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5 Major Lessons Learned When Stepping into Becoming an Entrepreneur

No business book can ever prepare you for the feeling of quitting your job to start a business for the first time. On one hand, the most exciting thing you can ever do to build something of your own. On the other hand, you no longer have the stability of a regular paycheck, and it takes a lot longer than most people realize to get a business off the ground.


In the spirit of self-improvement, Kevin Palmieri and I recently had a discussion on Episode 13 of Determined AF podcast about our experiences as new entrepreneurs. In particular, what contributed to our successes and what we would do differently, knowing what we do now. Here are the tips we have for new entrepreneurs to help them to accomplish more in the first five years of starting a new business.

Find Alignment  

When what you are doing is in alignment with your values, beliefs, and the person you want to be, your work becomes fulfilling. It becomes easier to keep going without the profit and accolades because you are proud of the work you are doing.


A lack of alignment creates friction. If you look back on the times you felt you were frequently pivoting or just head down in full work mode, you’ll probably find that those times may not be in true alignment with your values and goals. This is why it is so important to create alignment in your business. Not only does it make the work you do more enjoyable, but it also creates an optimized work environment. Kevin was the happiest he had ever been, even when he didn’t know how he was going to pay his bills because he was proud of the man he was becoming. He felt like he was doing something that mattered.

“If you find something you really feel pulled to, and it fills you up. If you feel like you’re growing and contributing towards something greater, then ride that train for as long as you can." – Kevin Palmieri 

Personally, I hate the saying, “if you love what you do, you’ll never work a day in your life.” It sounds great, but it’s not how things work. As entrepreneurs, we should dive into what our values are and what brings us joy because then we can find our personal definition of success. Once we have that, we can create alignment in our personal life and business by working with our values rather than against them.


Finding that alignment starts with awareness. Sit down and draw 2 lines on a piece of paper. One column is core values, one is core beliefs, and one is core aspirations. The easiest way to fill these columns is to look back at standout memories.

  • When have you felt really proud of something you did?
  • When have you felt really ashamed of something you did?
  • What attributes or behavior do you find frustrating or enraging in others?


From these answers, you can tease out your core values, core beliefs, and core aspirations. It is helpful to remember that these values, beliefs, and aspirations can and will change as you grow. This exercise is about finding your WHY for the next year or the next few years.


This brainstorming exercise will help you to figure out who you are as a human being and what you value. Once you have that information down on paper, it is easier to be purposeful in your business planning so you can find a fulfilling balance.

Forget About What Other People Are Doing 

The best way to become demotivated is to compare yourself to other people around you. In the first few years of starting your business, you need to put the blinders on to focus on what you’re doing rather than looking to others for inspiration. It is easy to doubt yourself because you are taking longer than someone else to achieve success. It is also easy to be swayed by what other people are doing and abandon the aspirations and plans you had for your business.


This comparison only hurts you because you’re seeing someone’s external view and comparing it to your internal view. Often, especially on social media, people are showing you their highlight reels. You don’t see the sleepless nights, the months living on ramen, and the multiple times they failed before they found their winning formula. This is also why I am so passionate about transparency because the loudest voices are often people claiming that entrepreneurship is easy and they made huge profits within the first month of starting their business. That is not realistic for most new entrepreneurs.


In addition to that, you have no way of knowing what another entrepreneur’s life is like. In the last two years, I made the most money I had ever made in my life, but to achieve that, I was working 12 or 14-hour days, and in my personal life, I was going through a divorce. It took my divorce for me to really reflect on what brings me joy. I realized that I didn’t want to spend most of my time in work mode; I wanted to take more trips with my kid and find fulfillment in multiple areas of my life.

“We are hardest on ourselves for the things that others have done better, but nobody has your story. They don’t have the same realizations, challenges, or internal emotions as to how it affected them. We are all so different, and we can bring something different to the table.” – Jamie Milam

Be Consistent 

Kevin credits consistency, or staying power, as he calls it, for his success. When he partnered up with Alan Lazaros, they promised each other that they would never miss an episode. That promise kept them releasing episodes when nobody was listening to their podcast and when they were in debt.

“In the beginning, I just tried to be in as many places as I could and put myself where there was an opportunity for success, regardless of the fear.” – Kevin Palmieri

As the saying goes, time over task. The more you do a task, the more experienced you become at the task. At the start, your numbers don’t matter because you will improve the longer you do it. The question is, how long can you show up, and how long can you stay?


Alignment will be a major factor in your consistency because it is easier to keep doing something that you enjoy. Kevin records 800 – 900 podcast episodes every year, not because he has to but because he enjoys it. Those kinds of numbers would be difficult to achieve if recording podcast episodes were a chore.


Your definition of consistency may be different from Kevin’s. I certainly don’t intend to record anywhere near that number of podcast episodes. When I hear other entrepreneurs talking about numbers like that, it does create a moment of doubt as to whether I am doing enough. However, that is not an activity that would support the bigger vision I have for myself and my lifestyle. It doesn’t serve me to compare myself to Kevin because we have different values and visions.

Get Your Finances in Order Before Quitting Your Job 

From his experience of being broke and stressed while trying to work on himself and start a business, Kevin’s biggest advice to aspiring entrepreneurs is to save money before quitting your job. When he quit his job, he had no idea how long it took to start a business, let alone how long it took to gain a foothold in business. Being in better financial shape before quitting his job would’ve made the journey a lot less stressful.

“In the beginning, make sure that you’ve got your safety nets because if you’re in a situation where it’s sink or swim, I hope to goodness you’re ready to like really really really paddle.” – Jamie Milam

In the first two years, Kevin and Alan focused on their character and their aspirations for the business, sometimes to the financial detriment of their business. Kevin likes to say that they were stepping over dollar bills for the sake of being true to themselves. A financial cushion would’ve put them in a better position to do this. Alternatively, they could’ve found a better balance between making money and staying true to who they aspire to be.


My experience was similar; I also wish I had a bit more of a safety net in place when I quit my job and got started in real estate. I left a high six-figure paying position, and I was feeling the pressure to make it work after putting our family in that position. It ended up being a fire under me to do whatever it took to learn faster and fail faster, but I do wish that I had not put the wellbeing of my family on my shoulders. When you get into that hustle mode, without checking in if it's in alignment in a well-rounded way, it can have negative side effects.

Learn as Much as You Can 

Knowledge is power. The best way for entrepreneurs to shorten their learning curve is to research before starting their business. I’m a planner, and I truly believe that I was able to accomplish as much as I have because I asked around for information, set goals, and reverse-engineered my path to success.


Looking back, I’m not sure I asked the right questions. When I got started in real estate, I realized quickly that I didn’t have the local connections that other realtors had because I had been traveling for work. That is why learning is an ongoing self-improvement task. I knocked on the doors of as many veteran agents as I could. I learned as much as I could from them and asked as many questions as they would allow me to ask. I didn’t care if someone was a top seller; I wanted to learn everything I could from the people around me.


Kevin and I both agree that doing the research and asking questions is a key step for entrepreneurs. It is important to know what to expect because it often takes a long time to see results the first time you start a business, especially if you have unrealistic expectations. As Kevin says, misaligned expectations lead to misaligned strategy.


Learn more about Kevin Palmieri’s experience starting a business over on the Determined AF podcast. We talked at length about his experience during the first few years in business, especially the struggles he faced as a new entrepreneur. Today, the business he co-founded, Next Level University, teaches other entrepreneurs how to build businesses they are proud of and live fulfilling lives. Check out the full episode below!



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