Today we’d like to introduce you to Asa Gladstein.
Hi Asa, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
I interned for the company I now own about 10 years ago while I was in college. I always loved cars and events and people and this was the perfect vessel to combine all of that plus giving back to charity which is always good.
Interned in 2015-2017, graduated from the University of Minnesota in 2017 and moved to Boston to figure my life out. Started a company called Squad Driven doing rallies and marketing in the north east. Always kept in touch with Crown Rally after internship and finally had a conversation in 2024 to end up buying the company.
2024 was a transition year and 2025 was my first year steering the ship solo. Successful year overall but definitely learned a lot.
We all face challenges, but looking back would you describe it as a relatively smooth road?
Definitely not. The company I was running for about 8 years, Squad Driven, was great for building experience but it was minor leagues compared to Crown Rally. Crown Rally was next level. More clients, larger reach, bigger events, higher expectations to perform.
Buying a business, especially one with such a personal touch has its struggles. I am not the previous owner, although many people did know me from my internship days 9-10 years ago. Also to grow the company I had to move it out of the midwest which rubbed many people the wrong was as that is where it was built.
Before I owned the company, they were coming out of a 2 year hiatus. They used to have 6 full time employees and now I am trying to rebuild this from more or less scratch with some part time help and a great assistant.
Appreciate you sharing that. What should we know about Crown Rally?
I run Crown Rally which is one of the largest car rallies in the United States. A car rally is essentially a road trip for car enthusiasts, heavily focused on fun and networking. We are charity centric and have raised over $1,000,000 for various causes since inception.
We are known for being one of the more genuine rallies focused on people, giving back, cars, and networking. We definitely know how to have fun as well.
Do you have recommendations for books, apps, blogs, etc?
Atomic Habits was a great read, as well as I am currently reading Alex Hormozi’s books about $100M Money Models about building value and offers that make sense. The Third Door was also a favorite of mine, talking about how there is always a way and “no” is not really an acceptable answer if you want to get anywhere.
Pricing:
- Crown West: Seattle to San Diego May 8-17- $16,000 for the whole event or $8,000 per half. Good for driver and passenger.
- Crown North: Salt Lake City to Bozeman August 22-24 with an option to add 25th up to Glacier National Park- $5,000- Good for driver and passenger.
- Crown South: Savannah to Austin for F1 October 19-24- $9,000- Good for driver and passenger. Includes GA Passes for F1.
Contact Info:
- Website: https://crownrally.com
- Instagram: https://instagram.com/crownrally
- Facebook: https://facebook.com/crownrallyofficial
- Youtube: https://youtube.com/crownrally
