From Microsoft to Memes

One day you’re working your cozy corporate job at Microsoft, and the next you’re making memes about why Salesforce is the devil’s software.

Such is the life of my friend Jameson Zaballos — co-founder of Napa, a ghostwriting agency for VC-backed startup founders that actually knows how to be funny. He’s also a power user of Memelord Technologies where he makes viral memes for his clients.

Jameson started the company with the legendary X memelord Chris Bakke, who shitposted his way into a $100M+ acquisition by Elon Musk.

I sat down with Jameson—and our AI notetakers, TWO OF THEM—to talk about his sense of humor, his parents’ weekly All Hands, and how he hires funny people on the internet.

Jovian: What's up, dude, How's it going? Good? Wow we have two AI note takers here

Jameson: If you want I can sign up for like a third? Maybe I can get like a third going

This is the first time I'm using my own note taker in the meeting and I feel like a cuck.

[laughs]

How are you doing? How’s business? It’s 11pm here. See how much I miss you?

Oh, that's so sweet. Next time I'll do mine at 11pm. Business is good. It's hard to find people who are funny.

Are you the funny guy growing up? Are your family members funny?

I don't know. I feel like, for my entire life, I've been the person who makes the jokes that no one laughs at, but I think are hilarious for like, pretty much all of college and all of high school. Sometimes I thought to myself “why are you like this?”, but I just couldn't stop doing it.

We're a pretty humor oriented family. So I wouldn't say that I'm the funniest person in the family, but I would say I’m the one who makes the most jokes, I have the most surface area. Do you know what Mystery Science Theater is?

No.

This show that happened in the 90s on, like, old Comedy Central, where they would take these absolute dog shit movies from the 50s and 60s, and there'd be these three guys, one of them was a human. Two are robots. And they would just make fun of the movie as it happened.

My dad was obsessed with it. My mom liked it too, and I think that really formed a bedrock for my humor growing up. I guess I was just the one who made the most jokes, and for up until what, 18 months ago? There was no monetization strategy. It was just part of my personality. I think it's finally starting to bear fruit..

Funny that you mentioned that your humor is kind of based on that movie stuff, because I found videos of you on YouTube streaming video games….

You did your work, you did your research. I forgot that they're still public. Do you know who Nardwuar is?

Yeah, I know Nardwuar

Yeah, that's how I feel. Like I'm getting Nardwuard right now. Because nobody talks to me about my videos on YouTube.

Before the pandemic, my dad got back and got into video games for the first time thanks to my brother, Christian, sort of like, getting into Halo. 

So we started playing games together every Wednesday and Saturday. Then during the pandemic, I was like, well, I've been recording this locally to my hard drive. I might as well stream this. I think at some point I have like, a couple hundred followers. Not subscribers, followers.

On Twitch?

On Twitch, yeah. I stopped streaming when I started interviewing for jobs.

Speaking about jobs, why did you become an engineer?

It goes way back to…my dad was in tech. You know like the Silicon Valley meme of like that guy going “I put radio on the internet”? His company put audio on the internet. It's called RealNetworks in the late 90s. So he was always around startups.

I was a top 10 trombonist in the state of Wisconsin, which doesn't get you anything. There's no career path there. So I was like, Well, okay, music is not the path. I still make music though.

Okay so back to my dad.

He was a pretty big proponent of computer science. I entered college as a double major in Computer Science and Music. Dropped the music major within like two weeks.

In hindsight, I got out of ‘Nam in the last chopper. This was all right before AI, right before ChatGPT. There's some kids in college who are 100x engineers because they have AI.

I think I would have been the person who just relied on it more than improving with it.

So in short, I rawdogged college.

Are any of your siblings also an engineer?

No. My sister's a math major. She works in cyber security, but on the product marketing side. Sure. My brother's a lawyer. Other brother is on a path to becoming a doctor..

And you're making memes on the internet.

Yeah, people still don't really understand what I'm doing, by the way.

Do your parents understand what you’re doing?

Yes, they actually do! People in tech have this “Oh, my parents don't understand what I do” meme, but they get it. My dad is in tech. My mom is an amazing, excellent writer and editor. So, like, what I’m doing is sort of the marriage of those two things. They just get it.

Literally.

Yes, literally, and figuratively.

So when you left your job and started a meme content company, they're not worried about you at all?

I have the greatest parents on the planet. They're like “we're here if you need someone to talk to, but we trust you.”

My mom is incredibly smart and has a writing background, she gets the agency and marketing angle. My dad gets the startup angle.

I think we talked about this with Jason when we were in New York, but when I was a kid every week I'd have 1:1s with them on Sundays. Every Sunday night we'd have a family meeting, which is basically all hands. So they totally run a tight ship.

I have to be honest here. That’s fucking insane.

I fucking hated it. I mean, hate may be a strong word, but I hated every Sunday.

Every Sunday we’d be like, “Here are our goals.” It was very action-oriented.

To their credit, it was super helpful. Family meetings would always happen after dinner. They’d be like, “Alright, here’s what’s gonna happen this week. Christian is doing this, we have Friday night open. Do you guys wanna do takeout?” It was incredible.

That's how I would want to be remembered as a parent: action-oriented.

If your parents aren’t as funny as Jameson but you want to make money with memes, Memelord Technologies is just the tool for you.

Jameson also uses Memelord to coach his clients on how to make memes. Keep reading to find out how he does it.

You grew up in, well, a writer's family, so to speak.

Yeah, reading and writing were always very prominent. My brother Ben and my sister Emma are both tenacious readers. That's how I got into writing. When I was in high school, my mom would just sit and absolutely tear apart my drafts. She’d be like, “I don't understand what this sentence means.” “This sentence is pointless.”

Another good lesson here: if you're getting really brutal feedback and you just keep going, that's a passion. That's something you should follow. Because, God, if I wasn't passionate about this, I don't know how I'd be able to do it.

How does it feel to you when you write?

The best analogy I can come up with is, once you embrace creativity you have to understand that creativity is not linear input to linear output.

I can spend 18 hours writing, and two of them will be amazing and 16 will be terrible, and I just accept that sort of how the day goes. It's like when you are trying to find a puzzle piece that fits and you know what it's going to look like, and you know how it's going to feel when it's right, but getting there is a lot of stuff that doesn't feel right.

It's a lot of sentences that are like “No, this is not getting the point across”. It's a lot of revisiting and seeing that it's still not right, but when it feels right, you know, yeah, this is it.

That's why I'm totally comfortable sitting down and just writing complete dog shit for an hour, because I'm getting closer to the stuff that's working.

How about when you’re making memes?

It’s the same. Typically the idea will come before the meme.

I was walking down the street the other day and I was like my fiance was talking about interviewing the candidate or for a remote position.

And I was like: wouldn't it be funny if you showed up to the person's house and did the interview in person? And that's the idea.

There’s still this messy middle between the idea and the post. You can absolutely botch a funny concept. But sometimes with memes, I'll see something funny, and then I know that’s gonna make a great meme, you know?

Yeah, I can relate to that. The meme visuals also kind of help with that.

Totally. You see it, you're like, Oh, I know exactly what this is

“If you're getting really brutal feedback and you just keep going, that's a passion.

That's something you should follow."

I want to talk about your entrepreneurial journey. So you’re partnering with Chris Bakke. How did you guys meet?

It's totally random.

Before that, the main point I want to get across to people when they're like, “Wow, so cool. You're a cofounder. You're supporting yourself” — it's all on the back of Chris.

He worked really hard for a long time in his career, made a lot of connections, and this is part of the fruits of that labor. So I definitely started this entrepreneurship journey on third base, and I make no mistake about that.

Back then, I hadn't figured out the monetization part of writing, but the passion was there.

So when ChatGPT came out in 2022, I wasn’t like, “Oh, this is going to kill writers.”

My attitude was more like: this is a really cool thing that's happening. So in 2023, I just started writing about AI every day. I was at a point where, professionally, nothing much had changed, and I knew writing was the passion. I wanted to get better at it.

I did that for four months, and that’s how I started getting better at writing. I did that and copy work every day for all of 2023. The newsletter shifted to basically writing for myself on a blog about how to get better at writing.

The year ends with nothing professionally to show for it, but I'm a much better writer.

All that preparation paid off, because I think January 7, 2024, or something, I joined this online slack group that Charlie Light created...

That’s where we met!

Yeah, yeah, exactly, yeah. Man, thank God for that group, right?

I'm not sure we’d be under the same circumstances if not for that Slack group.

So I joined that group. Didn't expect anything of it. But then Chris posted one day. He was like, “Hey, I'm looking to hire for a position I'm calling a “Meme Intern.’”

I was like, that sounds cool as hell. I was at Microsoft at the time, so I didn't have to work for money. So I just DM them a few examples of memes that I made on Twitter and said “I'll work for free until you see ROI on this.”

To his credit, he said “no, I'll pay you” - It started off at like  $10 a meme. I did like 10 memes a week. Eventually it became $200 a week, and then $2,000 a month. Eventually we just started splitting the revenue.

A lot of Chris’ brand was built on founder-led content. That was how he got his company acquired by Elon. through founder-led content and a lot of shit posting.

People he knew in San Francisco were like “Hey, can you do this for me?” And he started doing it, and realized it was a lot of work. So he just sort of folded me into this whole process.

I was working probably 20 hours a day between Microsoft and this, and was miserable from a health standpoint, but I was super happy. I thought this could be a real thing I want to do. 

So I tried to quit my job at Microsoft, and my boss and my boss' boss both said “Please don't go.”

I was like “I'm sorry, guys, I love working with you, but this is really fun.” Then I officially quit.

Was there a specific point when you realize that, hey, I can actually do this full time? Do you remember what it was like?

I was much more cautious about it than I think most people should be. I waited until I had basically consistently matched my income from Microsoft. Because I want to make sure that this isn't a dumb idea.

Makes sense. What was the conversation like between you and Chris? Was it about co-founding with Chris? Or only working for Chris to start with?

Co-founding was pretty much always the conversation. I'll give Chris a lot of credit for that. That was the whole conversation. It was always like, hey, let's do this together.

I don't think I would have been as willing to quit if I didn't co-found the company.

I wanted something that was a large departure from working at a big company and own more of the upside, a true asymmetric bet that could pay off. I don't think I would have been as eager if equity wasn't on the table.

So is Chris still your co-founder? It doesn’t show it on LinkedIn

No, he is the co-founder. He’s strategically involved on the day-to-day with clients.

To be honest with you I still feel like I'm… I wouldn't say cheating, but I'm definitely playing the easy mode version by working with someone like Chris and our incredible sales guy, Kevin.

I have never truly had to do the desperate, cold outreach sales. Thanks to that.

Oh, you're very humble. That's sickening.

I also don't love talking about myself. So you're getting a rare version of me.

When we were in New York, you told me you find it hard to find funny people. Can you talk more about that? Why is it hard?

Funny people are the scarcest when it comes to content resources.

Because even if ChatGPT gets trained on a bunch of really funny content, you have to know what that looks like to be able to surface it. Typically, what a lot of people think is funny just isn't really edgy enough to capture a broad audience.

I’d say that’s our biggest struggle: finding people who are natively funny online, understand why specific accounts are funny, and can take that humor and condense it into a hot meme template.

So how do you hire these funny people?

I just started hunting around LinkedIn for People who just do it for the love of the game.

That's how we hired our Founding Account Executive Kevin (Baker). He made a funny post about how he was so dedicated to his job that his boss called him saying that they needed $500 in Apple gift cards. And he was like “I delivered!”

The joke is that it’s obviously a scam, right? It’s a shitpost. But then his actual boss goes “You can't post something like that.” and he was like: “Well, cool. I don't want to work here anymore.”

There's more of that, but that was basically it: finding people who are just posting for the love of the game and aren’t required to be funny as a job. That's the muscle that we're looking for, and it's hard to find.

I can imagine that’s pretty hard.

The other thing that's hard to hire for is—I know it's kind of been beaten to death—but the term “agency.”

People who are proactive in Slack, people who are anticipating what a client might have questions about, people who are going above and beyond. That's tough.

We’ve found those people, but it’s tough.

“Funny people are the scarcest when it comes to content resources.”

Some clients want more serious stuff, and some want to post more memes and be silly online right? Do you just follow what they want? Or do you give recommendations?

A lot of it depends on where they got referred from. If they’re like “Oh I love your work with x account” then I'll take that as sort of a “This is the direction I want.”

We also have clients who clearly made a name for themselves from shit posting, and we're just gonna crank it up to 11.

Every single week, we're checking in on the ratio.  Is there too much meme content? Not enough serious content? What stage of the business are you in? Are you fundraising right now, and you'd rather post more about the business? Or did you just complete a fund raise? If so, you might be good on cash for a while. You are comfortable taking a little bit more risk with memes and stuff.

We've had clients where we haven't changed their strategy since we started working with them 18 months ago, and they've gone through fund raises and everything.

I would say the number one direction we pick is more meme content, not less

People sometimes get scared because they think their page is going to look like a meme page, but if you break it up right? That's not a concern.

Do you sometimes have a hard time selling them to be more meme-oriented? Do they have objections?

I always say: let's start with text based memes. I think if you scroll through someone's profile and you see a bunch of texts, you're not going to think of this as unserious, even though half of those are shitposts and memes.

The goal with founder led content is to stand out and to really turn your profile into something that generates leads for you. It's really easy to stand out if you make memes that your ICP resonates with, because they will be like, Oh, he gets it. Oh, this is funny. I'll give it a follow.

Memes are just such a great, easy way to stand out, and it shows your ICP that you really get it. Even if they don't immediately bite on a meme, if you're posting consistently after, they’ll follow in the 30 to 60 days afterwards. You’ll become a mini celebrity for them.

Supabase, for example, they OWN the developer audience, because their account is just so good at posting really funny developer memes, and it's gotten to the point where their memes aren't even that remarkable. It'll be just like oh “engineers logging in to stand up at 8am” and it's like a picture of a monkey in bed.

Yeah, and developers would then be like “YES YES THAT’S ME”

Yeah, exactly. It's funny in a vacuum. I don't think it's 4000 like, funny, but obviously I was wrong.

“Memes are just such a great, easy way to stand out, and it shows your ICP that you really get it.”

Have you ever had trouble with the memes or shit posts you made for clients you shared one with me before?

I stand by like every post that I make, and I'm happy to fall on the sword for any client.

But I have often learned that as your brand grows, you have to be very careful about toeing the line, because the potential positive outcome of a viral meme that's very edgy is almost always NOT worth the potential negative consequences.

There are many cases where I self select where I think the bet just is not worth the hand here. The potential virality is not worth it.

There was once that where the client reached out was like, please do not post about this ever again. So I learned my lesson.

You know what, the shittiest part about like, Trump being so controversial is he is legitimately a really fucking funny guy. Like his comedic timing is incredible.

The sentences that he says are batshit insane and hilarious, but you just, I've learned that, like, for certain accounts, you just can't use those formats, and that's fine

Yeah, totally. The Mr. Japan thing is actually the funniest thing I’ve ever heard from him so far.

Mr. Japan's hilarious.

There's a video from his first presidency where he’s like “are we all getting good photos of me, like everyone looking nice and thin?” I'm like, that's hilarious, but I just can't use it.

So your clients: are they actually funny in person?

I'd say there's two answers to this. One, there's a lot of coaching involved. Polishing a meme that a client makes is also part of the business.

On the other hand, sometimes, like the least common denominator, the slowest form of humor, like super simple Advice Animals, 2012 meme era type shit, goes absolutely ballistic viral, and people love it.

I had that happen a few weeks ago. A client was like, hey, what do you think of this meme? And I was like “meh” I'd probably post the other one instead. I think it's funny. They're like “I don't like that. I'll just post mine.”

It got like 160 likes on LinkedIn. I was like, shit, you were right. Sometimes your pulse is off. Most of the time, we're correct, but sometimes it's off.

Wait a minute, so you also coach your clients to make their own memes?

Totally, yeah,

How does that work?

You start with, like, good copywriting principles, and then you give them examples from Memelord Technologies—great memes, great formats—and eventually it starts to click, and they're like, “Oh, I sort of get how this works.” Then they'll send you something, and you'd want to change this or that. It's a lot of fun.

You’re basically coaching them how to be funny.

Yeah, to understand where the humor is. Because every single profession has that type of humor or that type of thing that will resonate.

Quick advice for people who want to make money with memes?

Well, I think the path for making money with memes is pretty well charted.

Pick the niche that you're excited about, do it yourself and keep doing it, and eventually someone knows you and be like “Hey, can you do this for me?”

I think you and I have both seen enough examples of that happening. The problem is it takes like, two ingredients that are really tough: First, it takes the actual passion for it, which you can't fake, like you legitimately cannot fake it, especially if it's not your day job. I would not have been able to do any of this if I wasn't passionate about writing, I would have burned out.

The second thing is an abundance of patience. I had no way of knowing that I would have met Chris and everything would have worked out the way it did. You need to have patience. You need to have conviction that if you follow your passion, you can make money and eventually network your way into finding something.

But you can't know that until you do it. You truly cannot understand that until you actually go through it.

So like, the patience and the passion, combine those two things, and like, be really consistent about it, and I think it'll work.

Chase Passive Income (@chasedownleads), Jason (Levin), these people have laid out the blueprint.

“You need to have conviction that if you follow your passion, you can make money and eventually network your way into finding something.”

Who should hire you?

if you are a B2B SaaS doing between five to $25 million in revenue in a crowded space, I think you're doing yourself a huge disservice by not doing founder-led content with a meme angle, and especially if your competition are not active on LinkedIn, or they are, but they suck at it.

There is just such an opportunity there that you are not taking advantage of. And the potential, like, grows as you break out of that growth stage, and it will follow you. Your following will follow you no matter what you do.

If that is you, you can reach out to Jameson on his LinkedIn, X, or book a call with the Napa team.

Tell them Jovian from Memelord Technologies sent you. I want him to be indebted to me.

All right. You mentioned you make music? What music do you make?

Yeah. I’m a high school and college trombonist. I love jazz. I can't really commit to that right now because my life is too hectic, so I did like what every white guy does, and I got into DJ-ing.

[at this point Jameson showed me his turntable]

Oh God.

So that's been sort of like my creative outlet right now.

[awkward silence]

Anyways thanks for the time man!

Yeah if you need anything else, happy to hop on another call.

No, I will never talk to you anymore.

Yeah, one hour is enough.

That was the convo with my friend Jameson — who I’m seriously considering blocking now that I found out he’s also a DJ. That was an eye-opener.

But if you want to hire him for ghostwriting and memes, he’ll absolutely knock it out of the park.

You can find him on LinkedIn, X, or reach out directly to the Napa team.

Thanks for reading!