How to Get Paid to Learn
“I want to get paid to learn. But the way to get paid to learn is to share knowledge and create something useful with that.” – James Clear
James Clear gets paid to learn. His writing on the hidden forces that shape our habits using them to maximize performance is read by over 1 million people per month at jamesclear.com.
In our conversation, James emphasizes that he is an entrepreneur; we break down in detail how he thinks about his business, metrics he tracks, how he’s scaling, and more. His product is his knowledge or, more precisely, his ability to communicate that knowledge in a way that people are willing to pay for it.
In this interview, James shares insight into applying this knowledge to your life, including:
And like James’s work, one of the best parts of the legal profession – at least to me -- is that we get paid to learn too.
Listen to the interview on Soundcloud or download from iTunes. If you enjoy this interview, please share it. Thanks!
Josh: James, you've been writing for years. And you have a pretty significant following on your website and through your email list. It would be really helpful if you can just help lay the groundwork and help us understand how you got your start in writing and how things have progressed for you over the last several years.
James: Sure. I would say I started as an entrepreneur, not as a writer. And in a lot of ways I still identify as an entrepreneur although if you think about what I spend my time doing most days, it's writing and research and reading. But I started as an entrepreneur 6 years ago. The first 2 years were spent trying a bunch of ideas that failed and flopped. Standard entrepreneur story. I look at that period as when I incubated my skill set. And there were a lot of things that are skills that are central to my writing career now that came out of that time.
I taught myself to code and program, I built my own website and designed it. The site that I run at JamesClear.com is still designed by me. Very minimalist design, which is my style, but I learned how to do it.
Building an email list: I didn't even know what an email list was when I started. I had to learn about that and how to get people to sign up, learn about conversion rates and design. And how to create products and courses, get people to buy things, learn how to sell things. Write sales pitch copy, direct response copy writing, that type of stuff.
Along that journey, I started studying consumer psychology, because I had products or businesses that I was trying out and nobody was buying a thing. I figured I had to learn how to get over that. As I studied consumer psych, I started to get into behavior psychology and habit formation and performance improvement and all the stuff, and I started using it for my health habits and my strength training habits and to study more effectively. Gradually I made this transition to writing about the hidden forces that shape our habits and lead to human performance. That was about 4 years ago, that I started writing on JamesClear.com, and those topics have been central for me ever since.
Josh: Was there a point in that process that you realized that you were getting hooked on this stuff and you were going to put some of the other products to the side and focus more on this [topic]?
James: I think there are two parts. First, I was definitely interested in it. Like a lot of people who have an achiever mindset or who are former athletes – I played baseball all the way through college – that idea of continuous improvement and continuing to try to stay on the edge of my abilities and upgrade to the next level, that naturally resonated with me.
But the second part was that I was trying to pay attention to what people found useful and practical. I would say now, one of the main things that I want is to be useful to people. So it seemed like when I wrote about those articles, they went over better than the other stuff that I was writing about. I tested, for example, a couple of iPhone apps early on. This was back when iPhone apps were a big deal, and they didn't really go over that well. They didn't seem that useful to people. But when I started writing about habits and performance improvement and deliberate practice and things like that, the response was much better. And now, my site gets over 1 million visitors a month. And there are hundreds of thousands of people on the email list.
But back then, I could measure improvement by did I get one or two emails that week. And if I heard from one or two people who really liked it, and that was more than I was getting otherwise, it was a good signal to keep going.
Josh: Did it feel like you were giving up on some of the other stuff at that point, or did you feel like, okay, this is the thing?
James: That's a good question. I would say not really, just because I wasn't doing it for that long. Baseball was incredibly meaningful to me when I finished played. I ended up being an academic All American my senior year in college. My dad played in the minor leagues with the St Louis Cardinals. It was a big part of my life for the first 20 years or so, and I played baseball for 17 years. So of course I was really invested in it. By the time I got done, I had put in almost two decades of work. Whereas in comparison, a lot of these entrepreneurial ideas, especially in the beginning, I'd only been working on for 6 months or even maybe 18 months. So yes, I was invested because I'd spent a little bit of time on it, but it paled in comparison to the level of passion that I felt for baseball when my career finished.
I think because I had that to use as a counterpoint, I was able to look at it and not feel like I was abandoning things or giving up on things as much as testing different ideas out and trying to figure out what worked. But your question is an interesting one because it gets to the central tension of life in a lot of ways but definitely of being an entrepreneur or being a writer, which is, when do you double down on something and when do you give up on something, and when is it quitting too early versus when have you cut yourself short and success is just round the corner? Everybody wants to know the answer to that question, but nobody really knows. And that's why it's really hard. And if it wasn't hard, then we wouldn't even be having this conversation about that. That's one of the things that makes it challenging.
Josh: Can we talk about baseball for a minute? I'm a big baseball fan too. A lot of times when you stop playing, it's not something that's within your control. Is that something that was, that you just hit a limit either of natural ability or did you get hurt or something, that something told you it was time to stop playing?
James: My best year ever was the last year that I played. I was never one of those guys who was the best player of the team from the very beginning. I kind of had this gradual progression where I kept getting better and better each year, so it was really hard to have to give it up. I was a right-handed pitcher. I threw 88. And right-handers who throw 88 are a dime a dozen in the minor leagues, so there would have been no reason for someone to take a risk on me as a 21 year old or a 22 year old when they could get an 18 year old coming out of high school who was throwing 93. I might have been more polished.
I was also probably at, let's say, 90% of my genetic potential, whereas someone who is raw coming out of high school is maybe at 50% of their genetic potential. So you're always going to take a risk on that guy. It was a decision that was made for me. I would have loved to play longer than I did, but I also have no regrets about the career that I had.
Josh: Is there anything you've learned about habits or deliberate practice or anything else, and your writing for your entrepreneurship career that you wished you could have told baseball player you?
James: Well, actually, it's probably the reverse. There were a lot of things that baseball player me was doing without realizing it that I wish I could have told entrepreneur James. One of the core things that I realized is that, our habits are often a product of these hidden forces that surround us that are usually invisible to us but impact our lives in very significant ways. For example, the people that surround you. It's a very common one. You don't really think about them that much. You don't think about how they impact your behavior that much. But once that veil is lifted, you have this vague notion of it, because once anybody brings it up, it's like, oh yeah, of course I do things that my friends do or I do things that my family does.
Environment is another one. The things that are on your desk at work or the items on your kitchen counter at home. These things impact your work habits and your eating habits. The technology that surrounds us. The digital modifications that you get on your phone. The way that you measure your habits and performance. These things all impact our behavior.
hat I didn't realize when I was a baseball player is that I had a lot of those things working for me without even realizing it. I had coaches and team mates that were pushing me without me really having to think about it a whole lot. I had this whole structure around my day, where, because we were going to be at the practice field for 3 hours each day, that was an anchor task that let me base the rest of my day around it.
After my playing career was done, well, suddenly the world was wide open, especially as an entrepreneur, and you get to decide what those things are. You have to choose what that anchor task is. You get to decide who surrounds you each day. You have to figure out where to get a coach or a mentor or whatever you want to call it. And a lot of these forces that I took for granted at the time, I have slowly had to discover and rebuild and create this architecture where I can actually perform and improve at a high level because it's not naturally there.
Josh: So it sounds like you described it as architecture. And it sounds like at least now, maybe you're taking an intentional approach to how you're putting that stuff around you. Has that always been that way over the last several years? Or how did that progress for you?
James: Yeah, it's definitely been a gradual evolution. I think it's true for a lot of us: the influence of those forces is always there. The system is always running. We're often blind to it. And one reason we're blind to it is because we're just not aware of it. Over the last couple of years I've read a lot about environment design and choice architecture and how our behavior is nudged by the physical environment that surrounds us. But 5 years ago, I didn't know anything about that, so I wasn't even aware of those ideas, but it was still influencing me.
For example, the items that are on the shelves at the eye level at the grocery stores tend to get purchased more than ones that are down by like your feet or your shins. Items that are on the end caps of aisles or that are on the checkout line also tend to get purchased more. It's visual stimuli. They are in a more prominent place. And the things that we see tend to be the things that we pay attention to. And so I was falling victim to that all the time, right? I was buying a candy bar just because it was put on the end cap right in front of my face. But I didn't realize that was the reason.
Now, I think I am being more intentional about creating that structure whether it's physical environment or social culture or technology and measurement. But I'm only being more intentional about it now because I'm educated about it, because I know that it exists. So it definitely hasn't been something that I've done from the very beginning. It's been a gradual evolution. And the more that I unearth and discover about how my behavior and performance is being shaped for me, the more that I can transition from being the victim of that to being the architect of it.
Josh: So it sounds like when you're describing this stuff, you're talking in a lot of ways about the habits that we already have, and understanding the drivers of what is causing us to do certain things. Is that fair?
James: Yeah. I think that's definitely true. But it also transitions to habits that we want to build, right? Because if we want to create the space for us to be able to stick to a new habit, then we need to understand what's driving our current behavior so that we can transition or readjust or rebuild that, so that we can make the space to build something new.
I'll give you an example. Pretty much every process in the living system has some form of equilibrium or homeostasis. Like your blood pressure for example, if your blood pressure dips a little bit too low, then your heart rate might speed up or your veins and arteries can constrict and expand as needed. Your kidneys can flush out more urine if you need to lower your blood pressure. So there are all these different feedback loops that interact with each other to try to maintain this equilibrium or homeostasis that's in a healthy range. And your body has this for all kinds of things. Blood pressure, temperature, calcium levels, glucose levels. But daily life is also like that.
We have all sorts of things that impact the pace, the rhythm at which we stick to our daily habits. So we all settle into our own version of equilibrium. And the forces that are currently in your life, all these things we've been talking about like the people that surround you and the physical environment, those are the feedback loops that create that equilibrium. Those are the things that have established homeostasis in your life.
So whatever your current level is at, whether it's high or low or it's somewhere in the middle, for any given behavior, the stimuli that are in your life right now are what have established that level of performance. If you want to improve that level of performance, you have to understand what those stimuli are, because if you try to fight against them, what you end up finding is that the harder you fight, the more you get pulled back toward that balance point. You need to figure out how to adjust them to slowly nudge your equilibrium up so that you can advance to the next level, rather than trying to fight all the stimuli that have established your routine, stable life.
Josh: If we put it into a practical example, how does somebody use that? What's a good example of forming a new habit?
James: Sure, well, the best examples are the easiest ones to understand. For example, strength training and working out and exercise. There's this dose and response graph, where if you don't stimulate your muscle at all, let's say you're doing a barbell curl, if you have nothing in your hands, then it's not enough load to stimulate muscle growth. If you try to lift 1,000 pounds, then it's too much, and you either get injured or the bar doesn't move. But if you can find some happy medium in between, then it's just enough stimulus to promote growth and not so much that you can't recover.
And that's the same idea with any new habit that we're trying to build. If you try to build a meditation habit and you say, all right, I'm going to meditate 45 minutes each day. And you start from scratch, it's so far outside your equilibrium right now that it's really hard to maintain that. You end up dejected or burned out or injured or ill or whatever it happens to be, depending on the behavior. Same with writing. That's why you'll hear people talking about doing morning pages, where they write 2 or 3 pages each morning or writing 500 words a day. These writing habits tend to stick better because they are manageable. It's a large enough stimulus to make a meaningful difference and a small enough stimulus to be maintained over the long run.
Josh: Is breaking habits an entirely different conversation? Or do you look at your default settings that you've got these feedback loops and you try to find something to insert or substitute in there?
James: It's not an entirely different process because your brain learns repeated patterns. And it doesn't know if the pattern is good or bad. It just knows that I have been doing this time and time again and so I should automate this and repeat it as much as possible. When a behavior starts, it's very effortful, for example, imagine if you are 3 years old, or however old you were when you learned how to tie your shoes. The very first time you had to learn to do that, you had to think very carefully about each thing, right? But now, you've tied your shoes so many times that you can have full conversation while doing it. You don't have to think about that, it's mindless.
What we see is that at the beginning of a behavior, your brain strains, it's very effortful. And then the more that you repeat it, the brain transitions the behavior to being automatic. This is true for good and bad habits. What ends up happening is pretty interesting, researchers have found that once a behavior has been made automatic, and this is true for bad habits as well, that pattern is built. That road has been laid in your brain, and you don't really forget it. Pretty much any behavior that's been automated is like riding a bike. You'll remember how to do it if the circumstance comes up again.
When it comes to breaking bad habits, what we're basically saying is that, if you're in a situation where that bad habit habit would be triggered, where the thing that prompts that behavior is apparent, it's very likely that you would follow that loop because that neural pathway has been built in your brain. So the best way to break bad habits is to avoid the trigger entirely. And that is maybe a slightly nuanced or different way of looking at it than building good habits, but they're the same basic fundamentals. Because the behavior's already been built, you're looking at prevention because the behavior's in the automatic stage rather than building a new habit, where the behavior's still at that effortful stage where you’ve got to think about each step of tying your shoes. Then you're focused much more on repetition so that the behavior can transition to automatic rather than trying to just avoid the trigger or stimulus that causes it.
Josh: Let’s talk a little more about your writing. You've talked through your journey into writing more often, writing essentially full time as I understand it, right? Do you still find yourself writing about topics that you don't feel like you know very much about that you are starting from scratch or close to scratch? Or do you feel like you've pretty much landscaped most of what you're spending your time on now and other work?
James: It's a good question. I think there are a couple of interesting things that come out of this. So the first is, whenever you start writing about something - I know I felt this way - inferiority complex is very common, right? Who am I to write about this? I'm not an expert. A friend of mine said, you become an expert by writing about it each week. That was a really interesting way for me to look at it, where in the beginning I really felt like I wasn't qualified to write about these ideas. But now, since I've written about habits and performance every week for 4 years, I am an expert because I did the work. I think that's an important thing to remember in the beginning.
But to answer your question, I certainly don't feel like I have it totally mapped out. It's the same with any topic, right? The deeper you get into it, the more you realize there is to learn. But I also intentionally try to look at things that I haven't written about a ton, because ideas are magical for me in the beginning. When I'm first learning about it, it has this quality of magic and excitement and interestingness. I want to naturally share the feeling of discovery that I have when I come across a new idea or a new story or a new way of looking at an old problem, and that's one of the things that prompts me to write. I have spent the last couple of years writing a lot about habits, but I'll probably transition over the next year or two to start writing more about other topics, whether it's happiness or health or creativity and innovation. All of these things fall under the purview of human behavior. But by looking at these ideas from a different angle or through a new lens, it kind of sparks that magic up in me again. And I get to share the excitement of discovering the world in a new way.
Josh: As you've been through this process over the last several years, where have you failed? Where have you thought something was going to work amazingly and it just didn't?
James: Well, there's been far too many failures to remember them all. I would say, probably the biggest thing as a writer is that I probably fail by not having enough guts or writing about things that are hard for me to write about. Writing about my failures, writing about my struggles, topics that were personally sensitive to me. I've probably done that four or five times over the year. I'm usually good for one a year. And every time I do it, it goes over really well, because people want to know that other people are like them, that they have struggles and challenges too, that nobody is perfect, that we all are dealing with this messy, complicated world and life that we're living.
I would say that writers that do a good job of wearing their heart on their sleeve are probably much better at that than I am. Hemmingway has that famous quote where he says, writing is easy, just sit down at the typewriter and bleed. Can you showcase more raw emotion than you do? That's probably one failure on the writing front.
From a business standpoint, many writers want to write their books and not worry about the business side of things. I mentioned at the beginning of this conversation that I view myself more as an entrepreneur. If I want to be able to maintain the integrity to write about whatever I want, whatever I find most useful, I have to earn that right. I have to figure out how to build a team and a business that allows me to have the freedom to do that. So that's a great philosophy to have.
But in practice, I end up having superhero syndrome, where I try to do it all myself. I probably waited far too long to hire full-time employees and grow the business. Last year, I hired my first full-time employee after having 6 or 7 freelancers that were stepping on various projects. That was a huge, huge benefit. She - Lindsay's her name - she's been absolutely fantastic. And we have grown as a result. It's no coincidence that this month we set a record for traffic and set a record for monthly email subscribers. It unleashed the ability for the business to grow more and for me to spend more time on what I think moves the needle best and is most important.
I have this big limiting belief about doing it. I think it's probably something that gets to the core of this question, which is, what are your failures? Well, at any point along the curve, if you view your career as a trajectory, there's always the next point or the next hurdle on the curve. You never get to escape that. You never get to escape the failures that are associated with your growth. There's always some limiting belief in front of you that is the bottleneck for the next thing that you need to do. I find myself continuing to run up against this as time goes on. Different problems, but they're always there.
Josh: It's a good point. And something I think about as a lawyer, right? Especially in this profession, it's one of these where for a lot of us, you're on a straight track for a long time. And the next move is often really well-defined. You go through the natural progression. You go to law school. You go to a big firm. Maybe you try to make partner at a big firm, maybe you go in house or whatever. But it is a pretty clear directional path. And as you think about transforming what you do or how you work, whether it's getting into anything entrepreneurial or frankly anything that doesn't involve being within the strict box of being a lawyer, I find that I and many people that are like minded in this profession to run up against that limit, that threshold, where you have to push yourself over and get through. It is an interesting idea.
James: Yeah, imagine you're in a raft in a river. And good weather is going to school and getting good grades, you're going to law school, you're making partner in a firm. The river has boundaries. It has these banks. And they say, all right your job is to row down the river as fast as possible. Avoid obstacles along the way, but this is the direction you're moving in.
Whereas entrepreneurship and creative pursuits are more like being in a raft in the middle of the ocean. You can go in whatever direction you want. But if you're not careful, you end up just rowing around in circles all day because you don't know what that true north is. The almost limitless freedom to choose where to spend your time and energy, what projects to work on, can sometimes be paralyzing, because you don't allow yourself to set a clear direction and stick to it, whereas that would be defined for you in a different role.
Josh: Yeah, that makes a lot of sense. And it's interesting you talk about what the true north is and defining these things as creative projects, but, at least in hearing you describe what you're doing, at the core, there is still a business here. And it's creative but it's creative with a true entrepreneurial thread. That distinguishes it, I think, from some other types of situations where you're creating for creation's sake, versus creating with the purpose of earning a living.
James: I want to get paid to learn. But the way to get paid to learn is to share the knowledge and create something useful with that. I guess that's the requirement, that I don't sit around and read and learn and experiment with things all day and try to do fun stuff for myself, whether that's travel or whatever. All those are great learning experiences but how can I transition and translate that into something useful for the reader.
Josh: Can we talk about the business for a minute or two? We've talked about it in broader terms. But just to kind of drill down a little bit. You have an email list, right? You have that habits seminar class. I don't need to know the specifics, but generally when we talk about revenue streams, we talk about what is the business, what do you define as the business?
James: There are four primary revenue streams and two or really one primary lead generation stream. We can start at the top. Right now, just round numbers, say, a million visitors a month to the website. It's around 3% conversion to the email list. If we can get people to join month after month, that's our lead generation stream. The email list is about 400,000 people right and continues hopefully to grow quickly, fingers crossed. Once we have that audience, we can choose how we want to sell to them.
I decided to simplify my business. I want to have a variety of revenue streams, but I don't need 17 different revenue streams. I want a couple that could each turn into a really solid revenue stream itself. So the first one is books. My first book deal is with Penguin Random House. You can get a large advance if you have a sizeable audience. You can also hopefully sell books into perpetuity and make money on each copy. Then there are courses. You mentioned the habits seminar. We actually just reshot a new version of that. It's going to be called the habits master class. And that's going to try to be the world's most comprehensive course on how to build habits and improve performance.
Speaking engagements are the third. I am not really interested in being a professional speaker and being on the road like 50 events a year or something like that. I tend to only accept one a month; that's kind of my sweet spot. I was on the road 18 days last year for paid speaking events and that's about where I would like to keep it. But if you have a best selling book, then your rates can get fairly high and that can be pretty lucrative as well. And then the fourth one is kind of a bonus and that's affiliate stuff. I don't do affiliate things for other courses or things like that, but if I mention a book in an article I'll link to it on Amazon or something along those lines.
Josh: You read all day to create great stuff. Is there something you read everyday, that you think other people should be paying attention to?
James: I don't have any publications that I read everyday or any little quotes or things that I return to. I think the thing that could be useful along that regard is treating reading as a practice and not something to practice. For example, we often talk about practice as a verb and not practice as a noun. What are the practices in your life? And for me reading 20 pages a day is something that I try to make a practice. I would say that thinking about reading as a process that you commit to or a practice that you perform is probably better than thinking, I need to be reading more.
The Truth Will Out.
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“I will represent pro bono anyone #Trump sues for exercising their free speech rights. Many other lawyers have offered to join me.” - @BoutrousTed
Weeks before the 2016 Presidential election, Gibson Dunn’s co-head of litigation (and fellow USD Law grad) Ted Boutrous took this unusually public Twitter stance against a major party nominee. We knew then that this was no ordinary nominee, and we saw unusually public stances coming from many places. Even so, a well-respected Big Law leader making this declaration drew attention from lawyers and non-lawyers alike all over the country. I reached out to Ted in November to find time to talk. I wanted the story behind this tweet and I wanted to learn what happened behind the scenes in the weeks that followed.
But since November, more has happened than most of us could have imagined. We’ve seen rapid changes in what free speech means and how it’s treated – from the government’s outright hostility toward journalism, to upending established norms in how the government and the press co-exist, to the administration’s communication with the public, to putting into question the basic assumption that what the President says is true.
Ted is deeply involved with each of these issues. In this interview, he explains how he got where he is and what he’s thinking about now. We talk about Twitter and the First Amendment. And we explore what you can do now if you care about journalism.
Find more from Ted on Twitter at @BoutrousTed.
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Josh: We'll talk in a few minutes about your now famous tweet where you said you would defend anyone sued by Trump for exercising their free speech rights. I want to talk a little bit about you and your practice first. I learned of you through your First Amendment work. But you actually do an awful lot more than that. Could you lay the groundwork about what you do and who you work with?
Ted: I went to law school at the University of San Diego, and wanted to practice appellate constitutional law, I really wanted to be at the intersection of government, the Constitution, but be in private practice.
When I joined Gibson Dunn, my law firm, we had just started an appellate group in Washington DC. Ted Olson, who went on to become a Solicitor-General had come back from the Justice Department back in the mid ‘80s and started an appellate constitutional law group, and I thought that sounded like exactly what I wanted to do. I was one of our first associates in that group. This was in 1987. And that practice really blossomed and in some ways exploded.
It is much broader than even appellate litigation. It allowed me to get involved in thorny, complicated, interesting, high profile issues that cut across a whole range of topics, sometimes for corporate clients, sometimes for individuals.
I was a staunch Democrat coming out of law school and one of my first projects was to work with Ted Olson representing President Reagan during the Iran Contra investigation. So it was very easy to make the switch when you’re representing a client. But it’s been a great, great practice for me, and a great opportunity. As part of that I began working on First Amendment matters.
Josh: When you say you wanted to practice appellate constitutional law, isn't that every law student?
Ted: It is. I got lucky. I took a somewhat unconventional path when I dropped out of college twice. I didn’t quite know what I wanted to do. I started out in North Dakota where I grew up, and I realized it’s too cold there. I’m getting out. So I left college there, had the bright idea of going to Arizona, which was fantastic. When I was there, I took a philosophy of law class and found that's what I wanted to do. My dad was a lawyer, so I’d always thought about it.
I didn’t know the limitations that might be out there on exactly the issue you mentioned. A lot of people want to do that kind of work. I didn’t want to clerk because I had taken a couple of extra years to get through law school. And I thought, this is what I want to do, this is a great law firm, I’m going to go do it. It’s a bit of a testament to, don’t think that there are limits on what you can do.
I think it’s one of the things that’s great about our country, that where you come from and how you get there doesn’t limit your ultimate destination. So I got lucky. I found a firm I loved immediately. Ted Olson and I bonded very quickly and worked together for years, even though he is a conservative Republican and I’m a liberal Democrat, but somewhat non-partisan. It was sort of a series of lucky breaks and it’s been a great place for me and I love what I do. That makes a big difference too.
Josh: What was it about a philosophy of law class that did it for you?
Ted: It was a class that focused on Ronald Dworkin, probably one of the greatest legal philosophers of all time, and his method of legal philosophy and thought. The high level of analysis and how legal thought and legal issues intersected with basically every aspect of society. So public safety, product development, the Constitution, the separation of powers, technology, business.
Everything intersects with the law, and it really gelled for me, that being a lawyer would allow me to think about the kind of things and do the kind of things that I really like to do. I’ve always been very interested in politics and I was a political science major. Being able to have both a job that pays money but also lets you participate in these broader issues in society, that’s what hooked me.
Josh: You mentioned you dropped out of college twice. Then you ended up graduating at the top of your class at USD. What clicked? Did something change?
Ted: One, I realized that, I knew what I wanted to do when I was at Arizona State. I wanted to go to law school. I decided at the last minute before law school admissions would kick in. Then I ended up going to a law school I absolutely loved. It was like heaven. I think you know it well.
Josh: I do. Our stories are actually very similar. I took the LSAT on the last day of late registration, or signed up for it on the last day of late registration and said, I think this is what I want to do. And then ended up going to USD, from Colorado State University. Very interesting parallels here, actually.
Ted: That sounds very familiar. I ended up at this great place, where it’s a beautiful place to be, and I plunged in to law school. It was like something clicked. I was on a new path and I knew what I wanted to do. I also met my wife on the first day of law school, so that helped. That gave another mission to my life and career.
I think you go through phases, and as part of the journey, you learn a lot and you end up finding out what you really like to do. If it turns out that it’s a profession that you can survive on, it is a nice combination.
Josh: Sure. So then you're working with Ted Olson, kind of an amazing place to fall into as that practice is growing. You're now one the preeminent people who does what you do in the country. Were there a couple of milestones as you were progressing in your career at Gibson that you felt like, you'd reached either a new level or that you'd really done something that you were proud of?
Ted: Yeah, you know, it’s interesting because my law firm is a great place because we create a lot of freedom for even the most junior associates when they walk in the door. The minute I walked in the firm, I felt like I was an independent operator but I had this great support network and great mentors and all the things you’d look for. A lot of independence.
One of the first things that made me think I was breaking out a bit was, I wrote an op-ed piece for the Wall Street Journal on the independent counsel statute, which at the time, this was the early ‘90s, was very controversial. It was published, and it was a big moment for me. I’ve since probably written 25 of them for the Wall Street Journal. But the fact that I had partners who wanted to let me be out in front, I think is a lesson in giving your more junior colleagues responsibility and opportunity and the ability to try. When you’re just starting out, it makes a huge difference.
My practice was starting to thrive independently once I became a partner in the mid ‘90s. Then the guy who’s now the chairman of our firm said, you really should think about coming to Los Angeles. You could build a west coast version of the appellate group and I thought that sounded great. My wife Helen and I had always thought about coming back to California. We fell in love with Washington DC life but we jumped at the chance to move back to California.
When I came out to California, it was like a whole new world because you've got a lot of litigation, number one, but with the technology boom, you had vibrant commercial activity. That opened up a whole new world for me. Another launching pad for me was, you meet good clients. When Walmart had this massive class action certified against it, I had never represented Walmart. I was one of the people they talked to. They hired me back in 2004 to help them on the appeal, and I ultimately became lead counsel on the appeal. That went all the way to the Supreme Court and we were able to get that class certification overturned. And it was a landmark decision. So a series of those sorts of things.
This goes to the mentors and lucky breaks. Bob Sack, who ultimately became a judge on the Second Circuit there in New York was one of our partners in the New York office and a legend in the First Amendment area. He asked me to help him on a First Amendment case that was actually a Senate investigation regarding who leaked the Anita Hill allegations about Clarence Thomas to the media and to our client, Tim Phelps, who was at Newsday. That was my first big First Amendment battle. We asked the Senate to recognize a reporter’s privilege basically. And they did that. It was a wild experience. That added this First Amendment journalism piece to my practice that I think created the world that I’m now in. Those are some of the milestones for me that got me where I am.
Josh: Why do you think you were asked to help on that First Amendment case?
Ted: It’s interesting. It was focused in Washington, which is where I was at the time. I was one of the junior to mid level associates. Ted Olson was going to get involved as well. We're very good at collaborating across practice groups and offices, so Bob called Ted and Ted suggested I help, and Bob and I became very close colleagues and worked together over and over again on really significant, interesting, major First Amendment battles for the Wall Street Journal, the New York Times, all the networks. When you look back, I think I had a series of lucky breaks, being at the right place at the right time, and also being at a place where you have collaboration and everyone looking around to find who can play a role that will make the team the strongest. Those things really benefitted me.
Josh: So you're talking here your first case in defending journalism. And as you mentioned, that's become a pretty significant part of your practice. I saw an interview that you gave a few years ago where you actually said if you weren't a lawyer you would have been a journalist. Do you still believe that and if so, why?
Ted: I do. I’m a big consumer of news and journalism. It’s one of the reasons I wanted to go to Washington out of law school. It’s one of the things that I really thrive on. I have a lot of respect for what journalists do. That’s why it drives me crazy when President Trump says these false things about journalism and about journalists, because I think it’s a crucial part of our democracy and our society.
I love journalism, and representing journalists, I got to see up close and personal what they do, what’s important to what they do. And I like to write, and sometimes people forget that as lawyers, you do a lot of writing. A journalist once said to me, lawyers are probably the highest paid writers in the world. There may be some screenwriters and the like and novelists that outpace us. But it’s a luxury as a lawyer to be able to write and I like to write.
Journalists, one way or another, whatever type of journalism they practice, they have to write and synthesize information and determine what’s important, and it has a lot in common with what lawyers do. Ask, interrogate people, look for evidence, put it all together, make the case if you’re an investigative journalist. There are a lot of things in common, and working closely with news organizations and journalists made me think even more highly of what they do and that that would be something that I’d want to do.
Josh: What do you make of sort of the current state of journalism?
Ted: I think that it’s a really exciting time for journalism and that probably the best journalists in the world exist right now, that have ever been on the face of the earth.
Josh: Anyone you want to mention?
Ted: I don’t want to single anyone out because I’d be leaving someone out. But if you look at the reporting that has been done during this campaign, if you look at the story that David Sanger did in the New York Times on North Korea a couple of weeks ago, the New Yorker piece on Russia that was a couple of weeks ago. It is such strong journalism. It’s powerful work.
As a lawyer, I would see journalists from practicing. When I'm not representing a journalist, I would see journalists from the other side covering me. I got to know Linda Deutsch who is now retired from the Associated Press. Watching her in action, she’s probably the greatest trial reporter. She covered the Manson trial, the OJ Simpson trial, that’s where I got to know her when I was representing journalists there. To see how she could observe and then write it down with accuracy and making it interesting and exciting, and doing it instantaneously, right there, here’s what happened, and to capture what people said, I think we’ve got journalists that are doing tremendous work.
There are some that are not, and that’s one of the things that we confront here, the blending together of organizations that on their face purport to be journalistic enterprises who are not following the conventions of journalism. It can get a little bit complicated. But if you really look at the organizations, and it’s not just what we’ll call traditional media; you’ve got Buzzfeed and others just doing tremendous work, like Politico. The list goes on and on. So I think it’s really a great time for journalism and the fact that we are in this atmosphere where we have, everyday, about a year’s worth of news with President Trump and his administration, I think it’s going to keep going.
Josh: I think it's pretty amazing to see what's been going on. You mentioned the blending of organizations that purport to be journalistic and that aren't. And we've seen over the last several months lots of different story lines around the difficulty that exists and may continue to exist, and understanding what's true, right? How do you see that from where you sit on the inside of some of these conversations?
Ted: It is something I’ve thought about a lot because we have a president who says things that everybody knows is false and are false. The tweet about President Obama supposedly wiring Trump Tower. Everybody knows that’s false. And yet he claims it’s true. His apparatus claims it’s true. He has a media platform of his own. He said last night I think with Tucker Carlson that, he thinks without Twitter he might not have gotten elected and it really is his megaphone. So you’ve got that piece of it.
Then you have the fact that he relied on this blend of information for coming up with his tweet that included a story in Breitbart which falls in my view into the category of organizations that act like they’re news organizations but they really aren’t. They are information producers. I’m not saying they shouldn’t do what they do, but it’s not what I think of as journalism. And they’re relying on a Mark Levine radio diatribe and all that is sort of mixed together and they’re spewing out information that’s not true and they’re jumping to conclusions.
I think that’s one of the dangers that we face right now and there’s been a lot of writing and discussion about how in authoritarian regimes and totalitarian regimes, one of the things that is used as a mechanism to exert power over the people is to confuse the facts and to say up is down and down is up. That’s why journalism is so important right now, that true reporting, sticking with the facts, digging for the facts, don’t stop focusing on a topic just because there’s another topic that’s come along, I think is so important. Because that’s what gets lost when we talk about the First Amendment: one of the main purposes of the First Amendment is to make sure that citizens have the information they need to make sensible decisions about how to govern themselves. If you use that premise, that is a crucial mechanism that we need the journalist community to help us achieve. I think that getting to the truth has never been more important than it is right now and journalism is essential to that. And lawyers as well. I always come back to the relationship between what lawyers do and what journalists do. They are two of very few professions that are embedded in some way into our constitutional structure and are part of what we think of as the fabric of our democratic system.
Josh: So you mentioned the fabric of our democratic system and you also mentioned Twitter.
Ted: Ha. Yes.
Josh: Let's talk about Twitter in the context of the discourse. How did you phrase it? People who make intelligent decisions around how they are governed. You've been a Twitter power user for a long time, long before this election cycle. How does something like this fit into the broader conversation of the exchange of ideas that we think about broadly with the First Amendment?
Ted: I think of Twitter in several ways. First, I really started using Twitter as part of an information delivery system and for some of my clients, where they were involved in big cases and the folks on the other side were using Twitter and all sorts of other mechanisms to get their message out. I’m a big believer where it is appropriate to engage with journalists and to speak to the public about a case where there are public policy issues in particular, but especially if your opponent is coming at you and using Twitter and Facebook and other platforms to make their case and to try to win and defeat you both publicly and in the case. That’s how I started on Twitter.
Then my eyes were opened in terms of the information delivery system that it is and as you know, journalists in particular thrive on Twitter, use it a lot and in terms of getting basic news about what’s happening in the world, you can create your own universe, but if you just focus on major journalists and news organizations of all different types, it’s heaven in terms of getting information. So that’s two prongs.
Then you have the falsity and the downside of unlimited free speech. You have people saying awful things on Twitter, false things on Twitter. You have the President of the United States and then the presidential candidate before that, same guy, Donald Trump, saying false things, threatening people, going after individual citizens, accusing his predecessor of what would be the crime of the century. Those are some of the downsides. But another premise of the First Amendment is, the truth will out. That if you keep battling back and forth for information, the truth will survive. And you can fight falsity with truth. I don’t think that that’s changed. It’s just more of a free for all.
We need to keep all those features in mind when we think about Twitter. On the tweet heard around the world as you called it, at least from a lawyer’s perspective, then-candidate Trump at Gettysburg had used that platform to denounce the many women who had made accusations of sexual misconduct against him. Then he declared that he was going to sue them all once the election was over. That struck me as such an outrageous thing for a candidate to do, to threaten, to intimidate citizens from speaking out during a presidential election, it never happened before.
I popped down to Twitter and said I'd represent anybody pro bono, who Trump sued for exercising their First Amendment rights and the response was amazing. I had legendary law professors like Laurence Tribe saying I’ll help, and people all over the country, lawyers saying, we'll help if you need us. It was just amazing. And that could never have happened without a platform like Twitter. We organized a little team and some of us started working together on various matters now, and so it actually had this amazing effect. Platforms like that have many amazing, positive features.
Josh: Let's actually talk a little bit about what's going through your mind when you decided to tweet that. You were reading an article or you saw a clip and you pull out your iPhone and you banged that out real fast and throw it out to the world and then 50,000 people or something respond to you, or what happens there?
Ted: It was interesting. I think that was October 22nd, a couple of weeks earlier, when President or candidate Trump threatened to sue the New York Times, Melania Trump had threatened to sue People Magazine, they were saying they were going to sue New York Times for publishing that state tax return information and for libel. I thought, this is crazy. And the Palm Beach Post had come out with its first piece.
I think someone prompted me and said, these smaller news organizations people, they’re not going to be able to afford defenses. So I said, hey, I'd represent them pro bono. That got a very strong response on Twitter, especially because we lawyers don’t get the Donald Trump or George Takai treatment from Twitter. When I was actually watching Trump’s speech live at Gettysburg, I thought, this is crazy. I talked to my wife and we were just marveling at it. Then someone retweeted my original tweet and said, gee, this might be a good time for people to know that your vow still stands. I then conferred with my wife Helen before pushing the button and said, I repeat, I will represent anybody who is sued or threatened by Trump for exercising their First Amendment rights, and sent it off and it just exploded.
I went to sleep, it was a stream of activity, and then the things that happened overnight were, in terms of retweets, replies, it was wild to see. I’ve represented people who were part of that group that he was threatening that day and related to those issues. I felt that had an effect. It also helped create this network of lawyers who are standing by on First Amendment issues, immigration issues, constitutional issues that are no doubt are going to keep arising. So it was quite an interesting experience.
Josh: I think it's interesting and it's wise that you asked your wife. I notice you didn't say you actually asked anyone at the firm. But I guess maybe you don't need to.
Ted: Well, I’m now senior enough, I'm on a management committee. I had a pretty wide leeway. But I did check in and make sure folks knew about it. We have a firm where being politically active and having a pro bono practice is encouraged; this was a little more unusual. So I did go back and explain and give everybody a heads up. But I think First Amendment issues are a truly non-partisan issue. The First Amendment is neutral, and that’s why I thought, in a campaign, come on, you can’t use the power of your position to try to intimidate citizens, voters from speaking and participating in a political battle. So I felt I was on very safe ground. But as a lawyer you've put your finger on some of the risks that we as lawyers have on Twitter too. Especially with client matters, you do need to keep all those issues in mind.
Josh: You mentioned a couple of other things there. Specifically, that this group has been building a coalition, I think some of it's been pretty public, Laurence Tribe you mentioned, has been very vocal, and some others. Is there some collective activity going on behind the scenes where you’re all are talking to each other?
Ted: Well, it’s been I think very healthy for the legal profession just like I think Donald Trump has been healthy for journalism in a strange way because lawyers at big law firms and professors and lawyers at small law firms, plaintiffs lawyers, defense lawyers who agree on legal principles and policy principles are communicating about these issues around the country.
For example on the immigration side, I’m working with Professor Tribe and Professor Chemerinsky from California here on the first DACA case, the immigration case that we’re handling. That grew out of communications we had back in the campaign. And you've seen law firms in the immigration band, battle, we filed the brief in the Darweesh case there in the Second Circuit. There were terrific briefs filed in Hawaii and in the other cases. You've seen the legal profession step up in a big way here.
Different people have different views on policies. I agree with a lot of Republican policies, particularly business-oriented policies, but this president has been very clear that he's pushing the envelope on constitutional issues, on legal questions. The travel ban, they're peddling to the middle. On the immigration front, as you know, for businesses, the tech industry in particular, but many other businesses think that we are the leaders from an economic standpoint because we welcome people from other countries. It's who we are as a country. It's a galvanizing thing from a legal perspective and we're seeing it.
I am spending so much more time talking to my colleagues at different firms, at public interest groups, at law schools. It's very exciting and energizing. I feel good about the country because of the way people are responding. We can all disagree with policies, we can disagree with the approach that the administration takes, or agree with it, but there's a place for lawyers that I think we haven't seen in the democratic process at this level right now that is really remarkable.
Josh: Does it feel different to you be a lawyer now than three, four, five months ago?
Ted: It does. You've put your finger on it. I think it took my own consciousness to another level, where my own practice as it was before, it's always had different elements and my cases ranged widely, go from defending against the class action, arguing an appeal, arguing a case on a big punitive damage order or something like that, and then First Amendment issues and the like.
But it's a legal awakening and another level of consciousness of how important the rule of law is, how important lawyers taking responsibility for protecting the rule of law is in our system. I do feel differently and it's a positive thing, although there are ups and downs when one looks at what is happening in the world. I think your question is a good one because the answer is absolutely yes, I feel differently as a lawyer, and feel I and everyone else has even more responsibility to play a role in ensuring that our system functions properly.
Josh: Two more questions. One, everyone should feel responsible to make sure our system's functioning properly. What can people actually do right now? Lawyers and non-lawyers, maybe let's split it up. What would you tell people if they are concerned about, even if we just leave it at First Amendment issues and things that you said maybe shouldn't even be partisan, the functioning of the democracy. What are things that you feel people should be doing or could be doing right now?
Ted: I think there are several things. One, participating in the process in an orderly way. The protests that you've seen, the women's march, other protests, that's democracy. I think getting involved with issues, it sounds a bit trite, but it's absolutely true. It makes a huge difference. I think on both sides of the aisle, standing up for principle. You look at the Republicans, you can tell they're uncomfortable with some of the things that President Trump is doing and saying. And some of them are pushing back a bit. But be they Democrat or Republican, stick to principles, stick to what you believe in and protect and get involved in things where you can protect those values.
On the First Amendment front, supporting the Reporter's Committee for Freedom of the Press, organizations like that. I've been on the board of the International Women's Media Foundation for many years, that seeks to protect women journalists around the world. Usually we were focusing more on foreign countries, because they didn't have the First Amendment protections. But now you see that we need protection of journalists in the United States in a way that we didn't before. I think you've seen a renaissance for the ACLU, Public Council, other organizations like that, where people are saying, wow, those groups really can make a difference. I think supporting those groups, putting pressure on your elected representatives, these town hall meetings. All of a sudden people realize, wait, I could go to a town hall meeting even if the person in office is someone I didn't vote for. I get to go talk to that person. It doesn't have to be angry. It can be a dialogue. So I see there's an awakening around the country and on both sides, across the political spectrum. That's a real positive thing. We have President Trump to thank for that, and we'll see how it all plays out.
Josh: You said that the First Amendment isn't partisan. You said there are some folks that are uncomfortable with some of the things that are being said and the way that information's being conveyed right now from the administration. Are you concerned that the First Amendment may become partisan or that people will not defend it in the way that maybe you believe it should be defended, in this environment?
Ted: I am concerned that the approach that President Trump and his team is taking is meant to devalue and undermine and damage the First Amendment and free and open dialogue in the country. To say that journalism and journalists are the enemy of the people, for example, that is wrong. That is flatly contrary to our constitutional principles.
I'm not concerned that the journalists and others who fight for First Amendment freedom and who engage in journalistic activity and speech in a way that's meant to participate in the democratic process are going to hold back. That's one of the things I feel very strongly about.
You see in other countries that, Russia for example, which appears to be a template in some ways for our current administration, killing journalists, squelching journalism, is a means towards more power. I don't think that's going to work in the United States. I don't mean to suggest that the killing part was even contemplated. But I do think that this delegitimization of journalism, this denigration of the whole process, this ridiculous fake news label that the president and others are using. That's meant to change how we look at the First Amendment. The good news is, I don't think it's going to work and I think journalists are being inspired to do an even better job, that is going to be essential over the next few years.
Market Like a Marine.
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“Traditional marketing is BS.” Ok, I wanted to hear what this guy had to say. And when I met Todd Caccamo, I was surprised to learn how his experience in the Marines aligns with the scrappiness you expect more from startups.
In this interview, you’ll find one recurring theme: start with something unconventional – whether it’s attacking the competition from a crazy starting point to doing something “in the way that is wrong”, Todd explains why conventional marketing wisdom doesn’t work anymore. And as he reminds me, the enemy always gets a vote.
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Todd starts off by telling us a bit about his background.
Todd: I'm the director of services marketing for GE Aviation in the TrueChoice part of our business. Prior to that, I'd had a number of roles within GE Aviation as well as with GE Plastics and some other industrial firms. Before that, I was a graduate of the University of Michigan. Go Blue. And of course I did a couple of tours in the United States Marine Corps. Probably not your typical marketing background.
Josh: How does being a Marine help you in marketing?
Todd: I think it gives you a unique perspective and also a bias for action. In other words, if you're making a battle plan, you need to focus on the objective as well as the enemy. Well, here in marketing, it's sort of the same thing. With real marketing, you have to focus and have the customer at the center of what you're trying to do. But I think the most important thing is a bias for action, and knowing that when you lay out a plan, that that plan that you end up actually executing or completing the objective with may not be the original plan you started out with, because as we like to say, the enemy gets a vote.
Josh: One of the things that you’ve said is that most traditional marketing is BS. Can you expand on that idea?
Todd: Let's start with the 4 Ps. That's the first thing everyone is taught when they were going through marketing and MBAs. There's price, product, promotion and place. Well, I would argue that even that's changed. You could come up with a whole new definition for those four Ps.
First off, let's talk about product. I would probably argue 80% of the value is outside of the product space in terms of: how one goes to market, the distribution channels, or in profit models, or in customer experiences. Just look at the big names of our time that have really revolutionized those things, whether it's Amazon or Google or Virgin or Apple. Apple's thought of as a product innovator. That product to me is just the human interface to the other aspects that they've influenced, such as how they went to market, the distribution channels and the profit models they have. That's the hidden genius.
So much in marketing has focused just on that first P, where in my mind, that first P could be renamed from product to pain. What pain is the customer feeling? Taking that consultive selling approach and finding a solution to what the issue is. The issue may not be a physical product. The issue may be a service. The issue may be a distribution. It's really not even a product anymore. There's so much more out there today that is not product focused.
Then if you were to look at the second P, let's call it promotion. It's probably more like proving it. Educating the customer as to why your solution has the value that you're saying it has. And if you look at the third P, place, it's not even place anymore. I'll call it a portal, where people want access to data. We talked about the IoT and analytics. Having access to data, having access to these services, even having access to the product in terms of how we have skinnied down the supply chains and done a number of things to speed product to market. Look at Amazon and Walmart and how they've done things.
Then of course we've talked about price. That's probably more like proving the value. Maybe instead of price you're talking about profit, because - and I'm going to borrow a quote from the big man here at GE, Mr Immelt, he would say find out how your customers make money and help them make more of it. Or you could also take that a little further and say, how do your customers lose money, and help them lose less. How can you maximize their savings? In other words maximize profit. That's either through more revenue, because they're offering greater value to their customers, or lower costs, because you're offering greater value to your customer. That's just a smattering of how I would say that modern day marketing could undergo a bit of a facelift.
Josh: Sure. So what do you say to somebody that already has a product, already has an offering, and I think you can make it a bit more difficult if you say it's already a physical product that's being made. So you can't just go and change some software features and test around. You've already got a thing. It's already baked. Where do you start? Walk me through how you'd rethink what you're doing with the product, what you do with the business.
Todd: Oh, there's about a billion things you can do. I mean that seriously. So you've got a physical product. Great. If you just want to sell your product versus someone else's product, and let's say the features essentially the same. Now it's a price war. The value is the same. They're going to make a decision on price. How are you going to differentiate? It could be your profit model. Maybe you're offering it as a lease. Maybe you're offering different financial terms.
And how about service? If you had a product that's great, but your service is horrible, well, that's a big red flag. My brother's a big fan of a certain car brand and one of the reasons he is, is because of the service that that brand, not just the dealership, but that brand offers its customers. He's like, I'll never go anywhere else because of that. All of those what I'll call non-product features may not appeal to everyone, but they're going to appeal to a pretty big chunk of the segment.
People think of segmentation in a very regimented way. Everyone's done it the same way for years, whether it's behavioral or classification or different types of buying patterns. Everyone's trying to come up with this insight as to what buying pattern makes this customer segment unique. It's really hard to mechanize things like segmentation. You almost have to do it in a special forces kind of way. You got to do it in the way that is wrong. You got to start in a way that's just really off the cuff. You are going to find trends. You're going to find commonalities. You're going to find threads that other people won't. And then you can go ahead and be at the market or be in the right segment and customize and be flexible. That's the big hint here, is being flexible, because that really is one of the key differentiators.
I'm a big hockey nut. If I'm not playing hockey, it's a bad day. Wayne Gretzky would say, hey, a good hockey player knows what to do with the puck when he gets there. A great hockey player knows where the puck is going to be. The old cliche is, the best way to predict the future is to create it. A lot of the segmentation, a lot of this stuff we're looking at, is based upon past behavioral patterns. Look at Apple. They created the future. They made these new markets. They really had vision as to what we needed. If you ask them what they need, you might not get a really good answer. But if you tell them what they need, and then they adopt it, well now you're off and running. That's where that testing comes into place, because I promise you, not everything that you think that's going to change the world will change the world. You're going to have flops. But if you don't have failures, you're not pushing the envelope. You've got to do some of these traditional exercises in a non-traditional way to get really meaningful insight as well as maybe get a glimpse as to what the future could bring.
Josh: Can we talk a little bit more about one of the things you just said? I wrote down special forces segmentation, and that you don't want to fight fair fights, you want to fight a fight you're going to win. I think in the start-up world, and big company world too, but especially in start-ups, you're sometimes competing against giants, right? Everybody else in your space is 10 or 100 or 1,000 times your size and you don't have traction and they do, or some variation of that. Can you walk through what you think special forces segmentation means and how you can tip the scales in your favor from the outset when you're designing and offering as a smaller company in a world populated by giants?
Todd: That's a good question, and it is one of the quandaries that many companies face. But it really does go down to some of those non-product innovations we talked about earlier. What is your profit model? That's something that you can certainly affect as a small company. Your network may or may not be a strength you have at that time. But your structure, how your company is structured for execution, the process enablement that you give to your customers as well as to your internal customers. And the channels that you pick to go through your customer engagement. Those are all things you can pick to really go ahead and tilt the scales in your favor.
If you think about it again from that special forces kind of mentality. You don't want to engage the enemy head on. You're going to lose, right? You want to go and fight a war of attrition. You want to become a force multiplier. You want to come from the angles that are least likely. I could tell you about both war time and actual peace time training missions that we pulled off, where we're thinking, what is the craziest, stupidest thing that we can possibly do? Attack from there. No one is going to think we're dumb enough to do it. And it worked. One of the weapons you have at your disposal is your size, and you're nimble and you’re flexible. You think about a big company trying to deploy some of those MVPs and it probably is more difficult because there is a brand risk. And the time it takes to go ahead and get something done is usually eons compared to a small start-up. A small start-up in my opinion could probably go ahead and do five MVPs in the time it takes me to do one.
You can go ahead and develop that product that much faster. Get that much more VOC. Really get something that's going to work. Then part of your distribution may be to partner with one of the giants through a licensing arrangement. So you're using the strengths that you have, which are nimbleness, which are proximity to the customer. And then you can leverage the strength of your big brother ally to go ahead and do what you need to do.
Sometimes you're in competition with the big guys, sometimes you're in partnership for lack of a better term. But long story made short, your nimbleness and your size as a weapon, it needs to be maximized.
Josh: One of the things you referenced to when you were talking about this was structuring for execution, I think is one of the phrases you use. As you're building a company, let's say you're on the small side and you're growing, how do you think about structuring for execution? What should leaders be trying to put in place as they're building a company?
Todd: I guess it depends upon what stage you're in. Let's assume that it's mid stage. You've got a number of employees. You've got some structure. You've got some assets. Number one, you've got to be decentralized. You have to let decisions be made at the periphery, at the tip of the spear. If as a Marine rifleman, I had to call back and ask, “mother, may I?” Well, we wouldn't be that effective. I'm going to put a plug in here for veterans working in corporate America, you were trusted literally with the lives of your own troops, and you were trusted in life and death situations many, many times, why would some VP not trust you with a business decision?
If not, then maybe the wrong leader's in charge. It has to be a decentralized organization that can go ahead and work around a central mission. If your tactical action supports that central mission or that central objective, take it. And that has to weigh against the question, is speed more important? Patton would always say, give me an 80% solution and execute it perfectly versus wait for the perfect plan and have poor execution. I firmly agree with that. Have something that's going to advance the ball, and if you can advance the ball let's say 80% or 90% in a direct course, it advances a heck of a lot faster than the person who is crawling along at the perfect direction. You're going to beat that person to the pie every time.
Josh: Yeah. One of the things that is a crucial dependency for what you just said is, you have to have clarity on what that central objective is. In an environment where stuff is changing rapidly, I think it's incumbent on leadership to make sure that people know what that objective is, so that then they're empowered to go and do what they need to do. That model breaks down where there is confusion or there is not clear information among the people who are actually out trying to make those decisions.
Todd: The one thing that I definitely want to leave with you and your readers and listeners is that when we're innovating, it's almost like how you and I met over a controversial statement. I encourage people to go out there and really advance disruptive ideas. If there really is value in it, the customer is going to show it to you, by you working with them, having them filling out your value chart, finding out what's really of value to them, that's important. The art of discovering, finding out what really works.
I used to walk in as a young sales or marketing guy and say, look, I'm going to save you 75 seconds on your cycle time. I'm a genius. Buy my stuff. And they would show me why it was no value to them. But if there's real value and you're working with a customer, find something that's different, find something that's controversial, find something that's big and go out there and keep pushing it. Eventually you're going to find the person who gets it. And that's going to be the person who helps you scale it within your own company or outside of your company or whatever. We're always going to push for incremental improvement, but get that big idea and just go with it. Push it hard. Eventually, if it's really true, someone's going to get it.
Josh: What if you're wrong?
Todd: On the big idea?
Josh: Yeah, what if you put yourself out there, you get the megaphone, you start shouting it from the rooftops and you're wrong, or you're afraid you're wrong. You're not validated quickly enough. What is that like?
Todd: That's the person I want on my team because if the person can be wrong, and put themselves out there like you said, that's the person who's going to advance the ball. If you don't fail every once in a while, you're not pushing the envelope, you're leaving a sick amount of profit on the table. You're leaving a sick amount of personal development for you and your team, undeveloped. You're not an A player then. I want that person on my team.
I remember I made a mistake early in my career at Ford Motor Company and this seemed like huge money at the time. I don’t even remember what the mistake was and it probably cost Ford maybe a 100 grand or something. In the grand scheme of things, that's peanuts. But to me it was like, oh my gosh, my whole world closing in on me. And I was ready to quit over it.
The boss said to me, “what are you doing? You just got a $100,000 education. If you make the same mistake twice, then I'll fire you. So get out of here. Go put to work what you just learned.” And that's a lesson that stuck with me. That's the person who's eventually going to get a big idea over the finish line, versus the person who is going to go into the corner and sulk and be a wimp and not want to push that envelope. I think those are the people that lead Marines, those are the people that lead companies and those are the people that lead in general.
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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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