On Thanksgiving, a minute-long freestyle went viral, and San Francisco collectively winced.
“It feels like you’ve got this blush / So hot, like it’s the Gold Rush,” raps a man in a quarter-zip emblazoned with his startup’s logo. “When you’re here you’ve got the AI / It’s so fly.”
Reviews of the performance (opens in new tab), which went down during a Tech Week event at the private Amador Club, were unkind. The Instagram comment “Sending hate from the East Bay” received nearly 10,000 likes. Another said, “We need to bring back bullying.” And then there was the always popular “Nightmare blunt rotation.”
Similar comments spread on TikTok, Reddit, and X as the video got millions of views. It’s no surprise — the performance was a pure distillation of cringe founder culture.
But the rapping CEO is unfazed. He’s honestly … kind of stoked?
Arun Saigal, founder of the AI app development company Thunkable, says a friend asked him to spit a few bars. Saigal, who has been freestyling since high school, was happy to oblige. But he stressed that he rhymes to have fun, not as part of some “8 Mile” fantasy.
Saigal is in fact a multi-instrumentalist who conducts the San Francisco Civic Orchestra and has been involved in the local music scene since moving from Boston more than a decade ago. In that time, he has raised tens of millions for Thunkable and performed onstage with MC Hammer. Now, he says, he’s rapping at tech events about once a month. He even has “rapper” in his Instagram bio.
Being The San Francisco Standard, we had to contact the 34-year-old founder to find the story behind the clip — and make sure he’s OK after becoming a meme.
This conversation has been condensed and edited for lyrical sharpness.
A video of Saigal freestyle rapping at a Tech Week event went viral. | Source: Morgan Ellis/The Standard
Would you rather go down in history as a founder or as a rapper?
I would like to think of myself as a founder who’s really trying to solve big problems. Rapping is something I love. It’s a great hobby. You’ve seen where my rap lies — it’s fun, but maybe not the greatest thing ever. Right now, we have a big product launch coming — I’m spending 20 hours a day working on the product. I have not spent 20 hours a day honing my rapping skills.
Tell us about the video. How did you end up rapping in front of all those people?
I was among a bunch of friends. We were at an SF Tech Week event, and they were talking about music and AI. I rap a bunch, so they were like, “Can you come up and freestyle a little?” People were shouting out words at me, and I was rapping about what they were shouting.
This was not a fancy stage. No one was paying for tickets to this. And then, of course, a perfect clip of me being pretty terrible was put on the internet, and it went wonderfully viral. Some of it landed, some of it missed, and that’s the joy of having creative outlets. You win some, you lose some.
I assume you read some of the comments. People came up with good nicknames for you: the Notorious GPT, Machine Learning Kelly, Aziz Imsorry.
Notorious GPT was definitely a great one. Biggie was a huge, huge influence, also Eminem, Jay-Z, more recently, Kendrick. When I was a kid, I loved Nas as well. Even people like Bobby McFerrin who do super cool things with their voices, you know, being the human beatbox, making vocals. Bobby has a show every week in Berkeley.
When did you start rapping?
I started rapping in high school, and I’ve been playing music since I was 5 years old. I conduct the San Francisco Civic Symphony. We put on free symphony concerts for the community. I play in a local band, the Wobbly World. We perform all around the Bay.
When I went to high school, I started writing a lot of poetry, and I’m also an Indian drummer, so I was like, oh, poetry to a beat. This is rap. I grew up with rap, and I loved it, so I started doing it for fun with my friends. AI still can’t freestyle rap for you.
Have you ever used AI to write a verse?
I’ve definitely goofed around with that, but most of what I do is freestyling, so I’m rarely writing in advance. I think what I really need to do is have a rap battle with ChatGPT. That’s the most San Francisco tech thing I can come up with.
Do you know any other founders and CEOs with bars? Do you guys ever get in a little CEO cypher?
Oh, there’s a whole community in the Bay Area. A buddy of mine is another [Y Combinator] founder, Vinith Johnson. We often perform together. This guy A’niche (opens in new tab) — he’s a Bay Area tech guy who does it. Ben Horowitz talks about rap. We’ll get together at parties and have fun. No one’s taking themselves too seriously.
Saigal blessed our photographer with some bars off the dome. | Source: Morgan Ellis/The Standard
Do you go to rap shows here?
In the last few months, I’ve seen Jonah Melvon (opens in new tab) in the East Bay. He’s fantastic. Frak the Person (opens in new tab), he’s been making it pretty big now as an SF guy. Shout out to my South Asians: Haji Springer (opens in new tab). MC Hammer did a thing a couple months ago, and I’ve collaborated with him a bunch over the years and performed with him.
How did you meet MC Hammer?
We met at a music event. I was conducting and drumming and rapping. He came with a friend who said, “Hey, you should meet this guy.” He does a lot of tech investing. We ended up staying in touch — that was 10-plus years ago.
We did a thing at August Hall last year, and we’ve performed at all kinds of small things in the Bay.
Is he an investor in Thunkable?
He’s not, but I should probably hit him up for that. We have a bunch of other music investors, like Diplo.
If you could collaborate with one producer and one rapper, who would it be?
In terms of rap, it’s got to be Kendrick. He’s got the lyrical wizardry. And then if I could work with any producer, I’d go with Timbaland. He’s a character who has worked with everybody.
The other direction is you gotta go with everybody who’s been hated on by the internet. So you’ve got to collaborate with William Hung (opens in new tab) and Rebecca Black. I have this vision that we’re gonna have an awesome collab together. That’s a newly invented goal of mine.
That would be huge. They’d probably be down.
I think so. I gotta tweet at them. That would just be exceptional.
There definitely is some backlash on the Amador Club video. Does it sting to read “This is why I hate San Francisco” in the comments?
It’s no fun to have people on the internet who don’t know you hating on you. Does it sting? Totally. But if I watched that and had no context and thought it was a serious tech CEO who’s forcing everyone to listen to him, I’d be like, yeah, that guy’s terrible. And I’d probably blame him too.
What’s great is that there are people who don’t know me who are like, “Why are you picking on this guy?” The amount of DMs and love I have gotten from people I have never met who are just like, “Hey, man, forget the haters. You’re great — way to just be out there.”
Did you get any kind of response from your employees or investors?
One hundred percent. Hilarious mixed bag. Some have been like, “Oh my gosh, why would we be associated with this?” Most people are just like, “We know Arun, he does this.” And getting more eyeballs on the work that I do in music and in tech is always great.