Training the Idea Muscle

Riley describes himself simply as a guy who likes to do things he finds fun. But to the New York Times, he's known as "The Tech Jester Who Pranks San Francisco". He's responsible for projects like:

• Find My Parking Cops: Find My Friends but it tracks San Francisco parking cops and all the tickets they give out
• LooksMapping: Ranking restaurants based on how hot their customers are
• Fast Food Index: Showing price disparities of fast food across the country to determine an area's cost of living^[1]
• Bop Spotter: A play on ShotSpotter, which helps the police listen for gunshots; this is a box on a telephone pole that Shazams music 24/7
• Maybe 50+ others that make me think "How does he come up with this sh*t?"

But before any of his projects went mega viral, before he started getting massive Twitter payouts and job offers from the top AI companies in San Francisco, before he had an army of reporters pleading to write about anything he does — he was just a kid dreaming of building B2B SaaS apps.

I met him five years ago. My first impression of him, after he showed me his fake Twitter profile that got a blue checkmark by exploiting their verification system's leniency for political candidates, was "Wow, this guy's weird. I like him."

Years later, when he showed me a fake street sign he put up outside the Louis Vuitton store, my impression was "Wow, this guy's probably going to jail someday."

From an early age, he was focused on two things: securing the bag and stirring the pot.

At 13, he almost took an NPR radio show off air by getting access to their admin dashboard over an unsecured WiFi network. At 15, he got his first job as a dishwasher and parlayed his salary into becoming an online loan shark for desperate redditors. At 19, he antagonized a foreign government by noticing the domain for the website in Qatar's Twitter bio had expired, so he bought it himself and redirected it to an anti-Qatar tweet. This forced their federal government to revoke the domain entirely (since they control the .qa TLD).

His first internet money came at age 16 when he made Routeshuffle - a site that generates random running routes. All of his software is pretty personal, and he's been running every day since high school, so he built this to solve a problem he had and other people ended up liking it too. His first internship was at MSCHF, a company that runs internet pranks at scale. They don't normally hire interns, but he got a permit from city hall to put a plastic newspaper box on the sidewalk in front of their office with his resume inside. They emailed him back pretty quickly after that.

Riley's not much of a job-haver at heart though. He's a guy that has 50+ ideas on his wall in backlog at any given point, so even when he's working, there's always some stuff happening on the side. It was inevitable he'd end up doing his own thing professionally at some point, and in 2023, he moved from NYC to San Francisco with his best friend to start an AI for spreadsheets company. With just two people, they made a product that generated over a million dollars per year. After that year of hard work, they decided to stop working towards growing the startup and used the proceeds to just cover their living expenses while they focused on other things.

Let that sink in. He has so much going on that starting a million-dollar company in a year wasn't compelling enough for him to keep working on it. Nowadays, he scrapes data for AI companies for a living and learned everything he needed from all the fun data projects he's been doing over the years. No college degree and no relevant work experience, yet he followed his curiosity and now the money follows him.

All ideas are good ideas

Riley's biggest inspiration is this guy who makes $200k/year writing music that you've probably never heard of: Matt Farley. Matt's been making about 50 songs a day for the past 12 years, but most of those songs barely get any streams. He's written a book, produced short films, all of which have been seen by maybe a few hundred people total. But when you add up the impressions of his entire 20,000-song body of work, it starts to make sense why he makes that much money.

When asked about how he makes so much stuff, he said:

"If you reject your own ideas, then the part of the brain that comes up with ideas is going to stop. You just do it and do it and do it, and you sort it out later."

Riley owns 4 copies of his book, and he gave me one in response to my frequent complaints about my own creative process. We had a conversation the other day:

Riley: "Writing must be hard. I heard this quote that said, 'The only time you're happy as a writer is when you're finished.'"

Aadil: "So true. I feel like everything I write is bad all the way through until it's finally published. But I guess everything is like that. You probably feel the same way for all your projects too."

R: "Hmm. Not really. I'm pretty happy all the way through."

A: "Huh? How's that possible?"

R: "I'm not sure how it could be anything else. I only work on things I think are fun."

A: "But what if you attempt something you're not skilled enough to do yet? Or you finish something but you don't think it's good enough?"

R: "I kind of just think everything I work on is good. I don't think I've ever done anything I'm not good enough to do because I get good at the thing while doing it. Looking back now, I think maybe there's things I could have done better. But I never really think about going back to a project past a few weeks because there's so much other stuff I want to make."

After years of doing stuff and sorting it out later, it's clear that Riley's ideas are just better. He's a huge data nerd at heart, so usually when I ask him how he came up with something, he'll say something like, "well, I just happened to be scraping [insert highly protected obscure company or government data here]."

At one point when he was telling me about everything he wants to work on next, I decided to play a game with myself. Every time he told me about whatever data source he scraped, I'd make a guess as to what project he would be making with it. Every single idea Riley explained to me was 10 times better than any of my guesses.

The thing is, it's not like I couldn't have come up with any of those good ideas myself. They're fairly obvious after Riley mentions them. Same goes for the data scraping. It sounds hard for the average person, but one of the many skilled software engineers in SF can probably do what Riley does from a technical standpoint without too much trouble^[2].

Ideas are all around. The problem is, most people don't act on them. If you always reject your own ideas for not being good enough, or being impractical, or think you're not good enough to make them, or that you don't have enough time, or any other reason, it's like skipping brain day at the gym. You have to get what's in your brain out of it. Making your ideas a reality again and again is the only way to generate better ones over time.

No such thing as an impossible idea

Riley has this odd sort of gravity around him that makes you want to help with whatever he's doing any way you can. He's a borderline local SF celebrity at this point, but carries himself as anything but. You look at him and you think, "If he can do it, so can I. But doing it alone is hard so I'll just go along with him." I suspect it's that people just like being part of things and supporting the underdog, so Riley's serial thing-do-ing with no ulterior motive and no ego is magnetic.

One of his most elaborate pranks was Mehran's Steakhouse. It initially started as a joke when his old roommate Danielle listed their group house as a steakhouse on Google Maps. The joke grew, getting over 100 detailed 5-star reviews from other friends pretending they'd eaten there. Being the only perfect 5-star steakhouse in NYC gave them a lot of attention, and after shooing away visitors from a restaurant that didn't exist for two years, they thought "Wouldn't it be funny if it actually did?"

That's how a lot of Riley's ideas start. "Wouldn't it be funny to piss off the Qatari government? Or make a Gmail clone called Jmail with all the Epstein emails in it? Or Find My Friends but it tracks parking cops?"

When his friend Mehran started worrying about a project going wrong, he quickly interjected:

"But doesn't everything always just work out? Like sure, it might suck in the moment, but everything's always fine. Somehow every moment in life always magically works out in the long run. I don't think I could name one time where everything went completely wrong, because if it did I wouldn't be here right now."

There's a million ways Mehran's Steakhouse could have gone wrong.

It was near impossible to find a venue in their budget, but one of their friends connected them to a billionaire who gave them a warehouse for free. They had to serve wine but New York City requires liquor to be purchased only through authorized distributors, even if you get a license. Riley was about to break the law by buying 40 bottles from Costco when his friend said he knew a guy then called up one of the biggest distributors in the city and they took care of it. There wasn't enough stove space to cook for everyone so they bought a bunch of toaster ovens to make the appetizers. They found their steak supplier off of Reddit and didn't get a chance to try it before buying 100 pounds for incredibly cheap, and everything ended up tasting fine. They had no staff but 60 of their friends came through to help. They flew across the country to help cook, wait tables, usher guests, stand in the rain with signs that made it look like Drake was inside, fake a marriage proposal, put out fires, and everything else that goes into running a restaurant.

To everyone that helped out, it felt like play. People were grateful they could be a part of it. When asked why she did it, our friend Anson said, "People are terminally online and constantly watching other people live lives. When people, like Riley and Mehran, are high-agency, it attracts people like moths."

Riley's never tried to be a leader or an inspiration, and is fairly soft-spoken when you meet him. He's probably the exact opposite of Donald Trump, yet still always seems to have people willing to follow him into battle. It probably helps that the battles he picks are fairly silly and spread a lot of joy and confusion, but it's undeniable the pull he and his ideas have on people. I sometimes wonder if he'll secretly start a cult some day, because he probably has the gravitas to do so.

The closest he's ever gotten is with the Pursuit Scavenger Hunt, which got thousands of people in San Francisco to do basically whatever Riley and his friends wanted all in the name of fun little adventures. No one even knew or questioned who was behind it for a while. All people saw was a figurehead being a character called "Percy" that Riley and Danielle made up, and everyone would use fake names when interacting with hunters.

It was taken a bit too far, and now has a cult-like following that still chats every other day in a fan-made Discord. Again, it took months of work from him and about 20 of his friends to design clues, convince local businesses to let them put 'art installations' everywhere, and run a finale event for hundreds of people^[3].

After the first Pursuit, the second one was mainly organized by his friends Danielle and Athena. Almost everyone who made a clue for the first one came back to do a second one, including me. I did things I never thought I could do or had time for, like convincing 4 local businesses to let me put silly items in their stores for thousands of people to flood and install hidden cameras so I could watch them.

I had a full-time job, yet I made a custom board game, designed fake posters, 3D printed a piggy bank and filled it with hundreds of gold coins, all for absolutely zero ROI other than the fact that I thought it was fun.

He's the most persuasive person I've met who doesn't try to persuade anyone. I don't even think he expects anyone to ever help him, it's just the ideas he chooses to do are so interesting that no one ever thinks to question if he can actually make them real. He just looks like he's having so much fun that you have to join him. You don't even care about credit, but after making it happen, you suddenly leave with the urge to make more things happen.

It's only after being part of one of his schemes or doing your own that you realize why Riley does it, even though he tells you exactly why when you first meet him, and that you can do it too.

"I dunno. I thought it would be funny."

You can find Riley here. DM him and tell him I sent you.

Notes

1. [1]

   Which was once used in a Harvard Business School lecture

2. [2]

   With a little help from Riley, I was able to reverse engineer the CVS API myself and get data on what prescription drugs were available at every pharmacy in America. Which gave Riley the idea to make a funny site that displays something like "How much Viagra is your city taking right now?"

3. [3]

   For which, again, they got the venue for free. People just loved what they were doing.