I have a lot of conversations with people who are waiting for the right moment to start showing up online. They wait until they have the right credentials, the polished pitch, or the TED Talk...
And then there’s Nate Fish (tag).
Nate is the CEO and Manager of Israel Baseball, a team now ranked 21st in the world, and the author of King of Jewish Baseball, a blog he launched in 2012 that was, by his own admission, mostly a joke. When I first met Nate, he wanted to learn more about how to continue building his thought leadership online. He showed up to our Zoom call wearing a leopard print hat, with his daughter running around in the background, completely down-to-earth and ready to learn. I knew right away that he was building something unique and special, and doing it in a completely authentic way.
It’s not every day you meet someone who has the guts to show up completely as themselves. So often, we hear the word ‘thought leader’ and picture someone in a navy suit about to go on CNN. I asked Nate to do this Q&A because he’s the kind of thought leader so many leaders I talk to tell me they want to be but don’t yet believe they’re allowed to be: unfiltered and fully themselves. He’s building thought leadership in his own weird, wonderful way, and it’s not holding him back. In fact, it’s exactly what’s allowed him to grow from one wild idea to being in the dugout with some of the world’s top athletes.
This conversation is proof that you don’t have to wait until everything is polished to start.
---
Brynne: You’ve described yourself as “King of all Jewish Baseball, literary genius, master blogger, professional exaggerator, and most important artist and rapper of the 21st century.” That’s quite a bio. You’ve also said King of Jewish Baseball started as “mostly a joke.” How does something that starts as a joke become an actual identity and a movement?
Nate: One of the cool things about art is that you can put your ego into it — like rap music or WWE wrestlers. You can create an alter ego and say things you’d never say in earnest to someone in a conversation. King of Jewish Baseball was an opportunity for me to build a compartment for just being sensational and having fun and really trying to entertain people.
It was serious in that I’d already been part of Israel Baseball for five years. But it was a joke in that it was fun — and also that most of what has happened since hadn’t happened yet. There was a manifestation element to it too. Just throwing it out there. And then ironically, a year after starting the blog, I was asked to move to Israel and become the executive director. So the jokey title came first, and then it kicked off 15 years of actual hard work to try to live up to it.
I’m also just a chronic oversharer. It wasn’t my first blog attempt. I have a small independent publishing company, I’ve put out several books. I just have a really strong instinct to share.
---
Brynne: You wrote that you “stood outside for 10 years, then snuck in the back door.” I talk every day with people who are sitting on the sidelines — real stories, real experience — but they hold back because they feel like they haven’t made it yet. They don’t have the TED Talk. They haven’t published the book. What would you say to the person standing outside right now?
Nate: There are a couple of ways to get to the top. The first is you’re talented or lucky and you get catapulted — that’s what I was hoping for. Wanted to be a big leaguer and skip all the normal parts of life. It didn’t happen.
The other way is to grind it out. Take it incrementally. Roll one opportunity into another into another, creep your way up the ladder.
The thing I keep coming back to is: everyone feels like what they’re looking for is just out of reach. I look at some people and think, wow, they’re really doing it. And I’m sure some people look at me that way — which I don’t think about myself. But everyone’s caught in this loop of when this happens, then I’ll be who I want to be. It’s always just out of reach.
Just knowing that — being somewhat satisfied with where you’re at — allows you to do the thing now. There’s no event that’s going to flip the switch. Just do it now.
---
Brynne: In our first conversation, you showed up with a leopard print hat and your kids running around in the background. It felt very much like I was getting the real Nate Fish. For people who feel tempted to edit themselves before they show up — online or in any leadership position — what advice do you have for them?
Nate: It’s funny because I actually feel like I’m editing myself all the time. So the perception is surprising to me.
The weird thing about being both an artist and an executive is that these disciplines have different thresholds. As an artist, you’re supposed to be free, provocative, say what you feel. As an executive, you have to build trust. Freedom is not the goal. So I’m constantly asking myself: Can I wear this? Can I say this? Can I publish this? I’m always modifying.
Honestly, my own obstacle to the next level is to stop editing myself. Because the truth is, I’m not doing anything wrong. I know I have a good moral compass and I’m doing things for the right reason. I shouldn’t have to monitor myself — but I do.
To answer the question: I would really encourage people to be out there and be themselves and trust the world to receive that. The old idea that executives have to look a certain way, be a certain way — I think what you actually have to be is really good at your job. Competent, smart, with a vision, and ready to execute every day. That’s what matters.
---
Brynne: Your Substack — Israel Baseball Through Your Eyes — donates all proceeds to the organization. That’s a real bet on owned media. Why Substack, and how did you think about your newsletter as a tool for building the sport, not just your brand?
Nate: I didn’t actually start on Substack — I launched on WordPress in 2012. I moved to Substack because it was a better publishing tool and had the ability to monetize content. But that raised an ethical conflict for me. I didn’t want to double-dip on my role as CEO and personally benefit. So I laid awake one night and realized: if I donate all the money back to the organization, I can promote it shamelessly without any conflict.
It’s been great. Over 5,000 subscribers, real annual and monthly recurring revenue. It hasn’t been as financially explosive as I imagined — I think every entrepreneur feels that way about every project — but it’s real, and I’m genuinely excited to make that contribution at the end of the year.
I also customized it so it looks like a website, not a typical Substack. If you go to kingofjewishbaseball.com, you’d never know the back end is Substack. And we rebranded when we made the transition — new logos, new look. After 10-plus years, it was time.
---
Brynne: Israel is now ranked 21st in the world. You launched Israel Baseball Americas in 2024. You’ve written the book, traveled with the team, built the organization. What does the next 10 years look like?
Nate: On the competitive side, breaking into the top 16 in the world would be enormous. That’s the tier that gets included in the premier international tournaments. That’s a real, clear goal.
On the organizational side, what success looks like — if I can build a good enough machine — is actually doing less. Which sounds funny. But I’m on so many calls right now, trying to keep my head wrapped around so many different parts of the organization. Ideally, I want to be on zero calls and have no idea what’s going on. That’s the goal.
I find myself, if I’m not working extremely hard, starting to feel bad about it. But as the organization gets into a more sustainable rhythm, I actually have less to do — which is amazing. I just need to emotionally be okay with that. Remind myself that if I do a good job, I don’t have to do that much. That’s what winning looks like.
---
Brynne: Since October 7th, all eyes have been on Israel in a different way. What role does this team play in this moment?
Nate: The real impact — regardless of political diversity or religious identity on the team — is that we’re just an apolitical force for people to feel good about Jewish people. If the only thing we’re doing is normalizing Jews and Israel as a force for good for non-Jewish people, amazing. If we’re a huge source of pride for Jewish kids to feel connected to Judaism and Israel, amazing.
We don’t even have to say anything about antisemitism or make some kind of literal statement. We just go out and compete. We play in the World Baseball Classic. We’re on international television in people’s homes. And that has an incredible indirect cultural impact — it ripples out into the world without us ever literally talking about the war or anything.
We just get to be baseball players and be Jewish, and it brings people a lot of happiness.
