The first time I saw today’s podcast guest was at a conference for startups, in 2009. I remember Vladimir was very composed and knowledgeable, while I had just graduated and had no idea what I was doing.

Vladimir was already building his company, uberVU, which later got acquired by Hootsuite in one of the earliest – and biggest – success stories in the local and regional ecosystem.

“I co-founded the company, led the development of uberVU’s first products, raised financing rounds, recruited top talent, brought strategic partnerships to the table etc.

I also recorded video presentations, brought coffee for the engineers or cleaned the office. I was a founder, which meant I had to do anything needed to make the company a success.”

uberVU’s development and acquisition paved the way for many startups, prompting many founders to learn from Vladimir. So through the last decade, I saw him at various meetups, events, and conferences, generously sharing his insights.

Vladimir always struck me as a very outspoken, no-BS person, who has a deep understanding of the topics he talks about. His clarity of expression reflected clarity of thought and that stands true to this day, as you’ll learn yourself if you listen to the episode we recorded together.

What Vladimir doesn’t know is that I was hugely intimidated by his knowledge and experience, so asking him to be a guest on the podcast took much longer than usual. What came out of our conversation is a range of ideas and questions that can help anyone upgrade their thinking and their actions – not by imitation but by strengthening their own critical thinking.

About Vladimir Oane:

Vladimir is a modest, deep thinker whose ability to remain rooted in reality is the result of hard work, taking information consumption very seriously, and optimizing for who he is as opposed to following prescriptive “success” models.

If the phrase “it’s very hard to do a Kanye West on a book” piques your interest, I promise there’s a bit of fun in this episode too, along with valuable lenses you can try out to improve your outlook on life, meaning, decisions, and your creative pursuits.

Listen to this episode to learn:

  • The fundamental role plays accepting reality in for your life and decisions
  • How the scripts inside our heads lead us to stressing out, pointing fingers, and other counterproductive reactions and behavior
  • How being aware of your own tendencies (to overthink or procrastinate, for example) makes it easier to find people who complement you and help you avoid going to extremes
  • What Vladimir uses instead of mental models to cultivate a rational perspective on life and make judicious decisions
  • Why reading with a detective’s mindset can make a big difference on what you do with the information you take in
  • Why writing is instrumental to any creative outcome, no matter the industry, because writing is a tool for thinking and because it’s immensely valuable for non-prescriptive jobs
  • How to activate the knowledge, ideas, notes, and information you gather in time.

A few ideas that stuck with me:

  • “We’re not trained to make as many decisions on a daily basis as we would like” – We wrestle with a wider range of questions than our grandparents did and they can become debilitating because we haven’t mastered the ability to make so many choices without getting depleted.
  • Truly accepting reality is key for levelling up – People who manage to stay calm in times of crises base their decisions in their deep and truthful acceptance of things as they are, instead of wasting energy on things as they should be.
  • The quality of the reasons for starting something (a company, a project, a job) are decisive for its survival through the crisis we’re experiencing.
  • “Intuition is our AI” – We can build better instincts if we’re more aware and become more introspective of our past decisions.

Connect with Vladimir:

Resources mentioned in the episode:

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Full episode transcript:

Andra Zaharia: Podcast guest is Vladimir Oane. He’s been an entrepreneur for more than 10 years, and he’s gathered massive experience building a product that was acquired, and that later became part of a bigger company. So, it’s clear that he’s had to make plenty of decisions from what strategic direction of the startup would have to hiring to choosing how the product would work and how it would evolve. He’s a guy whose way of thinking I appreciate immensely, his perspective on life. He’s very structured approach. He’s no bullshit, the way of looking at things and talking about things and something that I’ve always admired and respected about him. And I’m really glad to have him on the How do you know podcast, because it gives me a chance to dive deeper into how he articulated his way of seeing the world, his actions and his habits in a way that ensures he’s adaptable. And he’s able to thrive in complex and quite uncertain environments such as the one we are dealing with today. Currently, Vladimir is the co-founder of Deepstash. An app whose goal is to help you become more inspired, wiser, and productive through bite-size ideas. And the way that he approaches this new company, his building is truly inspiring. And you’ll see why during our conversation. So, in this episode, we explore many of the aspects that tying to decision-making from both like a general wider perspective, but also tying in Vladimir specific experiences and the way he reached certain conclusions and what he saw worked for him. And could maybe work for you too. I love that Vladimir has never prescriptive and his approach. He always asks thoughtful questions and he triggers. Reflection. And self-awareness in a way that helps the people around him level up including myself. So, I hope you’ll enjoy this episode and I hope it serves you well in this time where we all need a bit more clarity, a bit more focus, and a bit more objectivity around our choices and their influence on the rest of our lives. Thank you for listening. I’m really glad that we’re finally getting to do this and have this conversation. At the same time, I wish there were. There was a more positive context around this, but I think that in times like these, it’s even more important to talk about… to just pay attention, first of all, to the traces that we’re making.
And then to maybe talk about what helps us stay saner and hopefully productive. And if we get lucky, even creative these days. So, thank you for making the time to be on the show.

Vladimir Oane: My pleasure.

Andra Zaharia: Happy to have you. I wanted to start by asking if you feel that decisions are becoming more important these days, you know, from small ones to big ones, when everything around us seems beyond their control, how important do you think decisions are?

Vladimir Oane: As important as they they’ve always been. I think they’re as important as they were yesterday. But yes, I feel like we are leaving aside the current events. I think we are progressing towards a place where we feel the burden of our decisions more and where we were asked to make more and more decisions. So, this is mainly because we’re all connected and we all see what everyone else is doing. And we get the more ideas we have. Our levels of ambition is going up, but also because the valuable parts of our economy are becoming less predictable and more uncertain, chaotic. And while this is good, I mean, like dynamism in any economy is usually a good thing, We, perceive this as an emotional burden and it’s scientifically proven. And decision-making kind of depletes our willpower and makes us more miserable. So in the last decades, we are asked to do more, to make more and more decisions on a daily basis. So, I think decisions whereas important as ever, but yeah, we are aware of and required to make more of them on a daily basis.

Andra Zaharia: More of them, both for ourselves and others. And maybe this is something that, until now, in our daily lives, we sometimes pay attention to how we make decisions.
But more often, we had all these automated kinds of behaviors and habits, which is normal because that’s how our brain keeps functioning and it’s able to handle more complex tasks than just, you know, deciding what to wear every day and things like that.

Vladimir Oane: Of course. But it’s not, I know deciding what clothes to wear because we now have Instagram and we know like every day is a show. So, we have that burden of additional decisions, but in more fundamental ways, I mean, a pre-enlightenment, let’s just say most people, I think, lived lives that, that, I don’t know, have very, very little variation. I mean, like mostly because people didn’t travel, they didn’t have access to information but also societal pressures. So, you were born, you were probably going to do the same job as your parents did. You’re going to get married, have kids never leave your village, go to church every Sunday. These decisions are pre-made for you by the church or whoever was in charge, and then you died and the new generation kind of went to do the same motions. After enlightenment, then our economic boom, by the industrial age. Everything is up in the air and for discussion. I mean like more people nowadays are atheist. So, like, what is the purpose of my life and what is good and what is bad? All of these are our questions, very deep way questions that we kind of have to deal with. Of course, we don’t live on a planet of philosophers. Now people have to make these micro-decisions and they have to think things true way more than our grandfathers and grandmothers. So yeah, I think in in this way, we’re changing and of course, then we have to decide what to wear and include to impress, and all of these micro decisions, but even like the big decisions. Like “What’s my purpose in life?” What should I think of my life? I mean, this whole idea was not a question that our grand grandparents asked, like, I don’t know I’m here. I’m going through the motions and that’s it. Now it’s like “Should I be happy? What is happiness? What will make me happy? Would a career make me happy? Whether a relationship made me happy? Should I travel? I saw that guy on Instagram. He’s traveling a lot. He seems happy. So, should I do like him and be like her? Will that bring me happiness? But maybe it’s not happiness. Maybe I should help other people. And I should be more altruistic.” All of these are like very debilitating questions. And even if you don’t ask them rationally, they can really take a toll on our emotional wellbeing. Especially since I don’t think we’re trained to make as many decisions on a daily basis as people.

Andra Zaharia: Absolutely. And we can see how people react when they feel this overwhelm. We’ve seen this a lot nowadays. So as you were mentioning throughout history, there was a rather set course for life, I guess. And even nowadays there are still, I mean, remnants of that would still kind of direct people towards the next stage or the next step in their lives. But now, especially now with the level of uncertainty that they’re seeing, that we’re seeing, when we look ahead, at least some of the people, not everyone, I feel like everyone around us, even in our bubble, people are still a bit… They’re kind of in this belief that this will be like a big thing for the economy and that there will be like major shifts and major transformations and very delicate, very uncertain on foreseeable future for us. But the people who kind of sit with these questions, especially these days, will have to deal with a lot more self-doubt and a lot more, I don’t know, grappling, trying to fumbled through the dark for some answers in something that seems like stability, I guess. So I wanted to ask if you’ve seen people making more emotional, irrational decisions in times of uncertainty and what’s different for people who managed to stay calm and who managed to stay connected to, let’s say, more objective way of seeing things.

Vladimir Oane: Well, yeah. I mean most people make; I think we all make irrational decisions. I think the difference between us is that, most of us only make rational decisions and a few people out there managed to have a small percentage of their actions being guided by what we can call a rationality. But yeah, I think what all of the rational and a guarantee in times of crisis, we show our true colors, if you will. So yeah, I mean, I had no expectations that we would behave rationally. I mean like why do some people stay calm? And, I think this is very important and it’s probably one of my biggest realizations over the past few years in regard to decision-making. Probably living a good life comes from this idea of acceptance. I think the issues like the one we’re going through these days pressure people and create fear, but it’s fear because we cannot accept reality. I think accepting that the world is a certain way is probably the biggest thing that someone can do to live a better life and make better decisions. Because fundamentally, I think all the issues stem from this nonacceptance of reality. I mean, like we’re going now to a pandemic. That’s the reality. Shit is going down. Things are going to get bad. So, you can accept it and be aware of the situation, but not accepting it as is, I don’t know, like watching TV, but deep down accepting that this is the, how the world is, unfortunately. And then, in this canvas thinking about your decision-making. but if you start with the assumption that what we’re going to right now, or any problem in the world, it’s like some sort of an injustice that has to be corrected by someone, by God, by the state, by whoever you think is in charge of your life, will create a lot of anxiety and unhappiness. So, for me, I think everything starts with this idea of awareness and acceptance of reality. Oh, it sounds… yeah. Now like everyone accepts reality, but I don’t think people accept reality. We don’t, first of all, we do not experience absolute reality. So, what we actually experience in life is an interpretation of reality to our senses, our emotions. So, we all live in the world that is running by a script that we all have in our heads. So, most of them accept reality. And when events happen, that kind of contradict the script that we have in our head, like, “Oh, this shouldn’t have happened. This major event shouldn’t have happened.” I don’t know, my girlfriends shouldn’t have cheated on me or my company shouldn’t have gone bust or whatever. We think that this is like a glitch in the system and we don’t usually, we don’t change the script in our head. We usually blame someone else or we just feel an anxious and we get stressed and so on and so forth. All of those are counterproductive and I mean, any sense of calm and serenity in the event of some negative, event is the baseline for living a proper life going forward. So, yeah, I think that that makes all the difference. And today you see a lot of people focusing on, when it comes to decision-making, on tools and hacks and tactics. Like “How you should make decisions like Jeff Bezos. Here is how he makes decisions” or “Here is the five-step rule to do this”, that I don’t know, Warren Buffett is doing. And if you do these five steps, you’ll be like Warren Buffett. Kind of like, I don’t know, the Nike ads, liken you aware of these pair of shoes and all of a sudden, you’ll be as good as Michael Jordan, playing basketball. And of course, that’s that superficial, because if you want to be as good as an investor, as Warren Buffet, you don’t need his methods. You need his underlying rationality and you need his brain. You can have glimpses on how he looks at things, but Warren Buffet is as irrational as most people. So, a lot of his decisions are emotional. It’s the thing that we have to and scares. How does he interpret his emotions? How does he relate to his life experiences and stuff like that? And that’s very hard to replicate or even access. So, the level that I’m talking about, this awareness and acceptance of reality is like very, very philosophical, but it’s like strategy. It has to start from an epistemological level. Like “How do I see myself in this environment?” And the answer to this question will make all the other tactics more or less important. So yeah, I mean, like look at the world accepted… there are, I don’t know, a lot of thinkers in the world that are talking about this from the ancient Stoics to, I don’t know, where it startled to, whatever, in the previous century. So, lots of thinkers deal with. With this acceptance of, of reality as the cornerstone of a good life.

Andra Zaharia: And it absolutely still is nowadays as well. And while you were leading us through all of these kinds of how these concepts work together and how these ideas have worked together throughout history, because the concept of acceptance has withstood the test of time, simply because it’s a given for any generation, any society, any type of culture or any type of issue that we’re maybe confronted with. What I noticed is that, frustration, that the misalignment between reality and the reality that we expected to live and to felt like we were entitled to. The frustration that arises from that can actually push people to try to control a lot of what’s going on around them, especially for people who have a higher need for certainty like I am. And I’ve been battling with these kind of control issues for a long time. I wanted to ask you if there’s a way when the pressure is on when the stakes are on. If you have a way to kind of figure out what is within your control and focus on that to give you some sort of footing in in that situation.

Vladimir Oane: Well, yeah, I mean, I think you already pointed out. What I am trying to do is like focus on what’s under my control. I don’t always manage to do that, but I think that would be my guiding, a set of principles. Like figuring out what I can do and how I can influence the situation and do that, focus on that part. And of course, in many, many instances, we focus a lot on things that we cannot control. Like right now, there are plenty of debates on what will happen, what happened the whole pandemic. And I mean, everyone is kind of like an orange chair strategy these days. Although the situation is beyond the control of most of us, those discussions are pretty much pointless. But those are these discussions. I mean, it’s way easier to talk about macro events and I don’t know, discuss about conspiracy theories then I don’t know, looking in the mirror and figuring out what we should do better about ourselves. I mean, that’s kind of the issue. I think it’s a form of procrastination what we’re doing. I mean, especially outside of like, let’s just say politics, but it happens in the work environment as well. I mean, so many people are doing like politics and discussing how all the ways in which their bosses suck, or I don’t know, why this project is the wrong one and stuff like that. And, why, because it’s. easier. It’s easier than, I don’t know, focusing on your stuff and accepting reality. And what comes out of that acceptance and getting down to the things that you can actually have under your control people. I think we don’t like to have responsibility for many, many things. Actually, I think the more responsibility we get, the more pressure is for some people and they run away from responsibility. So, yeah, I try to focus on things that matter. That’s easier said than done. I know the theory, but I do catch myself in many, many ways on focusing on less important stuff. And that’s because I have this tendency of boiling the ocean and I want to understand something in detail before I can, I don’t know, make a decision or decide what it is that I should be doing. And after a while, that’s just, I don’t know, procrastination. I’m looking at things from all these angles, because I want to postpone making a decision or deciding I’m doing something. But yeah, I’m aware of my tendencies and I’m lucky that my colleagues are much more pragmatic than me and they keep my desire for intellectual precision in check.

Andra Zaharia: It’s super important to have nowadays kind of a, let’s say, just a group of people to share ideas with, whether it’s colleagues or community, or I don’t know, mastermind group or whatever it is. I feel that we all need each other these days to keep, just to maintain our sanity and to make sure that we’re not running golf in any extreme direction. If that should happen, you mentioned your colleagues and I would want to ask: Your experience as an entrepreneur is so, so long, and it covers so many experiences from early stage to high growth, to selling a company, to advising so many startups and talking to them and watching them pitch and pitching yourself so, so many times. So, you’ve seen the type of, let’s say, usual behaviors that startup founders have when they’re under pressure. And there is a lot of pressure, especially in the early stages when looking for funding in all these situations and experiences. I wanted to ask what exactly from these experiences makes you resilient in times of change and what helps startup founders become resilient? Because it is going to get very tough for everyone and especially for startups who have to be scrappy and have to be, just very resourceful in general, but now it’s just became, it just became like 10 times harder or even more than that.

Vladimir Oane: Yeah, sure. It’s going to get harder. It’s already harder for all the companies. I don’t think there’s a large segment of companies in the world that are doing extremely well.
I think startups will feel the crisis very, very hard. A lot of the startups will die, not that many survived anyway. But yeah, let’s just say that the bloodbath will be more severe this time. The issue who is on the emotional state and the mental clarity of the founders. I mean, if they are well grounded. I know managers to keep their team engaged and they have a clear sense of purpose and direction, then they have a bigger chance of surviving. Because maybe like companies’ early days, they live and die by the enthusiasm and the vision of the founders.
So, if those people who started the company are okay, then I don’t know, there’s more likely for the whole team to continue to operate. If they get paranoid and irrational and stuff like that, then probably the company doesn’t have a bright future. And now we require those virtues more. Usually, one thing that I would focus on is focus on the reasons that made the founders to start that company in the first place. And then, there are good reasons to start a company and bad reasons to start a company. The bad reasons are “I want to make a lot of money and I had this… there’s this trend in, like, I don’t know, robotics or AI or machine learning or virtual”, whatever. And people seem to be making a lot of money. So, let’s jump on board and get our cut, right? Or just want to be the boss. “Nobody can dictate me. I want to be in charge for a while. “ I mean, there are a lot of like silly, ego driven reasons that make people start companies and while a lot of them succeed, I don’t think that’s enough to pull you to a crisis, like the one that we’re going to. So I would more faith in companies that have started there, where the founders were emotionally invested in a problem. They care deeply about that problem. They understand it very, very well and they have a purpose. Their companies are an extension of their desire to do something good in the world, in a specific segment of the economy. So, yeah, that’s kind of what I would focus on. If I were an entrepreneur, I will be thinking like “Do I really want to do this?” Like, “Do I really want to do this when we would have run out of money? Do I want to go without pay for, I don’t know, a long time? Can I?” I mean, if, your whole reason was to make a million dollar fast, that’s unlikely to happen in the new context of the economy. So, you might be very disappointed by the outcome. So yeah, I would focus on like, what are we doing this? And if entrepreneurs are committed, like they think that they have found something that is really meaningful in this world, then I think you’re on the right path and the other challenges you may approach them with the right perspective.
I think in these moments of crisis as entrepreneurs, you have to really pause and think if what you’re working on is really meaningful, speaking about why you started a company like, “Do I am really adding anything of value to the world?” And of course, I’m not saying that a lot of the companies who are optimizing like these parts of a value chain are not important, but you should care about that. I mean, like if you’re doing it, like I have this AI based ticketing system and I’m just doing it because I could do good PowerPoints and I can link five hype words type work together.
Then I think, personally, that this next phase will frustrate the hell out of you, especially if you have zero empathy with your users and potential customers. So, yeah, that’s what I would focus on, like the intentions of starting this company. And hopefully those intentions are virtuous enough and powerful enough to pull you out of it.

Andra Zaharia: Absolutely, and I think there is also something that’s connected here having this vision, maybe not the perfect vision of having a mission, having kind of going back to your why and making it very clear. We’ll also kind of filter the people around the founder, whether they’re supporting members of the community or employees and so on, and those who will who actually believe in the same thing, and who are aligned with the founder. I think they have a better chance of weathering this through and kind of sticking together and making their work count because we’ve never experienced something like this, like the current pandemic. I think that there might be a shift in the way we perceive value and the way we evaluate value, but maybe I’m being a bit too optimistic and idealistic. But in every crisis, there’s this opportunity to refocus our attention on what actually matters, on what we actually need as well, a world as people who are connected together. And I think that now is more obvious than ever. I know that maybe this doesn’t sound perfect, but I feel like there’s a bit of irony here. This purse, this outbreak specifically has taught us how much we depend on one another to actually be healthy and stay alive, which is something so basic and something that we take for granted. So often, there are going to be some very deep social implications here that basically can change the face of society. And looking at what happens, at the shift, looking at ourselves in this context, I think that it would be helpful to rely on some mental models that point us in the right direction. Especially because we’re going to have our brains scattered our mind, scattered all over the place. So, it was curious because I know you’re in not just an avid reader, you’re a reader by excellence. Not just because you read a lot, but because you take so much from what you read and you also share it with others. I wanted to ask, you know, what mental models are your kind of go-to tools, mental tools, these days, in general?

Vladimir Oane: I was a big fan of mental models. I studied them all. They didn’t make me a more rational person. I found, I mean, I think… They’re interesting if we want to rationalize our best or past events, more than animal health has improved going forward, but they are fascinating. I mean, I looked into all the blogs and interviews. I know it’s a trend with mental models. They didn’t work for me as a personal tool. Not because I don’t think they’re awesome, but I don’t think they have practical value. And, in a way I kind of change my perspective a little bit on rationality. I’m going to tell you what my current interpretation of rationality is, like kind of what I’m doing. I think we used to think of rationality, in very, I know extreme terms. Like, I don’t know people are… we should aim towards like Spock, like a method of reasoning. I’m talking about the Star Trek, of course. That’s an ideal of rationality and you have like philosophers in the past, like from Aristotle to like, I don’t know, random, I mentioned earlier that I have this huge respect for rationality and people who live a rational life. But I don’t think that’s a representation of how we experienced reality, to be honest. And I even like some brain studies, like, for example, if you ask someone to pick a ball out of many from a table, you will see that the part of the brain that we use for a reason gets activated after we have started to reach for the bowl. So, the, the decision is made first in rationality kicks and second, with that experiment in mind. I mean, of course it can be can be extended to other decisions, but a lot of our decisions are subconscious. We try to use our reasons just to explain why we did certain things, to explain to ourselves, first of all, why did they reach for the red ball and not the blue ball? And then you’ll come up with a story on why red is more important to you, but you didn’t pick red. I mean, the decision was made before, whatever you think is, you kicked him. So, the reality is most of our decision-making, probably 99% is done subconscious. But still, we’re making a lot of decisions on a daily basis. I think the number is like 10,000 an hour decision, that micro decisions that we have to make, clearly rationality will not help us here. So, in a way, I kind of break decisions into two batches. More like important irreversible decisions, where I think having a pause and go into some sort of a process is important, but for the rest of this decision, which kind of make up the bulk of your daily experience, I started to be much more appreciative of intuition. And I think intuition is this mechanism that our AI, if you will, that kind of automates some responses based on our past and our emotional past. So, I think how we instinctively respond to something really, really important, but how can you train something that you cannot control? I think here, and I’m not really sure that this is the right method, but I think we can build better instincts if we are just more aware of introspective of our past, best decisions if you will. So that can take, that can be, I don’t know, like any sort of meditative experience, whether it’s like a Tibetan style and meditation or for some people I don’t know, going to church and praying, or for some other people is, I don’t know, walking in nature, but having, having time to look at your life objectively from like a third person perspective. It’s very, very useful because if whatever your subconscious is or whatever consciousness is, who’s making all these decisions that you now have to have to justify, I think, I think it’s important. Because I think we, people, look at their brain and their intelligence like a CEO in the brain, like the big boss, who’s making all the calls and, I wear this little genius in my call. But yes, I mean, like he’s a really powerful person in my head, but actually our reality is different. I mean, the voice in our head is more like the PR department then the CEO of the company. I mean the PR department who has to make up reason for all the fuck-ups that that happened. Yeah, well, I think the red bull, because red is an important color to me, of course I highlighted, I green-lighted that shitty project, but based on the data that I had at the time, it was a brilliant project to start then. Of course, we’re making very good at justifying our actions. So I think by focusing on understanding, or at least realizing what it is that we’re doing, because a lot of these we don’t even realize the decisions that we’re making. Having this set up time for introspection, I think in time we’ll lead to better intuition because if we observe ourselves and we think about the things that we’re doing, hopefully, we’re going to make smaller and smaller, but better and better decisions. And of course, for the big projects, the important decisions let’s just say, those for me are the category of “What should I do with my career? Should I keep my job? Should I become an entrepreneur? Should I marry this person? Should I have a kid? Should I start a company?” I mean, like all of these big irreversible decisions, I mean, you only have a few of them on a yearly basis and probably tens of these decision in your life. And for them, I think pausing and not using your instinct it’s probably helpful. But here I’m not using like a mental model, like “I’m doing this technique of making a decision.” I use, I don’t know, ethics in a way, because fundamentally when you ask why enough times you get to like very deep, deep shit, you know, “I need, I want to change my job, but like, why do I want to change my job? Well, I’m unhappy. Like what makes me unhappy?” So, okay, cool, I don’t like this job because by one of the work and more ambitious projects. So, what sort of projects? And you go into these like journeys of understanding of “why”. Why that decision is important to you and going through that process, you find out what are the elements that you have to optimize for. So, in a way, you are deconstructing the problem into variables that you can operate with, and, you know, at least what you’re optimizing for and what the shortcomings of that decision might be. You are building a vocabulary and a set of tools to work with the problem. But yeah, for on a day-to-day basis, I’m becoming more and more appreciative oof instinct. And by the way, I mean, like, I’m a rationalist, I like reason more than anything. I love the enlightenment and stuff like that. So, it’s weird to have this appreciation of, I don’t know, spiritual, spiritual practice. Well, yeah, it’s an acceptance of reality. I think, Spock, he’s a TV character, he’s not reality. And we, we don’t look like him. So, we have to optimize for who we are not, the, the characters in the TV series.

Andra Zaharia: I love that modeling your own critical thinking, your own kind of way of connecting and reconnecting with yourself, especially when it gets tough. These can be so, so super valuable and it looks so different for everyone. And I love that you mentioned that there are no shortcuts and there are no hacks because I feel like we need to say this. And we’ll need to say this for a long time going forward, simply because for such a long time, they’ve been served on various platters online and offline and everywhere else simply because they’re appealing to people and there are easy ways to get a craving. It kind of gets out of section for a craving you’re having, and I feel like everything you described this personal method of yours, kind of this process that you build is really actually building a way to trust yourself when you make choices, especially these small ones that you can’t think through every single day, because it would simply not be feasible at all. Trusting ourselves these days, I feel it can be very empowering, especially because we need a little strength and the little extra kind of, not just extra resilience, but faith in our ability to do things and to pull through difficult situations and to navigate uncertainty. And a lot of complexity, it feels like complexity has simply exploded in our, all our faces. Not that we didn’t deal with it before, but you had like a way to kind of hide that complexity on their various habits and social interactions and matter of doing things, but it’s just exploded. And now we have we have this. What do we do next?

Vladimir Oane: Clearly, a lot of the fear and anxiety, and what we experience in our life comes from the fact that we don’t feel like we’re in control. And a lot of that comes from the fact as that we don’t understand why we did certain things or why certain things happen to us. And that tension comes back to the core realization that I mentioned earlier of accepting reality, but connected to that is accepting reality. And the other thing is to accept that you are the first responsible for your own life. Your life is your life. So, everything that you do, I mean, your life is a reflection of your action and it’s your responsibility to improve it. And if more people will be focused on their true life, their true sense of individualism, let’s say, I think we would be better off as a society because a lot of the stuff that’s happening right now with the pandemic is just pure emotion, right? There’s is no responsible sense of communication because if you would respect your life, you’ll be focusing on your life. And what means a good life means to you? And maybe it’s like, I don’t know your parents or your company or your community. And you focus on that. But what most people who don’t think they’re in control of their life or that their life is their responsibility, all they do is look at the news and be outraged. Because we don’t like to be responsible for our own existence, because I don’t know looking reality in the eyes, looking at yourself in the mirror.

Andra Zaharia: It does, it does, and it takes guts. It takes not backing out when you don’t like what you see in the beginning. And, yeah, it definitely takes time.

Vladimir Oane: But looking yourself in the mirror after you’re doing it for a long, long time, actually, develops your self-esteem you mentioned that correctly. I mean, like once you understand yourself and you know yourself, with good and bad, then you have this accepting of yourself and reality that makes you very confident because you know what you’re working with, you know, the environment, and if you know, not only do you know it, you accepted it and you know what you can bring to the table, where your strengths are, what your weaknesses are.[ You’re aware of, of the, the power that you can, you can unleash in the world, the creative power, the positive, hopefully power, and also, you know, your limitations. And of course, that’s the difference between confident people and people who suffer from Imposter Syndrome.

Andra Zaharia: It’s long way to this and it may not be accessible for most people, especially now in the beginning and sitting alone. Not just alone, but sitting in your home and, you know, having less things to distract the mind with, not that the internet and the TV don’t provide enough. Maybe an opportunity to do this, practice of self-reflection. But to get there, we have to eliminate some triggers and we have to peel away and just do away with some distractions and the biggest one. And I feel like something that can become very, very toxic nowadays is the news and in general, just that just drinking from the fire hose of news. That is pouring out every day, everywhere, nonstop. You can’t fly in the corner of the internet or any type of social conversation these days without running into the crisis, running into opinions, running into anything that’s remotely related to it. So, you have so many years of experience of going through an enormous amount of information and trying to make sense of it. And I like to talk about deep session as well, which is what you’ve built to kind of embodied this experience of yours and this pursuit of yours. That’s so long and go so far back. And my question here was how do you manage information overwhelm? What would you say are some key things that people should just consider when looking at everything that’s coming towards them nowadays, and going forward in generally in life?

Vladimir Oane: Well, I wouldn’t pay a lot of attention to news. And again, it’s easier said than done, especially these days where I’m as guilty as everyone else for refreshing certain tabs in my browser and trying to see if the Doomsday scenario got closer every day. But, in general, I try to distance myself from the news and there are large periods in the year when I have almost no connection to the news or the politics and stuff like that. I mean, a few months ago, I didn’t know that we have a new government, until like, I don’t know, a few weeks months after it happened. But it just was not important to me. I didn’t check it. I didn’t care. So, I had other stuff to focus on and I think that’s extremely healthy long term to distance yourself from this constant barrage of mostly useless information. So yeah, I’m not perfect, but I’m trying not to follow the news and not to get into politics. Not that I don’t have very strong political views, but I found that, I know the daily news or the discussions that happen in social media are quite unproductive. So yeah, no news, no politics as much as possible. But then the idea is like, what else, what else I consume? Well, I tried to read purposefully, whether there are like online publications or books or anything that I consume on purpose.

Andra Zaharia: Do you match your sources to kind of what you need to learn at a certain point or do you have like a plan? I don’t know, a reading plan of sorts.

Vladimir Oane: Yeah. Whenever I’m consuming something, I have a detective mindset. See, we came back to my sense, but yeah, my mindset is, I read like a detective. So, I’m trying to find the good elements in anything that I read, something that I can, that I can use. So, whenever I read something, I read it with the purpose to find useful stuff. And a lot of the content that I consume has no usefulness in it. It’s just troll away or it has entertaining purposes. But the good one that I stumbled across has a lot of like insights, pieces, things that I can use new ideas, new methods, things that inspire me, things that give me a creative angle that I haven’t thought about. And then when re-reading through that, I have to make sure that those insights find a way to become productive at some point. And, so yeah, I mean, my philosophy in terms of reading, I say it’s like I read with a pencil in hand. And of course, I don’t have an actual pencil, although my iPad has a nice digital one that I don’t use that much. But no, it’s like taking a lot of notes. I think taking a lot of notes of what I read and having a method to take this avalanche of notes that I collected over the years into something useful. For me. I mean, l we are going through a time of immense pressure because of unpredictability and chaos and stuff like that. So, the valuable people in our society, the most valuable ones are the people who can put some sort of an order into this chaos. And all the creative projects that are the most valuable in today’s economy are our projects that deal with making something out of nothing. Or at least something unique, not based on a recipe that, I don’t know, it was repeated over many years. So, I mean, you can see that in music, you can see that in technology and stuff like that. And a lot of like our daily jobs until recently, we have these geniuses who came up every few years and they invented some new stuff and then we all cheer, put them in our textbooks and be done with it. But now our daily work is impacted by that. We, most of us, we are required to do something that we’d never done before. And not that we haven’t done it before and nobody else has done it before. So, it’s not even that bad. I mean, it’s worse actually, because you don’t know what the outcome is or what it should be. You cannot even define it. So, I mean for a lot of the workers out there, there is so much uncertainty and coming up with some sort of a structure is the key. And in order to do that, you have to write. And you know that better than anyone that, putting some content together is very, very hard. But it’s not just for content, producers like queue. It’s for any creative outcome. Like if any project: if you want to send a rocket to the Moon or Mars or, I don’t know, you want to run for president or you want to create the next billboard album. It all starts with writing something down, right? Putting a plan together, having some pluses and minuses doing something. I mean, like, writing it down is a tool of thinking and any good project starts with that and usually gets managed through the written word. But here, well, I mean like when I think my method, it’s not that it’s that original, but my method starts from the realization that a document (and I use that as an analogy for anything creative, anything of value that starts with the document) But the document doesn’t start with a blank page. And I think we have this wrong idea that we how we decided to change our lives, start the new thing and come up with an ambitious project. And then the way we started, that is by looking at a blank page and then the blinking cursor. And then we will let the divine inspiration find this and inspire us to create greatness. I don’t think that’s actually what had happens. And I think the blank page is banal, at least the second step in a process. And that process of creative output starts where the inputs, it starts with what you read and you can access that through your notes. So I think the quality of your output will mirror the quality of your inputs. And that’s why I take consumption very, very seriously. A lot of the ideas that we put on paper, whether they are well constructed article like yours, or just, I don’t know, some scrappy notes are not collections of the vine ideas that have been bestowed upon you. They are usually other people’s ideas, stuff that you got from your parents, the society, the news, the whatever. So, you are working with other people’s ideas and to the extent that we can have anything creative to offer. What we offer is connecting other people’s ideas in a novel way. That’s what’s creativity.

Andra Zaharia: Yes, Layering a bit of our experiences on top as well.

Vladimir Oane: Exactly. But yeah, pretty much, I mean a creative, creative process it’s more about remixing all the ideas than I don’t know, having a Mozart experience where I know the Holy ghost comes upon you and you have the divine inspiration to create an amazing symphony. I mean, that’s not the creative process for almost anyone. So, we have to connect ideas, come up with our own flavors, but we’re working with some bricks. We’re working with something that we would… that we consume previously. And I think it’s very, very important to start there. Like, let’s make sure that I’m reading with purpose and that, what I’m absorbing it’s really absorbed. So, when I want to use this information at a later time, and when I look at that blank page, I don’t look at a blank page actually. I mean, like I just collect ideas, and connect them together in a way. And that’s the backbone of my project. And I know you do that when you write, because I’m pretty sure writing the document is usually the last step and the easiest step. The hardest steps is: what am I trying to say? What information do I work with? I have this concept and I have to introduce this fact and actually the order is backwards. So, whatever. You’re working with bricks in your head and then connecting what you’re doing by writing is just connecting the blocks together with some narrative content, let’s say. It’s the same for every other project. I know yours. Your output is something that gets published, then people come and read it. But it’s the same like when you want to start a new technology product, or you want to innovate something that you still have to bring your blocks together, connect them. The output may be different. Maybe you need to convince some people to join your team, or maybe you need to convince your boss to give you some extra budget. But it’s still like some creative output that you made out of everything that you have in your head.

Andra Zaharia: I think that you explained so well, kind of how you articulated this entire, let’s say structure. I don’t want to… I don’t know if you’d call it necessarily a framework, but just the way of looking at things and just your perspective and how you actually poured this into a product that others can use to do the same for their ideas, because one of the most pressing challenges that I’ve had throughout my years of actually making a living out of writing, which I only dreamt of in high school, but looking back, it actually turned into a thing and I had no idea I would end up here. One of my main challenges from all of this was to not only keep this knowledge and extract it and keep it in a way that’s organized because I need structure to function. And that’s just how it works but also find a way to activate it when I need it. And that’s been like one of my biggest challenges and that sometimes still is, because I take all these notes and I usually take them, like I write them down in a notebook simply because I enjoy writing. And that’s one of my main ways of learning and that applies to work. It applies to everything that I’ve done throughout my life and finding a way to organize that and to activate that can be extremely difficult. We can miss out on a lot of things. I mean, you read a good book and you tell yourself you’re going to read it again.
Because you really enjoyed it. And you want to dig deeper, but like 99.9% of time, you never do read that twice. And that’s not lost because some of it stays with you, but not enough to make a difference, not enough to nudge you in the direction that got you were really excited when you were reading like page 56 or whatever book you were reading. And to capture that moment that, that energy is essential to anything that we want to do. It can be a book, it can be a page, it can be a video, whatever it is, whatever it is that that drives us, we need more of that. We need more of that to keep us focused. So, tell me a bit about how people are using deep session, what kind of, what sort of feedback you got from them after they started kind of changing their habits around organizing knowledge for themselves?

Vladimir Oane: Well, yeah, I don’t think a lot of our users think of organizing knowledge and stuff like that, actually. That’s why I think our product is picking up traction… It is because we don’t see any of the things that we have been talking about for the past half hour. I mean, we’re not selling knowledge management and stuff like that, but we are synthetized and professional note taking service, if you will. So, we talked about how important note taking is and how actually not taking is the foundation of every creative project, whether it’s an article or anything that you might be focusing on at work. So note taking, I think is really, really important. But, note taking is hard. And you mentioned some of the ways in which it’s hard, for most people. It’s very hard to put into words what it is that they actually liked in a content. So, they may read a book or they may go to an article or whatever and say like “That was pretty cool.” And when you ask, like “What was the cool thing about it?” or “What it is that you like?” that’s usually a question that frustrates, a lot of people, because the emotional relationship it’s much easier to observe than to go to a rational. Like “What it is that I liked was that idea or that element” or like whatever. I just keep the feeling and not worry about the details, right? But let’s say you go over that and you actually think about it. Well, actually I like that idea or I like that example and I think it’s that thing that is the actual nugget. Then, the problem is you have to write it down and writing things down hard, like, oh yeah!
So, most people don’t write it down, but even if you write it down for a lot of people, the quality of their scribblings is… let’s just say low. So, if through some divine intervention, they find that note again. it’s very it’s unlikely that they will understand what it was about. And then there is a problem over our organization. Like I have these notes, like “Where do I put them? In what order? How should I organize them by white topic, by year or whatever?” So, we’re talking listening something or reading something and finding that thing cool. And you see how much willpower we have to deploy in order to make a small, simple note. So, to my experience, most people don’t do it. And the few people that do, do it badly. So Deepstash, kind of reverse engineers, the written text, let’s say so, our vision is to take an article that you wrote and to be able to postpone or to postpone, to go back in time. I don’t know when you were just creating your core ideas before you connected them and just access those blocks that actually made that piece, in the same way that, I don’t know, DJs or electronic music producers started to manipulate the audio files. Because I know before electronic music, you had the records, or you witnessed someone playing and you consume the music or the song or the album in bulk. You couldn’t break it down into its pieces. And of course, that’s quite hard, but with the new electronic devices and hardware that we have, it was easier to get. “I just need that sample. I need that vocal pattern and stuff like that. I want to create something else out of this.” And that’s how we got electronic music and hip hop and R&B, and like this explosion of creativity and those people are not inventing any symphony on their own. They are just taking things and creating something new and on their own. That’s very hard to do with a written text. It’s very hard to do a Kanye West on a book, you know, Kanye as being one of the most successful hip hop remixers. But we’re trying to do that with Deepstash. So we’re focusing on articles right now. So, for the articles that we present them in this novel format, as a list of ideas, which are like small cards with concepts that are summarized, they could be like definitions or they could be like processes, methodologies, quotes, anything that qualifies as a nugget of information that you would like to access at a later time. Most people just use it to consume larger quantity of information but I think our success has less to do with education. But I think we’re giving people a novel way to experience things that they already know because our product right now is very single-player mode. So, it’s read only, we haven’t added the functionality for people to contribute their own ideas, their own content. We’re going to do that, by the way, in the next releases. But for the time being, it was a consumption, focused product and people have disability in the product to save any ideas that they stumble upon that they like. And in most cases, those are the things that people already agreed with. The things that they kind of already knew deep down, but they were lacking the vocabulary to understand it. And they were lacking the vocabulary to present it in a way that it can become productive, you know, and with Deepstash, once you find something that you already kind of agreed or knew. But it’s a new discovery because you discover that fuzzy thing in your head, but in full resolution. It has like all the words and the right words and I can take this thing that I kind of believe already and I can use it to pitch my project, or I can use this as an argument in my fight with my spouse or whatever. And I mean, anything and knowing how to talk about something that you agree, I think is very, very powerful and people in our app just go to ideas when they find something, they save it. And we, our formats, our ideas have to help with all the issues that we have been discussing, with note-taking. I mean, our notes are professionally made only like we eat, we have a team of people who are asked to actually explain a certain concept or a certain idea as good as they can with the right words. They’re formatted properly. They add the minimum size, so you can consume them just by glancing at your screen. They’re easy to find because you can search them and we have all these ways to resurface them at the right time. And they’re putting in the right categories. You don’t have to worry about where to put them. Of course, you can customize it, but the false work for a lot of our users. So, it’s a new product category. It ties to some of the things that we have been discussing so far, whether, yeah, it’s a new way to consume information in a new way to take notes. We are early on… I mean, we have started our mobile products eight months ago or something like that. So, we are not an old product and we have a long way ahead of us, but yeah. I mean, our mission is to help people work with content and information in a way that would make that consumption productive. So, you feel like you’re getting something out of it, something that you can reference to, something that you can pinpoint to, something that can make whatever creative project that you have on hand, better in any way.

Andra Zaharia: And you basically underpin a very healthy habits and you breach this gap, exactly like you said it. You breach this gap between having the knowledge and actually putting it to work and actually doing something with it, which is something that we need a lot more of. I mean, curbing our conception would be very helpful and making more time to activate all that knowledge and those insights and those ideas, actually doing something with them can be incredibly empowering. The other side can have this paralysis effect than just lead us to endless consumption that turns into procrastination like we talked about earlier, right? They feel like this entire conversation has been just, you know, listening to, just getting a glimpse into your thoughts, into your way of seeing the world, is incredibly helpful. And it’s a deep learning experience that always kind of motivates me to go even further into start picking apart at these ideas and start using those building blocks to improve myself and hopefully things for others as well. So, I really appreciate you sharing all of this and doing it so honestly, because, as we both know, we’ve been around startups for so, so long, and you have even like such an incredible experience around them. This level of honesty is not the usual standard. It’s not the usual, the acceptance and self-acceptance of where you are and what you’re doing and who you’re doing it for. It takes a mature founder and a mature person. That’s spent a lot of time wrestling with these things to reach this level. So, thank you for making them part of this podcast.

Vladimir Oane: Thank you! I appreciate it.

Andra Zaharia: And before we wrap up, because we’re not talking about hacks and because we’re not talking about fraud counts, I wanted to ask you if you have a question that you’d like to leave kind of listeners with.

Vladimir Oane: A hard one. I mean, something that builds on when I think an hour and a half conversation is ask yourself: “What do you do?”, “What you do?” and I know it’s a big question. And if you take the question seriously, you will have to think about it for many days, weeks, months. It’s not an easy question to answer. And if you’re honest with yourself, you need to do a lot of like, kind of folding until you’re figuring out. “Why you’re doing what you’re doing?” So, yeah, that would probably be, I think it’s connected to our discussion.

Andra Zaharia: And it ties it in like we’ve gone full circle this conversation. Thank you again, Vladimir. This has been very insightful and very… it’s just made me even more curious to start working on some of these aspects myself more, and hopefully sharing these with others and, kind of supporting each other through all this. Very long journey that we have ahead of us.
Just like you do with all of your, not only your customer, your users and customers, but also with your team and with the rest of the community, because I know you do a lot of that as well! So, thank you again!

Vladimir Oane: Thank you for having me!