Black Tech Founder on Pitching to the Sharks and Cuban’s Remark on ‘Entitled Millennials’

Ryan Diew pitched Trippie on the Season 9 premiere of ABC’s Shark Tank. After the show, Black Enterprise contributor Brandon Andrews sat down with Diew for an interview about the show and his mobile app that helps travelers navigate and find what they need at the airport.


Brandon Andrews: Trippie makes navigating airports easier. Tell us how you came up with the idea.  

Ryan Diew: Two years ago, after a long week of finals, I was on a layover in DC headed home to Oakland. I forgot to pack a lunch in the airport so I was pretty hungry. On my layover, I wanted to get food but I had no idea where anything was. I immediately searched the app store for “airport app with airport maps” to see if there was anything out there, but I couldn’t find anything. I had to trust a stranger with my three carry-on bags while I went to find food. It was at this moment I decided to build a solution myself.

Why are you passionate about solving this problem?

I really like that we’re solving a problem that millions of people deal with every day. I really believe Trippie can change the way air travelers spend their time waiting before flights in the airport.

You built Trippie while you were a college athlete. What advice do you have for other entrepreneurs wanting to build apps themselves? 

If you want to do something, just do it. I’ve had a lot of people say to me, “I have this great idea, but I don’t have a motivated developer” and that’s the wrong way to go about things. I didn’t learn how to build this app in class. I decided to use sources like YouTube to watch tutorials on how to build every single feature I wanted in the app. The internet has significantly made knowledge more accessible and easier.

(Trippie Mobile App Screenshot. Image: Trippie)


When did you apply to be on the show?

My team and I pitched at my alma mater Colgate University my junior year. In our Shark Tank pitch contest, we were able to win $22,000 in prize money. This allowed me to actually buy a laptop to code on which was really awesome. That win led to Trippie being featured in Inc Magazine’s Coolest College Startups back in March. After the Inc feature, we were contacted by the producers of Shark Tank.

A lot of entrepreneurs dream about appearing on Shark Tank. Of course, I thought about it too. However, Shark Tank wasn’t an opportunity we were actively pursuing. I honestly thought we were a bit too early. But, the producers reached out and I took the opportunity.

Your pitch on the show illustrated the struggle of many black entrepreneurs. They have spark and grit, but often lack the capital to build their businesses. Lack of capital can also mean that these businesses do not have the traditional traction profile VCs look for. Tell us about your experience pitching.

I went in expecting to get a deal, but I knew our product wasn’t as far along as I wanted it to be. I was a D-1 college basketball player. Upsets happen every year in the NCAA tournament. The No. 15 seed has to believe they can beat the No. 2 seed for it to happen. I went in believing.

We didn’t get a deal, and as guest Shark Rohan Oza said, they gave me some tough love. My Shark Tank pitch nonetheless has been an amazing learning experience for me.

What lessons did you learn from your experience on Shark Tank?

One lesson I learned is being able to keep a poker face. This business is my baby, and being told that my baby wasn’t ready impacted me more than I thought. Prior to Shark Tank, our team had won thousands of dollars in every pitch competition we entered. It was jarring.

I also learned to take the positive out of every situation. The Sharks were focused on my app data and ability to scale, and—immediately after the show—so was I. That feedback was honest and helpful, but I was so focused on that feedback and that I forgot every Shark saying they liked the idea.

At the end of the day, all of the buzz about my pitch is leading to more site visits and more app downloads.

During and after your pitch, Mark Cuban made a comment about “entitled millennials,” as a millennial entrepreneur, how do you respond to this criticism?

I feel like that narrative is opposite of who I am. My—now famous—monologue wasn’t intended to come across as me feeling entitled. It was intended to demonstrate that I’m worth investing in.

I made a D-1 basketball team as a walk-on. There were no roster spots my freshman year, so I participated on the practice squad and was ‘team manager.’ I even joined the track team to stay in shape in the off-season. I eventually earned a spot on the team. I taught myself to code and built the first version of Trippie myself.

I don’t think anyone owes me anything, but I do feel like my life experience demonstrates the grit needed to grow a business. While I don’t think I’m entitled, overall Mark Cuban’s advice was helpful. The conversation was much longer in person, and the edited version on the show may color it differently. He even follows me on Twitter now.