Mastering the Art of Failing
Mastering the Art of Failing Podcast
The $1M Deal and an Unexpected Mentor

The $1M Deal and an Unexpected Mentor

Season One, Episode Five: Entrepreneur and product visionary Ari Block shares his story about a million-dollar deal.

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You start a new job, walk in the door, and without much more than some onboarding, you’re tasked with securing a $1 million deal. That is precisely what Ari Block faced. No pressure, right?

This week on Mastering the Art of Failing, entrepreneur and product visionary Ari Block shares the story of his first job and how he almost jeopardized a million-dollar project on his first day. Fortunately, after a wayward path forward, Ari was part of an $80 million exit, an unexpected but crucial mentor, and where his leadership skills of today stem from.

Block discusses the importance of building relationships, overcoming biases, and learning from mistakes. He emphasizes the significance of understanding the human element in business and its impact on success.


  1. Building relationships and trust with others is crucial

  2. Overcoming egocentric bias and being self-aware can lead to growth

  3. Human connections and personal touch should not be underestimated, even in a transactional and productized world

  4. Learning from mistakes and understanding the barriers that prevent success can lead to better decision-making and learning processes

  5. Confirmation bias can hinder progress, and it's important to collect unbiased information and consider different perspectives

  6. Understanding customer needs and pain points is essential for product development and success

  7. Adapting and pivoting based on market demands and opportunities can lead to new and unexpected directions for a project or business

This week, Ari Block shares a captivating story of his first job experience, where he nearly jeopardized a million-dollar project on his first day. Despite the initial challenges, Block’s journey taught him valuable lessons about leadership, building relationships, overcoming biases, and learning from mistakes.

Building Relationships

Block’s story highlights the importance of building strong relationships in the workplace. Despite being a software developer, he was entrusted with a million-dollar project due to his ability to communicate effectively and work collaboratively. Investing time and effort in establishing connections with colleagues, clients, and stakeholders can lead to trust, support, and opportunities for growth.

Overcoming Biases

Block’s experience with egocentric bias serves as a reminder that our own biases can hinder our success. Recognizing and challenging our preconceived notions, we can better understand others' perspectives and make more informed decisions. Overcoming biases allows for a more inclusive and diverse work environment, fostering innovation and creativity.

Learning from Mistakes

Navigating through failures and learning from them is a crucial aspect of leadership. Block’s ability to reflect on his mistakes and seek improvement demonstrates the importance of a growth mindset. Embracing failures as learning opportunities and implementing changes based on those experiences can lead to personal and professional development.

Understanding the Human Element

Block’s story emphasizes the significance of understanding the human element in business. Building personal connections, showing empathy, and considering the needs and motivations of others can greatly impact team dynamics, collaboration, and overall success. A leader who values and respects the individuals within their organization fosters a positive and productive work environment.

Adaptability and Agile Decision-Making

Block’s ability to adapt to unexpected challenges, such as integration issues and the changing market landscape, showcases the importance of being agile and flexible as a leader. Being open to new ideas, embracing change, and making informed decisions in dynamic environments are crucial skills for effective leadership.

Show Transcript

Mastering Failing uses automated tools to create a transcript of our show. Please excuse any typos and hallucinations that we’ve come to love from our new AI overlords.

Ari Block: hello, my name is Ari Block. This is the story of how I almost fucked up a million dollar project on my first job on my first day in that job. And which ultimately did lead to exiting the company for 80 million, but with a lot of really interesting mistakes on the way.

Alex Love: Thank you so much, Ari, for joining us. We're really excited to dig in. So let's recap. You said first job ever

Ari Block: That's right.

Alex Love: walk in and the expectation is you take over a couple of million dollars worth. So how did we get there? What were your expectations walking into this role? What did you think you would be doing?

And how did you get to inheriting, such a massive portfolio day one job one?

Ari Block: Honestly, I can't explain it. I think the only reason I got that job, I was hired as a software developer and this project came along and I'm a South African. So I spoke perfect English and I was back then situated in Israel. And the other thing I was, young and ambitious and I had to work with Australia.

So they were like, there's this guy, he speaks perfect English and, he can wake up four o'clock in the morning to work with the Australians. So I think they just pawned it off to me. And this was almost 20 years ago. It was Australian dollars, so a little less than our currency at the time, the American dollars but still a lot of money, absolutely.

Alex Love: Yeah. Okay. So what initially ran through your mind, right? When you get handed this. You're coming in as a software engineer, right? Just because you speak the language. Essentially. How did you go about that? Like, where did you start? Were you like, alright, I'm excited. I'm gonna dig in. I'll figure it out.

Were you immediately I have no idea. I'm well over my head. I don't know what to do. Walk us through how you were feeling at the moment.

Ari Block: Oh, it was a mix of feelings. On the one hand, I was terrified. I remember myself on that first day, just sitting at my desk, the CEO walks into the room and he's, he, this is, he is a daunting fella, massive wide shoulders, one of those guys that go running at, four o'clock in the morning and munching on protein bars all day.

And he has this massive folder of 800 pages in his hand, which is the specification of this project thumps it onto my desk, right? Noisily. And he says to me, I want to plan to close this million dollar deal by tomorrow. I was anxious. Honestly, I was petrified. When you're that young and and if the milk's still on your lips, so to speak you say, yes, sir.

And you get to work, no matter what you're feeling at that time.

Alex Love: Yeah, no, I got that. So what did that plan look like the next day? How'd you put that together?

Ari Block: I worked my ass off. I did not sleep. There were a whole bunch of colored pieces of paper, and I marked everything up, and I did all the work, and I put together this Excel sheet about all the steps, and I identified all the risks, and I put together, the plan that I thought would be the best at that stage.

But what I did is I identified the biggest risk points in the project, which was this integration with the third party. And, as it turned out that, that turned out to be my biggest nightmare, this third party integrator.

Alex Love: All right. So let's dig into that. Cause that sounds like a pivot point. You got your plan, you're ready to go. They're like, yeah, sounds great. Let's talk about that integration point.

Ari Block: So basically I'm a couple of months into the project and I'm standing before the CEOs. door about to knock but frozen in place. And I, as I am retelling the story, I've got goosebumps. I'm I can almost feel that fear that I was feeling back then because I basically came to report to him my progress or lack thereof progress.

Because I was unable to get this project done. Everything was hinging on this integration with this third party. And at that stage, they were the enemy to me. They were the thing that was preventing my progress. And I felt like I was going to go in there and I was going to get fired. Because it's been a couple months.

And these million dollars are still in the air. I was quite honestly afraid at that stage,

Alex Love: And talk about their reaction or not. Your boss, you give this report, right? Obviously, great news. We've made no progress. I'm this new person. You trusted me with it. What was the feedback coming your way?

Ari Block: Look I was very young at the time. So I came into this fight or flight. I had an awesome arsenal of excuses of why these guys, right? Are the enemy, why they're stopping shit from moving forward. And I just dived into that, right? And I was expecting the worst, but he really. He was a mentor to me, and he showed me by asking, but first of all, by listening, and then by asking really good questions, he showed me that, a we're a team together and be he diffused my stress that I was quite, quite visibly in at that point.

And then at some stage, he said to me. Look, Ari, what you need to do is go visit the supplier in person. And I did not want to do that. They were the enemy and I was like, classical geek. And I was like, I'm using all this technology to communicate with them. Why do I need to go there? Makes absolutely no sense. And then

Alex Love: You don't want to take a trip to Australia? Okay.

Ari Block: in the Baltic triangle. This was Estonia. So it wasn't that wasn't too bad of a trip. It was a couple hours. But I was like, no, why do we need to do this? And he started to get a little annoyed and he said to me, Ari.

You're going on a paid vacation. This is exactly what he said. You're going on a paid vacation. You're going to wind them. You're going to dine them. And you're going to build a relationship. And you're not going to think too much about work. And I was like, nothing about work. This is the whole objective that I'm going for.

It blew my mind. But I said, yes, sir. And that's what I did.

Alex Love: Yeah, that's so interesting. And like, all of us aging ourselves, but I think a lot of us go into our first couple of jobs, not realizing how important relationship building is and that trust that you can build with people. And I had a similar experience at my 1st job, maybe not millions of dollars on the table.

But I actually got a really poor. Like Q1 performance review, because I didn't talk enough. Like my focus was like, I come to the office, I put my headphones on, I do my work and they were really, like you don't engage, you're not in part of the culture. We don't know you. We don't, you're not, talking.

And so I stepped back and did less work, which made no logical sense to me. Especially coming out of college where they're like, do all the things, the papers, the whatever. But that's a really hard, but important lesson I think to learn so early in your career is that people want to work with people.

And those relationships really do drive business.

Ari Block: That's right. And they're, off the topic, but we can come back to this later. There's a difference between competence and confidence. And as human beings, we often confuse the two. So I completely agree with that. But I, I said, yes, sir. And once you agree and commit, disagree and commit either way you commit.

So I went to Estonia and I learned a little bit of the language to break the ice. And, I wind them, I dine them, I built relationships. And, being the young, arrogant bastard that I was at the time, I came back and I was ready to prove to the CEO that was a waste of time, didn't work, and, you were wrong, basically, I was that bad.

But then magically, so it seemed the project was done in a couple of weeks. And that shocked me. Absolutely shocked me.

Alex Love: How has that influenced you maybe today? What have you pulled forward from that relationship building personal touch,

Ari Block: yeah, that's a great question. It actually started a lifelong journey of. learning and how to learn from mistakes and identifying The psychological biases or cognitive biases that learn to our mistakes in that process of both decision making and learning from our mistakes. So the kind of retrospective and, the CEO was the first person to put me on that track.

Cause I found myself standing again in front of his door paralyzed with this time, not fear, but confusion. And I'm about to knock and I'm asking myself how did I. Get this so wrong. How did I miss it? And what were the mistakes that led to, why didn't I figure this out on my own? And I knocked on the door, heard the come in.

And he pointed out to me that basically I suffered from what is called in the industry or in the psychology egocentric bias. And what I see, Elliot, you're very familiar egocentric bias is basically the inability to see beyond your own nose, right? And the way he explained it to me is we're all playing a game.

And this game sometimes has the same outcome or the same goals. In our case, we both had to deliver this project in order to get paid by the customer, but the rules might be different for each player. Now that shocked me. And in this case, the rules of the game were culture. And I failed to basically break bread.

I failed to, to establish a relationship to provide homage. And by flying over there, spending that money, being away from my family, buying dinner, all those things, they created a relationship. Then allowed us to move forward and the way they saw me before is who is this asshole who's coming and making these demands of us?

What is this? And came across as incredibly arrogant and I was incredibly arrogant at the time. And that's what came across and it completely destroyed the project. But as I said before, that was just the first step of understanding that there's all these barriers that in essence prevent us from doing well in our professional environment.

Alex Love: Yeah, that's so important to today, right? Because it's so easy to ignore the person who's emailing you or flacking you or texting you or what have you. Especially when you haven't connected with them, right? Like you don't, you haven't seen the name of the place and you don't know them or, ask about their kids or, what have you, right?

Just looking at business versus people

Ari Block: That's right. And maybe don't answer the email, pick up the phone and talk to the person, make a personal connection.

Alex Love: and introverts. We're a nightmare. I hate calling,

Ari Block: That,

Elliot Volkman: in a remote world now.

Alex Love: Absolutely.

Elliot Volkman: Yeah. And fortunately, back then we have offices with pop in visits and all that, but, so just jumping ahead, obviously we'll keep going on that journey, for those younger folks who are maybe working remote, who don't necessarily work in an office, how would you explain to them the value of building those relationships?

Obviously ecocentricity does apply to anyone just entering the workforce, just like as you were. But yeah. How do you break through that? Especially maybe if you are an introvert and prefer to be a hermit like myself.

Ari Block: Yeah, that's a great question. Working remotely has made it more difficult and There are no more pop ins. And in fact, in this remote environment, a pop in feels rude, right? And we also try to keep these meetings that we do have as short as possible. There's less of the small talk, right?

But building those relationships allows us to, to have trust with one another. And when shit hits the fan and you need somebody to be there. You're on site, you're deploying a project. It's maybe, 9 p. m. Everybody's gone home, but you need that support. Then unfortunately the difference between them being there for you or not might just be if they like you.

It might just be that they know what you're going through and you understand what they're going through. So that human connection is incredibly important.

Elliot Volkman: Yeah. And honestly, this is something that Alex and I have discussed in a couple of past episodes where that branding experience, it's, a team and connection, if you're trying to create a transactional relationship. It is going to die as soon as sign the contract, the agreement. But, if you want something to continue on, there is absolutely always going to be a human element, especially if we're getting into this space where there's now AI supposedly taking jobs, even though it's not doing that quite yet automation, all those other factors, there still absolutely has to be human components and you more than anyone.

You have a very product driven vision brain in your head. I, we don't go back. So far, but I've seen the stuff that you work on and we've worked in this world where there's now like these product led systems where they just expect people to give them a bunch of money and hope they stick around for years to come.

So I love a little bit of insight into your perspective how do you navigate around a world that is so transactional now and so productized where, they're neglecting the human element, which is absolutely critical to everything that we do.

Ari Block: It's a difficult question. I think the most important I think the most important way to look at it is to understand that there is a certain process, right? In everything that we do every day. And we basically collect information in order to make a decision. Then we form a plan. After we form that plan, we execute it.

And hopefully, many of us will try to learn from what happened. In that process, Those psychological barriers or biases are affecting us in every single step of the way. For example, we will make decisions based on who are the players. If we like them, if they like us, we might try to avoid people we don't like.

For example, if we're collecting information, then we might collect information or ignore information that doesn't support what we already believe. That's called confirmation bias. And what about information, collecting information from people we don't like, or maybe ignoring information we don't know that even exists, right?

That's called availability bias. So every step of the way, there are these social and psychological barriers that are preventing us from being successful in essence. And that happens also in the other stages that I mentioned downstream, also learning from your mistakes. And then the question is. In my opinion, how do you overcome those biases and, simply be aware of them, understand them, and then have tools to address them.

The first step is just understand the addiction example, right? Just understand and admit that you have a problem on your journey to self awareness. That's my biggest recommendation, right? Learn how to be more self aware in what you're doing and how you're doing it.

Build a process around it and improve your process. Because I think those processes are incredibly efficient in creating improvement over time.

Alex Love: So let's go back to your failure point. So we completed the project. It got done, right? Where did it end? What's your exit strategy? What else happened there?

Ari Block: Yeah so unfortunately this first mess up was only the first of many. We actually ended up fully deploying the project. We got the million dollars in our bank. We distributed these hardware units across the points of sale in Australia for for this big telco called Telstra.

And we had this reporting system in place. And I remember myself again at my desk, sorry just looking through this information coming from the reporting system. And I was sure the system which I built was broken. Because it was showing me nobody was using the hardware units in Australia.

So I was like, something is wrong here. And my first, gut thing is go and look at the software, go look for bugs, ad logs, et cetera. And I worked on it for a couple of weeks just to verify that the data I was getting wasn't fact true. Because I, I was, again, we talked about confirmation bias, I wanted to believe that there was a bug in my system because the other option that nobody was using our product was way worse.

So I was just suffering from confirmation bias all over again there

Alex Love: right? We want to think that our products are the best products. And we had that conversation on other podcasts. You don't do your customer discovery, but you could have to be in the world to you. But if no one ends up using it, Maybe it's not the best idea. So dig into that pain point, right?

You've got the data, there are no bugs. What happens next? How do you convince yourself?

Ari Block: Back to getting on a plane to this time to Australia of course, what you do as a product manager is discovery. So I went and I talked to about a dozen of these stores. I went into the stores. I talked to the people and I identified that there was no incentive for them to actually use the system.

They were so focused on selling new phones. They didn't want to help the customer copy their contacts and content from one phone to their new phone, unless they actually asked for it. Because it slowed down them in sales, which was, they're basically commission based. So of course I took this back to the internal team, to the customer team.

We worked around it and came up with a bunch of suggestions. None of them worked. So again we identified the problem. We tried to solve it. We didn't. What, what made it worse is that they wanted to renew and buy more units. So they knew, this is crazy, they knew it's not working, they knew it's not used, but it had this great marketing effect.

So in fact, we were successfully selling something that was to a certain degree practically not used. Wait, there's more.

I was always a geek, so I was very in tuned with this thing called Android, which back in the day was, was the thing that only geeks that dabbled in Linux knew what it was.

And my comment to the CEOs was there's something coming. Android and Apple cloud, these things are going to completely obsolete our product. So not only are our customers not using our stuff we are going to be completely obsoleted within two years. So I was bringing to the team this gloom and doom of everything's going to fall apart.

Which now we know in retrospect is true, but back in the day, this was outrageous. And I had to present that information to the team.

Alex Love: How was that received?

Ari Block: Much like before, I was much more afraid and anxious than It was much more difficult in my mind than it was in reality. And once more, the executive team actually listened and did their research. It was a hard pull to sw, to swallow. The solution actually came from the lead salesperson in the United States.

His name was Adi and he had this idea of basically pivoting the cost the company from focusing on. This idea of we're helping people manage their content on their phones to actually extracting information from phones for the purpose of police and federal agencies. And the whole concept there was that if you extract information at the point of arrest, there's no chain of custody.

So it makes the whole process much more easier. And in fact, we pivoted our devices to create legal evidence. One of the famous stories that I told everybody I was hiring because I thought the company was inspirational at that point is that we were able to collect a video of a 13 seconds where this felon criminal molested a six year old girl and took a video of himself.

But deleted that video. Our hardware was able to basically reconstruct the video. Cause I don't know if you know this, but when you delete it, really, what you do is you're deleting the name of the video. You're not deleting the content of the video. So we were able to de encrypt it, reverse engineer the information and on the spot provide evidence that put that person in jail for many years.

So that, that whole pivot was basically because we identified. And acknowledged that we had a problem based on the information we collected from those reports originally.

Elliot Volkman: I'm curious if I can jump in here. That is a significant pivot. You're going from a consumerized solution that basically, in theory would have added value to phone sales persons to, a critical asset for law enforcement and legal purposes. What do you think would have occurred if there was that ego mentality and stubbornness?

A lot of people would not be as fortunate, obviously, again I'm, I know you, you are a trustworthy person. You come to the table with facts and information that have, a result of convincing story, but not everyone presents as well. What would happen if that happened? Would y'all just dig down to the grave?

Yeah. What would, what do you feel would have occurred in a situation like that?

Ari Block: It's not all me, it's, I would say it's a, I'm a small part of it. And in fact, I personally have been part of teams where we have made exactly that mistake. And what happened, what was fortuitous in this situation is that we identified an issue early and that bought us time. That bought us two years before the market forces became a reality.

And the technical CEO, he had this thing, which he called developing it, developing into the draw or writing to the draw like poets do. And you write this thing or develop this thing and you don't put it out of the draw until it really becomes important. But that bought us two years to think about the marketing, to think about the R& D, to develop a product and not spend too much money on it.

So when we really needed it, we could pull it out. So in fact, what I describe in two minutes, really rolled out over two years. But because we weren't arrogant to say, no, that's not going to happen. We were able to put a long term plan in place. Unfortunately, I've also been part of teams who have said that's not going to happen, completely ignored it and didn't put any kind of controls in place.

And at the end of the day, it's not a single person. It's also about the team's ability to work together and how the team makes decisions and learns from their mistakes. And too often do we see this, people who are incredibly articulate. Or incredibly technical using their skills in technical ability or articulation to hide mistakes, to augment the reality, to basically make poor decisions.

Alex Love: yeah, just pulling on that concept of teams, right? From your experience and sort of the different teams that you've operated from, what are some of the indicators that you see that, this is a really strong team that we have the ability to move the needle, make the right decisions versus some of those instances where you're like, this team is going to crumble.

There's too many egos, we're not going to really get anywhere.

Ari Block: the positive indicators is the ability to listen. If you say something and. The answer is no, and there's no follow up questions to dig in. That's a bad sign. If your executive team is listening, asking questions, doing follow ups, great sign. If there is a process for decision making, that's a great sign.

If you're thinking about how to make decisions, great sign. If there's pre mortem and post mortem activities. Great sign. I would say premortem activities are the least common and probably something most people don't even know about. That's a great sign. It's an activity that comes from the risk management world.

So I would say the positive and negative signs are the same, right? It's the, if you do something or you don't do something, and it's mainly around how decisions are made. And how you learn from mistakes. I would say that, the topic of the podcast is just incredibly important to any business around the world.

Alex Love: Yeah, seems like the key themes are clear communication and planning, right?

Ari Block: That's right. That's right. And, going back to the biases is also understanding how those processes of communication, gathering information and planning can go wrong is really key aspect of it. Because I think a lot of people know you have to do something. But if you are doing it poorly, then that isn't a lot better than not doing it at all.

And we have the sense of, the sense of false achievement because, oh, we did that, but we didn't really achieve what we should have achieved through that process. Is our process good enough?

Elliot Volkman: Yeah, plus there's the peer factor. Sometimes you're not communicating effectively to the point. You might be grinding all day, but if no one knows what you're doing because you're just so busy getting things done. You're not moving anywhere. It relates back to what Alex was talking about.

She is just busting her ass, keeping her head down, you spend more time chatting with people and Oh, all of a sudden you're you're running up the chain because people are aware that you exist.

Ari Block: That's

Alex Love: I attended 12 meetings. I checked everything off my list, right? I must have done a good day's work, but it doesn't work that

Ari Block: right. I had one of my employee's name was David and he never talked at meetings. And in fact, we had four or five people on the call and only consistently three of them were talking. And this was pointed to, somebody else pointed this out to me, and I was like, okay, what can I do? So I made a point to give time in the meeting to ask David and the other team members, are we missing something?

Is there information I talked, I may have mentioned availability bias or attentional bias, right? These are the things that, that we're not even thinking about. It's information that we don't know that exists. And I asked him this question and consistently, every time I asked the question, he gave this incredible insight that was incredibly valuable.

And all I had to do is just give him that space to communicate. And then, of course, when you make a mistake once, then you're asking yourself, what other mistakes are you making? And that's starts you on a path to additional growth.

Alex Love: Yeah, that's such a typical facilitator trick as a former consultant, right? Especially in the virtual space, where it's so easy to turn your camera off and hide, right? We have a lot of people who, if you're really not truly going to contribute to the conversation, why are you on the meeting?

I'm sure you have other things that you could be doing. But yeah, people don't always consider that every form of communication or meeting doesn't work for every personality type, right? There are plenty of very quiet people who have great ideas. But don't have the personality to stand up and say, here's what I think, right?

Not all of us are type A. So that's great that you make that time or acknowledge, good ideas come from anywhere in the company. And just because you didn't push it doesn't mean that you don't have something to say.

Ari Block: Yeah, Elliot had a great point before about, communicating well, the problem is that if you're a great communicator, you can win a negotiation or argument or in essence quiet somebody who may have a really important point. So the other point is not to abuse your negotiation skills in an environment where really you should be listening and trying to understand somebody's point of view, because even though you don't understand it, you.

Could be missing something incredibly important that will help you succeed. And that's the flip side of being a great communicator. It can also harm you.

Alex Love: Yeah, good point. And leader too, right? Titles. Sometimes titles get in the way, right? I just spoke on a panel. About cultures of experimentation. And, I would hate for my, I would be failing as a leader of my team. If people thought just because I said something, it was a good idea. And so I go out of my way to say, this is probably bunkers.

What do you guys think? Putting yourself out there that, just because I have XYZ title or I sit somewhere on the org chart doesn't mean I have my shit together and it doesn't mean it's a good idea. So please contribute to the conversation.

Ari Block: that's true. It's tricky because on the one hand we want to be confident because if we're not confident, then people think we're not competent. But on the other hand, we want people to feel comfortable. To speak up, to power, right? So if you have that VP title, people may assume that you're right.

But what that does, it quiets voices, right? And that's not a good thing. What I've found is being humble, human, and specifically admitting to mistakes. In a structured manner. One thing that I do, which I think is an incredibly important tool is a decision journaling. And we can talk more about this, but basically it means that you journal what your decision was, what were the assumptions that you had, the data that you had pros and cons and the decision that you actually made.

If you take that into a team activity and basically say, this is the decision I need to make. These are the pros and cons. Then people then become, you become more human. And if you make a mistake, now you're using your journal to come and say here, this is why we made this decision. This is the piece of information that we had.

Or did not have, and this is why we made the decision. And now you're not talking, now you're not talking about blaming a certain person, but you're talking about how do we have a better process moving forward in order to improve on our decision making capabilities. And that kind of moves it away because every time you come into a post mortem as opposed to a pre mortem, everybody's afraid of blame.

And moving away from blame, that really enables a more healthy culture that enables people to speak up. Because they're not afraid that they're, they're going to be, shooting themselves in the leg or whatnot.

Elliot Volkman: I love absolutely every bit of that. What you're talking about is really the split difference between a leader mindset and a manager or authoritative mindset. It's. Being able to be in a position where creating transparency and trust, having vulnerable conversations and theory, just like this series is designed to do and showing that you're a human behind, your confidence, but, too much confidence leads to that ego mentality.

You shut people out, you shut people down, people will show up to meetings, they will remain quiet, they will take that baggage, and it will carry on to other careers and other positions, and it just does a disservice to you and everyone else. At the end of the day, you need to embrace a culture of diverse opinions, and I think that's like the middle ground of everything that I'm hearing here.

Ari Block: That's absolutely true. I think everybody knows that, but executing and having the tools and techniques to do that is incredibly difficult. And that's why I like to talk about processes and break it down and, recommend books explaining the psychological biases, like Thinking Fast and Slow by Daniel Traversky and Nudge by Richard Taylor.

And if you really Think about your process then you can make a difference. Just telling people, Hey, be better, be inclusive. That's hard because people are not inclusive for psychological reasons, which are built into them. So thousands of years ago, whatever, when we were running away from tigers, our, our brain one, or our brain that basically forces us to think in shortcuts, it had value.

And even today it has value. But not in all situations do we want to think fast. Sometimes we want to think slow. So being able to do that and knowing when to think fast, when to think slow, to have processes to allow you to do both because sometimes you need to think fast. Absolutely. You need to take these shortcuts that allow you to make decisions fast without having all the information, right?

That's also important in certain situations. Having all of this available to you. Is an incredibly powerful tool for everyone, not just managers think about individual contributors, even software developers, they make incredibly important decisions and they're doing the same thing. They're gathering information, they're making predictions, putting out a plan, they're taking action, and then they're learning from their mistakes.

Same as everyone.

Alex Love: Yeah. That's an awesome book for sure. Any other resources or books that you'd like to share with the audience, we'd love to put those out there that have helped influence how you think of things and train others to think about this process mindset.

Ari Block: Yeah I have a long list. I can, we can probably attach that to the I love Audiobowl maybe you can allow, attach a list to the to the podcast and share that with the community. Absolutely.

Elliot Volkman: Yeah, we can absolutely make a little addendum of Ari's book list and make it the winter reading list.

Ari Block: There you go.

Elliot Volkman: But yeah, I don't know of all the conversations that I've had with you. It sounds like psychology is such a critical element in your approach to how you just function through everything.

Obviously our relationships been business oriented, but, You've always come to the table with some big ass and bold ideas, but it always tends to work out because you think things through you bring proof and evidence. I just absolutely love and appreciate your perspective on how this all functions.

If, and I'm just gonna throw this out there, but if anyone has. The time I would absolutely reach out to Ari to pick his brain. He is an operational leader to the degree that any organization would need. Yeah, it just reminds me of this conversation that we just had with Glenn Hellman on how he coaches organizations.

I see that in your future roadmap, you are the CEO of like 30 different companies somehow because if anyone could do it, it's you

Ari Block: That's a, that's an exaggeration, but I

Elliot Volkman: know, it's totally real. Haha,

Alex Love: close out your story, right? So we talked about a couple of, Pivot points, completely changing sort of the orientation of the product, right? To help law enforcement, where does that story end for you? How long were you at the company? What was your exit strategy?

What did you do next?

Ari Block: Yeah. Yeah. What happened is over a period of two years, we built out that product and the company was sold to a Japanese investment company for 80 million. And until today, I remember the smile on, the CEO's face when he, that check cleared basically, and he got his equity value in the bank.

So in this case, Grateful Yet a wonderful exit, right? And wonderful ending of the story. But that's not always the case. I've been in environments unfortunately where I had to fire a whole team of people and the companies just ran out of cash. Any successful entrepreneur tells you about their successes.

But the truth of the matter is that more than half of their experiences failed. They just don't talk about it.

Alex Love: Yeah that's why this podcast exists, right? Break down the layers and the onions. So looking back at that whole, two years, first sort of job, what kind of core elements and lessons did you pull from that? That's really guide. How you manage and lead today.

Ari Block: First of all my, I wasn't, I was still am, but learned to overcome it, a huge introvert. I know Elliot is, Elliot's face is saying you're an introvert. No, but the truth of the matter.

Elliot Volkman: you all are killing me. That's so wrong.

Ari Block: But if you, okay, let me describe me to, to you 20 something years ago wearing a a t shirt with Dungeons and Dragons picture because I was a dungeon master in my day. Wearing sweatpants cause like, why would you dress any other way than what's convenient to you? And not necessarily making eye contact to the person talking to you.

Huge introvert, like going on a stage and talking scared the shit out of me, even doing what we're doing today, that would, be a reason for panic and to me in my world, logic just ruled what was emotion. Like it had no place and even today I make that sin right where sometimes I lean more on logic than emotion and, making that distinction on when you need to listen, give support, when you need to analyze and give a solution.

I'm steering into the area of relationships and my wife it's, that's not an easy task. And for me, having that feedback from others. And there was this one day I remember so clearly I had the same feedback coming from three different people which were not overlapping. These people had did not know each other, but they were all telling me, Ari, you're not listening enough, right? And that was this huge shock, was how is it possible that three different people that don't know me are all giving me the same feedback. They can't all be wrong, right? But at that stage, I was arrogant enough to think that if one person is giving me feedback, they must be wrong, I must be right. But when three people did it, I was like, maybe I need to think about myself differently.

And, that started a journey of self awareness. So I think that every person's journey is different, but perhaps this podcast can put them in On that track to taking the first step and we talked about tools like decision journaling and like a pre mortem and just being aware of the cognitive biases.

I think these are the kind of tools that at least help me take that journey and extra step. This is something that's been happening over 20 years. It's not a, it's not a, a quick fix. Coordinate your expectations, be kind to yourself.

Elliot Volkman: Yeah, regardless of what people say, you're not always born later. Sometimes you just age into it. I you, I did not have a D and D shirt. Although during that was very much thing. Yeah I was absolutely fearful of any of that. In fact, during our nonprofit days and we had events every month or multiple times a month, Alex literally did all the talking.

I had to get a lot of liquid courage just to get up there. But I don't know, maybe once you just get old you stop giving a shit and stop caring what people think. And that's when you grow out of it. But yeah, I think that's absolutely critical. So if you're listening and you're young and you're trying to build something cool.

Don't be afraid of talking. Just get your idea out there. Get it beaten around. That's the best way to get some feedback. Anyways.

Ari Block: That's right. It's okay. It's okay to practice. I'll have, I'll confess that before getting on this podcast, I practiced I did an inventory of my 15, fuck ups right over life, how things went wrong for each one of these inventories. I didn't do it for all 15, but for five of them, I wrote a three page story of everything that happened and I did that analysis.

And of course, I have my, my, my decision journal right over here. So being able to really practice. Is a huge element in doing a good job. It's you're not born great. You can work your ass off to it. And what's beautiful is that nobody knows the difference between genius and hard work. They always assume genius.

So if you do a good job because you've practiced your ass off and worked incredibly hard, people will just assume that you're great. That isn't necessarily true. So my word of encouragement to everybody is that hard work, practice, studying, and learning can lead you to success, which shouldn't be a huge surprise.

But when we look at people and say, Oh, that's Elon Musk. He's a genius, right? That's why he's successful. I'm ignore. The fact that, anybody can work hard and be successful.

Elliot Volkman: I love that aspect because that, that is one of those elements of why we're actually creating this series. Is that overnight success is not really a thing, maybe, with parental funding, a couple of million dollars to make a business start out of nowhere. But, an athlete doesn't just become a, a gold medalist.

An entrepreneur, how many serial entrepreneurs are out there? What are those serial? Businesses, they probably were failures until they are where they are now. Maybe they had successful exits, but it's uncommon to be able to have that vulnerable perspective that is so critical to have out in the open.

You rarely just get to have that piece of the puzzle.

Ari Block: That's right. The saying that I love most is that it took me 10 years to become an overnight success. Sure.

Alex Love: I've really enjoyed this conversation. This is a lot of what my consulting career was built on was all of these biases. So it's nice to have that nerdy conversation with someone else who, who can name it and understand it. But any final words of wisdom or nuggets that you'd like to throw out into the universe?

Ari Block: I'll give you one. This is you can totally cut this in editing, but it's the inspiration that I share with my team and it's a poem actually. If you know the giving tree, then it's the same author and it goes like this. I'll swing by my ankles, she'll cling to your knees, as you hang by your nose from a high up trapeze.

Just one thing, please, as you float through the breeze. Don't sneeze. So my, my, my recommendation to everybody is don't sneeze. But the big takeaway here is that you're, it's a lot of luck. You're on the edge of success and don't attribute all your just because the outcome was positive. It doesn't mean all your decisions was positive.

And just because you were successful. It doesn't mean that everything that you did was the reason for the success. It's a team, right? Everybody's working together.

Alex Love: Yeah. Amazing. Thank you so much. This was our first conversation and I'm sure that it will not be our last. I'm really looking forward to your audible list. Cause I have a, I have to add to my emotional support shelf of books I have not read yet. Because you can never learn too much.

So really looking forward to that. But again, Ari, thank you so much for your time today. Great conversation and looking forward to continuing.

Ari Block: Absolutely. Thank you so much, Elliot and Alex. I was honored to be on your show. I appreciate it.

Elliot Volkman: Yeah, no, thank you so much for being part of our pilot and kicking this off in the best way possible. And for our listeners, stay tuned. We will be back with some other. I don't know who we're going to bring up next. I feel like we've got something pretty cool for you. Yeah. Failingpod. com, our subscription on Substack, Apple, Spotify.

Find us. We'll keep delivering. See you next time.

Mastering the Art of Failing
Mastering the Art of Failing Podcast
Join your hosts, Alex Love and Elliot Volkman, as we dismantle the stigma surrounding failure and empower you to transform these challenges into opportunities on your own journey forward.