Basic Info

Aaron Holland
Contributor Status:
Native AdVert
Initial Contribution Date:
Primary Location:
Los Angeles, CA, USA

Career Info

Primary Industry:
Entrepreneurship, Sports, Technology
Personal Career Headline:
CEO, Season Share
Business Description (One-Liner):

There are 3.2M season tickets holders in the U.S. and 70% of season ticket holders share their tickets with other fans. We are the only mobile app that enables fans to buy, group, split and share season tickets to live sporting events. Season Share was founded by three sports fans with deep ties in tech, entertainment, sports and ticketing. Our technology is ready to disrupt the stagnant ticketing industry, increasing team and league revenue while making the fan experience easier and more realistic for today’s consumer. Let’s change the game together.

My Native AdVert

Career Snapshot:

Founder NGST Media 2008 – 2011

Co-Founder Reverb 2010 – 2011

Founder Holland Media Group 2011 – 2017

Co-Founder Simplify Supper 2012 – 2019

Co-Founder LinkMo 2014 – 2016

Co-Founder Season Share 2017 – present

Native AdMission Statement (AKA Personal Brand Pitch):

My name is Aaron Holland, I am co-founder and CEO at Season Share. I was born in the Bay Area but grew up all over the world. My dad helped stand up the first cell phone networks in Europe and Asia, so we moved around a lot. He made sure my brother and exposed to computers at a very young age, something I will be forever grateful for. Going into high school, my dad quit his corporate job and moved my family to a small town in Southern Utah with a population of 500 where I graduated from high school in a class of 19. After high school, I enrolled at the University of Utah, where I studied Sports Management and met my co-Founder Jon Rappaport. After graduating, I spent several years in Salt Lake, where I founded several tech and marketing related businesses and in 2016, finally made it back California.

Shortly after arriving to LA, we decided there needed to be a better way to split and share season tickets. With my experience in technology entrepreneurship and Jon’s experience as a past manager at Ticketmaster, we set out developing a technology that we wanted to exist as fans.

What Else To Know

My Goal of the Day:

Make a list. Every day I wake up early, meditate, then list out everything I need to get done that day as well as anything that did not get done from my previous day’s list. This allows me to stay focused throughout the day and not allow things to slip through the cracks as I get busy. I recommend making a physical list, then crossing things off as you get them done. It’s a nice little feedback loop that enforces accomplishment throughout the day.

My Thought of the Day:

 Focus. Every day I write my three focus words for the year on top of my daily list. For 2019 it’s “Energized – Engaged – Grateful”. I make sure these words remain front-of-mind throughout my day.

My Action of the Day:

Exercise. Even when my schedule ramps up and/or if I’m traveling I make the time to exercise. This is an important act of discipline that will support other areas of your life.

My Deed of the Day:

Invest in people. Every day I make a conscious effort to make someone better at their job. This takes time and energy, but there is a twofold benefit; we have stronger, more capable leaders on our team and teaching allows me to crystallize the knowledge conveyed.

My Tip of the Day:

Routine. Create your routine and live by it. I can’t overstate the importance of this, and it’s different for everyone. Your routine is the most important part of getting where you want to go in life and in business.

My Pic of the Day:
Tell Us More:

Pic of the Day: 

Pic 1: Last “Battle of the Bay” – 49ers vs Raiders @ Levi Staidum.

Pic 2: Fly fishing on the Yellowstone River in Montana last summer.


A Day in My Life:

What do you love most about Your City?

Los Angles, to me, is the greatest city in the world. The energy, creativity, people, and diversity here is amazing and attracts the best and brightest people from around the world. The weather is not bad either.

Favorite breakfast meal & restaurant?

I drink a pint of water and an EmergenC right when I wake up. Then I do a Bulletproof coffee and don’t eat my first meal until sometime between noon-2pm.

What are you doing at:

6:00 AM – Meditating, coffee, listing my tasks out for the day and catching up on tech news.

10:00 AM –  This is prime time for me. I am doing the most important tasks of my day in this block; calls, demos, meetings, and creative work. I work at home, which allows me to not waste time sitting in traffic and increases my effective work time by up to 10 hours a week.

12:00 PM – Favorite Lunch spot/meal?

I hit the gym during this time of day to get away from the desk, reset and charge my energy up for my afternoon/evening work block. For lunch, I usually do a “Big Ass” salad and throw a bunch healthy stuff in. You have to eat something green every day.

7:00 PM – I wrap up work between 7-8pm daily then go outside for 5-10 mins to get some fresh air. I then come back in, throw on a record, cook dinner and read. I recently started wearing blue-blocker glasses as soon as the sun goes down which helps me get into a deeper sleep cycle faster. I make a point to make coffee the night before. It’s much easier to get out of bed in the dark when you know you have coffee waiting for you 🙂

11:00 PM – Sleep.

What drink do you need to get through the day and at the end (and how many)?

I drink two Bulletproof coffees and a ton of Alkaline water throughout the day.

Most used App/Favorite Instagram Account?

My favorite app is Season Share. My most used app is the Apple Health app combined with the Apple Watch as it gives me a ton of actioanable health data from sleep tracking to HRV. My favorite Instagram account is @yeti because it makes me want to get outside.

What should everyone try at least once?

Watching the sunrise in the middle of nowhere.

Where do you enjoy getting lost?

The desert of Southern Utah and the Yellowstone River in Montana. For me, its important to have the juxtaposition of the city and wilderness.


My Native AdVice:

How did you get into the industry?

For me, sports, technology, and entrepreneurship are more than a career and a lot of that comes back to my dad. As both an entrepreneur, cell phone pioneer as well as my high school baseball coach he always encouraged me to remain involved in both sport and technical pursuits. After high school, the mobile phone revolution was captivating and represented the most substantial opportunities for disruption of incumbent industries, so that is where my energy and focus went.

Career advice to those in your industry?

Passion is not enough. Passions change so much through life that focusing on your passion alone is too narrow a focus to allow for the necessary domain expertise needed to make an impact on an industry. You must move beyond your passion and find what I like to call your “primal instinct”, your reason for living. My advice; focus on that thing that you can’t escape, that feeling that wakes you up before your alarm goes off to do again, and again, and again. Find the thing that gives your time on this earth meaning, then chase it with every ounce of energy you have.

Any emerging industry trends?

I am super excited about the forthcoming opportunities created by zero-latency and 5G combined with the opening up of regulations around sports betting and how this will be packaged and presented to the consumer.

Ideal experience for a customer/client?

Growing up, we couldn’t afford season tickets. By the time I got to college, I was able to buy discounted student-section season tickets and fell in love with the connection it provided to the team and the experiences I had that season will live with me forever. I want to make season tickets more affordable and accessible for the next generation of fans.

How do you motivate others?

There are two sides to most tech businesses; the business side and engineering side. What I try to do is communicate how business development impacts the technical team and how technical advancements further enable the business team to be successful. This allows each side of the business to have a greater level of appreciation for the other and allows people to see the positive impact their efforts have across the organization.

My Native AdVantage:

What are my aspirations?

On the business side, my goals are to spend my time solving big problems that make a positive impact on peoples lives through technology. Personally, I want to be better than I was yesterday.

My Biggest Success?

My biggest accomplishment to date is bringing Season Share to market. This project is a great example of the technical and human complexities associated with bringing a an idea to life. I am lucky to have a talented team of co-founders, employees, investors, and partners.

My Most Challenging Moment? 

My most challenging moments are always around getting rid of people. I always want to give people a chance to be successful, which has resulted in me keeping people on for too long. Over time, I have grown to learn that by not letting them go, your actually doing the person a disservice, as they deserve to find a place where their skills can have a better impact.

My Motto? 

Think big!

My Favorite People/Role Models?

I really look up to Elon. I think his contributions to society are actually undervalued, massively. I look up to Mark Cuban and the way he has been able to draw lines between sport and business. I look up to guys like Joko Willink and David Goggins, who remind me that I can’t make excuses.

What Else to Know?

We just launched Season Share with the 49ers and will be adding the University of Oregon’s inventory for football soon as well. If you are a 49ers or Oregon Ducks fan download the app and split season tickets with your friends. Both teams are going to have great 2019 seasons!

Read the book Game Changes by Dave Asprey. Tons of knowledge condensed into one book. You can’t afford to not read this book if you’re a high performer.

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