Rejected from UChicago's accelerator, but accepted to YC
An interview with SimCare's Vrishank Saini
Vrishank is a former UChicago Neuroscience undergrad who dropped out to build SimCare.
This interview is lightly edited for clarity.
Taking the leap
Diego Scanlon: Welcome to Windy Founders. I always start off with a question that is definitely vague and broad, but it’s intentionally that way, so interpret it however you want. What led you here, and where is here?
Vrishank Saini: I’ll start with what led me here — I was on the pre-med track for quite a while where the forecasted path is 12 to 16 years of education. Then I made an incredibly stark shift to leave school, albeit a leave of absence such that you can return, but to pursue the company we had started with incredibly low funding – when we dropped out, we had 10 or $20,000 and a rejection from YC for S24, which is the batch we later that we got into.
But the decision to drop out was an incredibly easy decision because we were, on one level, convinced about what we were doing – not necessarily the idea we were working on, but the conviction that our team could figure something out. But it was also a low hanging fruit – if you ask your parents what their biggest regret is, maybe they won’t say this explicitly, but it’s something they’ve thought about, it’s not acting on the dot com wave or App Store wave when it was a thing. So AI was a low hanging fruit and it was almost a no brainer to pursue that as opposed to what is largely a structured path.
That led us to entering into a state of exploration and experimenting, which represented a hypothesis about the world where if we could get x amount of nodes close to whatever we imagine the world being with our technology in it, that would be a much more exciting thing than a risk averse path of education. So that’s what brought us here and that’s what here is – running a series of experiments, getting some learning out of each experiment, whether it be a success or failure on paper, and then continuing to explore. I think there’s hyper learning to that as opposed to what one would do sitting in an Econ class, no offense to anyone. So it was fundamentally about exploration, and that’s where here is today – still exploring, experimenting, and hoping that the compounding effects from our experiments pays off over the course of the startup.
DS: I think it was Paul Graham who said a good company or idea comes from an external stimulus hitting a prepared mind. There seems to be a parallel here of a technology wave hitting a prepared mind, a risk tolerant one, which leads you to become a founder. I’m interested in why your mind was prepared that way, so risk tolerant and ready to ride this AI wave.
Note: SimCare is conversations with AI patients for better clinical training.
VS: I think I was quite risk tolerant for SimCare because I’ve worked on startups in the past; I’m a previously exited founder and have done some other cool stuff. So I knew what it was like. But I was on a risk averse path before all of this, primarily because of my parents.
The burden of communicating that you’re working at Goldman Sachs or going to Harvard Medical School is trivial compared to the burden of communicating that you’re working on a startup. If you’re working on anything that’s meaningful, it’s rejected by the world. It’s not seen as something cool, or maybe it is, but it’s not something that’s tangible, or immediately in one’s field of vision. So being on that risk averse path was much easier for my parents and for myself because of that less burdensome communication of “What are you doing?” and “Are you doing something useful?”
I think there’s nuance when we’re drawing this parallel between a good idea coming from a stimulus hitting a prepared mind, and a technology wave hitting a risk tolerant person to become a founder. I think you have to be receptive, to some extent, rather than prepared. You’re accepting that there’s this void of knowledge you do not have, and then you’re very open to learning it through the process of execution. That doesn’t necessarily mean you’re prepared so much as it means you’ve accepted that your brain has this opportunity to be molded through execution.
Sacrificing school for startup
DS: We’re on the UChicago campus, and obviously we met here. I think the first time we met was last year at a founder brunch hosted by Windy Ventures.
VS: (laughs) I was showing you my Stripe which had, I think, $2,000 in sales.
DS: Yeah! And so I’ve always known you as a builder, not only for SimCare, but for a lot of other projects. You just mentioned that you’re a previously exited founder. And so, I know this probably feels like many lives ago, but I would love to hear how you remember balancing a startup with school work, and the experience of building at UChicago in general.
VS: There’s a very good juxtaposition of doing schoolwork, like a problem set, and then working on something that truly gets you excited to the extent that it doesn’t feel like work and you do it in your free time. If you’re tired and you’re struggling to work on the side project, it’s perhaps not a side project worth pursuing. I remember going to my Organic Chemistry midterm, and doing psets, and just absolutely dreading them when put next to something I love. I really do enjoy school. But when it was put in a position where I’m comparing it with working on a startup that was very meaningful and was taking up my entire time, I had to make sacrifices early on. So life became a testing ground of sacrifice – what is meaningful to you and what is not, and how do you prioritize different things. This action of micro sacrifices speaks to what you should be doing. The balance was tough and I think it being tough was very good because it showed me how much the startup meant. It showed me that I should prioritize things that I truly and deeply enjoyed, and that I should take it to the next level of sacrifice and commitment. So you can’t balance it and I’m very glad that I wasn’t able to balance it.
Candid thoughts on UChicago entrepreneurship
DS: What was building in UChicago like in regards to the resources that were available to you?
VS: It was pretty bad. I would not recommend any entrepreneur or aspiring entrepreneur go to UChicago. That being said, like I'm very fortunate to have come here, it's a very high ranked school. But I think people at Polsky, and people here in general, are very quick to give advice. Even some of the smartest founders I’ve spoken to don’t feel qualified to give advice. I think it should be more about just sharing your experiences and letting that be interpreted, rather than enforcing a series of principles that should be stuck to. So that’s the first layer of it. Also, most people at Polsky don’t have any entrepreneurial experience, and that’s fine. You’ve lived your life as you wanted to. It’s actually similar to investors – I didn’t even want to entertain conversations with investors or analysts that weren’t founders or had built something in the past because they try to use these MBA principles to apply generalizations to your market and what you’re working on to prove if it’s good or not. That’s just not how it works. So there’s a layer of lack of experience.
The other thing is I don’t think UChicago has a very founder-first investment thesis. You shouldn’t care about what the person is working on, you should want to just invest in them. And CNVC is a pitch competition. You spend three months refining your pitch, that’s nuts. You talk about projected revenue as opposed to actualized, or you built this slide as opposed to talking to your customers and building product, the only two things you need to be working on. So what you’re indexing on is a huge problem. I’m not saying this because we didn’t get into CNVC. If you look at why a company has longevity, it’s not based on a 10 year revenue forecast. It’s “Do the founders have founder-market fit? Are the founders the best people in the world to work on this problem?” Fuck the product. I don’t even care what you’re working on. How do you work together? I bet you can have a really high returning investment vehicle by not even looking at a pitch, but just talking to the founders. That was the same basis on which Tiko and I decided to pursue what we did quite early on with low signal. So I just think that people are indexing on the wrong thing. My conversations with a lot of ex-founders, amazing ones, that are at Polsky, have been around a similar thing – their thesis is very traction dependent, or dependent on signals that don’t require critical thinking to interpret as good or bad. I don’t need to be Ben Horowitz to determine if a million dollars in revenue is good or bad. It’s obviously pretty good if it’s early on. But I need to be the best investor in the world to determine if you are a founder that will give 110% and make this high conviction bet.
One of Polsky’s new investment vehicles invested 250k in our seed round, and they did that in a 10 minute meeting. I didn’t even pull up a pitch deck. So I think there needs to be more of that. I’m glad they’re working towards that. But at the undergraduate level, it’s not great. I think they’re indexing on the wrong thing.
YC rejection and personal conviction
DS: As you mentioned, you eventually said “no more” to schoolwork and went to Y Combinator.
VS: To add nuance to that – we got rejected from YC’s Summer 24 batch. You’re not allowed to apply to the same batch twice. So we knew going to San Francisco that there was zero way we were going to go through YC. We had next to zero funding, so we also knew that we’d have to sleep and work in our apartment, and eat the cheapest shit ever just to make this work. And so even in the face of a thousand nos, we saw such high conviction in our founding team that we could – there was some space we wanted to operate in and there was something to be done there.
So it’s insane to me that someone who is written a check by an investor who truly believes in them is unable to make the commitment with that much backing and a signal that this is something worth pursuing. That’s why it’s wild to me that people in CNVC just come back to school the next quarter. If an investor has such high conviction that you can do something amazing, and gives you a few hundred thousand dollars to play with your idea, then why is your biggest worry a pset, unless you are not incredibly engrossed by what you’re working on company-wise. People should ask themselves “Why am I prioritizing x over y, and how does that speak to the longevity of what I’m trying to do?”
Breaking the rules of YC
DS: My previous question presupposed that you guys already got into YC when you made the move to San Francisco, but that’s obviously not the case.
VS: We moved into our apartment, and Tiko was sleeping on a couch, I was sleeping on the bed, and Lukas on an air mattress, and we’d rotate every night. One day, a different founder friend comes in and randomly has 200 meetings booked with different VCs – he had also got rejected from YC Summer 24, but YC had extended their deadline by a week (because they had renovations going on at their headquarters), and during that week he got an email from the partner that rejected him saying, “Hey, I’d like to talk a little further, even though we rejected you.” We saw this as an opportunity to apply again, so we created new emails, a new YC account, and applied again a week before the deadline with a new domain name that we had just bought – we said, “A new domain is 200 bucks, that’s nothing to apply again.” We heard back about an interview two days later. Funnily enough, I was on a bus when we heard back and I screamed. But anyway, we got the interview.
The second we joined this interview, they said, “Look, we know you applied again. You’re not being ethical to YC.” They were grilling us. We were not expecting to navigate around that conversation, so we were incredibly depressed right after the interview, which was only 10 minutes, because we thought it was a serious pursuit of questioning. They asked us about our company and our team, but they seemed clearly upset that we were trying to game the system. So we spent the rest of the day walking around SF, just completely destroyed because we were so excited and it just came crashing down in 10 minutes. We were at the Ferris Wheel at Fisherman’s Wharf, just laying there, and we got an email from the partner who interviewed us four hours earlier saying, “Hey, I have a quick question, can you hop on in 20 minutes?” So we run to the Salesforce tower as fast as we can where there’s a WeWork, we sit down, we take the meeting, and he tells us “Our healthcare partner thinks that your work is terrible.” So he’s just grilling us more and more, saying our market’s too small, and everything he’s saying is indicating that this is a huge waste of time essentially. And then he stops and says, “Welcome to YC.”
That just completely changed our life and our vision for what the next year would look like – the next day we dropped out of college. But the thing we thought was impossible would not have happened if we didn’t have high conviction in the team, regardless of signal from the world. That conviction is what keeps us going every day. Fuck the idea, fuck the traction. Who cares about our funding? Do we believe today that we can somehow figure out how to build a unicorn? It’s not that we have a unicorn today, or that we're necessarily on the right path right now, but somehow we’ll figure it out along the way, regardless of circumstance.
DS: After the wire transfer hit, did everyone get beds or were people still sleeping on air mattresses?
VS: (laughs) Yeah. But the timing of getting in was a bit weird, so not immediately. They had the retreat right after we got in. We were the last company in the batch, we just wiggled our way in. So there was zero time to do anything but build and participate in whatever they had set up. That being said, we have pretty good beds now.
Doubts and sacrifice
DS: At the very beginning, you made it sound like such an easy decision to go to San Francisco, “This AI wave seems like a good opportunity, we have an idea that involves AI, so we’re just going to drop out.” Then later, you say, “We went to San Francisco without even being in YC, we had $10,000 in your bank, we were sleeping on air mattresses.” I’m not too sure how to phrase this correctly, but there seems to be some mismatch of this opportunity that looks great, but the reality or practicality of pursuing that opportunity looks a bit shit and uncertain. Was it “There’s some promise of AI and no matter how bad the living conditions are or the fundraising opportunity is, we’re still going to take it”? I’m not sure what the question is, but maybe it’s: how was moving to San Francisco with absolutely nothing still appealing?
VS: Yeah. At some level, my parents are always there to pay my tuition if something fucks up. So there’s some level of privilege there. But it was just evidently clear that me and Tiko were both extremely excited about the space, the use of AI in the space, and the team. We just knew we worked incredibly well together, and it was that signal, no other variable in the equation, which is how we prioritized everything. We didn’t even get into CNVC with the same idea that we got into YC with. So yeah, no funding, but it really didn’t matter because all the best companies in the world needed to be rejected by a lot of people. Not saying we’re going to build a unicorn, but if you look at the equation that any founder used to determine if what they were working on was valuable, it wasn’t based on external things. It was based on internal properties of the team and the vision. So that was the way we prioritized things.
DS: You talk about having a close relationship with Tiko and how you both knew that this was something that you wanted to do. Was there even a conversation that needed to be had of, “Hey, are we actually going to do this? Do you have fears and worries?” Or was it just implicit in the relationship and the conversations that you were having that this is what we’re doing.
VS: Tiko had a really fun time his first year, but was really fed up with the core curriculum, and he entered his first year with the intention of doing something of higher value, for sweat equity. We had a few formal conversations about practical things, like how we would structure it and where we would live, but they weren’t about coming back to school. So we agreed quite early on that this was something that we wanted to pursue full time, and the conversations were a layer above that.
DS: Was there any part of you that was scared or nervous about what dropping out might entail and about moving to San Francisco?
VS: Yeah, I would question the decision every day, but my actions didn’t necessarily speak to that. Every day, my parents were concerned, especially because I made such a stark shift. They saw what I was currently doing as a derivative of what I was doing before. So yes, every day. And it’s worse when the MVP isn’t acting the way you want it to act, and customers aren’t responding the way you want them to. I still think about that every day, “Is this something that I should be doing?” But yeah, I try not to overthink.
DS: Do you have some answer to this? Or how do you find peace with that question?
VS: The second you start working that sort of thing goes away. The second you start executing, you almost have a muscle memory of what you’re doing is correct. So they’re very fleeting doubts.
DS: Is there anything you miss about school? Obviously you’re back on the Chicago campus, not as a student but as a founder. Is there a reason why you came back?
VS: Yeah, it’s pretty random right? Honestly, just social stuff. SF is incredibly isolating, and to have your world changed and have zero constant in that change, going from one end to the other end of that delta is really tough. While our customers were in SF, we weren’t actively fundraising and we already had a lease for a place in Chicago, so we decided that we wanted to be around our friends and continue to build here. We’re super happy with that decision, and we’re sad to be leaving now, but excited to go back to San Francisco.
DS: Besides the social part of UChicago, or in other words, since the moment you decided San Francisco was the move, what’s the most prominent thing you’ve felt you’ve had to sacrifice or give up, in order to give your all to your company?
VS: To add to the social answer, it’s not even that you have less time to hang out with friends. It’s more the types of conversation you want to have are different. Not saying one is better than the other, but when something becomes your whole life, it is incredibly hard to transcend or entertain any conversation beyond that. The domain of entrepreneurship is incredibly defined, and that’s your entire life – you want to stay within those limits in your conversations. So it’s not just about having new friends, new social circles. Again, not saying one’s better than the other. But there’s sacrifice. One level, you might want the people you surround yourself with to be productive for the company. You want to ensure you’re staying aligned with that. It’s very easy to get distracted if you’re not having those conversations.
Being college age
DS: In what ways did you feel like the YC experience was affected by the fact that you were of college age or had just dropped out of college, compared to people who worked at Big Tech before coming here and were maybe a bit older?
VS: Leaving college is way less impressive and way lower of an indication of determination than someone leaving their stable job at Google and taking a huge salary cut while still supporting their family. We had a lot of friends that were 30 something years old, who just had kids, and that were entirely shifting the way they were going to operate in the world, down one of the hardest paths ever. So it was a uniquely underwhelming experience being of student age.
The one really cool thing about SF is nobody cares about your age, nobody cares where you’re from. It’s literally “What are you working on today?” And that’s very different from Chicago or New York or other places. So I think I had a much safer and not so cool of an experience being a student.
DS: You mentioned this notion of age not mattering; it only matters what you’re doing now. I was talking to another college aged founder about whether being seen as college age affects the way VCs perceive and value you. I’m curious to hear if this is something that you’ve thought about, especially considering your recent raise.
VS: If we’re speaking specifically about fundraising, it was somewhat harder being a student. I thought it’d be easier: the younger you are, the smarter you seem. But it’s actually quite the opposite. Less folks want to talk to you. The big names will invite you to their office, but they’re likely not the ones writing you a check. You’re a kid, there’s no way you’re a second time enterprise sales founder. So that lack of experience is pretty easily picked out by investors and rightfully so. I would be very hesitant to write a kid a check because they have so many other options. If something doesn’t work out and they don’t know what they truly want yet, it’s harder to have that conviction.
Selling
DS: I’ve seen you at the MAAD center on cold calls, so I’m curious to hear about this age question as it relates to selling, especially considering the industry that you’re in. I’d imagine people might want to see some credentials.
VS: If you’re selling into healthcare, there’s huge domain expertise required. Right now, we’re building software that is listening in on real patient-provider interactions. So to be a kid is super tough, and I think that really goes for any industry, but healthcare and academia particularly, where experience is I think overvalued, but valued nonetheless. That expectation makes it easy to question yourself on if you’re communicating a market and the pain points in that market correctly. But it’s also pretty cool that no one else in this entire industry could figure this out, or no one has thought that this problem is actually pretty big. It’s pretty cool that you’ve developed unique insights, and it’s insane that this 40 year old medical educator has not thought about the inefficiencies of traditional training. Or maybe they have and didn’t execute on it. So that’s a huge plus for us.
DS: It seems like there are two ways for a client to interpret your age. It’s either “Who is this newcomer who knows nothing about the incumbent medtech space?” Or it’s “Here’s this super young guy who knows everything about this emerging AI space.” What have you learned from selling, or how have you learned to sell to these customers?
VS: This answer is going to be separate from age. Before I thought of enterprise sales as something that you can close within a single call. I didn’t think you had to think about the playbooks and funnels. When you sell, you have to say this person will ultimately reenter the funnel and buy this at some point – it might be now or it might be later. And so you have to work through sales as this humongous funnel with different nodes. Those nodes might be a discovery call, a call with a lower level person, with IT to talk about integration, with budgeting. I’ve had to narrow my focus not to if the sale is made, although that should be your KPI, but a series of things that need to be true in order for the sale to be complete. What needs to be true in order for this sale to move towards the next node? It might be having data security and SOC2 compliance in place. Breaking that down into different nodes is super interesting. It’s focusing in on different steps of the funnel, and treating sales meetings as such. That’s been a complete game changer, especially for the way we quantity progress because sales cycles are six months to two years. It’s crazy and super different from what people build in college. What most people build in college is either very anti-revenue, or it’s expected to be bought on a whim by some consumer. So you really just don’t learn that ever in college. I had no idea what sales was like before.
DS: You’re moving back to San Francisco in two days. Why?
VS: You’re from San Francisco. It’s a completely different world. The rate at which you can move is insane. Practically, we also hired, so it’s good to build out an office somewhere, set up an HQ. But the frequency of people you meet doing something that gets you incredibly inspired is completely different in SF than here. That being said, if I was doing logistics, I might stay here in Chicago. So I’m not saying people are more inspiring in San Francisco, but to the thesis of building our company, it’s huge.
Change and happiness
DS: Yesterday, I was reading through these questions and a common theme seemed to be change. You’ve been through all of these experiences, dropping out, going to YC, raising money, that I’d imagine have made you mature a lot, and I’ve seen that maturity. I just remember last year, when you and Tiko pitched us in some random Reg room when you guys were trying to raise a pre-seed. And we gave you feedback which you said was helpful, and then a few days later you called me saying that someone offered you a few grand and I was super happy for you. And now, I see you in MAAD talking to customers or making cold calls, and I read about you raising a few million, and I can’t help but think you’ve outgrown us in the best way. So you’re still the polo sweater and chain wearing, pierced ear, pearly white and kind smile Vrishank I always remember, but you’re also someone completely different. So I’m curious to hear, and this is going to be a super broad question, how you’ve seen yourself change in the past year?
VS: I think I’ve matured a lot. Something I just touched on – I would be incredibly quick to give advice a year ago because I had found some little success in entrepreneurship quite early on. Now, today, I would be extremely resistant to do so because I’ve had the opportunity to interact with so many people, not in a humbling act, but more in understanding that there’s a thousand different approaches to the same problem. I think that’s maturity too. The other thing would be I’m much more receptive and willing to learn now that I was before, and that sort of ties into giving advice versus sharing experiences. It’s allowed me to mold into different roles. As a founder, I’ve had to set up payroll, and pay our corporate taxes, and build this entire MVP, and fundraise $2 million, and deal with an interpersonal conflict between two employees. You have to do all these different things, and if you’re willing to learn through that, you start to get this incredible diversity of thought, which is a path towards maturity, and become uniquely molded.
DS: Do you think how you’ve changed as a founder is different from how you’ve changed as a person?
VS: I think they are one in the same. There are practical things I can point to of how I’ve changed as a founder, like I know how to raise a successful seed round and how to talk to customers in our markets. That again has all been just inherently driven by a personal openness to learning new things, and acting in different ways, and that being prepared is incredibly overrated. It’s the most overrated thing ever, because you’re never going to do it correctly. It’s just how do you minimize how incorrectly you do something. These experiences and mindsets were driven by a want for personal maturity, and has driven maturity as a founder as well.
DS: How happy are you?
VS: I’m the happiest I’ve ever been. I feel like I will never be happier than where I am right now. That state of happiness is not at all dependent on the quantifiable components of what’s happened in the last year, but just more on my outlook on life. I would have never achieved this state of understanding, how I see the world, had I not gone through this experience. And so I’m the happiest I think I’ll ever be because I’ve understood things I thought I’d never be able to understand, and thought about things in ways that I would never be able to think about.
DS: Any last words?
VS: Have incredibly high conviction in yourself. And if you don’t, that’s alright, but don’t kid yourself on it. If you have high conviction in yourself, take whatever you’re doing to the most extreme extent because anything else is something you’ll regret in some years. If you’re going to bet on yourself, bet incredibly big on yourself because you’ll regret anything else.