Eran: I'm ready.

John: Yes. Eran is an Israeli born writer, journalist, and designer, who spent the last nine years in New York City. His first book, The Book of Hard Truths, is an illustrated guide to the most universally resistant aspects of life. Eran, take a minute and fill in the blanks from the intro and then give us a little glimpse into your personal life.

John: For the past ten years or so I've been pursuing two parallel courses. One is – in the startup business I was a product manager in designer of user experience in a couple of startup sin New York. And the other is more intellectual. I studied philosophy. I studied history. I have a degree in history. And I'm now doing a master’s degree in religious studies, so kind of asking the big questions of life. This book is actually kind of a culmination and integration of both of these tracks over the past ten years because it's definitely a very designed experience. It's not really a standard book. It’s more like an experience that you go through.

And that relies heavily on my design background and my user experience uses psychology background. And it deals with hard truths and the hard truths of life, which is definitely more into philosophy and even religious studies side.

John: So I love the fact that you're focusing on the visual because we are such visual people. We love audio, we love visual, we really connect with that on a lot of levels. But there is a question that a lot of people have a hard time explaining, so pretend you're at a networking party Eran. And someone comes up to you and says, “Hey, what do you do?” What’s your ten second reply?

Eran: I create experiences that leave people better off hopefully. So that has a lot to do with software, so I help startups, mostly startups create better products and better software experiences. And in my personal projects that are more contemplative in nature, it's basically still the same theme. I like to take someone through an experience that it would leave them better off on the other side.

John: So basically you need more than ten seconds to explain yourself?

Eran: Was that more than ten seconds?

John: Only by a little bit. But it's tough, you know, and that’s why I love asking this question because I struggle really sharing what I do with other people. And, you know, it always for me has to start off with, “Well, do you know what a podcast is?” And that’s always a tough conversation, so it's really interesting. But what I want to focus now Eran is your entrepreneurial origin story of what you're doing right now. So I'm talking about your current passion, you got there somehow someway. How did you come to do what you're currently doing, tell us that story?

Eran: A couple years ago I turned 30. I was single again after another failed relationship. I was working for a startup that was running out of cash. And not only was it running out of cash and we thought we may have to close the doors any day, but a process of renewing my visa that was supposed to be a mere formality, my work visa, ended up being a nightmare, a month long nightmare. And my immigration lawyer basically said you have to leave the country.

John: Wow.

Eran: So I – you know, after years of living in the city and paying New York City rents, and continuing to pay them, I spent a few months in Poland, actually two and a half months in Poland in Warsaw in one of our company’s offices, technical offices. Without paying New York rents, not really knowing whether I can ever come back. Not really knowing even if this company is going to survive, and basically having nowhere to go being completely disconnected from all my friends. And at the time, you know, I realize this is not the end of the world, and things turn out right in the end, but at the time that was very excruciating.

That was an experience of uncertainty like nothing I've ever felt, and something that really kept me up at night, and really – you know, I would get the sweats. I would get the night sweats. I wouldn’t be able to handle it so well. And when it was all over and things started – you know, from that point on actually things turned out really really well, like the visa got renewed eventually. I came back and we sold the company to Motorola in 2012. You know, everything was right, even that trip when I look back at it I did so many interesting things and met so many interesting people that I wouldn’t have otherwise.

And really why was I suffering so much? Why was I not able to live with this uncertainty? So that got me thinking about uncertainty and maybe other things that – other tricks we play on ourselves or other things we obsess about that aren’t really necessary because uncertainty is always there. You’re always gonna have to face it, especially in the startup in the world. And that started the path that eventually led me to writing this book, The Book of Hard Truths, and eventually lead me to start this degree that I'm doing in religious studies.

John: We obsess about the weirdest things sometimes as entrepreneurs. I mean, it can be the littlest thing, it can be the big thing, it can be important things, or absolutely inconsequential things. It's really interesting to kind of look back at the entrepreneurial journey that we've all taken and say: man, I can remember that I just spent sleepless nights that I had night sweats over XY or Z, and now it just seems so silly, or I can see why I had those night sweat because that was an intense period. It's really interesting to kind of look back in hindsight and identify it.

And you can learn so much Fire Nation and bring that forward with you into the future. And Eran, you're obviously living in New York City. It's not that cheap of a place to live, so what are you currently doing right now to generate revenue?

Eran: I'm sort of half New York City and half Tel Aviv now because I went back to my hometown after we sold the company, and I'm kind of living in Tel Aviv right now. But in terms of the money making machinery is that I actually started consulting, and I'm doing a ton of consulting for New York startups for the past year now almost. So basically this means ramping up the sales effort, talking to a lot of people, having lots of meetings. I'm hearing what kind of product people want to build. I like to come in very early, so I like to come in when they are just beginning to kind of form their first idea of a strategy.

And then we go through a creative process of talking to users and collecting user stories and trying to understand what users really need and grouping that into the sort of features they want. And we go through this whole design process and in the end hopefully there's something really great for users that users really love, and we go through a validation process with that as well.

John: One thing that’s pretty consistent about startups across the board is that they're tight with money. I mean, they're either raising money or they're going through a seed round or something of that nature, so are you actually just taking equity in these companies, or are you insisting upon actually getting paid in real dollars and cents?

Eran: You know I – everybody offers equity, which is funny because they –

John: Of course, take my company.

Eran: Yeah, exactly. They really shouldn’t. really they – if they really believe in the idea, even though they're a little bit tight on money, they should try to hog as much equity as possible. I generally don’t take equity in a company because as a consultant you have limited control on whether they follow your advice. So you can work really hard and come up with a product plan that you really believe in and then it just sits there. You know, if I were to take equity that would basically make an investor in the company, and then I would have to basically force some things on them.

I basically would have to put something in the contract where it says that I have to – I can pull out the equity and get my money back if they don’t listen to my product advice, which often people don’t, or they pick and choose, right? They pick the plans they like they pick, and then they ignore maybe what I think is the most important part. As a consultant you really don’t necessarily want to do that. As a VP of product, something like that, and when I was, definitely equity is very important.

But as a consultant, you know, unless is really believe in the idea, and it's someone who is totally on the right track and it's demonstrated well enough, you know, in that case I'm – you know, and I've already done that. I would take a percentage for remaining involved and basically being an advisor in the company long term.

John: So Eran, I want to shift the focus to your entrepreneurial journey. I mean, you’ve had some great times, you’ve had some great exits, but you’ve also had some struggles, take us to your biggest struggle. Take us to your worst entrepreneurial moment. I want to be there at that moment in time Eran, take us to that moment, tell us that story.

Eran: Oh, my God. Well, you know, I really think that the story I told before of being stuck in –

John: Yeah, but that was a vague kind of like step back, aerial brush over story. I want to see the pain on the wall Eran, take us to the worst moments.

Eran: There were a couple of bad moments.

John: Just one.

Eran: You know what? I'm gonna tell a different story.

John: Good.

Eran: You know, this is my entrepreneurship with writing. So probably the worse personal moment in my entrepreneurship is a 500 page novel that I never finished. And that’s in between startups and in between – and I actually took a long break to write it. I took a year off just to write that novel. And towards I would say the middle of that year; I've already had 500 pages written. I've done tons and tons of historical research; this is a massive historical novel tone kind of thing.

I just realized I wasn’t enjoying myself that I was actually not looking forward to waking up in the morning and writing every day. And one of my biggest realizations was, you know, who am I – why I am writing this for? What's the purpose behind it?

John: What was the premise of the book?

Eran: A massive World War Two novel.

John: Fiction or nonfiction.

Eran: Definitely fiction, it's a novel.

John: Okay.

Eran: So it was this massive novel and it was World War Two and it had Nazis and it had – it was in Italy, and it had spies, and it had – the main character is a psychiatrist who runs this insane asylum in the middle of the war and needs to keep it open. It was very – like, I could give you – back in the day I could definitely give you like a great pitch, where you’d think: oh, my God I need to read –

John: I have to read this.

Eran: I have to read this, right?

John: So what was the lowest of the low, like what finally was that breaking point for you?

Eran: The lowest of the low is just like sitting at home realizing that I'm burning through cash like crazy. That basically all of my savings are going on just writing this novel and I'm not liking it. I'm not enjoying the process. I'm not enjoying – like, and there's so many – like, you know, why was I writing it? And I think at some point I had realized this had more to do about me having some image of me as a writer than it was about the actual book, like for me. And that satisfied terrible motivation to do anything.

John: Well, Eran let me run something by you. I would love to get your feedback on this. There's a great book by Seth Godin called The Dip. And in this book he talks about how we all hit this wall and this plateau at the same time as entrepreneurs, where we're just not making progress, or maybe we're even sliding back down the hill, and often times that just the dip. That you just need to persevere through that to get to the other side and find success. Alternatively he also shares sometimes we're just in a flipping hole, and we're digging in a hole, and the only way to get out of the hole is to stop digging. What are your thoughts on that and share a big take away from your experience here with Fire Nation.

Eran: Yeah, so I read that book. It's actually a really good book. And when I read it I just thought I was in a dip and I kept on going, but I was in a hole. I can say – I mean, I think the key is do you really enjoy what you're doing, and what is your true honest to God motivation for doing what you're doing. And if you're absolutely 100 percent meditate on it, like be – I don't know take drugs if you need to, like figure out why you're doing what you're doing. And if it's not a good reason, stop doing it. And so if it's for ego, if it's for proving something to someone –

John: Those aren’t good reasons.

Eran: Yeah, if you want to make your parents love you because they didn't when you were a kid, stop doing it, it's not a good reason. You should do it because you believe in it and because you like it and because it's a vision that you just can't shake. And I think when I was honest with myself I just liked the idea of me being a writer too much and the action of writing too little in a way. Like, I still like writing, but fiction writing – it's like historical fiction writing that was not my thing.

John: My biggest takeaway here is a great book The Ten Biggest Regrets of the Dying. And these are terminally ill people, thousands that were interviewed and talked to. And by far the number one thing was I wish I lived my life on my terms, not on outside exterior influences. So when you said making your parents happy or making others proud, or proving somebody else wrong, those are all horrible reasons to do something Fire Nation. Whatever you're doing it should be for yourself, and then that audience that you are growing that is coming from that place of passion.

And Eran, I want you to tell another story now. This is an epiphany, a light bulb that went off at some point in your journey, so take us to that moment, tell us that story.

Eran: In terms of epiphanies, there are always epiphanies. The biggest one is probably for me the sense of it's not about me. Like, when I'm doing something it should be for the result. It should be for what I'm creating.

John: So what's the story behind this though? I mean, I understand the notion of it, but what was that moment that this epiphany happened, take us there?

Eran: With the writing, this is exactly how it happened. I told the story of basically suffering a lot through the writing, just waking up every day and trying to force myself to write and not understanding why. And thinking about it and meditating about it. And kind of going deeper and deeper into what are my reasons for writing it, and do I really believe that this is a good story? And do I need to – like, would I do it again? If I could choose now from scratch to start working on this project would I still do it?

And gradually I started realizing that A, no, I wasn’t really enjoying it. I was more enjoying the thought of having done that, than the actual doing of it. And B that life is short and this is actually – you know, I think in a weird way this all started when I watched a Steve Jobs speech after he died. So he died and then –

John: Was it the Stanford commencement speech?

Eran: Yeah, exactly.

John: Oh, so good.

Eran: He died and then I rewatched that speech on the day that he died and it really touched something. If you're doing the same thing – you know, he’s asking himself every day, if this was the last day of your life would you still do what you're about to do?

John: And then when you say no enough days in a row, you need to step back reflect and figure out what's wrong.

Eran: Exactly. I watched that and it definitely sunk in. I think it made me make a couple of career changes, but really not rethink the writing stuff. But when I started working on this writing and I was doing this day in and day out sitting down to write and not really enjoying it, and not really seeing why I'm doing this. You know, I forced myself to sit down and think about it. And the answer was at this point I just wanted to finish it. I just wanted to get out of it. I just started something too big that I wasn’t enjoying and it was just a matter of pride.

John: And again circling back pride is not the reason to complete a project or to continue down a path. And Eran, I want to ask you a specific question. What is your biggest weakness as an entrepreneur?

Eran: I think it's the need for certainty. It's both in how excruciating uncertainty can be for me sometimes, especially when it feels like there’s nothing I can do; I'm just waiting for someone else to make up his mind. I experience that as a lot of – really excruciating. And the other is you know, I think we all fool ourselves in little ways to feel like we’re more certain than we are. And for years, I was very good at that. Basically you give me a problem, I knew the solution. Like I'd be the answers guy. I always had the answers. I always knew what was the right thing to do.

And that can lead you in really bad directions because you can stop listening to other people. Because you have the answer, you're not looking for more information. You know, I think I'm much better today than I was then.

John: Well, on that note Eran, what is your biggest strength as an entrepreneur?

Eran: I would say today it’s not lying to myself. So I like that I can be enthusiastic about something and yet totally realistic about the chances at the same time. Just look at the chances very coldly and say: yes, it’s a great idea but that’s a theory; now the testing begins.

John: Now, of all the things you have going on right now, what’s the one thing that you're most fired up about?

Eran: I'm really enjoying the religious studies degree. I've been an atheist my whole life. I've been completely detached from religion; not interested in it, or intersected in it as a problem that needs to be solved, in a way. But now I'm reading about – so I have courses about Buddhism, I have courses about the psychology of religion, the philosophy of religion, the anthropology of religion. And I'm really learning a lot. And I'm basically on a quest to try to figure out what are the treasures hidden inside all these different religions that could be secularized and brought to a wider audience.

Because in a way, I think that’s the next wave. We’re building more and more smart technologies that make our lives easier. And really the next wave is probably going to be the layer of psychology, of making us happier.

John: Am I seeing a future illustrated book?

Eran: I don't know if it’s going to be illustrated but definitely another book, and maybe also a piece of software. Maybe also a software startup.

John: A little sass mixed in there. That’s always a good thing.

Eran: Exactly, exactly.

John: So Ron, we’re about to enter the Lightning Round. But before we do, let’s take a minute to thank our sponsors.

Ron, are you prepared for the Lightning Rounds?

Eran: I'm as ready as I'll ever be.

John: What was holding you back from becoming an entrepreneur?

Eran: Thinking that I wanted to write books for a living.

John: What is the best advice you’ve ever received?

Eran: This is gonna be really cliché but it’s absolutely true: follow your heart; follow what feels good.

John: What’s a personal habit that you have that you believe contributes to your success?

Eran: I say no to almost nothing. I say yes to everything. Balancing it is tough but every opportunity comes my way, I take it.

John: Do you have an internet resource like Evernote that you can share with our listeners?

Eran: I really like an app called Day One. It’s basically a journaling app for the iPhone and I think also for Android. But it’s so clean and beautiful and it captures all that information from the environment. It captures the date and the temperature and your recent picture and everything. So you can just write down and it creates this stream that’s very useful to follow kind of the development o f your thoughts.

John: If you’d recommend just one book for our listeners, Eran, what would it be and why?

Eran: I'm assuming the listeners are entrepreneurs. I love the book Living Beautifully with Uncertainty and Change by Pema Chodran. She’s a Buddhist teacher and it’s a great book. And I think anyone should read it, but especially entrepreneurs.

John: Well Fire Nation, I know that you love audio so I teamed up with Audible. And if you haven’t already, you can get an amazing audio book for free at eofirebook.com. And Eran, this next question is the last of the Lightning Rod, but it’s a doozey. Imagine you woke up tomorrow morning in a brand new world, identical to Earth but you knew no one. You still have all the experience and knowledge you currently have. Your food and shelter taken care of. But all yo have is a laptop and $500. What would you do in the next seven days?

Eran: Yeah, so first I want to say if food and shelter are taken care of, what else is there? I would just sit there and meditate all day. That would be awesome. But you know, I'm assuming I have a laptop and no internet connection so that kind of sucks. So I will have to restart my business. And the amazing thing about my business is I can do it from anywhere with a laptop. So I would just basically start exactly the way I started a year ago. I would go out, search for all the relevant types of clients, email them like a nice introduction email, tell them about my services.

I have the same skills and the same abilities. And things will start rolling from there. And judging from the past year, it’s gonna happen pretty quickly. That’s really amazing. We live in a world where anybody – anybody with a laptop can actually start working and making money Day One if they have the skills.

John: And all they need to do is develop those skills. And you are a freelancer. And those skills – I mean $25 a month from Lynda.com, You Tube videos; it’s all out there at our fingertips, Fire Nation. And Eran, let’s end today on fire with you sharing one parting piece of guidance, the best way that we can connect with you, then we’ll say goodbye.

Eran: Know your motivation for what you're doing. Figure it out. It needs to be really good. It can’t be about your ego. It can’t be a bout yourself. It has to be about the change you want to bring into this world. And don’t lie to yourself. You're going to waste years of your time just lying to yourself about your motivation. Don’t do it. And this is not just from personal experience; this is from a lot of startups that I'm working with. Don’t do it.

John: And what’s the best way that we can connect with you?

Eran: You can find me at erandror.com – that’s E-R-A-N-D-R-O-R- dot com. And if you add the words hard truths – slash hard truths, you’ll find my book.

John: Fire Nation, you're the average of the five people you spend the most time with and you’ve been hanging out with Eran D. and JLD today so keep up that heat and head over to eofire.com and just type eran in the search bar. That’s E-R-A-N. His show notes page will pop right up with everything that we’ve been talking about. Of course you can check out his book directly from the show notes page; we’ll have it linked up. Or just erandror.com/hardtruth. An Eran, I want to say thank you for sharing your journey with Fire Nation today. With that, my friends, we salute you and we’ll catch you on the flip side.