Conversation with Tyler Tran about Alpha Schools and Potential Collaborations - May 18, 2025

Overview

This conversation was a reconnection between Gary and Tyler Tran, old friends who hadn't spoken in some time. The wide-ranging discussion covered their respective professional journeys, Gary's work with Alpha Schools, Tyler's role at NBA T2, and potential future collaborations. The meeting evolved from casual catching up to exploring serious business opportunities, particularly around specialized sports-focused educational programs with media partnerships. Gary also introduced Tyler to Frankie Colamarino via phone to explore potential three-way collaboration.

Key Points

Personal Updates and Reconnection

The conversation began with casual catching up, revealing they hadn't been in touch for some time:

"We've been friends for seven years... we grew up with each other."

Tyler mentioned his upcoming wedding, which will include both civil and church ceremonies:

"Having a church... Catholic church wedding. Oh, really? Yeah, like two different days. I guess I'll be at both. I think if you want, but it's really just to check the box for friends, family."

Gary shared updates about his personal life, including a past relationship:

"I dated a girl, not Vietnamese. She's a white girl for eight months. And we're still friends... I dated this white girl in Denver for eight months... McKenna Garner... She couldn't have kids because of chronic issues. So we just kind of made the decision that we didn't want to like..."

Gary's Recent Professional Activities

Gary explained his work with Alpha Schools, an AI-first education model:

"I just passed out in the train. There was three things. Number one, the Alpha School stuff... Alpha School? I didn't make the name up... Well, yeah, the name obviously has connotations of leader and men. The founder of it's a woman. But she's kind of like an alpha woman... So, she's been iterating over it for like ten years. With the support of this really wealthy man in Austin. Who's been in software."

He described his recent visit to Washington, D.C.:

"DC was about basically advocating for that. In front of powerful people... And then the other one was... The White House visit was like a half... The whole half-day summit at the Eisenhower building... It's like all the White House. The Eisenhower building was like a mini conference of faith leaders."

Gary also mentioned his past work with the Catholic Church:

"I have advised the Catholic church... I was helping the church think through a lot of like... Catholic church last year, from like June to ultimately December... We uncovered some stuff about... Some papal candidates... We were trying to help them address race in the leadership drive... We were able to identify... Cardinals that were stealing money... But then they shut it down."

Tyler's Current Professional Role

Tyler revealed his position at NBA T2, a joint venture between the NBA and Take-Two Interactive:

"I'm with the NBA... I'm head of FNA for every business in LA... NBA Team Student Media... They used to have entertainment media on NBA that's partnered with Take Two Interactive... Take Two Interactive's like one of the big three video game companies, like EA, Take Two, and Activision Blizzard."

He explained a shift in business strategy away from esports to short-form content:

"Right now, we're wrapping up all the games. Every week, we have a new one... But it's only like one-fifth of the games... But there's no longer my focus. That's just a business that, like, well, it's not really worth it. It's not gonna make money... EA Sports as a business, is not, it doesn't have a multi-deal market."

Tyler described the changing landscape of sports media consumption:

"So now, I feel like, you know, like, it's, you know, we, we, the new consumer, of, you know, NBA fans, where they are... Which is, short-form entertainment, branded content... Because people now don't, Don't even watch. They don't even watch full games anymore. They don't watch, like full broadcast anymore. People are consuming content now, especially sports people. Sports content, TikTok, Reels, Highlights at most. That's where the new sports consumers are. And they're not men who are into sports anymore. They are everyone, including women, who are into like the lives of these players. They're more interested about their kids, their lives, their life. So these are like the entertainment around sports, versus the game itself. The game itself is no longer like the main thing."

Tyler also mentioned his plans to leave his current position:

"I plan to actually leave at the end of December after I get my bonus."

Potential Collaboration Opportunities

Gary proposed several collaboration ideas, particularly around sports-focused educational programs:

"We're going to start the best sports schools in the world. And we want media partners. So for example, if we started a Trump Golf School, that's a traveling golf school. One week here, one week here, one week here, one week here. Imagine a bunch of like amazing 12, 13 year olds just crushed by, but then like you help us create like celebrity profiles of all their kids and stuff."

He specifically suggested a Chicago Bulls feeder school:

"So we want to do the best basketball schools too, right? Where in Chicago, my first degree network of people that are excited about alpha schools, including me. You know, Tony Cucco, Soddy Pickens, Michael Cole, and then Bear Crows, the Ball Brothers, you know. And the Chicago Bulls are going to do this in itself. And so we like, what if we did a Chicago Bulls, okay, middle and high school, and then partner with you as a media partner?"

Gary emphasized the business potential and impact combination:

"This would be profitable from day one. Whatever we do. Because like you said, okay, this, first of all, this would be the first of its kind... I'm also trying to like, bring more life back into Chicago. I know the next mayor, Alexei Vinoglius... The mayor, the governor, and other very, very, very powerful people in Chicago. Including like, top pastors and stuff. They'll be very excited about this."

Philosophical Discussions about Career and Impact

Tyler expressed his pragmatic approach to career decisions:

"I care. It's just. Like. Like what you're saying. Right. There's just not money in it. Like. I can't. Right now. I'm like. Supporting. So many people. You know. Of course. Yes. And I choose to let all that go. And do what I actually think is great. No. No. You should not have to choose."

Gary reflected on his own career journey:

"My parents are very happy. Because they're like. Gary's. Finally Gary. Gary's self-sacrificing. People. People. It helped me build a lot of relationships. In my 12. Over the last 10 years. Yeah. Because people know that I'm not. Just about money. No. That's very important. For them to trust me. But now. Now I want to make money. Too."

Tyler offered philosophical insights about career paths:

"But look at that. You weren't chasing the money. You were just chasing. Knowledge... It was good... Yeah. Right. It's kind of like. Falling in love. I mean. You're just doing the love. Which is. Learning. Falling in love. Yeah. You couldn't. Exemplify. Any more. Than like. Chase. Chase what you like to do. And the money would follow."

Introduction to Frankie Colamarino

Gary introduced Tyler to Frankie Colamarino via phone to explore potential collaborations:

"I need to connect you guys, because where does T2 in terms of, it's like development, right?... I already did... My network is just gonna get bigger and bigger and crazier and crazier, so. Because, honestly, it's like the ultimate power move. Every parent cares about their kid's education."

Frankie shared his background with NBA connections:

"We have one of the largest, we were talking about this the other day, we have one of the largest Instagram networks in the world, we're at about 70 million across all pages... So, we do a lot of work with VaynerMedia and a few other larger-scale agencies... So, we also work with Drew Hamlin, who's the number one skills trainer in the world... Joel Amid, Zach Levine, Tyrese Babsey, Tyrese Sullivan, Jason Tatum. He kind of represents everybody under the sun."

Sports and Society Discussion

The conversation included a brief but interesting digression about socialism in sports:

"It's actually the most socialist thing. Well, it makes it more interesting so that you never know who's going to win next... Like, even Americans involved in football, they don't realize it, but they hate socializing. So they didn't realize that football is the most socialist. Right. Everyone has the same wallet. Because of the wallet... Because they keep the funds. Yeah, I think part of what you're saying is socialism can make things, keep things interesting... Because you never know who's going to win. You can say it can make things competitive, which is like so opposite."

Observations

1. The conversation revealed a strong friendship between Gary and Tyler with a comfortable rapport despite not having been in touch recently.

2. Both men are at pivotal career points - Gary fully invested in Alpha Schools and Tyler planning to leave his position at NBA T2 after December.

3. Gary's business approach appears to have evolved toward combining impact with profitability, particularly through specialized educational programs with built-in monetization strategies.

4. Tyler offers valuable connections to the NBA ecosystem and insights about changing media consumption patterns that could benefit Gary's educational ventures.

5. The proposed Chicago Bulls feeder school represents a concrete collaboration opportunity that leverages both their networks and expertise.

6. Gary functions as a connector, facilitating an introduction between Tyler and Frankie Colamarino that could lead to further collaborations.

7. Both men seem to value the balance between financial success and meaningful impact, though they approach it from different perspectives based on their current life circumstances.