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5 Things I Wish I Knew Before I Became An Entrepreneur

Author: Yitzi Weiner - A “Positive” Influencer (Forbes, Buzz Feed, Huffington Post, Inc)

Full Article HERE:


“The music business is not for the faint of heart. It tests people in different ways. However, every story shared from my heroes have all been the same. If you really love it, chase it. If you’re going to chase it, chase it with everything you have.” - Tim Gray

I had the pleasure of interviewing Tim Gray. Mr. Gray is CEO of Grayscale Marketing, an award winning entertainment marketing and advertising agency, President of its sister company Grayscale Entertainment, an artists management firm that provides digital marketing and strategic partnerships, board member and host of a new web series, The Golden Rules. Tim is also a Nashville Business Journal Emerging Leader Award Winner that’s been listed as People On The Move and nominated for the Music City’s 40 Under 40.


Yitzi: Thank you so much for your time. I know that you are a very busy person. Can you share your “backstory” with us?

Thank you for having me, sir. My involvement and love of music really began 36 years ago as a child. Growing up, I had no idea how the music industry worked, that you could get a music business degree, or how to make living at it. I just knew that I loved music and people.

As a child, I’d spend hours listening to my parents albums, creating my own concerts, drawing, and generally letting my imagination run wild. Eventually, around age 6 I had my first live performance at a local nursing home in my hometown; I was hooked. I knew from that point forward I wanted to be creative and be involved with music.


Yitzi: How did you get involved in music industry?

The financial crisis of the late 2000’s hit the live entertainment business hard and I needed to make a transition in my career, which lead me to Nashville.


However, before that move, back in college, I played in a few bands as well as took recording and music business courses. Afterward, I was involved with a startup event ticketing agency on the west coast and then became a concert promoter in Virginia.

Early on, I was constantly gaining experience at anything that would allow me the opportunity to move forward in my career. Over those years I had the opportunity to learn a lot.


During first few entrepreneurial years, I not only had built two entertainment companies but had shuttered one and sold the other. Over that time I gained extensive knowledge in business, marketing, live event photography, concert booking, event management, label relations, advertising, media buying and branding which all helped to develop my skills to where they are today.


Yitzi: Can you share the funniest or most interesting story that occurred to you in the course of your career?

I’m not sure it’s funny, but it’s most certainly entertaining. When I first moved to Nashville I spent time couch hopping, interning, and working 4 different side jobs as I was beginning to build my network and career in Nashville.


In order to make the dream happen, I had to find side hustles and jobs that would allow me to work off hours and late nights. The solution I came up with was to apply at an Adult Superstore as a porn salesman. It wasn’t the classiest position I’ve ever had but it was never a boring day. Over those few months I became the #1 sales person in the region and still have incredible stories to share, but I’ll save those for the book.


Yitzi: What are some of the most interesting or exciting projects you are working on now?

It’s difficult to go into to much detail, due to certain agreements, but I can say that we have grown our client roster 125% in the last few months. We’re working with record labels, artist management firms, booking agencies, and over 50 music festivals around the country. It’s an exciting time and 2018 should be a challenging and rewarding year.


Yitzi: What are you most proud of?

I’m most proud of the culture we’ve been able to build with an amazing young team. In the beginning we ran lean and mean and everyone had to help support each other. Through the 12 hour days and learning curves we’ve built something special, something award worthy. In 2017 the agency grew revenue by over 191% and we’ve had 0% turnover. None of that could happen without my incredible leaders and teammates.


Yitzi: How do you think entertainment marketing has changed over the past 30 years?

Advances in technology and changes in consumer behavior have affected every aspect across all categories. Today an entertainment agency has to be great at creating experiences while understanding data and consumer behavior. We must create and capitalize on campaigns through original content and immersive live activations. For our agency, it’s all about experience, leveraging attention, and creating moments.


Yitzi: What drives you?

The truth is I love my work. I pretty much always have. However, that’s only because I picked a career I am passionate about. I still love music and marketing and now I’ve found that developing others, empowering my team, and giving back are all things that are extremely important to me.


Drive isn’t something I’ve ever been short on. These days when I feel like the entrepreneurial tank is on low, I remember where I came from, how I’ve overcome past hurdles, self doubt, and reached milestones in my career I never thought possible. It reminds me to push harder and enjoy the journey.


Yitzi: Based on your personal experience, what advice would you give to young people considering a career in Entertainment Marketing?

The best piece of advice that I can give to someone who wants to get into marketing in the entertainment industry is simple. Be yourself, be nice, work incredibly hard, learn, network and stay the course.


The music business is not for the faint of heart. It test people in different ways. However, every story shared from my heroes have all been the same. If you really love it, chase it. If you’re going to chase it, chase it with everything you have.


Yitzi: You are known as a master networker. Can you share some tips on great networking?

The entertainment industry is much smaller than most realize. In Nashville, it’s even smaller and closer nit. Relationships are how our business moves and without them it can become very difficult to build a career.


I approach each opportunity to meet someone new as a gift. Chances are good that they know more about certain topics than I do, have different social and professional circles, and may have a lot to teach me. I’d suggest building a relationship and then a friendship, if possible. From my experience, Teddy Roosevelt was 100% correct. “No one cares how much you know until they know how much you care.”


Yitzi: Which skills do you think are most important to becoming a successful marketing professional?

Marketing and advertising knowhow, communication, creativity, and understanding data will help anyone in marketing. I’d add eagerness to learn, willingness to fail, preparing for change, courage, patience and constantly testing new things.


Yitzi: You are in a position of influence. How have you used your position and skill to bring goodness to the world?

Looking out on the landscape of the music industry in Nashville I realized just how needed helping hands are for students, entrepreneurs, and artists. That’s why we founded The Musicpreneur Storehouse, a TN based 501c3 that provides mentorship, consulting, and financial advances for artists and growing businesses in the Middle Tennessee area.


I also serve on the board of directors for another Nashville based non-profit, SOLID. I led a SOLID (Society Of Leaders In Development) committee to match 209 University students with music industry mentors in 2016. Under my guidance the campaign helped to bridge the gap between college and the job market as well as create mentors for the young people looking to work in the music business.


Yitzi: Who are some of the most high profile clients you have helped?

We’ve worked alongside events, organizations, and artists such as Virgin Hotels, WIlliam Grant & Sons, Blue Chair Bay Rum, Hangout Music Festival, Cessna, Kane Brown, The KISS Kruise, Pilgrimage Music Festival, Anheuser Busch, Panorama Music Festival, Saving Abel, Joe Diffie, Rolls Royce, Maui Jim, Sony Music Nashville, Tito’s Vodka, Minor League Baseball, Jim Beam, Michaels, and the Florida Georgia Line Cruise to name a few.


Yitzi: What was that like?

If you do what you love, you never work a day in your life. That’s true for me, whether I’m working with smaller bands and events up to the nation’s largest brands and artists. I absolutely love it.


Yitzi: Which people in history inspire you the most? Why?

There are several, however, Richard Branson and Teddy Roosevelt top my list. Both men are of exceptional character that were dreamers, givers and doers.


Both showcased a willingness to help their fellow man, were faithful with indomitable spirits. They both worked toward leaving a legacy for those in the future. Both were honest people easily balanced with vulnerability and unyielding determination. Both had an incomparable work ethic and were not fearful of failure but aware of it possibility and had the tenacity to drive forward.


They both were dedicated to family and community, both were voracious readers, practiced numerous hobbies, and offered mutual respect, compassion, and friendship to all.


Yitzi: Which company do you admire most, and why?

I’m currently doting on Vaynermedia and ingesting any content Gary Vaynerchuk spits out. However, I think Microsoft wins the most admired award.


The company was started by two childhood friends that had curoristy, natural talent, passion, and has risen to be not only a dominant technology company, but also one of the world’s most valuable companies in any field. In terms of technology, you name it, and they did it.


Computers, software, phones, consoles, games, and they have almost always been at the forefront of technological advancements, as seen with Bill Gates’ ‘internet tidal wave’ memo. Not only have they created some of the most iconic brands of hardware, software and games, but they have done so with the consumer in mind, offering inexpensive products relative to their rivals, and offering plenty of choice. Not only this, but Bill Gates is one of the greatest philanthropists of our time, having given billions to charitable efforts, and having set up the Gates Foundation and the Giving Pledge. Not only has Microsoft affected my inner nerd, but it has helped change the outer world.


Yitzi: What are your “5 Things I Wish Someone Told Me Before I Started” and why.

1. Dreams Change.

I had always pursued this one undefined music dream job. However, through time and experience I realized that dreams change and new unexpected opportunities arise. Now I advocate the passionate dedication to the pursuit of short-term goals.


It’s being micro-ambitious. I tell people to work hard and with pride on whatever is in front of them… you never know where you might end up. Just be aware that the next worthy pursuit will probably appear in your periphery. If you focus too far in front of you, you won’t see the shiny thing out the corner of your eye that could change the dream.


2. Bloom where you’re planted.

Don’t be so ready for the next thing that you forget to learn and grow where you are. The next opportunity will come, they always do. But only successfully when you’ve outgrown your current place. Bloom where you’re planted.


3. Be Hard On Your Opinions

Your opinion should be constantly and thoroughly examined. Be intellectually rigorous. Identify your biases, your prejudices, your privilege, your shortcomings, and think critically. Not just about the ideas of others. Be hard on your beliefs. Take them out onto the porch and beat them with a baseball bat. It will do you good.


4. Be a teacher.

Even if you’re not a teacher, be a teacher. Become a mentor. Share your ideas. Don’t take for granted your experience and education. Rejoice in what you learn and know, and share it.


5. Don’t rush or compare.

You don’t need to already know what you’re going to do with the rest of your life. Life changes and that’s ok. Find what you’re most passionate about and do that. Be patient and don’t compare your book of life to someone else’s. Your chapter 3 is not their chapter 20. Enjoy the journey and read your own book.

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