John Caserta: “You need to commit to the daily activities that will get you the results you want”

…You need to commit to the daily activities that will get you the results you want. And when you get those results, you continue to stay committed to those activities that got you there and avoid the temptation to sit on your laurels. I think one of the worst things that can happen to a […]

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…You need to commit to the daily activities that will get you the results you want. And when you get those results, you continue to stay committed to those activities that got you there and avoid the temptation to sit on your laurels. I think one of the worst things that can happen to a young entrepreneur is getting “elephantitis” — it’s a condition that sets in typically after the acquisition of a large client — or an elephant — with a little-to-no effort that lulls an entrepreneur into thinking that A) client acquisition is easy and B) there’s no need to bother with smaller clients. I’ve seen it happen so many times and I believe it’s the primary reason for the “ups and downs” for an entrepreneur. By simply staying committed to the daily activities that lead to client acquisition, you can “smooth” out the ride and develop a more consistent flow of business.

Being a founder, entrepreneur, or 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 John Caserta.

John is a leading Chartered Financial Consultant (ChFC®) and highly sought-after expert on personal finances with a passion for educating people about all-things-money. In addition to regularly appearing on Good Morning Connecticut, John has been featured in and authored articles in numerous publications including the Wall Street Journal, US News & World Report, Business Insider, and Advisors Magazine. He has traveled throughout the country educating thousands on how to take control of their personal finances and has spoken at numerous universities including Yale, Sacred Heart, Uconn, Vassar, and Ohio State.

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?

I’m the youngest of three sons born to immigrant parents who moved to the United States from Italy in the late 1960s. My parents found work in factories in the New Haven, CT-area — my father a sheet metal work and my mother a seamstress. At one point, my father worked two jobs while my mother took time to stay at home raising me and my brothers. And once we were all in school, she returned to work. The sacrifices they made — leaving family and friends behind in Italy and working long days in factories to care for their children — were apparent from an early age. That sacrifice, determination, and discipline were the foundation of an unwavering work ethic that they instilled in me and my brothers that inspired us to always be our best at whatever we did.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

For me, there was no “a-ha” moment per se. Instead, when I spoke to people about their experience with “financial advisors”, the message was clear and consistent — no one was getting the comprehensive advice they really needed. In fact, what most people described as a “financial advisor” amounted to nothing more than an insurance agent or investment broker. And not surprisingly, any problem they had was solved with an insurance policy or investment product leaving the client on their own to coordinate all the other facets of their finances. If anything, the concept of a team of professionals working in concert in various areas of planning — taxes, insurance, legal, etc. — was reserved for the ultra-high net worth individuals who would hire their own “family office”.

My idea was to bring the family office to the masses. While conversations about insurances, investments, and other financial strategies were important, so too were conversations about goals, family, and life. With our technical knowledge and expertise, I knew my clients could realize their vision of success.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

Looking back at my life, the signs were always there that I wanted to build something. I was in 3rd grade (maybe 4th) and I distinctly remember making a Christmas decoration in school. It was a Santa Claus made from construction paper — the limbs were attached with brass fasteners so they could move in different directions. When we were told to put our names on the back, I wrote “Caserta Enterprises” on it. I may have even added an “Inc.” in there for good measure. Looking back at that moment, I chuckle and think to myself, “What 10-year-old does that?”

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?

My family. Without the support and encouragement of my parents or my brothers — especially when things were tough — I would be nowhere. When I first started out, I faced many challenges not least of which was the constant rejection. Getting potential clients to trust you with their money is a challenge. And it’s even more challenging when you’re 26, just starting out, with relatively no experience. I wondered if was doing the right thing and questioned whether I should keep going. When the self-doubt crept in, they were the voices to say, “Keep going — you got this!” And they helped keep everything in perspective.

What do you think makes your company stand out? Can you share a story?

Our people. With the right combination of skill and commitment, anyone can master the technical knowledge needed to be a financial advisor. But without the right people on our team, that knowledge would be useless. And when it comes to working with our clients, we not only become stewards of their money, but we become advocates for them and their families. There are so many examples of how people on our team have gone above and beyond to help our clients, from hand-delivering paperwork to coordinating appointments with other professionals. But by far one of my favorite stories was when Holly, our investment specialist, took time after work to drive an elderly woman to her hairstylist appointment after she had mistakenly called our office to get her hair done. Finding out that she didn’t have transportation, Holly offered to take her to her appointment. You’ll never find that on a resume. And that’s what makes our team special.

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?

I’m organized. Whether it’s tracking performance, outlining new marketing strategies, or growing and maintaining our client base, there’s an organized process for it. And those processes are written down so that everyone on the team can reference them.

I’m flexible. And I think being flexible is especially important in achieving your goals. You can have a plan in mind of where you want to end up. But as you go along, you have to continuously evaluate your progress and adapt to change. Years before the onset of the Covid pandemic, we began to implement systems to help up work remotely, including using Zoom and moving all our systems to the cloud. The idea was to be able to continue working in the event of a catastrophic event. Of course, no one could’ve imagined that a catastrophic event would be a global pandemic.

I’m focused. All too often I have seen entrepreneurs lose focus of their long-term goals because of short-term distractions. And some of those distractions can seem insurmountable, like the current global pandemic. But being flexible, innovative, and ultimately focused on the long-term goal can help you overcome obstacles.

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?

Like any entrepreneur, I would say I’ve had missteps along the way whether they were self-created or the result of advice that I probably should never have taken. But even advice that led me down the wrong path was critical for me in getting to where I am now. And in retrospect, I’m thankful for it.

Early on in my career, as a “solopreneur”, I had some success. I was advised that to multiply that success, I should grow my sales team. And so I did. I started to recruit new “advisors” but in retrospect, I was too green in my own processes and business structure to take on the task of managing and coaching people who were even greener. Time that was dedicated to building a clientele had been refocused on building a team. And maybe it was the excitement of seeing our headcount grow that blinded me from seeing that the wrong people were on the team. Our growth was stunted because now I was relegated to developing talent. In retrospect, I should have established the clientele first, then brought on advisors to continue working with and developing that clientele. Ultimately, I had to start from scratch and build the business from client one.

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?

First, get rid of your vacation policy. Your team is your most important asset. And the success of the business — especially in those critical early years — requires massive effort and determination from everyone on that team. It’s important that they have the time needed to take care of themselves so they can ultimately be their best at taking care of clients.

Second, listen to your team and keep the lines of communication open. As a business owner, you may know what needs to get done daily. But knowing how to do it is just as important. And the ones who will know best are the people responsible for getting it done. Give them the opportunity to tell you what’s working and what’s not — even if you’re the “what’s not”. We get together as a team on a quarterly basis and review exactly that.

And third, recognize your employees when they go above and beyond your expectations. Long gone are the days of 9-to-5. For better or for worse, everyone is connected all the time. And if you see someone replying to emails and taking care of a client issue at odd hours — like late at night or on a weekend — recognize it. A thank you is nice, lunch is good, and a bonus is great!

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry? Can you help articulate why doing that is essential today?

We live in a world where anyone can be a CEO. It’s simple — sign up for LinkedIn, type the word CEO into your “current position”, and voila`! And with that capability comes a lot of noise from a lot of different people. But ultimately, you can’t simply create or buy things like trust, credibility, or authority. You can certainly make it seem like you have those things by buying followers or sprucing up that profile on social media. But sooner or later, your lack of credibility will become apparent. One bad review can be all it takes to bring down a house of cards.

I believe trust, credibility, and authority come with time — there’s no way around it. And ultimately, I think that’s why many entrepreneurs never truly achieve it. Either they abandon that goal all together because they realize it will take too long or they’ll grind it out and do the small things on a consistent basis over a long period of time to get to where they want to be.

Take for example my speaking engagements. Early on in my career, it was common to be speaking to a room where one person showed up. And it wasn’t just once or twice — it happened a lot. And these talks were usually at night after a long day in the office. For many people, this would have been disheartening. But to me, it was one step closer to getting five, then ten, then 20 people. Just this past month, I have had numerous speaking engagements with over 60 attendees and there are many more planned this year. But all of this is after 16 years of small speaking engagements, writing articles and blogs, creating vlogs, and even picking up an industry designation and master’s degree along the way. And since days were spent developing my clientele, that meant all these “extra” things were left to evenings and weekends.

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?

Over the years, I’ve advised countless business owners and entrepreneurs at different stages in their careers. And all the mistakes I’ve seen them make (and have even made myself) boil down to two things — process and people.

Whether it’s acquiring new clients, launching a new product or service, or even keeping track of financials, having processes in place is critical to succeeding. And they can’t exist in the ether — they must be written down so that anyone joining the company knows the operations. They also must evolve over time. It’s natural that when you’re starting a business, there’s going to be a fair amount of “flying by the seat of your pants.” But getting into the habit of writing down your processes early on — and refining them over time — is essential.

And having the right people in the right seats is crucial. Early on, I heard a great piece of advice — hire slowly and fire quickly. Ignoring red flags when someone is not meeting your expectations can not only stifle your growth, but it can also be the kiss of death and bring down an entire business. Make sure that what you expect of your employees is specific and measurable. Regularly review their progress — especially early on — to make sure they’re meeting your expectations.

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”?

In my business, I love using analogies, so I’ll borrow one from my line of work to answer this question.

Being an entrepreneur is like investing in stocks while being an employee is like investing in bonds. For the most part, both will give you some growth over the long run. But the outcomes — and the journey — can be dramatically different. That’s because as an entrepreneur, I think you’re ultimately always in search of explosive personal and professional growth that can’t be met by the typical career path of an employee. And to achieve that, you must take risk! You might know exactly where you want to go, but the path you lay out may not necessarily be the one you ultimately take. In some cases, you must create paths that you didn’t even know could exist.

As an employee, there’s always a certain level of predictability — come in as an associate, earn your stripes, become a vice president, and hang on long enough to become a partner. Typically, the path is laid out for you making the journey a little smoother.

Is one better than the other? It all depends on who you ask. And in fact, some entrepreneurs were meant to be employees, while some employees were meant to be entrepreneurs.

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.

At the age of 28, I asked someone to commit 40,000 dollars per year to a strategy that I had outlined for them to help achieve their financial goal. And they did.

To me, it was asking them to entrust me with their money (and a lot of it) every year. But being newly in business, I wasn’t sure how they would react. I spent countless hours preparing my presentation making sure I knew all the details including performance metrics, tax implications, and legal aspects. And ultimately, while they appreciated the preparation, the reason they chose to do business with me was because of trust. I knew then that if I could learn everything that there was to know about my industry and engender trust from my clients, I would be unstoppable.

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.

Early on in my career, I was referred to a potential client to advise him on a 9-figure inheritance from his father. To put this in perspective, the amount this potential client had in one account was nearly the amount we advise on today after 16 years of working with hundreds of clients. Career-changing client? More like life-altering client. And having struggled in the beginning to have steady income, this client would have changed all of that and then some.

One meeting. Two meetings. Even three. It was going smoothly. He was sending statements, we were sending proposals, and we were on track to becoming his advisors. That’s when we started reaching out to the trustee at the contra firm — the company that held the funds and would ultimately release them to us as the new advisors. And it quickly became apparent that something was amiss.

The contra firm had no record of the account and no record of the client. But what was even more disturbing? They had no record of the “employee” that was communicating by email with the client. While the email address seemed to be associated with the firm, it was slightly different than their official email address. Over the years, the trustee who had been appointed to manage the account for the benefit of the client had broken that fiduciary role and defrauded him of millions and millions of dollars. The statements we were looking at were completely fabricated. And just as quickly as the opportunity had appeared, it vanished. And with it, I was back to square one. It left me dejected, exhausted, and questioning if I could continue dealing with these extreme highs and lows.

Based on your experience can you tell us what you did to bounce back?

Bouncing back wasn’t easy. And to say this was the only time I wondered if I could bounce back would be a lie. But truthfully, this one stung. And it stung a lot. But like I did every time, I took a step back and I asked myself why I was doing this. Why was I going through the pains of building a business? Why not just go get a job and not worry about my next paycheck? And ultimately, what made me bounce back every time was the fact that I wanted to be in control of my future. It was the long-term goal and knowing that I would eventually get there if I continued to do the small things daily that I needed to do. I focused on being committed to the daily activities that would give me the result I wanted, rather than simply focusing on the result.

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.

First and foremost, you must focus on the ‘why’. And if the ‘why’ is money you’re probably better off just getting a job. To get a business up and running so that it can turn a profit requires time and sacrifice. That means early mornings and late nights on weekdays and weekends. My ‘why’ was being in control of my time — I didn’t want anyone else controlling it. And that ‘why’ became apparent early on in my first job after graduating from college. About a year and a half into working with the company I had joined, my aunt in Italy passed away. Being close with her, my brothers and I naturally wanted to be there with our family. And I thought that being able to take the time off would not be an issue. But then again, I was not aware of the bereavement policy the company had, which only allowed for time off if an immediate family member passed away. The hassle I had to go through to get time off was enough to make me commit to never having to experience that again.

Second, you need to commit to the daily activities that will get you the results you want. And when you get those results, you continue to stay committed to those activities that got you there and avoid the temptation to sit on your laurels. I think one of the worst things that can happen to a young entrepreneur is getting “elephantitis” — it’s a condition that sets in typically after the acquisition of a large client — or an elephant — with a little-to-no effort that lulls an entrepreneur into thinking that A) client acquisition is easy and B) there’s no need to bother with smaller clients. I’ve seen it happen so many times and I believe it’s the primary reason for the “ups and downs” for an entrepreneur. By simply staying committed to the daily activities that lead to client acquisition, you can “smooth” out the ride and develop a more consistent flow of business.

Third, you have to be willing to take risks and become comfortable doing so. Throughout my career, I have taken many risks — some small and some big. And whether they worked out or not, there was always something to learn from the experience, especially when things didn’t go as planned. When I brought on my first employee, I struggled with many things. It was the first time I would be responsible for a fixed cost and that I would manage someone. Despite the fear, I knew that it was the only way to take the next step in my growth. It took several tries to find the person who was the right fit. But with each one, I learned more about the right way to grow my team.

Fourth, you have to keep sharpening the saw. You must learn as much as you can about your industry to get to — and stay at — the top. Personally, I’ve made continuing education a part of my business plan. Even though I have been in business for 16 years, a few years ago I completed an industry designation that required passing nine exams over a period of several years. Remember what I said about sitting on your laurels? Following the completion of that designation, I spent several years completing a master’s in financial services. Now I’m looking for that next educational goal.

And lastly, be enthusiastic. I love giving back to my alma mater and I had the opportunity many years back to participate in a career “speed dating” event. Students had the opportunity to sit with different professionals over the course of the evening and ask a variety of questions to gain insight into different professions. I’ll never forget one young lady who asked me how I knew I was in the right career. I was taken aback — deep down inside I knew I was, but I had never really articulated it. I looked at her and remember saying to her (almost) verbatim, “It’s 9 pm on a Tuesday night. And I’m here after a long day still in my suit talking to you about how much I love my business.” That enthusiasm, that passion, is key to finding something that you’ll dedicate yourself to, no matter how big the ups and downs.

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?

Resiliency is being undeterred. It’s an incredible focus on achieving success despite any challenges or setbacks along the way.

One of my favorite movie quotes comes from Ed Harris portraying Gene Kranz in Apollo 13 who says, “Failure is not an option.” I think the most important trait of a resilient person is that they don’t see failure as an option. And any failure along the way is simply another step in their path to success. Resilient people understand that to get to where they want to be, they need to learn from their missteps along the way.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

As a kid, I hated running for the sake of running. If it was part of playing sports, it was not an issue. But to put on a pair of sneakers and go running was something I never understood. That is until I stepped on a bathroom scale and saw a number that I had not seen before. It was about 50lbs over where someone my height should be. And when my doctor started talking about things like “diabetes” I knew it was time for a change. So, I tuned up my diet and started exercising, which including a nice new pair of running shoes. It had to work.

That first run was a complete disaster. I didn’t even make it one-quarter of a mile until I had to stop and catch my breath. What was I doing? There was no way I could do this. The self-doubt started to creep in and drown out the voice that would say you can do this. But I knew it had to work. And I believed that it would. And so, I kept going — a little running, a lot of walking. Eventually, one mile turned into two, and two turned into three. Soon I was running 5k races… for fun! I eventually even did a half-marathon. And with all that running, the pounds started dropping. I focused on the little victories along the way and remained focused when I hit those setbacks.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

I do. And I really credit that with learning early on that there are some things that I can control and other things I cannot. And my attitude is something I can control. Even though sometimes it might be difficult to do so. What helps me keep a positive attitude is keeping everything in perspective. One of my early mentors always reminded me of a great quote that comes in a variety of iterations: It’s never as good as it seems and it’s never as bad as it seems. To me, it meant truly understanding and accepting that there was no single client that was going to make or break my career. I was in control of that by committing to the things I needed to do on a daily basis. And I always stop to look at how far I’ve come. And what keeps me going is thinking that if I’ve made it this far, what else can I accomplish? And that’s when the wheels start turning.

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.

During the pandemic, I managed to finally accomplish one of my long-time goals — becoming a certificated private pilot. And one thing I learned is that as a pilot-in-command, you’re the one that passengers rely on in good times and in bad. Luckily, I have not had a real-life emergency. But plenty of simulated emergencies as part of my training taught me a lot about leadership. First, don’t panic. Panicking will lead to rash decisions and can ultimately lead you to overlook simple solutions. It will also rattle your passengers, which is not something you want to add to your workload. Second, stop. Assess the situation and work through the checklists that are there to help solve a problem. And third, remember you’re in control. There are a lot of tools at your disposal to get you down safely.

These are all lessons that I have incorporated into my business, especially during a time when we face new unknowns like a global pandemic. Communication with employees and clients is always important. But if you’re not doing it in a time of crisis, it can shake the confidence they have in you and rightfully so.

How can our readers further follow you online?

Social media — I’m all over it.

Instagram: @john_caserta



YouTube: Caserta & de Jongh, LLC

You can also follow my contributions to ABC-affiliate WTNH in New Haven, CT at

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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