Meet Caleb Street | CEO & Co-Founder, Trolley Strap

We had the good fortune of connecting with Caleb Street and we’ve shared our conversation below.
Hi Caleb, every day, we know how much execution matters, but we think ideas matter as well. How did you come up with the idea for your business?
I knew what type of business I wanted. I knew what type of problems I wanted. I also knew the reward that would make it all worth it. I knew from my corporate purchasing background I wanted to build a product company, something that would be truly scalable. In 2018, after I had been fired even as a high performer, I knew it was time to chase the small voice in the back of my head I had been ignoring for years; entrepreneurship that would be truly scalable. I started businesses and make changes; one such change was reading. I read a book that solidified and put a concrete strategy ahead me. It was the same path but my direction was murky at best until I read The Fastlane Millionaire by MJ DeMarco.
Years went by and I had many ideas and businesses. Over the years, my girlfriend had adopted the concrete framework I was working towards (she was a serial business owner before we met as well). We set up a framework of criteria products and business ideas had to meet. Then we began brainstorming together; we kept a shared note and added ideas to it all of the time. Just after we got married in 2022 I was trying to focus on a single venture as I had been trying too many things at once for a few years and she was working on a new invention in the travel consumer space. I helped here and there but largely stayed in my own lane. She invented our new and novel product out of necessity.
She had begun traveling more for work in 2022 and could not find a tote bag with a built in trolley strap that she thought was fashionable. All of the bags she found with this feature (a trolley strap to hold the bag on top of your rolling luggage) were plain or had some other issue. Why couldn’t she conveniently use her current and favorite bags during travel? The Trolley Strap was born over the next months.

Can you give our readers an introduction to your business? Maybe you can share a bit about what you do and what sets you apart from others?
We are coming to market with a completely new and novel product. We are most excited about the potential of becoming a household name, nearly everyone has the problem our product solves!
Business growth is like most everything in life. It’s hard and comes with challenges. I believe the best way to grow is choose the hard road because it pays man dividends. If you choose the easy road, your life will be just as hard with very little rewards. That is easier said than done and of course we all of the days where we choose the easy road. Success in business and life comes from the process of doing hard things consistently. I overcame challenges with a mindset shift; it’s simple, not easy. And the shifts didn’t come that day or even that week but consistently get yourself back on track and you will be amazed at how fast change can happen.
I want the world to know that while business success is wonderful, there is never anything better than the present moment. Tackle your goals without losing sight of the now – enjoy the ride!
Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
We would definitely need to eat at Hash Kitchen for brunch and a nice dinner at Maple & Ash. Old town nightlife would be one stop but another would be a nice day on Canyon Lake with awesome views and huge canyon walls.
Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
Yes, absolutely! MJ DeMarco, author of The Millionaire Fastlane, absolutely changed the course of my entire life in 2019. Reading his book was a huge awakening. It was the logic and formula to achieving my goals. This impact is immeasurable and I have passed it on to others now following their dreams and making more money than they ever thought possible!
Another shoutout to my wife and business partner, Tiffany! She is the best day to day support of love an encouragement. I can’t say enough how impressive her creative ability is, it is because of her creative skillset we are able to conquer our dreams with a completely new and novel, patent-pending, product!
One more shoutout to my best friend and past business partner, Sean Normoyle. Sean did mentor me in real estate and it hugely paid off, I would not be where I am today without his guidance. He has and continues to motivate me to aim higher, keep pushing and stay on track! His success has been amazing to watch but seriously motivating to my own journey!
Website: trolleystrap.com
Instagram: http://instagram.com/trolley.strap
Facebook: https://facebook.com/trolleystrap
Other: https://www.tiktok.com/@trolleystrap
