Jorge: 0:00

It's not just enough to have chutzpah. It's also the,"You know what? I'm gonna go and knock, even though it's the middle of the night, I'm gonna go to that neighborhood and I'm gonna knock on the doors."

Narrator: 0:14

You're listening to Traction Heroes. Digging In to Get Results with Harry Max and Jorge Arango.

Jorge: 0:24

Hey, Harry. It's good to see you again.

Harry: 0:26

Oh man. Thanks for, thanks for breaking up my day with something fun and something I'm gonna learn from, I'm sure.

Jorge: 0:34

This is an audio only show, so folks can't see us. But, right before we joined, I was saying that I was very surprised when your video image popped up and you're wearing a t-shirt that I also own. Like, I own the exact t-shirt. I feel like you and I are so aligned in so many things, it's funny.

Harry: 0:52

That is funny, although I guarantee you mine is larger than yours.

Jorge: 0:55

Probably a little bit. But anyway, I'm excited about this conversation and as usual, I've brought a reading. And this reading is a little bit different from others that we've done in the past, in part because I think I need to set the stage before I start reading this.

Harry: 1:18

Oh, interesting.

Jorge: 1:18

At least a little bit. And also because I think that even if you haven't read the book, you're probably gonna know who it's by before I'm done with it. So maybe there's not gonna be as much suspense in this one as we've had in other ones. I'll say also, right before we get into it, that this is a book that I'm reading right now and I haven't finished reading it yet. I've definitely read the part that I'm gonna read now, and as I was reading it, I was like,"Oh my God, I love this, and I'm gonna bring it to Harry even though I'm not done with this book." And by the way, I'm loving the book, so I can wholeheartedly recommend it when we get to which book it is.

Harry: 2:08

I can't wait.

Jorge: 2:09

So this book is a memoir by a filmmaker. The part of the book that I'm going to read, they're discussing the production of one particular movie.

Harry: 2:25

Okay.

Jorge: 2:27

Alright, so here we go."If you look at the film from the point of view of today's"production values," then, I contend that no one would touch the project for anything less than$50 million. The filming was done on three barely accessible Amazon tributaries, and the main actor was the maniacal wild man, Klaus Kinsky. We were constantly in financial straits, and the cashflow from Germany was not functioning. Transfers often took weeks to arrive. One night, when we were really up against it, Lucki went to Miraflores, the affluent suburb of Lima, and went from house to house offering a deal. Because practically everyone there had a dollar account in the States to keep money hidden from the Peruvian tax authorities, they were interested in getting outside money directly funneled into the United States. Lucki said he needed$50,000 worth of Peruvian Soles right away. In return, he would have that sum wired from Germany to the United States with an extra 10% on top as a reward for so much trust. The sum would arrive within 48 hours. People in Lima had read about my project in the newspapers, but who was going to sign up for it in the middle of the night in response to someone knocking on the doors? Lucki, though, had a natural gift for creating trust, which he knew better than to abuse. A very young entrepreneur, Joe Koechlin von Stein, took him up on the offer. He needed dollars because he was planning a rock concert with Carlos Santana. With no more guarantee than a handshake. He handed Lucki the Soles the next day, and the project was saved for the time being."

Harry: 4:39

Man, that sounds like what happened next? I haven't read this and I'm super curious to hear what it is. I don't know.

Jorge: 4:53

I guess a little bit of context I left out is, he started by saying that today this a project like this would be$50 million. I think they had a budget of like tens of thousands. So it was very little money. This was in the early 1970s. The director is Werner Herzog.

Harry: 5:12

Okay.

Jorge: 5:12

And this was while they were shooting. The movie Aguirre, the Wrath of God, And I'll say the book, this is from Herzog's memoir, which is called Every Man For Himself and God Against All, which is a great title, right? And before we discuss it, I'll say, I'm really enjoying this book. I'm listening to it as an audio book, and if you've ever heard Werner Herzog speak, so he has a very famous voice. He's done documentaries, which he narrates. Anyway, I highly recommend this book, it's just a hoot. But I wanted to bring this passage in particular because I thought it a wonderful illustration of know if to call it an attribute, but a characteristic of people that I think is perhaps underappreciated. And it's certainly something that I underrate in myself and don't take opportunity to develop. And it's gumption.

Harry: 6:29

Ah.

Jorge: 6:30

By the way, the Lucki that they talk about is Herzog's brother or half brother, who was assisting him with the financing of the movie. And this notion that they are in this crisis situation where they've run out of money, and this dude has the idea to go around in the middle of the night into a rich neighborhood and start knocking on doors to try to secure financing for the film, and he actually does it, to me is just astonishing. And it's the sort of story that I associate with gumption. And when I read that, I was like,"Oh my gosh, there are times in my life where just going for it, going for some kind of like crazy long shot thing with boldness has paid off." And I wanted to talk about gumption with you because it feels like something that would help people gain traction.

Harry: 7:39

Oh, I love that. And there were two things that came to mind immediately. The first was, I never was a big Jerry Seinfeld fan. I didn't watch his shows, but I have to say in my top favorite movies of all time is a documentary that he put together on the creative process. We might have talked about this at some point. And the movie is called The Comedian, and it's how he returned from his show back to standup comedy. And it is an object lesson in gumption. But I didn't really have the word for that before, and I think to my second point, I think the reason I didn't have a word for it is, I didn't actually know what it meant. Because I grew up in a culture where the word chutzpah was the primary word that can tried to convey that kind of energy. But even though they're probably relatively synonymous with one another, I don't know if that made sense, but the chutzpah somehow seems more base and more ridiculous. So I'm curious what you think, if there's a difference between gumption and which leads you down the Forest Gump trail to the chutzpah perspective. I.

Jorge: 9:03

Again, folks can't see this. I'm smiling because this is yet another synchrony. So, when I was thinking through this subject and bringing this subject to our conversation, I had a little chat with ChatGPT about gumption. And I asked ChatGPT about the relationship between gumption and chutzpah.

Harry: 9:24

Okay.

Jorge: 9:25

Because that word also came to my mind. I was like, why gumption? Gumption, first of all, feels like an old-timey word, right? Like, it's not a word that is in common use. And it felt to me like, it's not exactly chutzpah, but I've used chutzpah more. And I wouldn't say that it's that chutzpah is more base, and this is something that ChatGPT helped me arrive at, is that gumption is somehow like the combination of initiative and chutzpah. It's not just enough to have chutzpah. It's also the,"You know what? I'm gonna go and knock, even though it's the middle of the night, I'm gonna go to that neighborhood and I'm gonna knock on the doors."

Harry: 10:13

It's chutzpah with a plan!

Jorge: 10:15

It's chutzpah with a plan, but it's chutzpah also with the actually doing it right? Like, the actually getting out there and knocking on the doors. We can have all sorts of brave thoughts, right?"I could do this, or I could do that." But it's something quite different to actually get in the car or whatever and start knocking on doors. And I think that's the missing ingredient. Like you can talk a big game, but going out there and doing it is something else.

Harry: 10:51

Okay. And now it's my turn to smile, which of course you all can't see, and the reason for that is I have a chutzpah story, but I think it's actually a gumption story. I'm going to be a little hyperbolic about this, but the gist of it's roughly true. Back in the year 2000, right? The heady year 2000, with all of what was going on in Silicon Valley, and the rise of the next great internet opportunity, which of course burst a few years later, but we're not gonna go down that path. And I came up with this idea. And this was the idea for my company, which I called Public Mind. That was the name of the company. And it really was a derivative of the company that I was a co-founder in called Virtual Vineyards, which became wine.com. And in wine.com, we were really the very first people to have a secure, usable, and very simple shopping cart, which I am extremely proud to say I designed. And I didn't build it, the whole thing, but I largely put it all together myself with the help of my illustrious co-founder Robert Olson, who built the backend. And we put out there, we launched live in January 1995. And from that point forward, we were selling wine online, and then eventually specialty food. And what would happen is, I would get these emails and phone calls and people would ask for things we didn't have. And at some point, I realized that's a demand signal. So I started keeping file cards of these things people wanted, and I kept the contact information for the people that were requesting these things. And so I had a whole table full of what I would call request groups. And the request groups went from,"Here's things I want," and then somebody would say,"Hey, I want that too," to eventually questions and complaints and suggestions. And so, I had these four categories of things all over these tables. And when I got enough of them, I would eventually work on solving them. Or especially, in the case of like sulfites-free wine, right? So a lot of people are allergic to sulfites in wine. And so, we were getting a lot of requests for wine without sulfates. And when we finally hit, I don't know, 25 of them, I put together an email list and I sent it off to folks and said,"Hey, I'm gonna see if I can work with the other co-founder Peter Granoff, who was the cork dork," he was the guy that sourced all the wines and worked with all the wineries to procure the sulfites-free wine"if we can get it, are you willing to prepay to get ahold of this?" And so, this was turning a request group that was manually managed into an action group. And remember, this is 1995–96, right? That's a long time ago. And, and at some point, so a few years later, I left that startup, which was my first startup, and I joined Hewlett Packard in an internal consulting group there. And it dawned on me that this notion of managing request groups based on demand aggregation was a thing, and it was gonna become key in the online interaction models that people were to would see. And this was like 1999, I think maybe late'98, I don't remember. But, so I came up with this model for building out request groups, action groups. And I designed the system, and Hewlett Packard was incredibly kind and gave me the time off to go work on it without declaring ownership over any of the intellectual property rights, and this is where the chutzpah story comes in. So here it is, like early 2000, and I'm thinking to myself,"Self, I have my time off from HP, but I don't really have any money to go build this thing." And so, I started reaching into my network, and I didn't know the first thing about being a startup founder, right? I'd been on a founding team, but I was the guy behind the scenes designing and building the website. I was not the guy that was on the front lines dealing with investors, legal, board all that great stuff. And so I started calling all my friends and people at Apple that I knew'cause I'd worked there, and people at HP'cause I'd worked there, and other companies and so on and so forth. And eventually found a guy that had sold his company to Apple and he was a good friend of a friend of mine, and he said that he had money to invest. And I was like,"Yes!" I'm gonna withhold his name'cause just out of, protect the innocent and all that good stuff. And so we met at University Coffee on University Avenue in Palo Alto, which I don't even think is still there. It was a beautiful, big coffee shop. I had a 400 square-foot office for$219 a month. Think of that, in Palo Alto on University Ave. It was amazing. At any rate, so I met with this guy. He agreed to meet with me. And I thought of this idea public mind as this world-changing idea to demand aggregation, right? You could join a request group, a private request group, and you could engage the world to get something made or get something procured, and the more people that would join the group, the less the price could ostensibly be, because I could then start discounting. And so I had this beautiful idea for this thing, I told people that demand aggregation, this idea that you could get people into request groups, was gonna be the future of the internet. And I was very secretive about this idea. Because in effect, it was a voting system, right? And people weren't doing that yet on online, not in a way where outcomes could be generated from the up votes. And, and so this investor sat down at University Coffee. I got my double espresso. And he goes,"So tell me your idea." And I said,"I can't." He goes,"What do you mean, you can't?" And I said,"I think it's a world-changing idea. And if I tell you the idea and you don't invest, then I'm out my idea," right?"You're gonna go tell people, they're gonna go build it, and I'm gonna be sitting here with a spoon in my hand and very sad." And so, he got really upset. His face turned all red, and he said,"Are you telling me I drove all the way down here from South San Francisco or wherever it was, and you're not even gonna tell me what the idea is? And I have a checkbook with me, and I'm willing to help fund your company. This is insane. Are you mad?" And I said,"No, I'm not mad. I'm just scared." I said,"Look, here's the deal. I need$100k to get this off the ground." And he goes,"I'm not gonna write you that check." And I said,"Write me half that check." I said,"Write a check for$50k, and if you really like the idea, you can write the other check." And he goes,"That's absolutely absurd, but I'll do it." And so he wrote a check out for$50k and he handed it to me and I told him the idea. And he goes,"That's a great idea." And he wrote the second check. And that's my chutzpah story. That's how we got that company off the ground.

Jorge: 18:08

Oh, that's great. Nowadays there are NDAs, right? But it might have been too short notice to fire up an NDA, but...

Harry: 18:16

I didn't know enough about it to know how durable an NDA was, and I didn't have any money to pay an attorney, and so on and so forth. I mean, sure.

Jorge: 18:24

But I think that with that story, you've hit on what I think of as another, aspect of gumption, which is the ability to think on your feet, right? To make lemonade with the lemons that you have, right? And that's a part of this as well. In the spirit of what we're trying to do with this podcast, which is to help folks gain more traction, I think that the question that I'm struggling with, and one of the things that I was hoping to discuss with you here, is whether you think that these I'm gonna call'em traits, the ability to do what you described, what you did, the ability to do what Lucki did, is that something that people are born with or is it something that we can develop?

Harry: 19:27

A fair and very important question. And certainly, if I were trying to answer that question,'cause I have my own beliefs and I'll answer that in a minute, but if I were trying to answer that question in an operational way, in a way that I felt was defensible, I would turn to Rich Diviney's work on the attributes. And Rich, he used to be in charge of training for the Navy Seals and individual assessments and team composition. And he has a book out that describes these characteristics and attributes that really help you better understand yourself, and he has a very strong perspective on this. I highly recommend the book. He has a very inexpensive assessment, which I have taken, which really pissed me off when I had to read it,'cause it told me something about myself I didn't wanna read, I didn't like, but I knew it was true. And it kinda set me back a little bit in terms of my confidence, but since then I've done a lot of thinking about it and I think it was the net-net was quite valuable. I wanna say that a lot of this can be learned, but I'm not sure you can just go learn it like a new skill. I think there are certain aspects of it, which you have propensities toward these things. And then I think your life's experience either reinforces those propensities or diminishes them. And I think in the case of this thinking on your feet, I think for Diviney's work, he calls that adaptability. And literally a week or two ago, he had a LinkedIn questionnaire about whether adaptability was something you could learn. And I don't recall what the answer was, because I would like to think that the propensity is not something you can learn. You kinda come out the chute with that propensity or not. But I think you can have experiences which support that and ultimately allow you to get better and better at it. Kind of real-life simulations, if you will. Or the opposite, and things that cause you to be more internally reflective and cautious, risk-averse, so on and so forth.

Jorge: 21:49

My sense is that there is an aspect to this that might be innate in the sense that you have to have a certain personality type to be bold like that. I don't think everyone is. But on the other hand, that might be wrong. Somebody might be so convinced about their project or the thing that they're working on that they just plow ahead. Diviney has come up before in our conversations, you pointed me to his book, Masters of Uncertainty.

Harry: 22:22

That's right.

Jorge: 22:23

Is that the book you were thinking of?

Harry: 22:25

Oh, no. Masters of Uncertainty is his second book. The Attributes was his first book.

Jorge: 22:30

And the reason I'm circling back to Diviney is that when I was thinking about this question about,"Can we develop gumption?" and thinking,"I don't know, because it does feel at least some of it might be tied to your personality," but I think that as a team, there might be ways... there might be ways to structure a team or an organization so that people can be more bold. And the top idea that came to my mind when thinking about this was a concept that comes from the military, this idea of, command intent, right? Where...

Harry: 23:06

Oh yeah, commander's intent.

Jorge: 23:08

Exactly. And you might know more about this than I do, but as I understand it, the idea is to make goals very clear and the reasoning for achieving the goal very clear, and then allowing the people who are going to be executing in the field to make decisions on how to achieve the goal, rather than micromanaging their way up the hill or whatever. So that might be one. Another might be, you brought up the word"confidence," and I think that it would be pretty hard to demonstrate gumption to do the knocking on doors at midnight or the asking for the 50% if you didn't truly believe in the idea.

Harry: 24:00

Yeah.

Jorge: 24:01

So I think that having self-confidence, that might be something that might be a personality trait, but having confidence on the project and on the thing that you're doing is something that you could probably work on, right? I've developed more confidence in my life as I've developed expertise in certain fields, and I feel like I can be more bold now at the stage of life that I'm in now, I can be bolder than I was when I was much younger and didn't really know what I was doing. I think back to the story, I don't know if you've heard this, but there's a story of a 12-year-old Steve Jobs wanting to build some kind of electronic device and not having the parts, and he looked up Bill Hewlett in the phone book, the founder of Hewlett Packard, and he called them up, right? And he said,"Hey, I need these parts." And, he actually... like he got like an internship or something at Hewlett Packard. And that story is one of the reasons why I think there must be some of this that is innate because having the self-confidence at twelve to actually do something like that is not something that all of us have. But it is possible to develop confidence in your abilities as you develop mastery over a subject domain, a practice, or a field or what have you.

Harry: 25:27

Yeah, this is such a rich topic. There's so many different places that we could press on this to go further. And it's so tied, so deeply tied, to so many of the other things we've spoken about. Because it's not just about confidence in yourself and your skills and your ability to exercise those skills, but sometimes it's about the belief that you have in the thing that you're representing and the more closely that's tied to your identity, the easier that's gonna be to feel confident in it. And so it's easy, if I find a tool, for example... Okay, so here's a great example. You can't see this... Well, you can, but most people can't see this pen that I'm holding up. And this is the most amazing pen ever. Like, I have been on a hunt for this pen my whole life, and it's this whole story we don't have time for today. But I bought every single remaining pen from the people that made this. It's no longer made. And I bought their entire stock of these so I could have the rest of them for the rest of my life and give them away as gifts. And Jorge, I'm gonna send you one. And it's a custom-made, Kickstarter pen that holds a Fisher Space Pen cartridge. It's magnetic. It's short. It's incredibly well-weighed. It's like this perfect pen. And it is tied to my identity as a communicator, as an explainer, as an author, as a designer. And not only do I believe in this product, but it is so tied to who I am that I can easily sell this pen for$500. It's nowhere near what I paid for it, but I want to keep all the ones I have. But if you're willing to pay me$500, I am willing to show you every reason why this is the best pen in the world and I'm willing to demonstrate an extreme level of chutzpah in saying,"Look, I'm not gonna sell it for less than$350. I don't care that you can get something like it for$40 U.S. The fact is, you can't get this, and I know how awesome this is." So, I don't feel like I'm being bold or ridiculous. I just know that there's only twelve of these left in the world, and I've got one of'em. And so when I lose this one again, there'll only be eleven of them left in the world. So it's, I don't know... I could just go on about this,'cause I think there's a difference between being confident in the skill of maybe selling versus confident in the thing that I wanna sell. And the more tightly coupled it is to who I am and what's important to me and what my values are and how I see myself in the world, the easier it is for me to show up. And I think that's the thing that's that Steve Jobs did when he was twelve years old.

Jorge: 28:14

It's almost like an existential confidence, right? It's like this thing is... this means everything to me right now. And you communicate that when you're on fire with an idea, that comes across in some way. Anyway, I think you're right, this might be a springboard for further conversations. I I just wanted to bring the subject to our topics here, because the more I learn about people who are high achievers, the more I'm reading about people who have gumption, who have this trait. And right now I'm in a Werner Herzog bender watching Herzog movies and listening to his audiobook, and he's someone who's the patron saint of gumption. Like he does these things that, I think he established a filmmaking school where he says he teaches two things, how to forge shooting permits and how to use bolt cutters, which is the"Best to ask for forgiveness than permission school" or something like that, right?

Harry: 29:29

That's awesome. Oh yeah, and I have a bolt cutter story. I'll save for another time.

Jorge: 29:33

But I think those are the people who do things right? The people who actually get things done, oftentimes are people who have this trait. So anyway, it was great discussing it with you, Harry.

Harry: 29:44

Yeah, a lot of fun. Thanks for bringing this up. And I have a road trip coming up in a little over a week, and I'm definitely gonna get a copy of that audiobook and listen to it on the road. It sounds fabulous.

Jorge: 29:53

Oh, it's a treat.

Narrator: 29:57

Thank you for listening to Traction Heroes with Harry Max and Jorge Arango. Check out the show notes at tractionheroes.com and if you enjoyed the show, please leave us a rating in Apple's podcasts app. Thanks.