Early Life and Education

TL;DR:

• Alex discovered her love for marketing in college, switching from accounting due to its creative appeal.

• She was creative and entrepreneurial from a young age, enjoying art, graphic design, and running lemonade stands.

• College was a valuable growth experience, offering personal development, networking, and confidence-building opportunities.

Q: Where are you from, and what was it like growing up?

I’m originally from a small town called Harvard in Massachusetts, now worlds apart from where I live in Charleston, South Carolina. Growing up in Harvard, a place with just one blinking traffic light, surrounded by apple orchards and churches, was a unique experience. It’s not what people typically picture when they think of Massachusetts.

As the oldest child and daughter, I had very typical “Eldest Daughter Syndrome.” I loved to take charge and help my siblings, like proofreading my sister’s essays. I enjoyed being in control and managing things. Both of my parents and even my great-grandfather attended Bentley University, which is where I ended up going as well. It felt like carrying on a family tradition.

In high school, I was more of a B student, which seems to be a common trait among entrepreneurs. I often felt like I was wasting time on subjects that didn’t interest me, like spending months on the Gilded Age in history class. Despite this, I loved learning and stayed active. I played field hockey, was the varsity tennis team captain, and served as an editor. My schedule was packed, and I thrived on that structured routine.

Q: Was entrepreneurship part of your life as a kid?

Yes, definitely. I babysat, taught tennis lessons, and had my own lemonade stand as a kid. I used to have lemonade stands as a kid. I researched permits for setting up my stand in the town center to maximize foot traffic. Whenever we ran out of lemonade, I’d improvise and switch to selling Kool-Aid. And when business was slow, we’d go door-to-door. I was always finding new ways to make it work.  I’d drag my siblings and friends into it, too, and we had a lot of fun with it. I think I’ve just always loved business and the creativity that comes with it. 

Q: Did you always know you wanted to do marketing?

When I was in high school, I had my heart set on becoming an accountant. I imagined myself crunching numbers behind a desk where no one would bother me—perfect for an introvert like myself. Bentley University, where I went to college, is all about business. You don’t really get a Plan B there; if you want to change your major, you pretty much have to transfer out. So, I declared as an economics and finance major because I wanted to make money—that’s where my values were at the time. 

But during my freshman year, I nearly failed accounting and quickly realized a data-driven financial career wasn’t the path for me. Around halfway through my freshman year, I switched to marketing. It felt more creative and seemed to be something I was naturally good at. I’m so glad I made that switch!

Q: Were you always a creative person? 

Absolutely. Growing up, I was always into art. I used to take art classes on an almost weekly basis. I like being good at things, and getting validation from my family and friends that I was really good at art made me continue it as a creative outlet. To this day, my grandparents will send me pictures of the art I did when I was 8, still hanging in their houses or sitting on their desks. I was also in the National Art Honor Society in high school.  

Q: Some young entrepreneurs go to college, and some don’t. What influenced your decision to go to college?

There was definitely an underlying pressure to go to college, especially in my town, which had some of the best state exam grades. In my eyes, it seemed like everyone who graduated went to college. The expectation was clear: go to college or be seen as failing. I wanted to go anyway, but that pressure was always there.

Looking back, I believe I could have built my business without a college degree. You don’t need a degree to be an entrepreneur; you can just do it. However, college offered me more than just education. My network and friends who were also entrepreneurs at Bentley inspired me and grew my confidence. Bentley is very hands-on; almost all our class projects were based on real companies and scenarios.

It wasn’t so much about the learning but how the experience shaped me as a person. While I may not have needed the degree to start my business, I valued the personal growth and connections I gained.

Q: Did you have any experience during college that impacted and shaped you?

Absolutely. COVID happened while I was in college, and it changed everything. Since we’re the same age, you know how it killed a lot of our late teen experiences. Being very introverted, I honestly loved the isolation.

During that time, I entered an intercollegiate marketing case competition. It was focused on rethinking Kodak and figuring out how they could get back in the game. I had a team of four, and we ended up winning the competition. Competing against schools like Boston University and Boston College it was a huge surprise and a big deal for us. I had never done any public speaking before, but since everything was virtual, I thought it was the perfect time to try.

Winning that competition gave me a lot of confidence and validation. It confirmed that I knew marketing and that I could pursue it as a career. 

Post-Graduation Journey

TL;DR:

• Alex faced months of job rejections (100+) despite being well-qualified, which was emotionally tough.

• She started City On The Hill Consultancy as a side hustle during her last semester of college, which quickly grew into a full-time business as of 2023. 

Q: After graduating in 2023, did you go through a phase of applying for jobs? What was that like?

Yes, I spent several months applying to jobs and getting no responses back. There were moments when I felt so hopeful, like when I received a phone call on a decision day from a job I thought I had nailed. I was sure I’d get it because they seemed to love me, but then they chose someone else. I broke down crying on the phone; it was devastating.

It was rough. Over those six or seven months, I had maybe five interviews despite sending out hundreds of applications. I felt I was well-qualified for an entry-level $45,000 a year job, with numerous marketing internships and experiences under my belt. I had worked so hard to set myself up for success post-grad, but seeing others with no internships land jobs made me feel like all my efforts were for nothing.

It was heartbreaking and very emotional because they build you up, making you think you’re all set, and then it all falls apart. Despite the heartbreak, I don’t regret doing all those internships. They were valuable experiences, even if the job hunt was incredibly tough.

Q: What pivotal moment made you launch your marketing agency, City On The Hill Consultancy?

The real turning point came during my last semester in college. I was a full-time student juggling an internship and an on-campus job, so my plate was already full. Despite the chaos, or maybe because of it, I decided to start my agency on the side. I think being the oldest of four has made me thrive in noisy, busy environments—I love commotion and having a lot going on.

I’ll admit I’m a bit of a workaholic. I wanted something productive to do in my downtime, so I thought, why not help other businesses? That’s how City On The Hill Consultancy was born. It started as a side hustle to fill my free time and quickly became a full-time endeavor.

Running the Business

TL;DR:

• Entrepreneurship means freedom; Alex loves setting her own schedule and balancing work with her personal life.

• She’s learned to ignore critics, adjusted pricing based on client feedback, and overcame imposter syndrome.

• Effective time management: Alex refers pen-and-paper organization and practices time boxing to stay on track and meet deadlines.

Q: What services does your agency specialize in?

I aim to be a one-stop shop for my clients, which can be challenging. My agency primarily focuses on SEO, including monthly blog writing, page optimization, and more. We also specialize in social media marketing, covering Instagram, Facebook, TikTok, and surprisingly, LinkedIn, which has become quite popular. Most clients want both social media and SEO, but others prefer just one. I try to be as flexible as possible!

We also offer Google Ads, Facebook Ads, email marketing, some branding services, and even help with pricing and financial projections. Essentially, while our main offerings are social media and SEO, we dabble in everything to best serve our clients. If there’s a one-off project, I’m more than happy to help, leveraging my experience to ensure they don’t need to go elsewhere.

Q: Out of all the services your agency provides, which ones do you personally enjoy doing?

I would say my favorite is SEO and blog writing. It’s something I really enjoy and I’ve gotten good at. Clients have seen fantastic results from it. For example, one client’s organic daily traffic went from six to 350 with just one blog post. Small businesses love this approach because, instead of spending $100 a day on Google Ads, they get evergreen SEO content that continues to attract traffic long after it’s published. This makes a significant difference, and it’s satisfying to see those results.

Q: What have been some of the challenges and lessons that you’ve learned so far in your journey with running your own business?

One of the biggest lessons I’ve learned is to not listen to the noise around me. There’s this Teddy Roosevelt quote about the Man in the Arena that I really like. It’s about not letting the critics who aren’t in the fight affect you. I’ve had to embrace that mindset over time. I had some support, but not everyone was fully on board with my decision to go full-time with my business. Some people would ask when I would get a “real job.” Fellow entrepreneurs supported my decision, and my boyfriend was especially encouraging. 

Another challenge I faced was figuring out pricing, which took me about 10 to 12 months. I struggled with imposter syndrome, doubting my ability to deliver valuable content. I initially charged $18 an hour, which seemed reasonable for someone with a bachelor’s in marketing. However, many small businesses couldn’t afford it, and I couldn’t go any lower and still make a livable wage.

Interestingly, some clients began giving me voluntary raises, telling me I was charging too little. This happened with three different clients who didn’t know each other. They insisted on paying me more, which made me realize I needed to adjust my pricing. I increased my rates and surprisingly attracted more clients. Eventually, they encouraged me to charge even more per hour, even though it initially felt undeserved.

I’ve learned that pricing is as much about perception as it is about value. Some clients won’t pay if they think your rates are too low, assuming your work isn’t great. Increasing prices can actually enhance the perceived value of your services. It’s a weird mind game but a critical aspect of running a business.

Q: How do you organize your schedule to manage your business?

I’m very much a pen-and-paper person. I’ve tried online task trackers like Asana and Trello, but none of them have worked for me. I keep a monthly overview calendar for bigger events and a weekly task notebook with checkboxes for daily tasks.

I also practice timeboxing, where I allocate specific times to specific tasks. For example, from 9:00 to 9:30, I might check client social social media pages, and from 9:30 to 10:30, I might have a call. This approach helps me stay on track, meet deadlines, and clearly understand what my day looks like. I find it incredibly helpful for managing my time and tasks efficiently.

Q: What are some big goals you have for yourself and your agency this year?

I’ve found it helpful to set the most ambitious goals I can. Sometimes, this leads to disappointment, but other times, it makes me say, “Wow. I really did that.” One of my lofty goals is to be on Forbes’ 30 Under 30. 

I’m in a great spot with my business right now, and if I keep growing at this pace, I’ll achieve the work-life balance I desire. Financial freedom is a major goal for me, along with the ability to enjoy life more—like sitting by the pool or coaching my kids in sports in the future.

Ultimately, I’m working towards that balance and freedom. I’m happy with where I’m at, and with the steady influx of clients, I believe the business will keep growing. I plan to bring on new people eventually, but right now, things are good, and I can’t complain about that.

Q: What does entrepreneurship mean to you?

For me, entrepreneurship is all about being able to play by my own rules. Maybe it’s the oldest child thing, but I’m not used to being told what to do—I like to tell other people what to do. Being in control of my business and my life is everything. If I want to sit by the pool at 11 am, I can front-load my work and then go do that. It gives you so much freedom, which is something money can’t buy.

Even if I’m making less than some of my peers, I have so much more free time. I can choose my own schedule, go to doctor’s appointments without needing approval, and attend sporting events whenever I want. My life feels completely in my hands, and that’s absolutely my favorite thing about entrepreneurship.

Personal Philosophy and Values

TL;DR:

• Inspired by family: Alex is inspired by her dad’s journey from financial struggle to success motivates a “can-do” attitude.

• Core values: She emphasizes honesty, family, and authenticity in her personal life and business.

• Mindset: Adopts a “we’ll see what happens” approach, staying open to opportunities without rigid expectations.

Q: Do you have any personal philosophy that has shaped your outlook on your business and personal life?

Yes, definitely. My dad’s story has had a huge impact on my outlook. He grew up in a family with five kids, struggling financially to the point where they would splurge on a single Bic Mac for all of them to share every once in a while. He had no clear direction after graduating from Bentley University. He tried various odd jobs, like selling light bulbs and working on building restorations. Years later, he decided to go to optometry school. My mom saw his vision and worked so hard to help pay for this education. Words cannot express how much I admire them both for dreaming big and working hard to make it happen.

My dad’s journey taught me that you can become whatever you want, no matter your starting point. It’s all about using your situation as motivation to get somewhere better.

I also embrace a “we’ll see what happens” mindset. I don’t set rigid expectations and prefer to be pleasantly surprised by how things turn out. This approach has worked well for my business so far. I stay open to opportunities and navigate life with an open mind, free from fixed expectations.

Q: What are some of your personal and core values?

Honesty is a big one for me. I’m a terrible liar—I have no poker face whatsoever. I could never lie to my parents, friends, or my boyfriend. While there are times I wish I could, I’m just overly honest. This trait shows in my business, and clients really appreciate it. For instance, if something only takes 15 minutes, I’ll tell them that instead of taking advantage and charging exorbitant fees. 

SEO agencies, in particular, are generally very expensive. While many small businesses desperately need help in this area, they cannot afford the prices. I want the best for my clients, so I’m upfront about costs and what they should pay. 

Last month, a solopreneur came to me asking for website help. I noticed they had over 400 pages on their website. If using the proper automation, I’m sure her ask would’ve been completed in 15 min. I don’t have any sort of automation that helps with this, so I would’ve had to charge a large amount for this work to get done manually. While it would’ve been great additional income, I told them to find someone who has an automation setup, as it would be significantly cheaper for them.

Another core value is family. I love building personal relationships with my clients. I know their kids’ birthdays and family dynamics and genuinely care about them. This value carries over to my business relationships—I make sure clients take time off for their family events, and they do the same for me. If I have any sort of event, they not only allow but encourage me to take the day off, which is so different from the corporate world.

Authenticity is also crucial. Being genuine in my interactions helps build trust and strong relationships, making my daily business enjoyable. So, honesty, family, and authenticity are my core values in my personal life and how I run my business.

Personal Life and Interests

TL;DR:

• Relaxation and recharge: Alex loves driving around with no set destination, enjoying sugary drinks and music to unwind.

• Unique music taste: She listens mostly to country music, including The Rolling Stones, Kid Cudi, Frank Sinatra, and more; she only has one playlist on Spotify. 

Q: What are some ways you take care of yourself and recharge?

It might sound a bit unconventional, but I love driving around with no destination in mind. Growing up in a small town with little to do, my friends and I would just drive around with the windows down, exploring Southern New Hampshire or Western Massachusetts. It’s become my favorite way to unwind. I try to do this once a week if I can, usually on weekends.

But it’s harder to do this in South Carolina, unfortunately. I thought New England drivers went fast, but that’s nothing compared to South Carolina drivers on backroads. So it’s less peaceful in SC.

I’ll grab a sugary drink, like sweet tea or iced coffee with caramel—those are my vices—and then just hit the road with the music cranked up. It’s so fun and relaxing for me. That simple pleasure of driving around, listening to music, and sipping on a sweet drink is my perfect way to recharge.

Q: What kind of music do you listen to?

I listen to a lot of country music, especially 90s country like George Strait. But my taste is pretty eclectic. I also enjoy almost every genre of music. I have one Spotify playlist called “Currently” that includes every song I’m listening to at the moment. People usually hate when I’m on aux because it can jump from Paul Simon to BROCKHAMPTON to Lainey Wilson, which is pretty chaotic. Maybe that reflects the chaos of my household growing up and my workday, but that’s how I like to listen to music.

Advice and Recommendations

TL;DR Version:

• Key traits for entrepreneurs: Emphasizes hard work, willingness to learn, and persistence for long-term success.

• Recommended resources: Suggests “The One Page Marketing Plan,” following @shwinnabegobrand on Instagram, and Simon Squibb’s YouTube video.

• AI tools for beginners: Recommends Canva for social media and CLAUDE AI for website copy and blog writing.

Q: What traits do you believe are important for someone considering entrepreneurship?

That’s a great question. The biggest thing, especially for Gen Z, is understanding there’s no quick way to get rich. There’s a misconception, fueled by social media, where you see a 19-year-old in a Miami penthouse claiming they work two hours a day and make millions. That’s not the reality of being a business owner. Most don’t have luxury vacations or a nice penthouse in Miami; it’s hard work every day, a full-time job, and then some. 

As Lori Greiner said, entrepreneurs are the only people who will work 80 hours a week to avoid working 40 hours a week. You have to be comfortable with hard work.

A willingness to learn is also crucial. With AI and other innovations, the way we do business is constantly changing. You have to stay up-to-date with trends and new technologies. Always be learning and set realistic goals. 

Persistence is another key trait. Many people start a business, and if they don’t see a return in two months, they return to their nine-to-five. You must be in it for the long run and not be afraid of hard work. Entrepreneurship is often glamorized, but it’s important to be realistic and prepared for the challenges.

Q: Do you have any recommendations for books, podcasts, or resources people should listen to?

Absolutely. For business owners who have no background in marketing and just want to learn the basics, “The One-Page Marketing Plan” is a fantastic book. It’s quick and very practical—I love it.

On Instagram, I highly recommend following Ashwinn, also known as @shwinnabegobrand. He shares great insights on packaging and branding. It’s fascinating to see what other companies are doing with their marketing, and you can definitely get some ideas to apply to your own business.

Another great resource is Simon Squibb on YouTube. His video “30 Years of Business Knowledge in 2 Hours and 26 Minutes” is incredibly valuable. It’s a free resource packed with insights from someone who has been building businesses for over 30 years.

Q: Are you a big reader?

Yes, I love reading! Throughout college, I read many marketing books and would reach out to the authors with my questions. I even asked about internship opportunities, and it’s how I got one of my favorite internships this way!

Reading has been a great way for me to learn and connect with experts in the field.

Q: What AI software tools do you recommend young entrepreneurs should look into?

Regarding software, Canva is great for social media, especially for people just starting out. If you learn to use it well, it can definitely be scaled. There’s a bit of a learning curve outside of using templates, but it’s worth it.

For website copy and blog writing help, CLAUDE AI is my favorite. It sounds the most human and is free to use. Plus, it scored the highest on IQ tests out of all the AIs. It’s an excellent tool for entrepreneurs looking to enhance their content creation.

Connect with Alex

Connect with Alex on LinkedIn and check out her marketing agency, City on the Hills Consultancy, here. 

You can book a discovery call with Alex if you’re a small business needing marketing services. 

Get Featured On Gen Z Acts 

Do you know a young entrepreneur (ages 12-27) who would like to share their entrepreneurial journey and business with Gen Z Acts? We’re always looking for inspiring stories to feature on Gen Z Acts. If you or someone you know is interested, please contact us at alan@genzacts.com. You can also refer an entrepreneur founder/CEO to us.

Stay Inspired and Informed!

Subscribe to our weekly newsletter and get the best resources and inspiring stories for young entrepreneurs delivered to your inbox. We promise not to spam or clog up your inbox 🙂 – just valuable insights and motivation to help you on your entrepreneurial journey. Don’t miss out, join our community today!

DISCLAIMER: This article is written in Alex’s voice. The conversation and answers are based on Alex’s responses and have been edited in collaboration with her to reflect her authentic voice and experiences.t.