Drew Houston forgot his USB drive on a bus from Boston to New York. So he started building the thing that would make USB drives obsolete, right there on the bus.

The story: Dropbox

Who they were. Drew Houston, a recent MIT grad, building a file sync tool that would make your files magically available everywhere. The problem was deeply felt by anyone who’d ever emailed themselves a document or named a file “proposal v2 good revised NEW 11-15-06.doc”. The audience was developers and tech-savvy early adopters who already sensed the answer had to exist.

The channel. Hacker News, in April 2007, before Hacker News was even called Hacker News. It was called Startup News.

The move. Houston had a working prototype but not a finished product. Rather than wait, he recorded a rough three-minute screencast showing how it worked and posted it with the title “My YC app: Dropbox. Throw away your USB drive.” He was applying for Y Combinator and wanted feedback. He got it, starting with a comment telling him not to bother.

Original Screencast

The original HN post, April 4–5, 2007. Still live at news.ycombinator.com/item?id=8863

The very first reply, from a user called BrandonM, said Dropbox was pointless. You could already build the same thing yourself: get an FTP account, mount it locally with curlftpfs, then run SVN or CVS on top of it for version history. Why would anyone need a product for something an engineer could wire up with tools that already existed.

Houston’s reply is the whole lesson. He didn’t argue the engineering. He pointed out who the DIY version was actually for. Online drives felt awful to use because Windows and Mac apps assumed the disk was local. Every file open, every save, every icon lookup turned into a round trip to a server, and on a slow connection that meant your screen locking up for minutes over a file a few hundred kilobytes in size. Dropbox synced a folder that lived on your machine in the background, so it worked the same whether you were online or on a plane with no signal at all. The FTP and SVN combo was a real fix, but only for someone willing to assemble it. Most people emailing themselves attachments were never going to do that. They just wanted their files to be there.

That’s the difference between solving a problem and solving it for the people who actually have it. The engineers on that thread already had a workaround. They were not the customer. The customer was everyone who didn’t know what curlftpfs was and never would, and the win was making something that complicated disappear behind one folder that just worked.

That thread mattered for another reason too. The right people were there even if some of them were wrong about who needed this. It lit up with technical feedback from developers who wanted this to exist. That feedback shaped the product.

That same post attracted Arash Ferdowsi. He saw the demo, left MIT’s Masters program, and became Dropbox’s co-founder and CTO. Drew put one thing in front of the right people, and the right person showed up.

That got them into YC Summer 2007 and gave them a co-founder.

Then came the second move. In March 2008, Houston made another video for the private beta launch. He posted it on Digg under the headline “Google Drive killer coming from MIT Startup.” But here is what most people miss: he packed about a dozen Easter eggs into the video, references to Tay Zonday and Chocolate Rain, nods to Office Space, XKCD comics. Things the Digg and Reddit crowd would catch and grin at. The video picked up 12,000 Diggs. The beta waitlist jumped from 5,000 to 75,000 in one day.

Two moves. Same principle both times: go to the exact community that already feels the pain, and speak their language.

What it cost. One screencast, a YC application, and enough homework on the Digg community to know what they found funny.

The lesson. Show the magic before the product is finished. If you know a specific community that already feels your problem, you don’t need a product launch, you need one honest demo in the right room. And when the smartest people in that room tell you the problem is already solved, look at who they mean by “you.” An engineer with an FTP account and curlftpfs was never your customer. The person who just wants their file to be there was.

What you can steal

Your potential users are probably gathering somewhere right now, talking about exactly the problem you solve. A forum, a Slack, a subreddit, a corner of Hacker News. You don’t need a finished product to show them something real.

Watch who tells you not to bother. If it’s someone who can already patch together their own fix with tools you’d need a manual to explain, that’s not your customer talking, that’s someone who was never going to feel the pain the way your real user does. The simplest problems are often the ones nobody with technical skill takes seriously, because they can solve it themselves in ten minutes. That gap between “I can hack this together” and “I just want this to work” is where a lot of real businesses hide.

Where is the one community that already feels your pain? And what would you put in your version of the video to make them feel like you made it specifically for them?

Got your own first 5 story? Hit reply and tell me how you landed your earliest customers. The channel, the message, what you did. I feature real founders here and yours could be next. Or submit it here

And if this was useful, forward it to a builder who is stuck staring at an empty dashboard.

Stay scrappy,
Gary

I didn’t think much of it at the time. Then I started digging into how Coinbase got its first users in 2012 and realised VALR had run almost the exact same play, just 12 years later.

Brian Armstrong launched Coinbase in spring 2012 with no co-founder, a raw product, and a company name he hadn’t even finalised. Major crypto exchanges were being hacked or shutting down. He got out first.

The story: Coinbase

Who they were. Armstrong was a former fraud-prevention engineer at Airbnb, building what he described as “the easiest way to get started with Bitcoin.” He had posted a self-described “hail mary” on Hacker News looking for a co-founder with an “insane” work ethic who was up for “super fucking hard” work. The post failed. He went through YC that summer alone. The company was still called Bitbank. The site warned users not to “use any coins with this website that you are unwilling to lose.”

The channel. Not TechCrunch. Not a press tour. Armstrong posted on Tumblr (where Coinbase’s blog lived until 2016), Hacker News, and Reddit. The places where crypto people actually spent time.

The move. Three plays, each one removing a layer of friction.

First, he posted on r/Bitcoin offering 0.10 BTC to anyone who emailed in feedback on the site. The post has since been deleted, but it pulled real users in and got him real feedback at the same time.

Second, the team sent cold emails with Bitcoin already in them. Garry Tan (now president of YCombinator) recalled getting one when the company was still called Bitbank: 0.05 BTC sitting there, waiting. All you had to do was create an account to claim it. Claiming it meant adding a phone number, an email, and setting up a full profile. By the time you were done, you were already using the product.

Third, early users got a referral link: 0.10 BTC to the friend who signed up, and 0.10 BTC back to the person who sent the link. Bitcoin was trading at around $10 at the time. Total cost of acquisition for both sides of the referral: $2 per verified account. Kevin Rose tweeted about Coinbase in August 2012 and got 29 reposts overnight.

What it cost. A few dollars per user in BTC at the time. The $2 CAC per verified account looks almost embarrassing now. Coinbase’s average net revenue from a transacting user would eventually be $35 or more per month.

The lesson. Go where your people already are, then remove every reason not to take the first step. Armstrong did not ask people to believe in crypto. He put crypto in their hands before they even had to decide if they were interested.

What you can steal

Find the one forum, subreddit, or community where your exact customer is already talking about the problem you solve. Post there first, before you go anywhere bigger. Then work out the smallest thing you can give them to get them into the product today, not next week.

What would it cost you to hand one potential user something real before they’ve even decided they want your product?

Got your own first 5 story? Hit reply and tell me how you landed your earliest customers. The channel, the message, what you did. I feature real founders here and yours could be next. Or submit it here

And if this was useful, forward it to a builder who is stuck staring at an empty dashboard.

If you want a framework for tracking which channels are actually converting, the AARRR template is free and worth keeping alongside whatever you’re building.

Stay scrappy,
Gary

Brian Chesky and Joe Gebbia were broke. Credit cards maxed. Losing weight. The idea that people would rent rooms in strangers’ homes was not exactly catching on.

Then the 2008 Democratic National Convention came to Denver.

The story: Airbnb

Who they were. Brian Chesky and Joe Gebbia, two RISD-trained designers who met at art school and moved to San Francisco together. They had an idea: people could rent out air mattresses in their homes to conference-goers when hotels were full. The first test came in October 2007, during an industrial design conference in their own apartment. Three people stayed. It worked, sort of. But the product was not growing.

The channel. Press, from the bottom up. And then, an election.

The move. In August 2008, Chesky read that Denver had only around 28,000 hotel rooms to accommodate 80,000 DNC convention attendees. He saw the gap. He and Gebbia launched the official version of the site, renamed Airbnb, timed to the convention, and blasted emails to bloggers in Denver with their story. The framing was direct: Obama supporters could host other Obama supporters from across the country. They made themselves part of the story, not a tech product pitching a concept.

airbedandbreakfast.com, March 2008. The site before the rename — pink and blue, air mattress icons, “Share housing. Save money. Meet cool people.”

The first counterintuitive move was picking the smallest bloggers. Big press was not coming to two unknown founders with a weird idea. So they went small on purpose, collecting tiny write-ups that added up to social proof. That social proof opened bigger doors. Eventually NBC and CBS came to them.

TechCrunch, October 9, 2008. The article that ran when Chesky sent cereal boxes to tech bloggers.

The convention generated 80 bookings. Not nothing, but not enough to survive on. Chesky later described the situation clearly: “Joe and I are broke. We’re losing weight, and I didn’t have a lot of weight to lose. At this point I am $25,000 in credit card debt.”

With the election in full swing and the company still close to dead, they came up with their strangest move. Two RISD designers making a tech startup. Why not design something?

They created collectible election cereal. Obama O’s, “The Breakfast of Change,” filled with repackaged Honey O’s. Cap’n McCain’s, “A Maverick in Every Bite,” filled with repackaged Quaker Puffs. They printed poster board, folded it, and hot-glued each box themselves. A thousand boxes total, 500 of each. They sold them for $40 a box, mainly by sending boxes to well-known tech bloggers hoping for coverage. TechCrunch covered it on October 9, 2008. They raised around $40,000.

That $40,000 kept the lights on long enough to apply to Y Combinator. When they walked into the YC interview and handed Paul Graham two cereal boxes, his response was: “Wow, you guys are like cockroaches. You just won’t die.” They were accepted into the Winter 2009 batch.

During YC, Graham asked where the demand was. The answer was New York. He told Chesky to go there. Chesky and Gebbia flew to NYC with a rented camera and knocked on their hosts’ doors, photographing listings themselves. That fix, better photos, roughly doubled weekly revenue. They hit ramen profitability on February 22, 2009. Chesky emailed Graham to tell him. Graham’s reply: “I assume you know what you’ve now set yourself up for next week.” Chesky answered in seven words: “We are not going to slow down.”

What it cost. Two maxed credit cards, a rented camera, some hot glue, and enough creativity to do the embarrassing things that actually work.

The lesson. Manufacture a reason to act now, not someday. Find the moment people are already looking at, and make your thing part of it. When survival depends on it, there is no move too small or too strange.

What you can steal

Is there a real event happening in the next few weeks that your target user is already paying attention to? Not a fake angle, a genuine one where your thing actually solves a real problem for them in that moment. The DNC was not a gimmick for Airbnb. There genuinely were 80,000 people looking for rooms.

And when you are out of runway, the move is whatever it takes to buy another month. What is your version of the cereal box?

Got your own first 5 story? Hit reply and tell me how you landed your earliest customers. The channel, the message, what you did. I feature real founders here and yours could be next. Or submit it here

And if this was useful, forward it to a builder who is stuck staring at an empty dashboard.

I put everything I know about going from zero to first customer into the Stay Scrappy Founder’s Guide — worth a look if you’re at that stage.

Stay scrappy,
Gary

Most founders are too polite to win.

They build something, show it to a friend, and ask “would you maybe want to try it sometime?” The friend says yes to be nice, then never does. The Collison brothers refused to play that game, and it is a big reason Stripe exists.

The story: Stripe

Who they were. Patrick and John Collison, building a dead-simple way for developers to accept payments online. Their customer was not a CFO or a banker. It was the developer who felt the pain of clunky payment systems every single day.

The channel. Their own network and the YC community. Friends, then friends of friends.

The move. Their very first user was a friend, Ross Boucher, who needed a payments system while they happened to be building one. But here is the part worth stealing. When anyone said they would try it, the brothers did not send a link and hope. Paul Graham named the technique the “Collison installation”. They would say “right then, give me your laptop” and set the person up on the spot, then and there.

That one move killed the gap between interest and action. No forgetting, no putting it off. They watched exactly where people got confused, fixed it, and turned each early user into someone who told their friends.

What it cost. Nothing but hustle and the willingness to be a little pushy in a helpful way.

The lesson. Close the gap between yes and done. When someone shows interest, help them use it immediately, while you are sitting right there. Interest fades in hours. An installed product does not.

What you can steal

When someone says “yeah I’d love to try it”, do not send a link. Get them using your product while you are still in the room or on the call. Interest fades in hours. An installed product does not.

What would it take to onboard your next interested person on the spot, today, instead of adding them to a list?

Got your own first 5 story? Hit the button below and tell me how you landed your earliest customers. The channel, the message, what you did. I feature real founders here and yours could be next.

Tell us your story

And if this was useful, forward it to a builder who is stuck staring at an empty dashboard.

Stay scrappy 🤙🏼
Gary

Vibecoding. Agentic apps. You describe the thing, something builds it, you ship by lunch. This chart people are sharing says the quiet part out loud: releases climbed something like 80%. Usage didn’t move. Reviews actually slipped.

So we’re not blocked on building anymore. We’re blocked on being chosen.

It reminds me of what happens when a town opens fifty new coffee shops in one month. The beans are fine. The machines work. But there are only so many people walking down the street, and most of them already have a cup.

The first five customers are like that. Not your logo. Not your launch tweet. Five humans who’d be annoyed if you disappeared tomorrow. That tiny group sets the angle everything else follows from.

I got curious about how the good ones did it back when building still cost you something. Years ago, when I traveled a lot, I’d fill the hours with founder stories. How I Built This. Masters of Scale. Whatever I could find. Not to learn a framework. Just to remember that someone else had been stuck in a hotel room wondering if anyone would ever care.

It worked. I’d land, open the laptop, and keep pushing.

I’ve been collecting those stories ever since. A swipe file, basically. The moves that got the first few customers, not the IPO speech. I figured if they helped me on a bad Tuesday, they might help someone else too.

That’s First 5. One story a week on Stay Scrappy. DoorDash first (PDF menus, campus flyers, founders in the car). Then Stripe, Airbnb, Buffer, Dropbox, and the rest of the pile on my desk.

It’s not a course. I don’t have a framework to sell you. Just stories worth reading on a slow morning, when you need a nudge to do the unglamorous thing instead of tweaking the landing page again.

If you’ve crossed $1k MRR and remember how you got your first few, I’d love to hear it. Drop your story here

More soon …

Gary - Keep Shipping 🚀

I started First 5 (new section in my newsletter) because I kept watching the same heartbreak play out.

A founder spends months building. The product is good. They ship it… and then silence. No customers. No idea where to find them. In the age of AI, anyone can build — the hard part was never the building. It’s getting those first few humans to care.

That’s the whole mission here: help founders create real products and find real customers. Not vanity signups. Not “we’ll go viral.” Real people who actually want the thing.

So every issue of First 5 does one thing: I break down exactly how one company got their first handful of customers. Where they found them. What they actually said. What it cost. And the one lesson you can steal today.

No fluff. If it didn’t really happen, it’s not in here.

Let’s kick off with one that’ll make you feel a lot better about your scrappy little MVP.

The story: DoorDash

Who they were: Four Stanford students who wanted to test one question — do people actually want food delivered from local restaurants?

The channel: Their own campus. Offline. On foot.

The move:

Before DoorDash was DoorDash, it was a webpage called paloaltodelivery.com. That’s it. A handful of restaurant menus they’d literally PDF’d and slapped online. No app. No drivers. No backend. No company.

Then they printed a stack of flyers offering delivery for $6, and plastered them all over Stanford.

They weren’t trying to “launch.” They were trying to find out if a single person would click “order.” The orders came in — and then they figured out the delivery. Tony Xu and the team did the driving themselves.

What it cost: A cheap webpage and some printed paper. Hours, not dollars.

The lesson: Test the demand before you build the machine. They didn’t build an app and pray. They faked the smallest possible version, put it where their customers physically were, and let real orders tell them the truth.

Your turn

Here’s the uncomfortable question: what’s the flyer-and-PDF version of your idea?

Not the polished app. Not the roadmap. The scrappiest possible thing you could put in front of 20 real people this week to see if they bite. If DoorDash could fake it with a PDF, your “not ready yet” excuse just got a lot weaker.

That’s the First 5 way — ship something small, put it where your people are, and let real customers pull you forward.

Got your own first-5 story? Hit reply and tell me how you landed your earliest customers — the channel, the message, the move. I feature real founders here, and yours might be next.

Tell us your story

And if this lit a fire, forward it to a builder who’s stuck staring at an empty dashboard. That’s exactly who I wrote it for.

Stay scrappy,
Gary