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Dear Matt: A Note to Self After a Decade in Business

A letter to myself ten years ago about the ups, downs, wins and losses of entrepreneurship.

Dear Matt,

You are 26 years old. You just got back from the lawyer’s office. You are an S Corp as he advised. You don’t know what that means, but it sounds official. Your wife is pregnant. Will it be Viviana or Nicholas after your father? You just closed on your first house. Your wife is leaving her job as a schoolteacher soon. How are you going to pay for the mortgage now, genius? You are so nervous, but you are also excited about the vision and the endless opportunities that lie ahead.

Look at me, everything is going to be just fine.

The next decade will take you to places you’ve never been. You will meet people you never thought you would meet. The next decade will take you to new cities, new countries, new beginnings. People will join you from companies that you’ve never imagined. You will conceive a vision, give birth to it, and see it come to life and grow.

Your father will tell you he doesn’t agree with your decision, that you’re not ready yet. You will listen, but go against his advice. Once you make that decision he will immediately go into support mode. He will be your guiding light for the next decade. Take a lesson from this as a father yourself. This is what great parenting is all about.  

You will create something from nothing. That feeling alone will give you immense joy and gratification unlike anything I can describe to you right now.

All in the span of a decade. What a beautiful decade it will be.

Quickly, almost immediately, you will find out that business is not a straight line. It’s a curvy line with countless bumps and unpredictable turns along the way. There is no way I can prepare you for the curves, so all I can say is try to enjoy them when they come. They will be difficult to navigate, but they will also represent what makes the process fun and exhilarating. If you tackle them head on with the right spirit you will learn and improve because of the curves.

After Year 1 you will be told that 80% of people like you would have failed. You will be proud that you are one of the 20%, but you will already be on to the next challenge.

After Year 3 you will be told that 5% will successfully take the next step.

After Year 8 you will be told that 2% will successfully take the next step.

You will successfully scale through of each these steps, yet one thing will remain constant throughout the process. You will always be chasing what’s next. Breathe, relax, and take time to celebrate the achievement of beating the odds at each step rather than always chasing what’s next.  

At around Year 3 you will realize that you can’t do this alone. While that will be a difficult adjustment for you it will turn out to be the best thing that happened to you in your career. You will soon find that the contributions of others are more important than your own.

You are not one to adapt well to partners, but in time you will find some special ones. Once you find them hold onto them. You will see the immense value they bring. You will be amazed at the pride and enjoyment you will get when you find the right co-pilots to take flight with. You will become a better leader and a better man because of them.

There will be so many people that support you along the journey. Stay loyal and give back.  

There will be doubters along the way. Surround yourself with positive people and eternal optimism, but never forget the doubters. They will be more important to your success than the believers. Kill them silently through innovation, work ethic and constant self-reflection.

At times you will be told you are too young. At times you will be told you are too old. At times you will be told you are too small. At times you will be told you are too big. Have respect for everyone’s opinion, but never carry an inferiority complex. Don’t let negativity breed paranoia or insecurity. Don’t let anyone tell you that you don’t belong.

You will soon find out that results will be the great equalizer. Turn to results to even the playing field no matter what handicap you’re playing with. You will learn that age, financial resources and experience are nothing more than built-in excuses that will distract you from reaching your goals.

Investors will come calling. Some calls will be tempting. Stay true to who you are. Recognize your weaknesses. You are a grinder, nothing has ever come easy. What made you think business would be any different? Say no and trust that in the end it will all be worth it.

Your stubbornness will be a roadblock at times. Be accountable, look in the mirror, listen to others around you. Their perspectives will help you see through your blind spots.

At times you will feel you are becoming too hard. At times you will feel you are becoming too soft. Chances are both are true. Make adjustments. Pivoting will be a beautiful thing. You will be surprised how much satisfaction you get from self-improvement.

Your perspective on money will change dramatically. Over the next decade you will accumulate more money than your parents did in their lifetime. Yet you will still be just as worried about finances as you were when you were paying $850 to rent an apartment in Brooklyn. That should tell you something. Yes money will always drive you, but soon you will learn that the most valuable currency you can transact in is impact and improvement, not cash.

At around Year 7 you will realize that your most gratifying moments come not in the most profitable of months, but by watching the growth and emergence of others around you. 

For whatever reason life will be good to you, Matt. You will welcome three beautiful girls into the world. You will have a wonderful wife. All of the people you love the most will be blessed with great health and no life changing events.

Matt, please go easy on those who love you the most. Your mother’s courage, your father’s pragmatism and your wife’s class will lay the foundation for any modicum of success you achieve in the next decade. Thank them, love them, and most importantly go easy on them even in the most stressful of times. You will see people close to you lose their loved ones. Let that serve as a sign. You don’t know how long you’ll have them for.

Your grandmother, god bless her, will still be with you. She will be with you physically, but not mentally. This will destroy you inside. You will be forced to take consolation in knowing that somewhere inside, your grandmother – you know the one with the fifth grade education who speaks broken English – somewhere inside she is proud of what you have achieved, and she feels a sense of fulfillment for making the sacrifices she made for you and your mother. You will visit her on weekends, except it will be in a nursing home. Not exactly how you envisioned sharing these moments, but it will have to do. Drive by her old house from time to time, you know the one on North 6th that you named your company after. It will be a safe haven for you and it will help you find strength and happiness in your most difficult of moments, just like it did when you were a child.

You will be exposed to others in business who build great companies and then see it all come crashing down in the blink of an eye. Let those be warning signs. Never get complacent. Stay humble. There are no guarantees. 

Remember back to the times when you were a child competing on the ball field. Even though you are older now and the stakes are different, the emotions remain the same. Smile and celebrate the winning moments. You will get joy from them just like you did when you were an eight year old in the schoolyard. Learn from the losing moments. They will burn just like they did when you were a kid. There will be plenty of them.

You will build a network of people who are much smarter and more intuitive than you. Thanks to them you will hear about many new trends. Opportunities will present themselves to you before most others hear about them. Big data, artificial intelligence, blockchain, crypto currencies, beacons, cannabis, virtual reality. Don’t look so puzzled. Soon enough you will know what all of these mean. Don’t be afraid to roll the dice on a few of these, but be smart. Don’t bite off more than you can chew.

You soon will see where your true passion lies. Building teams and bringing people together. You will make so many mistakes along the way, but in the end you will figure it out. You will assemble an incredible team. Treat them as if they are family. 

Your fire and drive will fuel you. It will be your greatest asset, but also your greatest weakness. You will never be satisfied. You will never feel you are going fast enough. You will never feel like you’ve arrived. These can be championship traits, but also unhealthy ones at the same time. Please try to slow down sometimes and enjoy the moments. There will be a lot to smile about.

You will sit here after a decade has passed and you will be as energized for the next challenge as you were for the first one. Because of your blood, sweat and tears you now have a destination within reach. Take all of the lessons from the first decade and apply them. Go get it.

As always remember there are no guarantees. But please Matt, enjoy it more this time around. If the first decade is any indication, I think you’re going to be just fine.

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