Asking the uncomfortable questions, w/ Michael Seibel, Y Combinator

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Shogun is so interesting because There are all these situations that confront the two main characters. Where They're given two bad options. It's like here are your two options.

There are two items on the menu. And they both kind of round to death. That's Michael Sybel. Managing Director of Y Combinator. You know.

The storage startup accelerator that counts Airbnb, Dropbox, Reddit, and Stripe among its many successful alumni companies. He's talking about one of his and my favorite novels. The classic Samurai Adventure. Shogun And the smarter of the two characters tournaga

He always finds a way to introduce The third option. Which is like let's wait. Let's wait. How about we wait a day?

Even in the most pressing of circumstances, Toronaga takes the time to ask himself this question. There was some order given for Turnaga to show up and see the Emperor and then he's gonna be killed. And His brother is dispatched, I believe, to deliver this order, which I love.

That's kind of a shitty thing. But they're on this road to see the Emperor. It's gonna take like fifty days to get there. So the brother presents him with this order, which in Japan, theoretically This is as good as a death sentence. The brother's like, why do we have to do this long trip?

I'll just kill you right now. And That's how we should go. But Toronaga. has a different suggestion.

Oh let's take the trip. Fifty days that's a long time. Maybe things will change. En so

That's helped me so much along the way when you feel like you're boxed in, and then you just ask yourself, well, do I have to make this decision today? So often You really don't. So did asking an unexpected question work out for Toronaga? You'll have to read Shogun or watch the T V series to find out.

But what about you as a founder? How often do you stop and say How about we wait? especially in a rapidly scaling startup. Where speed is of the essence.

In fact. Even asking this question seems contrary. to the classic startup wisdom of moving swiftly and burning your boats. It's just one. Of the many contrarian questions, Michael urges why commoner or why C

Founders to ask themselves. Um Okay. Founders always try to reduce multivariable problems. And the single variables.

And a lot of problems are multiverb. Some decisions where you actually do have to decide right now. They're the decisions that are absolutely you don't And I find The most common question I ask is a

Why are we talking about this? Why is this essential? Right now at all. As opposed to what's the right decision to make.

Michael urges founders to ask the uncomfortable, self-searching questions that may feel contrary to the norms of startup life. Why is this essential right now? is only one of the many important questions. Because whether you're a seventeenth century Samurai Or

A twenty first century entrepreneur. Knowing what questions to ask. And when is essential. That's why I believe you need to learn to ask the right questions of the right people and then act upon the answer.

Even if it seems irrational. You gotta have incredible talent at every position. Huge push. There are fires burning when you're going out. Can you believe that? Such an idiot. And then you go back to this is totally gonna be amazing. There are so many easy ways. I have no idea what to do. Sorry, we made a mistake. But you have to time it right. But well that's just how you do it. We haven't made just how you do it. This

is masters of scale. I'm Reed Hoffman. Co-founder of LinkedIn, partner Greylock. And your host. And I believe you need to learn to ask the right questions of the right people and then act upon the answer.

Even If it seems irrational. The third planet. From Altair. Who killed?

Harlow Thrombe. The Mona Lisa is missing. Warm with a mutant spider ants. If

Like me, you spent part of your childhood enthralled by the book series. Choose your own adventure. And some of those titles. may be familiar to you.

Every few pages, each of the books invariably written in the second person. Would challenge you to make a choice. and then turn to a specific page number to discover the outcome of your decision. Some of these choices were pedestrian. Do you turn left?

Alright. at the fork in the road. Some had higher stakes. You open the box, Art.

Danger. Mutant spider ants. Or do you douse it in gasoline and set fire to it? Even the most unassuming of these questions could have the most astounding consequences for your character. Quite often.

An untimely and gruesome demise. But in all of these books, there's a way to guarantee success. Just click ahead until you find an ending that appeals to you. Unfortunately. There's no such shortcut when it comes to entrepreneurship.

You can't dodge answering questions, and you can't know in advance how the consequences of your decisions will play out. What you can do is make sure you ask the right questions of the right people. at the right times. That's why I wanted to speak with Michael Seibel. He co-founded the pioneering live video streaming platform Justin Taught TV.

Whatever twitch. And also the video sharing app. Social Cam. In two thousand thirteen He became a partner at Y Combinator, having worked with Accelerator since his Justin TV days.

Famously, it was Michael who introduced Brian Chesky and his then struggling startup. Airbnb. to Y combinator. At key junctures in his life and career, Michael's decisions have often hinged on asking himself questions that got to the heart of the motivations and assumptions of himself and others. This ability to ask the right

Counterintuitive questions at the right times of the right people is an essential skill for entrepreneurs and one that Michael Puts at the center of his work. with young founders at YC. Michael first realized the power of asking difficult questions in his high school constitutional law class. You'd actually you know read about the constitution or read about

A lot of US government stuff, and then you would debate resolutions as if you were in Congress. To put it frankly, it was the first time I could measure myself against the smartest kids in my school. And so realizing that I could be as good as them in this debate class, I started asking myself, Well, why am I not in all the other classes that they're in? During these debates, anyone No matter where they sat in the high school pecking order. Could ask questions of anyone else.

And this spirited inquiry led Michael to ask himself a rational question that uncovered the irrational truth at the heart of the school system. It made him doubt the value of the whole high school. tracking system that group kids into classes based upon their perceived ability. And up to that point in school, I was in the honors track. that track had just started getting separated into honors and AP. So there it just became three tracks and I was in the middle track.

But this class had all three. And tracking is so weird because on one hand it works great. It puts you in this great environment. On the other hand If you're mistracked, uh doesn't work so well. Spurred on by this realization, Michael doubled down on his studies and won a place at Yale, majoring in political science. In his senior year at Yale, he found himself in a class with a student named Justin Conn.

And the entire time Justin and I were in school together, I thought he was annoying and didn't want to be friends with him, but we we just became friends and Hilariously along the side. Justin and his friend Amet applied to the first batch of Y C. This was the summer of two thousand and five, and that first batch of Y C founders included the Reddit co founders and the future Y Commander president and former Masters of Scale guest, Sam Altman. The startup that Justin Conn and Emmett Shear brought to YC was a calendar appeared.

Name Kiko. It was a time when asking yourself What should I do with my life? And answering entrepreneurship was a rarity among recent graduates. In fact

Doing so was seen as irrational by most people. And Justin went down this path of starting a startup, which at the time I don't think I can communicate to everyone listening how uncool that was. It was so uncool, it was dismissed. It wasn't like even insulted because that would be giving it too much attention. It was just irrelevant. Everyone wanted to be a banker and consultant. Sometimes I wish we were still in those days now, but um

Times change. I don't. I actually think and you're your whole work. I mean Y C and all the rest. It's actually better to be builders. Fair point, yes. Probably not better for the world, but sometimes I experience the pain of the uh Of the scensters, let's call them. Yes. Well, the people going into entrepreneurship because it's status versus building. Exactly. Yes. Michael moved to Baltimore to work on the Senate campaign of Quasi M Fume.

Meanwhile. Kiko was crushed by Go Calendar. Which launched in two thousand and six. Justin's next pitch was very different. Justin.

told me they were doing this over dinner with his dad in DC, and we both told him it was the dumbest idea we've ever heard in our lives. Which I still believe to this day. That idea was just in TV. The plan to live stream Justin's day to day life. Twenty four seven.

With a webcam attached to Justin's head. Today this seems quaint, but in two thousand six this was brand new. I think that in hindsight We always tell founders to start companies to solve personal problems. And back then he wanted to be an influencer and there were no influencer platforms.

Twin ex Like all the things that an influencer would just reach for. He didn't have and so Almost incredibly he invented a platform that allowed himself to become an influencer. Note that Y C edict. That Michael mentioned.

Wise always tells founders to start companies to solve personal problems. It's invaluable advice. By asking yourself. Which problem is most personal to me, you're far more likely to hone in on a mission that you will have limitless drive to follow. And that's why even if that mission seems irrational compared to others you could be following.

It really is the one that you should be following. Justin and Emmett pitched their idea to Paul Graham. Serial investor, entrepreneur, and co-founder of Y Combinator. Paul and Y C put in fifty thousand dollars. In the meantime.

Quasi and Fume. had lost his bid for the Senate. We found ourselves at this interesting moment where I was looking for a vacation. And Justin and Emmet were taking a road trip across the country.

To start a new company. And I invited myself on this road trip. Michael had begun to ask difficult questions of himself. About his direction and his purpose. I was just going on vacation.

And I felt bad because we were in the Bay Area and they were starting to work. And I'm just kind of the friend who's sitting there watching their two friends. try to the impossible and so I helped them start a bank account to deposit the investment they had. And I helped them find an apartment. That's a thank you.

And when I was headed back, Justin gave me a ride um to the airport and he asked me to join the company. And I said no. And then he was like Yeah, I'll just think about it. If Justin's question to Michael sounds familiar,

Cast your mind back. To the start of this episode when we took a trip to Samurai era, Japan. Tornaga. He always finds a way to introduce The third option, which is like let's wait.

It prompted Michael to ask himself another question. Well taking this path. Stop me from achieving my goals. The thing that kept on sticking in my mind was all of my other options. would be available in the future.

Every other thing I was considering doing would be available, and this is the one thing that felt like it would never happen again. How being my friend start a company. And something just told me Do the thing you can never do again when you're twenty three and have nothing going on in your life. Seems like a good play. And it was. And so I called them and I said, Uh yeah, uh I'm in.

Michael became Justin TV's CEO, with Justin as president. Thanks to his naive but effective fundraising. We've figured out how to raise two million dollars series A, and a company that I thought was a bad idea. That was not part of my life plan at all. I'm now the CEO of at twenty three.

And we got two million dollars in the bank. Yeah, all right. I guess I'm an entrepreneur now. Like I don't know. Yes, exactly. After eight months of streaming Justin's life, the team opened the platform up to let anyone live stream. The company started making a profit. Things were looking good.

Until investor Gideon Yu told them his opinion. And he didn't hold back. He was hanging out with us. It was unclear why he was never gonna invest. They came by the office.

And he was like, Oh, you guys look really proud of yourselves. That's what I tell you, you know, your product as it exists today. The sh And you And your company are gonna die in the next three years.

Almost no matter what you do, if you keep down this path. And no one will ever remember all the hard work you gave. And he kinda said it just like that. Just kinda like this is what's gonna happen. It was a brutal assessment, but it got Michael and his co-founders asking themselves the question that they had been avoiding until now. They had been asking, is this working now?

To which they could answer Yes. What they should have been asking was Will this continue to work and scale down the road? And it was funny because we knew that. But while the specter of death

was over us because we were on this V C fundraising kind of train. We never really acknowledge it, but the second we were profitable. And we got that message, it was like oh yeah. He's exactly right. He's exactly right.

Let's fix it. And in some ways I think Gideon U has been my mental model for how to advise startups. Overlooking the most important questions when you're stuck in the thick of starting a company is a very common mistake. Especially when those questions are long term strategy and you're caught up with short term survival. And finding the right people to ask for help when answering those questions will be hard if you haven't built a strong network.

My producers asked me about this. While reflecting on my conversation with Michael. It's very easy to overlook. Maybe not. All of the most important question.

But uh Most important question. Usually you're cognizant of at least some of the really important questions. Even when you're in the thick of getting things running. But that's part of building the right networks around your company because part of

The function. of these investors. advisors, board members is to go, Well wait. Do you see this risk? Or wait.

Do you see this opportunity? In this case. Gideon was asking the hard question that Michael and his team hadn't considered. You put in all this hard work. You've secured all this funding.

But the product As it exists. Today. isn't gonna get you there. So

What are you gonna do? Here's how Michael and his team answered. We decided on two ideas. Instagram for video and justin TV for gaming. Then we do a classic error, which we talked to a bunch of investors and said, Which of these ideas will work? Which I always love'cause like

Probably should talk to users. Exactly. You might think this classic era stems from not asking yourself. What does my investor know that my customers don't? This question is important. But not as important as the follow up.

Does it matter? Because what your investor thinks may have no bearing on what your customers want. You can think of investors and customers as two different Usually unrelated species. You need both.

For your company's ecosystem to thrive. Both operate. In very different habitats. Investors have resources that very few consumers have. They are also

Idiosyncratic in their outlooks. Consumers tend to be excited about the product or service. Whereas investors will typically be more interested in the business model. Some of your investors will feel they are experts in co-shaping your product. And that's fine if they're right about it.

If they aren't. then you're gonna have serious problems. Kide and Yu wasn't an investor in Justin TV. But his advice prompted Michael and his team to take another look at what their users were energized by. So in 2011, the Justin TV team decided to split their focus on two new products.

The first was Twitch. A spin off to capitalize on one cohort of Justin TV users that had grown rapidly and unexpectedly. Gamers. They enjoyed live streaming themselves as they played, and many, many other gamers enjoyed watching. A whole sub community.

had grown around video game streaming on Justin TV. The second was Social Cam, headed up by Michael. SocialCam was a video sharing platform aimed at mobile users. Phones had reached the point where mobile video sharing was poised to take off. But for some reason it was stalling.

Michael and his team saw an opportunity. We had A good understanding of the problem, which was basically that people felt comfortable taking photos but not taking video. And The proliferation of smartphones meant that for the first time everyone had a video camera in their pocket.

I think that the logical leap we never made. Was that The way you get people to be more comfortable taking video. Was not to make it easier to create nice videos. It was to make it very easy to take sh videos.

And The company that nailed that was Snapchat. play that hand a hundred times, I don't know that we make that leap. And I think one of the reasons why was we weren't the user. Other things happened, but that was the game and and and we didn't win it.

And what is the game is obviously related to the earlier thing of ask the right question. Part of the reason I missed Twitter as an investment is I went, ah, 140 characters. What's that? And it was a very similar thing, which is actually, well, no one can look that smart in a hundred and forty characters, so no one looks dumb either. Right.

So part of how it opens up blogging is actually writing something where you look like a good essayist, that's hard. Takes a lot of work. Writing something that's like San Diego's high school football rules right. That you can write all day long. And read, we have many peers who prove that point every day on Twitter. Yes, exactly. Exactly. This is why asking the right question is an art. You need to be able to see from multiple viewpoints, understand a range of motivations.

Dig beneath the surface how's it? To the deeper wise. Ask these questions early and often, and then act upon the answers. And if those answ irrational. Well,

That means your competitors are more likely to overlook them. In two thousand twelve, Autodesk made an offer to buy SocialCam. Michael had to ask himself if they could win the game of changing video creation. Or if it was time to sell. So we knew it wasn't working.

Meaning we knew we weren't changing video creation. And we knew that was the game. I was like, you know, we're being given a pretty good offer here. I know we don't have it. We might get it, and we have a lot of investment offers. We could have raised a lot of money and given ourselves a lot of time. But you know, maybe we should get off the train.

The question seems like a simple one. Should I sell or stay in the game? But there was a deeper question that Michael needed to answer first. And this great conversation with Bing Gordon. Bingordon

Former chief creative officer at Electronic Arts and VC at Kleiner Perkins. He very calmly asked, Michael, are you a video guy? And I was like, What does that mean? He's like If we talk ten years from now, are you gonna be working on video? I literally laughed when he said that. I was like, absolutely not. Video's been the bane of my existence.

Video is so expensive, like video has gotten me sued. All the bad stuff in my life has come from video. Like absolutely not. Mm. And then it became obvious. So social cam sold to Autodesk for sixty million dollars. Just eighteen months after launching.

Getting that deal done was a little tricky. It almost didn't happen, but it did. And We are grateful. It was the best outcome we would have hoped for for not having the right answer. SocialCam didn't find the right answer in terms of what their product needed to look like.

But Bing Gordon had asked Michael the right question about Michael's own mission. And it set Michael on course for the next phase of his career. Helping founders ask themselves similarly searching questions. When you've built substantial wealth through your business, it's often tied up in a single equity position. The upside is real, but so is the risk, and knowing when to act isn't always obvious.

Creative planning works with business owners to build a strategy around concentrated equity. When to diversify, how to manage tax risk, and how to protect what you've spent years. Building. Creative planning where wealth works together. Learn more at creative plating dot com slash masters of scale.

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Find pioneers of AI wherever you tune in. We're back. In two thousand fourteen Michael joined Y Combinator as a full time partner. I had been a part time partner before and helped out and I'd been around Y C my basically my entire entrepreneurial career, so I knew everyone. And then

For the first year or so I really just enjoyed not having A startup that was gonna die every second, right? Did a little traveling I got engaged, I got married. But then one of the things you learn about effective people is they like getting punched in the face. They like work.

And so I started Doing more and more stuff. at Y C and then In twenty sixteen I started running the accelerator, which was just kind of a I wouldn't have picked that out.

But it's been going a while. A huge part of how Michael works with founders is getting them To ask the right question at the right times. So my wife just describes it as therapy. And that's probably accurate.

Nothing that I tell a f nothing. Ninety seven percent of what I tell a founder they can find online and read it. I try to be honest. There's a lot of lies and half truths about how this game really works. Like therapy.

The point of the questions isn't so much about the answers. It's about prompting a change in your thinking. I wanted to dig deeper into just how we go about forming the questions we ask ourselves. Brian Christian is the author of a number of books that explore the broader human implications of computer science. One of my favorite quotes about computers comes from Pablo Picasso. Who said

Computers are useless. They can only give you answers. And I think part of what he is gesturing towards there is something that's very recognizable to people who work in machine learning today. Which is If you can frame something you're interested in.

in explicitly numerical or computational terms you can crunch the numbers and get some kind of answer. But It's much harder to determine what it is that you should be paying attention to in the first place.

Our attitudes have come a long way from the nineteen sixties heyday of techno optimism. Where computer scientists dreamt of feeding punch cards into a mainframe the size of a hot dog stand. Compute every variable in a person's life and output. The tidy answers. To being happier and more productive.

There are certain things that we care about that are not easily encapsulated. In some operational numerical definition. And it's important to remember that those things are just as real as the things that can be measured.

Right. That's the famous quote by Einstein, if I'm not mistaken. Not everything that Counts can be counted and not everything that can be counted counts. Asking and answering questions doesn't just help get us to where we want to be. It actually helps define Who we are.

Philosophers like Ruth Chang at Oxford says It is the nature of being human. to have to make Hard choices based on competing values. that if you have to decide between a career that's

more lucrative, a career that's more Prestigious and a career that's more fun. No one can do the math. for you and tell you which of those values wins. You have to choose.

And She argues, moreover, that you know, it's not like you merely discover within yourself that you are the kind of person who cares more about one of those than the other. But that you become that person by making the choice. And so from that perspective, you know.

to struggle with these Existential questions of what to do with your life is an intrinsic part of what it means to be human and in some ways a gift to be in that position. At Y Combinator, Michael spends a lot of his time helping entrepreneurs struggling with their own existential crises. I try to get them to focus on the right stuff versus the wrong stuff. And a lot of what Y C is about is like

Here are common patterns of failure. That are so well Travelled. that we can describe them to you in detail. We have this line we say, where like if you're gonna fail, can you just fail in a unique and interesting way that we can learn from

What do you think are the most kind of classic Lies and the half truths. Number one is that money will solve your problems. Number two is that employees will solve your problems. And number three is that smart investors will solve your problems.

Those three things. Kill Y C companies left, right, and center. Because it gets people to stop worrying about product market fit and start worrying about company building. And the number one killer of startups is company building. It's the number one killer of startups. And People are

Ten X more afraid of scaling too late than scaling too early. Which always blows my mind. Yeah. Scaling too late. Isn't fatal. It could be bad, but it's not fatal. Scaling too early is almost always fatal. You won't have all the answers, of course.

But you do have the questions. Once you figure out what questions are most important to you, you can ask them over and over in each new situation. The pandemic forced YC to ask difficult questions about its own operation and if change was needed. So I think that the pandemic helped YC a lot.

I think that there were so many sacred cows about how YC should run. That we just took for granted because it had been around for over a decade. That had to be killed because We couldn't meet in person.

And it allowed us to innovate. And it's been great. It's been absolutely great. Those changes. Many of which Michael has spearheaded, included focusing more on virtual engagement,

Pushing for more diversity and spreading YC's international reach. I spend more time With the founders going through my group and Y C Then I did.

when Y C was in person and my group is two times bigger. Uh and that is not intuitive. We've been able to really push forward the kind of secret superpower of Y C, which is F the advice, f the fundraising. We hope you get customers. And make revenue.'Cause at some point I think and I don't know, I'm not a

Business school guy, but like I think you have to make money, right? Unexpected new circumstances will force you to face questions you've been avoiding. Coming up with rapid answers to them and then implementing these new, possibly uncomfortable ideas can help catapult your project ahead. But there is one ultimate question that every founder faces. Particularly.

When they first start out. But it can rear its head at any time. Especially during the darkest moments. And it's an existentially uncomfortable question. Should I be?

A founder. Who should and who shouldn't be. Found. For folks who are out there. To kinda say, Ooh, I should really consider this and think about this, and other folks going, Ooh, I should stay away from this.

This is a question I really thought about a lot. I think you need to have some type of a rational motivation. And I think the thing that I've learned is that there are different sources of a rational motivation. So One can be the irrational motivation of working with a friend.

Right. I really like working with this person. I love working with my best friend. And so I will do the dumbest thing with them because it's more fun than anything else. Sometimes rational motivation about a problem that you have. or your friend or your community has. And solving it. Sometimes it's an irrational motivation.

Where you're running away from something. I can't function inside of Google, let's say. Sometimes it's this thing broken in your head. You know, the way I describe it is that like I can only produce my best work when there's a gun to my head. And I wanna produce good work.

And so I think that I always search for what is the irrational tie because every founder lies to themselves and tells themselves their business is gonna work and can present the logical argument, right? And we help them write that, and we know that it's a lie, right? And so I wanna know when that logic argument starts getting Beaten by reality. There's something underlying that's gonna keep you motivated and I think that people don't think about this enough, which is

What is gonna be your Not never ending, but deep source of personal motivation that will stand. Bad times. I guess, you know, I give somewhat similar advice, which is Being a founder means that you're going to make a number of sacrifices in pursuit of this mission.

You should not presume that you have the classic eighty percent of Americans or eighty five percent of Americans think they're above average, that you have an eighty five percent success rate. You should presume I usually tell people it's like look, you are thinking that you have an over fifty percent success rate. You should presume a substantially under fifty percent. Stance of success rate. And part of that then is to say, look

In your path and approach of so doing this. That you're comfortable. Like that this was a good use of time if it doesn't succeed. Because as you're pointing out, it's like you have some attachment to this. And then even with the right motives, even with the right intention, even with the grit or the masochism

Even with a commitment. You also need to try to get А з гуд за реалістик шасо. on this and part of that is go around to the smartest people you know and ask them what's wrong with it. Because

You know, unless you have uh something that's timely Serendipitous. Competitive edge, etc. These are so much work. Right. Startups always leave lots of blood, sweat, and tears on the floor.

These are so much work. To make sure. that this is one of the shots that you want to take. It doesn't have to be the one that's they're not guaranteed. But you want to take this shot. Be irrational and be smart about it, okay?

Yes. Exactly. Yes, irrationally good decisions. The way to keep making those irrationally good decisions? Keep asking questions.

Not in the spirit of self doubt. But in the spirit. of self examination and in a way that feeds your motivation. And expand your ambition. I'm Reed Hoffman.

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