Conversation with Yinka Onayemi - May 17, 2025

Overview

This was a catch-up meeting between Gary Sheng and Yinka Onayemi, an old friend and lawyer. The conversation covered Yinka's career transition to a startup law firm focused on economic justice, Gary's recent work with the Catholic Church and White House connections, updates on family members, and personal life developments. They also discussed technological innovation, AI's impact on professional fields, and entrepreneurial ventures.

Key Points

Yinka's Professional Transition

Yinka has left his previous legal position to join a startup law firm focused on economic justice and litigation against tech companies:

"I actually quit it. I joined a firm. Kind of a startup e-firm. But full of people that were from the old institutions. Like the Big Law Firm. The founder was a former executive board clerk who went to the Big Law Firm. Some former prosecutors of the DOJ, federal prosecutors. It's like 15 people. It's like a ragtime group."

"It's all about economic justice. Suing, going after. It's kind of like private prosecution."

The firm operates on a contingency fee basis, with attorneys receiving portions of settlements:

"We get paid on contingency. I see. That's like a real startup. That's dope. That's great."

Yinka has achieved significant success in this new role:

"I'm like deposing executives of big companies. That's sick. I'm named counsel of record on a $200 million lawsuit that was filed against Doge eventually."

The lawsuit against Doge involves the termination of grants for National Endowment for the Humanities scholars:

"It's because Doge facilitated the termination of grants for National Endowment for the Humanities scholar. Authors who ended up getting grants from the government. Oftentimes, professors taking a year or two to leave to write a book for a big project. A lot of them midway through their..."

Gary's Recent Activities

Gary mentioned several of his recent activities:

1. Catholic Church Digital Transformation:

   "Last year, I did a bit of that [advising on innovation]. Long story short on that, we made some progress. But because a lot of what we were trying to do is weed out inefficiencies and corruption. They didn't like that. And enough to want to keep it going. I feel like the Catholic Church is particularly anti-innovation."

   "But I'm still tied with a lot of Catholic leaders that actually wanted change."

2. White House Faith Office Connection:

   "So, one of my mentors, she's like in her 70s. Long story of how we got connected, but we get along really well. And she's close with the current head of the White House faith office. And that lady, Paula White, wanted to gather faith leaders and was like, Hey, can we add Gary?"

   "I was actually very impressed by the head of that office. And I also met with, just because I was there and that person wanted to meet with me, I met with one of the leaders of the crypto division. We actually just ended up talking about AI and education."

3. Co-living Experiment:

   "Before... Specifically... a two-month long co-living experiment where we took over a resort town. If you take over every apartment, there's like a few hundred people in capacity. And so we did. It was an off-season. We got people at crypto, AI, biotech, and some other fields. Cross-pollinated for a while."

4. Presentation in Rome:

   "Ultimately, didn't want to proceed with the current collaborators I was working with. It was kind of good timing. I got invited to go to Rome to present on this even-flourishing framework that I had helped out with in partnership with a couple of other groups."

Technology and AI in Professional Fields

Both discussed the importance of embracing technological innovation:

"A firm that's willing to embrace AI to more quickly write whatever you have to write. Seems like it would be able to outpace a giant firm."

"Even at a more granular level. Individual attorneys willing to embrace it are going to do better. Law firms willing to embrace it are going to do better."

"I think it goes far beyond the law. Thank you so much. Is there any industry willing to embrace it?"

Family and Personal Updates

1. Yinka's Family and Temi's Startup:

   "We're good, yeah. We're all good. Temi is... He's actually working on a startup right now. Cool. It's called Moth."

   "Honestly, it kind of reminds me a little bit... I think you watched what we were doing with Mason, and that inspired him. It's not political, though, necessarily. It's about... Bringing people together. It's like a social... Connectivity. Bringing people together."

   "Like Yelp or something. Bars and restaurants with a more humanistic touch. Moth is a great name."

   "He's kind of in that moment in life where he's 27, working and trying to start a startup, and he's kind of, like, clawing by the seat of his pants."

2. Gary's Family:

   "They're good. My parents just got... Started... I think it was like a week or so ago. They just landed in China. To go take care of our surviving grandparents. Two grandmas."

   "My parents both... Well, my dad both... My mom retired a few years ago, but my dad retired and then unretired. We got bored, so I actually wanted a little bit of money. And then he re-retired at the end of last year."

   "They moved to Las Vegas. Not for the gambling, but for, like, the suburbs where there's a lot of pickleball. And no taxes."

   "And my brother's wrapping up a divorce. Oh, no. But... Was he married? I don't remember when he married. That must have been in the last, like... Two years. Yeah. He got married in, I want to say, 2021."

Dating and Relationships

Both shared updates on their personal lives:

1. Yinka's Relationship:

   "I don't know if you ever met or... Heard about my ex, Katie. I don't know if we met. No, we didn't. Probably not. We dated for like a year and a half. Oh, wow. Two years ago. Well, three years ago. We broke up for around the same amount of time. And we recently started to, like, see each other again."

   "It's been, like, kind of rocky. It's always weird to, like, get back with an ex. It's like a bit of a time warp."

2. Gary's Dating Life:

   "How's your dating life on that note? So... Abundant. Abundant. I mean, it's weird. Because, like, I feel like I've been... At this point, I've been in New York for a while. Before that, I was, like, traveling a lot."

   "Like, it's been abundance. But now I'm in the point where I'm, like... What next? Kind of, like, yeah, jaded. Like, it's not a great time."

   "I'm just naturally focusing on other things... This thing over here, what am I going to do? What note am I going to play?"

Reflections on Innovation and Education

Both expressed concerns about innovation in established institutions:

"We are very worried about the world where Sam Altman gets to decide everything, including, like, you know... I guess, when I say we, it's like the organization has been thinking a lot of... It's thought longer than anyone, I think, about how to weave in technology and education and humans, importantly, and supporting..."

"I mean, honestly, our education system is so antiquated. I just have... It's funny, I mean, this conversation happens whenever you think about innovation. You want to innovate in the right way."

Observations

1. Both Gary and Yinka are at pivotal professional points, embracing innovation and taking calculated risks.

2. Yinka's transition from traditional law to a startup firm focused on economic justice reflects a desire for more meaningful work and greater autonomy.

3. Gary's work spans multiple domains - from advising religious institutions on digital transformation to co-living experiments and international presentations.

4. Both acknowledge the transformative potential of AI across industries, particularly in law.

5. Despite professional success, both are navigating more complex personal lives, with Yinka rekindling an old relationship and Gary focusing more on work than dating.

6. Family remains important to both, with updates on parents, siblings, and partners forming a significant portion of their conversation.