Fireside Chat at OSU's Intro to Software Startups
OSU launched a brand-new course for future technical founders, and I got to be one of the first guests. We covered career risk, YC, and how engineering changes when you go from building at startups like Twitch and Teespring to scaled organizations like Meta or Block.
In February 2025, I did a fireside chat for Intro to Software Startups (CSE 5889), a brand-new course at Ohio State University run by Dr. Arnab Nandi.
The class is exactly what it sounds like — a CS course built for students who want to found or work at a startup. It covers the full arc: problem identification, founding teams, cap tables, go-to-market, fundraising, and the actual technical side of building fast. The target persona, as Arnab put it, is "the future technical founder." The ~50 students were CS undergrads and grad students who opted in — so the energy in the room was high.
One amusing scheduling detail: Block's quarterly earnings call was exactly one hour before the fireside chat. I flagged this to the team in advance — I'd be happy to answer anything, but I might have to dance around anything that had just been discussed publicly 60 minutes earlier.
Format: Fireside, Not a Lecture
The format was a fireside chat rather than a structured talk, which I much prefer. It's harder to hide behind slides. Arnab had framed out some topic areas in advance — career trajectory, YC, engineering at different stages, risk assessment — but the conversation followed the students' curiosity more than any script.
The unstructured 30 minutes after the formal session was actually the most valuable part. Students came up individually with pitches, career questions, questions about specific companies. The ones who were already building something, looking for a gut-check on their direction, were the ones I remembered most.
What We Talked About
The career trajectory. I started as a content creator before working at Twitch, Teespring, Meta, and now Block. Each move looked different from the outside. From the inside, there's a single thread: creator commerce and economic empowerment. How do you give creators the tools to build real businesses around their audiences? That question has followed me across every role, and honestly it's the closest thing I have to a life mission.
Each individual move was still its own risk assessment — is this a two-way door or a one-way door?
Leaving school to join a startup early felt irreversible — an unknown company, not obviously a good idea at the time. But it was a two-way door. If it didn't work out, I could go back to school or find another job. The cost of being wrong was bounded. I've used that framing ever since when evaluating decisions that feel big.
YC. Both Twitch and Teespring went through the program — and I've also seen applications on the other side. The thing that stands out isn't uniqueness of the idea. It's clarity of thinking and evidence that the founders have actually talked to users. The weakest proposals are usually polished pitches with no evidence that anyone outside the founding team wants the thing.
Big company vs. early stage engineering. At smaller startups, engineering was survival mode — you shipped fast, you cut corners you knew you'd regret, you bet on what you thought would matter. At larger companies, engineering is about operating with much higher stakes at much higher scale. The discipline is different. At a startup, the biggest risk is building the wrong thing with limited runway. At a big company, the biggest risk is moving so carefully that you stop building anything.
The through-line is: context changes what "good engineering" means. A practice that's smart at one scale can be the wrong call at another. The best engineers I've worked with have internalized this — they're not religious about any particular approach, they're good at reading the situation.
Innovation at scale. One of the questions was about how big tech companies keep an innovative culture — or fail to. There's no clean answer, but the pattern I've seen in the places that pull it off is that they give people genuine ownership, not the appearance of ownership. Autonomy with accountability, not autonomy as a euphemism for being left alone with a bad roadmap.
What I Took Away
I came in expecting to answer questions. I left feeling like I'd gotten as much as I gave.
The students were genuinely engaged in ways I don't always experience in professional settings. They hadn't yet built up the habit of asking safe questions. A few of them pushed back on things I said, which I appreciated.
If you're an OSU student and found your way here — I meant it when I said I'm happy to hear from you. Reach out anytime.