Brian Armstrong recounts an early college startup: a tutoring marketplace he and a roommate built to match university students with high-schoolers. They initially tried to process payments and take roughly a 10% fee, but users preferred paying tutors directly so the platform hindered repeat local in-person business. Armstrong pivoted the site into a passive directory with optional $10/month featured listings and ad support; after he stopped actively managing it, traffic doubled year-over-year for several years and the site was later acquired for about $2 million. The core lesson he emphasizes: stop trying to extract value up-front and focus on creating value first.
Questions this video answers
$60 per hour
Approximately 10% fee
$10 per month
About $2 million (described as 'maybe like $2 million')
Chapters
As a college student, my roommates and I were always trying to think about how to make extra money. And one of the upper classmen, I remember, he told me, you know, I'm tutoring this high school kid and they're paying me $60 an hour. I was like, wow, $60 an hour. It was like 3 or 4x what you could make at these other on campus jobs. So I decided to try doing it myself. I started tutoring high school kids just in like math and science and things like that. And it paid really well. And so my roommate and I at the time, we were starting to just brainstorm, like, why don't we start a little tutoring company and help high school kids and their parents match with basically university students at the university where I was going to school. And so we got that going. We got maybe 10, 20 of our fellow students kind of connected in. And then we said, all right, let's make a website for this to connect even more people, maybe to try to expand it to other schools. We didn't really know this at the time, but we were kind of making an online marketplace like Airbnb for. But. But for tutoring. We were trying to take like a 10% fee by matching these people. And we were basically trying to do all the payments through our website. And what would happen often is they would meet the tutor if. And they'd do the initially the first pay, but then afterwards they'd start paying them under the table. And so I realized at a certain point we were basically just getting in the way. They wanted us to just match them, but they didn't want us to be the whole billing apparatus. It was a much more of like a local repeat business, in person business. And so for years and years I struggled with that. So I eventually realized, this thing isn't working. I need to go get a quote, unquote, real job. I was about to shut down the tutoring site and I was like feeling a lot of pain about that because I was like, well, I don't know, there are still like 5, 10,000 people every month who are kind of looking at this thing and using it. So I was like, what if I were just to put everything on autopilot? You know, we're not going to be involved in any of the payments. There's no customer support. This is literally just going to be a directory, like a tutoring directory, and you can contact these tutors, you can pay them however you want. And I'm just going to try to make it like a free thing, maybe I'll put up some ads. And so I basically had like a week before I was starting my new job. I got rid of all the payments. I messaged all the people using it. I was like, you can pay now people directly. Then I did one more thing at the last hour, which is I said, if you want to have a featured profile as a tutor with a little featured badge and come up first in search results, then you can just pay $10 a month. And that was it. And I basically stopped looking at the website and I went to go focus on my new job. And every year thereafter, the site doubled after I made that change. Um, and so basically, I guess the lesson was stop trying to extract value and start trying to create more value later. Later somebody ended up acquiring it for maybe like $2 million or something. It was like a seven or eight year base hit outcome where for years, you know, five, six years, I was struggling to get anything to work.