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Always Be Learning
From finance to advertising to law to tech, Jared Cohen's career path is anything but ordinary. He shows us how his desire to learn above all has helped him build an extraordinary career -- and spells out specific things you can do today to improve your path.
Jared mentions Harvard’s free online Introduction to Computer Science (CS50) course, which can be found here: https://www.edx.org/course/introduction-computer-science-harvardx-cs50x
Find Jared’s posts on the tax impact of your startup option grants, more tips for getting a startup job and more at www.jaredcohe.com.
Jared starts off by describing his early career path:
Jared: I think I made a lot of mistakes early in my career. I call them mistakes, but they can't be so bad because I'm pretty happy today. I fortunately got off the rails I was on and figured out what I wanted to do.
My entire life I was on rails. Everyone's on rails for the most part, right? You're in education, you're getting good grades, you're going from elementary to middle to high school to obviously undergrad, because that's the path that most people follow that are in my social world, for better or worse. And then grad school makes sense for many people. And I think for people like me it can be scary to think about being off the rails of like, promotion, graduation, and all those things. Your target entire life of like grades and promotion and graduation. So that was easy.
I followed the path, went into finance because, in New York it's an easy path if you're a math and science person. Finance is just everywhere. I grew up in Queens and so that made a lot of sense. I tried finance. In some ways, it was a good fit, in some ways, not such a good fit. I was also immature and learning who I was and doing funny things. Like, I was the first among my friends to move into the city. So I got this basement apartment by the garbage on 55th Street. And it was always too hot or too cold, never the right temperature. And literally the garbage is outside my front door. And so it was a time of self-discovery, figuring that stuff out also. Just trying finance and I didn't really fit so well. I was really idealistic.
Josh: And it was right after undergrad?
Jared: Right after undergrad. Within a couple of months, I moved to the city, worked in financial consulting, and some things were cool. I love Excel, I love Visual Basic, I love that tech part. I didn't love how it didn't feel impactful, didn't feel like I was going to make a difference in the world. I looked at the people who were my bosses and I couldn't say I wanted to be in a role like that one day.
A lot of these decisions are going to sound ridiculous in some ways. Who do I think I am to quit higher paying jobs and take a job that pays half as much. What was the basis for that decision? It just makes no sense looking back now that I'm older. When I tell the story, I have that level of self-awareness of like, what's wrong with you? I'll just say that as a precursor.
So I moved from finance to advertising and decided to try to apply technical skills to advertising. Again, it didn't feel super impactful. I really wanted to make a difference. I wanted to change the world. I was young and idealistic. I thought I might run for office one day. And yeah, I wanted to have an impact. Law school seemed like a good path for that. So I applied to a bunch of schools, got into a good one, went to NYU, had a pretty good experience there. I met a bunch of smart people and I learned a lot. I wrote a lot. I wrote a silly book. I read a lot. A lot of things I hadn't done before.
I met a lot of people from different countries and a lot of super smart people. Really, really super smart people. In a lot of rooms, I feel like I'm smart, in those rooms I was like, I don't know where I stood, which is, it feels good to be like, there's a lot of amazing, talented, smart people in the world. And so that was a really cool experience.
And then I followed the parade to the big law firms, because I owed about $150,000 to $200,000. And so I went to one of the big firms. And again, not a bad experience, actually. There's a lot of horror stories about big New York firms and working too hard and working on terrible cases or doing things that don't agree with your ethics, or... that never happened to me. I never felt like that. I worked hard. I'm not going to pretend I didn't, because it's just part of big law firm life. Because you have to bill certain hours to make the profits for the firm and that was okay. In fact, it was probably good for me to realize that this was what it takes to succeed in life. I put my head down and I worked overnight sometimes, and for days straight sometimes, and billed my number of hours that I had to. And I was good: do this, work hard, get where you got to go and this is what it takes. So that part was good.
I got in good with a couple of partners and got to do a lot of interesting cases, and it ended up being a pretty decent experience. But fourth year, fifth year rolled around and I was stepping back, and I was just thinking, I couldn't see myself doing this for the next 30 years. It just didn't feel right. And again, I say this with a perspective of, I'm making a lot of money, working long hours but not insane hours. Who do I think I am to be able to quit a job like this and do whatever I want?
But I'm going to live once, and I was like, I got to take my shot now before I have a family and kids and get stuck in, they call it the golden handcuffs, with the money and the career I had to have. So fourth year, fifth year rolled around, at this point, I'm obviously a little bit older too, so I can actually take the time to step back and think, what were the common themes in my life that I have enjoyed? What do I actually want to do, versus, earlier on, I was bouncing around, like, let me try finance, let me try advertising, I'm going to go to law school.
At this point I actually took a step back and I was thinking, what are the themes of my life that I have enjoyed? Technology kept coming up. Even at the law firm, I was writing Visual Basic code to do SEC filings. I was doing some HTML and CSS to try to pick up some of that stuff. That technology side was important and I had some evidence that that made sense for me. I had less evidence of the other part, which is that I thought entrepreneurship and start-up stuff would be interesting for me. Like a lot of people had a small business growing up. That was something. But it was really just a feeling.
Start-ups were in the news all the time in those days, and I was reading about them, it just seemed like I wanted to build something. I started applying for legal and HR jobs at tech companies in New York, mostly start-upy stuff, but if I saw something in a bigger company I'd do that too. Initially I got no response. And it was my terrible job applications. I was taught my entire life by career centers and people in this world that my grades are great, and my schools are great, just let them speak for themselves, and write a three sentence cover letter that says, here's my resume attached, and let it happen. And that works at big banks and big law firms for the most part.
It doesn't work at tech companies and the start-ups where culture matters and they're looking for different people. And they probably get a thousand resumes from people like me who were at big banks or big law firms looking for a career change. I know that is the case, because I got them when I was at Kickstarter from people like that. And I would respond to them sometimes to try to save them, because I wish someone had tried to save me when I needed to be saved.
Josh: What were some of the things you said?
Jared: Back then if you emailed me cold, or I saw an application, I was like, this person seems a little too much like me, I should help them. I would tell them what I would have loved to hear myself, which is basically how to apply [to these jobs].
I read a blog post on this later about how to get jobs at start-ups. But basically, you need to be a cultural fit. You need to find ways to stand out, because there's a lot of people like you in the world. You need to show ambition, show who you are, show your personality, show your drive, do a class on the side, have a blog. One of the lawyers I ended up hiring at Kickstarter, she had a blog. I thought it was great. It set her apart. Even that small thing was big enough to get me to get back to her and that does matter. So whatever you need to set yourself apart and stand out from that crowd of many many bankers, many many lawyers who want to get into cool tech start-ups. It matters. And hopefully it shows who you are and that helps them hire you at some point.
I was doing the same thing. I was saying that, if you email me cold, I would take your meeting and I would just sit with you for half an hour. I should have figured this out, to do some networking, try to get some help. But I was just sitting there, like application after application, getting ignored. So I was trying to do unto others as you would have done unto you. And so I would just take meeting after meeting, giving some guidance or phone calls or responding to emails, or things like that.
Josh: So you were sending resumes into a black hole. And this is 2009, 2010, something like that?
Jared: Yeah, probably 2008, 2009. So the economy wasn't great. But the law firms generally do fine, whether it's up or down, because there's always work to do. So I was doing that over and over again, and finally, I applied for a Head of HR job at Etsy. I always loved Etsy. I own the website ImagineAndCreate.com because I wanted to build companies kind of like Etsy at some point. I was forced out of my pretentious application resume cover letter box because they asked for two essays with the application.
They called me in and the person who called me in, whom I'm actually friends with today, I did not become friends with right away, but we're friends now. He said, you're not exactly the right fit, but your essays were the best we saw, we had to call you in. And I was like, thanks, I'd love to stop by. So I went in with my suit and he's like, what are you wearing? I said, I'm wearing a suit. I said, I don’t know, I was very confused. I said, my tie's in my inside pocket, so this is business casual for me.
Fortunately got past that and I got through round and round of interviews. And it was a great experience. I got to meet amazing people and it's just a great company, great people. I didn't get the job in the end. They hired someone who had way more HR experience than I did. But besides that, I had a great experience. And so I used it as research. Every interview, I had tons of questions about who they were, what they're team looks like, what the company looks like, what they do every day, all that stuff. And what that proved was that I wanted to be in a place like that.
So after that point, number one, I knew how to send a better job application. I knew it wasn't just about my resume and my grades. Those matter, but it's really about who you are and your personality and can you solve any problems a start-up needs solved. I also realized that I had to be somewhere like this. I want to be working with people like that, building things in that creative environment, that tech environment. I decided that I would do whatever it took to get a job somewhere like that. So I started applying for any entry level job at any tech start-up kind of company in New York or California. I started getting some responses because my applications were a little better, and eventually got a job in California doing entry level data entry. And I moved out there, packed two suitcases...
Josh: So you went from being a mid-level associate in a New York City law firm, and you said, okay, now I'm going to be a data entry, entry level person at a start-up in California.
Jared: Yeah, yeah.
Josh: What's going through your mind?
Jared: Yeah, it's funny to look back at moments like that. I think people generally are just like, you're so brave, you're so courageous. But on the inside, number one, I don't feel brave or courageous. I think that's a ridiculous thing to call it.
Maybe part of it was, I should have thought harder about it and I was crazier than I realized. But it just was like, no, I'm going to take my shot at this. And at worst I could have gone back to the firm and went back to making what I was making before. So it wasn't an existential threat.
I took an 85 percent pay cut and packed my two suitcases and moved away from my girlfriend and my family and to a city I didn't know, had never really been to. And so it certainly was, that part was there. But in my mind, it just, it felt weird the morning. And I still remember this very vividly. That morning when I got up at whatever, 5am, to catch the plane, that part was the first time, I was like, have I gone crazy here. It felt very surreal. It felt like a movie. Because the sun was just rising and the sky was very blue. I was in the back seat of a taxi. Like the wind blowing into my face. It was like, am I in the movies? Is this actually happening? But again, it just felt like something I had to do. That's really what it came down to.
Josh: What did people at the firm say?
Jared: I was pretty friendly with one partner who I still see and I was having lunch with once a quarter for a long time. Just one of the best guys I've met. And I think he always knew that I wasn’t making the partner push at a law firm. I think he always thought that I was a little bit... I don't know. I don't know how he would describe me. But like, just a little bit different, entrepreneurial and just not seeing myself being a partner forever. And he certainly tried to help me consider other careers like compliance and hedge funds or places like that. So I don't think he was super surprised. I think he was happy that I was going to try something. And he was like, if it doesn't work out, I'm happy to help out. So that was always good. I certainly have some friends who followed the career path that was more typical and made partner, and some who went into different areas of law. Comparatively, it was certainly a more unusual path.
Josh: Okay. So now you're out in California working at your first start-up. Let's walk through what that felt like for you as you get in there in this entirely new role and new position.
Jared: Yeah. It was definitely a little bit disorienting, starting over like that. But I also feel like I have the right personality for start-ups, which is, I'll do whatever it takes to move something forward. At first it was data entry. Fortunately, after not too long, they could see I had more capabilities. So instead of doing the data entry part, I was building the team, finding new data sources, figuring out the process to get it and structure it and prepare for analysis. Hiring the people to be on the team. Helping to build the products that the team would use for collecting the data. So it definitely made sense in how I do things. And so my job kind of became the data side of it. And the other half ended up being some product stuff. So I went to the engineers and just became friends with them and started to ask them what they're doing everyday. And one then handed me a Ruby book and one of them wrote down some websites. And they’re like, go and learn to code, that's what we did and you can do it too. Literally, that night I went home with my book and started building a blog. And with 5 minutes, 10 minutes, I just felt like a superhero. It's such an empowering skill to be able to code.
Josh: What was it about that?
Jared: It was basically taking something that had been magic and making it real, right? If you're non-technical and you look at the web, or you look at any technology, it feels like magic. I had no understanding of how any of these things worked. And suddenly, I can make a website, right? I was using websites every day, all day for everything. And I was like, this is actually not magic at all. This is actually really doable. And it makes perfect sense. There's something about that, revealing what was behind the curtain and making it real and making me realize that I can do this pretty easily. That was really empowering and really powerful.
Every morning I was coding. Every night I was coding. If I wasn't at work, I was coding. And within not too long, I started grabbing tickets from pivotal tracker and the engineers would look over my shoulder and do some code reviewing. And that became my job or a large part of it, of doing the little tasks and a lot of fixing bugs, things the engineers don't want to do, that they're happy to have me do for them. And certainly doing some small features and things like that. But it was much more the things that they don’t really want to do. But it was great way to learn to code. And so that became a big part of my job, was that the coding, the helping to build the internal tools for my team. And it was an amazing experience. And from there on, my career made more sense. It was going to be start-ups, it was going to be technology. I wasn't sure what the roles would be. Is it product? Is it engineering? Is it operations? But I knew I’d be places like that doing things like that. So that was certainly the right time. Eventually I was happy to come back to New York. And I applied for product and engineering jobs. And I got a couple and I was about to take one. And then I met the guys at Kickstarter, and they were looking for like a mid-level ops person. And it was just... the company's amazing, the people are amazing. It wasn't like product and engineering like I thought I really wanted to do. But I knew I would keep doing those things. I keep coding in my spare time. And it would always come in valuable, not matter what I do with my career. But I couldn't pass it up.
Josh: Was it hard at that point to have taken this skill set that you had just started building and to say, okay, now I’m not going to use that in this next role?
Jared: A little bit more in the fact that I was so committed to that being my career. I was like, I'm going to be PM, I'm going to be engineer, I'm going to build product stuff. So that part, that definitely felt like a little bit of a stall for a second, like I came and I’m going to do something else. But I also just like solving problems. And I also had a bit of background for an ops role, with the finance and legal background, so it also made a lot more sense. I could have taken an entry level engineering job, entry level PM job, versus a mid-level ops job. So it wasn't crazy to do it that way. And again, no matter what, I knew that the understanding of engineering and product stuff would always be valuable. So yeah, it wasn't perfect. It wasn't like this dream in every way.
But then again, Kickstarter is how I believe the world should work. The democratization and connecting creators to their communities and building cool things that might not exist otherwise. It just is such an amazing product and such an amazing community and amazing company, amazing people. It was an easy decision. It was pretty much a no-brainer. I’ve been reading Fred Wilson’s blog posts forever. I think this guy's the greatest thing in the world. And now I'll have a chance to meet him and maybe work with him. It was a pretty easy decision in the end.
Josh: That's awesome. So you ended up moving back to New York and joining Kickstarter. It was 2010-ish?
Jared: I think it was right beginning of 2011. I think I started talking to them December 2010, maybe. It was like, December, January, February around that time, 2010, 2011.
Josh: It's really interesting. So you've touched a couple of points here that I want to get into a little bit more. So one, you mentioned that you built a blog when you were out on the west coast. And is that around the time that you actually started writing yourself? Because you've been writing for years.
Jared: I write a lot of stuff. As I was saying, I wrote a book. I do tech projects. I build things and make things. I just like doing that stuff. Number one, I just didn't think anyone cared about me writing things. I realized later that it's even more about helping me clarify my own thoughts and producing a portfolio of content, more than like I need an audience. I started doing some Tumblr stuff back then. What I first started doing was just to communicate with people back home of my experience out there. That lasted a little while. And then it just became like, yeah, no one's reading and I'm not sure I'm getting a ton out of it.
Later I think I got into like the more substantive posts. I don't know how many I've written, maybe 20 or 30. I have a document of 1,000 blog posts probably that I should write at some point. But I think it was later when I actually had a little more substance that I started writing a little bit more. So yeah, back then I did a little bit for fun, but not super heavily.
Josh: You mentioned that the person that you hired at Kickstarter had a blog as well. We're sitting here doing a podcast. There are a lot of ways that people can create content. Is there anything that you've seen people do particularly successfully or that has mattered from a content perspective that worked for them?
Jared: I don't think that the person I ended up hiring at Kickstarter did the blog for professional purposes. It wasn't professional writing, but it showed some personality. So I think it depends on why you're doing it. I think it's a great thing for people who are trying to change careers who want to show personality or build a personal brand or things like that.
Initially I did it just because I feel I actually had gained a lot of knowledge and I wanted to share it with the world. I think one of the blog posts I wrote was my career story just because I had to tell it so many times because people like to hear it. And especially lawyers who were trying to get out of law loved to hear it. So I was like, let me just write this down and share it with people. It's an easier way to do that. But by far my biggest successful blog post in numbers is how to calculate your taxes when you're exercising your options. It was something that I had to do for myself, so I made a Google sheet that you could easily copy. And it took me so long it's ridiculous. But I was like, this is something that would help a lot of people, and now I can just share it with the right person at the right time.
It certainly has helped my career. People love it or they stumble across or they find the one that they like. But when I first did it, I just want to put some knowledge into the world and get some comments.
It’s hard to just put stuff out into the world. People love to criticize. You're going to get things wrong. You're going to make mistakes. It took me some time to get over it. I'm still a little bit too much of a perfectionist. I need to put more stuff out there. But it is important to just be putting the stuff out there, to have that portfolio, to share the content, to get feedback.
Josh: I can relate that to my own experience. It’s hard to hit “publish.” You are going to get some things wrong and you are putting yourself out there and you're putting your name on it and Google never forgets. But the idea that I was getting asked these questions so many times, why don't I write it down and put it somewhere, that was a big motivator for me too.
Jared: Yeah. And this podcast you're doing is a great example. It’s just putting like it out there and showing the knowledge. It's great.
Josh: Yeah. And it's fun. Because it's an excuse to have a conversation with people I want to talk to anyway.
Jared: Another value.
Josh: So is there anything that clicked for you or that changed for you that helped you get okay with putting something out there that might be wrong?
Jared: Yeah, as I got older, I just got more confident and comfortable being wrong. And that's okay. Some of it also is just the Internet. There's a lot of wrong things out there, and I'm just going to be one more wrong person on the Internet, right? I am careful. I don't throw things out there that I think are wrong. I do my research. I go through several drafts. I have friends read it before I put it out there. So I'm not pretending. I'm strategic about why I'm blogging. Especially now.
When I first started, I just want to share some of what I've learned. Now, I'm certainly thinking, this is good for my career. So I still do it more to share, but I certainly realize I get value from it these days. Which is a nice addition to it.
Josh: What haven't you written about that you want to?
Jared: Oh, there's a million things. I literally have a Google doc that literally must be a hundred sections of blog posts. A lot of stuff is hard to write about because in the moment it’s confidential, right? There’s a ton of lessons from Kickstarter, as a great example, or Teachers Pay Teachers, or wherever in my career. But in the moment, it can be like, hey we at whatever company, are going through this traumatic moment. You can’t share everything. So there’s a long list of those that I’ll write 5 years later when it’s okay or, either I won’t use the company name or I’ll disguise it somehow. But I think that’s why VCs can blog more easily, right? Because they have a portfolio and you can disguise companies and so it’s easier. For me, if I’m at Kickstarter and I’m writing about, I don’t know, fundraising, or whatever happened to be, it wouldn’t be a coincidence, right? So obviously you have to be careful about what you're putting out to the world.
Josh: Sure. I have an email that I've been sending back and forth to myself for the last 18 months that I've been here. All the things I want to remember in real time. You're right. I feel like I could fill a book right now too. I think most people in start-ups could fill a book with the things that they're seeing. And occasionally they do, and that's probably not bright. But I do think there's a lot of value in documenting it in real time and what you're thinking about it when it happens.
Jared: 100 percent. I will actually write a lot of it down. I don't write the full blog post, but my notes are there. I'll never put out things that are confidential or sensitive, because that's just wrong, but I will try to share lessons in a format that makes sense, that is sensitive to everyone.
Josh: Yeah, that makes sense. I feel that's just good advice, maybe even anywhere, but especially in a start-up where you have a lot of things moving very quickly and you're changing priorities and changing environments and you're doing a lot of things very fast, to be able to understand how you were thinking about something at the time you were doing it. Because I can look back on things that we were doing here six months ago and I know that my memory of that is distorted based on things that I've learned since then.
Jared: 100 percent. I've gotten to know some very well-known bloggers in the world. And they do talk about how important it is for their thought process, because that is now how they think through things. That's how they process things. And once I digested that and started doing it, I understood what they meant, in that I don't need a diary on my life, but there's something really powerful about after a big event, after learning something, writing some notes on it. It helps you understand it better. It helps you learn about yourself, learn about the situation and not repeat mistakes. There's a lot of real value in that.
You can reflect for a second and it can be a fleeting memory or it can disappear quickly. But writing it down forces you to actually think it through. What were the factors that contributed to this? Where were we? What was the path? It's a powerful process.
Josh: Yeah. So you've touched on a lot of different places and pieces of knowledge that you've picked up over time, right? The finance, legal, coding, and then you're getting, doing ops at Kickstarter and growing into that. And then you moved to Teachers Pay Teachers and you take on a product role, right? And I think it might actually be helpful if you can talk through a little bit about what a VP of Product actually does. How do all of those skills come together in that type of role?
Jared: Yeah it depends on the company, but in general, you're in charge of what you build. Most companies these days are product companies, right? So there are places where the CEO and exec team should be heavily involved in product. There's certainly, at Kickstarter for example, I was doing something in legal or something in facilities, it didn't need to be an exec team discussion or decision or prioritization. I can do a lot of that myself.
Product is the kind of thing that everyone is focused on. That's where the money comes from. That's what the users are using, right? It's at the center of most things. I think being a product leader is about communication. It's about setting the road map and hiring the best people and putting them in a position to succeed and setting the right objectives and metrics and senior level planning. It actually has a lot in common with just an ops role in general, of those things I just mentioned. It's still hiring great people and managing them well and setting the right objectives and metrics.
The engineering background helped a lot. I don’t think I could have made an easy transition if I didn't have that background, so that was very valuable. But still, at a VP level, C level, the roles aren't so different between those things. You still have to be a great leader, great manager, great operator generally. There's a lot in common.
Josh: You mentioned that the technical experience helps. Is that in part just to understand the realities of what you're asking people to be able to deliver on and in different parts of the org?
Jared: Yeah for sure. I think simply put, everyone needs to learn code as a new language. And some people think you know what, you don't really need it in many of these roles. I probably fall somewhere in the middle. I know first hand the value of knowing how to code. I think that people talk to me differently. I think I can understand product differently. It even affects the way you think about anything, because it relates to legal. It's about how do you solve a problem around focusing, narrowing the problem to the smallest piece. Focusing on the root cause of something. I think it actually helps the way you think in general.
But these days, technology's everywhere. Is Kickstarter an arts company or a technology company? Is Teachers Pay Teachers an education company or a technology company? These days, everything is a technology company. Yes, of course there's education, there's arts. But you can't not know technology. So I think the best leaders of these places have to understand what you're building, right? Your product is technology. Your product is this website in many cases, or this mobile app or something like that. A C-level person probably has to have a decent understanding of that technology. So, yeah, I do think it's massively valuable.
I don't tell everyone to learn to code, but there's an amazing entry level CS course online at Harvard, CS50, that I recommend. I wrote a blog post about how to learn to code. That's the first thing I recommend. I do think people should take that.
Josh: I think what you're saying is to be technically literate, be conversant, understand what people are talking about and be able to do at least a little bit yourself, not go become a software engineer.
Jared: Right. I went farther than most, in part because I fell in love with it. I still love it. I'm not saying everyone has to go that far. But I do think that you should be able to speak about it a little bit, to understand somewhat how these things work.
Josh: One of the things that I really like that you've talked about is how you've picked up all these pieces from different places. But I think more broadly, there's a lot to be learned from sort of being entrepreneurial and deciding that you want to pick up all of those pieces and how you can do that, then synthesize it into something you want to do.
Jared: Right, that's actually a good point. I think one thing I've realized is that you are the one who's in control of your career. I think too many people let their careers happen to them. And what I realized is that it's just not going to happen unless you make it happen.
Josh: So what do you say to somebody who is trying to figure out what... there's two things, right? One is, what do I want to do with myself. I don't know what my dream job is. I don't know what my passion is. And the other is, oh, I'm saddled with debt, or I'm stuck in this job and I don't see a way out, right? Or maybe those are two flavors of the same thing.
Jared: I think the way you're going to find happiness, the way I found happiness, I think it depends on what makes people happy. For me, I am a super, super curious person. So I am going to keep asking questions and learning things and I will keep trying different things. And so while I can look back on my career and say I made a lot of mistakes, I can also look back at my career and say, I tried a bunch of stuff. And every time I got a little bit closer to where I belonged. I maybe spent too long in law, because it was 3 years of school and 6 years at a firm. Finance and advertising I was in and out, kind of 1 to 2 years. But I was iterating. I was learning what I wanted to do, I was learning about myself. And it's an important part of the journey. It got me to where I am today, which is I'm fairly hire-able as a VP, C level person in a small to mid level start-up. And that was the goal. Now I'm super happy.
I wish I had realized it in the moment. Even today, it's always going to be like that. Always in the moment you'll be anxious and nervous, but then 5 years from now, you'll be like, why was I like that? It was, I was on the right path. And things felt good. It's about the journey, not just the end point. I just wish I had people to talk to. I don't know what the solution would have been. Should I have reached out to people? But it is about taking control of your career and being curious and taking that class online or trying to code something or reaching out cold on LinkedIn to someone who has the resume you wish you had. There's a bunch of different paths. But you should be doing those things.
You should be taking control of your life early on and saying, even if you don't know where you want to go, that can be the problem you're solving today. There are ways to figure that out. If my hypothesis is, I think I'd love to be a product manager. Okay, go and find people who do that. Go and take a class, right? There's a bunch of ways to scientific method your way through that of proving things right and wrong and moving your way through to find eventually where you want to be. If you do it well, you can get there sooner. If you do it poorly, you might take 20 years. But the point is, if you do feel like you're in control of your life and you are the shepherd of your career, you are the one who are, you're making sure from every job you're getting from it what you need.
This is a balance, obviously. You are there to provide value to the company. You're here to work hard. You're here to produce value for the company. But you should also be careful, am I also getting what I need from the job? It should be a two-way street. It's not like I'm here to do data entry all day. And in some cases it has to be a side project, right? Because in some cases, you just got to pay the bills. You're doing your data entry for 8, 10, 12 hours a day. And then you go home and you learn to code. Then you go home and you do other things. And it gets even harder as you get later in life. It would be much harder for me today to do what I did back then and when I moved to California and took an 85 percent pay cut. You can do that when you're single. I had a girlfriend, but I had no real obligations. I had a little money saved from my law job. So I can go and do that and live on a mattress on the floor and an Ikea couch and a lawn chair. That was my apartment. And so, there was a time I could do that. But there are realities in the world also. And I need to support myself or my family.
Josh: So let's say you are in the same position you were in then, but you had a family and kids and you couldn't take an 85 percent pay cut and move to California. What would you tell that you to do?
Jared: Yeah. That is such a good question and makes me a little bit nauseous to think about. Because maybe it could have been that I was trapped. But let's just say I am who I am today, but I'm in that situation, what I probably would have done, it would have been a much longer and harder transition, I probably would have gone and tried to be a lawyer at one of the VC law firms. I was a corporate litigator at one of the bigger firms. I would have gone to one of the narrower firms that does VC start-up stuff. And from there maybe try to be a GC at one of those places, and then try to get a broader role, broaden to operations and finance maybe.
I would have realized that I have to take some smaller steps because I couldn't take the massive pay cut and take that massive risk. It's possible that I could have made the transition faster, but it's harder... if I had saved money for a couple of more years, maybe I could have taken the full year and done something differently. Maybe even I would have taken a full year off because I would have saved enough and just gone super hard at just engineering. That's a possibility too, looking back. Maybe I would have put my head down for 2 years and say, I'm going to save every cent. And then I'm going to pay for coding school for myself and be an engineer. Those are the two things that come to mind as maybe the best options. But that's for me personally. It depends on what they love and what they want to do.
Josh: Yeah. So what are the first steps that you tell maybe a 6th-year corporate litigator in a big firm who is saying, okay I'm not going to make partner. I'm done with this. But I want to go do something more interesting.
Jared: I think it goes back to what I was saying before which is the hypothesis approach of finding... first, find out what you want to do. Don't go leaving your law firm, right? Unless, I mean, if you're miserable, you have to do what you have to do. But you have two kids, you have a family and you're having a decent career and you don't hate it, go to networking events at night. Read everything you can. Find the people on LinkedIn you think you want their resume and go meet them. Everyone won't respond. 1 percent will respond, 10 percent will respond. But people will respond. So if you get out there, if your hypothesis is, I want to be a GC at a firm or at a tech start-up. Or I think I want to be a COO. Or I think I want to be an engineer. Whatever that is, no matter what your first hypothesis is, you can disprove that. You can go and you can take the steps to prove that's right or wrong, whether it's, again, an online class as a first step, or some networking, or some reading, whatever it happens to be, there is a way to do that. If you do that enough times, you will find, you'll keep narrowing closer and closer and closer to the actual thing you should be doing. And that's the step one, right? Because then if you know where you should be and you know where you want to be, then you can make a reasonable analysis of how do I get there, right? Can I take a bigger pay cut? Can I take longer to get there? What's the path? What did people do in the past to get to that point, right? Then you can make some reasonable decisions based on that stuff. So I think that's the approach I would take.
Josh: And for somebody thinking about maybe going into a start-up, what are some of the filters that you would suggest that somebody uses when they’re thinking about somewhere that they want to go?
Jared: Yeah. There's a couple of things... the one thing that was strategic about what I did which I didn't realize at the time was the big brand on your resume makes a big difference. The Kickstarter name on my resume, people loved it. I didn't do it for that reason at the time, but looking back it worked out really, really well. That big name in the resume is really important. It will legitimize you very quickly for every other job, for every other experience, probably undeservedly so in some cases.
You will be assigned part of the value of that success. And so I think that brand name can be really important. It can be a Google or Facebook. But because I'm not saying if you can pick the Kickstarter, then you should probably be in VC. So in some ways it kind of just happened to me. But I do think you do want to think about that. Think about the brand and how it looks on your resume. But the other thing about start-ups is that the earlier you go, the more stuff you'll get to do, especially if it's a good one. I can't speak about all of them. But many of them are meritocracies, just because there's too much to do and too few people, too few resources, too many priorities.
I'm a good example. At Kickstarter, when I went there, that was the situation. Too much to do, too few people. I did a little of everything.
Josh: Did you go there to be the lawyer?
Jared: They were looking for someone who had a background in finance or law. So I wouldn't say I went there to be the lawyer, but it certainly was a value add. My background in finance and law were very valuable. And law was a lot of what I did. I did a lot of payments and real estate stuff initially too, and law was big parts of both of those things. So it definitely was a big part of it.
Initially, when the garbage was full, I took the garbage out. When the dishes weren't clean, I cleaned them. When the door knob broke, I went to the hardware store and bought one and replaced it. When the toilet was clogged, I plunged it. But I also was running strategic level meetings and overseeing very senior projects. So that's what will happen in a start-up. Don't go there if you're too good for things because no one wants to hear that. But if you're willing to go as low as it takes, and you're capable of doing the most senior stuff, the opportunities will be there.
If you do want to go from lawyer to also an operating role, or learn other things whatever it happens to be, you can make it happen if you're that kind of person.
Josh: It's an interesting balance too, right? Because, especially if you're coming from something more established, early-stage companies are going to necessarily to give you the opportunities to touch a lot of stuff. It's also a lot riskier.
Jared: For sure. I think that's definitely part of the trade-off. And it sometimes depends on how early. And it depends on how much cash you need, right? If you can get by on less cash and a little bit of equity for a couple of years, to your point, it's more risk, but it's also higher reward. Because you will get to do more. And if it succeeds, your equity is worth more. The company could blow up and that brand could be useless, in the start-up world, people don't judge failure too harshly. But it wouldn’t look great on your resume.
Josh: Do you feel like that's different in New York than California?
Jared: It is definitely... the brand of California on failure is, people do, they value it. That was at least my take on it. That's what, if you read books or blog posts, people like to talk about it. And I think that's good for the most part. I don't think you want to glorify failure. I think sometimes people border on that, on like, it's a badge of honor. No one wants to fail. I would rather succeed. But you learn from that. You learn more from failure than from success. So I do think there's a lot of value in it. In New York, it's a different community. It is a different start-up culture in New York. It is not as start-upy. It's one of the things I like better about New York, is that it's a more diverse community. I think the cultures are similar but I'm not sure if that stands out as like being so different.
Josh: I was thinking about this not that long ago in the context of one of the sort of California-based blog posts essentially glorifying a company’s failure. I was thinking about that and the context of New York and how New York is this place of over-achievers and many people who haven't failed at all. And there is less experimentation here, at least stereotypically.
Jared: That's a really important point. I don't know if it's a cultural issue. But I think it's an actual problem. I think it's a problem for me as a person. Because I'm a father now, I have two kids. I'm so conscious of not reducing the ability for them to take risks, because it is so true. If you're getting high grades your entire life, you're less likely to take big risks. Because it would be such a disaster if you got a B. That would be the end of the world. And I think it's a real problem.
It's about trying, not being smart. I do this to my daughter, she's only two and a half, so maybe it's ridiculous. But whenever she does something good, I'm like, look at what you did. You tried so hard, you kept trying and you kept at it. Versus, you're so smart, look what you did, you're so smart. It almost makes you feel like you don't have to work too hard. It also makes you afraid to fail.
I think it's related to the start-up stuff around, you’ve got to be willing to take big risks to have big success. And you have to be willing to fail at things. So I'm not sure it's a huge part of the start-up issue, like start-up difference in California versus New York. It might be. I do that ability to fail at things is important. It's important in life and important in start-ups.
Josh: It goes back to a lot of things we've talked about over the course of the conversation: trying new things and not being afraid to be wrong and putting stuff out into the world and if you mess it up, you mess it up.
Jared: 100 percent. And being secure about that, right? It's okay to fail. Be secure about it. Insecurity is a dangerous thing when it comes to progress in the world and your career and your learning. You've got to be willing to fail. I know I'm older so it's easier to say because I was certainly plenty insecure going out and plenty lacking in confidence. But it is just so important to be secure and comfortable failing and to be open to that.
You need to build cultures, so the corporate culture at start-ups has got to be like that. You cannot overreact to failure. I don't want to glorify failure, it's not good. But you need to be taking the appropriate risk, I guess. Be open to failing where it's appropriate. Success should be learning, right? You go into this project, your hypothesis is that this will work if you do it this way. If you come out and you learn something and you fix it, and the next time or two times or three times later it's a success, that process was a success. What is your metric for success? If it's learning, failure may be a success. So as long as you're moving forward and doing that, that's what's important.
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