Today, we sit down with Stephanie Riel, founder of RielDeal & Co., a brand strategy consulting firm based in Scottsdale, Arizona. In this episode of the Entrepreneurial Mindset Project, we explore the origins of an entrepreneur’s passion and drive.
Stephanie was inspired by her father’s journey as an immigrant entrepreneur and always knew she wanted to start something on her own. However, finding her true calling was a challenge. She persevered and ultimately found success, starting with nothing and using Craigslist to find her first clients.
During our conversation, Stephanie shares her insights on the value of side hustles, learning by doing, and the importance of having mentors. Her story serves as a reminder that when we combine our interests and abilities in ways that benefit others, we tap into a powerful force that ignites our passion and fuels our drive.
Listen to this episode of the Entrepreneurial Mindset Project podcast to learn more about Stephanie’s journey and the lessons she has learned along the way.
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Read the transcript below.
Learning By Doing With Stephanie Riel
In this episode, I’m speaking with Stephanie Riel, who’s the Founder of RielDeal & Co. a brand strategy consulting firm based in Scottsdale, Arizona. Entrepreneurs are often described as those who are passionate and driven. Yet the question is, “Where does that passion and drive come from?” Inspired by her father’s journey as an immigrant entrepreneur, Stephanie always knew she wanted to do her own thing. Yet finding her thing was not an easy path. Once she discovered it, she was all in. Like her father, she started with little or nothing using whatever spare time and money she could find to make it work.
In fact, she used Craigslist to find her first clients. In this episode, we cover a lot of ground from side hustling, to the power of learning by doing and surrounding ourselves with mentors. Ultimately, Stephanie’s story demonstrates that when we’re able to leverage our interests and abilities in ways that create value for others, we tap into something powerful, something that awakens our passion and drive. Without any further ado, I hope you enjoy my conversation with Stephanie Riel.
Stephanie, welcome to the show.
Thank you. It’s great to be here.
I appreciate you doing this. We need to broaden the conversation around entrepreneurship. Beyond the male-dominated tech startup realm, we have to democratize this and get people to think about it more broadly. Stephanie, I want to start with a question that I almost always start with, which is, what put you on this entrepreneurial path?
To answer that question, I have to go back. I had the sheer privilege of growing up and seeing the entrepreneur journey and the American dream in action. My dad immigrated to the United States at the age of six from Germany. By the time I was born, he was in his 40s. I got to see the life that he built, the freedom that he had, and the small businesses in our community in Cincinnati, Ohio, where I grew up, that we would support regularly for breakfast, banking, or whatever it might be. I always had a love for entrepreneurs and supporting small businesses. I had a tug on my heartstrings and I knew that it would be a part of my path too, even if at the time I had no idea what exactly it would look like.
Was your dad an entrepreneur? Does he run his own business?
He was in real estate. He started as a shoe salesperson. When he was first starting at five, he was cleaning shoes. His first official job was started selling shoes and clothes. The man that ran that clothing store encouraged him to go into sales. He took a roundabout way into it, but he got into real estate and was able to go at six years old, not even knowing English, learning it from watching TV and being made fun of in school because he didn’t know English to live the American dream, building a future and educate himself, becoming financially educated, understanding, and having that background, they don’t teach in school. In some ways, it is even more incredible to see, witness, and grow up around that too.
Kauffman Foundation publishes data about immigrants who are two and a half times more likely to start businesses than native-born. The effect is being close to it. It is super important. Did you realize there was a divergence, like, “I’m either going to follow a traditional path or make my own?” Was that ever in your conscious?
I don’t know if it was exactly conscious, but I will say that I always saw things differently. Even as a child, I always asked a lot of questions. I didn’t love school. I was the top seller in my Girl Scout troop. Every year I was in it. I always wanted to be out, making money. As very much children of immigrants that I’ve spoken to, education is always focused on in families and having that knowledge. It was very much something that I knew I had to do, but I didn’t enjoy it.
I wanted to go out and learn things by doing them because that’s always how I learned the best. Where that lit up for me started in high school, but then in college where I had more freedom to choose courses, and internships and get to set my own education by what I was learning outside of the classroom. I always knew that the path was different for me because I knew I didn’t want to go in into a traditional path of learning. I could see early on that I learned by doing too, which isn’t always supported in a traditional education model either.
Like you, I did not like school. I did well in elementary school, then I hit middle school and it was a downhill cliff. I know I’ve looked at the data. That’s pretty common. Student engagement goes down and down from 5th through 12th grade. The difference is you say that you didn’t think you were s*****. You think like, “I don’t like this kind of learning.” I came out of school thinking like, “I can’t learn.”
I know a lot of people that felt that way and maybe they learned differently. I was confident enough to know that it wasn’t me, but it was the school. I did have that. Also, my dad saw that I wasn’t interested in school and he wasn’t when he was younger as much either. He incentivized me for every A) I got money, every B) I got money, and C) Money came off the ballots. When I graduated high school, I was on the honor roll. In college, I graduated magna cum laude because I was incentivized to get good grades. It’s an incredible lesson and self-awareness to be able to see that for myself, but then also have my dad see it and help me succeed in a system I wasn’t interested in being in.
I want to dig into that in a minute, but something you said clicked in my mind. I never went to college, but I came out of school thinking it was me, “There’s something wrong with me. I can’t learn it. Everybody else seems to be doing reasonably well and I can’t seem to learn in this system.” It struck me. You said you knew it wasn’t you, it was the system. I was like, “It took me like another twenty years to figure out that it was the system, and I didn’t match.” I also want to dig into something that’s interesting that your father did, which is incentivizing you with extrinsic rewards.
I’ve studied motivation research and the outcome of extrinsic rewards is it tends to undermine the intrinsic desire to learn. It’ll get you to do the thing, but as soon as the reward expectation has been removed, typically, we no longer want to do the thing. You seem like you figured it out. That didn’t stop you, that got you through college. If I’m understanding you, you still had a knack for learning on your own.
The thing I loved the most about college that I did not enjoy when I was in elementary, middle school, or even high school was the choice I had about the classes I was taking. I went to college as a Music Theater major. I had done music and theater performances in high school. I was good at it and got into one of the top non-conservatory programs in the country, which was not a small feat, but in my first semester, I was taking classes on Music. Music Theory was one of the hardest classes I’ve ever taken in my life, but I got to choose. I wanted to triple major, but the music school wouldn’t let me do that. I dropped Music and focused on Business and Journalism, but I got to choose.
When I was more interested in the topic and I had more choice in being able to select the classes I was taking, I enjoyed college a lot more because I had more control over that. I went to Arizona State University. It’s a very large school, a very large campus. Some of our 101-level classes had 400 people in them. That learning environment was always hard for me because I would think of anything else I wanted to do other than being one of the hundreds in a class. When you get further on in the college experience, when the class sizes get smaller or you’re tangibly doing something out in the field, that was cool to me.
Sometimes I’m envious when I hear that. I want to think about it like, “If I could go back to college now, I’d be into it. The travesty is there are many kids who go to college. They’re not sure why they’re there. They don’t want to learn. They want to get the little certificate and move on.
That’s the wrong way to handle anything. If you’re going for whatever the piece of paper is, no matter if it’s in class or some other avenue that you’re doing, that is a perfect example of what you were sharing where you overlook the value. You don’t get the same value if you’re focused on that. You miss much along the way. In some ways, I envy those that didn’t go to college. The grass is always greener, it’s fine. I remember I was like, “I could be out working. I could be making money.”
Interestingly enough, there was a moment when I found marketing and it was this marriage of all the things that I loved much and storytelling, which I loved from journalism, data, and analysis because of the digital marketing side and having that instant gratification of knowing if your marketing strategy was working or not, consumer behavior, psychology, which was fascinating to me and creativity, which I attribute to my background in theater. I didn’t find that until later in my college journey.
There was a very brief moment when I thought about going to get an MBA. I had a conversation with my dad about it. He always wanted to hear what I had to say about it. He wouldn’t come right out and say what he was thinking. He would probably eventually be in the conversation at some point, but he wanted to hear what I had to say first. I was weighing. It’s like, “To pay more money to go to get a Master’s when I could be learning by doing and that’s what I’ve always loved the most anyway.”
He stopped me and said, “There you have your answer, it sounds like.” I’m grateful that I didn’t continue more schooling because I started my first business at 22 when I was a senior in college. I learned how to file an LLC. I used money from my college job on campus to pay for the filings. I set up a business account. There are many things that I did. I didn’t even google. I went to my local bank branch and asked them and they helped me out. I took on any contract I could and learned by doing. That was more aligned with me and who I am as a person than any other certificate could have been.
It sounds like you had a high degree of confidence in your own ability to figure things out.
I still believe everything’s figure-outable. I jump in without knowing the next step all the time and know I’ll figure it out.Everything is figure-outable. Click To Tweet
I got to meet and have dinner once with Morgan Freeman. He told me the same thing you said. He taught him how somehow to fly airplanes. He is like, “Once you develop that ability, it’s like the world is wide open to you. If you don’t have that ability, you’re stuck.”
You can get stuck. Our mind is powerful. My dad used to say, and I know that this isn’t his wording, it’s a famous quote, “If you believe you can’t, then you can’t. If you believe you can, you can.” I don’t know that I recognize the impact of those saying when you’re younger you’re like, “I get it.” I don’t think I got it. Now I do get it. It’s like, “That’s powerful.” I even taught myself how to ride a bike without training wheels. I had been holding onto the training wheels, playing it safe, and riding around in them for months.
I’m a ‘90s kid. I was born in the ‘80s and there was a new cabbage patch doll. If I learned how to ride the bike without training wheels, which we had been trying to do for a while, I would get the doll. I said, “I take the training wheels off.” I went out and I rode the bike by myself that afternoon. You say that helps me see that for myself in a different way too.
You started your first business at 22 while you were in college. Can you tell me about that a little bit?
I had this a-ha moment in my marketing class where I knew that was the path that I wanted to be on, but I didn’t have any traditional marketing experience. I had done all journalism internships because I was a Journalism, Business, and Music Theater majors for a while. I focused on Journalism heavily with a lot of my internships and that real-world experience. I didn’t have any business or marketing experience.
I was in my last semester in my senior year and I knew it was what I wanted to do. I knew that other people were going to be entering the workforce. It was in ’09 so it was a hard time to enter the workforce. I knew if I didn’t have some experience, it would be even harder to get a job. It was September. I started looking for contract work I could take on, filed for the LLC, and took those steps. I worked for a couple of different entities out here in Arizona where I still live and took on any marketing work I could to learn marketing by doing. I didn’t think too much about it. I just did it.
You’re still in school. You don’t have a degree yet. How did you find your clients? You set up an LLC so you could establish a name. Did you build a website for yourself or something?
Ironically, I did not have a website until I was in business for almost seven years. I did use, back then, Craigslist. Craigslist was big for finding different jobs or part-time work. There was a local job board here in Arizona for more creative types of jobs. I found my first couple of opportunities through those and through going through the application processing and getting them. I worked with a startup. They were the light rail here in the Phoenix metro area, which is where I still live.
The Metro Light Rail was starting. There was a startup with news and events all around the light rail. It had a little bit of a journalism angle to it as well. I got to write some stories for it. I was in charge of customer acquisition. I learned by doing and got people to go to the website, visit, and read. I also got to work with the Arizona Office of Tourism for the centennial celebration of the state of Arizona. We turned 100. That was a small contract from the start, but it was cool to get to be a part of that.
Were you surprised at the level of jobs you were getting, the professional level of people that were relying on you to solve problems for them? Did that surprise you as a 22-year-old?
At the moment, I didn’t think about it. Our young people have an amazing superpower that they can tap into where they’re fearless. You don’t know any difference so you just do it. I didn’t overthink it. I was just doing it. Thinking back now, absolutely. Even though I leveraged that experience to get my first full-time or real job, I didn’t have the level of experience to be in those doors. I was a great storyteller. I’ve always been a great writer and great with people.Our young people have an amazing superpower that they can tap into: being fearless. Click To Tweet
I leveraged the internship. I did nine undergraduate internships through the Cronkite School with different journalism entities. I had to talk my counselor into letting me do two of them at once because they were both rigorous. I had a lot of experience behind my belt that wasn’t marketing experience. I used what I had to market myself as best I could.
Did you write a business plan?
No. I still don’t have a business plan. That would be boring for me to write a business plan.
I work with entrepreneurship educators a lot and it’s amazing to me the ways in which entrepreneurship is portrayed in the classroom are divorced from the reality of what a typical entrepreneur is doing. I asked you about the business plan. Did you have to go get funding? People hear entrepreneur and they think, “I got to write a business plan, then I got to find somebody to give me money to do it.”
That’s never felt good to me. I’ve never done that. I’ve bootstrapped everything. I had a couple of on-campus jobs when I was in college. When I started that business, I was working two internships that both paid, then writing press releases, and doing anything I could to make extra money. I’m covering what I needed to cover and then anything that was extra went into a bank account. I didn’t touch that banking account. I lived the side hustle life, which people call it now. Back in 2010, my friends thought I was crazy because I was working all the time. I put all that money into a bank account that I set up in 2010 and didn’t even touch until 2019 when I left my full-time job.
Were you putting money away specifically to create some buffer for yourself?
I was. I don’t know if it was totally conscious of me, but I knew I didn’t want to do all that work and be working all the nights, and weekends and not have something to show for it. I put it away. I did that for nine years. I worked for other people the whole time. In my first job out of college, I was the very first hire for a construction technology company that wasn’t C-level.
I reported to the CEO, CMO, chief sales officer, finance officer, and all the C-level guys. It was a franchise model. I was the youngest person in the company by far. I was there for three and a half years, and I ran the whole marketing department for the majority of the time I was there because they were a startup and green. They needed somebody that had great writing skills.
I helped them develop all their marketing collateral from there I worked in a marketing agency and eCommerce startup. For any of the work that I did on the side for my business and clients, I had a full-time job. I didn’t have to touch that side hustle money. I set it away. It helped me when I left my full-time job in 2019 with no clients signed and still no business plan, I just knew I didn’t want to work for somebody else anymore, and it was time.
Near the end of college, you said you were 22. I’m presuming it’s near graduation, probably senior year. You started this side hustle out of nowhere and the Craigslist point I want to come back to for a second because people mistake opening a business from being entrepreneurial. Some people want to open a business and they need money for that. You need to rent the building, decorate it, buy the stuff, hire the people, and open the door. That’s being managerial. It’s not being entrepreneurial.
That’s more operational or managerial is how I would look at that.
It’s like franchise thinking. The difference is an entrepreneur is figuring out how to make themselves useful. Your story demonstrates and amplifies my idea to pursue your interest and develop your abilities in ways that create value for others. That’s the underlying logic whether you probably weren’t even aware of it.
I don’t think I was. I am now. That makes complete sense to me now. At 22, a senior in college, I knew I wanted to do it, so I did it. I don’t think I was thinking that at all. Nobody told me I couldn’t do it, why wouldn’t I try?
You weren’t trying to start a restaurant or a shoe-shining business. You were following the things that you were interested in. I don’t want that to get overlooked because that’s what puts the gas in your tank. That’s where the drive to figure it out comes from. When people start to pay us, there is validation. It’s easily mistaken for like, “It’s all about the money.” It’s like, “No. It’s not really that.” The payment represents a validation of me.
I’ve interviewed hundreds of entrepreneurs and some of them were very successful ultimately. I keep hearing entrepreneurs say, “It’s not about the money.” At first, I was puzzled by this comment, like, “What do you mean it’s not about the money?” Maybe that’s survivor’s guilt or something. I don’t want people to think I’m greedy or whatever. As I continue to hear it and understand it like motivation research, it’s not about the money. There’s a purpose-driven component.
I was having a conversation. I get asked a lot what I’m most proud of in my career so far or a campaign that sticks out. One of the first clients that always comes to mind, I no longer work with this business, but we worked with a brick-and-mortar med spa that launched in October 2019 for multiple years. During 2020, I helped her pivot her business from being retail only.
We got her online. We moved up a timeline so that she could start selling her products online sooner. She’s since been able to not only stay in business but buy a building, and expand her team and her service offerings. While I, by no means, am taking credit for her success and the work that she put in, our marketing work helped her stay visible and hit goals in 2020 that she wouldn’t have been able to hit otherwise. Many other businesses didn’t hit.
The work that I did with her and that brand is based on the East Coast is some of the most meaningful work that I’ve done in my whole career. I’ve worked for regional and global franchise organizations. I’ve worked in Fortune 10 companies. It doesn’t excite me as much as the outcome of helping that entrepreneur survive and thrive. That’s that purpose-driven for me. A perfect example of it is being able to see my work and the impact that’s had on a client.
It also occurred to me that part of the benefit that you would bring to a smaller company or a startup is you can see the potential of the idea unencumbered by the self-limiting beliefs of the founder themselves because there are lots of barriers out there. There are competitors and all kinds of challenges out there, but we self-limit all the time.
You gave me a major a-ha. I don’t know that I’ve ever succinctly said it that way, but the competition, we can always find a way or a strategy around, but if a client of mine does have a limiting belief that’s getting in their way, we have to tackle that first. Sometimes I have no medical degree of any kind, but it can feel a little bit like a business therapy session to get uncover what is that limiting belief that’s keeping them from hitting that next milestone.
I see it a lot with younger entrepreneurs. I’ve had the pleasure. I love mentorship and I mentor a lot of the women from that side hustle. I grew it into a full-service marketing agency for small businesses. We were a team of all females. Getting to help them even taking off I’m hiring them to do the job hat and saying, “You’re not charging enough. You need to be charging more. Charge me more, but charge your other clients more too.” Being able to help people get out of their own way is something that entrepreneurs have. You have to have that ability because some of the stuff that we have to navigate is hard. It’s tough, but to be able to give that gift to somebody else is special, too.
I’m 60-plus years old. That stuff still haunts me like, “What am I? How am I holding myself back?” I’m reading this book called The Expectation Effect written by David Robson. If you don’t expect it, you’re not even going to start swimming in that direction. That’s why I’m focused on the entrepreneurial mindset. It’s the underlying beliefs and assumptions that impact our life and behavior in many ways, of which we’re not aware.
I want to make sure I got the timeline thread. You’re 22 in your senior year of college, and start this on marketing thing, like, “That’s my jam. That’s what I’m going to do.” It’s a convergence of your creative talent, sales ability, passion for learning, and discovery. You launched this thing on Craigslist with no money or experience and you’re still going to school. When you graduate, you’re going to go find a regular job, or how does that work now then?
I graduated in December. I got my first real job in February. I was working. I had a couple of clients that I was doing pretty consistent work for each week. I was working from home before. That was cool for those clients before Zoom, but in February 2010, I landed my first full-time or real job. That was with the construction technology company. It was here in Phoenix. They were very much a startup as well. I still worked for clients on nights and weekends on my own time. I did that no matter the job I was working in for nine years. From 2010 until 2019, I did a side hustle.
That original business was your side hustle for nine years. I want to double-click on something here for a second. I found some research that a guy studied like the origins and evolutions of large established companies like Hewlett-Packard, Waste Management, Walmart, Microsoft, and Calvin Klein. He found out that these founders typically have little or no experience in their chosen field. They’re not writing business plans. They’re not doing market research. They don’t have access to money.
He said that $10,000 was the average startup capital. It was cobbled together from friends, fools, and family, credit cards, second mortgages, and savings. It wasn’t venture backed these are companies like Walmart, Waste Management, and Hewlett-Packard. He said, “Forty percent of the founders had no experience whatsoever.” It’s mind-blowing. When you look at that from a conventional perspective, it doesn’t make any sense.
When you understand the entrepreneurial mindset, it makes total sense because of the individuals on this opportunity discovery journey. The original idea isn’t the right idea, but it’s like there’s experimentation and adaptation. The lack of money works to the entrepreneur’s advantage in the beginning because if somebody gave you, “Here’s $50,000. Go open your marketing firm,” you probably would’ve gone leased an office and bought fancy equipment.
I will hire way too many people, but I wouldn’t have known what to do. It would’ve worked against me and I probably wouldn’t have been in business for even a year because you wouldn’t have known what to do with it. There’s a lot of research on lottery winners and how they end up finding themselves in either bankruptcy or other situations because they’re not equipped to handle that chunk of money. It’s a similar argument for entrepreneurs. A lot of the culture now with funding and VC back this and that, they’re celebrating getting the money and then, it’s like, “What are you going to do with it? What are you doing? How are you going to make money?” You can’t take an investment and call that a win.
You took Craigslist, which is a free resource in your spare time. You built what we could loosely call MVP. You put an ask out into the world and said, “Here’s who I am. This is what I have to offer,” and you get a client, then you build from there. Did you ever think, “I’m in over my head?”
All the time. I’m notorious for learning on the fly and taking things as I go. One of the things that the more entrepreneurs and founders I talk to, it’s something that a lot of times we have in common where “I take it on and figure it out,” but there were a lot of times I was in over my head, not as much earlier on, but past 2019, ironically into 2020, I started hiring team and figuring out a lot of those pieces. With entrepreneurship, there are always many new things you’re learning and struggles that can be a little overwhelming at times when you reach those different levels.
I had to learn that lesson painfully. I’m good at entrepreneurs. I’m not good at managing.
I don’t like managing either.
I had to hire for it because if you want to grow, it’s necessary. I’ve got a partner now, Rob, that’s phenomenal in that regard.
I love mentoring, but I don’t like managing. if I like to have a partner that can make the pieces work and then I want to be involved, be able to mentor, and help them in their career, too. You have to toe the line a little bit, but the day-to-day management is challenging as an entrepreneur to be able to have the ideas and to be the visionary, and then to also be in every single trench of every single challenge that’s going on in a day.
A lot of entrepreneurs fail because they can’t switch gears. If you’re good at the creative side, I don’t think you should necessarily try to become a great manager. It’s very rare that those two things are in the same human. It’s important that you recognize the need for it and hire for it or partner with someone. It works both ways because managers try to start businesses with a managerial mindset.
They don’t know how to discover, talk to people, or try things on a small scale. I like to use the term micro experimenting, which is what you were doing, and micro failure. You got this side hustle going, but you have a day job and I’m assuming it’s not the same day job for the whole nine-year period. Did it ever get to the point where the day job became boring and like school, you’re like, “It’s time for me to go do my own thing?”
In 2018, I was working for an eCommerce startup and it closed its doors. I had never worked in a real big corporation before. I had worked for franchise systems and in corporate for that. We had a large footprint, but never a large corporate entity. I had been interviewing and was in the process for a job with a top Fortune 10 company.
I took that position and knew after the first week that it wasn’t for me. I stayed for 92 days. That was the one time throughout that period of about three months when it got very difficult for me to manage my client’s needs and be committed to the business because if I’m fully employed, that’s my first focus. It has to be. I was very cognizant and mindful of not taking client calls during the day.
A lot of the work I was doing at that time didn’t necessarily need a lot of face-to-face timer meetings. It was a lot of stuff I could do evenings, weekends, and things like that. All my clients knew that it was a side hustle. That was clear from the start because it was important to me to have that boundary. It got to a point where when I was working for that corporation, I was working such long hours that I wasn’t able to give the same level of quality. I was burning out quite honestly, and didn’t like the corporate job at all. It did feel a lot like school. It moved slowly and it wasn’t the right environment for me.
The people were wonderful. People love corporate because the benefits are great, which was great, but it wasn’t the right environment for me. I flagged that jokingly. I was at orientation the first week and I knew it wasn’t a long-term fit for me, but I wanted to give it a try. I didn’t want to ever question or wonder or have regret.
It was during that experience that I had to pull back significantly from doing a lot of my consulting work, which was ironic because I left that job and had no clients or income. I had that account that I hadn’t touched in nine years that I was able to leverage to remarket and reposition myself they bring on clients in about the first three weeks. It was one of those periods where I was no longer engaged by the work at the full-time piece.
Do you know what it was like in the environment? Can you put your finger on it?
Yes. There were a couple of things. I don’t like to speak an analogy, but I was in internal communications, which I had not been in before. We were in charge of marketing to the employees. That’s very different from marketing to a consumer and doing a very visible campaign. That was very different for me, but also the amount of approvals and time.
In my first week, I completed the campaign that we were supposed to send out after the first 90 days. I had already written it, had it all ready to go, was ready to send it out, and then proceeded to wait for months for approvals then the position would change and a new stakeholder would come in who needed to give their opinion. They would then change, tweak and edit. We would be back to editing the same. It was a six-series email flow. Even by the time I left, that email campaign never went out. I had done it within my first week of being there.
It was the movement, the pace of the work and not being able to get it out there and to see data, action, and get that feedback that I was used to getting from digital marketing, which has such great feedback that you provide from what the work you’re doing. It stifled me. It felt very slow and boring, which is the best way to put it. It wasn’t any critique of the company in their process. I understand there are stakeholders that you need to have that feedback on, but it wasn’t an environment that I was able to thrive in.
What struck me is I worry about how many Stephanies are out there that have your talent and potential, but absent that side hustle experience. How many people find themselves in that? They come out of college, get their first real job, and are super excited about contributing, and then they realize, “This is this,” but they accept it.?
“You’re getting a great salary. You have great benefits.” It’s easy to become a little bit of a wallflower. I’ve never been good at doing that. That wasn’t right for me. I can’t speak for anybody else’s experience, but even my husband, for a very long time when we were first dating, worked in banking in big corporations. After the first week, I was like, “How do you do this? How do you not lose all of your joy, passion, and anything that makes you a human and feel? Even the offices themselves have awful lighting. You have a little break room.”
In my opinion, how we’re supposed to have a human experience? To take and think about those young, hungry, vibrant, and creative people that are going into the workforce if they work in corporate, I would bet there are a lot of Stephanies that are out there that are struggling and not enjoying their job, but they think that’s all there is.
There’s no alternative. That’s my point. I was having dinner in New York on Sunday night in Manhattan with my nephew. He’s not 30 years old yet, he is working in finance. He’s saying to me like, “The job is the job. I get my creativity somewhere else.” At 28? That’s not how it’s supposed to be. One of the things that you are saying without saying is that work and learning can be fun, and can be a source of meaning, excitement, and energy rather than like a slog. I don’t imagine you’re posting stuff like, “Thank God it’s Friday.” You’re thinking, “Thank God it’s Monday.”
I love Mondays.
That’s like the larger idea nested in the idea of entrepreneurship. The data show that 2/3 of workers are not engaged in their work and 2/3 of students are not engaged in learning. When you look at entrepreneurial people, they tend to be actively engaged, if not optimally engaged. It’s the situation. It’s not necessarily the person’s traits. It’s your relationship to the work, autonomy, and self-direction. It’s all those things that come together in a way that optimizes you.
I like what you said about the combination of your artistic, creative, music, business, and helping. There’s a guy named Naval Ravikant. If you don’t follow him, you should. Someone worked with him to write a book that he published for free called The Almanack of Naval Ravikan. You embody something he said in there that stayed with me, which is that you can escape competition by being authentic and no one can be Stephanie better than you. You found the right combination of your interests and abilities and you figured out how to create value with it. It’s empowering. That’s the magic formula as far as I can tell.
I appreciate you recognizing that in me by no surprise and no coincidence. A lot of the work I do now focus a lot on branding, strategy, and all those bigger pieces of a marketing puzzle. We are figuring out how to celebrate and be authentically the brand. I think about that little girl in elementary school and high school and trying to find my way. Thank God I found theater because I never liked playing sports, but I tried all of them but didn’t find one that fit. I found my thing. We have to try a lot of things.
I’m a big fan of Gary Vaynerchuk in a lot of ways. He reminds me of my dad with his immigrant spirit. He talks a lot about, “You have to try things. It’s like the flavors of ice cream. How would you know if you liked Rocky Road if you never tried it? You wouldn’t know.” As kids, we have this creativity and excitement to try different things, play different games, or experience different toys. If we let it, as adults, we can lose some of that.
I’m grateful I haven’t lost that because that keeps me authentically me and it helps me so much more in the work that I do. Thank you for sharing that. I haven’t heard of that book, but I’m excited to check it out following our conversation. Truly that authenticity is the secret puzzle for us as humans, but for all the brands or businesses as an entrepreneur that you’re wearing to begin. It’s what makes us unique. That’s the most celebrated by a community.Authenticity is the secret puzzle for us as humans. For all brands or businesses as an entrepreneur, it is what makes us unique. Click To Tweet
There’s much to unpack there. We all understand the economic impact of entrepreneurial behavior. No one would argue with that. I’m seeing scholars starting to recognize the developmental benefits, psychological well-being, and the tendency toward lifelong learning. Let’s double-click on that for a second. As entrepreneurs, we’re probably better at learning, unlearning, and relearning, which is a superpower.
It’s not because we are gifted necessarily or dispositionally endowed with that ability. It’s because we’re functioning in such a highly ambiguous environment where often our ideas are wrong. You go, “That seemed a no-brainer to me, and who knew it didn’t work?” There’s a malleability in our brains. We can’t afford to blame someone else when crap goes wrong either because there’s no one else you look around.
You got to learn from it and move on real quickly.
Can you talk a little bit about any dark moments, big mistakes, setbacks, and big challenges you’ve had as an entrepreneur? You’re probably going to say it is one of millions.
I don’t think about failure probably the same way the majority of people do I think it is because we have to try a lot of things. It’s cliché and I know it’s probably on a meme somewhere, but when you fail, you’re finding out a way it didn’t work. One of the things that may have been difficult for me when I was growing up, but as I’ve entered into this world of entrepreneurship, I had to let it go real quick.
When you fail, you have to figure out the lesson, learn from it, and move forward. You can’t hold onto it because the longer you hold onto it, the more damage you could do. I don’t often dwell on a lot of those failures because it would take me out of that energy that I need to be in to create and put more positivity out.
We’ve talked about the biggest thing a lot already. I’ve learned it with one of the mentors that I’ve worked with. When I started my first business at 22, I didn’t have a business plan. I didn’t have a goal in mind. I knew I wanted to learn marketing and have a vehicle to do that. I had this feeling or nudge in my heart that I was going to be an entrepreneur, but I didn’t know what that meant. Because of that, I had a side hustle for 9 years, and then, for 4 years after that, I had a full-service marketing agency. I never was intentional about building it.
I was following the momentum where it went. That’s something that I’ve been sitting with a lot, “How do I build for the future with the intention that’s going to be in alignment with who I am and what I want?” I had burned out working for other companies before, and I told myself I believed that I couldn’t burn out in my own business. It was my own business. I wouldn’t burn out, and I found myself in a state of burnout in 2021. A lot of it was because I didn’t have the intention or the alignment with what I wanted, even my day-to-day to look like, or the kind of work that does light me up.
I built this school service marketing agency, but we ended up doing websites, social media, ads, and all the different pieces. I knew how to do them. I’m good at doing those pieces and had great team members and specialists that were coming in to help with certain parts. A lot of it was because I was seeing small businesses being taken advantage of and I didn’t like that I wanted to help them, but maybe that wasn’t the ultimate best reason to add those services in. Especially some of them weren’t as profitable as they could have been.
When I think about failure and what I’ve been learning, it is about having that intention and that focus set first because once you have that, it’s that North Star. It helps you change the way you make decisions. You’re not going to make a decision for a reason that isn’t aligned or that might end up causing you more damage in the future.
You’re saying yes to everything, which is necessary in the beginning. It’s in my way of thinking. You’re starting out and you have to do that.
I wouldn’t know how to do it another way. If I was in mentorship calls with young people who are starting businesses, I tell them they have to taste a lot of things and figure it out. I wouldn’t know another way to do it. You got to say yes to a lot of things.
You get busy and overwhelmed in the process, and you realize, “I like this kind of work, but I’m not keen on that kind of work. “You create the luxury for yourself where you can sort of parrot down a little bit.
The things that we say no to sometimes can be our best because it can open us up to being able to say yes to something else that is more aligned, fulfilling, or exciting. It makes way for others to jump in and step in for those areas that we’re saying no to for them to step in. It’s a win-win.The things that we say no to can sometimes be our best because it can open us up to being able to say yes to something else that is more aligned, fulfilling, or exciting. Click To Tweet
Back in the day, in the late ‘80s, I started a business with a borrowed ladder strapped on the roof of my car. I had no money. I had nothing. I was offering to clean leaves out of people’s gutters. Twelve years later, I was doing $5 million in revenue. I started out saying yes to everything then honing in. I made plenty of mistakes along the way. I want to come back to about mentors. I know that you’re passionate about mentoring. Do you have mentors? If so, how did that come about?
My very first mentor was my dad. He passed in 2013. A lot of the lessons that I learned from him continue to serve me in my life now. I’m grateful for that. I know not everybody has that kind of mentorship. I’m grateful for that. When I went out into the real world and got my first job and started working for other people, I thought that I’d have mentors, but it didn’t happen. My first boss, I looked up to him and learned a lot from him, but it wasn’t necessarily a mentorship. He was my boss and taught me things, but there was a level of mentorship there.
I went for a long time without any mentors. I do have a couple of women. I worked in their marketing agency and they’ve been incredible mentors to me in my career when I worked with them, and even since, they’ve been a great referral source for me. They’ve helped me learn so much and I’ve admired them so much that they’ve been mentors, even if we haven’t been working closely together. Where that changed for me was in 2020.
I sought out and hired mentors for the first time. I joined the buzzword, the mastermind, but a group of entrepreneurs. I’ve been in a couple of those different groups over the last couple of years where I’ve gotten to learn from the person who brings us together, but oftentimes learning much from the other members and the other entrepreneurs that are in there too, and the friendships that we’ve made and being able to support each other through the ups and downs of running a business.
I started mentoring younger freelancers, want-to-be entrepreneurs, and entrepreneurs because I didn’t have that consistent presence of that other than my dad and learning by example. Gandhi’s saying, “Be the change you want to see in the world.” I’ve let that drive a lot of my life. Wanting to be a mentor and a good colleague to honor and thank some of those good colleagues I’ve had along the way because it wasn’t always super consistent, but I have found so much value in the different entrepreneur groups that I’ve been engaged with, both connecting with the other entrepreneurs and the people that are organizing the groups as well.
The real benefit has been continuous learning and more of that safety to be in a container and to be with a group of people who might have a totally different business, but they can understand the season you’re going through in your business because they’ve gone through something similar and the camaraderie that you have through that has been incredible.
I think and write about that point a lot. I was thinking about this in my own life. I’m surrounded by people predominantly who are way smarter and more successful than me. It’s awkward as hell, but it’s a superpower that is available to anyone. I have a mentor that is 29 years old. I’m 63 now in 2023. The part of it is humility. I’m assuming that this kid sees the world in a different way. He’s a computer scientist in Italy. I meet with him once a month. People understand that entrepreneurs will almost always try to help other entrepreneurs.
I’ve studied this. It’s called a network effect. In social psychology, it’s looked at as the most potent form of influence on behavior in our informal peer groups. What most of us tend to do is surround ourselves with people that think more or less like we do. People in our same socioeconomic and same political realm. It creates this self-fulfilling prophecy.
It almost becomes an echo chamber. I’ve always thought that’s boring. If I don’t see something the same way as you, I want to ask you a question and understand why you see it that way. I’ve always thought that is cool to understand and get to know people. Traveling does that a lot too, because you get to see how other people live.
In the United States, we are lucky for many of the things that we have. When you get to visit other cultures, you get to see how they live, what their houses look like, and what a meal looks like on their table. That perspective is everything. When we get too comfortable in that and we’re around all the same exactly how we think, we are stifling our growth.
For the aspiring/struggling/nascent entrepreneurs who might be reading this, the single most important thing you can do is what you said. Find an informal or formal group of other entrepreneurs and find a way to work your way into that group because the rising tide lifts all boats. There’s a nuance that might be worth thinking about, which is that a lot of what you know, you don’t know that you know.
That’s called tacit knowledge. It’s the knowledge that we acquire entrepreneurs not through formal learning, but we acquire it through experience and it’s the knowledge that we acquire without effort or awareness. For example, grammar. You learn how to speak English by the age of five or so, a very complex rule system with no instruction from anyone. You probably to this day can’t explain to another human being how to write a proper sentence.
That’s tacit knowledge. The brain’s ability to learn implicitly like that is vastly more powerful than our ability to learn in a formal way. If somebody were to sit you down and try to say, “How did you become successful?” your surface answers aren’t going to be that meaningful, “I worked hard and never gave up.”
Hanging around other people, the way to transfer that knowledge is through frequent face-to-face interactions. You absorb it. To put a point of what I’m saying, for the nascent entrepreneurs who might be listening to this, that’s probably the single most important thing you can do. Be wary of experts and the people that tell you they think they know about entrepreneurship.
That is the one caveat I give. Mentorship is great. You can even learn from people online or from those you follow. In starting out people can be discouraged because of some of these “mastermind groups.” It’s such a strange word, but that’s a lot of times what they’re called. They can have a high price tag. You can choose and select who you’re following online and what they’re doing. There are many thought leaders out there that have done it, that are talking about it or sharing their expertise, which is the amazing, beautiful, and positive part of social media. Do be wary.
Before you ever would hire a mentor, please make sure that they have done something or are somehow connected to something that you aspire to be. You wouldn’t maybe take business advice from someone who’s never even started a business or thought about what it takes to have a business. Hopefully, you wouldn’t take maybe medical advice or legal advice from non-doctors or non-lawyers.
That caveat is important to share because there are a lot of people that because of social media have a platform. They’re trying to sell you into X, Y, and Z programs and they haven’t accomplished what they’re trying to teach others to do. That’s a slippery slope where you can get bad advice or be around. That is something to be wary of.
We should probably talk about this as well as part of this conversation. Especially if you have a good idea, there are people that are waiting to take advantage of you that portray themselves as mentors or support people. They want to take 20% of your business for a few thousand dollars. I had one guy tell me right in this category. This guy came to me and said, “I’m going to invest $500,000.” I was pretty new. I was trying to figure out what I was doing. $500,000 was a lot.
I didn’t have the right vibe from the guy. I’m glad I’ve never taken venture capital. I considered it a lot in the early days and I decided not to do it. I have lunch with this guy. I’m like, “Explain to me, you’re going to invest $500,000 for 20% of the company.” “Here were the terms.” “That’s a $2.5 million pre-money valuation.” All I have is an idea at the time, “It’s not.”
His terms were this. He’s going to go to the bank and borrow the $500,000. He’s going to loan it to me. I’m going to pay it back and he’s going to get 20% of my company. When he said it to me, my brain went, “Wait, what?” I said back to him like, “Let me make sure I understand this. Do I have this right?” He said, “Yeah.” I said, “No, thanks. Check please.”
“How quickly can I get out of here now?”
There are a lot of people that when you’re young and eager, it’s easy to get fooled and get tricked into something. You got to be careful there. There’s another thing I want to ask you about. You said paying mentors. I’ve never heard of that. I always thought of a mentoring relationship as more of a benevolence thing on behalf of the people that are mentors. Can you say more about that?
Something that I have seen a lot of in the last couple of years on Instagram and elsewhere are coaches or people who sell you into a coaching program where they become a mentor but you’re paying to be a part of the program. A lot of masterminds are like that too. One of the concerns that could come up for someone who’s new, maybe they have an idea, could be some pressure to feel like, “I have to pay to work with X, Y, and Z.”
That might not be the case either, but if you are going to pay someone, make sure that they’ve accomplished something that you perhaps have a similar goal for or they’ve somehow achieved things that track on your path as well. There are a lot of people out there that are taking money and being paid as coaches, but they have been done anything in the area that they’re saying they have. I’ve seen some friends and colleagues not have the greatest experiences too.
You are pro more to business coaches. It’s easy for people to get susceptible to that. The point that I’d like to make around what you said is there are plenty of people in your community who will help you. They don’t want money from you. I would start there. My point is we’re vulnerable when we’re excited about starting a business and having freedom and that we are subject to all manner of cognitive biases. We think, “If I can pay this person this amount of money, that’s the easy button. I won’t have to think for myself.” I don’t think there are any real shortcuts. Overnight success takes twenty years.
Depending on it sometimes and I’ve worked with a couple of coaches and they can be a support, ally, resource to you, and help you think things through in a way. The reality is you are still making the decision. You still have to take the action. No one’s going to take that action for you. It’s not how it works. That is something that I agree with you completely.
There are people in your community that would be delighted to mentor and help give their input. You can maybe even learn by shadowing them, things like that are more of an education than some of those coaching programs could be as well because the intentions of some are unfortunately something to keep an eye on.
I’m not saying all coaches are bad or whatever.
We always want to keep a lookout just in case because when you have that new idea, it’s the most exciting part where you’re excited. You have a great idea. You think it has great legs. You’re susceptible to feedback at that time from a coach or even family. One of the other things that came to mind that I want to share on this topic for those that are reading that are at that stage is to remember that feedback is one data point and that you’re going to receive feedback.
Sometimes family is the hardest where the feedback or the criticism that you receive might be an example of a limiting belief that that person has. It doesn’t necessarily mean that you need to adopt it or soak it in like a sponge. That’s something that we sometimes don’t remember with criticism and can let other people’s limiting beliefs impact how we show up in the world too.
Sometimes the people closest to us give us the worst advice. They want us to take the safer out. They have our best interest in mind. It makes people uncomfortable also. When you step out and do your own thing, it makes people uncomfortable. A lot of people will try to talk you back into staying with the crowd. I want to double-click on something you said when I asked you about failure and setbacks. You very quickly said, “I don’t dwell on those things. I learned from them.”
I want to end on this idea or let me try to string a coherent thought together here. The concept of resilience comes from optimism. I’ve studied this fairly extensively. You demonstrated that. The way that we interpret adverse events in our life has such an enormous impact on our ability to get back up stronger than when we were. It’s this idea of anti-fragility. We don’t just get back up, but we get back up stronger. That comes from what a psychologist would call an optimistic explanatory style. That’s what you demonstrated. You said, “I don’t dwell on those things. I learned from it. I move on.”
That’s an important tool that you probably do naturally, but it’s an important part of the story and the journey. Every time shit goes wrong, if you start telling you go into a doom loop because shit’s going wrong all the time. I want to ask you one last question about your vision. Where are you going? Are you starting to say no to things? Do you have a clear vision or a general thing you’re moving towards? What do you think about that?
I have a couple of different ideas and points that I’m moving towards. Usually, around this time of the year, I’ve been working on getting out of a lot of that force energy. I used to do a vision board, “I had to do it by January 1st. If I was working out, I had to work out for 45 minutes and it had to be this.” That’s not how life is. I’ve learned so much and built a lot of this resilience from entrepreneurship and being able to understand myself, life, and the things that I’ve navigated. I don’t necessarily have like, “In five years, it’ll be this and that.” What I am driving towards and what lights me up is being of service.
That’s the big picture. I have such a knack and a passion for strategy that I know that helping businesses with brand, strategy, and creation will be a part of my path for now and forever. Mentorship is going to be something that I love and I do, but I’ve not talked about that I do. I went to high school in Cincinnati, Ohio where I grew up. I’ve been mentoring a student. She’s a freshman in college, but we started working together in her junior year. I don’t get paid a dime for that and never would want to.
It’s exciting to me to get to hear that she trusts me for us to talk about things that are going on in her life. Something that’s been on my heart to do more of is more mentorship at a lot of different levels. I’m exploring different ways to do that because being of service and living a life where service is involved is where I thrive the most. My creativity blossoms from there as well. That’s one thing that I am focused on finding other ways to be in service on a very tactical and tangible side of things.
I have a couple of digital courses. I’m looking to do more with that as well so that I can share more of my expertise with others and empower those bootstrapped entrepreneurs and business owners that maybe that are doing it side hustle and are doing it all themselves, but they can do it in a smart and intentional way, and understand the basics of branding.
I have another course on Pinterest that I am passionate about because it works. Unlike other social channels, you do it once. It can work for you years in the future. I’m working smarter, but helping entrepreneurs take command of their branding and their business, and not have to break the bank to do it either.
The service thing is what I come back to. When you look up the definition of entrepreneurship, it’ll say, “Someone who takes a risk in exchange for a profit.” I’m not interviewing the big-and venture-backed entrepreneurs, but I’m not seeing that in the entrepreneurs that I’m interviewing. You got to make money. Money’s important. There’s no denying that, but there’s a purpose that’s part of the secret sauce. The service is like contributing to others as we empower ourselves. I don’t mean economically. That’s what we’re all supposed to be doing. Thank you for doing this. Where can people contact you? How best for people to reach you?
Thank you much for sharing this story. I got energized talking to you. I’m sure that lots of other people will have the same reaction. I appreciate your time. Thanks for doing this.
I loved our conversation. It energized me too. It’s something that I found much value out of as well. Thank you so much for having me.