Special Guest: Alex Hillman, Founder of Indy Hall

Len: Hi I’m Len Epp from Leanpub, and in this Leanpub Frontmatter podcast I'll be interviewing Alex Hillman.

Based in Philadelphia, Alex is a marketing communications and community-development consultant who works on product launching and community building strategies through 30x500 and Stacking the Bricks, along with his business partner Amy Hoy, and he's also the the founder of IndyHall, a co-working space in Philadelphia.

You can follow him on Twitter @alexhillman and check out his website at dangerouslyawesome.com. You can also check out 30x500 at 30x500.com, and Stacking the bricks at stackingthebricks.com, and you can learn more about IndyHall at indyhall.org.

In this interview, we’re going to talk about Alex's background and career, professional interests, IndyHall, and about audience building and growing sales, something of particular interest to indie authors, or anyone with a product they're trying to sell online.

So, thank you Alex for being on the Frontmatter Podcast.

Alex: Thanks for having me, Len. I'm excited to be here, and that was a brilliantly comprehensive, and yet somehow so concise introduction of all of the wild things that I have at my fingertips. So thank you, and nicely done.

Len: Thank you for that - researching for the interview I listened to a few interviews of you online, and people usually start them by saying what a challenge it is to interview Alex Hillman and to describe him. And so I sort of borrowed from people in the past confronting this challenge.

I always like to start these interviews by asking people for their origin story. So, I was wondering if you could talk a little bit about where you grew up, and how you first became interested in computers and technology.

Alex: I grew up in a very small town in Pennsylvania, about two hours north of Philadelphia. I was fortunate enough to have access to a computer fairly young. I think we got our first home PC when I was maybe eight or nine - and we're talking beige box in the early to mid-90s. Not everyone had a home PC then.

I had a couple friends that had them before I did, because their parents worked in technology. I had one friend in particular, his dad worked at like a local branch of Bell Labs. That was maybe the first home PC I ever touched, because they were the first friends to have one. And that was more, like, playing X-Wing versus TIE Fighter video games and stuff like that. But I was fascinated by it, and when we got our first beige box computer.

My introduction to computers, that I would say is meaningful to my life today, is - when I broke it, as is wont to happen with any piece of electronics. I had this computer that I used to play video games on and poke around, and it was mostly entertainment. Obviously I was a kid, so I wasn't doing productivity stuff. But when the hard drive died and I couldn't play video games, I was kind of bummed out.

My dad is an entrepreneur himself, and actually paid his way through college fixing other people's cars. And so I grew up around a father who knew how to fix things, and was pretty handy. And so, I said, "Dad, the computer broke." And he said, "Alright, well let me grab the screwdriver from the tool chest." And we go down to the basement, and he looked at the back of the computer, and helped me take the screw - you know, those little hex Philips screws off the back.

And he looked inside and he said, "You know what, son? I think this one's all yours." And kind of left me to my own devices, to figure out what was wrong. And through, like, literally going to the library and reading books, I figured out that maybe that clicky noise was the hard drive, and that lined up with some of the error codes on the computer - and maybe I had a bad hard drive.

And so I went into the local mom and pop computer shop, because that was still a thing in those days - I was probably 10 at the time. So this 10 year old walks in and says, "I need to buy a hard drive." And they looked at me like, "What the heck are you going to do with a hard drive, kid?" And I told them what I had figured out. And they said, "When you get a little older, if you want to come in after school and learn how to fix computers, we'd love to show you."

I'd say that was the most meaningful introduction to computers for me - diagnostics, learning it by trying it, figuring it out - deductive reasoning. I didn't know what those words were when I was nine. But I could kind of reverse engineer - I could remove stuff from the equation and say, "Does that make the error code change?" So I was learning debugging before I knew what debugging was. And that put me on a path to be interested in technology.

I ended up working at the computer shop and selling computers to people - who, for many of them - it was their first computer. Or repairing computers for many people, for whom it was their first computer. And I was pretty good at it.

When I went to college, my thought process was, "I'll get into some sort of IT consulting world, I'll start an IT consultancy. This stuff I'm doing for people at home, I'll do for businesses." And so I went to Drexel University here in Philadelphia, with the intention of getting that education. But also having this co-op program that they run as a big part of - it's the reason I chose Drexel - is the opportunity to learn on the job, not just in the classroom.

And for my first co-op, I got a job at a big bank down in Wilmington, Delaware. Within a few weeks, it was pretty clear that the thing I thought I wanted to do, I did not want to do. And working at a bank was making me pretty miserable.

Len: And you were working in the IT side of things?

Alex: Yeah, IT, helpdesk. And so a lot of it wasn't even - like, the work was fine, it was the people. Doing technical support for corporate folks - who, for a lot of them - the computer was a thing in the way, not a thing that they loved to use. And when it broke, it was probably my fault. So I was not set up to have a great relationship with these folks from the jump.

And so one of the ways that I saved that position was I went to my co-op adviser, my boss, effectively, and I said, "This front line support thing is - it's not that I don't like the support, it's the people are pretty miserable." And she goes, "Yeah, they are." So it wasn't just me. And I said, "I'm still interested in this, but if we could find anything else for me to do, it would be great."

And so she teamed me up with some of the guys that did more like the network design. So I learned things like systems administration - they were a Novell shop, so I learned my way through Novell systems design, and all these other kinds of things. It was a patch - enough to keep me in this corporate thing for the remaining five and a half months, or whatever it was. But I knew I was not going to come back.

It was at my second co-op that I had a friend who was working at a digital agency, and they did business consumer websites. They were doing stuff for Campbell's Soup Company, and they were doing stuff for Motorola, and Sony Pictures Classics - like movie websites. They were making websites where I would actually see the things that those websites would advertise in the real world, and it felt like a very real-world manifestation of technology on the internet.

This is the mid-2000s, and so obviously the internet was a big thing, but it was nothing like what it looks like today in terms of apps and software-as-a-service, and all of those kinds of things. But making things on the internet was a thing. And at that point in my career, for all that I had done in technology, I had done very little programming.

Part of that was because I had it in my head that programming was a mathematics-based thing. And obviously there's lots of that, it is true - and I was more of a language-minded person, and math wasn't it. And obviously, knowing what I know now, they call programming "languages" for a reason.

It was in that second co-op that I fell in love with the internet and being able to write code to make a thing that worked, or was interactive, where you could do a thing, or I could publish something - and then people on the internet would interact with it and use it.

We built one of the first online recipe databases for Campbell's Soup Company, where you could put in one of the Campbell's Soup products, and it would tell you things you could make with it. Or you could put in things that are in your fridge, and it would tell you what Campbell's Soup product you could make with the things in your fridge.

Len: And, and one thing - sorry, I think I should mention. So you said you went to Drexel University. But this whole time when you're at university and then doing co-ops, you were studying Computer Science.

Alex: I wasn't. No, no.

Len: Oh you weren't, oh okay.

Alex: I was not, yeah. I was actually a business information systems major.

Len: Oh, okay.

Alex: No, that's okay. So I mean, my interest was - again, more in the sort of like technology systems, than Computer Science and programming. At least that's how - I know that's not exactly how it's broken down, that was how I saw it in my head. I had a lot of friends that were in the CS program, and Drexel does have a great computer engineering program - but they were all much smarter than me, or I should say "differently minded." But it was the business program - in my head, I was like, "Oh, I'll get the business degree. Because if I want to run a business - I'll learn how to run a business in a business school." And that was a mistake. Because what I realized is that business school teaches you how to run somebody else's business, not your own. And I was pretty sure that I wanted to build my own thing.

And so in that second co-op where I discovered - I had already discovered that working for big companies is definitely not my thing. Making things on the internet could absolutely be my thing. And going on to finish my degree probably wasn't necessary to do the things that I wanted to do, in terms of building my own business.

That was when I made my first leap into the first stages of entrepreneurship, where I was a freelance web developer. Being out on my own and making websites, and little web products for people, was sort of my foray into entrepreneurship. It's sort of a long story to get there - but I'd also say that's a pretty meaningful starting point for everything that I've built today, that I actually still work on.

Len: Thank you for sharing all of that. It's really interesting - so at your first co-op, it was the people you had to interact with that you didn't like. And the second was where - as I understand the story - was where you realized that working for big companies wasn't for you. And I know you've described yourself as "emotionally unemployable", I think?

Alex: That's very true.

Len: ...in the past. I was wondering if you could explain a little bit about that? What is it about - ? I mean, I know that in part working for big companies is - One of the problems that I think you have with that is - not to put words in your mouth, but actually I'm doing that - is to be forced to interact with a set of people, because your boss says so. And I just learned - one of the things you didn't like about business school was, it's training you to run someone else's business, where you're under their command. Is it being under someone else's command?

Alex: Yeah. I think it's a combination of being under someone else's command, or not being involved in the decision-making process, or not having influence over - If I have the means to make something, and someone else decides what I make, is the thing I made actually mine? And if they can make a decision about what I'm making, and that in any way is something that is either counter to what I desire or believe or I -

Now that I've got some more professional experience under my belt - it shows up in a slightly different way, because I have that experience. But nothing is more painful for me than somebody wanting to do something - me knowing that something will not get them the result that they want, and knowing that there's is a better way, there's a predictably better way, not just my way. It's not that it needs to be my way, it's that if your way is not going to get you the result you want - but you're, you can't see anything past your, "This is what I can--" This is - it's often for a short term gain, especially for big corporations.

If the solution to the problem only fixes the short term, but not the long term problem - that really, really tweaks my brain and makes it very, very difficult. And unfortunately in big companies, especially in the last 30, 40, 50 years, quarterly returns or shorter, matter more than the long game. And so I think that's the dynamic that makes me emotionally unemployable - is more that, if somebody else thinks -

There's plenty of situations where somebody else knows better. But if somebody else thinks they know better, but it's only in service of a short term gain instead of a long term gain, I tend to be optimized more for that long term gain. And that schism is always going to make me somewhere between deeply unhappy and wildly unproductive.

Len: I think I'm totally with you there. I actually start like shaking, in situations like that where -

Alex: It's a physical thing, totally.

Len: Yeah, and where it's like, I know - it's not one of those things where it's like, questionable. It's where you just know. You actually do know that what's happening is wrong. And sometimes, for me - that can be if someone's overestimated my capacity.

Alex: Totally.

Len: It's not about me being right and better than other people. It's like, it's just a full existential awareness that what is happening is wrong.

Alex: Correct.

Len: And then when you're in a hierarchy and you're not on the top, you just are - it's, there's this just - it's like a horror show.

Alex: Yeah.

Len: You're just trapped in a nightmare where things are wrong, and everyone's acting like they're right.

Alex: Len, I think you said something that's crucial - it's not about being right. I'm super not interested in always being right. One of the most valuable lessons I've learned as a leader - now that I've got team members and other people that I work with, is - I'm always in service of the goal. I have no desire to be right, in fact it's a blessing when I get to be wrong - because somebody else has a better idea than I had.

But, to your point, when you can see - when you can sort of run the chess game out and say, "I think this is going to be a problem," or in some cases, "This is going to create future problems for me. I would like to protect future me from the problems based on the decisions you're making" - those are the kinds of things that I think you're totally right on the money. Where you start getting this sort of like physical defense, because you are potentially creating problems for future self, and you want to protect your future self from whatever decisions someone else is making now.

Len: Yeah, and future others as well.

Alex: Totally.

Len: And if you're on a mission to achieve a goal, and then everything around you is undermining that mission, what are you supposed to do?

So, you developed a mission. You became an independent developer, and then you became one of the first people in the world to get involved with the coworking movement.

We were talking a little bit before this interview - and one thing I learned researching for this interview, was that coworking is not just a practice, but actually is, as I just said - a movement, with a politics behind it, in a sense, and an ideology. I was wondering if you could talk a little bit about that, from the origins of the movement. How did you become involved in it and why?

Alex: So, we can put a timeframe on this too, I think is a little bit helpful.

I left to begin freelancing - I left my full time job to freelance as a developer in 2006, and was spending a lot of time hanging out in online Skype chat rooms. Actually, it's fun to sit here on a Skype call with you. I don't open it very much these days, but it's a place where I made a lot of relationships, back when Skype chat rooms were sort of in many ways - after IRC, but long before Slack.

There was a group that I had gotten connected to that were based out in the Bay Area. And they were running a consultancy that was doing mostly online community development strategy for some of the bigger Bay Area startups and companies.

They sort of had this philosophy around collaboration as a business value, that predates things like Web 2.0 and online community management. I mean, it doesn't predate them - those things obviously go back decades. But now every company's got some kind of online community, some paid community manager, and so on and so forth. This predates all of that.

But my own personal - I grew up on the internet, I hung out in online forums and chat rooms a lot. And so to meet people who were building sort of a profession around those sensibilities was really exciting for me. And I realized, "Oh wait, maybe within this world of technology, there's this sort of Venn diagram of, "I can work with technology and technology and people, but I can also hang out with and meet cool people." Like, that would be amazing.

And so I met this duo, Chris Messina, and Tara Hunt. Tara's got an amazing background in marketing, and really taking an approach - a sort of a human-focused approach in meeting her customers. All the stuff that we'd look at today, as like the fundamentals of good marketing, Tara was preaching about since the early 2000s.

Chris has got a bunch of interesting bits in his history as well. He's most famous for inventing the hashtag on Twitter, and otherwise.

Len: Oh, that's quite something.

Alex: It is something. For better or for worse, it's something. But the two of them - so they had this tiny consultancy, and they were about to rent their first office for the consultancy. And one of the cafes in the Bay Area, called Ritual Roasters, was one of the quintessential hangout cafes for Bay Area nerds. The startup technology nerds would go and they'd work on their laptops and hang out, and you might bump into somebody who would be the founder of - honestly, Twitter is a great example - or Flickr, or these other early social web companies.

This is where all these people hung out. And on one historical day, Ritual Roasters decided to plug up all of the power outlets, to send a very strong message that they didn't want people spending all day there on their laptops. And so Chris and Tara looked at that and said, "Well, that sucks, your call, but maybe this is an opportunity to create the kind of clubhouse that we were using Ritual Roasters for, but it wasn't intended to be. And since we're going to get an office, we'll just get a bigger office than we need, and make it the new clubhouse for all of our Bay Area friends. And if you want to dedicate a desk, you can pay a monthly fee, and that will help us bring our rent down. But for everyone else, we'll just have a big open table. And if you want to work at that open shared table, you can come and go as you please, no charge."

Other coworking-type-things existed before that. The original coworking space wasn't even really a space. It was a guy named Brad Newberg who was saying, "I'm struggling to work at home as a consultant. I miss having structure and colleagues in my day. So twice a week, I'm going to rent out this yoga studio that's not being used, and invite a couple of other people to come work on card tables. And at the end of the day, we put it back together." But the key there was, "I want to be around other people and I want us to share a little bit of structure." It was temporary. It was kind of pop-up.

Chris and Tara took that idea, and extended it into their clubhouse model, that was a combination of Brad's concepts that he called "coworking" first, with the reaction to Ritual Roasters saying, "Get out of here, laptop workers." I think that was the nexus of energy that said, "Wait a second - we can use this word 'coworking' to describe an act of intentionally being around other people, but working on different things. And allow for the best parts of having co-workers, which is the serendipity, the social bonds, the opportunities to share and learn - but we don't all have to work for the same company in order for that to be possible."

I kind of watched that happen from 3,000 miles away in my bedroom work space in Philadelphia, as a newly-minted freelancer. It was like my eyes were googly and I was like, "How do I get that for me? And, by the way, where the heck are those kind of people here in Philadelphia?" I - again, "I'm a freelancer, I make stuff on the internet. Who are the other people who make stuff on the internet? There's no meetup.com. There's no coworking space. There's no -" Like, cafe culture was barely a thing. Not everybody even had laptops then.

So, "Where do I go to find my people?" I didn't know the answer to that. But it was in finding the answer to that, where I started to connect the dots and say, "Maybe my role here in Philadelphia is to find those people and bring them together, and then adapt what I've learned from watching Chris and Tara form their community, and build our own here."

Len: And so the first thing I imagine you had to was find a space.

Alex: Well, no. That is the common thought process, especially for folks who - today, we're recording this in 2020. But I think the common theme - as coworking has become mainstream, is step one is, you go and find a location. And we actually spent a year before we even really had a conversation about setting up our own space. We were running our own gatherings and get togethers.

One of the first things that we were doing besides just hanging out at the bar and talking shop after our, our workday, or on the weekend - was, one of our crew said, "Hey, a bunch of us work from cafes. What if we all went to the same cafe on the same day on purpose?" Which sounds silly. And today, and people are even building apps to try and coordinate this.

But it was such a critical first step for us, realizing, "Oh, if we create some physical gathering and momentum - a) we have something to invite other people to. But we also build this rhythm and momentum," where working from a cafe is not ideal, in a lot of ways.

The WiFi's generally not very good, there's all kinds of noise and distractions - and you're not really in control of the environment at all. No meeting space. The barista's glaring at you because you've been there all day and haven't bought enough.

Len: And security of your stuff.

Alex: Security of your stuff is definitely one of them - a little bit easier if you're there with a group. Nonetheless, in spite of all of the shortcomings - those days of sitting around each other were better in a really remarkable way, that made us start thinking about, "Maybe there's a way for us to do this more often, and to have our own place, that allows us to come together however we want without all those challenges."

I can even share a funny anecdote of how strange it is to be intentionally in a coffee shop with a bunch of other people. We had a chat room that we'd run during these events, so that people who could not physically join us, we could still hang out and chat with them, and share updates, and extend that in-person social experience to a hybrid online, and in person. And somebody cracks a joke in the chat room - and six people in the cafe all laugh simultaneously, but the rest of the cafe has no idea why.

Those are the kinds of things that are super normal in a coworking space. But in a semi-public space where there's no shared context, you can't turn to the stranger next to you - I mean, you can - and introduce yourself and ask what they're working on, or help them - or ask for help debugging a problem. Like, you can do that, but there's no social context for it. If we had our own place, that's all we would have - is social context.

And so we set out to find a location. We did that together. We took notes about them, we decided pros and cons. There was no decision on a space, and there was no business entity - or even really much branding, until a few days before we signed the lease. And literally the night before the lease was signed, I organized that same crew together at one of our local watering holes.

And I said, "Look, here's all the numbers. Here's the details, here's what it's going to take to make this happen. I don't have a lot of money; I've got a couple thousand dollars to my name that I'm willing to put into this, but I need to know that you all actually want this. So if you can sign up for a couple months of membership, six months of membership, if you can prepay for a couple months of membership - and sign that tonight, bring your checkbook. That will give me the confidence to sign that lease tomorrow." And we had 21 founding members that night. It was their checks that made me confident to sign a lease that I didn't know how to pay for otherwise.

Len: So you built your audience before you started your business.

Alex: 100%. And not just our audience. But I think that one of the different things between coworking and the kinds of online products that folks that - our Stacking the Bricks students, and even folks that use Leanpub - we follow all the same mechanisms. The only extra thing that we've got to do with coworking - that I think there's room to do with other products as well, is we got to involve those early members in the creation process.

One of the analogies I often use is a barn raising. Where a lot of people think, "Oh, I'll go rent an office, and I'll hire the architect, and I'll design it, and it'll be awesome - and everybody's going to love it, and they'll show up." And then they do that and it doesn't happen, and they don't understand why. The thing is, is because some people do want and need a place to work. But many of them also have other alternatives, and there's no reason to choose that particular place to work, because there's no buy-in.

But what we were able to do is have folks play a role at every stage - from figuring out what we actually needed, to where it should be located in the city of Philadelphia. To, what does it need to have on day one, who else should be a part of this? All of those things were community conversations, and on the first day we had an empty room and a set of keys, and we stood there and said, "Alright guys, now what?"

"Oh yeah, we should probably go to Ikea and get some furniture." And we did, and we assembled that furniture together. So like thirteen years later, we're still doing that same thing that we were doing on day one - which is looking for problems and solving them together. It also just so happened that there was a viable business in there. Because that was something that those people not only wanted, but wanted to be a part of.

Len: There are a lot of threads to pull there, in that story. One of the really interesting things you're describing is - I used the word audience, but you were immediately like, "No, it's a community."

Alex: Yeah.

Len: And community is this pretty rich concept, which is - it's people being independent, together, is the way I was thinking of it. I really like that image of the barn raising, where it's not exactly a collective, it's more like a bunch of people who have their own foundation, but come together to do something.

Alex: That's right.

Len: One of the things you write about - and you've been writing about coworking for longer than almost anybody - is that it's not just a place where people come to work; it's a place where people come to be together with each other while working.

Alex: That's right.

Len: And so it's supposed to - if I understand it correctly, the idea is that, in order to be a community, it needs to be people interacting with each other, and that's more than just chit-chat. It's like, "Oh hey, I don't understand how something like this works, but I gather that you do. Can you answer a couple of my questions?" And to make a place where that's normal, to have that kind of interaction, and expect it.

Alex: That's right, yeah. I think that there's two dynamics that are unique to coworking as a business, compared to - really most every other kind of - I should say community-as-a-business, not just co-working.

With most other businesses, you source, and then deliver the value - whether that value is your time, or that value is a product, you still need to replenish it. Digital products are kind of a twist on that, because the replenishment is fairly nominal - but nonetheless.

With coworking and community building, the biggest value I can provide to a new member is all of the other members. And every new member, every new customer - in addition to taking a little bit, they also become part of the value for everybody else. So the more members we have, the more valuable the product actually becomes. Which is a weird way to think about scaling.

Because we very intentionally design a culture where everyone has something to gain, but also everyone has something to give. And the network is - as you said, independent - but understands that there are people here who would give, given the chance. And that you can give when you have a chance. And also, that it's okay to ask, and that dynamic is normal.

The precursor to all of that, I believe, is trust. I think you can track this back to my origin story and those workplaces that were good and not good. The thing that made a great workplace great was a sense of trust among peers, between peers and management, across hierarchy. If people trust each other, they look after each other. They go out of their - there's an aura - it's weird to say it though. There's a sense, when you feel a company has a great culture, a team has a great culture - that's not ping pong and free beer, or it's not even things like going to conferences and talks. Those are the things you do, but what do they create? They create a sense of - people are generous with their time and knowledge, there are people in this room who know things that would be valuable to me, and maybe I get a chance to be valuable to them at some point. And if you can - I know the most reliable way to gain trust is to teach and to share.

And so among the things that we really aim for, is to get people to share little bits about themselves - not just their work. Because we know that once people teach, and share with each other, that the seeds of trust are planted. We have to continue working to nurture them. But once people trust each other, and they trust that their system has their back - the things that people will do for and with each other are infinite.

And I don't mean that in a hyperbolic way, I literally mean, I challenge you to find - to ask me for a thing that I would actually be interested in doing, that I could not do with the access and support of the community we've built. And what's amazing is, that's a thing that I have access to, but it's a thing that every single member of our community has access to as well.

Len: So you mentioned ping pong. And there is a big famous company out there that's in the news all the time - that most people would, that would be their first idea when they think about coworking. I know that you - I don't know which question to ask first. But I know that - a) you have decided not to follow it in the news, and b) you've written about there being three waves of the coworking kind of movement.

And so, I guess I'll ask you first - we're living in turbulent times. The rest of the world is watching the United States with a particular fascination, with respect to news. Why have you made this decision - let's bracket politics - to not follow this big company in the day-to-day news about coworking?

Alex: I think the short answer to that is, because it doesn't help me or anybody else. And most importantly, I'd say - because it's a distraction from the people who I actually aim to serve. And this is a more, it's a life philosophy in addition to a business philosophy, that you have a finite amount of attention to give to things. It's your job to choose. We live in a more distractible world than ever before. That just means we've got to flex that muscle more often.

I watch a lot of folks in every stage of their career - their business, their industry, whatever it is - lose a lot of energy to paying attention to what other people are doing, or are doing wrong. And when you're putting energy that could be valuably helping the people who you aim to help - whether that is out of goodwill or because helping people earns you money - because that's generally how economics work. Every ounce of energy I put into fussing, fretting, talking about, analyzing what somebody else is doing wrong - is energy I could have put into literally anything else. But most importantly in my mind, the thing I actually care about.

So, I'm just extremely - it's not that I'm not paying attention at all. I know what company you're talking about. And I know the big picture. But the micro, the day-to-day - the things that they do - and this is, again, true of any industry. The little things that happen in the day-to-day news - on the arc of anything important, the odds of them mattering are so, so, so low. But they can occupy head space, they can take up time - and that's the one thing we don't get more of.

And so I make it my focus to say, "The day-to-day doesn't matter; I'll look for the macro. I'll look at the long arc. I'm interested in not even big changes, but what those changes mean over time."

Or maybe part of my meta-interest in this becomes - I'm interested in how other people pay attention to things that I don't think are important, and I see that as an opportunity. In coworking, one of my greatest fascinations is how most coworking spaces look basically exactly like each other. They're all crappy clones of each crappy self. Like, they all do the exact same mediocre thing. And then they spend all this time competing against each other in this race to the bottom, where all they can really compete on is price or free stuff.

I'm not interested in that game at all, and instead I'm interested in that they are playing that game, but I also know that that game doesn't affect me in any negative way. Them doing it wrong has no impact on me, certainly not any negative impact on me. It may have some positive impact on me - in that if they're all doing the same thing incorrectly, then I just need to stay the course and not lose any time or energy to whatever they out there are doing.

Len: And this "they" that you're describing, I think that maps onto the second wave of coworking that you wrote about in a blog post, I don't think too long ago. And so I was wondering if you could talk just briefly about what those three waves are. I just found it so fascinating to - again, as I said - like, I was one of those guys who thought he knew all about it, and discovered he knew nothing when you start reading about it.

Alex: Well it's cool. I'm thrilled that you took the time to dig through, and I hope something in there was useful for your approach, to whether it's coworking spaces or just coming together and work.

I was describing those early days of coworking with Brad Newberg and his pop-up coworking at the Spiral Muse, and then the Operation Citizens Space that Tara and Chris and some friends set up. And then we set up Indy Hall in Philadelphia, and then there was a place called Office Nomads in Seattle, and there was a place in New York City called New Work City. And there are many, many more.

But these people were - a) my peers and my friends. We were all coming together online to share what we were doing, to ask questions of each other. We were kind of - you mentioned earlier that coworking was a movement. The early movement was not, "Hey, we're people setting up offices." It was more, "Hey, we're people who feel like the options that we have for finding other likeminded people when we don't have an office that we have to go to, are slim. Maybe there's an opportunity to create these third places, these clubhouses and that would be a way to make our local communities better in some way?"

That was the common thread. How you did it wasn't super dogmatic. It was this open source approach to something that wasn't software. I gave away everything I was doing and learning - rather than patenting it, licensing it. I've been trying to give away the good stuff for close to 15 years, and people will actively do the opposite.

But that first wave coworking - myself, my peers, and a bunch of other really pioneering folks in this coworking world - the thing we all had in common, was we were all figuring it out together. There were no rules. And if we got something wrong, that was okay - and we all got to learn from it. If we did something right, that was amazing - we all got to learn from it.

And no one knew what coworking was, no one cared what coworking was. There was a period in time where I had a Google Alert for the word "coworking", which - today, would be like trying to set up a Google Alert for the world "programming". Like, that Google Alert would not be useful. But there was a point in time where it was useful, because a new person would write about it - and now I'm connected to another person through this nascent concept. And that person might be literally anywhere in the world, because that's the beauty of the internet.

So that first wave of pioneers - sharing, growing - a handful of us are still around doing our thing. Second wave came along - most noticeably to me, in like 2010, 2011. I was at a coworking conference - that's another thing that happened along the way, is we started wanting to get together in person.

So, I was at a coworking conference in Berlin, and it was the first time where I looked down the room and I was like, "There are an awful lot of real estate people here." The same people who would say, "Coworking, what a cute, silly little concept," were now coming to our conference, and were now using our language - and our concepts - at least in a surface level manner of speaking, to sell their buildings. To sell their real estate. To sell their architecture and design and furniture. They were selling all this surface-level stuff, but completely missing all of the underlying human and emotional dynamics that actually made the experience valuable.

But it also kicked off this second wave - as you're describing, of people who - and I think this is true of any new technology, if you're willing to think of coworking as a technology. There's the first wave people who figure everything out, and there's the second wave people who blindly copy it.

And I think every programmer that has tried out a new framework or been forced to try out a new framework, understands what I'm talking about. Or any time a new concept is popular - some book popularizes it, or some speaker popularizes it. We know what that feeling feels like. Where all of a sudden, everybody is blindly doing the thing without thinking about why they're doing it. And second wave coworking was absolutely that. It gave birth to some of the mega corporate chains, tons of funding floods into this space.

A lot of the early folks - including folks who weren't running spaces, but people who had become kind of enamored with, and maybe I would argue - are romantic about the soul of coworking - now calling for the death of coworking, because it's being used by Regus corporate offices and blah, blah, blah, blah, blah. I had some of those emotional responses too, I'd be lying if I said that wasn't true.

But I also took a big step back and I was like, "So what? Their version sucks. And my version's really good - our version's really good. So what if we just keep doing our version and let them burn themselves out?" And that has, that arc, I think, has largely been playing out. There's a lot of big players. Most of them don't make much money. Most of them lose money. And one of them in particular, famously loses lots of money. But that's the nature of that beast.

There's a third wave of coworking though, that I've seen more of in the last couple of years. And again, to just map this to other industries that people might be living in, if they're not in the coworking space itself, where you go through that first wave of pioneering, you go through the second wave of blind copying. And then there's a third wave of people who kind of watched the first and second, and said, "Well those first wave folks had some really good ideas, but maybe they were a little too idealistic. Does it work at scale? Right? Sounds like a great idea, we'll see how it works in practice."

But then they also watched the second wave come along, where people just blindly copied it, and they said, "Well, if I was going to do this, I'd want to be a little more practical than those idealistic first wavers. But I'd also want to be a little more grounded than those purely opportunistic second wavers." And somewhere in the middle, I think you get an opportunity to learn from both and create what I'm defining as this third wave coworking, and something that I've noticed over the last few years - more and more operators, when they reach out - because I've been writing about this so long and I'm active in the community - I hear from people from all different directions, through every single inbox I'm willing to make public. And more and more people are looking at this and they're thinking - they're thinking. They're doing their research. And they're willing to invest in the time to do the homework, the education, the resources, and the knowledge that maybe are locked up in these other people.

Because I think people - I think there's a future of coworking that is not futuristic at all. I think it's a very human-scale thing, that's kind of the beauty of it, that people are discovering is both a powerful tool for productivity, for happiness, for building local communities, for improving people's lives in cities, for improving people's careers and paths - whether they choose independence or remote work. I mean, this is a massive piece of the remote work puzzle, I believe, as well.

Not that you need to work in a coworking space every day, but to have a place to go to be around other people who aren't part of your team, I think, is a really valuable emotional tool to combat some of the isolation and disconnection that comes with being remote.

Len: Speaking of all that - sorry to interrupt. But I think the really important point that you're making here is that - the big company, and the other big companies in the coworking space actually aren't competitors for institutions like Indy Hall, because what you're doing is much more than just providing furniture and space.

Alex: That's right. And also - we go after a completely different base of customers. Like, the people who want a desk - that they don't have to think about whether or not it's going to be available or not when they travel from city to city. That makes sense, that's they want and need. But that doesn't solve the same problem.

What problem we solve and for whom we solve it, it is extraordinarily rare that we would effectively serve the same customer - or, more importantly - that the same customer would be happy at both.

If anything, we get a good number of people who say, "I had a free three month trial," or, "I got locked into a six month contract - the pitch was good. But the product isn't really what they said it was. And nobody really talks to anybody. And it's kind of cold and sterile, and I'm wondering if there's other options out there that are warm and inviting, and maybe full of people that I have things in common with or could build bonds with."

We get to be the thing that they're selling, but not delivering. It's not a primary channel of new membership, but we hear it on a weekly basis. People - new members, prospects coming through and saying, "Yeah, I've spent time in other coworking spaces, and it's just not right for me. But this sounds different and I want to see what it's all about."

Len: And you've managed to scale quite successfully with Indy Hall. I believe you started at a few 100 square feet and now you're at something like 16,000?

Alex: Yeah. I mean, our first location was around 1,500 square feet, like about 20 desks - or I should say 20 people could work simultaneously without being in each other's laps. And yeah, we're tens of thousands of square feet. Our capacity is - I mean, we're not even - we could add more work space within the physical space we have. But last week we had one of our busiest days ever. I want to say we had like, 200 - 180, 200 people here. Something like that.

But more importantly than that even, is the majority of our members almost never come here. Our online community is actually - in some days, many days - more connected and vibrant than the physical space. And through a Slack-based chatroom and an email discussion list, when you're a member of our community, you've got a place you can come and have access to likeminded people. But you can do that from your pocket, because you've got a smartphone.

And that means that people, most of our members, are here once a month or less. And a large number of them are here basically never, but are quite active online - whether that's because they have a corporate job and they see us as a direction that they'd like to head. We're some inspiration for them to leave their job and go independent. Or they're people who have moved away, but want to stay connected to the community.

Or they're people that have corporate jobs - or even, they're entrepreneurs who have an office somewhere else in the city, but they want an alternative to those coworkers, I should say. I don't want to say they don't like their coworkers, but a change of scenery can be really valuable from a productivity and creativity standpoint. And sometimes it's just nice to be in a place where everyone else is getting work done, but it's not your fault if they're not. And so there's a lot of reasons, yeah.

Len: Just to go into the weeds just very briefly. For anyone listening who's now all fired up about how, "I'd love to have a place like that in my city, and how can I start one?" Can you talk a little bit about the details of your membership model?

Alex: Our membership model is fairly consistent, from the very beginning. Because again, we had those members before we had a business. And so I was able to talk to those members, "If there was a place, how often would you want to be there? And what would be valuable to you?" And in that early membership, I mentioned 21 members. Only two of us were full-time, and I was one of them. So the idea that people will want a desk to work at, totally not the game. But lots of people wanted to know that there would be a place they could go if and when they wanted to - and that the people that they know and like would be there.

So we built our model around that. And our membership model actually starts at between $20 and $30 a month, for people who really just want access to the online community, or if they're here in Philadelphia - or I should say - and if they're here in Philadelphia, the physical in-person events, and discounted access for our day passes, and things like that.

And then the rest of our memberships run between $30 and $300 a month. The only difference between them, they all give you the same access to everything and everybody. We don't charge extra for meeting rooms and all those kinds of things, all-inclusive. The only difference is how often you're here. So we've got a membership that is - like I said, once a month. We have one that's six days a month. We have one that's roughly three days a week, and another one that's full-time with a dedicated desk. All under and around $300.

Which means, again, with a basic membership, for instance - that $30 a month gets you one day of coworking, but all of our online stuff. For 30 bucks a month, or roughly $300 a year, not only do you have a place you could go to get out of the house, or get out of the cafe, or get out of the office that you have, and be around other people. But every day of the week you have access to a wide network of networks of people in different industries, disciplines, backgrounds, from different places, with different stories - with different past, present, and future lives - and the networks that they bring with them.

And that's the superpower I was talking about earlier. All these people who, once you've taken - done a little bit of work to - that we guide people through to earn and build trust. The ability to send a message to that list and say, "Looking for help with x," or "I'm trying to figure this out. Does anybody know whatever?" And it starts becoming, like, weirdly general purpose but also - it's not like a public space like a Craigslist or something like that. It is still very intimate, in spite of giving you access to hundreds of people.

And that membership model, having less focus on desks and no focus on private offices - we have no private offices - is what's allowed us to grow, scale, be resilient. And not focus on putting butts in seats, but instead - bringing people into the community, helping them build that trust. Because again, having that trust is the value that you get.

Len: It's really fascinating - just to bring up a concrete example of how this works. Let's say you've got a startup, and you want to start a podcast, but you don't know anything about it. If you're in a community like this, you can just fire out a message and you'll find people who can do it for you.

Alex: Not only that, but the podcast studio that I'm sitting in right now -

Len: We're broadcasting from Indy Hall Studios.

Alex: Yeah, Indy Hall Studios - live from Indy Hall Studios. Today we've got a pretty nice set of gear that members can use. But early on it was exactly that. It was a member saying, "I'm thinking about starting a podcast for my business. A) - has anybody done that? B) If I were to do some research on the technology we need, does anybody want to chip in?"

So the first versions of the stuff that we used, Indy Hall didn't even buy. A bunch of members pooled their money, bought their own stuff. And then as more people used it, I realized, "Oh, there's momentum here. Now there's a clear path and incentive for us to get even better gear. And that can become a resource that other people can use."

But to your point, even with the studio that we hav,e and all the gear that we have - the thing that we've done to keep it aligned with the Indy Hall mission and mindset, is when you join - it's not - I mean, yes - you get a certain number of sessions in the recording studio. But the real value is a network of other people who make podcasts. Whether they are hosting, whether they are doing technical editing, whether they are using it to market a business, or a product, or a service, whatever it is.

And so building a community around the practice of podcasting differentiates - there's other places in the city that have literally the exact same equipment. I know because we've made the list of what equipment we use public, and they copied us. But people will still come here. Not because of the equipment, but because of the other people who use that equipment - and having access to those other people is the unique value that I can offer, that no one else can copy.

Len: And just before we move on to the next part of the interview where we - I know for people listening, we finally get to the point where you meet Amy Hoy and you guys started doing things together.

But you've got a very deep commitment to the issue of working and how people work together and productivity. And one expression of that is your 10k Independents project. And I was wondering if you could talk a little bit about that? There's another big company that played a role in that story.

Alex: I'm happy to talk about them. I've been running a business for 15 years now. And once in a while, you need to take a step back and say, "What are we doing here again?" Like not, "What do we do?" But, "Why are we doing it?" And just try and re-calibrate that north star, and all those things that I described in the origin of Indy Hall, and that - it was hard to find the sense of community I wanted.

Not only do we have it here in Indy Hall, but it exists throughout Philadelphia for so many other communities. We have an amazing startup community. We have an amazing music community, an amazing food community, an amazing arts and bar - there's so many amazing communities that were so hard to find a decade ago, that are easy to find now. And so the problem to solve looks a little bit different.

I had a bunch of disconnected ideas that kind of galvanized when I watched cities - including Philadelphia, across the country - compete with each other. I should say against each other - for the privilege to give Amazon massive tax breaks and build a second headquarters in the city, in our city. Philadelphia did end up being a - we entered into that race - not myself, personally, but our commerce department did.

We were a top-ten pick. I firmly believe that we never were actually a pick, because I think that Bezos knew exactly where he wanted to be, and he used this entire game to just get amazing deals from these cities. But that's about as conspiracy-theory as I'll get about it.

My big takeaway from the whole thing - knowing, well, we didn't win. Or I should say, we did win because we didn't win. I was fairly confident that any city that does get this, it's going to be negative for a lot of people for a long time. I saw two things.

One was I watched our business community collaborate to speak kindly about our business community and our city for the first time in a long time. Not that people always - I mean, sometimes people do talk down on, "Why would you run a business in Philadelphia?" But more importantly, it was players that actively do not get along, were willing to be part of a co-ordinated message to talk about how great it is to run a business in Philadelphia - or how great it could be. And I was like, "That's interesting. Maybe we should issue these challenges more often. With maybe fewer stakes that are risking displacement of our most vulnerable populations and such?"

But the other part of it was the promise. The offer from Amazon was not that big. It was 50,000 jobs. Which is not nothing. And for a lot of cities across America, it's actually quite significant. But for a city like Philadelphia, it's the sixth largest city in the country - 50,000 jobs is a drop in the bucket. And they're not jobs for the people who need those jobs the most. These are not replacing - they're the white collar jobs; this is a blue collar city.

So the deal, as much as it could be, had to be a bad one. Because Amazon's getting tons of benefits, to bring, in my mind - only 50,000 jobs. And so my takeaway here is like - if the number that makes city hall and everyone else do backflips, and puts Amazon in the news nonstop for 18 months is, "I'm bringing 50,000 jobs to your city," well, guess what? I'm bringing - I, Alex Hillman - am bringing 50,000 jobs to the city of Philadelphia. How do you like them apples?"

And it's not just a hyperbolic pitch. I believe there's actually a way to do it, and do it in a way that maps to the strengths of Indy Hall - and in a way that makes sense in the next decade, in modern time. And the short version of a much longer pitch that you can go read at indyhall.org/10k - I say longer, it's like an 8,000 word diatribe. So enjoy. It's a fun read, I hope - but I think will color this with a bit more detail.

The path that I've drawn is not to create 50,000 jobs by installing them in the city like we're used to from the previous generation, the Industrial Revolution. Jobs came in factory-sized packages, company-sized packages, where 50,000 jobs was a kind of package that cities would compete for and try to earn.

But today, companies don't start with 50,000 employees. They don't start with 1,000 employees, they don't start with 100 employees. Most companies don't even really start with ten or five. More and more companies are starting with one.

And the internet is this incredible lever that makes that possible - to be a single person who puts value into the world and earns a living from it. It's the most incredible thing. Leanpub is a part of that ecosystem. The things you do for your authors allows people to - through individual product services or a portfolio of all of the above, to create an economic advantage for yourself. And then, if you choose down the road to scale that - to start creating economic opportunities for other people: jobs, right?

So my path to creating 50,000 jobs in Philadelphia is to first help 10,000 people sustainably create a job for themselves through paths of independence and entrepreneurship. Which may not look like starting the next Facebook or SaaS app, and instead may look like starting a very straightforward service-based business. Whether that's a local business or an online business does not matter. But that business makes it so that you don't have to go back and get a corporate job.

And then once you've got that business stable, once that business - once you not only learn how to create the thing, but also how to sell the thing, how to market the thing, how to build systems around it, how to actually run it like a business. Then you - the analogy I've been using is, "Once you put on your oxygen mask, then you can start helping other people." Just like we've heard thousands of times on an airplane.

I think economic advantage works the same way. If we can help 10,000 people build an economic advantage for themselves - create a job for themselves that allows them to not just cover their bills, but save for retirement, afford healthcare, go on vacation - a job that is equivalent to or better than what you could get working for somebody else. Giving myself ten years to create 10,000 of those - and this is not an Alex Hillman goal, but a Philadelphia goal.

The work I do with Amy, we've already done that for 1,000s of people around the world. If I laser-focus part of my energy on doing that in Philadelphia - and then also doing it for people who are not already in a position of skill and privilege like programmers, and technologists, and designers - we've got to teach other people some of the core skills first, before we can teach them how to build a business around it. But we can do that. In a lot of ways, it's bringing the work in the world that I've done with Amy for the last decade, and the success we've seen there home, but also making it available to more people through the lens of, "Maybe you think entrepreneurship isn't for you because the word entrepreneur looks a certain way? And whenever you see someone described as an entrepreneur, you go, 'That's them, not me.'" I want to show people that entrepreneurship looks like a lot of things that are not Mark Zuckerberg, that are not venture-funded unicorns - and are not even apps and technology. Those are just one category that happens to be in the news way too much.

Len: So you've handed me the perfect podcast interview segue -

Alex: Excellent.

Len: Into the next part of our interview. Can you talk a little bit about the origin story of your collaboration - your very successful collaboration, I should say, with Amy Hoy - and what you've been up to for the last 10 years together?

Alex: Yeah. So, I mean - the origin story, I was at South by Southwest Interactive in Austin, Texas in 2008. And - it was either 2007 - which was my first year, or 2008. I feel really bad not knowing which, but one of them. I had blown out my voice from talking to too many people, and I was standing in line to get a cup of tea at the Starbucks in the Austin convention center.

And it turned out that I was standing next to the CTO of Pandora, named Tom Conrad. We were just chatting. And I was like - that was one of the cool things to be at South By, was to just chat with cool internet people. And on my other side was this woman named Amy. The three of us chatted for as long as we were in line for tea - and then Tom peeled off and Amy and I kept walking and talking, and we became friends. That's the truth of how we met and how we came together.

It teally wasn't for another couple of years - her and some friends came to Indy Hall's opening. It had to have been 2008 or - I'm sorry, no, it was 2007. Because then she came to the Indy Hall opening, in late 2007. That's right. So her and her then boyfriend, now husband - came to Indy Hall's opening. I went to visit them in Vienna when they moved in together.

And one of the things that Amy and I would consistently commiserate on, was how I had started this Indy Hall business as this unexpected spinoff of my freelancing business. She had much more intentionally built a SaaS business to escape her consulting business that she hated. But the common theme we had was we built our audiences and communities first. We listed diligently to what those people actually cared about. We took the time to understand them and how to communicate with them. And then we built stuff that they would actually pay for.

Meanwhile, a bunch of our friends who were equally skilled in craft as designers, developers, writers, whatever it is - hop from startup job they hated to corporate job they hated, to another startup job they hated, and then occasionally going to raise a bunch of venture capital to create another job they would hate. And none of them would examine all of the white space in between those options, some of which looked like the things that Amy and I were doing.

And we said, "Why is that?" Or, "Why is it that when people do choose to try and bootstrap a business that it appears too hard, or that they do the wrong things or in the wrong order?" And in their apartment in Vienna, Amy and I did a real-world Trello board with a bunch of Post-it notes, brainstorming, "Where are all the people - where are all the ways people screw this up? Why aren't more of our smart, talented, creative friends building old-school, simple businesses, using the levers and power of the internet? Why aren't they -? Why is it that it's either a startup or a corporate job I hate, or a world-changing venture funded rocket ship? What are they not seeing?"

And the only other piece of that story that I glazed over, is actually - Amy had enough success with her software-as-a-service, that people were kind of following along with that process. And she offered the ability to join her for a three-hour conference call for $99. And she would go through - not just the origin story, but also like, lessons learned along the way. "Here's literally how I launched a software-as-a-service in 2008 or 09," I think it was, "And how I launched it, so that I had paying customers on day one."

Which - for a lot of programmers, building a software tool was easy; having customers on day one was a pipe dream. And she was like, "I did it. We billed a couple $1,000 on day one. Not enough to replace our consulting income, but a pretty solid day one, and enough to give us the confidence to keep going." Nine people signed up for that initial conference call. And all of them said, "We want more."

That was when she came to me and said, "What do you think about taking what we've learned to create a road map to teach other people the things that are somehow not obvious to them, because they're steeped in the other narratives of how work and business creation happen - and show them that there's another way, and let them choose it?" And so, over the last decade, we've evolved from that three hour phone call and our - soon after ,our initial curriculum - to what is today the like fourth or fifth major revision, but is a course that is a combination of exercises, lessons, practice, and guided implementation, to help people with no audience whatsoever. And not even really knowing what they could create of value for the internet.

We take them from figuring out who they're best suited to create things for, and how to reach those people, how to build an audience if they're a nobody - if they're not a nobody, how to leverage the assets they have, to build an audience that would actually buy things from them.

And then lastly, and it's strange to some people that this is last - then figure out, "Well, what would those people buy from me?" And use the research-based approach that we've created over time, and some very specific methodologies that Amy has pioneered, to use actual data and insights to drive the beginning of a business.

And so - yeah, over the last decade, that business has grown and evolved. Last year was our best year ever. We had hundreds of students through the program last year alone. We've had thousands of students over the course of our history.

Some of our biggest stories are very exciting. Folks that your audience might be familiar with. Things like egghead.io, which is a very popular programming screencast library and subscription. Joel Hooks, one of the partners, is an alumni of ours. Brennan Dunn has a very successful business in helping freelancers grow their business. And then a second, very successful business that's a SaaS helping marketers use quizzes and surveys and things like that, to progressively profile them.

But besides the big successes, we've also got lots of really awesome, quiet, smaller successes, of people making an extra $10,000 to $50,000 on the side of a full-time job. Using the exact same techniques, doing the work in their nights and weekends to make that extra money to pay down their mortgage faster, to go on that extra vacation, to buy their kids stuff they want - or to save up enough money for the cushion to leave the job that they hate, so they have more time to spend with their family, or doing what they really care about.

So those successes, I'm very proud of the whales that we've been able to contribute to. But the many, many folks who quite literally have changed the way that they spend their time - in ways that allow them to spend time with their family, or doing things that they love, are the ones that I'm most proud of.

And it's interesting, because most of them are people that you've probably never heard of - but they're doing the thing, and we're super proud of them.

Len: Yhank you for putting it that way. I know exactly what you mean. That's exactly how I feel about my work with authors at Leanpub. We've got - a few people have got some Lambos, and that's fantastic. Partly it's fantastic because their success comes from reaching and helping lots of people develop their own careers, because most Leanpub books are about tech, and learning how to do new things.

But the ones that are more numerous are the ones where it's like, "Well, now I can pay down my student loans. Now I can pay my mortgage. Now I can - yeah, go on a vacation or buy a car, even." Things like that. Those things change people’s lives too.

And it's - in particular it's building an audience of people whose needs you can genuinely address, which is where this whole discussion gets kinds of meta. But that's such a wonderful mission to be on.

One thing I wanted to ask you about is - so just, for people listening - so that the people whose needs you and Amy address are typically people - well, not necessarily typically, but one subset of them are people who've had a "fuck this" moment. I was wondering if you could talk a little bit about what a "fuck this" moment is?

Alex: So lots of people - Well, let me back up a little bit. Change is hard. That's a perennial truth, and I think it's part of the human condition. And I think a subset of that is that people don't really change. The harder the change is, this is more true. But even when it's relatively small, most people don't - won't go through the pain of change - unless the pain of not changing is bigger.

And when it comes to starting a business, there is so much that I believe from now observing it thousands of times over many years - there's so much more unlearning that needs to be done than learning. And it hurts, and it's difficult. And that's in addition to the actual work. Which - I think you can be methodical and strategic, and it can be less painful and hurt less - and if you're doing a good job, doesn't have to hurt at all. It's still going to be work.

The trick though, is that we've seen lots of people show up with exuberance and motivation at the beginning - but as soon as it gets hard, it's now a juggling act between, "Well, do I want to do the thing that's hard, or do I want to do the thing I know how to do?"

And this is one of the strangest, most counter-intuitive lessons I've ever learned in this entire process of becoming a teacher of adults - is that the better at the thing that somebody typically does - so, again - let's say the person, one of our students is a programmer. That's what they do as a profession.

The better they are at the thing they do as a profession, the harder it is for them to be a total newbie and suck at something else.

So they sit down to learn marketing or research or copywriting, or any of the other things that are needed in order to be successful - and because they're not instantly good at it, they freak out. And the longer it's been since they were bad at something - which everybody is when they start something truly new, everyone's bad at it. But if it's been so long since they've been bad at it, they internalisze being bad at it as - instead of, "I'm bad at it and can get better," it's, "I'm bad at it, and therefore I'm bad." And they shut down.

I don't want to be too light-hearted about it, because I think it's a serious psychological game. But the point of a "fuck this" moment, is - as Amy puts it in an article that folks can find if you Google, "fuck this moment Stacking the Bricks." The way she describes it is, something happens in your current situation where you throw your hands in the air and say, "I cannot do this any longer." Not, "I don't like this." Not, "I wish this was gone." It is, "We are done here."

And that could be so many different things for so many different people. We hear everything from a boss that passes them over for yet another opportunity, to misuse - abuse of time. The stuff you and I were talking about earlier in this conversation, about people just making decisions that don't make any sense.

A very common one for creative people is projects that never see the light of day. "I put all my work into something, it gets to 90% and then the company just decides, 'Yeah, we're not going in that direction anymore.'"

All kinds of things cause that. Or personal things at home. Like, "I missed another important milestone with my kids. That can't happen again." Or, "I come home exhausted, and that makes my significant other upset. That can't happen anymore." Those are the kinds of things that get people fired up. And what we challenge people to do is capture that moment. Write it down if you can, and keep it visible and present for the moments where maybe it starts feeling a little bit easy - and then all of a sudden it gets hard again, and you have that moment of like, "Man, I'm just going to go back to what was easy."

Look at that "fuck this" moment and say, "No, that's what I stand for now. That's what drives me." And it doesn't have to be a big thing in order to be a real thing. Size is not the goal here. It's the way it emotionally lights you up. And if you can tap into that emotion and use it for good, instead of to drag yourself down, or spend time wallowing or upset - use that energy to create for other people who would value your creating, or just to put good into the world in general. I feel like that's a critical early lesson to learn, regardless of what you're going to put that energy towards.

Len: That really resonates, I think with my understanding of the deeper mission that you and Amy are on.

And so the origin of the name, 30x500, I think is that - you mentioned the wonderful power of the internet. The inspiration is - there's someone who's like - maybe they haven't quite had the "fuck this" moment yet, but they've come close a few times. But they're nervous about change or inhibited about change in some way. And then if you can say to someone, "Hey look, if you can find 30 people to pay you - 500 people to pay you $30 a month -"

Alex: That's right.

Len: "You can make $180,000 a year."

Alex: That's right.

Len: And one way to do that - so the typical way I think people get involved with putting something valuable into the world and making it, and improving the world for people - is they have an idea, and then they try and find people for that idea. But your approach, I think, is that - if you want to introduce something into the world, of course it should be something you ultimately can do well. But what you need to do is find a group of people who have a need that you can address.

Alex: That's right. That's very, very right. And the other thing - I was out for drinks with somebody last night who said what you said in a way I hadn't heard it before. At least not to this particular framing. I thought was really impactful, so interesting to hear.

He's in his first year of being an entrepreneur, and he's more - he comes from the non-profit space. So just to like remold his brain from non-profit to full-profit entrepreneur, is fascinating in and of itself. And he's now looking at the shift from services and contracts into products and productized services, and things like that.

He has been doing his homework and reading our stuff. And he said, "About that idea of, if you just find 500 people on the internet, you're good." He said what that did for him was, he realized - you don't have to - it allows you to erase from your brain, the worry about - are they even out there, right? For him, he said, "I don't have to worry about whether or not there's 500 people out there, because of course there's 500 people out there."

The world is so big. The internet is so big. You may have to do a little work to find them. But the obsession with finding the perfect niche, the perfect - people that create this like magical avatar of a fictional character to serve - there are zero of that fictional character, because you made them up. You might get lucky and match. But once you realize that there is an extraordinarily high likelihood that on planet earth, of the people who are connected to the internet - that there are 500 people who you could figure out if you absolutely had to - how to reach, how to connect with, how to earn their trust, how to help them, and how to make a sale.

Every professional - I truly believe this - every professional can do that. The internet is big enough. And the fact that the number made him realize, "I don't even need to worry about who they are. Immediately, I just - in order to have the confidence to know that they do exist." None of our students have ever said it that way, so it was really interesting - and I'm actually thinking about how we can reframe that, as like, "If you are willing to admit that it is possible - and more importantly that it is extraordinarily likely that there's 500 people in the entire world who match these criteria, then you can stop worrying about whether or not they exist - and just focus on finding them, helping them and creating things they want."

Len: Before we go onto a discussion of some of the practicalities about how to do what you and Amy teach people to do - you have had to do some learning, I gather, in the last couple of years. Because Amy's had to pull back a little bit from the business. And I was wondering if you could talk a little bit about how you've managed to grow it in the meantime.

You said you just had your best year. How have you addressed -? What's the nature of the challenge, and how have you addressed it?

Alex: Well, that's such a good question. So, Indy Hall, the business we spent most of the first part of our conversation talking about - is a business that, in a lot of ways, I am the face of. People aren't buying me as the product, but there's a good chance that if you know about Indy Hall, you know that there's this Alex Hillman guy associated with it. And it's fine, it's not why I do it - it's just part of the dynamic and it's cool.

With Stacking the Bricks, most people know Amy's name first. And that's for a lot of very good reasons. This audience that we work with, she very much started building long before I was involved. That's how she sold those first nine seats on that conference call. She also has written and contributed far more public-facing articles on our website and our newsletter. And so people sign up and they expect to hear from Amy. And all the emails that we send are signed from Amy.

A lot of people don't even know that I exist, unless they happen to read one of the articles or emails that I'm either mentioned in, or I actually wrote, and then Amy introduces on my behalf. Or, they buy something from us, and then I show up all over the place. I'm very involved in the products. But our public facing persona is very Amy. And she and I have talked a lot about that challenge, and some of that is practical. Just like, she's a much better writer than I am. She's just done more of it.

But we have a shared goal, that - the people know me, but also know my contributions to any which thing that's going to be a net value for the business. When we teach together, we create more value. So when we run the rest of the business together, that should be true as well. It's a tricky thing to shift from, though, when people are used to it. And in all honesty, even that we're used to it. It's just like some habits to break.

And the other dynamic that is worth knowing, is that Amy suffers from a number of chronic illnesses that affect her energy levels, her ability to think and work - and it's not that she doesn't want to. Just a lot of days she wakes up and she literally can't. And that's been part of the dynamic over the years.

On the flipside, there's been times where I got pulled into other parts of my other businesses, and I couldn't do the work that I was committed to. And so we've had opportunities as business partners to correct for each other in various ways, that - there's a whole other conversation about partnership that I would love to have someday.

But in the context of this conversation - in the beginning of 2018, Amy had taken some time off at the end of the previous year, to recoup from some health issues. But our plan was to do our opening enrolment of our flagship course, 30x500 - in January, as we typically do. She typically leads the writing for. We build the strategies together, but - again, it's Amy's voice - so Amy does a lot of the writing. And she's like, "Man, I'm still too sick, I can't come back to work yet."

And I was like, "You know what? I have an idea. We've launched these products so many times. We know what we're doing." Most of our launches, we wrote and executed once - and then never again. Like every - we came back to launch again, we created an entirely new series of content and messaging and emails and answering questions on all those things.

I said, "While you stay in bed and get better - I'm going to take a crack at digging through our archives, looking at what performed well in the past." My goal was to kind of build a greatest hits launch, where I'd look at the emails that we sent to launch the same course. We've already built it once, it's like any other - the product is done, it just needs to go through the sales cycle.

I built out our sales sequence using past emails, and then some of my own editing. So, removing things that don't make any sense. Sometimes it's Frankensteining things together. Sometimes it's taking things out that - now that I haven't seen that email in three years - but now I'm looking at it going, "Oh we know how to make, we know how to say that better. I know how to articulate that better. I know what's going to resonate more."

So, Frankenstein-working a bunch of my own stuff, in between glue all of the core pieces from Amy together, run that launch - and we smash our sales records for 30x100 that launch, while Amy was sick and could not write a single word. And I was like, "That's interesting." And so, then the question became like, "Can I do it again?" And so we try to launch three to four times a year. So a few months later, I tried it again - and we hit some great numbers again.

Amy was still pretty sick, and I was like, "I'm going to keep doing this, until you tell me to stop, or until we run out of material." And along the way, I was like, "Wait a second, I'm just doing this for launches, we've got all this other material that's super good, but we don't send emails consistently when we're not launching - which is a problem that I think everybody who sells digital stuff online - we know we're supposed to have a newsletter, we know we're supposed to keep it updated with fresh content and new things to keep people - not just keep people on like a content treadmill. Make sure when somebody gets used to hearing from us, and gets value from the new stuff we send them week after week, month after month - it makes the sale make sense, because they trust us. The stuff we've given them for free has been really good, so the paid stuff is likely to be even more valuable.

And so after I did the second launch, I started going back through our content archive of blog posts and emails that weren't launch-related, and building out an automated sequence of that. So any time somebody signs up for a newsletter, they're getting what I'm calling a newsletter mix tape - where I've curated past articles, in some case edited and Frankensteined and all these other things.

I've gone through the curatorial and editorial process to make it so the send time of a given newsletter that goes to our email list - is not based on when I send it, but instead based on when the subscriber signs up. So if you sign up this week, you get email number one, and then next week you get email number two. But if your neighbor signs up for my newsletter next week, they get email number one that you got last week, in the current week, and so on and so forth.

And so what happens here is - we've got years of content archive that I can turn into a sequence, so that every new person who signs up is going to get great stuff on a regular basis. Which also means that when I run one of my now Frankenstein greatest hits launches again - they are more familiar with us, they're more familiar with our lessons, our philosophy. They've tried out some of our tools and techniques and realize that they work, and so that gives them a really good reason to want to buy the full course.

And so over the last two years, I've just been kind of working at this machine, where I'm effectively - and I'm still - I'm writing stuff, Amy has written a handful of things in moments where she feels a bit better. I should say, she's been much better in the last year and in the last like nine months especially. So she's back to creating new stuff. But it's still slower than it used to be, and producing something consistently every week is impossible for her.

But what is possible, is for me to have this system that removes the pressure from having to create something new every week. So that when she feels well, she can create something really, really great. And then it goes into the system. And that system - like I said, last year - in the two years that I've been building that system, we've doubled the business, doubled revenue - with basically no changes to our costs. Gets essentially a 100% margin for us. And I've done that with almost no new material.

I think between us, we've maybe written five or six new things - and most of them have been me, and then me asking Amy, "Hey, can you tee up this email?" But along the way, learning how to both puppeteer Amy's past work - but also refining her work has made me a better writer. So I can sit down and write a new original email - that's not going to be as good as something that she'd write, but I can get pretty darn close these days. To the point where - if there's something in a sales sequence that I want, but she hasn't written - I can write it and be close enough that it'll do the work that that email needs to do while we're launching.

And the fact that it all happens on autopilot means now we get - well, now that Amy's getting better, we can put our energy into creating new products. Which are - again - more revenue, more opportunity to help our customers fill in gaps between other products, and things like that. It would have never been possible if we hadn't built this system.

And I would also say - to a degree, Amy being so sick the last two years was the challenge for me to really think about, "Well, what is my role in this business? I've been the co-teacher for a long time - but when we're not creating new material, what exactly do I do here?" And realizing that one of - the way our strengths are complementary, I've started thinking about us as the recording artist and the producer. I don't think Amy will like this reference. But she's my Eminem and I'm Dr. Dre.

I can take her past work and make it even better through this editorial process. But also make it so that the work that was done continues creating value for our audience, for our students, and for our business, long after it was created.

Len: Thanks very much for sharing that story. I think people who are familiar with Amy and with you will really enjoy having heard that. I think it's so interesting that you and Amy faced the same challenges that the people you're teaching face. And that's one of the reasons that you're so good at it. And congratulations not only on - to hear that Amy's feeling better, but also on the success that you've had since you've taken this new direction. It's really interesting. With a business like yours, it succeeds when it works and when people succeed doing it.

Alex: That's right.

Len: And so there's this great kind of feedback effect - not only for you, but for everyone that you reach.

Alex: Yeah. It's been - there's a lot of things that I'm super grateful for about this business. To run a business with a friend, first and foremost - means that Amy getting better means I get my partner back, I get my friend back. But we also get this kind of like new tool. Our business just has this different shape that we get to relearn how to work together in this - to me anyway, this positive and exciting way. Our foundation is stronger, and the work that we put in can - I think the dream of an asset-based business is that the work that you did in the past is leveraged for work you'll do in the future. I think we're living that more today than we've ever been able to in the past. And part of that happened because we had this kind of terrible constraint forced upon us, and could've said, "Well screw it, I'll just wait for Amy to come back and be better." But, a) I would have not been a very good partner, but, b) I think that would've been not fully deploying our own lessons. Which are - you won't always have every advantage that you wish you had, but you have to analyze the advantages you do have, and use them to the best of your ability.

I think I had a moment to be honest, and try to do that in a way that I hadn't before. And I mean, I appreciate you saying what you said - it makes me hope that our students will see, "Oh, there will be a time when this is going to - I will face a seemingly impossible challenge. I've got to go back to fundamentals, and look for every advantage I've got, and do my best to leverage them. I may end up in a different place than I intended, but I also may end up in a much better place than I intended." Which is what happened with us.

Len: Speaking of fundamentals, you've just handed me a second segue gift.

So, we've reached feature length already, but the last - we always save for the end of these podcasts - the view from ground level, rather than from 30,000 feet. And so I was wondering if we could maybe take a little bit of your time to address the challenge faced by someone who has an idea for a product - in this case we'll say specifically, given our audience - a book. Let's say someone has an idea for a book they'd like to write. What should their next step be?

Alex: Your next step should be to write down that idea and then stick it in a drawer and forget about it. Because that idea - unless you have done all the things I'm about to say, is not helpful to you or your audience.

Instead, what I would say, is to figure out who you are best suited to create things for. You may think you know who that is, but I would argue that most people - again, articulate it in a way that is some vague avatar. Or people who like X and do Y, and are looking to be able to do Z.

And, again - so it's a made-up concept that is more derived from your idea than from an actual group of people out there. And so the very first thing I always encourage folks, and this is straight out of our course - is to think about who are the other professional people, and I'm going to narrow in on professional, and I'll explain that in a second. Who are the other professional people who do things like what you do? Who else has a similar job title, or who would like to do the work that you do? Or, who - also a professional, hires you to do the work that you do?

And within that trifecta, you have a multitude of options. It's not that you need an audience that fulfils all three. Those are also like brainstorming vectors of, who out there are you well suited to serve?

And the reason I caveat it with a professional audience - it's not that you can't sell to consumers. Consumers being the general public, if your idea is like - You mentioned there's some folks that listen to Leanpub and use Leanpub to publish fiction. That's great, and I'm not saying your fiction is not worthy of readers or buyers - but it is very difficult to reliably create fiction that will sell. Which is why most people create lots of fiction fairly quickly, in the hopes that some of it will sell. Consumer audiences are fickle, and it tends to be more of a hit-based model.

When you're looking for reliability, professional audiences are most likely - not guaranteed - but mostly to buy on value. Which means they have problems that cost them money or time, and they view their ability to spend money they have to reclaim that time or energy as worthwhile.

That may not be the way you think - but if you are a professional, there are people out there who think that way. And this is one of those rare times where I'll say - if you do not believe that is true, you'll either need to believe me ,or go do some further research on human psychology in business.

But that is a generally fundamental fact with very rare exceptions. Professionals that like - like K through 12 teachers generally - even though they're professionals - it's not that they don't buy on value, it's they generally don't have money to spend. Restaurant owners sometimes have money to spend. But they generally don't buy on value, they buy on first impressions and things along those lines. So a professional audience - either people who do what you do, people who want to do what you do, people who hire what you do.

And then, I've already given you a bunch of first steps. But the last piece I'll give you right here, is to then go out and help those people. Meet them where they are on the wide world of the internet we have access to. Figure out where they hang out and talk. And don't go there to sell, don't go there to pitch, don't go there to tell them, "I'm trying to open my next great product idea, fill out my survey." Or, "Would you like me to create X, Y or Z?"

Those are all your job to do. It's not their job to tell you. Your job is to go there, watch those people talk - and understand, take the time to get in their heads and understand, "Why is that person coming on the internet to ask that question? What don't they know? What could they know? What don't they have access to? What don't they understand? What is wasting their time?"

I'll - small plug here - that sounds easier than it really is if you are not practised at it, and Amy invented a research process that we call "Sales Safari." It's at the heart of 30x500. Until a couple of years ago, the only way to learn it was inside 30x500. We now have a standalone Sales Safari 101 course at shop.stackingthebricks.com, where you get to learn by watching us do it. A lot of people will go find a forum or email list or subreddit, or whatever, of their audience talking.

They'll look at it and say, "I don't see anything." And that's just the blindness of your own knowledge, and not taking the time to understand that those people have problems, and there's a very strong chance that you can help them. If you can find people who have problems, that want help with those problems - and you have the ability to help them - that's everything you need to build the foundation.

So that when you figure out what book they want to buy, what book they want to read - you're not going to be plucking it out of that idea that I had you stuff in the drawer. It's going to be based on the pattern of what you saw coming up over and over and over. Or the thing you see people week after week wasting time or money trying to do, or not doing. Or the thing that happens repetitively, therefore it could be automated, and maybe become a software product. Whatever it might be.

But since we're talking about a book and knowledge, what is the thing that is out there? And I'll say one last thing about this, which is - if you're following these steps in your head and wondering or worrying, "Well what if the thing I think they need help with, there's already books out there for?" Well, I've got good news for you. Most books out there aren't very good.

And you have two options. One is to say, "Hey, did you know that these other books are out there?" Or, "Hey, these other books are out there. I read them. Here's what my takeaways are, but here's my personal take on either why that is incomplete, or why there's a better, more current, modern way - or whatever it might be. The fact that there's books out there, is not a negative signal that you should not write your book - in fact, it's a very positive signal that other people out there realize that these problems exist. They just did not do - probably, or maybe they did do a great job of writing a book?

Just because they wrote a book out there about that topic or problem, doesn't mean it's the definitive one for everyone for every situation. You still have the ability to write from your perspective, from your experiences. And to do it in a way, that - based on your own research of that audience, serves them better than the stuff that's already out there. So don't let other stuff being out there be a mental roadblock of, "My idea's not new and original."

In the world of the internet and planet earth and the universe - originality is not the game here. It's understanding them better. Meeting them where they are better. Helping them solve their problems better. Getting them a win better.

And I'll offer a book, if that sounds like something that you want to get better at. There's an incredible book by a woman named Kathy Sierra, who is a mentor of Amy and mine, called Badass that - Kathy and her partner created the Head First Programming books for O'Reilly back in the 90s. And Head First was the first set of books that took a completely different approach to teaching programming Java at the time originally, than ever before.

Instead of it being a book of knowledge and commands and syntax, it was a book of how to use your brain with these tools. Because it was all about what does the programming language enable the programmer to accomplish? No book had ever been written that way before. And truthfully, most programming books still aren't written that way.

But the ones that are - some of our students have written them, continue to be incredibly well-sold - especially as self-published books. They're not the kind of thing that a publisher's going to pick up, because a publisher wants to sell a big fat book - not a 90 page, "I understand your problem and here's how to solve it" book.

But reading Kathy's book, I think is one of the best resources on the earth and definitely on the internet for learning how to really get into your customer's head, and think about how your product - in this case, your book - will make them better in some measurable way. It's an amazing book itself. It's a lot of fun to read. Kathy has a very unique writing and illustrated style. So I'm willing to bet you'll have fun reading it. But if you read it and don't learn something, send me an email and I'll buy the book from you so I can give it to somebody else.

Len: Well, thank you Alex for sharing all of that. I've learned a lot from this interview, and I'm sure everyone listening has as well.

And that's really wonderful advice for someone who's trying to achieve independence, or pay down that mortgage. If you want to come up with a project, one thing to consider is to put that idea that you already had in a drawer, and maybe go out and find a community of people and learn about them - who might have a need that you can address specifically.

And thank you very much for sharing the story about your business with Amy, and about Indy Hall - and about Philadelphia as well. And thanks for taking the time to do this interview, I really appreciated it, and I'm sure all our listeners will as well.

Alex: Thanks so much for having me. I would love to hear from anybody who is listening along who is interested in hearing or learning more. If you're ever in Philadelphia, I have an open invitation to come by Indy Hall. If I'm in Philadelphia, there's a near 100% chance that I am at Indy Hall - but if I'm not, I've got an amazing team and an amazing community of people for you to meet as well. So swing on through and say hi to us in Old City.

Len: Thanks very much.

And as always, thanks to you for listening to this episode of the Frontmatter podcast. If you like what you heard, please rate and review it wherever you found it, and if you'd like to be a Leanpub author, please visit our website at leanpub.com.