My Experience Interviewing With Michael Seibel of Y Combinator

This is is part of my live-learning series! I will be updating this post as I continue through my journey. I apologize for any grammatical errors or incoherent thoughts. This is a practice to help me share things that are valuable without falling apart from the pressure of perfection. 

Episode Summary

– Who is Michael Seibel?
– What is Y Combinator?
– How we prepared for the interview versus how it went
– Personal experience preparing for an interviewing with Michael
– Wanted a very specific example of our application and one that we can monetize
– Had pretty solid responses to his questions
– Had quick responses to his answers with the goal to let him ask as many questions as possible
– Only had 358 users on the platform at the time
– Really wanted to know who are customers are
– Wanted to know how much of Speak Ai is a transcription product versus an analysis
– Wanted to know if we have a goal to get cheaper transcription
– About halfway in I deviated and talked about why I built this and the personal journey I had been on
– He challenged us that we were pitching something different than what was in the application
– There was frustration about ¾ the way through the interview
– Did not like our answer about bootstrapping and why we were prioritizing some customers over others
– Michael shared that there are a lot of people tackling the same problem we are with research and the more personal analytics application was unique and worthwhile
– We struggled with this recommendation because those users hadn’t paid us any money whereas the others had
– This is where I see foreshadowing to the environment we are in now because he recommended us to go that route
– Coming from an agency background and not living in Silicon Valley I struggled with that a lot because if we couldn’t get the revenue we couldn’t keep funding the business
– I had already taken out personally liable loans for the business because I didn’t have access to investors and would have been in a horrible place if we hadn’t been generating revenue
– From his perspective (and I can partly agree), our articulation of the product was not clear and he was not sure how to use our product
– Definitely was some tension towards the end of the call as we hit a point where he asked us to explain what we are doing to him as if I was speaking to his mom
– We moved from the corporate side to the personal analytics side and that is where the failure ended up
– Tried to tie it all back together in the end but it wasn’t succinct enough
– The 10 minutes went by extremely quickly and it felt like a microcosm of everything we had worked up to until then
– We reflected on the conversation after and recorded a conversation between Vatsal and I
– Michael had shaken his head in frustration multiple times and we stopped to address his concerns
– Overall I would say it almost felt like a traumatic experience but still a good one
– We felt optimistic overall that we would have a second interview for them to learn more
– Felt like we were describing our company one way and building it another
– We did not expect to be interviewing with Michael Seibel that was a surprise to us for some reason
– Split between Vatsal and me talking
– Did not care about the technology as much as the problem and the way the customer uses it


Y Combinator
Michael Seibel – Wikipedia
(5) Michael Seibel | LinkedIn
Y Combinator (@ycombinator) / Twitter
YC’s Michael Seibel clarifies some misconceptions about the accelerator | TechCrunch
Y Combinator is still paranoid | TechCrunch
tyler bryden y combinator – YouTube
Y Combinator Winter 2023 Application – YouTube
Y Combinator Reduces Cohort Size By 40% Due To Economic Downturn – YouTube
Y Combinator’s Warning Letter To Founders, Their Role In Startup Correction & Advice For Startups – YouTube
Tyler Bryden – YouTube
Michael Seibel (@mwseibel) / Twitter


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YouTube Video


Automated Transcription

Hello, hello, Tyler Bryden here. I hope everything’s going well today. Talking about something interesting, this is actually from a few years back, but I think is a timely considering that why combinators deadline for their applications just closed. There’s thousands of companies who have applied for why Combinator, and now a select few of those are being selected to then interview with the Y Combinator team. And so in this video I want to talk about our experience. Speak I think September 2020, having. An interview with why Commander and Michael Seibel of of YC and.

This was, you know, super, you know, super scary, challenging, nervous experience, I would say almost borderline traumatic, but in a positive way that just expedites and accelerates self growth. And also that, you know, a couple, I think disclaimers off this is we did this interview and I’ll talk about the actual interview itself. We did not get into YC. We got a nice e-mail from Michael after and I’ll share a little bit more about that also that this is sort of my perspective. Of this experience of this interview, there were other people there besides Michael. One including my CTO. And then if I hadn’t blacked out in the moment, some amazing people who are obviously part of the YC team and helping select the companies that do get accepted. So I have, if you don’t know what YC is, I’ve shared several videos on them in the past. I’ll just pop this up so you can see and you can get the classic inception of tool. So recently I did that. Why? Combinator?

Enter 2023 application, which I was glad to see that some good feedback and you know, inspired some people to apply. And then a couple other pieces here including a warning letter to founders about, you know, the market conditions that have changed. And in part of this I actually talk about their role in you know, the the market environment that has happened in sort of venture capital. And I want to talk a little bit about that in the video because it’s sort of been apparent in my mind recently as. I’ve thought a little bit more about some of the things happening right now and I’ve got, you know, as as all always a couple of links and resources. So you can see like, you know, they’ve almost done 4000 Startups, 9000 Founders, 1 trillion in market value and some huge amazing successful companies that have come out of YC and you know for, for myself, for vassal, for many people who are building tech companies and young and early in their career. And I say that now as I’m turning 30 and not necessarily that early in my career anymore that Y.

He is sort of like the gold standard and something that we all aspire to. And so, you know, it was a huge moment to successfully apply to get at least the interview with Michael. And I’m, you know, a huge, you know, I’m very grateful for that opportunity, the connection, the questions that he gave us in those 10 minutes and then the e-mail response said he he gave after about, you know, why they hadn’t chose to proceed with us. And overall, you know, I’ve learned so, so much from him. I have a lot of admiration.

And, you know, he’s had a ton of success through his career, a lot of it directly connected to Twitch, which then sold to Amazon. And you can find videos on hamelink a couple, in case you’re wanting to check those out. I’ve also got his LinkedIn, I’ve got the YC Twitter, and I’ll actually drop Michael Twitter in here as well too. But I did want to sort of talk about I I’m not able to show the actual specific application itself, and maybe one time I’ll pull it up and do it. I just want to talk about the actual interview and I’ll say.

For anyone, again, hopefully what I’m sharing from my experience helps you prepare for yours and maybe gives you a higher chance of success than you would have if you hadn’t heard this video or watch this video and, you know, maybe some insights that I didn’t know as I went into the conversation. And first of all, I guess the first one was like, we didn’t actually know we were interviewing with Michael. We had no idea who we were going to be interviewing with for this YC app, you know, for this interview. And it was just like a little bit of a shock right away. I think both. That’s when I felt that immediately is like, even though.

Makes sense now in retrospect. We had, when we have done a lot of preparation, talking with people who had gone through YC, we did mock interviews, ones that went poorly and then had moved towards actually being pretty good, and we had gotten good feedback on it, just hadn’t really fully crossed our mind explicitly that it was going to be Michael. And so there was a moment of sort of shock that came when we realized we were talking directly to him and that this was going to have a huge impact on the success of our application and then generally our life, I think if we had gone into NYC. Especially at 2020 in the sort of peak of this frothy market, we would have accelerated PKI in a huge way and I think our lives would be very different right now. So that’s interesting. It’s own that there’s like a 10 minute microcosm that can actually have a substantial impact on your life. And in my way in in in some cases I feel that, you know, I actually failed in this moment. This was a moment of failure for me personally where I was not convincing enough.

To believe in myself and then also obviously the vision that we had in the company. And I do recommend if you can, if you are being asked to interview, reach out to as many YC founders as you can and do mock interviews with them. 10 minutes run through, they’re gonna drill you with hard questions, and that’s a huge preparation for the actual final interview. Also say that you cannot prepare necessarily for the interview to go the way that you want, and at the time we only had like almost 400 users who had ever signed up for the system. Now we’re almost towards like 7000, but.

Our tech was actually relatively strong early in and so we thought that that was our huge sort of differentiator and a key part of what we wanted the pitch to be. And so we did these nice little introductions, we punch, punch, punch and then we said, hey, we’d love to show you a demo of the platform and immediately he was like, OK, well, let’s talk about this first. And so right away we had this plan that sort of fell apart immediately and all of our sort of, you know, we really thought that once we sort of walked through the product that that would be. You know, a huge part of what we quickly realize and I think this is a lesson for you know anyone in sort of startups or building businesses or whatever it is, is that you should be focusing on the customers and the problem that they have and not necessarily the solution. And that’s I think a constant thing that we’ve dealt with here at PKI. And I think just a lot of people who love technology deal with and in general as we love the technology, we don’t necessarily think about the, you know the problem and the solution which or sorry, the problem and and the customer and their you know how they interact with it and what’s their workflow and what’s breaking for them and what makes them.

Do not fall asleep at night and the pain that they face, like those are things that we sometimes forget as we fall in love with the technology and especially in the market where it was where it was like if you had this idea for tech and you knew enough people you could like throw this around, throw around some buzzwords AI and then it became NFT blah blah blah, and you could get funded and then grow the business like those. Those were all sort of readily apparent and and left us, you know, not not as focused as we should have been. He, you know, really drilled on us is that. You know, first of all, he wanted a very specific example of how our application worked. We sort of talked about how you could, say, hook into zoom and then transcribe and analyze that call and then the value that was coming out of it. And so that was, you know, we thought we answered a lot of questions relatively succinctly. I think our answers at the start were much shorter and more concise, which was a goal in what we had heard over and over again for why Combinator interviews, which is like, try to answer, I’m sorry, try to answer as many questions as possible and and don’t worry about.

Answering them like in super in depth because you want them to be able to ask as many questions as they can get through and give them good responses to those. Whereas if you could easily waste, you know, 2 minutes responding to a specific question and then they don’t get the answers that they’re looking through in this interview. So I think we actually started at high volume, quick succinct responses right at the start and then slowly I fell into my own ways and those and started to answer in more detail and I think you know and also I’ll talk about a little bit more sort of not tension. Ratcheted up, but confusion or questioning required or answers required. I started to sense that and be a little more, you know, just fall out of that plan state and you know, default back to my own way, which is if you’re watching this video, you can see it’s filled with lots of talking, sometimes talking very quickly and over explaining things that probably don’t need that much explaining. So there you go.

The couple of things that you know and then along with like that specific example. You know first of all I felt unconvinced that that moment and then we sort of talked about you know he wanted to go deeper into who these customers were. And in a way we at that time and I would say still don’t struggle to start articulate exactly who our customers are because of the platform we’ve built has multiple sort of job titles and use cases that are part of our system which can be a strength, can also be a weakness depending on how you look at it. And so when we describe those customers and. Again, you should be able to define this very clearly, as clearly as you possibly can. I think that that wasn’t as hard hitting as he thought. It wasn’t as specific and detailed as he wanted or as what they had seen in patterns of YC companies who have been successful. I knowing their customers, talking to them to an ongoing basis and sort of adhering to this mantra of like make something people want, talk to your customers, build something that your customers want, something that your customers need. And so you know there were other questions that emerged that were very specific to.

US and I think that’s wells as CTO of the company. His sort of feedback or thought was that he was surprised that there weren’t more things about sort of the product itself. There was only really 1 technical question about the transcription and how do we do transcription. Do we have an insight into a way to make it speedier or cheaper than others. And I think that spoke to you know look reflecting back on it to a saturated market that maybe that he had concerns with and I’m sure that he knew other people would have concerns with other investors and everything and.

I think overall spoke to this idea that from a high level he’s saying thousands and thousands of applications and that there were a lot of people interested in the same problem space. Maybe not with the exact same solutions as us, but interested in that same problem space and with that, not enough differentiation, not a big enough Moat and a challenge that could be there. So, you know, well, though I would say Michael is a very calm person. That’s when I talk about both is how once we actually got talking. Why?

Sort of went a little manic and haywire. I actually did feel relatively calm. He induces that feeling. You know, it can still be relatively challenging and intense, and he really doesn’t want to deal with bullshit. He wants very clear answers. And I don’t, you know, don’t try to input any technical jargon or anything like that. That is unnecessary, which, you know, sort of did multiple times. That is just going to ratchet up and create more attention in that call and really end up leading you to what was likely not be accepted to YC. And you can be, you know, with so many companies applying, that’s a very high likelihood that just a couple instances of that could make you.

And lose trust in you as a founder and someone who needs to articulate your product and solution to customers that that might not work out. And I think that’s a valid concern and something that we’ve continued to try to get better at. And so make sure that you can explain your product clearly and demonstrate that you’re able to articulate this to customers. Because in the end, especially considering the market environment that we’re in, you’re going to be able to need to sell to customers and convince them that your product is worthwhile. And a lot of times, the simpler you can do that, the better so.

You know, a couple. There’s one thing that I wanted to sort of talk about here, which was a super interesting part, and I would say about 3-4, but three quarters 3/4 through the interview I sort of ended up, I don’t know exactly know why. Talking about a little bit of my sort of personal journey about how I had started speaking I and how some of that had actually come from sort of a mental health perspective and wanting to sort of quantify and analyze the language data that I was creating. Some of it through Evernote, some of it was through audio and video recordings, etcetera, etcetera. And how, you know, at the time I was using Evernote. And I wish there had been a system that had automatically analyzed those notes and helped me understand myself better. And the thread that I had tried to tie through is that, you know, the system that we’re building is capable of helping people.

They’re both personal and sort of professional development and and then what was revealed and you know for the questioning is that WOW we’re super interested in sort of this personal analytics part. But really none of our, our revenue had come through that and all of our revenue had come through more of the sort of zoom transcribing and analysis and you know more customer business oriented solutions using our same platform. And then you know what emerged in that was sort of this. Encouragement from Michael to. And the feedback is basically this encouragement to follow.

The more personal analytics path because. They had heard pitches similar to what we were talking about from the business side, but they had the way that we were talking about sort of how I used it for personal analytics was quite novel to them and something that they were actually super interested in. And Michael had actually been talking about this on Twitter and stuff publicly about using systems to help understand ourselves better and then improve atomic habits and things like that. And then there was, this is where this really sort of interesting conversation came out and I I would say like a challenge that then to me is a little bit of a foreshadowing in the market environment. And then people sort of talking about why Combinator being, you know, at least partly responsible for the overvaluation of companies and startups. And basically, you know, the feedback and the final e-mail was that you are, it seems like you’re running two companies or you’re, you know, you’re pitching one thing and you’re building another thing. And I believe in that. You know, I believe in that.

Message that he actually gave back. I also believe that I know we were trying to build almost like a horizontal product, you know, product that allowed us to do these two things. And I think at the time we also didn’t understand some of the limitations that we were going to then face moving forward, whether security or compliance or the difficulty of analyzing personal data, all these things. But he sort of encouraged us to follow that path and I said, hey, I’m you know sort of self funding and bootstrapping this company and if we didn’t have any customers paying us to do this, we would never even be able to develop the technology and solutions to then. Help maybe more on this personal analytics side. And you know I remember at this point there was a lot of frustration in the call and just this sort of recommendation of, hey, that’s what you want to do the personal analytics then do it and don’t don’t worry about the how much customers you have or how much revenue you have in this moment. Just do it and then move forward and the money will come. And you know for me from someone who had, you know not lived the life that he had lived and you know not from Silicon Valley and all this stuff that was a really sort of.

You know, difficult sort of message for me to intake because it was like, you know, to me, I come from a little bit more of like. You know, I mean middle class income and you know I’ve gone to a difficult time and I started my own company and you know if I didn’t have revenue in that company then there was no company. And and then with PKI because of a couple of the ups and downs of COVID and everything, I had taken out some personally liable loans which I’m grateful that are now paid back. But you know there was no other opportunity for me. I didn’t have the network, I didn’t have the investors, I didn’t have that. And you know from my understanding showing traction in terms of revenue and customers, it was actually.

A valuable thing. And and, you know, I don’t think I’m explicitly saying that Michael was saying, hey, go, you know, don’t abandon all your sort of work that is actually producing paying customers. I think he was saying, you know, if you’re truly, you know, interested in this vision, build it, people will come, investors will come and you will then learn and figure out how to build a sustainable business that can get customers. And I, you know, I have skepticism around that and I think a lot of the companies that have gone this route are probably really struggling right now or just. Relying on VC money and burning through it. But, you know, I think this was, you know, for me one of those moments where I sort of deviated and struggled with the message that Michael gave us in that interview and sort of reflected on it. After that. It, you know, if it hadn’t been for some of those customers and some of the work that we had done to make sure it worked in the business and team perspective that we wouldn’t have even been able to make it to this YC interview, there would be nothing there. So.

You know, overall, I think this was, I mean, I’m at 16 minutes talking about this right now. It was a, you know, I could talk, you know, on and on about little pieces that that came from it. But I think I’ve hit a couple of the, you know, the pieces here. And, you know, this is not an interview of like how to prepare or not like a video on like how to prepare for a YC interview because first of all, we didn’t get in. And so I don’t think I’m in the state to make that recommendation. I just wanted to sort of share my experience and I’ll read sort of the final feedback that we got from Michael and I think.

That brings in his perspective in after I’ve sort of given some of my perspective. Was the final feedback was this was a tough decision because we really liked how passionate were. You were about space and you’ve gathered good usage and revenue in a short time. But our major concern is that you had multiple use cases that were not clear. I agree with that the consumer B use because we’re so different from another. It seems like you were running two different companies encourage you to choose and double down on the one you’re most passionate about I do think you know so that was sort of an e-mail that came from Michael after at the time we had been after the call that’s when I had reflected and we were actually overall relatively optimistic about.

Being able to adapt to the 10 minute, you know, sort of the path that we were thought we were going on and then the path we ended up on, we thought that we might get called in for a second conversation. That conversation never came and then we had received that e-mail. We, you know, responded to it politely and you know, did not push back too much even though we had seen people then. You know, definitely more attention in that call than I had sort of experienced. Even with talking to other investors, Michael had shook in his head multiple times.

Part of that was just me. At one point he said, you know, hey, you got can you explain this to me as if I was your mom? You know, so there was definitely signs for us that we had not treated the same path, although we had actually done some good things and, you know, with our reflection list them back to a reflection of the bats. And I took and after we did the call and, you know, we had all, we both felt we’d answered things pretty well and as best we could considering everything and so. You know, definitely it was a deviation of a path.

That we you know didn’t necessarily know that we were going to go on. We didn’t know if we were gonna get that YC application we had applied multiple times. I think that one was actually one of the quicker applications we had put in but I think are sort of growth trajectory at the time was really good. I I’m interested to know you know if you are first of all if you’re applying and you’re having an interview. I’d love to hear a comment or something or send me a message if I can give any other insight I would be happy to you know considering everything I’ve shared here I’m interested to know how.

You know is there. Is there a change in it? Like there’s been some articles like this, why, why commentator still paranoid. And obviously there’s been this sort of letter about, you know, the changing environment. And I’ve been lucky enough to talk with other people who are, you know, in sort of positions of startup startups up some with good traction, some early, some with a little bit of traction and the challenges of fundraising. And, you know, we know that interest rates are going to continue to expand that there’s a lot of things happening in a macro economic environment that.

Could have an impact on this for several years to come. And although YC is, you know, seeming to honor their increased investment of $500,000 there, you know, relatively taking smaller cohorts and I’m guessing that they are sometimes prioritizing other things over maybe things that they had prioritized in the past and so. I hope you give you some insights. This was my sort of own perspective of interviewing with Michael. I’m grateful for the experience. You know, to me it was life changing even though it didn’t turn out into us getting into NYC. And you know, I wish, you know, in many ways I wish that there that had happened. And I think that if we had done a couple things differently, that would have been a path that we had gone in and life would have been much differently. But I also think that, you know, as much as I sometimes struggle to deal with this.

Uh, life is, you know, sort of what it meant to be is meant to be and I’m glad to have the life that I have now, the beautiful partner, beautiful dog and still a business that is growing and generating revenue. While you know, maybe some other companies that you know took that route, they over optimized on VC money, never really truly listened to their customers and built tech and now that is very difficult to execute on or maybe they raise that revenue multiple. That was absolutely insane that they are not going to be able to hit. And so there’s going to be a lot of scrutiny and a lot of chaos as that emerges where we’re obviously in a different spot here at PKI. So thank you so much for checking this out, this mentality, briden, the co-founder of a company called PKI. We really look at like language datasets and try to extract insights from them as quickly as possible with little as code as possible. And I think we’re doing a pretty good job of that. Lots more left to do, but it’s a super interesting space and we’re super proud to be a part of it and appreciate you checking this out. I hope you have a great rest of your day.



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