Jan. 7, 2022

Listener Favorites: Josh Linkner | Leveraging Entrepreneurship to Design the Future We Want

Listener Favorites: Josh Linkner | Leveraging Entrepreneurship to Design the Future We Want

Josh Linkner joins us to talk about his unique perspective of entrepreneurship and how it will enable us to become the architects of our future. Find out why playing it safe while you're young is the riskiest thing you can do, what entrepreneurshi...

Josh Linkner joins us to talk about his unique perspective of entrepreneurship and how it will enable us to become the architects of our future. Find out why playing it safe while you're young is the riskiest thing you can do, what entrepreneurship really looks like, what enables the coexistence of ambition and fulfillment, how to make the most of a pandemic as well as what is going to prevent many of us from doing that.

Visit Josh Linkner's website to find his book, his blog and his inevitable podcast | https://JoshLinkner.com

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Srini: Josh, welcome to the unmistakable creative. Thanks so much for taking the time to.

Josh Linkner: My pleasure mate, to be with you today.

Srini: Yeah, it was my pleasure to have you here. So I actually came across your work by way of somebody on your team. And I was very intrigued by this, the sheer diversity of what you've been up to.

Srini: And there's one part of your bio that made me want to ask this question. And that is what was your primary extracurricular activity while you were in high school? And what impact did that end up having on the choices that you've made throughout your life and career?

Josh Linkner: My primary extracurricular activity in high school was playing jazz music.

Josh Linkner: I'm a very passionate musician. I've been playing out for 40 years. And I would actually was when I was in high school, I was able to join in here in Detroit. There's an urban university called Wayne state university. So I somehow talked them into allowing me to join the college jazz band when I was in high school.

Josh Linkner: So I would, was able to leave high school early and drive to downtown Detroit and play jazz. That was profoundly impactful by the way, in my career. As I've been building companies now for many years, it's really like playing jazz. You're improvising you. Of course, correcting you're taking risks.

Josh Linkner: You're trading the Baton of leadership and jazz to me is really, I think the ideal metaphor for what we're facing today. Before we get more to that, though, my secondary primary activity in high school was smoking. And that probably didn't get me quite as far. So I've switched to to wine and

Srini: scotch these days.

Srini: Yeah. It's funny because the reason I asked about that in particular was because I was also a tuba player in high school made it the Allstate band, USC school of music. And that was the end of it. One, you mentioned that you decided to go out and seek out the ability to go and play in this college jazz band while you were in high school.

Srini: That is an unusual drive for somebody who is in high school to say, okay, you know what? I want to be good enough to go and do that. And I'm not satisfied with what I'm getting into high school. What is it about you? W what do you think that comes from?

Josh Linkner: A couple of factors I've always been really intense.

Josh Linkner: I just, and anything I do, I take probably to the unhealthy extreme, I, when I was a little kid, I used to build and rebuild dirt bikes, and again, took it to an unhealthy team. So I just tend to be really intense with whatever I'm doing. The other thing though, is that my grandmother said something to me and I always remembered.

Josh Linkner: And she said, in any situation, somebody has to be the best. Why not you? And whether you're in a class of students, why couldn't you be the best? Or if you're with a bunch of musicians, why couldn't you push the boundaries and get a little bit better? So that, that drove to when you unpack that a real craving for work ethic and achievement.

Josh Linkner: And so when I was playing music in high school, I didn't, it wasn't enough for me to just go play in bars, which I actually did. I'd sneak into bars in Detroit. I had to take it to the next. And so I was really driven and and I'm glad I was that drive has helped over.

Srini: So you mentioned sometimes to a fault, right?

Srini: Because I think that it's funny because I got told virtually the exact same thing in a different form from a band director who said, you're going to make all-state band someday. The moment I picked up the instrument where I had no natural aptitude for this thing. And I think that instilled this sort of, oh, that's the standard inside of me.

Srini: One of the things I wonder is how you balance that intensity and that drive and that belief that you can be the best without letting it become ego. Like how do you add humility into that and awareness that, okay, there are people who know more than you, because obviously if you've built companies you've been in the entrepreneurship world I think that, you have to be able to acknowledge the fact that you are not the best at everything.

Josh Linkner: Outstanding point. And it's funny because my strive for that is nothing to do with ego or cockiness. It's really quite the opposite. In fact, one of the attributes that I just have horror is arrogance at boastfulness and such. And I certainly hope I didn't come across the way. I actually think it comes for me anyway.

Josh Linkner: It's having that beginner's mind and knowing that, there's always someone going to be more accomplished and better. Yeah. No matter how good you get, or no matter how many accolades you managed to acquire it's the drive to push yourself to do more and be better. And to learn I'm a constant learner, constantly pushing the boundaries, causing, making mistakes, by the way.

Josh Linkner: So I, I'm proud of what I've done, but I have, deep humility and always have, and always realizing that there's probably a better way to do stuff. And why not go out there? Yeah.

Srini: So one thing that I see often with musicians in particular, those of us were in high school band, is that it just becomes one of those things that fades into the background of our lives.

Srini: Granted, a tuba is more expensive than a car, so it was what do I need more

Josh Linkner: and better than most cars. Yeah.

Srini: You seem to have sustained this thing for, 40 plus years. Like, why is that? Why have you stuck with it and why don't most people stick with things like.

Josh Linkner: In my case, it's just such an interwoven part of who I am.

Josh Linkner: I just love jazz because it says dangerous art form and you're taking risks. If I go play a jazz gig and play everything safe, I just get laughed off the stage. But if I you're like required to try new stuff to innovate and real. And if I play a clunker, you just play it twice more and call it art.

Josh Linkner: Everything is fine. No kidding aside though. It's it's just part of who I am. And it's funny, I've had the chance to start building cell five companies. And I think of that is just playing jazz. It's just using a different set of instruments, but it's the same thing. It's, it's taking responsible risks.

Josh Linkner: It's sharing leadership it's course correcting inevitable setbacks. And I just like grading stuff and whether it's in business or writing a book or playing a jazz gig. So for me, it's almost like it's not so much oh, darn it. I gotta get on the treadmill. It's a chore. It's more just I just love it.

Josh Linkner: It's my muse. So to speak. And it answer your question. Why people don't stick. It could be a couple of things. One is they're just not passionate about it, and there's nothing wrong with trying different things and staying with what you're passionate about. But I think one of the things that people get frustrated with is this sense of perfectionism.

Josh Linkner: And they say I'm not good enough, or I guess I can't get better. And it gets back to that growth. There's a reason you say you practice music. I'm still a practicing musician, which means that you're still learning and growing. And so if you take the weight of the world off your shoulders, that you have to be, at some crazy level of achievement or you should quit.

Josh Linkner: I think that's why many people quit for me. I just keep it like learning and growing and. I

Srini: think that it's interesting to read to passion because I think that what I realized after spending two weeks at a school of music of New York and the summer was that I thought, oh, wow, this is not the life that I want.

Srini: And the only reason I genuinely liked this is because I liked the attention and I liked the spotlight. And that is definitely not going to sustain me as a person who might become a professional to a player since you are literally never in the spotlight. You're in the background the entire time.

Josh Linkner: Yeah, that's interesting. And it's funny too, that's, some people are driven by spotlights and extra transit factors. For me, it's just deeply rewarding. It's like a soul shower or something when you're playing jazz, because you're just, it's intrinsically, it fuels me up. The other thing I think is just, it's such an extension of who I am now back to the, the childhood stuff.

Josh Linkner: When I was a kid, I always felt like an old. Or a misfit and it wasn't in a good or bad way, zero judgment. But if there was 20 kids in a room, I would always think like there's 19 of them in one of me. And again, it was no way of thinking better. It probably, it felt worse than most kids but I always felt different and jazz is cool too, because there's, it's not as mainstream and it's this art form.

Josh Linkner: It's a little bizarre. And I guess there's something that's appealing to me about that also because I like being a little weird and being a bit of a.

Srini: Yeah. You mentioned before we hit record here that you're a Detroit guy through 32, stayed there, most of your life. And I think that for those of us who are not from Detroit right now, what we pretty much see as a city in shambles that seems to be struggling to, to get back to what it once was.

Srini: What is the experience of being a Detroit person through and through, like from high school up until now, taught you about life entrepreneurship. Like how has that influenced the way that you've started building sold business?

Josh Linkner: There is a deep connection for me and my hometown of Detroit. I was born in the city, not the suburbs as were both of my parents and my grandparents.

Josh Linkner: So there's a lot of, a deep rooted connection here. And the tribes fascinating to me. It's really, it's a city with a soul. It's this gritty underdog, Tom has been beaten down but there's this real spirit and. That exists. So I think getting back to that weirdness, I've always felt a little like the outsider.

Josh Linkner: I'm not from either coast, for example, I don't have a Harvard MBA, but there was that sort of Detroit grit where that Detroit hustle and what we do a lot of things poorly here in Detroit, and we're working on improving those. There are some really wonderful things and it's that sense of there's a sense of community.

Josh Linkner: There's a sense of being creative. There's a sense of making stuff. And I just, I'm like a really deeply proud of Twitter by the way. Detroit is a fascinating. I think what many of us face, because, a hundred years ago, Detroit was the Silicon valley of darkness. But then frankly, we lost our way, as other cities prospered, we sank and it's because I believe we got away from our creative roots.

Josh Linkner: We started administering automotive corporations instead of building cool cars. And when we got away from our creativity, which of course is a passion that you and I both share our city really crumbled and we became a punchline. But what's happening today is magical actually.

Josh Linkner: And we still certainly have many problems but there's once broken city. It's now rising from the ashes. And I actually believe it will be studied for decades to come as one of the greatest turnaround stories in American history. And it's partly this tenacity and resilience and grit and. That, that, that exists, that I believe will become our salvation.

Josh Linkner: And largely because now finally, as a community, instead of trying to rebuild the old Detroit, we're trying to create a new one. And so it's the injection of tenacity with creativity, create a resilience. You might say, which I think will fuel our rebirth. And then there's so many lessons for all of us to learn from that because we all get knocked down and we stumbled and we have setbacks.

Josh Linkner: And I think there's so many sort of wonderful nuggets to take from Detroit story. Of from great Heights to, to tragedy. And now back the triumph. Yeah.

Srini: So a couple of things I wonder I do want to talk about, this tenacity, creativity and grit that comes from that environment.

Srini: What misperceptions do you think that those of us who only experience Detroit through what we see on TV or through, the Michael Moore movies of, seeing Flint, what misperceptions do you think media creates about a place like.

Josh Linkner: One is that all of Detroit, as it looks like a war zone that there's, burning tires in the street and it's not safe to stop at a stoplight and this type of thing.

Josh Linkner: There, there are certainly spots like that. But I believe there are spots like that in any major city. You pick a major top 20 city, you're going to see areas of crime and poverty and and the what I think they miss is that Detroit has a lot more.

Josh Linkner: That there was a flourishing art scene that there's a tech sector. Now that's starting to build real companies that there are creative, smart, talented people. And so I think that, the over exaggerations of where we call it ruined porn, where it's, all is, these bombed out buildings.

Josh Linkner: Not that those things don't exist, but they're not as prevalent as. It's funny. I spent a lot of time really working hard to rebuild our city back in 2010, my partners and I had this crazy idea. We're like, Hey, what if we started a venture capital fund in downtown Detroit? Not necessarily to make money as much as to make a difference.

Josh Linkner: So we thought, if we bought back the passionate entrepreneurs in the tech sector, not in manufacturing, not in automotive and technology, could we help restore Detroit as this beacon of innovation? And people told us we're nuts. They're like, you can't do this in Detroit. Are you crazy that I go to Boston, go to Boulder.

Josh Linkner: And so of course we did it. And what we learned is that there are certainly some disadvantages, but there's also a lot of advantages. We had a wonderful cost basis. We had access to incredible talents. University of Michigan is 20 minutes away and other major universities. And so in, in what others saw as tragedy, we saw opportunities.

Josh Linkner: And fast forward to today, there's now this thriving texting, and I'm certainly not taking credit for it obviously but there's real excitement happening in our city that I think is often overshadowed by the negativity that's portrayed in the media.

Srini: So you mentioned that there's a sort of grittiness, tenacity, and resilience that comes from having been put in an environment like this.

Srini: And this is something I'm just curious about because I was writing about this morning. It seems to me that so often in order to actually develop resilience, we have to experience adversity. We have to experience challenges or pain. So I wonder, for the person who does not find themselves in a Detroit, but has, grown up in the comfort of Southern California suburbs or anything of that sort, like the, leave it to beaver, hometown.

Srini: How does somebody find the capacity to develop that kind of grit, resilience, and creativity? Their lives have largely been ones of comfort and security.

Josh Linkner: First of all, I don't think you need to be in Detroit or Detroit, like place to have. Adversity is part of life. And that could be, even if you grew up in the suburbs, as you mentioned, maybe you struggled to make a grade on the test, or maybe you got dumped by a girlfriend or something.

Josh Linkner: So I think adversity is part of life. I think we need to challenge ourselves probably to push a little harder and recognize that those setbacks are really the portals of discovery, so It's not about avoiding setbacks or failures or stumbles. It's about embracing them and learning from them.

Josh Linkner: And that's really what builds. Self-confidence. I'm blessed to have four kids. Self-confidence for a kid. Anyway, it doesn't come by patting them on the head and telling them how great they are. Self confidence comes from overcoming challenges and get coming out on the other side. And so I think the best thing is parents and leaders that we can do is help people, learn from it and toughen up through those setbacks.

Josh Linkner: And whether it's a global pandemic setback or an economic one, or a relationship one or. Setback. I think those really are the nuggets that, that drive our creative capacity and drives us to become better. As people in later,

Srini: as somebody who has children who has had this very multihyphenate career, which I know, having experienced some version of this, that is a very nonlinear path.

Srini: That pretty much goes against the grain of anything you were told while you're growing up. What is the advice that you have given your kids about careers?

Josh Linkner: So I have to, it's funny. I have two older kids into two little ones. I have a 22 year old, a 20 year old, and I have three-year-old. Got a big spread there.

Josh Linkner: But my older ones, what I told them is right now, this is the perfect time to take risks. So let's say they wanted to go start a company. Awesome. Go do it because there's only two things that can happen. And they're both good. Either a, it works perfectly and they go buy me a Ferrari or B if it totally fails and they fall on their face, but they learn so much from it that it was way better than if they went and took a job at a big five consultant.

Josh Linkner: The only thing is good before they have mortgages and kids and responsibilities and stuff. What a wonderful opportunity to take those risks instead of playing it safe. I just think playing it safe today is the riskiest thing. Yeah.

Srini: Let's talk specifically about the companies that you've built, because you said you gave what I hope is in my mind, I like to think of it as a sort of three-step framework, but it may not be in those exact order, but you said you've started built and sold.

Srini: Five companies. So I think that many people have a pretty clear understanding of what goes into starting and maybe they, so when you build companies, especially when you start with the idea that you're going to build it for growth, what goes into it at the beginning? What goes it into the middle?

Srini: And then, how do you come out of it having sold it? What are the distinct strategies, steps and things that, as a person who does, what you do has to think about in those days,

Josh Linkner: It's it's a deep question. I think there's a lot of misconceptions, most people think this term entrepreneurship, it's like even the word I hate the word it's like you imagine some fancy people sitting on a balcony with white gloves, sipping tea, and that's not what entrepreneurship is at all.

Josh Linkner: It's entrepreneurship is a blood sport. It's like street fighting. So it's not like you have some great idea in the shower. And then by the time you dry off, there's a limousine waiting and a whisk to often start off. Basically what happens is you have an idea that 99.9% of the time is wrong, but you believe in it.

Josh Linkner: So maybe it's directionally, but functionally raw. So you start something and you raise a little money and everything is a battle. Then the first thing that happens, you get punched in the teeth and then you dust yourself off and have another setback. And it's I think a lot of entrepreneurship is about overcoming significant setbacks and learning from them and pivoting and adapting in real time.

Josh Linkner: So the other misconception is that people think of the initial life. It's really more about the series of micro innovations, not one little innovation that drives the startup success. It's this constant tweaking and adapting and the little teeny ideas that keep layering on top of the first one that ultimately drive success and another misconception by the way.

Josh Linkner: Cause I've funded over a lot. Run a hundred. Is that the entrepreneurs should be, the the caricature who this larger than life charismatic, fills up the room, visionary. My experience anyway has been the ones that succeed don't necessarily have those attributes. They are often more.

Josh Linkner: Sometimes they're more quiet, they're more coachable. They're more introspective. They're curious, they're willing, they're execution focused instead of just, all vision and no, no execution. Those are some misconceptions, but early on, it's all about product market fit. It's about, can you build something that people want?

Josh Linkner: Will they buy it a second time? There's the word spread? Can you figure out the math so you can need them survive? There's a real, survivalistic instinct early on, how can you get this thing so it can breathe. And that's hard. It sounds glamorous and we celebrate those, but we often don't recognize for every, success story.

Josh Linkner: There's hundreds of setbacks. And even the ones that succeed, they didn't get there easily. The second phase, the build phase is then once you've got something that kind of works okay someone wants to buy my product and they're happy with it and I can make a little money at it. Then it's all about how do use.

Josh Linkner: And it's funny. I think more people have problems going too fast and going too slow. There's a great quote that startups often die from indigestion, much more than starving. And the notion is they try to do too much all at once. They try to grow too fast, they try to take it on more aggressively.

Josh Linkner: They haven't built the underpinnings that can sustain it. And that's a hard phase as well. And and then of course the last one, but the exit thing, that's much easier. It's a pain in the neck when you're going through due diligence and such but if you build something that someone's willing to buy that you're already 95% of the way there, the exit is more semantics, but I did just want to say one thing real quickly.

Josh Linkner: And that growth phase. There's, it's a really interesting dynamic that almost every company hits is that what got you here? Won't get you there, which means that most companies start and they weren't, but they should have ducked it together. And it works when there's smart people in the room and they all know each other real well but scaling it as a different thing.

Josh Linkner: One year in 2005, I had 88 employees at the end of the year, 2006, I had 260. And you're like, wow, that sounds so honorable. And how glamorous and you know what, that was just awful. First of all, and there's the CEO, the CFO, and the head of HR. Like I didn't have any senior leadership around it. So I had to figure out that out and it was a mess like we, and by the end of that year, our systems were all strained.

Josh Linkner: Our clients were pissed off our quality software and our profitability was down. It was rough. And really you had to rebuild the ship while you're flying it. The airplane while you're flying it. Yeah, like our systems and our processes didn't scale the way we hoped it would. And so that's really what a lot of entrepreneurship and building companies is all about is getting to one point that makes sense, and then quickly adapting and figuring out how do you leap from one point of success to the next and without standing.

Srini: Yeah. It's funny because Sam Altman released the entire Y Combinator startup school curriculum as a class at Stanford. And you can download it as a podcast. And, I go through that at least once a quarter as a reminder, but he, in his very first lecture, he says, people who are founders think you know, or who haven't actually started a company accompanied, think that it's going to be like this whole thing of going to parties and giving speeches.

Srini: And it turns out. Curses at all, founders faces that founders like to build and start things. But, building a company is a years long grind of execution which that stayed with me. And when you, it's funny, you mentioned, structure failing because he said when structure fails, it tends to fail all at once.

Srini: But I think the thing that stuck with me, the most of what he said that I really would like to hear your perspective on given how many startups you've invested in. And he said that, most. They think they're coming into this thing that, you know, Hey, I'm going to blow this thing up. It's going to be huge.

Srini: And three or four years from now, I'm going to be sitting on a beach somewhere, counting my cash. And he said that your greatest competitive advantage is a longterm view. And he defined a long-term view as 10 years, which is crazy considering how fast the world moves. And I just wonder what you think about that as somebody who invest in.

Josh Linkner: There was a real sense of wisdom to what he's saying there. I think that too often people think I'm going to build it and flip it and they make choices that are short-term only, and then those end up biting you longer, longer term. And so I think if you build something of sustainable value that you've got so many options, whether you sell it in 10 years or three years or 20 years, you've got something that that the underpinnings are truly valuable.

Josh Linkner: It kinda reminded me of there's a boxing saying that that basically, if you go into a ring as a boxer, I'm not a boxer by the way. But if you was like, Hey, I'm gonna knock the scout in the third. It rarely happens. What happens is on the other end is that you go and execute your game plan and you adapt in the ring and do all the right fundamentals.

Josh Linkner: And then the knockout just happens. You let the knockout emerge or let the knock at the knockout be uncovered. And that's the same kind of thing I think with entrepreneurs, if all you're focusing on is the. I think you're missing the opportunity to build real value in the meantime, which is serving customers and you're building a great team and culture.

Josh Linkner: And funny enough, when people were pitching me as a, as an investor and they all they talked about as the exit, it was a real turnoff because if you're not passionate enough to build something for the long-term something that has sustainability is something that's going to change the world in a real positive way.

Josh Linkner: Just thinking about the dollar signs of the exit is not going to get you through those tough moments and tough nights and weekend. When that you're going to need the fortitude. And you're only driven through those challenges with, I believe a compelling vision and something that's sustainable.

Srini: I know those cause we raised our first round of funding last, and it was one of those things where you realize you're like, wow, my life is about to change pretty dramatically. Now I'm accountable to somebody else and it, it fundamentally changes your behavior. But you mentioned, the fortitude and the tough nights.

Srini: And I think that this is something that we don't talk about nearly enough. There, really sad that some, what it takes off and is, a founder suicide for us to say, wow, we've got a mental health crisis here. In, the sort of startup and entrepreneurial community, people like Jerry Colonna are doing amazing work around this to address these issues.

Srini: But. What have you seen around this? How do we mitigate this issue? Because the reality is if you're a founder, this is something, my roommates are talking about. It's very hard not to have your identity and your self-worth intertwined with the results of your business because it takes up so much of your life.

Srini: And when you have to get people out of these messes, how do you get them out of this mental funk? Because I often feel like that can destroy a business faster than the actual result.

Josh Linkner: Yeah, it's such an interesting observation. And by the way, startup life, it's like your emotions are amplified.

Josh Linkner: The highs are high and the lows are really low. You have some wonderful wind and you feel like you're king of the world. And then you blow a tech issue and you just feel like you're in the gutter. And it's really hard because you're right. Our personalities as founders are so intertwined with the work that we do.

Josh Linkner: But I think we gotta got allow ourselves and it's like a cliche. It's almost hate to say it, but it's easier said than. Separating the judgment from the activities and that realizing that often, there's a lot of setbacks and failures that ultimately enable success. And so in the moment, setbacks stink and you still terrible and gutted, and that's just part of it.

Josh Linkner: But I do think over time, the more you go through that cycle, that the oscillation of highs and lows that you start to say, okay, I'm in the gutter right now, but I know there's going to be an, a wind coming up. Yeah you're less emotional about it. And then at the highs, you also become less emotional about it too, because there's going to be another setback coming up in the near term.

Josh Linkner: It's tough though. It really is tough. I do think one thing though that people need to know more, both about their creative process and certainly about starting companies. There's one of my favorite quotes is that the one thing that all great authors have in common is terrible for.

Josh Linkner: And I just love that because, we think of someone who writes a great book that they, they just sat down and plugged the typewriter into their soul and it just came out of masterpiece. And that's just not how creativity happens. Certainly not how startups grow. What happens is you have an idea it's wrong, you screw a bunch of stuff up, you make unlimited mistakes.

Josh Linkner: You feel like a jackass at the time. And then, if you keep at it and keep fiddling, eventually you kind of figure stuff out. And that's much more an accurate description. And so when we realized that, oh gosh, you just screwed something up. I just lost a client. I just lost two key team member.

Josh Linkner: My technology broke in the middle of the night. Those are the natural part of the process of growing anything. Kids don't pop out perfect plants, don't pop out. Perfect. And certainly companies don't.

Srini: Yeah. It's funny. Like I always tell people, it's like, when you sit down at the computer, it's like Joe Pesci said to Brendan Frazier in a movie with honors, he was like, yeah, this stuff is really coming out the wrong end.

Srini: I'm like, yeah, that's pretty much my daily, I was like, that's why Anne Lamont calls it a shitty first

Josh Linkner: draft. Yeah. And I just hope that people, whatever they're pursuing, whether they're building a company or pursuing their career or their passion or working in their community, number one, give themselves the creative permission to try new things, to experiment, certainly do it in a controlled and responsible way.

Josh Linkner: But instead of just only doing the thing you're supposed to do, get your yourself, explore the alternatives a little bit. And then when the inevitable setbacks happen, recognize that's also part of it. And that's almost if you're not screwing things up here and there, you're probably not going faster.

Srini: Yeah speaking of inevitable setbacks, we find ourselves at a very unusual time in human history, not just the history of the United States or the history of entrepreneurship, but as a society as humanity. I was watching this interview with Edward Snowden and the founder of vice news the other night, which if you haven't seen it, if anybody listening totally worth watching and.

Srini: And one of the things he said is that, that he was talking about, contact tracing, but there was a much bigger message. And he said, you know what? We're building here is the architecture of oppression. And we have to decide who we want to be when we come out of the other side of this One thing that I've really wondered, you as an investor, I curious about this because I've talked to economists about this, I've talked to all sorts of people about this, over the last 10 years, we've seen a maximization of self-interest that has made some people, lots of people, incredibly wealthy, particularly in the bay area.

Srini: And then also that has come at a certain cost. Like we have, if you look at sort of growth in, you were talking about scale earlier, growth to the point of ending up with somebody like Travis, Uber. And this, isn't a question per se, as much as something I just want to discuss with you as an investor, but do you think that we have maximized self-interest to the point of diminishing returns?

Srini: And where is the line? Is there such thing as enough in the world that you play in or is it as much as possible?

Josh Linkner: A very deep philosophical question. I could argue both sides of it. I tend to be of the the true capitalist society that, that self-interest propels. And when you look at in the broader sense, that seems to be the case that certainly can have a negative repercussions on some people.

Josh Linkner: And so I think that from my opinion, and I'm not making a political statement, but my opinion is that we should continue to have a an environment that, that promotes, self-interest and people, whether it's building companies or careers or whatever else, because I do think that it really drives innovation and.

Josh Linkner: Progress in general, but then also have a rich system to support those who are disadvantaged, who didn't have the same type of opportunities, as opposed to just leaving them to the wolves. And, it's tough though, because it's easy to say. Survival of the fittest that's Darwinism and that's what works and to a degree that's true.

Josh Linkner: But at the same time, if there was a kid born to upper middle-class parents in, in, in Palo Alto. And, he grew up next to some guy who became a headshot or a venture investor. And that was his best friend. And he funds his company because he went to Stanford. That's very different than somebody who grew up in a single parent home in inner city, Detroit who's whose father is in jail.

Josh Linkner: And her mother never went to college. And they are during a failing school system and didn't learn to read, so like the realities of it, I think we do need to continue to step on the gas of progress, but I think we also need to have some social responsibility, whether that's at the sort of corporate sector and or that the government sector of making sure that we're providing advantages trying to level the playing field as much as we can.

Josh Linkner: So people do have the opportunities that others do not.

Srini: Yeah. I'm part of the reason I ask the question is I feel that, particularly with our current administration, it's self-interest is pretty clearly prevalent there and, you see it and you think to yourself, maybe, we've gotten into this mess and I, like it's funny, right?

Srini: There's no question that I probably wouldn't have. That I do to continue this project for 10 years on capabilities company, if there wasn't some component of self-interest of the potential for our award, I think that there is an absolute grain of truth to that. But I feel that in some ways we've lost the balance.

Srini: And it's funny, you mentioned Detroit because we had Andrew Yang here as a guest prior to his campaign. And it's amazing to me that we've put so many sort of structures and systems in place that actually are literally basically getting in the way of the very things. Fuel our economy and move forward.

Srini: Like just massive amounts of student loan, debt, situations that people, like you said, can't get themselves out of. And then I think the other thing that I've become hyper aware of over the last year or so as I go through articles on medium and look at my own work, is this the, the, like our, we often don't acknowledge the amount of privilege that we have.

Srini: And advantages that we have over somebody like the type of person that you mentioned in getting to do the work that we do. You come out of the gate with a significant headstart.

Josh Linkner: There's no question about it. It's if you're riding your bike and the windows behind you don't realize it, but then when you turn it around, it gets a lot harder, real quick.

Josh Linkner: And so you're right. We don't necessarily realize the advantages that, that we perhaps have. Th the other thing that kind of stinks is that is whether somebody is acting in their self-interest or they're being more benevolent, more of a worthy or noble cause politics aside you can certainly argue that our current person in the white house, it tends to be more self-interested.

Josh Linkner: Whereas, in the past both sides of the aisle, by the way, we've seen people who have been more And I think that, with leadership, I think the responsibility is not only for your own kind of glory but also to, to share the the impact and the the resources that you create with others to tackle.

Josh Linkner: No those around you to me, why become a billionaire, if you're just going to hoard your funds and, be it be Mr. Scrooge about it. The reason hopefully that people are driven to for self achievement is not only for their own sort of in grit, in grandizing, view of themselves, but also to help others.

Josh Linkner: I think that's maybe a skill set or a mindset that we need to develop in kids that we're not quite doing.

Srini: So as somebody who has invested in companies, built companies, in the midst of what we're currently dealing with, we've never seen anything like this ever. I think the thing that struck me most what that Edward Snowden interview is, he said, this is basically a global opportunity for humanity to reflect on our values.

Srini: But what I wonder is, in your mind, as somebody who invests in companies build companies, what is economic recovery from a situation like this look like, because we don't really have any models to go based on we're in, completely experimental territory because it doesn't seem like anybody knows what the hell they're doing.

Josh Linkner: That's for sure. You're right. There's no model of the past. And we don't know. No one's crystal ball is working today of how long the pandemic is going to last, what the downstream repercussions are, to what extent governments will bolster it. Will there be a second wave?

Josh Linkner: When does the vaccine come? So all these factors are unknown. And I do think that the upside of it, I thought Snowden's comment. There was really good that it gives us a chance to reflect as humanity, but also gives us a chance to read it. And so I think if we emergent as either individually or collectively saying, Hey, all I gotta do is get back to it.

Josh Linkner: I think that we've missed an opportunity as opposed to during these down times, we can really reflect and say, what's a newer, better version of myself, my company, my team, my family, my community look like, and then get on with the hard work of recreating it. So I'm hoping that there'll be a lot of transformations and rebirths out of this with.

Josh Linkner: Forest fire that was a very devastating thing and it burns down and scorches the earth down to the core but also it's an opportunity for rebirth. Now you've got fresh oil and there's a chance to build something new. And so I hope that is devastating as all this is.

Josh Linkner: And I certainly don't mean to be glib about it. There also is an opportunity for us to take a hard reflective look and re-imagine something different version 2.0, and what is that going to look like again?

Srini: Yeah, my, one of my roommates said, he's this is a long overdue evolution in human consciousness.

Srini: And the funny thing is that I've seen some really good things, that problems that we've been trying to solve for a long time coming about because of this, the first thing I noticed was how people started using technology very differently. Like we went from texting to video chats all of a sudden, and it's that's really?

Srini: Yeah, this is my ongoing joke is like, we've had that capability for 10 years and nobody ever thought that would be a better way to communicate. But then even in places like India, I think the thing that, my cousin was telling me last night, he said, this has been a blessing for India because pollution, there has finally gone down.

Srini: They had a pitcher on some website in Delhi. There's some gate. I don't remember what it is, but they showed a pre coronavirus and it's just covered in. And apparently they're seeing blue skies for the first time in 20 years, Trevor Noah had this hilarious segment where he said there are these pandas in Taiwan or somewhere, and they've been trying to get them to mate for 10 years.

Srini: And they finally did. And he was like yeah, of course, nobody wants to mate, when somebody else is watching you having sex. But yeah, I think to me, you're right. I think it is an opportunity, but I wonder what would prevent us from missing this opportunity? What, cause there's going back to business as usual. It seems entirely likely that we can do that if we're not careful.

Josh Linkner: So well said, and I think the biggest thing that's going to prevent it. And fear is the same with our shared passion around creativity. There's that poisonous force that robs us of our best thinking fear and creativity can't coexist in the same room.

Josh Linkner: And why do people get locked into previous patterns is because they're afraid to try something new. And so I think that first of all, how are people spending their time right now? Yes, we all need to deal with the crisis. That's at hand. And if you run a small business, you've got to figure out like, Hey, how am I going to make payroll?

Josh Linkner: For sure. You gotta figure out how am I going to stay safe and feed my family for sure. But do we need to spend a hundred percent of every waking hour doing those things? What, if we, what if we did a balanced portfolio approach and said, I'm going to take, pick a number 60% of my time and be all freaked out about the current times, but that'll take 40% of my time and think about that.

Josh Linkner: I don't think he used that 40% instead of being heads down, that'll be heads up time where I can really reimagine. And so I think that the risk is that fear consumes us and we spend a hundred percent of every waking moment, cowering in the corner and only being so myopic that we can't look past tomorrow.

Josh Linkner: And then we emerge no better than we entered. I think the opportunity is the opposite is to carve out even some, not all, some of our time to be reflective, to be. Forward-looking to be imaginative and then we can come out stronger and better and newer and fresher and ready to take on the challenges of.

Srini: W I think that makes a perfect segue to, to ask you about innovation. I know that you speak to audiences and companies about innovation. What, what prevents companies from being innovative in terms of, somebody obsolete? How do you end up with a blockbuster going out of business?

Srini: Because they ignored Netflix or Kodak and going bankrupt because they didn't think digital was like legit or the entire music industry, basically thinking Napster was bullshit. Like, why does that seem to happen in history over.

Josh Linkner: There's a few reasons. The first of which is that success is a terrible teacher because it lures smart people into thinking they don't need to change.

Josh Linkner: And so it's hard to change because then, they'll say, oh, I don't want to kill the golden goose. And if it ain't broke, don't fix it. We have all these isms that are just ridiculous and out of date, the thing that people miss is that I think it's actually a really good metaphor. I don't know if you're old enough to remember the game of Frogger.

Josh Linkner: But when I was growing up in the eighties, there was this bit of game Frogger. And the whole goal is you have the little frog you got across the river, but you can't swim. So you have to jump on the back of things like a floating Lily pad or a turtle or an alligator problem is those things are moving.

Josh Linkner: And so the whole goal is you have to jump from one stable point to the next, but you can't stand there. If you stand there, you fall in the river. Do you have to keep going or else, just the mere act of standing still will seal your fate. And I think a lot of people and companies miss that, they believe that, Hey, I've cracked the code and I don't need to change it.

Josh Linkner: I've got it as if it was a permanent condition where instead, success as this tempered. Thing that's happening in the context of many external factors today that are changing faster than ever in history. So I think our job that's like being Frogger. We got to go, leap on one book, solid surface, but we can't stand there.

Josh Linkner: That's great. Let's celebrate the wins, spike the ball. We got to get to the next one pretty quickly because those frogs and Lily pads are only coming at an increasing pace.

Srini: So one thing I wonder is, you have throughout your life, seeing, I think for anybody who was an early entrepreneur you've achieved, I think what appears to be a pinnacle of achievement. So I wonder one, I always write about the myth of the I've made it moment.

Srini: And the reason I say this is because of something I heard and held him say to podcast. At home, at the height of his career, you've done the hangover movies, basically gone quote unquote made it. And he said to Sam Jones, the interviewer life is a series of false horizons and that has always stayed with me.

Srini: So I wonder in your own life how your definition of success and your values have changed with age? What matters to you now that didn't, when you were younger?

Josh Linkner: I love that quote to that series of false horizons. No, it's definitely true. The goalposts are always changing, I think there are so many myths about it.

Josh Linkner: If I have this car I'll be happy or successful if I have this house or this amount of money and those things are, that type of validation is temporary. It's elusive. It's it's like the the treadmill kind of thing. You never get off of it. I think as.

Josh Linkner: Grown in age and a little bit of wisdom, probably through lots of mistakes and stupid things that I've done. But I, I tend to value more impact than than personal gain. So like I measure success that I changed someone's mind or did I help them in a way, or did I make the world a little bit better?

Josh Linkner: I'm not saying like a politician. I am, and I certainly liked nice things and all that, but when I get more juice than. Bye bye. Like making a difference and that, that feels more sustainable than just the temporary kind of crack pipe hit of. Hey, I just closed a deal or I got some money or got a new car because those things do big quickly and they aren't as, as sustainable in terms of pure joy as one might think.

Josh Linkner: So yeah, I think today, my definition is, and how many. For me anyway, I try to continue to push myself in terms of growth. Like how can you achieve more and do more and be more but also how can you make a bigger difference on others and on the world in general? I know that sounds again like a bumper sticker.

Josh Linkner: I'm not trying to be that way. I truly that's how I. But you know what, I'll tell you what gets me fired up. I get an email today later on from someone who says, you know what I read your book five years ago when I was an intern and company in London, and today I just opened a company. And something that you said in that book gave me the juice to get.

Josh Linkner: And I don't do that in a boastful way or in a take credit way. I don't go share that with everybody and brag about it on Instagram. But those are the moments that are really exciting when someone tells you that you helped them because of something that you did buy their first house, that is just really intrinsically

Srini: rewarding.

Srini: I'm so glad we're finishing with intrinsic rewarding. You talked earlier about how the goalpost keeps moving and my friend Ryan holiday was here. He said, basically we all believe that there's next level of achievement or significance or whatever it is.

Srini: And he said, and that belief is actually good because he said it drives growth. He said, if nobody, if everybody was content being Senator, nobody would run for president. And he said on the aggregate level, it's good. But on the individual level, it's a lie. And that really stayed with me. And the reason is I wonder, even after, achieving everything, like how do you have the combination of ambition and fulfillment at the same time?

Srini: Can those two things simultaneously exist?

Josh Linkner: I think those things absolutely can coexist. First of all, for me I am I'm con constantly. Disappointed with the status quo, no matter how good things are. And it's not a, in a way like, oh, I just need more and more, but it's more like, Hey, if we're just sitting around and being happy all day, like we're not moving the world forward.

Josh Linkner: And that funny enough ties to fulfillment because to me, there's nothing that's more fulfilling than pursuing something worth doing. And so for me, I get the most joy probably in the act of progress. So in other words, those things beautifully cascade into one another. If you're dissatisfied with the status quo, not because you are unhappy or on grateful not at all, but because you say it, you see the possibilities, how can I make it even better?

Josh Linkner: How can I drive more progress? And obviously the world isn't utopia. So there's plenty of real problems that need to be solved. And for me sitting around basking in your previous glory, watching sunsets all day like that is that's irresponsible. If you have the opportunity and the wherewithal or the.

Josh Linkner: Smarts to go make the world better. How dare you sit around on the sidelines and drink margarita, and so on the other hand, if you are dissatisfied with things as they are, again, not because you're a bad person or cocky, because there's real things that can be improved in our world. Then going after it not only keeps you energized and motivated and sense of urgency, but that in and of itself becomes fulfilling because you're spending your days on a worthy cause rather than, twiddling your thumbs and planning too much.

Srini: This has been phenomenal. So I have one final question, which is how we finish all of our interviews at the end, mystical creative. What do you think it is that makes somebody or something unmistakable?

Josh Linkner: Unmistakable? I think that what makes somebody unmistakable is the. Truest possible connection of them as a category of one, the raw authenticity, we talked a lot about Detroit when people say, oh, let's go become the Silicon valley of the Midwest.

Josh Linkner: I say, why don't we become the Detroit. And being unmistakable is just being unapologetic of who you are and celebrating what makes you different, not what makes you the same. And to me, the worst insult in business in life is if you could easily be mistaken with your competitor that's just tragedy.

Josh Linkner: But on the other hand, I'd rather lose a deal than be easily mistaken. And I think that applies to people as well as, just being the truest incarnation of ourselves and not trying to be someone that we're not that's to me. What makes somebody on this?

Srini: Awesome. I can't think you enough for taking the time to join us and share your story and your insights with our listeners.

Srini: Where can people find out more about you, your work and everything else that you're up to?

Josh Linkner: Yeah, thanks so much. Just my website Josh or.com. I've been writing a blog for 10 plus years. Every weekend. We have a podcast launching and books and all that but even beside all that if I can be of help to anyone I'm always happy to, it's just my name, Josh.

Josh Linkner: That come and up real quickly, too. I just wanted to thank you for doing this podcast. What a wonderful gift you're giving to the world. I know you've had amazing guests and I'm humbled and honored to join the list, but you really are doing wonderful work here, and I just really want to celebrate all that you're giving back to the world.

Srini: Thank you very much. And for everybody listening, we will wrap the show with.