If you went through Y Combinator any time in the past 7 years or so, you know: office hours with Michael Seibel just hit different.

And by saying this, I am in no way trying to downplay how fantastic the other YC partners are. There is obviously an incredibly high bar.

When you’re going through YC, or you have the opportunity to be advised by any YC partner, you can expect certain things:

First, if you’re prepared with questions, you’ll get a lot of questions back. You will be expected to have answers.

Then, you’ll get advice that may very well transform your company. The advice will, almost always, be direct and unambiguous – but sometimes the answer will be more like a heuristic.

It will feel like drinking from a fire hose, and by that I mean it will be fast-paced and you’ll cover a lot, quickly.

You’ll leave with a clear set of goals, a sense of urgency, and feeling of hopefulness and excitement.

But with Michael, it really is different. If you know, you definitely know – and if you don’t, I’ll do my best to convey what makes a conversation with Michael Seibel so inspiring and effective:

High intensity

In normal social situations, from what I’ve experienced, Michael is a very chill dude with a great laugh who makes others feel included and at ease.

But in the context of being advised by Michael: no. You’ll get the great laugh from time to time, but that’s about it.

We went through YC’s W20 batch (“the COVID batch”), the last in-person batch at the time of writing. I sometimes wonder whether remote founders in the more recent batches experience Michael’s intensity in the same way.

To say Michael “grills” you would be an understatement. The moment a question leaves Michael’s lips, the clock starts ticking. And less than two seconds later, you already can feel it and see it all over Michael’s face: “Does this idiot really not know how many unique visitors he’s had in the past two weeks?”

And, to add to the pressure (and this is where I wonder about the remote YC experience), Michael’s saccades – the movement of his eyes between fixation points – are on another level. You can actually feel the fixation on your eyes, the corners of your mouth, your shoulders, your forehead.

It’s one thing to be asked rapid-fire questions and be expected to have answers – that’s pretty standard. With Michael, it’s that, but on God mode. It’s that, but with a hypersensing supercomputer bearing down on you, wondering why you’re such a f***ing idiot.

I’m exaggerating a little bit, but that’s sort of what it feels like. And in case you’re interpreting this as a criticism, it’s not: this makes you a better founder. After a few conversations with Michael, you will hold yourself to a higher standard of knowing your shit.

Professional hater

If you follow Michael’s Twitch cofounder, Justin Kan, you might have heard Justin describe Michael as a “professional hater.” It’s kind of true. Michael is a straight savage.

Another YC partner might tell you that your landing page isn’t good and that you need to make some changes right away. Michael will tell you that your landing page is punching him in the face, and then he’ll ask you what the hell you were thinking.

This is another example of standard-raising, but it’s actually something more Socratic than that. “What the hell were you thinking?” is a really important question that sets the stage for a lesson you’ll never forget. With Michael, bad execution isn’t just fixed, it’s also scrutinized.

That anecdote about the landing page is a real one. We fixed the landing page – but we also had a productive conversation about what we were trying to accomplish in the first place. Later versions of our Art in Res landing page preserved the spirit of our original idea, but the execution was just way better.

When Michael goes into hater mode, the emotional stakes are high, but the commitment to understanding your decision-making process is high, too. The discrete ideas that went into your execution will be held up to the light and examined: “there’s something to this one,” maybe, but “this one is terrible.”

These conversations can be uncomfortable, especially to the uninitiated, but the lessons are both nuanced and enduring.

Chunking and pattern-matching

This one absolutely deserves mention, but feels more like a black box. I’m not a psychologist, but I promise there’s something to this.

You know how memory sport competitors (OK, maybe an obscure reference) use chunking to remember and retrieve huge amounts of information? Michael must be doing some version of that, because this man’s memory and pattern-matching abilities are absurd.

Pre-founder days, I worked in the investing world and I was a generalist. So I looked at all sorts of companies: healthcare, oil and gas, tech, telecom, insurance, whatever. Every industry and sub-industry was fair game, and every business model, too.

I’m definitely not a business analysis genius, but I’m good enough and experienced enough to know who’s good and who isn’t. All of the YC partners are excellent at this, but Michael is truly on another level.

The fluidity with which Michael can remember specific anecdotes and facts about companies he’s advised years ago, then transition from thinking about those companies as atomic units to groups of companies (with varying specificity across different dimensions), and do that with a sensitivity to time (the world changes quickly in Silicon Valley), while zooming in and out to varying levels of detail… it’s crazy to experience.

One time I remember this being on impressive display was early in our batch when we were thinking about pivoting our business. We got a call from Michael at about 8pm on a weekday. “What’s this I hear about you guys pivoting?”

The next 90 minutes were a tour de force. Michael analyzed at least 25 pivot ideas and problem spaces on the spot with zero preparation. Regardless of the topic, he could easily recall companies who succeeded, companies who failed, industry dynamics, strategies, regulations, products, pivots, growth channels, etc. But moreover, he would simultaneously theorize about possibilities: things that might work, things that probably wouldn’t, the direction of various industries, and the changing shape of the world.

There isn’t really a lesson here for founders, except that if you have Michael as a resource, you’re lucky. It’s evident that he puts in a ton of work and probably has some awesome genetic gifts, too.

Prescriptivist

This might be the one where Michael differs the most from the other YC partners.

I touched on this earlier, but YC office hours follow a general format. You come in with your questions, and you get asked questions back. You get great advice and the whole thing flies by. You leave and you usually feel pretty excited and good.

With Michael, though, there’s a decent chance that the meeting takes a turn. You come in with your questions, and you get asked questions back…

But then, something in the air changes, and you can feel it. Michael pieces something together. Your other questions are now irrelevant, at least for the time being. Michael is asking you more questions, and you’re at his mercy. The questions get increasingly psychological and emotional in nature.

And finally, the denouement. You get told exactly what you need to do. And you need to do it now, by the way. The floor is now open for questions, but except for a clarifying question here or there, you see how your other questions don’t really matter all that much. You’re inspired, you’re totally bought in, and you just want to get the hell out of there and back to work.

Everyone is fallible, and that includes Michael. In fact, Michael has said that about himself many times. Part of what makes startups so fun is the high degree of uncertainty and breadth of possibilities.

It seems perfectly reasonable for a smart advisor to remind themselves, “hey, I’m fallible, and this advice may be wrong.” The YC partners do this all the time, which is why it’s pretty common to get advice like “you should try X and Y” or “you should use heuristic Z to figure out the answer.”

Michael’s advice can often feel more like “And so it was told: Michael Seibel has spoken.” His ability to suppress his sense of fallibility and hit you with some blunt “do this”-type advice is sometimes exactly what you need.

Caring

I’m saving the most sentimental one for last, and I think PG’s essay about Ron Conway was sort of the inspiration for this essay. I wonder why it’s not more common to write essays about people who made your life better, or people you admire.

I’ve covered a bunch of ground. Michael will psychoanalyze you, obliterate you, teach you, and tell you what to do. But despite the high emotional stakes and uncomfortably blunt advice (that may or may not involve you feeling like an incompetent moron), I never for one second thought “Michael doesn’t care about us.”

In fact, quite the opposite – it’s pretty evident from all of our interactions with Michael that he cares a lot.

It would be totally fair for Michael – or any YC partner or investor, for that matter – to just care about their portfolio founders in the context of being an effective operator. But I truly feel like Michael cares about his YC founders in the way a teacher cares about their students.

He wants us to win, and he wants us to succeed, and it would be amazing if that meant winning and succeeding together. But if winning meant shutting down our company, or succeeding meant quitting and doing something else, that would be OK, too.

Michael’s brand of caring is tough, charismatic, and wise. And it’s unmistakable – he takes a ton of time and makes real sacrifices in the service of caring for his students.

I hope this was a fun read for other YC alumni, and hopefully brought back some good memories. It definitely did for me – my cofounder and I had a lot of fun reminiscing. If you’re considering applying to YC, do it – it will be a great experience and it will make you a better founder.

✌️

posted 23 oct 2021