Ivan De Irish


Growing up under less-than-ideal circumstances in the inner city of Bridgeport, Connecticut, Ivan De Irish felt he had few options for his future, but, through watching his parents work hard every day, he learned the value of discipline and integrity. When it came to himself, however, he didn’t always have confidence that he could make his way in the world and become successful. Thankfully, his family knew better.

It was their encouragement that led Ivan to Temple University, where he earned a bachelor’s degree in liberal arts. Ivan then attended George Washington University, completing a master’s in professional studies. It was here that he took a class which showed him how to start a business. This class would change Ivan’s life in ways he never imagined. In the years since, he has created multiple businesses, including Legacy Consulting Group, an organization designed to help athletes build generational wealth. Ivan De Irish has also recently completed work on a new book called Outside the Box, which is meant to serve as a reference tool for young people seeking advice on career development.

Throughout his career, Ivan De Irish has met many successful people who provided him with inspiration. Seeing how they made a difference taught him that he, too, could be a catalyst for positive change, and this compulsion to give back to his community has fueled the pursuit of his passions. Now a sports agent, consultant, author and philanthropist, he enjoys sharing his journey with clients and students alike. Ivan’s next big project is filming a documentary on Nelson Mandela, which includes a trip to South Africa where he will visit the home village of the legendary boxer, civil rights leader, and president.

Where did the idea for your career come from?

The idea for the Legacy came from working with so many athletes that were earning significant wealth but were not always able to maintain it. These athletes and entertainers are leaders in their communities. Many of them participate in philanthropic activities. I could see a real need for them to be educated on better spending habits and better investments. If they can learn to manage funds better, they are able to leave a legacy for their families and their communities. I name this business based on the mindset that I want these clients or students to adopt in order enhance their wealth through better choices. As for Outside the Box, thinking outside the box has brought me great success, and I wanted to encourage others to do the same. Not everyone takes the same path. The more information you have, the better prepared you will be to make good choices.

What does your typical day look like and how do you make it productive?

I wake up early and take some time each morning to plan out the day. Once I get going, my days are full of meetings. I meet with current clients, potential new clients, as well as colleagues. There are plenty of phone calls, too. Travel is necessary in my position. Depending on who we work with, I might fly out to a sporting event or concert to meet with a client. No two days are the same, which I love. I’m lucky to be surrounded by great people with great vision. They all believe in integrity and transparency, which is the best possible foundation on which to conduct business.

How do you bring ideas to life?

When an idea hits me, the first thing I like to do is envision how I can make it become reality. Most recently, I’ve been working on a documentary about the life of Nelson Mandela. He was such a great leader and a huge influence on me. Right now, we’re making arrangements for me to travel to his home village. I plan to document my visit. This project started out as just an idea that I took to my partners. We took some time and brainstormed how to bring it to life. That’s an example of why it’s so important to surround yourself with people who share your vision. Preferably, they will also have strengths in areas that you lack. I find this has been the best way to bring ideas into reality.

What’s one trend that excites you?

Trends tend to pass me by. I just don’t follow them too much. In my personal life, I guess I would have to say my favorite trend is being with my family. I love the holidays because it gives me time to rest and reconnect with the people who have made the most lasting impact on my life. I cherish those times. If it wasn’t for my family, I would have never realized what I am capable of. It was their love, support, and insistence on my pursuit of higher education that helped me in life the most. Taking time to spend with them is one of my favorite things to do.

What is one habit of yours that makes you more productive as an entrepreneur?

When I envision something a certain way, I will not stop working until it is finished exactly how I originally pictured it. I am a perfectionist. Things have to meet or exceed my expectations. Entrepreneurs depend a lot on word of mouth, so if you are sub-par or accept things that are less than high quality, that will inevitably become known. As for myself, I prefer to be known as someone who will go above and beyond. Persistence and discipline are important habits. As is working hard to set the proper expectations for your team and maintaining that same level of discipline throughout your career.

What advice would you give your younger self?

If I could go back and tell my younger self to think outside the box sooner in life, it would have made such a big and positive difference. It took many years and many learning experiences to get to a point where thinking outside the box became my de facto state. When I was young, I did a lot of following. I had to learn how to be a leader, to trust my skills and knowledge. Patience is another skill I wish I had when I was starting out. So, I would also tell my younger self to be patient and stay the course, and that things will work out if you cultivate discipline.

Tell us something that’s true that almost nobody agrees with you on.

I believe that Nelson Mandela was the greatest political leader worldwide in recent decades, even more so than Martin Luther King, Jr. or Malcolm X. There was so much unrest in South Africa in his time. Apartheid was a horrific situation and he knew it and stood his ground, even though he was prosecuted and thrown in prison for that belief. He spent 27 years in jail, all totaled. But his stance was so strong. He believed in ending Apartheid so much that he sacrificed much of his own life and time with his family to show the world how wrong it was. Imagine having that much strength in such a difficult atmosphere, with so much hatred and racism surrounding your everyday life. He is truly an inspiration to me.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Discipline and hard work are the two most important factors to my success. Nothing that is worth achieving comes easy. You have to be willing to work hard through the good days and the bad days. Not everything works out exactly as you want it to. It’s how you learn from those moments that will determine your success. Stay productive and always work with integrity. It doesn’t matter what business you’re in, integrity is everything.

What is one strategy that has helped you grow your business?

Consistency. It goes hand in hand with discipline, really. You’re going to have ups and downs, wins and losses. Being consistent and working with integrity will keep you relevant. Clients have to trust that you will keep your word and deliver on your promises. That is done through doing good, solid work over and over again, without exception.

What is one failure you had as an entrepreneur, and how did you overcome it?

When I first started experiencing success, greed became an unfortunate part of my approach. I quickly learned that is not the right way to think about things. That realization helped to keep me on the right path. It’s one thing to want success, but it’s quite another to want it so badly that you don’t make the best choices. This is why I have such an intense focus on working with discipline and integrity. Again, it’s how you react to adverse outcomes that will determine your success. Learning how to manage yourself and keeping your word is key. Without that, you will flounder.

What is one business idea that you’re willing to give away to our readers?

For entrepreneurs, sometimes ideas come to you when you least expect them. Whatever you are passionate about, just find a way to build a business around it and get it out there. Educate yourself as much as you can on all subjects relating to whatever idea you have. Learn what you can about it and how it can help others. Determine your weaknesses, and then work to mitigate them. I often recommend that people pursue multiple businesses if they have multiple good ideas. You can always compare the ideas after some time has passed to see which is doing better, and then favor that one over the other. But my larger point is that you definitely won’t succeed if you’re too scared to try anything.

What is the best $100 you recently spent? What and why?

I purchased some wireless microphones for the upcoming documentary. They are high-end because I want the world to really be able to hear the voices of the people in Nelson Mandela’s village. It’s so important to me that this project becomes an educational tool for the world.

What is one piece of software or a web service that helps you be productive?

My calendar is the most important tool that I use on a daily basis. It keeps me on track for both personal and business-related events. My meetings are stored there. Important deadlines all have their own alerts so I can be reminded to review things when needed. My life can be pretty hectic at times, so having something so handy is extremely useful.

What is the one book that you recommend our community should read and why?

Native Son by Richard Wright. This book touched me because there were many parallels between my youth and the struggle of the protagonist. He had many temptations throughout his life. Growing up in the inner city, sometimes young people are encouraged to make the wrong choices. My life could have easily gone in another direction if my family didn’t push me to do better. It’s an excellent book that I think anyone can learn something from.

What is your favorite quote?

“The definition of insanity is doing the same thing over and over again and expecting different results.” That quote is often attributed to Albert Einstein, but I’m not sure if there’s any concrete evidence that he ever actually said it. Regardless, I think the sentiment contains great wisdom, and is applicable to many aspects of life.

Key Learnings:

  • Integrity is everything.
  • Be disciplined.
  • Surround yourself with excellent minds.
  • Be willing to put in the hard work.