Episode 1

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Published on:

11th Jul 2025

I Applied to Y Combinator 7 Times. Then I Shut the Company Down.

In this podcast episode, three-time founder and startup advocate Jaclyn Siu discusses resilience, reinvention, and redefining failure with Daniel Ahmadizadeh, founder and CEO of Time.

About Our Guest:

Daniel Ahmadizadeh is an entrepreneur, educator, and seven-time Y Combinator applicant turned founder. Daniel’s journey spans teaching at Stanford and Columbia, consulting for early-stage founders, and navigating the emotional terrain of shutting down his YC-backed company.

In this episode, we cover:

  • Why Daniel applied to Y Combinator seven times — and what happened when he finally got in
  • How shutting down a company impacted his identity and mental health
  • Reframing entrepreneurship as problem-solving rather than personal validation
  • “Start With One” — a powerful framework for founders feeling lost or stuck
  • Teaching the next generation of builders how to grow confidence and take meaningful first steps
  • What Daniel is doing differently this time around

Listen now to explore the realities of entrepreneurship—where setbacks become stepping stones, and honest stories lead to powerful comebacks.

About Round Two:

Round Two, hosted by Jaclyn Siu, is dedicated to rewriting the narrative around startup setbacks, resilience, and reinvention. Subscribe wherever you get your podcasts and join the conversation online.

Looking for guidance during your own entrepreneurial transition?

Discover Starcycle. We support founders in closing chapters and opening new ones—with empathy and clarity.

Transcript
Jaclyn Siu:

Welcome to round two from Setback to Comeback. I'm Jacqueline, founder of Star Cycle. We help founders shut down their companies faster. We make the difficult parts of windup easier so that you can get back to doing what you love just a little faster. And as a third time founder, I know firsthand that the entrepreneurial journey is anything but smooth. There are highs that inspire us, but the lows that challenge us are really what sticks with us for longer. And round two is about those pivotal moments with founders, innovators and visionaries who faced setbacks head on and found their way back to a stronger and smarter comeback. Today I'm excited to be joined by Daniel Ade, founder and CEO of time building tools to help people reduce their risk of chronic conditions. Daniel has an incredible story to share that I'm really excited for all of you to hear. From applying to Y Combinator seven times and finally getting in only to have to shut down that company to now teaching at Stanford and Columbia and building something deeply personal to him. Daniel's ability to reinvent himself and stay focused on what's important, stay motivated against all the odds is a true story of resilience and grit. So grab your coffee, put on your hoodie, get cozy, and join me for other inspiring story of reinvention. Welcome Daniel.

Daniel Ahmadizadeh:

Thanks for having me. Jacqueline,

Jaclyn Siu:

Thank you for joining. And yeah, so tell us a little about you. Who is Daniel? What got you here?

Daniel Ahmadizadeh:

Who is Daniel and what got me here? Well, I'm still inventing myself. I'm still figuring that out. Jack. Love it. I think we all are. But a story of an immigrant originally from Iran. My family moved to France. That's where I was born, a Parisian souvenir of sorts. My folks came to the Bronx when I was one, and so I've been in the Bronx ever since. So I'm a New York kid who has been in the startup world for over a decade, and now I look to teach entrepreneurship while building companies and hopefully being a good inspiration for others in the process.

Jaclyn Siu:

Yeah, I'm really excited for you to share your story today. And so one of the things I wanted to start with was, of course, we're both transplants to New York, right? In Sure. We both have a lot of our formative years here, but really effectively a very different cultural background coming in, different relationships with our families who may or may not have understood where we're coming from. And of course, I'm sure, as it did for myself, it might have influenced how you look at failure and your relationship with failure. And so the first thing I wanted to start with was you, when we were hanging out, grabbing coffee, you mentioned that one of the first pivotal moments of failure you encountered was your relationship with your academic journey. You had big dreams, you had your dream school, you got into your dream school, if I remember correctly, only for you to have to unfortunately pick a different path. And that really stuck with me because it's not a part of the founding journey that people really talk about, right? People take for granted almost there's this pedigree of founders that come from the Stanford of the world, the Ivys of the world. Spoiler alert. That wasn't me either. But yeah, I wanted to take a second talk about that, your relationship with your background and how it has influenced you going forward.

Daniel Ahmadizadeh:

Absolutely. So I went to Bronx Science here in New York, which is considered one of the best schools in the world. I think we have more Nobel lts than most countries.

Jaclyn Siu:

I can't wait for you to be that,

Daniel Ahmadizadeh:

But we'll see. And so going to a great college was kind of a given. And I got into USC and that was my dream school. My aunt knitted me a USC pillow.

Jaclyn Siu:

I

Daniel Ahmadizadeh:

Was all decked out in USC gear. And then two weeks before school started, I switched to Stony Brook, a school that ended up being a great fit for me, but at the time, it was a bit of a surprise for me to go there. I was student body president of my high school, captain of the basketball team. Stony Brook was a school that would come to our high school and hand out acceptance letters when you would walk into the auditorium.

04:20

So it was considered a safety school at the time. I made Stony Brook my lab, and I decided that I'm going to make the most of this experience, and even though it doesn't have as many resources as maybe some other schools, I'm going to create those resources. So I just started building a bunch of different clubs, organizations, and we could talk about them if they're interesting, but it led me to start learning about rejection. I started the Quidditch team my second week of college. So trust me, I dealt a lot with a lot of rejection. But going to a school like Stony Brook, which is so known to produce doctors and engineers, I was so fixated on just building stuff. And so my family was very hesitant for me to go into the entrepreneurial path. In fact, even my grandma, she thought she really knew where I was going to school. She was like, oh, I've heard of Stony Brook. And then she confused it with Stony Field Yogurt,

Jaclyn Siu:

Same thing.

Daniel Ahmadizadeh:

So I was like, you know what? I'm going to put my school on the map. And there weren't too many people from Stony Brook who really made it in tech. There's John Oranger, CEO of Shutterstock, which was New York's first unicorn.

Jaclyn Siu:

There's

Daniel Ahmadizadeh:

Tristan Walker who ended up going to Andreessen, I believe, and Bevel. And then in terms of Y Combinator, at the time, I believe there was only one YC founder that from Stony Brook ever. And so it was an experience that led me to have a chip on my shoulders, even more than one I had already. So that was kind of a little bit about my story, and we could talk about how I got into VC or how I got into startups, but that was kind of the environment that I'm within, which wasn't really the startup ecosystem.

Jaclyn Siu:

I mean, honestly, first of all, I love that you were willing or you had that drive to turn something that wasn't your ideal outcome into the most ideal outcome you could have. And I think almost that would be a whole other podcast episode if we went down this rabbit hole would be if we were to say, yeah, that's actually kind of the immigrant DNA, right? We just thrive in conditions that aren't meant for us. This is a world that's not meant for us. We have to carve our own chair to have a seat at the table. And I think that's why we became friends. That's why we shared that origin story almost. But maybe we can parlay that a little bit into getting into yc because it's almost like a running joke where everyone is, everyone gets rejected from YC at least once. It's almost like a Canon event. But to do that for seven times, that is another level of grit and another very hand-on heads on relationship with failure and rejection, to your point earlier. So yeah, would love to hear about what was that fire in you that kept you going?

Daniel Ahmadizadeh:

Well, particularly in terms of YC and in general. I mean, the application is free.

Jaclyn Siu:

Sure. Thank God.

Daniel Ahmadizadeh:

Right?

Jaclyn Siu:

Please don't change that. And

Daniel Ahmadizadeh:

So the way I look at things as I'm leaving a paper trail, and same thing goes when you're emailing someone and they don't respond. You could still tell your story, you could still tell your journey. And oftentimes they live vicariously through those stories

Jaclyn Siu:

Lines, not dots.

Daniel Ahmadizadeh:

Yeah, exactly. And so that's how I look at it, is I'm not getting in or not isn't really what I'm looking for. It's also, it is a measurement of my progress in between applications. So if nothing else, the application's helpful as a measuring stick to see how well you did in between the applications. But granted, I mean, at some point they probably felt bad and they're like, we want this guy to stop applying. But for me, I have this mindset of who says I can't. I want to be a person who says I can't. So I'm going to keep doing something until it's for sure not a fit. And so your question was how did I get this kind of mindset?

Jaclyn Siu:

Yeah. Or we talked about just earlier, you mentioned you cultivated that relationship with rejection and failure. So kind of through that lens perhaps.

Daniel Ahmadizadeh:

Yeah. Yeah. Well, I mean, I would say credit has to go to my upbringing. I mean, living in New York, you're constantly, I mean, it's a tough city to make it. And seeing my parents and the rejection that they had to deal with was definite, and still having to overcome that and still having to figure it out. I think that was a big boost of confidence for me, where my mom would be working in New Jersey. My dad was in Canada for many years and the BEZA stuff and stuff. So when even entering the country, you might deal with rejection, then the rest is easy. So I think that's how I saw it. I didn't see it as a measurement of my

Jaclyn Siu:

Worth.

Daniel Ahmadizadeh:

I think a lot of people when they don't get a reply, when they don't get in, they're like, well,

Jaclyn Siu:

Discouraged.

Daniel Ahmadizadeh:

They're discouraged. Maybe I'm not as valuable as I thought. This is just going to make for great content down the line. I think all this rejection, I mean, even Michael Jordan didn't make his, isn't that the thing? He didn't make his varsity team. He got cut or something. It became Michael Jordan. So

Jaclyn Siu:

True.

Daniel Ahmadizadeh:

That became a very nice piece of content eventually.

Jaclyn Siu:

That's why he went to the nba. It's for a content.

Daniel Ahmadizadeh:

Forgot that to prove people wrong. No, but I look at it, it's all part of the journey. And I also think if you're really meant to do something, then you're going to keep applying if it's really something you really love or you're passionate about. And not to say that it's not yc, it's solving problems. If you're someone who loves medicine, you're going to keep applying to medical school.

Jaclyn Siu:

Sure. YC is almost like the shorthand for what this stands for, but it's not the only thing.

Daniel Ahmadizadeh:

And look, it is difficult. You get in and then it end does it, and end up working on at the end. Well, that's a different conversation, which I'm sure we'll have in a few minutes. But that was really my drive and maybe I should apply again. I, who knows, should keep up playing.

Jaclyn Siu:

Hey, Gary, if you're listening.

Daniel Ahmadizadeh:

Yeah.

Jaclyn Siu:

Watch out with Danielle Ade time. And this actually feels like the perfect segue to that part of the conversation because the same drive that I think a lot of great founders resonate with, and if I may say so, both of us fall into that category, but a lot of founders in general really have this almost dogmatic approach to life. It's like no one can tell me, no, I am the only one who can tell me no. Every no is an opportunity for a yes down the line. It's the stubbornness, it's eyes on the prize, blinders on that type of mindset. And at the same time though, it can also become a double-edged sword to towards let's say, when you have to make a difficult decision on whether or not to stay or to go, let's say a company is like, do I pivot or do I shut it down? That kind of conversation. And I know that this is something that you've dealt with as well before. And so how do you navigate that? Because does failure or that notion of failure affect that line of thinking in any kind of way? When you think about, do I pivot, do I give up in giant air quotes? Do I give up? Or how do you approach that train of thought?

Daniel Ahmadizadeh:

Well, how I approach it now is healthier than probably how I approached it in the past, I would hope. And what's coming to mind is when I shut down my YC company, a lot of my identity was tied into that company. And now I think part of what makes failure difficult is when it's really tied to who you are as a perk. And when you are able to disassociate the two, or at the very least, if you have more than that as part of you, then you're not left as broken.

12:34

And so my relationship with it has become well, and this is something that I tell my students, I'm like, you're not the CEO of when you're just starting out. I know you introduced me as that in the beginning. I'm the CEO of time, but the project I'm working on in reality, chief executive of what? So I think a lot of times we add so much weight to what we're doing unnecessarily and which actually slows us down. We add these labels and we don't iterate as quickly. We don't adjust. And for all I know, I'll be working on something else in three months. And so I think part of it is you're not necessarily a founder on day one, you're a problem solver. And then so if you're shut down something and you're just a founder, well, I'm not a founder and why am I, well, no, you're still problem solver. You don't really shut down problem solving. So this happens to be shutting down as the problem of the day, deal with it, deal with the next problem.

Jaclyn Siu:

And

Daniel Ahmadizadeh:

So I think my relationship at that, that's how I've shifted my mindset, is that even if I'm working on something, I try to internalize that I'm a problem. I'm a scientist. And a scientist doesn't get existential crisis when their hypothesis gets the conclusion. No, they're looking for the truth. And my thought is that entrepreneurship has to be revisited in that lens that we're scientists hypothesis to conclusion. However, it goes off to the next hypothesis, just like a scientist does. And similarly, when we're in high school and college, when we had a biology experiment, we just get it to conclusion and move on to sociology class or whatever it was. And so unfortunately, because of the expectation that we put on ourselves with this identity, it leads to this very expensive failure. Doesn't necessarily have to be, it's expensive alone to shut down a company sometimes. But if you can do that for yourself in a different lens, I think it could be healthier.

Jaclyn Siu:

Yeah. First of all, I love that perspective and it's clear that it's a perspective that's very hard earned because unfortunately, we're in the same club here. We've both had those experiences where we're like, yeah, I had a horrible, horrible relationship with failure. I beat myself up. I think we heavily relate to each other on that level as well. And kind of coming out of that and still having a sense of self and having the curiosity to continuous problem solving. To your point, I think that is very difficult for a lot of people. And I want to shift gears slightly because I know you work with, on the flip side, you work with on the other side of the table with a lot of YC founders, you also spend some time in vc. And is there something you feel like the ecosystem or other founders could be doing better for each other to help each other get to that state of mind? Or do you think it's almost like a rite of passage? Because you could argue that this is one of those things that you almost don't learn until you go through it at the same time. There's a lot at stake where almost the system almost demands perhaps that someone be maniacally focused on this being their identity, because otherwise the stakes might not feel high enough. All of these things, how do you feel about any of that?

Daniel Ahmadizadeh:

Well, what we each value is very personal.

15:52

I understand that my journey is also tied to my values. And if you value a billion dollar outcome more than anything else, then there are likely proof points that show that making that your sole focus of your entire being maybe is more reflective of that outcome. Maybe I'm wrong. So I think part of it is that part of it is what is the outcome that you want as a person, rather than what is the outcome that your investors want an outcome that the Silicon Valley wants? And I learned that through that rite of passage. As you mentioned, I very much drank the Kool-Aid

Jaclyn Siu:

Of,

Daniel Ahmadizadeh:

Hey, let's build billion dollar companies or bust.

16:35

And so I think that's part of it. The second thing that I would suggest is, or just in an observation, it goes back to the failure conversation we were having. Jay-Z said it best, I'm not a businessman, I'm a business man. And I think that's also part of it, is you making sure that you are doing yourself. If you're not bringing your best self, you're also doing the venture of the service. So how do you improve your sleep? How do you improve your nutrition? How do you improve the things that keep you grounded in order to be the best you can be for the venture, but also irrespective of the venture, you still got to take care of the house just yourself. So I think that's also part of it. And the last thing is that the measurement of success in entrepreneurship, I think it's flawed completely. And what I mean by that is we are looking at theory, oh, this is what we're going to build and it's all let's raise money. And even though we haven't actually solved anyone's problem. And so I think if we go back to that scientist lens and the objective is let's actually help real people then

Jaclyn Siu:

Solve real

Daniel Ahmadizadeh:

Problems. Yes, solve real problems. And the framework I've developed, it's called Start with one. Start with one human being. Well, if you've helped one human being, that's most than most startups, most startup founders, after months or years of working on their project, they can't name a single soul that they've helped. And so now you've spent two years of your life, millions of dollars of venture funding. And if someone asks you, who did you help? You can't say

Jaclyn Siu:

Anybody. Can't name anybody. Yeah.

Daniel Ahmadizadeh:

To me, that's failure. That genuinely is a waste of resources, your time and creativity.

Jaclyn Siu:

I feel that. And I think a lot of, again, it feels like an existential question that a lot of second time founders go through is usually after you've poured your heart and soul into the first, it's almost like your first heartbreak, right? Your first love. And how do you find yourself from here? And usually the thing I come back to, I knew I came back to it for myself and for my mentees and all of the lovely folks of the world is to your point, start with one. I'm stealing that by the way.

Jaclyn Siu:

I trademarked it.

Jaclyn Siu:

Well, I hope I get a free license to use it. We should have a copyright if we're doing our job correctly. There should be a copyright signatory here, right? Somewhere around here. But start with one. I think that is such a grounding thing because it's that saying, how do you eat an elephant? One bite at a time? It's a very evocative metaphor, but it's like how do you change the world? You start with one. I really love that framing. And so I think that puts us on a trajectory. Sorry, to talk about your work with your students now, and what are some of the questions that they're bringing up to you? What are they scared of and how do you help them out? And maybe someone out there who's listening could use some Daniel advice.

Daniel Ahmadizadeh:

Totally. The one

Jaclyn Siu:

Not trademarked.

Daniel Ahmadizadeh:

No, really, it's an invitation to anyone, to the students that I teach range from high school students to business school students. And the number one thing that I look to instill in them is confidence. And we have a confidence problem inside the classroom. And I believe really with aspiring entrepreneurs, it's the confidence in themselves that they could actually do this. And so how do you become confident that you could actually do this? You're saying that you're going to help millions of people. Well literally start with a single soul, and it pairs down this complexity of what entrepreneurship even means when you're like, wait a second, just help and give a name to that person, not a theoretical name. What's her name? Her name is, let's say Samantha Quinones. She lives on the Upper West Side on 78th Street. This is not a real person, but let's imagine. But it has to be an actual human being. And when you look to solve a problem for an actual human being, you're able to empathize with that person's problems a lot more. You're able to pare down what the solution is needed for that one person a lot. And so the students that I teach, they're actually able to find a person to help that person in the span of a week.

20:54

A week. So one example, can I share a quick example?

Jaclyn Siu:

Please?

Daniel Ahmadizadeh:

Okay. 15-year-old student, her name is Ra. She, her grandfather is in Hiroshima, Japan. Her grandfather has lost the motivation to walk, has lost the motivation to walk. So Sarra, what she did was every time her grandfather would walk 500 steps, her grandfather would get a personalized ten second video from his granddaughter.

Jaclyn Siu:

Wow.

Daniel Ahmadizadeh:

Walk another 500 steps. He get another ten second view. So she was able to use the love that she has that her grandfather has for her grandkids in order to motivate him to walk.

Jaclyn Siu:

Wow.

Daniel Ahmadizadeh:

That 15-year-old student, Serra has done more than most founder friends than I have in a week because after months or years of talking to my founder friends, I ask them, who have you helped? They can't give me a name. And I even go to demo days of founder demo days of non-named accelerators. And that's my lens of whether or not I invest in that founder or not. I ask them, give me the name. I don't understand your trucking business. Give me a name of one trucker and how did you help them?

Jaclyn Siu:

How did you help them?

Daniel Ahmadizadeh:

And if you look at Airbnb or all the companies that we admire, they all started with a single soul. Airbnb's first ever customer was a man named ammo survey. And look where they are today. So that would be the best. So that's how you gain confidence. You gain confidence that you could actually do this entrepreneurship path by first helping a single human being. And if you can't do that, then great. You learn. If you can't do that, then you go from one to two to many. And so that's the lesson. That's the lesson. And Gmail allows you to send 2000 emails per day. You just need one reply. Send the cold emails, get a reply, start with one,

Jaclyn Siu:

Send a cold email. You heard it right here, folks. But truly send a cold email. I always tell occasionally I drop into NYU, my alma mater to share a few lessons around being a founder. And I also get that question a lot. Actually. How do I get started? I always say, just get started. I am sure you know of this too, working with the next generation. But a lot of times I leave the classroom, I give my email, I give my LinkedIn, and I'm like, reach out any questions. I will always find time to talk to students. And more often than not, I hear from one person, one or two people. And I always tell them, if you just reaching out, just being that one person who reaches out and start with one, you arguably could also work there. Start with one email. You start sending those emails, you get better. And sure you're going to have that rejection we spoke of, but email rejection is probably going to lead to be the least of your problems as a founder.

Daniel Ahmadizadeh:

To build off that, Jacqueline, the one thing that I tell the students about the email grind is that they're a lot cooler than they think they

Jaclyn Siu:

Are. Absolutely.

Daniel Ahmadizadeh:

These students, these you, if you're in your twenties, even if you're in your thirties, maybe, I don't know, thirties where that

Jaclyn Siu:

Felt like a personal

Daniel Ahmadizadeh:

Attack. It's a personal attack to me. And I could say this with confidence in that I tell my students to look at the Y Combinator directory, pick a founder, pick a company, cold email them. Or I even tell them, I tell them, how many of you have emailed the business school professors at Columbia? How many of you have emailed the dean? And then we do an experiment. I emailed the dean, they emailed the dean, they get a reply, and I don't,

Jaclyn Siu:

Sorry. You're not cool enough.

Daniel Ahmadizadeh:

No, it's the reality is that people, their stories are really cool. Aspiring founder, your journey is so exciting and so many people's ships have sailed, and now they're going to live vicariously through your story.

Jaclyn Siu:

You

Daniel Ahmadizadeh:

Might think you're not doing anything cool because you're just taking a few classes at whatever school you're at. It's actually quite cool. And you're going to show in those emails what you learn and you're going to follow up. They say 80% of sales happen between the fifth to the 12th touch

Jaclyn Siu:

Point.

Daniel Ahmadizadeh:

I mean, that's the art of the game. You got to keep telling people your story. And I tell them all the time, like, Hey, let me know when I could pre-order your book, because they're each writing their story. And if you look at your own journey back to the Jay-Z quotas, you're creating content, creating content for your own business, for your own life. And so yeah, I think a lot of people don't get into entrepreneurship because they think they got to be a CEO. They got to raise money, they got to just help a person send some emails. It's not that crazy.

Jaclyn Siu:

Send some emails. That's really what it is. And I totally resonate with that, even just for myself, because on days where I feel like I can't show up as my full self with all of my brain cells, sometimes I'm just like, I'm just going to do one thing. And I think start with one is a great framework regardless of how you apply it. Yeah. So yes, thank you for sharing that and kind of refocusing the conversation back on you and what's coming next. And through all of the lessons that you've learned, especially the difficult ones, and whether it's through the start with one framework, your past relationships with or past encounters with failure, and how are you applying that towards building time? And what do you feel like this time around you want to do a little differently or just maybe that's some lesson that you've learned that you're like, I want to keep focusing on that. Other than start with

Daniel Ahmadizadeh:

One. Well, shutting down my first company was incredibly painful. And so if I haven't emphasized it enough during our conversation, it was not only an identity issue, kind of felt like I was being told by some entity I told you, so, hey, why don't you get a real job? This was kind of how I was your

Jaclyn Siu:

Internal monologue

Daniel Ahmadizadeh:

Internal. But while I starting a company right out of college, right out of college, the first thing I did was I was trying to start a company, why don't you get a real job? Wait a second, you're unemployed, this and that. And then it was like, you see, I told you so it didn't work out. And so my relationship with starting stuff, I have to be very frank with myself in terms of what my expectations are first before getting into something. And when I get into something, it has to be very much connected to me. And now I'm a lot more selfish when it comes to the problems that I'm curious about. So at the time, I was working on solving problems related to real estate, and it was a ton of fun, but I wasn't, it wasn't, wasn't

Jaclyn Siu:

Your soul problem.

Daniel Ahmadizadeh:

It wasn't speak to my soul, although I very much love talking to those customers. I really did. Nowadays I look at, if I'm working on solving problems that are meaningful to me and they selfishly only help me and those that I love, that's success. And so in, what are some of those? Well, some of those are health related things. Well, if I'm helping myself and those that I love from a health standpoint,

Jaclyn Siu:

Great.

Daniel Ahmadizadeh:

And if I don't work on something related to that, I might regret it. So regret is another framework or lens that I use to determine whether or not I want to really work on something or not. That's something that really helps with the expectation setting. What is my outcome here? Well, solving my own problems. And if it helps anyone beyond that, then fantastic. Fantastic. And so that's kind of how I look at it now.

Jaclyn Siu:

Great. And for anyone who's listening, who's probably thinking about finding that one person they want to help, or perhaps they're at a crossroads where the initial hypothesis they set out to try and solve or to prove they weren't able to make as much progress as they hoped, is there a question that you come back to all the time that grounds you, that helps you focus and redirect yourself that might be helpful to this person,

Daniel Ahmadizadeh:

To this particular person who's trying to figure out

Jaclyn Siu:

Like what to focus on,

Daniel Ahmadizadeh:

What to focus

Jaclyn Siu:

On, or maybe pick the focus but it wasn't the right one?

Daniel Ahmadizadeh:

Okay. Yeah, sure. I used to still actively consult founders, and I helped them with changing their trajectory. And one of the things that I heard from one of them was, Daniel, sometimes you give nuclear options. The nuclear thing here to say would be, what if you did nothing? And what would happen? Who would care? Would you care? Would someone else care? Does anybody actually care? And if you can't honestly say that you yourself. So if you're working on something where you genuinely believe that, at least, again, it goes back to the framework, at least someone has to care. And in order to find that person, that person could very well be you. It could be your family, it could be someone in your community, it could be someone in a different country. If you have some context about some societal thing that maybe others don't, that would be one way to think about it. And then how do you do that? It's all about environment. This goes back to the Stonybrook thing. In order for you to allow for serendipity to happen, for you to get that insight, for you to get that creative spark, you got to position yourself to be in an environment that allows for you to get lucky.

30:23

And if you're sitting at home in your apartment all day trying to brainstorm ways to help truck drivers,

Jaclyn Siu:

That's

Daniel Ahmadizadeh:

Not going to get you to that one truck driver who you're going to help.

Jaclyn Siu:

If

Daniel Ahmadizadeh:

You want to help truck drivers, go to truck, go where the truck drivers are, go in that environment,

Jaclyn Siu:

And

Daniel Ahmadizadeh:

That's where you're going to actually empathize with those particular types of people to hopefully find one person that you can actually help. So the role of an environment is critical here. If you really want to build a tech company, where are the best places to do that? If you really want to learn about a particular problem, where's the best place for that particular problem?

Jaclyn Siu:

Who is the best person you can talk to?

Daniel Ahmadizadeh:

Yes.

Jaclyn Siu:

Yeah.

Daniel Ahmadizadeh:

So that's one thing is the physical environment. Second thing is that your digital environments, your digital spaces. And the third is when you do get in front of that person you want to talk to, what is the question that you're going to ask? I have a very good question, because if you have a very good question, well now maybe that person starts thinking about who else they know that could help you answer that question. So I think a combination of those things, you'll figure it out.

Jaclyn Siu:

So simple, but so hard.

Daniel Ahmadizadeh:

And I understand that also, if you're listening to this, our conversation here today, maybe you're at a job and you're thinking of starting something, you could also do this on the side. This is not to be your full, full-time thing where you're just immersed with truck drivers all day. And if you're working at particular company, spend nights and weekends doing this. But if you're not, you're doing yourself a huge disservice. But for me personally, at this point, I like solving problems related to myself and those that I love.

Jaclyn Siu:

And ultimately, at the end of the day, you're the only one who can tell yourself no. So just take yourself out of that equation and just do it.

Daniel Ahmadizadeh:

That's

Jaclyn Siu:

A big part of it.

Daniel Ahmadizadeh:

And you can't fail.

Jaclyn Siu:

Yeah, you can't.

Daniel Ahmadizadeh:

Then there's no option to fail.

Jaclyn Siu:

Because if you are the one, then that's where you start.

Daniel Ahmadizadeh:

I'm now helping people get healthier.

Jaclyn Siu:

Yes.

Daniel Ahmadizadeh:

Reduce the risk of chronic conditions. Well, by doing that, well, if I'm more mindful of my sleep, more mindful of what I'm eating and stress, well that's great. Regardless of outcomes.

Jaclyn Siu:

Yeah. And if you did nothing, you would suffer.

Daniel Ahmadizadeh:

Correct.

Jaclyn Siu:

Correct. So there we go. There we have it. So thank you so much, Daniel, for sharing your story today and just really digging into some of these frameworks that I think are parroted or can be parroted a lot in the real world that have almost become cliches, but really grounding them in reality and what your experience has been. So thank you for sharing that. If anyone were to send you that one cold email, make it good. But if they were to send you that one email or that dm, where can they find you?

Daniel Ahmadizadeh:

Feel free to email me LinkedIn and follow up, follow up, follow up. Regardless of

Jaclyn Siu:

The reflect, don't be scared.

Daniel Ahmadizadeh:

Follow up, tell me your stories. It's not just that I'm here to read them and now hit me up long

Jaclyn Siu:

Term

Daniel Ahmadizadeh:

Because these circles are small and these journeys are long.

Jaclyn Siu:

Absolutely. And one quote I come back to a lot that Brian Chesky said at a talk that I went to was, if you're doing something right, the road in front of you is always longer than the road behind you. And I come back to that a lot, and I think it's true for so many things, but especially being a founder, it failure is behind you. There will be more failures ahead of you, and all you got to do is look up and keep going. So thank you. Thank you so much for your time. Find that one person that you want to help. And if you are working on something already, put a name and a face to that person. It really does make a difference. And good luck in Godspeed.

Show artwork for Round Two

About the Podcast

Round Two
From Setback to Comeback
Join Jaclyn Siu, 3x founder and advocate for embracing entrepreneurship’s toughest moments, for honest conversations about failing forward. Each episode pulls back the curtain on startup life—the good, the gut-wrenching, and the unspoken—to help founders everywhere reclaim their stories, reinvent their identities, and rediscover their power.

About your host

Profile picture for Jaclyn Siu

Jaclyn Siu

Jaclyn Siu is an entrepreneur, investor, and mentor dedicated to supporting founders at every stage, particularly the challenging ones. Named one of NYC’s Top 50 Underrepresented Founders, she’s built award-winning brands at the intersection of culture and technology, partnering with influential figures like JAY-Z, Rihanna, and acclaimed artists Daniel Arsham and Hajime Sorayama. Jaclyn regularly shares insights on entrepreneurship and innovation at institutions like NYU Stern and Parsons.

As the founder of Starcycle, Jaclyn combines logistical expertise with deep empathy, guiding entrepreneurs through the complex, often-overlooked process of closing businesses thoughtfully and respectfully. She believes every ending is the seed for a new beginning—and she’s here to help founders navigate that transformation with clarity and compassion.