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Jason Mezrahi of Win Daily: “Take care of your health”

Take care of your health: The steady grind of being an entrepreneur can take a toll on your health and your lifestyle, so if you plan out time to work out, eat well, and get your sleep, you won’t pay for it later. In the first two years, I sacrificed a lot of nights and […]

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Take care of your health: The steady grind of being an entrepreneur can take a toll on your health and your lifestyle, so if you plan out time to work out, eat well, and get your sleep, you won’t pay for it later. In the first two years, I sacrificed a lot of nights and missed workouts in order to launch the brand successfully, which in the short term, might be chalked up as a win. But you can’t take your health for granted at any time.


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Jason Mezrahi.

Jason Mezrahi is an energetic, entrepreneurial, and meticulous individual with 20 years of overall entrepreneurship, leadership, sales, and marketing experience. He is the Founder and CEO of WinDailySports.com and Win Daily Inc which is one of the fastest growing companies within the Fantasy Sports and Sports Betting industry. He is the author of “Win Daily” and the host of the Win Daily Show on SiriusXM Fantasy Sports Radio.


Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

My name is Jason Mezrahi, and more than anything else in life, I am a competitor. From my early years in Queens, New York, playing pickup games of everything after school, to the world of big business and high-stakes gambling, to the subtler chaos of Daily Fantasy Sports, I always have, and always will, love the thrill of competition. Although my days of diving for loose balls in my high school gymnasium have passed, the same mentality has served me well in each of the various endeavors I have taken on in the years since. Every day, I demand a victory of myself, and I do everything in my power to claim that victory, regardless of how grim the circumstances may appear. The day’s victory is always in there somewhere. It is up to us to find it, take it, and apply it as we move ahead in our lives.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

The catalyst was a simple message from my wife, who randomly told me one day that I should write a book about my life as a professional gambler and a daily fantasy sports player. When she told me, I simply looked at her and laughed. Then, I went on to say: “Why the hell should I, of all people, write a book? I hate to write, and I have no passion for the spotlight.” I brushed it off, until about a week later, when a second person randomly hit me with the same message. At that point, I took it as a sign that I needed to move forward, trust the universe, and step out of my comfort zone. It has been said that your greatest accomplishments in life occur when you step out of your comfort zone. After the transition I made a couple years ago, it is a message that I share with everyone with whom I come into contact.

There is no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

After having a lot of “great” ideas over the years, I realized that ideas are only as good as the execution of the actual idea. If you have a great idea, but can’t execute upon it, for the most part, it becomes worthless. On top of that, as I matured in life, I realized that in order to truly launch an idea into a business, you need to have a passion that is unmatched, so that when the obstacles occur, you will have the energy and drive to surpass them. I wake up every day and don’t view my business as a job or work. I view it as journey and a destination to greater success. Along the same lines, the real asset to your business is not the product or idea itself, but it is the team and support with which you surround yourself. Without the team I created at WinDailySports.com, I would have never accomplished the results that we have in the past two years on my own. The focus of any startup should be on building your team, culture, community and brand identity before you ever factor in revenue and profits.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

First off, you need to be realistic and do your research to see if it’s truly feasible to build a business that will support your lifestyle. Creating a business to support your hobby, which leads into debt ultimately won’t make you happy. However, at the same time, if you can earn a living and support yourself financially, while taking a decrease in salary — the increase in happiness can go a long way in the pursuit of a balanced lifestyle. I suggest that you take stock of what truly makes you happy about the work you do. For example, I always wanted to work in sports, but at the same time, I never wanted to be in a position of making small financial gains with slow upward mobility, which can be the case when one is trying to build a career in sports.

With all of that being said, if there was ever a time to dabble and start laying the seed in building a business about which you are passionate, the time is now. Before I made the leap and started my own business, I worked my nine-to-five job. As soon as I came home, I spent another six to eight hours daily building out the plans and infrastructure for my startup. There is enough time in the day to work your day job and build your business once you get home. So, cut out the television, social media, and make the most of your time.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I have a passion for business and I find my fun in building, innovating and seeing my vision come to life. Don’t get me wrong, it is a daily grind. Don’t think that on half of the days, I don’t question myself and ask: “Why am I torturing myself running a business that never stops and that I have to manage 24/7/365?” Trust me, there will be more tough days than celebrations, but I wouldn’t have it any other way. Again, it’s all about having a great team around you and a fun community with which to engage.

At WinDailySports.com one of our best products is our “Expert Chat,” which is chat room filled with thousands of Win Daily subscribers. I spend more time in this chat than I spend talking to my family on most days. We have members from all over the world who are sports enthusiasts that are all working together to help each other win, and it’s truly a community like no other. During the pandemic, it’s been a safe haven and an outlet for all of us to stay connected with each other, keep all of our minds on the positives in life — and without it, I myself, would have truly been bored.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

It’s all about my team at Win Daily. I have built a team that I consider to be a family — a group of passionate sports enthusiasts who love playing daily fantasy sports, placing bets, producing content, and above all, being good people and helping others. Our family is tight, and even though most of us live in different states and countries, we talk to each other daily and act as if we have known each other all of our lives. Having that culture as a company is so important, and to create it without ever meeting each other in person, nor showing up to an office daily, can be hard. However, I make it a point to have a personal relationship with every single member of our team.

The downside of the business is the fact that every day, someone in our community faces defeat. Losing is a tough pill to swallow, especially when there is money involved. So, you can imagine that when a subscriber loses a lot of the time, they point fingers at one of our writers for a bad pick, or are just angry at themselves and acting negative in our chat. We have policies in place and 20+ staff members who are always available to help struggling players out, and we make sure to put in the extra effort and provide some one-on-one coaching in order to break a losing streak and figure out what the caused the problem. In most cases, the problems get resolved almost instantaneously by our staff. There is nothing I like to see more than another subscriber sticking up for the brand and stepping in, without it even being their responsibility.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

I have been in this seat before, and I have run several businesses from ownership and leadership positions in the past. So, I knew what I was getting myself into this time around. In all honesty, the biggest difference is that the tasks that I never had any ambition nor dreams to do, which I took on because they were a must for the business to grow, were actually more enjoyable than I would have thought.

For example, if I saw an ad for a SiriusXM radio host for the Fantasy Sports channel appear in a job listing, I would never have gone out of my way to apply for it five years ago. But, now it’s one of my favorite roles in the company. Being able to host the Win Daily Show every Saturday and Sunday is the highlight of my week, and I hope to do it for as long as possible. The energy that I feel from being on that mic is truly a victory in itself.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so, how did you overcome it?

The competition in this space is very intense. Over the past two years, I have had several of my closest employees get poached by other companies. The other companies, at that time, were in a position to offer higher salaries since they were heavily funded, whereas I was bankrolling my entire company from my personal savings. Two of my closest friends in the industry, who worked at my company, decided that they couldn’t pass up on the money — and they chose short term gains over the loyalty to my brand and the long-term vision I had in my mind. It truly hurt, because above all, I value loyal friends and staff who I know have my back. Money comes and goes, but real friendships — whether in business or life — should come first. I will be honest, it hurt, and it was blow that took me about a week from which to recover, but I wouldn’t have it any other way. The move they made to leave turned on a light switch for me to go bigger and better — and I haven’t looked back. Our team is stronger now more than ever, and the exponential growth we have seen since that day, even during the pandemic, made me stronger as a leader. It also makes me believe even more that Win Daily will continue to grow every day, no matter what.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I first started to build the website WinDailySports.com I was told by many that I had to start a podcast and that everyone else in the industry was doing it. So, I agreed to follow the trend and began looking for a co-host to run the show, and with whom I could share some of the responsibilities. So, I have to admit, I was a rookie and desperate to find someone else to fill in the time slots because I was leading another business. After putting together a skeleton crew of podcasters, we started our first couple of shows and hit the ground running. I gave the lead daily host spot to the individual who had the most experience and who had been on television and radio previously.

He talked the biggest game and had this whole concept of how to run the show. With my management style, I truly don’t like to limit people and I give everyone an opportunity to shine, so I passed the torch and hoped for the best. But, this individual turned out to be “out of his mind” when it came to his approach and style. The intro he would give himself, combined with the funky voices and nicknames he had, was hilarious, as I think back on it. The lesson here is: never make desperate moves when you are not prepared to take on the responsibility — and always do a trial run!

Who has inspired or continues to inspire you to be a great leader? Why?

I read a ton of books and listen to as many podcasts as I can. From Napoleon Hill, Gary Vee, Grant Cardone, Tim Ferris, and David Meltzer — the list can go on for another paragraph! I consume as much content as I possibly can squeeze into my schedule. I try to soak up as much knowledge from the leaders of industry as I can to prevent myself from paying the “dummy tax.” At the same time, I have made some personal connections to some great leaders and mentors. Networking is so crucial as an entrepreneur, and I have been lucky enough to have David Meltzer, co-founder of Sports 1 Marketing become a business coach for me on the sidelines. I can rely on him when I have a tough question that I need answered.

As far as inspiration goes, the birth of my first child occurred while I launched Win Daily, and she gives me the inspiration to stay focused and keep my eye on the prize. I want her to be proud of her dad when she is old enough to realize what it is that I am always working on. I am inspired to build the brand to the point where I will be able to have the freedom to spend more time with her, and coach her to the successes that she wants to achieve in life.

How have you used your success to make the world a better place?

I have used my success to make the world a better place — but not to the extent that I envision when all my plans and goals have been accomplished. There is still a lot left to achieve, but we are off to a good start. As I am writing this, an NBA fantasy contest has just finished around 12:45 a.m. on a Thursday night and the messages in our expert chat are violently ringing off the hook with subscribers cheering and thanking our staff. For a lot of the new subscribers to Win Daily, they are coming from a history of repetitive losing. The learning curve in this industry is harsh and there can be weeks and months of consistent losses and loneliness.

What we have given to the community is an education and a real opportunity to “Change Their Game and Change Their Life.” Since I started the brand, we have had multiple six-figure wins within our community and countless five-figure wins, which are truly life-changing events. I remember the feeling the first time I woke up my wife in the middle of the night when I had won 155,555 dollars in an MLB fantasy contest, and my life has never been the same since. On top of that, I believe the book I authored Win Daily: How to Win at Fantasy Sports & the Game of Life has truly been a positive force in the industry. Many of the principles I share in the book, with my team, and within our community bring a positive, winning mindset to people’s lives.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. Get proper funding from the start: I started the brand from personal savings and I chose to keep the company lean and scale it only when the time was right. If I had had the chance to hit the reset button, I would have probably secured proper funding in order to scale faster.

2. Find a strong developer right away: Running a tech company relies upon having a great developer or two by your side. With my skillset being leadership, marketing, and sales, having a great CTO (Chief Technology Officer) on our team from the start would have saved me a ton of headaches and mistakes. Third time’s a charm, — luckily after having two failed coders, I finally found the right man to do the job.

3. Quit your day job and go all in: For the first year of operating the business, I worked a full-time job while starting Win Daily. Having a family and a newborn, it was the safe and secure thing to do, in some aspects. However, my loyalty to my job and the organization I worked for prevented the potential growth I could have seen in my own business in the early days.

4. Go bigger: Sometimes I am reserved with the goals of the business and my to-do lists, but after the first year I realized that my vision wasn’t big enough and that I had to “10X” the plan.

5. Take care of your health: The steady grind of being an entrepreneur can take a toll on your health and your lifestyle, so if you plan out time to work out, eat well, and get your sleep, you won’t pay for it later. In the first two years, I sacrificed a lot of nights and missed workouts in order to launch the brand successfully, which in the short term, might be chalked up as a win. But you can’t take your health for granted at any time.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

Adapting a Win Daily mindset. What I consider a Win Daily mindset is a thought process to always see a positive in every situation with which you get faced. Along the same lines, use a mindset in which every day you find a way to have a victory. A victory doesn’t have to be monetary or beating the competition — it could be a simple conversation with a friend or a loved one. Living your life day by day and stacking up these small victories could lead to a life filled with wins for everyone. A positive mindset can go a long way in business, life, and your relationships.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I mentioned it above but I will say it again, in case anyone missed it. “Your biggest accomplishments in life occur when you step out of your comfort zone.” Coming from a person who hated writing papers and speaking in front of people, to becoming an author and a host of global radio show on the other side of fear — it can happen if you just break out of your mold and take the restrictions out of your mind. Say ‘yes’ to opportunities, don’t worry what other people think, and take calculated risks to bring you closer to your dreams and goals.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Growing up a die-hard Mets fan, living in New York all my life, this answer might surprise most people, but I would have to say Derek Jeter. It’s actually surprising to myself as I am writing this. Baseball was my first love and I grew up playing shortstop at a pretty high level myself. Derek Jeter wasn’t the star I had posted on the wall, nor the one I cheered on every night as a Mets fan. But watching the trajectory of many athletes on and off the field during my time, Derek was one of the very few athletes that played at the highest of levels, yet who never had a blemish on his resume.

He always said the right things when the media was around, signed autographs for all the kids (me included, one day at Yankee Stadium), is a Hall of Famer and world champion, and now has continued his competitive career launching businesses and becoming an owner of the Miami Marlins. If I had my choice of having the same career of anyone, that’s the man I would choose. To be a star athlete of the game I love, and to retire as an owner of a ball club, is a goal very few could ever achieve. So, I would love to one day sit down with Derek and see what I could learn from one of the greatest that ever played the game of life.

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