Unglamorous
Examples of the small, embarrassing work behind very large companies.
Patrick Collison keeps a list called Fast, about ambitious things that got done quickly. This is the other half. Before the speed, the scale and the press, nearly every founder we admire spent time doing something that looked small: shilling their own product, sending DMs nobody answered, pretending to be their own users.
Everyone’s willing to work hard. Almost nobody’s willing to look small. These people were.
1. Jeff Yan, Hyperliquid (Oct 2023)
Tweeted: “Super juicy BTC funding arb available in 7 figs on @HyperliquidX. Almost 400% annualized to short, while CEXs are flat for an easy hedge. Also a record volume day for BTC on the platform!”
A former high-frequency trader and physics olympiad medalist, publicly shilling trading opportunities like an active trader trying to bootstrap liquidity. Most exchange founders stop doing this the moment they have any traction. Hyperliquid is now the largest onchain perps exchange.
2. Brian Armstrong, Coinbase (2012)
Posted on Hacker News from a throwaway account called “tempaccount987”: “Apply with me to YC in the next 3 days and change the world.” After launch, he offered 0.1 BTC on r/Bitcoin to anyone who emailed him feedback.
An Airbnb engineer hid his own name to ask strangers to co-found with him, then paid people to tell him what was wrong with his product.
3. Michael Truell & Aman Sanger, Cursor (2022–23)
Truell DM’d huge numbers of people asking for help, feedback, or to join. When Cursor blew up, people started falling out of the woodwork posting his old DMs. Truell replied to users publicly too helping them out with the product.
Meanwhile, while their earlier ideas were failing, a co-founder explicitly set out to try to gain a lot of followers by reading every AI paper and tweeting about them. He became, in Truell’s words, a niche SF micro-celebrity, then used that audience to launch Cursor.
The CEO of a company SpaceX bought for $60B, sitting unread in people’s inboxes, while his co-founder deliberately farmed followers because the company had no distribution.
Lieberman · “DM me bugs” · “Falling out of the woodwork” · Truell at YC
4. Chad Hurley, Steve Chen & Jawed Karim, YouTube (2005)
After five days with zero uploads to their video dating site, they posted Craigslist ads in LA and Las Vegas offering women $20 to upload a video. Nobody took it.
The founders of the world’s biggest video platform couldn’t pay strangers to upload a single video.
5. Alon, pump.fun (2023–24)
“A few months, 3,000+ cold DMs, and hundreds of PRs later, it was finally starting to get traction.” That came after years of “chewing glass” on NFTs, SocialFi and DeFi.
Thousands of people got a DM from a pseudonymous dev and chose whether to reply. Most didn’t. Pump is the biggest launchpad in crypto right now.
6. Steve Huffman & Alexis Ohanian, Reddit (2005)
“In the beginning Alexis and I submitted all the content,” using fake accounts. They built a tool that let them choose the username on every post.
The front page of the internet started as two founders pretending to be a crowd.
7. Ben Silbermann, Pinterest (2010)
“I used to walk by the Apple store on the way home. I’d go in and change all the computers to say Pinterest.” He also sat in coffee shops asking strangers to try it.
A future public-company CEO doing what a teenager does with their own website.
8. Sara Blakely, Spanx (2000)
Felt she was losing a Neiman Marcus buyer mid-pitch and asked, “Will you come with me to the bathroom?” Then she modeled her white pants without and with Spanx.
A future billionaire’s most important pitch happened in a restroom.
9. Des Traynor, Intercom (2011)
Sent “approximately 100 or so emails… every day,” each with a custom screenshot made for that prospect. “One morning I got up at 4am and drove to work to give a webinar to nine folks in India.”
A co-founder lost a night’s sleep to demo software to fewer people than fit around a dinner table.
10. Eric Yuan, Zoom (2011–15)
“During the early stages of Zoom, I personally emailed every customer who cancelled.” One customer accused him of sending auto-generated emails “impersonating” the CEO.
A former Cisco VP chasing every churned user, so personally that they didn’t believe it was him.
11. Mert Mumtaz, Helius (2021–22)
By his own description, he built his name as a “reply guy,” correcting Solana FUD in other people’s replies.
The CEO of Solana’s biggest infra company got his start arguing in the comments.
12. Dan Romero, Farcaster (2022–23)
Read through Twitter DMs and handed out invites one at a time, sometimes over 1:1 Zoom calls. The official way to join was “DM @dwr.” I got mine by just pinging him.
A former Coinbase executive working the door of his own social network like a bouncer.
13. Max Junestrand, Legora (2023)
Cold-emailed lawyers asking for lunch to learn about their work: “We offered to pay their hourly fee to have lunch with us.” They ended up in a law-firm conference room “with no real windows where the AC would turn off at about 5:00 PM.”
Paying strangers so you could ask them questions, then working from their office itself.
14. Melanie Perkins, Canva (2011–13)
After more than 100 investor rejections, she learned kitesurfing, a sport that terrified her, because investor Bill Tai held his networking events at kitesurfing retreats.
15. Wade Foster, Zapier (2011)
Found Andrew Warner’s months-old Stack Exchange question about connecting PayPal to Highrise and emailed him, despite being nervous about rejection. Warner became Zapier’s first customer.
Answering strangers’ old questions on a public forum as a way to get customers.
16. Whitney Wolfe, Tinder (2012)
Gave presentations at sorority chapters and got everyone in the room to install the app, then went to the matching fraternities. Tinder went from about 5,000 to about 15,000 users on that one trip.
A co-founder working campus promo like a promoter.
17. Tony Xu & co-founders, DoorDash (2013)
PaloAltoDelivery.com was a static page, some PDF menus and a Google Voice number that rang the founders’ phones. They placed the orders and delivered the food themselves.
Stanford students working as delivery drivers.
18. Apoorva Mehta, Instacart (2012)
No grocery store would partner with them, so they bought one of every item and photographed it all to build the catalog.
Founders as grocery shoppers and product photographers.
19. Patrick & John Collison, Stripe (2010)
The “Collison installation”: when someone said yes, they’d say “give me your laptop” and set Stripe up on the spot.
Founders doing IT support in person, from the people who wrote Fast.
20. Ankit Garg & Chaitanya Ramalingegowda, Wakefit (2016)
“We visited homes for our first 100 deliveries, and did video interviews for feedback.” They delivered the mattresses in their own cars.
Founders as delivery men.
21. Pebble (2012)
“The Pebbles assembled the first several hundred watches themselves.”
Founders working on their own factory line.