Andrew Skotzko

Alex Hillman: How to play the long game of business (#32)

Alex Hillman

Alex Hillman is a pioneer who has made it his mission to help independent creatives build sustainable careers. He’s the author of the recent bite-sized hit, The Tiny MBA, which is an insightful collection of short lessons about the long game of business.

Alex cofounded Indy Hall, Philadelphia’s first coworking space, and helped launch what became the coworking boom. He also built Stacking the Bricks with Amy Hoy, where they teach creative professionals how to bootstrap their own businesses.

As I believe you’ll hear, Alex is a very caring and generous person with his knowledge and experience and loves nothing more than to hear about how these ideas are helping people level up, so please reach out to him via email at Alex [at] tiny.mba and let him know what resonated with you.

Among many other things in this conversation, we talk about…

  • What does it look like to bring intentionality to our careers, to be able to connect the dots between starting where we are with what we have, and the long term aspirations and impact we want to create?
  • mindsets that will help you to have balance and equanimity in the face of uncertainty and having no control
  • the application of Buddhist teachings to a business career

This was a really fun conversation that will help you cultivate continuity in your efforts and invest in the long game of business, to benefit yourself and everyone around you.

Please enjoy learning with Alex Hillman.

And if you have a moment, I’d love it if you could give me a little feedback via this SurveyMonkey link. (It only takes one minute.)

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Transcript

Transcripts may contain some typos. With some episodes lasting ~2 hours, it can be difficult to catch minor errors. Enjoy!

Andrew 00:01:37 Alex, officially welcome to the show. How are you doing today?

Alex 00:02:11 I’m doing really, really good. Thank you for having me.

Andrew 00:02:15 Absolutely. We’re going to spend a lot of time today talking about a lot of the ideas in the book, the tiny MBA, but I actually thought we’d start somewhere a little bit different. There is something that I discovered about you that I had no idea that I think we share, which is, it sounds like we both have a pretty strong Buddhist influence on our thinking. You talk about a book that was really powerful for you in your own journey called the essential yoga Sutra. But one of the things I thought it’d be fun to start with is to talk about those ideas in particular, how they play out in reality of leading a life in the world and having a career and friendships and all of the quote, unquote, like we’re only attachments that can be so problematic when, when one starts to sit with these ideas.

Alex 00:02:51 Oh wow. So glad you’re starting here. I mean, there’s, there’s two things that come to mind. The first one is kind of broad, but I something that is livable in every minute of every day and maybe like more relevant now than any time in your, or my lifespan, which is really coming to terms with how little you actually control and how, the only thing you really can do the vast majority of the time is control your reaction. And I got a lot of that from the study and from that book in particular, and to go a little more narrow into some of the things that I still to this day think about from my very first read through that book is separating what happened from the story about what happened and how quickly the story morphs, the further you get away from whatever the incident is.

Alex 00:03:43 And so like, you know, we are meaning making machines. We observe a thing, whether that’s our true lived experience or something happening off in the distance and when nearly instantly we’re making up all kinds of things that are not actually on the page. So to speak about what happened and, you know, trying to associate things that happened in our past lived experiences, these pattern, making pattern recognition things and how powerful that can be for good and equally powerful, like to our own detriment or otherwise. So, you know, I think at the heart of the, the practice for me is the constant reminder that what I’m feeling and what meaning I’m making about it is he’s real in my head. And my feelings are real, but are not necessarily the same as the very thing that I am perceiving. And that is extra true. The further away from the thing, it actually is,

Andrew 00:04:39 Well, there’s two ideas that I think are especially salient one in our careers. And one just in 2020, the 2021 is we really have no control. Like we thought, Oh my God, we thought we had some control. I’d like, if there has ever been a lesson for this year, it’s that is bullshit.

Alex 00:04:55 Boy. Is that true?

Andrew 00:05:00 Curious, like what practices do you find helpful? We crave the sense of certainty so badly as humans in a reality that does nothing but constantly change. That can be kind of frustrating.

Alex 00:05:11 Not only that, but it makes planning anything really hard. Everything is just changing. And I think to your point, that’s really pushed the degree to which uncertainty shows up. If the try, I guess the trick is, is like, how do you live, not paralyzed? How do you live with the uncertainty and make a choice anyway? And how do you frame choices at a scale where the worst case scenario is the plans change? Cause they could, or maybe we can go so far as to say they will and you are okay. Early on in the pandemic, I tweeted out something to the effect of, you know, we’ve all just been signed up for a marathon, but we don’t know how long we have to run. And that tweet went pretty viral. But also, I mean, from, for, for that, I think it resonated with a lot of folks.

Alex 00:05:59 They’re like, why am I so stressed out besides the obvious reasons? And I think there’s like coming to grips with this being an endurance game is not the same as this is an endurance game for an unknown period of time, an unknown level of complication and challenge. So being kind to yourself and being, you know, saying like calibrating expectations, like it’s okay to get it wrong. In fact, I’d rather set my default to, I’m going to make a guess right now. It’d be pleasantly surprised when I’m right. It has kind of like helped reframe a lot of things and that doesn’t work for everything, but maybe the biggest solace and all of this is also knowing that I’m not the only one going through it. Like this is a talk about a, a shared lived experience. Although everyone is going through their own personal versions of this, and many people are going through a version that’s so much worse than anything I’m experiencing. I’m so fortunate and privileged to have the comfort that I have and the safety that I have in the family and the people, and even just the financial resources to, to not be stressed out in all of the extra ways that are for many people the primary ways. So, you know, staying grateful for that too is, is I think part of the reality calibration that I’m constantly playing with. Yeah,

Andrew 00:07:19 No, I totally hear you on that, this, so the second idea that I’m especially curious to get your take on this goes along the lines of that longterm thinking you’re talking about, right? Where do we think about outcomes? Where are we trying to get to what results are we trying to create? I found myself grappling with tension between that idea of being oriented towards an outcome and in like the fine line between that and getting attached to it because you start to dig into the philosophy underneath Buddhism, or one of the misconceptions I had was that suffering comes from desire, which is actually kind of a, for anyone who has not spent time looking at this is one of the hints that I’ve learned is that many of the confusing bits about this are translation errors because we’re a couple of languages, but we’re like three steps away from the original language. And so the original word for this in the texts is Tonga, which does not actually really mean desire as we use it in English. It’s something closer to craving or thirst, which is it’s this compulsion, this helpless, like you can’t help it, but that is to be distinguished from what, what might be referred to is like a wholesome desire, like a positive desire, thinking about these ideas of like attachment and desire and outcomes all at the same time. How have you, how do you think about navigating that?

Alex 00:08:25 So when I think about choosing that kind of orientation, I tend to start less with an outcome and outcome might be part of like the mental exercise of figuring out what it looks like, and maybe most importantly to communicate it. But for me, the outcome is more of an orientation, a bearing or a North star. And because a lot of my work through most of my career has been collaborative, uh, whether it’s creating a community like indie hall, building teams around software for technology products, I mean, and any number of other things, even just like selling a consulting project to a client, I might use an concrete outcome to kind of, you know, you’ve got to bait the hook for the fish you want to catch, but when we’re actually getting down to the work, there’s, there’s sort of a, you, you follow the through line from where we are through the outcome to where is the outcome actually getting us?

Alex 00:09:21 Like, why does that outcome matter in the first place? And I think if you don’t follow that, that sort of liner that arc all the way through the concrete outcome to the maybe more existential long-term North star, more bearing oriented. I think like for me, that’s the sweet spot to even say, I want to create a certain software product, which I think is a common thing. Even that contains something that is easy to become fixated and obsessed on, which is software versus a product, which can be lot of things that a lot of formats that serves an audience towards a specific goal or potentially a many goals. Right? So one of the hard traits that we you’ve got, it’s taken us like the better part of a decade to really figure out how to break people of that fixation, w which is, that’s a sort of a version of the, you know, fall in love with the problem.

Alex 00:10:16 Instead of the idea, I take that one step further and it’s like fall in love with the people who have the problem, because that’s not the only problem they’ll ever have, and you might have misunderstand the problem, or by the time you create a thing, the problem might change, or you might not be the best suited person to fix that problem. But there is another problem that you were bet it’s like being too fixated on, on that thing puts on blinders from observable opportunities to do good and do well that are right under your nose and possibly easier, faster, more sustainable, whatever it might be to act on that. Then the first thing that came to mind, or even the fifth thing, like just keeping eyes wide open is hard in general, it’s impossible. The more fixated you become on an outcome, but the North star approach, I think lets you take, you know, to use like a sailing analogy. You know, people set a bearing, but especially if you’re sailing against the wind, you have to tack back and forth in order to go to the direction you want to go. When people are trying to do things that are metaphorically speaking against the wind, that back and forth may actually be the fastest way to get there, which is super counterintuitive and momentarily disorienting. If all you can think about is the end destination rather than the near term destination that gets you, you know, incrementally closer directionally to the thing that actually matters.

Andrew 00:11:40 No, I really love that. I spent a lot of time thinking about outcomes. You know, we had Josh siting on the show who literally wrote the book outcomes over output, whereas shaken out with it for now is okay. I want to be outcome oriented as in like an of directionality, but process focused. The outcome gives me like the directionality, that sort of sense of meaning. But then I got to come back to right here where I am like, what’s the next step? What’s the next goal? What’s the next rhythm I gotta execute on. And that seems to be kind of maybe a way to navigate this duality. I really like,

Alex 00:12:09 It reminds me of a term that I’ve heard used and I think fits what you just described, which is altitude shifting and how there are people who are really great high level strategic thinkers. And there are people who are really great detail oriented process thinkers and designers and executor’s, but there are far fewer people that are good at both. And there’s even fewer people who can quickly zip between one and the other. And I think what you’re describing and I think that’s also a result of, you know, there’s some aptitude, there’s also plenty of practice being able to be aware of which one you’re in, in that moment and recognize when you need to altitude shift to the next one and to have the muscle to emotionally, maybe let go of one thing to create space for another allows you to do it faster than somebody who maybe because of the monkey brain keeps recycling that high level thinking, and won’t let you really focus on the small thing or the monkey brain. Cause you so mired in the detail in the weeds that you struggle to get back to the big picture thinking. So I think that altitude shifting is, I mean, I’m sure there’s maybe another layer past that where you see your doctor Manhattan, you see all things you see if you see time differently than everybody else, but I’m certainly not there. But I think the ability to oscillate between them quickly and on command is maybe a set of practices to strive for that is actually practicable.

Andrew 00:13:30 Yeah. I mean, it seems like a trainable superpower, right? I’m gonna think about that a little bit more. So I think it’s a perfect pivot point into talking more about the book. When you say the long game of business, what do you mean?

Alex 00:13:41 I want to run a business that outlives me. I want to run a business that can still exist in a hundred years. And there’s sort of two reasons for that one is that I think it’s not only possible. I think it’s actually quite common. Um, we have multi-generational businesses in traditional business sense. You know, we’re talking restaurants are often passed down through generations, a lot of brick and mortar, sometimes service businesses, the trades and there’s challenges and potentially problems with that. It’s always confused me that the technology world, which is where I grew up and where I, where I really started my career in web development and software in software products and things on the internet, things are so fast and people are just like building for a quick flip or the fastest buck. And there’s no endurance as that. Even an endurance makes it, makes it sound more like a sport than it really is.

Alex 00:14:38 There’s no durability. Um, and it’s always, I mean, everything has trade offs, everything in life has trade offs, but in that, in that speed based world, the trade offs I’ve, I’ve saw early in my career, it just made me really about what people’s priorities really were. And it made me really kind of anxious to be someone who felt like in some cases I felt like it was wrong, right? People were doing things to other people in a business, you know, work employers treat their employees is, you know, we’re not seeing that, you know, widespread reckoning of that, uh, in America, especially, but more broadly as well. And you know, I experienced tiny versions of that again as a white man. So I can only really kind of imagine the multitudes, the depth and the pain and trauma created when the person on the receiving end is anything but a white man, you know, but I see all of those things are, those are the symptoms.

Alex 00:15:38 I think of a deeper cause of everything for speed, everything for growth, everything for the, the quick flip and no one’s really thinking about what could I build that has the ability to grow over time, provide value for all the people that are involved. So that vague, I mean, why wouldn’t you want an employee who wants to be a part of your company for a decade, 15 years, 20 years longer, like in family-based businesses there people stay in the business because it’s family and they feel obligated sometimes. But when you’ve got employees, like I thinking about my friends at Wildbit, for instance, um, the software company here in Philadelphia, my friends, Chris and Natalie run it. And it’s sad that new Wildbit is an outlier in the technology world because they have multiple employees who have been a part of the business for over a decade, 14 years.

Alex 00:16:31 That’s unheard of in small technology businesses, you know, people who have had a 20 year career at Microsoft, but that’s already after Microsoft was a machine, right. That’s a whole other story. So, you know, I think there’s part of, part of the reason for the long business and why the long business and why this narrative is because when I was early in my career, it was really hard to find people. It was really hard to find examples that were counter to this dominant narrative of really what, what has been driven by Silicon Valley and wall street for the most part. And I feel very fortunate to have found and found early on people like Tara hunt is one of the first people who comes to mind. We were talking about her before we started chatting today, who, you know, Tara and her business partner at the time, Chris were the first successful professionals that I saw putting priority on the things that I thought should be valued, which is human connections and relationships, you know, finding a higher purpose that brings people together.

Alex 00:17:32 Co-creation and all of these other things that really, I think they’re critical foundational pieces to the long game. I watched them not only say it out loud and they were some of the first people that I, I saw say it out loud, but they were successful doing it. And it suddenly made it less scary to say it out loud and, and maybe try it myself. So there’s a goal in this book for me, which is if somebody reads this and you read something and you go, that’s a thing I’ve always thought, but maybe this is the first time you’ve heard somebody, not, you say it out loud, I’ve been on the receiving end of that experience and know how powerful it was for me and how much it shaped me as a person. And it’s shaped my career. Like those are the experiences that I really want to hear from people when they read this book.

Alex 00:18:10 And that’s, you know, I want people to see that the long game of business is not only possible, but it is accessible and subtext like it’s normal, like the Silicon Valley outlook, the thing that, you know, Inc and entrepreneur and the end, like the new cycle talks about is dominant narrative, but it’s not dominant in existence. And I just want to try and contribute to a narrative that, that maybe can help bring the true dominant existence interview for more people to help them either realize that their ambitions and goals and their worldview and what they want and see as possible in business. I mean, it’s as simple, it could be as simple as you can be in business without being turned into an evil maniac would be nice to have some more examples of that out there in the world. And I don’t think you can get that without taking a long time.

Andrew 00:19:06 I’m so glad that you explained that. And it also makes me understand completely why we were introduced because we share that goal of really trying to affect what business is, what it’s for and what it can be. That’s very much central to my own longterm aspirations. I went through a similar journey myself of, you know, I started my career in, in the tech, you know, the, the VC backed tech software world. And it’s so baked into that world that you don’t, it’s almost like the David Foster Wallace essay. This is water. You don’t even realize you’re swimming in it. And until somehow you, you break away and you realize like, Oh wait, like I’ve been in a, in a container that worships at the altar of scale above all, or is just aiming for the flip, like you said. Right. And, and it’s sadly few and far between that.

Andrew 00:19:48 There’s people creating things with real intentionality, like we’re talking about here. So that’s why I think the reason that I loved your book so much, and, and I highly recommend everyone get it. We’re going to link to this on the show notes. It’s a quick read. Honestly, you can read it in like 30 minutes on the couch, which I loved, by the way, it was like, Oh wow, you just, we did the thing that I wish every business book author did where you just, and you just told me, like, you just cut the crap and you just told me that they’re like the straight dope. No, it it’s like really short. Really. I highlighted a bunch of stuff and I’m really glad you did that because it’s like most business books should only be a long essay. And you know, this was, was beautifully done.

Alex 00:20:21 Thank you. And what you just said is right on the money you end up with business books that are like 250 to 400 pages, you’re going to invest two, three, four hours in reading each one, which isn’t a bad thing. And frankly, for one really valuable idea is a great investment by my mind. But I kind of wanted to flip it around and say, you know, can we increase the surface area of number of useful things that you can take away in a very short period of time and how quickly even one or two of them could be useful. Basically, I get a hundred shots at giving you something useful in 30 minutes, which is upping my odds of giving you something good. But it also ups the odds of those things being useful soon, right? And because it’s only 30 minutes, or even if you don’t read it cover to cover, just like, you know, run your finger through it, pick a random page or two and read a couple of things and see how it shows up for you that day to be able to do that a couple of times a year, because it doesn’t require you to like get into the whole game.

Alex 00:21:21 My hope is that people, this is something that isn’t necessarily a reference book in the way. We think of a reference book where I go to look up a thing, but where I go when I want to start up rejigger my brain a little bit, and or if I’m feeling stuck or slow, or just like looking for some fresh perspective, a lot of them aren’t necessarily a lesson in the explicit sense. Although what you might hope is you read it and it makes you think a thing or feel away. And then if you interrogate that something, you will learn something that is where the lesson comes from. So are individual sparks for that sort of thinking. But if the difference between jumping into a big open world video game, that you’re going to play for 40 hours, but if you put down somewhere, you’ll feel guilty about it versus, you know, a mobile game.

Alex 00:22:05 There’s a reason candy crush is super successful. You could pick it up, play it for 20 seconds and put it down. My book might be the candy crush of business books. One kid had a better impact on people’s lives, in candy crush, but I think that’s, that’s the differences. And that’s even without considering just like the world that we live in. Now, the attention span people have, people want all different kinds of books. This book is only really a book in, in the FA and like the packaging in a lot of ways, he reads differently. The format is it’s a feature and it might be one of the bigger features than is obvious until you’ve gotten through.

Andrew 00:22:43 You know, it’s going back to this idea. It’s like the long game, right? You know, there’s a word that’s been popping up in my mind as I’ve been sitting with and really leaning into a lot of this types of material with there’s one page where you talk about service businesses are about a thousand times easier to start than product businesses, but they’re a lot harder to grow past a certain threshold. Almost all the successful people. I know started a service business, then raised rates to reclaim time and invested that in growing more durable revenue streams, I had been struggling with that idea a bit. And I think this is going to be useful for our listeners because everybody, I think listening to the show cares about building the kind of business that you just described and that I’m also interested in seeing more of in the world, maybe another way of saying what you’re trying to say or a word that might sum it up.

Andrew 00:23:21 And I’m curious if this lands for you is continuity. I like that. Yeah. Where I struggled at first with their step approach was like, Oh, it can feel so frenetic or sporadic. Like I’ll, I’ll just, I see this option over here. I’ll go do that thing. And then I see this other thing over here, I’ll go do that thing. And there sort of was lacking a through line and what I am kind of hearing in, what you’re saying is this idea of, you know, you, and really, as I understand your approach is using your audience as the through line, like building continuity with it, with a group of people you want to serve over time.

Alex 00:23:51 Yeah, no, I think you, you, you summed that up perfectly and continuity is such a really interesting word. I think about continuity a lot in the community building space as often a missing piece, people do community building where, you know, there are individual events or instances of bringing people together for a specific period of time with a very specific purpose, but nothing happens in between. And without that thing happening in between, there is no continuity. I think people mistake the events as the community, the events or the on-ramp, the continuity of the community, right? The fact that people have the desire to continue coming together when the event is over and before the next one begins is the opportunity to create a platform for people to come together, to serve one another. And that’s, what’s at the heart of community. And to draw that connection between that and business, I think is really astute because it’s the same thing where products are the on-ramp, you know, which products, I mean, I think another thing that’s kind of confusing about the stair-step approach and, and even frankly, what we teach and, you know, Nathan Barry has, has talked about this as, you know, the ladder of wealth creation.

Alex 00:24:54 I think these are all complimentary views of the same thing, which is about building advantages based on where you are now with what you have now, so that you can then use those new advantages with new information to build the next set of new advantages, where things go haywire, I think is when people do take a frenetic approach and they build a thing and it’s doing even kind of well, and they go, cool, that’s doing well now we’ll go do the thing. And they throw away the advantages. They just built in the last step to create something new, or maybe you don’t need to all the advantages. Maybe it’s throw away some of them. So, you know, to create your first successful product or like let’s rescale product, like to create a blog post that people read and share, right. To create a podcast episode that people commit an hour plus of their time and talk to a colleague about it. And then that colleague wants to listen to it. Like those are products to, to have done all of that work and succeeded, and now built an advantage. And the advantage in this case, I’ll say is trust. They received the thing that you gave them and they got something out of it. And now they trust

Andrew 00:26:02 You to be able to do that again,

Alex 00:26:04 To not leverage the trust that you built with that, even though one person I think kind of misses misses the whole arc. So yeah. Continuity is the audience for sure. And the beautiful thing is, is people I think all the times get worried is like, Oh, if I pick an audience I’m trapped in that audience forever. I always remind folks like, no, no, no, no audiences is a maybe deceptive term. Cause it sounds like a really concrete thing. And it’s not, it’s a group of people who have a thing in common and that’s about it. And the beautiful thing about a group of people who have a thing in common is there’s a good chance. Those people have more than one thing in common and there’s a good chance that they are connected to other people who have groups of things in common. It’s, it’s just a way in, right.

Alex 00:26:45 And so rather than the sort of frenetic hopping from, you know, Island to distant Island, I think you can build much shorter bridges to navigate. I mean, even just a concrete example like Amy and I, and even before Amy and I started working together, Amy was mostly building an audience and serving fellow software designers and developers like herself. And we still have audience members to this day that know her from, you know, Ruby on rails, cheat sheets that she made in 2006, which is in itself, I think a Testament to what you’re describing as continuity. Those same people that were interested in Ruby on rails eventually became interested in business, right? Same person, new interests. We contain multitudes. And that is both informant and over time. So again, I think it’s build trust with the people who are best suited to reach recognizing that the more you learn about them, the more you connect with them, they will grow just as you will.

Alex 00:27:39 And you will have opportunities that you can only have by having that sort of long-term investment and relationship with that audience to then navigate and say, okay, we’ve spent the last several years focused on helping people start a business. Now I’ve got a bunch of people that have started businesses. They’ve got a whole new set of problems, which of those are problems that we can help them solve. Or you’ve got people who are, you know, they built a business and now they’re looking for their next, you know, maybe they even sold the business again, I’m not anti selling businesses. There’s like, that’s absolutely an option. And now they’re trying to figure out what to do next with their new found resources. You know, Amy’s channel a lot of her, her energy into activism, right. You know, we have audience members who have probably followed the entire through line of rails, cheat sheets to how to start, how to ship products, to how to build a business, to how to be actively engaged in politics.

Alex 00:28:34 Like that’s not an obvious path even really in hindsight, but I absolutely seen it, you know, and all it does is serve to deepen the relationships when the black lives matter, protests ramped up in, in, in June. And we were sitting down and going, what, what is our responsibility here? And that’s a big, complicated question and, you know, the, a career’s worth of answering to be done. But one of the things that we saw as a result of making that choice, which was not just to do a thing, but to also model behavior and encourage our peers to do the same was that people saw it. And that deepened the relationship between us. And what does that buy us? I don’t know. I don’t need to know. I just know that that relationship will be able to be turned into something more valuable in the future when the pieces come to you.

Andrew 00:29:27 I’m so glad you said that. So let’s, let’s make this turn and get a little bit more concrete for people. So we had this idea of the, the sort of the North star directionality, right. And then, and that idea of having this purposeful through line, and then there’s this idea and using that as direction, but not, not plan maybe. And then we’ve got this idea of continuity over time and then starting where you are building from there and using that almost like you’re, you’re, you’re stepping stones into the future. So let’s, let’s take a concrete example and outlets just because it’s top of mind, we’ll do, if you, if you don’t mind, we’ll do a selfish one from my own thinking. So I think like many people, I have lots of different ideas all the time for different businesses and different products and whatever. And I know from my own entrepreneurial training, that that is not the right place to start, the right place to start is with the customer.

Andrew 00:30:10 Right. And so let’s, let’s see if we can break this down. So like for example, a recent idea I was having was about, Oh, like I, I do product development work. So I have, I have a deep experience as like a product manager and a product leader, particularly in the tech innovation space. So at the sort of bleeding edge of technology and figuring out like, okay, like, is that even possible? How do we do it sort of Google X type stuff. And as a, as a team leader and manager. So like, those are sort of my, probably my three starting points of, in terms of like audiences I can connect with. So that’s, that’s a starting point in terms of, okay, those are people I can relate to and serve from my own lived experience. Okay, cool. So then long-term view, I have this really abstract idea about trying to change, you know, help shift the status quo of business in America.

Andrew 00:30:50 Like you also are. So we share that, that long-term goal. So how do I connect these dots? Like how do I, you know, and then I had this idea in the middle, which is like, Oh, okay, I see an opportunity maybe for building tooling that can help people track the changes in technology trends in the world to help them make better products that are at the bleeding edge of what is just now possible. So that’s like a business idea, but I don’t actually know yet if that’s like, I’m not going to start with that. I have that idea, but I don’t know that that’s definitely not validated, et cetera, et cetera. So how do we put this?

Alex 00:31:20 So let’s start there in the middle of that, where you’re like, there’s this thing that I could make, which is like the trap of somebody with the skills to make a thing that, and I’m not here to judge whether that thing is a good thing or a bad thing, or good idea, or a bad idea, or if it would be successful. I can’t know. Neither can you, that’s the point.

Andrew 00:31:39 Yeah. One analogy for this really quick that I’m curious if this tracks with it is like starting a new business or product. It’s like, it’s like building a puzzle, but at the beginning you don’t have all the pieces and you don’t have the picture on the box and you have to figure both of those out as you go.

Alex 00:31:52 I think I actually, I have an essay somewhere. If it wasn’t an essay, I used that analogy in a workshop around community building as well, which was community building is one where you have to figure out the picture on the box, except the picture in the box is not your picture on the box. Is there a picture on the box? So you have to kind of assemble it from, from the people in the community. And I think that’s actually part of the answer. The picture on the box is not going to come from inside of you. It will include your insights, your lived experiences, and you will be able to use the relationships and the relate-ability to connect into the communities that it can help. But the starting part is getting to those people and not getting to those people with your idea, but getting to those people with, within, through a lens of where they are both like physically not necessarily like physical in the world, but like, where are they?

Alex 00:32:45 Where do they gather? What do they talk about? What are their, you know, what are their hopes, dreams, aspirations, but also what are the immediate problems that they are feeling right now? And how can you help them with those immediate problems they have right now? And that might seem like such a really long, like maybe impossible arc from that to having world changing impact on an industry like you aspire to. But a that’s what we’re talking about. The long game of businesses being willing to say it might take me 10 years to get there, but it’ll be worth it. And if I get there in five, that’s even better. If I get there in three, incredible. And that might because I made some good choices. It might be because of luck. It might be either again, you can’t know, all you can do is position yourself in that direction and keep going.

Alex 00:33:31 So the starting point, I think we’ve seen over and over is embedding yourself in communities that you already belong to and being ruthlessly helpful and generous in public. And that does two things. And it’s a, it’s a really important to directional straight one is it shows you investing first, right? It shows you giving whatever it is that you have, but there’s a nuance to it that I think is really important. And people show up wanting to give their advice, their perspective, their point of view, without having earned the ability for the audience to care, what their advice perspective or point of view really is. And I have to go one step earlier, which is meeting people where they are. One of the things that Amy and I teach as part of the flagship course that we teach 30 by 500 is worldview as sort of an alternative to niche. When people are trying to figure out who to talk to, who their audience is, the word niche shows up or niche, whichever one’s right, but the world may never know how many licks does it take to get to the center with role.

Alex 00:34:35 So, so whatever, however you print out that word, it doesn’t matter because it’s the wrong goal. Anyway, what is more, what is actually, because you can’t really do anything with it, what is a niche, but an abstract human brain made up categorization. And then what do you do with it, right? How do you use a niche, right? At best, you can use it to say, you know, well, this is the, you know, the forums or lists those people participate. And this is the key words that they use, and that is useful. But the, the, like the real value, this is both the hardest, but also the most powerful layer is understanding the worldview, how they perceive the world, which includes how they perceive problems. They’re experiencing how they perceive their ability to affect those problems and how they perceive solutions in terms of packaging delivery, their ability to execute it and then get really concrete.

Alex 00:35:22 This is the difference between Apple and Android, right? It’s the person who wants a thing that was really, really easy to use out of the box, just works kind of anticipates what I want to do versus the Android. Someone who wants to tweak and tune it to way they want it to work, right? Those are two distinctly different worldviews. They are both potentially right for the person and has created the opportunity for Apple and Android to co-exist and just create Holy Wars on the internet between those people who do not share that worldview. I think if you go into the communities, you’re a part of, with, with two specific goals, one is to find people talking about the challenges they’re experiencing and try to understand how they perceive those problems before, or you start offering solutions, everything changed, changes. And again, back to continuity, like that’s a lens that can be practiced like a muscle.

Alex 00:36:17 And when you do get to a point where you’re creating tools, the solutions, I think, and I hope you can see how that would shift the products that you create. Because even if you do that, people really want to create cutting edge bleeding, edge technology, and tools for their customers, the way they, that, the way they perceive the ability to figure out what that is, is there, there’s going to be more than one answer to that, which ones you’re able to reach. Like if the people who want to use big data to figure that out exist, but you have no way of reaching them. I’ve got bad news for you. It’s gonna be very expensive for you to try and sell that product to that person. But if you’re trying to reach the people who want to go through ethnographic research, and those are people who you can reach, then that’s a completely different product.

Alex 00:37:03 It doesn’t mean you can’t build software to do it, but you see the difference both. I mean, it’s two completely different products. Or even if within the world of, you know, using big data, there’s multiple worldviews inside of that, that can result in different products. So all of this I think is maybe if you look at it as sort of like a fractal, like a fractal tree of understanding that all starts with the core of where do you find these people? How do you therefore, how do you reach them? What problems do they talk about? And through what worldview do they tend to perceive those problems that gives you fuel to start creating basically immediately, like I said, great blog posts, podcast, episodes, video tutorials, whatever it is, you want to put it on the internet. And that becomes your, I think that’s better than any validation out there because validation starts with my idea, is this what you want versus the notion of you told me that you have this problem, does this look like I understood the problem correctly very quickly, very cheaply.

Alex 00:38:04 And if you’re wrong, you’ve now got a feedback loop to figure it out. Versus I came up with this idea that you ran a person on the internet with all infinite biases. And how much do you really care about me is going to give me some feedback on how reliable is that feedback? How much feedback do I need in order to know whether or not it’s trustworthy? Like all of that data is really, really difficult to process. But if you can find one person who’s having a problem, you understand how they’re experiencing that problem and you offer them something that can help them, that they’re actually going to use and try. And you do that over and over and over and over. You will end up with and faster than you probably think is possible. A group of people who know that you exist and trust your way of looking at problem solving, and maybe most importantly are gonna want more.

Alex 00:38:51 And that’s the feedback loop that you can continue through getting those people on a newsletter that you can send them the latest, you know, so-and-so sent in this question. Here’s how I think about that. If that’s helpful for you. Awesome. Do you have a question of your own and you can see how that can grow, but it’s got to it doesn’t start inside you. It starts out there. The hard part, I think, as, as your work grows, as your products evolve as your business evolves, and even as your audience grows is it’s easy to get kind of lazy and insular and not be out there in the real world, because you’ve got, you know, a few thousand people to several thousand people, tens of thousands of people, hundreds of thousands of people that you can easily reach. I’m just going to listen to those folks. You should listen to and interact with those folks. But the, the longer you stay insulated from the rest of the world, the longer you are actually the harder it is to get back into the real world as well.

Andrew 00:39:43 I put that all together. So I have this sort of long, long range intention, right? That God knows all the different ways that will show up in. And I will pursue that goal and that aspiration, but start where I am now, which is with these groups of people, these, these audiences that I can relate to meet them, where they are from a place of generosity, understand what they’re dealing with, their worldview, et cetera, build trust with them, by helping them with those things and learn their problems and things like that. And if I do have a specific idea, like some tool to help them do X, Y, Z, you know, that’s fine. Or maybe it’s like, if you do have that idea, set the idea aside for the moment and say, who has that problem? And then go spend time with that person. I want to shift gears a little bit into some of the specific ideas from the book that are, you know, useful.

Andrew 00:40:24 I think for someone trying to build a company or a division for the long game. And then I pulled out that I wanted to have you expand on a little bit. One of them in particular was this idea of I’m going to call it sort of ownership, thinking like an owner, right? And so there’s a couple of places in there where you talk about different mechanisms that business leaders or business owners can, can employ to help foster that sense of ownership in the people that in their organization, you know, whether that’s like profit sharing or equities arrangements, things like that. So talk to me a little bit more about that. Like, what are the mechanisms that business leaders can use to foster that type of ownership thinking? And long-term thinking for people who are not them.

Alex 00:41:02 Yeah. I mean, I think the lowest hanging fruit here is at the root of this word. That is, I think I’ve heard it more in the last, I mean, in the last 60 days than I have in the rest of my career, which is inclusion, which is being proactive about who’s at the table for conversations and the decision-making. And I think because of all the ways we’re taught management, leadership, learning and work in this sort of like factory mode, right? So like, you know, it starts with school. We go to schools, teach us how to be factory workers and then ended up in these sort of either physical factories or knowledge factories as they were where people are intentionally and strategically siloed, not just in their jobs, but also in terms of decision-making. And I think the decision making is really where things get interesting and it costs basically nothing.

Alex 00:41:49 So before we even get into things like, you know, profit sharing and monetary incentives, which I think are valuable and important and often underexplored, I think that being intentional about including more people from the organization in decision-making then, especially like bigger high-level decision-making venue than you might think, especially because those folks in your organization have, they may not have the boots on the ground in the same place that you do. They may not have the same perspective that you do, but that’s kind of the point, right? They have the boots on the ground somewhere. They have a lived experience somewhere. And I think we’re hooks get maybe, maybe confused is when they think that everything that they hear they need to do, right. If we get more people from the organization, from the business involved in the decision-making, I can’t move as quickly and I’m going to have to do all of those things.

Alex 00:42:43 And neither of those things are true. I mean, you can’t move as quickly might be true, but I’d say that might be a good thing instead of a bad thing. I think giving yourself a moment to pause is a lesson worth trying at the very least and seeing what happens. But one of the things that I’ve learned over and over and over with indie hall as this sort of unique organization, that is not a cooperative, it’s not a representative democracy. I am the business owner and I have a very tiny team who helps on the operational side, but we’ve got hundreds of members. The thing that I’ve learned over and over is giving people an opportunity to give their perspective, make a suggestion doesn’t mean you have to do it. What it does do is if you think it’s a good idea, but it’s not going to be your number one priority.

Alex 00:43:26 You can say that B you can then deputize them to go out and do it. And now you’re giving them ownership, not only of creating the idea, but over the execution. And so within the whole, one of my favorite lines, my team has learned this to the point where members now honestly do it to each other, but use it in dialogue, which is, that’s a great idea. What can I do to help you do that? And it’s this little like Kung Fu move where you’re catching the punch and redirecting it in a way that says, and it’s not placing the burden on them. It’s creating an opportunity for them because I am here the subtext. And in some cases, the actual text is I will give you every resource. I know how to give you in order to make this possible, but I want you to have ownership over it.

Alex 00:44:07 I think the hard part of this is then calibrating expectations. And you know, what happens if that thing becomes successful. But I think those are all really good problems to have and bridges worth crossing so long as you have that open dialogue as part of the next steps after providing that opportunity, it’s like, it’s not yoga. Do this thing. It’s yours now. It’s, we’re doing this together. We’re going to co-create this, but you get ownership over it, I think is the easiest thing that people can learn how to do can. And the beautiful thing about it is it then start again. It’s about modeling behavior. If you have one team member, go through that experience, take ownership of it. Start earning credibility opportunities, growth. Other people in the organization are going to see that too and go, Hey, wait a second. I got ID. And now what do you have now?

Alex 00:44:52 You’ve got people coming to you with great ideas. Again, not all of them need to be great ideas. Some of them can be good ideas. They can try it out. Maybe I’ll sit down with you for 30 minutes and we’ll frame it down to like, what is the smallest simplest version of this to get it going? But now it’s yours to get going. The absolute worst case scenario is there, there is an actual no. And even in that case, I don’t think it needs to be a no. Instead it’s an, a learning opportunity for you as the business owner, but also them as the teammate for you to externalize why it’s a no, and maybe more importantly, here’s what it would take to be a, yes, we don’t have budget for that is not a useful response. There’s not budget for that, but here’s how we put together budgets.

Alex 00:45:32 Or would you like to come to the next budget meeting so you can see how budgets work or it doesn’t look to me like it has a thing that would allow it to pay for itself. But if you want to figure out a way that it can become a sound investment, here’s what basically it needs to have that built in from the start. If, again, if that’s the particular constraint, so turning your nose into, here’s what it needs to be to become a, yes has allowed us to empower so many community members to learn how we make decisions. So the next time they come to us, the decision is better formed than before, because we taught them a little bit about what it takes for us to make something be a yes.

Andrew 00:46:07 So I want to start to shift gears and kind of close out here with some rapid fire questions. First one is what is a quote or a saying that’s important to you? And what about it speaks to you?

Alex 00:46:16 The, the one that comes to mind is one from the book, but I’m also has, like, I don’t want to plug something from the book here. So the quote that comes to mind is both a quote and a very short article from Derek Sivers that I think the full article is at severance.org/obvious, but the quote is obvious to you, amazing to others. And the reason I think that I think about that quote a lot, and I reference it pretty often is it is really easy to overestimate the mundanity of something that we’re experiencing, because we have experienced it for somebody else who is observing it from the outside to see themselves in it. Right? So it’s not even about giving the advice. It’s just about creating that relatability. And I think folks are really quick to try to impress people rather than relate. And I think when in doing that, you’ve skipped over obvious, but, or I should say seemingly obvious to you, but often amazing, impactful, deeply connecting points of view that can or grow the person on the receiving end.

Alex 00:47:32 The other sort of related quote that as I was sort of saying that out loud makes me think of is the danger of comparing your insides to other people’s outsides, which I, you can sort of see how those are connected people. We do this ourselves and other people are doing it. So there’s a mindfulness of like how we put ourselves out into the world is always going to be incomplete, but that incompleteness is how we’re going to be perceived, which is not something we’re in control of to take this back to the beginning of our conversation. So just like do that and know that and be mindful about it, but also that’s a two-way street, is that when we’re perceiving other people and comparing their experiences, as we observe them and maybe feeling bad about ourselves or good about ourselves and smuggling, how much better that we are, there’s so much that we don’t know. So I think it’s just really valuable to keep that the incongruence of those two perspectives as reality, and just keep them in mind,

Andrew 00:48:26 Underneath everything we’re talking about here, there’s obviously a set of beliefs. Worldviews do use that term mindsets. What is a mindset shift that has really helped you? Where did you get really stuck in? What was the mindset shift that got you out of it?

Alex 00:48:40 Got a good one. And it’s Friesen. I started working with a management coach earlier this year because for everybody practice and skill that I have as a leader, I am a garbage manager. I use the highlights, how different those two things are. And part of that is because I manage the way I wish to be managed, which is basically not at all. And for most people that doesn’t work. So I started working with somebody she’s been amazing in a lot of ways, super, super helpful. We went through an exercise early on in working together where she had me break down the reasons why I don’t delegate things. It is not an easy thing. It does not come naturally. And when there are stakes for that delegation, or when it is your idea that you were then delegating, like when it’s somebody else’s idea, delegating it to them is infinitely easier because my stakes in that thing, or exactly where as much as I want them to be when it’s my thing, and I’m trying to delegate my thing, goodness gracious, that is difficult.

Alex 00:49:35 And Kara kind of forced me to unpack that. And I was, if I’m being totally honest, kind of upset with myself for as much as I can go on and on about trust and the importance of trust in a team at how many things came down to me, not trusting that somebody else can do the job, even though I know that they can, right. And that cognitive dissonance was really, really hard to reckon with people who I know and I love, and I, and I do trust for some reason, there was a facet of that trust that was missing. And I wasn’t really grappling with that. I wasn’t acknowledging that. And so I was keeping things from them, which the, the problem there is twofold. It’s bad for me because I’m doing that. I shouldn’t be doing there’s other, other, maybe more important, more valuable things that we’re doing, but I’m also robbing them of the opportunity to grow and even make a mistake, doing it a different way than I wanted to.

Alex 00:50:40 But even within that is a broken mindset, which is why is that making a mistake? The only way for them to do it differently than me? What if they did it differently than me? And it was better? Am I afraid of that? I don’t know. That’s scary to think about, but like that seemingly simple question of like, why aren’t you delegating certain things that, you know, you should write down this really, really strange. I was about to say wonderful. It wasn’t wonderful, strange rabbit hole of self exploration and going well, shit. I’m not being totally honest about what it means to trust somebody I got to work on that was, was hard and humbling and a work in progress. And I imagine it will continue to be a work in progress, but definitely a pretty intense mindset shift that I don’t think I could have done on my own.

Andrew 00:51:26 Thank you for sharing that. As I was sitting with all the ideas we were talking about earlier, I was feeling like the sense of like clenching in my stomach. And I was like, okay, what is that? I think that one of the other mindset shifts that might be at play here is a letting go of, or trying to let go of the need for certainty, going back to the idea of control and how it, what an illusion it is, right? Like you thinking about these long games of business and the long arc where we’re talking about here, like the reality is we don’t know how it’s going to play out. We don’t know where it’s going to go. And I think on some level we just hate that idea.

Alex 00:51:56 We absolutely do. What’s interesting is like, without wandering too far down, down this path, the neuropsychology of uncertainty, I think tracks back to the evolutionary version of it anyway, of halt from, you know, at a certain point, uncertainty meant death, right? It meant not having enough food to survive the winter and then not having the right protection or weapons to not be eaten by a predator. And we have the same biological response to the uncertainties that are much smaller and far less threatening, at least existentially it’s the same damn the chemicals that get released in our brain and our brain doesn’t really know the difference, how to calibrate. So our overall response of that pit in our stomach, the, the, the dump of cortisol that makes us physically feel that way, or I should say those ways. It, it’s more than one thing that is very, and this goes back to that separating facts from feelings, you’re feeling that way for a reason. It’s because there is uncertainty, but the uncertainty is not potentially life-threatening. The uncertainty is uncertainty and it’s just uncertainty. And if you can verify that is, I am afraid of something because I don’t know what’s going to happen, but the odds of me doing harm to myself or somebody else are near zero, then it’s just uncertainty. And if I do it, I will learn that uncertainty and endanger are not the same thing.

Andrew 00:53:19 I think I need to practice that a lot too. Last one I want to start with right now is just what is a small change you’ve made in recent memory?

Alex 00:53:26 That’s had a big impact of all the changes. I’m thinking of a really big, because quarantine, um, S a small change. So during quarantine, within the indie hall community, people have a lot of feelings and those feelings run a really wide set of rain. You know, it ranges from the doom diving of whatever potentially horrible thing is happening somewhere else in the world, or in our own backyard on any given day to the opposite of that actively seeking safe places to have meaningful conversations that aren’t necessarily directly related to whatever chaos is happening in the world and everything in between. I should say, I’m super proud of the way the Indy hall community has sort of stepped up to that whole range of challenges and treats one another with respect. I think we’re showing precisely what we spent 15 years preparing for right now, this small change I would say is it’s less of a directional change and more of a incremental change in a direction I was already going, which is to fight the resistance, to be involved in every conversation and just kind of let some things play out.

Alex 00:54:32 And as someone who cares and cares deeply about other people, that’s hard as someone who also doesn’t want to be perceived as negligent. It’s hard, but I’ve found two things to be useful. One is my overall sense of calm is much stronger. My sense of the community is hurting. I need to take care of the community tough thing to fight up against, but maybe more importantly, again, it kind of gives the gifts, this group of adults, the room to really exercise what they have been practicing. And so I think it’s been beneficial for, for a lot of folks. The through line of that is it does raise the new question is when part of my role as a leader has been to guide challenging conversations, and I’m taking an active step to maybe not jump in as quickly and realize that there will still be times for me to guide conversations, but folks are now in a spot where they can guide guide each other a bit better.

Alex 00:55:28 What does that create space for me to do? How does that reshape and redefine my role? How does that shape reshape and redefine Indy hall? I don’t know. It’s not a directional change, which maybe is a little bit different from, from the question you’re asking, but it’s a definitely an incremental change in a direction that I think we were already heading that I feel like already seeing, like, I’m not sure I would have done it if we weren’t in this situation where we kind of do need to be a little more thoughtful and intentional about where we put our energy into solving other people’s problems. It goes back to that, you know, the endurance race that we signed up for, we don’t know how long we’re running and the act of self-preservation is an act of love and support of the community, because it means that I can remain available to them when they really need it.

Alex 00:56:14 That’s a potentially complicated, long view way of looking at that environment, but one that I’ve already sort of seen play out. And as I think about the long view of our work indie hall and beyond like we’ve got ten-year aspirations of growing into more of a, an organization that in addition to all the things that we do and have done is, you know, supporting people in career development, career growth, business creation, business growth, and all these things throughout the region. The things we want to do are a lot bigger than a lot bigger than anything we’ve ever done. I’m going to need to get good at delegating. I’m going to get you to get good at making sure that I’m giving the right amount of energy instead of a hundred percent every time, because not everything needs a hundred percent. There are some things that always need a hundred percent, but a lot of things don’t need a hundred percent. They need the right amounts. And then the handoff to make sure that everything has the support that it needs. I feel like the environment now is, is sort of practice for an environment that is, it doesn’t exist yet. And I don’t know what it’s gonna look like, but I know it’s going to be important. So the practice, and maybe the little bit of pain of the practice now will, will hopefully be worth it.

Andrew 00:57:24 First of all, Alex, I just say, thank you so much for being here today. It is an absolute pleasure to talk to you and to get to spend some time in your world. What do you want to leave the audience with any, what requests do you have for the listener, or what idea would you want to leave our listeners with?

Alex 00:57:38 So, one of my goals with the book, and this is not a pitch to go by the book, frankly, you can go read any review on it. And one of the things I’m loving about the reviews is people are pulling out their favorite bits and bites from the book. So if you want to go read a hundred blog posts, you can probably pull together the entire book. I would love for folks to take a little bit of time to sit with the lesson. And maybe don’t not so much, like I don’t care so much. What you think about the lesson. I care about how the lesson made you feel. Um, and if you can use again, the book or their views or anything that we’ve talked about as a opportunity to practice, how a piece of information makes you feel and process that feeling, and that makes you think a thing or make a decision.

Alex 00:58:28 Those are the things that I would really love to hear about. And even if I don’t hear about it, I’m just hopeful that, that, that you can have that practice. If it does do something for you, I would love to hear it. And if it means you do something and there’s some sort of impactful outcome, you made a career shift, you started a business, you grew a business, you had a conversation with your team. You had a conversation with your prospective customers, whatever. Like if you went and did a thing, those are the stories that I really love to hear waking up to, to get an email from somebody telling me about what they did is so much more interesting to me than them telling me what I’ve wrote. I know what I wrote. I care about what you’re going to do with it. So hit me up and let me know what happens next.

Andrew 00:59:11 Fantastic, Alex, thanks so much for being here. An absolute pleasure.

Alex 00:59:14 Thanks, man. I appreciate you being here and for your insightful way of pulling things apart, I was really cool to sort of weave this through the original thread that you started with of our shared interest in, in Buddhist teachings. Uh, did not exactly see that coming, but I’m really, really stoked for what it allowed us to explore.

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