out there and it’s free. You’ve got to knock on doors. You’ve got to get rejected. People are going to say sorry. I don’t know what you are asking for. People call it luck, though but it’s not luck. You are out there hustling. You are shaking the tree and most of the time, it isn’t working but sometimes it works.

    It’s like that Grit concept in the book. If you will let each no stop you, you are never going to get to a yes. It’s going to happen. You have to let it happen and get past it. It’s not personal.

    We get hung up in our minds long before. Warren Buffett said something to that effect. At a conference, he said, “Anybody here can do what I’m doing and maybe more. Those of you who won’t, it won’t be because the world won’t let you. It will be because you get in your own way.” The salon is starting to go and you are still sweating in payroll but there’s cashflow happening. You have hired a professional coach. It doesn’t seem you are as worried about learning how to be a hairstylist and now trying to figure out how to run a business. You said you had a vision. Can you articulate what that vision was and what is it you are trying to build?

    For one, to provide a luxury experience for guests in the area. There wasn’t anything else like that at that time in that place. I wanted to be the best version of a hair salon that we could be. That was on the service side of things. I also wanted to create a company where team members were fully supported and can achieve anything that they wanted to achieve in their careers. Everybody was humble, supportive and it was a real team environment. It’s a place that everybody could belong to. Those are the big factors there. I wanted us to be the best we could be and that was where it started.

    Two things are going on here. We talked about this. You want to be an awesome hair salon, you want the people and the customers to come there and have an awesome experience and you want to be the best at that but it’s also interesting to me that you want to create an environment that supports everybody that works in that salon. That’s about growth. Where is that coming from? You lit up when I said that.

    That’s my purpose. My purpose is to take care of people that agree to follow my vision. I want to be a great leader by being of service to others. I want my team to be great stylists and managers by being of service to the people that agree to come to spend their money with us. One of our core values is being of service to others, whether it’s your team members or the people that come in, spend their hard-earned money with us, choose us and never take that for granted. The aspects of service all around are so important to me. My purpose is to help people get what they want. We have that Zig Ziglar quote, “You help enough other people get what they want, you will have everything that you want or need.” It’s so true.

    I came from such a dark spot into this position and I never pictured myself doing any of this, whether it be the hair industry or even owning a salon. None of that was in my picture of myself but I believe there is a bigger purpose for me. Through doing this, I have been able to realize all that. If I can help a hairstylist that didn’t think they can make anything out of their life, get past poverty level, a single mom or this and that, work 3 or 4 days a week schedule, feeling good about what they are doing, making the money they want to be making and having that great lifestyle means so much to me.

    Where’s Salon Halo now?

    That commitment to growth is constant and never-ending. If you are not growing, you are dying. If you are growing, you are shrinking at least. That’s how there’s a stereotype in my industry of becoming the old outdated hairstyle. I have been doing this for many years. I could be washed up at this point. The same for the business. Trends are changing and you’ve got to keep that competitive edge. I don’t compare us so much to other salons or businesses. I try to be our own competitors so we can stay unique in our way of thinking. We have become recognized as 1 of the top 200 salons in North America. We have run for our education program. We are always revamping and adding to that. Before I turned 30, we did over $9 million in revenue. We have expanded our locations multiple times.

    My long-term goal is to have a cosmetology school where I can incorporate all of these different aspects of personal development, business, education, whether you want to open a salon or be the best stylist from a professional development aspect. Provide opportunities for great careers for people who want to do it. I’m always looking for the next steps, not only for myself, my company but for my team members, too. Some people maybe don’t want to do hair behind the chair forever and I’m always trying to figure out, “Do they want to partner in a salon?” That’s the only way I’m opening another one. I’m not opening a third salon unless it’s for a team member. If they want to be a consultant or coach in what we are branching out into doing or if they want to grow within the salon as management and leadership. That has been huge because you can’t do it all yourself.

    It’s cool how you’ve got to be CEO through the hair salon thing. That’s a cool story. I can’t help but ask you this question, Ryann. It seems all these pieces you put together of the struggle of your teenage years, your family life and the tragedy that your family suffered. The Paul Mitchell Salon was almost a safe place. That became your school. It seems you are putting that all together in a way that can help other people. It’s such an interesting story.

    A lot of people think that entrepreneurs are people that are outside the arena, particularly in higher ed. They often look at entrepreneurs as if it’s a scam like we are all driven by money. I wish people could see your face when I said that. I have interviewed people like you all over the world and that’s such a travesty to make that assumption. I don’t want to put words in your mouth but that doesn’t at all seem what’s driving you.

    I could have made a lot more money doing a lot of other things in a lot less time. We are a couple of years in business now. I’m making sure we are profitable. I’m comfortable. I would have made a lot more money at the time I decided to not do hair and going forward for many years. All that money that I take in, the profit part, is going towards advancing the company and definitely not what you should do if you want to get rich and have lots of freedom.

    This is maybe a little bit difficult to explain but when you are purpose-oriented, you don’t need ornamental things. Maybe it’s easier to talk about this one a lot when you don’t have the satisfaction of creating something or contributing to the greater good. When you don’t have that satisfaction, you want material things to fill the emptiness. People don’t get that. I have interviewed a lot of entrepreneurs. I’ve got a guy who became a good friend of mine, Patrick Hughes. He’s up in Seattle. He started a cleaning company. He bought a $2,500 carpet cleaning thing out of a credit card.

    His first job was cleaning a UPS Store for $20. It was your $25 a day story. He didn’t know how to use the machine. They locked him in there overnight to clean the carpet and he didn’t know how to use the machine. The guy came in the morning and the carpet wasn’t clean. He won the United States Small Business of the Year award. He’s got cleaning contracts in twelve states. He told me, “When I started, I wanted to be a millionaire. I knew what the house, the car, the clothes, all of that looked like. I looked up one day and I realized that was no longer important to me.” He’s got 150 employees and I’m like, “The responsibility for other people’s livelihoods to help them grow. The priority changes.”

    For many years, everything I thought about in terms of the investment of my efforts or what I cared to buy decorations for, was never my house. It was my salon. I drove this. I’ve got a new car. I have the same car 1 or 2 years into having the salon and comfortably until the point where other people are like, “You need to get a different car.” That was not what was important to me. Buying expensive clothes and things that weren’t what drove me.

    That’s a common theme I hear in an entrepreneur. In the Who Owns the Ice House? book in Clifton’s story, he was telling me about his Uncle Cleve. He said he was the only person in our community that put money in the bank. Everybody expected him to be spending this money but he wasn’t. He had five little businesses at a time when he wasn’t even allowed to go in the bank. When you have a purpose in life, you don’t need things. When you don’t have a purpose in life, you need things. It’s backward so many people get that wrong.

    It’s hard sometimes when I go and I speak to students, teachers and professionals about a hair salon. Specifically, at hair schools, they all want to have a hair salon. I have a hard time sometimes expressing why. They are like, “Why do you do it? If you don’t make tons of money right off the bat, you don’t get to work for yourself and do whatever you want.” You have to find purpose in the work itself and helping other people or whatever your mission is of your business. You can make money eventually and you can have freedom eventually but there’s something deeper to that.

    I’m fond of saying that when we have the freedom to pursue our interests and develop our abilities in ways that contribute to the greater good. We tap into the most potent form of human motivation there is called intrinsic motivation. We become optimally engaged and that’s what your story is about to me. I asked you this when I met you. I want to ask you again. What are your takeaways from your story? It seems like it’s less about hair and it’s more about helping others grow. Am I getting that right?

    Yes, 100%.

    It seems like the hair salon is just a channel but your hair salon is a personal development school.

    That’s the goal.

    That’s a cool goal. You are trying to help other people that might be in a situation you were in.

    I have gone through so much and it’s not a waste if it can help other people and if I can find a way to make the best of it. I can offer a reason.

    Let me wrap up. The final question is, do you have anything to say to people who might be thinking about starting a business or want to be entrepreneurial? What would you say to someone reading?

    First, what is yours why? Why do you want to do this? Also, understanding that because that’s what’s going to drive you. You are going to have times where you are not making a lot of money or you are working ten times harder than you otherwise would be so you need to know why you are doing it. You can make the most informed decision. On top of that, do your homework. Plan for it. Understand what the markets or what the business plan is like and get survey mentors ahead of time. Restaurants are very common. It’s another similar service industry business where people get into it because they like to cook. Do you know what the profit margins are? Do you know how to train an employee?

    There are so many things and systems that are necessary to make a business operate. Do your homework. Survey people that are doing what you want to be doing. When it comes to mentors, it’s hard to ask for help but I always say if you can try to be of service in any way to them that will help you make the connection. Don’t take advice from people who are living a life that you don’t want to be living. If they are examples of what you want to have then they are going to be great mentors. If somebody whose life is all about money, their home life is falling apart and they are trying to give you advice on how to live and that’s not what you want your life to be, consider that. You could take everything with a grain of salt but always consider the source.

    Ryann, thanks for doing this episode. Where can people connect with you?

    Facebook and Instagram. I have Ryann Halo as the new Facebook-like page. You can like that page. It’s connected to my Instagram. I’m working on my personal branding now. That’s my next step. I am creating a business for coaching and consulting. That’s an opportunity out there but I don’t mind helping out as a mentor because that’s something I’m passionate about. You want to find me on Facebook and Instagram. On Instagram, it’s @Ryann_Halo. On Facebook, it’s @RyannHalo. That’s probably the best way to do it.

    That’s a generous thing to do, Ryann. I can’t thank you enough for doing this episode. Your story is definitely going to inspire people.

    Thanks for having me.

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    About Ryann DiBenedetto

    Signing up for Paul Mitchell the School Tampa at just 16 years old, Ryann became known as one of the youngest up-and-coming leaders in the beauty industry. Ryann has a diverse background which includes, hair and makeup for on-site events such as photoshoots, fashion shows, weddings, hair shows, educating, coaching, and more.

    At just 21 Ryann settled down to begin Salon Halo. Salon Halo’s success is largely attributed to the deep community ties that have been developed over the years. Through giving back to the community where ever possible and a strong commitment to education, Salon Halo is celebrating 2 locations & 8 years in business.

    Ryann is currently working as a mentor in Salon Halo as well as traveling to grow herself and others. She maintains several days a month working with guests in order to stay current and in touch with the needs of Salon Halo. She believes in inspiring and empowering others to reach their fullest potential both personally and professionally.