"Ask me the questions you're too embarrased to ask," Ryan told the dozen or so of us crowded on couches and chairs in the Mission house living room last Wednesday. The CEO of alternate early education company Primer, Ryan's Q&A was led by Brennan, our Daly City house organizer and an engineer at Synthesis Schools. An hour -- only halfway, it would turn out -- into his visit, I realized that it was one of the most lucid and impactful conversations I'd been a part of recently, and whipped out a tablet to take notes. They're too coarse, and it's been too much time now, to give a play-by-play of the night, but here are a few big ideas and takeaways that have stuck with me.
Primer is a "home for ambitious kids," as Ryan puts it: a platform providing resources and community (with audio-only live rooms) for 8-14yos to pursue whatever they're passionate about.
The emphasis here is on what they're passionate about. The program is opinonatedly neutral about what paths are good ones for kids to take: "if you want to open a cafe in your neighborhood, we want Primer to be the best place for you to pick up the relevant skills. We don't push kids to become software engineers," Ryan said.
When guidance is provided, which it inevitably has to be, it's done so without losing the student-centric ethos. Primer's office has a big "take it seriously" sign in it, Ryan tells us. When someone spent hours a day for months on end making stickers for a competition, the Primer team approached the kid conversationally: "do you think this is a productive use of your time?"
The benefits of this approach extend beyond kids' love of the platform. Ryan told us about one student in speech therapy who improved more in six months after starting Primer than in years before, according to their therapist. Ryan hypothesized that this is because they were properly motivated to speak with their peers in the program, and to feel passionate about learning in general.
Primer aims to "rewire" kids to think that being interesting and unique is cool, overriding standard conformist social/cultural dynamics. This can come into conflict with Primer's business strategy: parents are ultimately the ones paying for the program, and appealing to parents must be balanced with appealing to students, while prioritizing students at the end of the day. About one in fifteen signups right now are student- as opposed to parent-driven at the moment, a ratio Ryan says would ideally increase, as student-driven growth would be necessary for Primer to increase its impact without compromising on what it delivers to students.
On the subject of alternative education, Ryan, like many successful founders, expressed his support of opting or dropping out of school. Having been homeschooled, then attending an untraditional high school, then a large public school, he gave an even stronger indictment: "other than parental pressure, there's no compelling reason to go to college."
His reasoning is that learning can happen much faster outside of school for most people. While he believes this is true in or outside of startups, he emphasizes that being a part of startups at very early stages offers an extremely steep learning trajectory.
There's a common idea that being #2 in a startup is a terrible deal, because founders benefit (financially and reputationally) hugely more for a similar amount of investment -- an experience Ryan went through firsthand as Gumroad founder Sahil Lavingia's first employee. Ryan disagrees with the negative assessment, though, emphasizing that the learning environment makes the opportunity far more valuable than others that may have better direct payoffs.
Being a CEO also comes with increased reputational risk, Ryan shared, a factor significant enough that he chose to turn down the position when offered to him at one point in his career.
Positions aside, Ryan's strategy for maximizing learning and opportunities is to attempt to become the best in the world at something. Other than in regards to interpersonal skills, your weaknesses don't really matter, Ryan says: just find a way to be useful and a reason to be known.
For Ryan, this thing was making deals for Gumroad. "I wanted to become a deal-making machine, flying 30,000 miles a year," Ryan remembers; and he succeeded, at least enough to drive Gumroad's early skyrocketing growth and building himself a reputation that carried to future projects.
It's a refreshingly direct and intuitive take on self-improvement, at least for me (I suspect things like this vary by personality type). The pursuit of excellence, the satisfaction that comes from the process and the personal value increase that comes with each milestone hit, is something I understand deeply and well.
Where am I pursuing excellence in? At the moment, I think it's building: bashing out software and side projects more effectively than nearly anyone else around me. My design-frontend-fullstack competency stack is already fairly exceptional: it's allowed me to get some amazing jobs and contracts, and insert myself into high-standards teams and environments I'd otherwise struggle to access.
There are great role models in this respect, too: Linus Lee and Jacky Zhao are two people I look up to immensely for their side projects, and the thoughtfulness and leadership they sustain on their foundation of habitual and skillful building.
I'll continue to hack out side projects, then, and be on the lookout for opportunities to leverage my skillset to be a part of bigger and better things. The scope of "building" is ripe for expansion, too: I love building physical things, too, and am planning on gaining more hardware engineering experience in one way or another in the coming months and years. I love writing too, and before that music, videography, and photography: other kinds of skillful creation.
There's always a tradeoff between exploration and exploitation, and I'm exploring a good amount at the moment, but I'm doing so with the planned eventuality of exploitation firmly in mind.
On the subject of exploration/exploitation, Ryan answered quickly when asked to give a piece of advice to the 18-22yos in the room: "take on more risk."
When you're young, failure conditions reputationally, financially, and in many other ways have far less of an impact than later on. Even if you lost all of your money and went hundreds of thousands of dollars into debt, or if everyone you knew right now hated you, you could still be completely fine in the longer term: you have years and years to make back money and build new networks.
If you have a family to support, on the other hand, or as your parents start to age and you take on other more meaningful long-term commitments, it becomes much harder to travel or take on ambitious and risky endeavors. "If you wanted to be in London tomorrow morning, there's nothing stopping you from doing so," Ryan said of us, while he had his family as a constant high opportunity cost.
If he were to make his life decisions over again, Ryan would potentially have started a company at a younger age, he said. The biggest risk he remembers taking when young is cold emailing and flying out to a startup incubator in Kenya: he regrets not taking on more risks.
This is the message that caught my attention the most. On a gap year with a trajectory available to comfortably stay out of school, I chose to de-risk my career immensely by going to a prestigious liberal arts school and embrace the comfort of advisors telling me to take it slow and not take on too heavy of a courseload until later years. On the note of traveling, my mom's criticism of me not following through with applying to Tsinghua comes to mind: I could be connecting with an entirely different country's culture and network through its most selective campus right now, and instead I'm staying comfortably at home with my intellectual boundaries expanding only at snail's pace.
This is not to say that there's not reason to make use of established career and learning paths; to shun them entirely would be foolish. Rather, the message is that there's much to be gained from pushing yourself off of these paths and seek real risk that you wouldn't otherwise take.
"I want to spend three months of the next year outside the country," I resolved to a friend in a car ride afterwards. I don't know where I'd go or what I'd gain, but this was something not in my plans to date, and something I would probably have to break some boundaries to follow through on, which would be valuable if for no reason other than training the muscle.
Much of the advice above reflects the push-yourself-to-your-limits, never-settle ethos that prevades and defines tech culture. (The alignment is even explicit in Ryan's worldview: "the meaning of life [and purpose of education, per another question] is to reach your potential," he told us early on.) Yet one thing that stood out throughout the Q&A was Ryan's warmly empathetic and people-centric attitude.
When telling us the value of dropping out of college, he contrasted himself to the "Naval Ravikant type" that advises you to drop out at whatever cost in optimization of what's best for you: consider your relationships and circumstances, Ryan says, and make a measured decision.
At Primer, Ryan allocates a budget equal to 10% of employee payroll to coaching for every employee, he said, which he also uses for him and his co-founder, prizing the mental health of his staff.
Reflecting on hard moments and regrets, he brings up a time when he didn't interject when an employee faced inappropriate comments from a superior -- it was a tough day for Ryan, and he didn't want to deal with it, walking by instead to a meeting he was already late for. The employee later told Ryan how alone and unsupported they felt in the moment. "That was something I regretted -- not letting someone feel that way just because I was stressed. That's something you can't take back or fix," Ryan told us.
A culture-breaking amount of social awareness was also woven throughout the conversation. Asked about books he's read (or something along those lines), Ryan told us about John Laurens, one of the only outspoken abolitionists in America's founding days, alongside Alexander Hamilton. Laurens died in a skirmish in 1782: "had he been alive, and been by Hamilton's side in debates, America might look very different today," he noted.
Asked about Primer taking on social responsibility when educating students, i.e. sharing certain kinds of content against parents' wishes, Ryan shared a thoughtful perspective on startups' decision-making. Companies can either choose to be an active part of the cultural narrative or not, he said, and neither are necessarily better; both are commitments that must be consistently followed through on, a frequently difficult task. Despite Ryan's sensitivity to social issues and obligations, Primer usually chooses to prize parental agency, a decision informed by Ryan's datapoints of homeschooled kids with limited perspectives growing up becoming well-rounded and open-minded adults later on.
The biggest display of Ryan's empathetic attitude is his love for his children. "Kids are so amazing," he said, reflecting that his children raise the opportunity cost for everything he does: "the alternative to staying late after a dinner party is reading books to my son, and that's like, the best thing in the world," he said. To have and raise kids is to trade fun for joy, he puts it: "a deep, deep joy."
Perhaps Ryan's relatively more well-rounded outlook is due to the fact that he's older, or has a family: against common advice, he married and had kids as early as possible, he said. He also attributes many personality changes, like not faking competence, to starting coaching a few years ago.
Either way, I'll remember Ryan for his warm demeanor and sharp advice. I'm not personally super passionate about edtech, but my friend -- a new grad looking for SWE jobs -- is. "I have a crush on Primer," he told me, and after talking to Ryan and his CTO, "I think they have a crush on me, too."
Mini-features on interesting people I encounter