We caught up with the brilliant and insightful Dejon Brooks a few weeks ago and have shared our conversation below.
Alright, Dejon thanks for taking the time to share your stories and insights with us today. Let’s start big picture – what are some of biggest trends you are seeing in your industry?
One of the biggest trends I am seeing in my industry is the integration of AI. Weather are you like AI or not, It is here to stay. This is especially true in the travel industry. Back in the day, people would go to their travel agent or ask friends what are the best places to visit. They would even pick up local brochures to know where the best attractions are. Now all you have to do is go to ChatGPT and ask it what to do and I will give you a precise personalized answer within seconds. As far as concerns, yeah, this new piece of technology will significantly disrupt the travel industry, but it also provides new opportunities to help even more people and provide an overall better experience for them. This is what makes my start up Planmyweekend.ai different. We use AI to completely personalize each users experience and provide fully plan itineraries.

Have you ever had to pivot?
This is actually how I started Planmyweekend.ai. I was running an Instagram page that showed locals what events were taking place. This account reached over 100,000 people every month. I wanted to take the page One Direction, but my business partner wanted to keep it the same. This forced me to branch out on my own, start over from scratch and ultimately create Planmyweekend.ai. This would essentially be the same thing, but it runs on AI instead of covering events for one city it was able to cover over 1500 cities at the same time. I’ve had the pivot and start over so many times, but this was one of the most recent ones I had to do. It’s really tough starting over but you know deep down inside that. It will be totally worth it 3 to 5 years down the road.

Can you share a story from your journey that illustrates your resilience?
One story that illustrates my resilience was when I was launching my first company trend watchers. I had spent months getting the software developed and was planning this massive software release. When the day came. I released it everywhere and guess what? I only got one sign-up. This was extremely demotivating, but I did not give up. I spent my days learning SEL and submitting my product to different marketplaces. Fast-forward to today, it is normal for me to get 5 to 10 sign ups daily without taking any action. I have so many stories of resilience from my journey, but this is one of my favorite ones to share with people.

Contact Info:
- Website: https://planmyweekend.ai
- Instagram: https://www.instagram.com/dejon_brooks/
- Linkedin: https://www.linkedin.com/in/dejonbrooks
- Twitter: https://twitter.com/dejonthebrooks
- Other: https://planmyweekendmagazine.com

Image Credits
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