Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur“ we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Cassandra D’Alessio .
Cassandra D’Alessio is the founder of Next Page Brand Strategies, Inc., a marketing agency dedicated to helping businesses tell authentic stories that build brand loyalty and drive customers to action. Since 2007, she has held a variety of marketing leadership roles as well as a visiting lecturer position at the University of North Carolina — Charlotte. She earned her B.A. in Creative Writing from Miami University (Ohio) and her M.A. in English Literature from the University of Louisville. Her first book, “This Won’t Be Pretty,” was published in 2020.
Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
Cassandra D’Alessio: I have a rather unique background that led me to entrepreneurship. I’m actually a teacher by trade. I taught first-year English at two- and four-year colleges for about six years after I earned my graduate degree. Unfortunately, teaching in higher education is not always financially doable and after some life changes occurred, I needed to return to a more stable salary. When I was in graduate school, I was a marketing assistant at an energy management firm, so I decided to return to that work, but in the non-profit space. I loved working as a Marketing Director, and it gave me the opportunity to experience everything a marketing agency provides on a regular basis.
What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?
Cassandra D’Alessio: I’m like a lot of entrepreneurs in this journey — I had a few bad weeks at work. A friend at the time, who was an entrepreneur, encouraged me to consider starting my own business. As I began interviewing for other positions at other companies, I realized that none of the jobs were exactly what I was looking for, and I was worried that I might end up with another supervisor, or work environment, that I was unhappy with. When I began to toy with the idea of working for myself and having so much control over my career, I knew that there was no turning back.
In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?
Cassandra D’Alessio: Easy! I am NOT a natural-born entrepreneur. There are a lot of important life events that have given me the skillset to become an entrepreneur. For most of my life, I thought that entrepreneurs were born, not made, and therefore I never considered it an option for me. That’s where I got a lot of inspiration to write my book, and it motivated me to tell a different story. Many of the books I have read for or by women suggest women entrepreneurs need to have an assertive personality and/or are looking to build a multi-million dollar business with a life-changing service or product. Some female entrepreneurs are that, but many are not. I wanted my book to be a helpful guide for the rest of us.
Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?
Cassandra D’Alessio: Once I was introduced to the idea of entrepreneurship, a whole world opened up to me. I felt like I was finally meeting “my people,” who were genuine, hard-working, and who also had complex life experiences that built them for the life of being an entrepreneur. Meeting those people, especially single women like myself, continues to inspire me every day.
What do you think makes your company stand out? Can you share a story?
Cassandra D’Alessio: Honestly, what we do is very simple. We listen. Most of my team are writers, so we are trained to sit back and take in the information presented to us. Whether we’re helping to tell a client’s story or we’re working with them to solve a marketing problem, we work hard to validate the person’s experience and to educate and provide recommendations for how we can move forward. I’ve heard from clients, several times, that they can tell they’re being heard (in more ways than one), and that is such an important part of a business — no matter your industry.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Cassandra D’Alessio: The first would be integrity. Do what you say you’re going to do and if you mess up, own it, and remedy it if you can. The second would be sincerity. Whether it’s talking with your team or a client, sincerity builds trust in the long term. Lastly, I would say empathy. The ability to put yourself in someone else’s shoes, not to explain their behavior, but to use that as a guide for communicating with each other.
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
Cassandra D’Alessio: I don’t know if it’s advice, but it’s certainly a common mindset, especially in the world of entrepreneurship: hustle 24/7. This was the second inspiration for me to write my book. I wanted to tell a different narrative. Yes, you need to work hard, and yes you will sometimes have weird hours and work nights and weekends, but if you are working, non-stop, all the time, you are, in my opinion, A) not producing quality work and B) on your way to a breakdown (not just a burnout). No matter your job, our society has glorified this overworking mentality, and it’s very easy to fall into that when you’re an entrepreneur. Even though I knew better, I followed that mindset and ended up physically and emotionally burned out several times during my first year in business.
Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?
Cassandra D’Alessio: It’s funny, I have a whole chapter dedicated to this. That’s how strongly I feel about creating a healthy work culture. I would say first, practice what you preach. If I’m telling my teammates that they need to go for a walk, get outside, step away from the computer, then I need to listen to that advice as well and also take those important breaks.
I believe it’s also important to put it in writing. I’ve made healthy boundaries a part of our culture handbook. No one is expected to respond to a client at 10 PM on a Tuesday night (unless it’s deemed an actual emergency and then I’ll be the one to respond). Setting realistic expectations for your team and for clients, in my experience, leads to better quality work and a much happier environment.
What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?
Cassandra D’Alessio: Learn. Be curious. Study the one area of your industry that confuses or scares you. We all have those dark places in our industries where we’re simply confused by the newest trend or haven’t given an “old school” tactic a fair shot. Learn more about it. Learn how it could be successful for yourself or your clients.
Can you help articulate why doing that is essential today?
Cassandra D’Alessio: We’re all biased on what “works” or doesn’t in our industries, and I have seen too many smart people completely dismiss a service or solution because of their own biases which are almost always rooted in personal feelings versus facts. For example, social media is something “kids” do, or direct mail is dead. Well, guess what. Over half of the world’s population is on social media. And have you checked your mail today? How many advertisement postcards did you receive? You should know if these strategies work for your business and clients before you dismiss them.
What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?
Cassandra D’Alessio: There are two things I see often:
- focusing on the wrong details
- not knowing your client
The first is usually around a logo design or naming their business. Yes, these are important elements of your business, but they are just that — elements. They’re not the heart and soul of what your business does. I’m quoting directly from my book here, but “A crappy logo and a good service equals a successful business. A great logo and a crappy service equals an unsuccessful business.”
Second, it’s so important to actually know who your client is (or your best guess when you’re first starting out). If you don’t know who this client is, there is no way you’re going to be able to find them, speak to them, or convince them to give you money.
Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?
Cassandra D’Alessio: I view it as a pendulum. At a “regular” job, the pendulum swing is pretty minimal. Having a bad day could mean a tough conversation with a supervisor, but a person likely still has their job and a paycheck. As an entrepreneur, the pendulum swing is more dramatic. Having a “bad day” could mean losing thousands of your own dollars due to a wrong decision.
Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.
Cassandra D’Alessio: When I was writing my book, I was reminiscing on what “milestones” or highs that entrepreneurs can expect in their first year of business and, honestly, they sound very simple but they are major. To name just a few, attending your first networking event, sending your first proposal, and receiving your first referral from a partner. Although these will eventually become regular occurrences, I still find myself feeling exhilarated when these highs hit. It’s a great feeling no matter what year of business you are in.
Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.
Cassandra D’Alessio: I was running a Facebook Ad Campaign for a client. We were spending about 5,000 dollars/month on ads and that amount was being charged to the client’s credit card. I had made a very small error and did not check one box when setting up the ad, despite having set up hundreds of Facebook Ads before. The result was over 20,000 dollars being charged to the client’s credit card in about two days. When I realized my mistake, I knew that, no matter what, I was going to pay back this client for the error on my part, and in doing so, could bankrupt my company.
Based on your experience can you tell us what you did to bounce back?
Cassandra D’Alessio: I got more help. I was mostly a team of one at that point, and I realized that I had so many things to focus on, I was clearly not able to give everything my full attention, even though up to that point I thought I was doing a pretty good job of it. I began to bring on strategic hires who would help me with other, larger projects (including those projects that I loved doing) so that my focus improved.
Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.
Cassandra D’Alessio:
1. A Support Network
Success is not an island. Make sure you have people around you who will be there when you’re going through the lows and celebrate with you when you are reaching the highs. They can be other entrepreneurs, close friends, and significant others. You need the right people on your team no matter what.
2. A Gratitude List
I know this may sound touchy-feely to some people, so call it whatever you want, but making a regular list of the things you are grateful for in your life is key to keep you from getting too low as well as keeping you grounded when you hit major highs. It can be as simple as being grateful for a sunny day, or your dog, or even a show on Netflix that has provided an escape from work for a few hours.
3. Celebrate the Milestones
As I mentioned earlier, celebrating your milestones is key. It’s important to adequately recognize the amazing accomplishments you have so that when a bad day hits, you can weather it better knowing good days are ahead.
4. Remain Inspired
Any successful person you admire, famous or not, has had some rough days and likely some big failures. I always think of Ariana Huffington when it comes to failure. Most of us know her best for creating The Huffington Post. When I was doing research for my book I learned that launching this business was actually born from her failed political run in California. Through that process, she had learned a lot about digital information and communication and decided to use that knowledge for her next pivot.
Keep these stories close. Read or listen to an autobiography, watch a documentary or just scroll for inspirational quotes on Instagram around people that have inspired you.
5. Pivot
It’s not surprising I use Huffington’s example since pivoting from failure is one of the most important parts of being a successful entrepreneur. What can I learn from this? How can I do better? I quote this in my book, but I stole it from the military: “Adapt and overcome.” Whether you are riding a high or a low in business, you need to adapt to the situation and move forward. Remaining stagnant will be the death of your business.
We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?
Cassandra D’Alessio: For me, resilience is the ability to adjust, which is something all great entrepreneurs can do. We pivot, adapt, whatever you want to call it. People who are successful at business, and in life, definitely feel down when they’ve had a bad day, and celebrate when they have a great day, but they don’t let those days (good or bad) define them. They continue adjusting, looking forward, and tackling new horizons.
Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?
Cassandra D’Alessio: Around the time I turned 30, I was going through a difficult divorce, my contract at a major University had not been renewed, and I had been evicted from my apartment due to new commercial construction being built on the land. In the span of about four months, I was on completely unsteady ground: financially, physically, and emotionally. Building the grit to get through that tough year, has been huge in my success as an entrepreneur. You don’t always know where the money is going to come from, or what your next step is, but you still have to keep moving forward.
In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?
Cassandra D’Alessio: When I’m facing a difficult situation, my initial reaction is definitely not positive. But I do my best to share that only with close friends or write about it in my journal. Because the feeling and belief I have deep down are positive. I know that a difficult situation is not the end of the world, because I’ve been through really tough situations before — and survived. I’m grateful to have the perspective of, “Yes, this sucks right now. But I’ve been through something like this before and I’m still standing.”
Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.
Cassandra D’Alessio: I think it’s more than a positive attitude, but a genuine attitude. I’ve been around leaders who never showed any attitude but a positive one, and that wasn’t realistic or relatable. If a situation is difficult or a client is being especially tough, I don’t pretend that it’s not and hopefully give my team the space to have any feelings of frustration, which is normal and healthy. Then, we can work on moving towards a solution and we can all feel genuinely positive about that.
Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?
Cassandra D’Alessio: It’s not a groundbreaking quote, but it was one my grandma said all the time, “Just take it day by day, Cassandra, that’s all we can do.” She would say that to me, no matter what was going in our lives, even if it was just a dreary rainy day. It’s one day, and we’ll tackle this one before we can think about the next. It’s true of any difficult time during your life, and it’s especially true of being an entrepreneur. For me, it keeps everything in perspective.
How can our readers further follow you online?
Cassandra D’Alessio: Readers are welcome to connect with me on LinkedIn: cassandra-dalessio at or follow my business, Next Page Brand Strategies, on Facebook and Instagram at @NextPageBrand.
My book, “This Won’t Be Pretty,” is available for purchase (hard copy and e-book) on Amazon.
This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!
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