$60k in a Week, Plus Ideas for Building the Future of Work with Dan Pierson

Courtland Allen 0s

What's up everybody? This is Courtland from IndieHackers.com and you're listening to the Indie Hackers Podcast. More people than ever are building cool stuff online and earning their financial freedom in the process. And on this show, we dissect the latest trends, ideas, and strategies these Indie Hackers are using to get ahead so the rest of us can do the same. If you've been listening to the show and enjoying it, do me a favor and leave a quick rating for us on Apple podcasts.

Today, I sat down to talk to Dan Pierson of Unsettled. Dan is an expert in what he calls the future of work, which is really new opportunity for Indie Hackers all over to build better tools and applications and software for companies who are changing the way they work.

It's pretty obvious with the global pandemic this year that a lot of companies have been forced to work remotely. They've been forced to work in these hybrid environments. In this episode, we get into your not only Dan's story, but also just a frank discussion about the coolest ideas and opportunities that we see for Indy Hackers in the space.

Dan, welcome to the show.

Dan Pierson 1m 6s

Thanks for having me Courtland. Excited to be here.

Courtland Allen 1m 9s

Yeah. I reached out to you in response to a tweet you made back in October. You said, "$58,000 in sales so far this week for a product that didn't exist one month ago. B2B is wild, not sure why I ever bothered with you lowly consumers." And you never actually shared what it was that you were building that made so much money so fast. So, tell us what you're working on.

Dan Pierson 1m 28s

Yeah, totally. I mean that 60K was two big deals, right? It was $30,000 in sales to a very large technology company in Seattle and it was helping them call it kind of elevated team building, bringing in industry leaders and people who have different interesting things to say. It was connection sessions, helping the members of this organization and break down silos and have intimate connections, and then different workshops that we ran to help them find that personal and professional growth. But it's very, very much tailored to this organization, extremely custom. The second part of that 60K was another 30K deal.

And that was a pilot to help a fortune 50 pharmaceutical company figure out how they could roll out this massive, amazing future of work initiative. And I think seeing how progressive and forward-thinking they were about how they were moving to this new future of work, showed us that there was a market to help other companies do the same and really be first movers in this market of helping companies transition to a hybrid environment.

Those were the first two deals. They very much were taking into account the problems that we heard, but the solution that we're now working on as a product is an evolution, I would say, of those very service-oriented. We're completely customizing this for your needs. That's, I mean, that's a great way to start a business in my opinion.

Courtland Allen 2m 53s

Yeah. I love that point. I've said it on the show a million times. You don't have to start with something complex and ambitious. You don't have to start with a SaaS application, even if that's where you want to get. It's probably easier to start with the service.

You know, something simple, make a bunch of money in your case, $60,000 in a week, and then use those learnings and use that money to sort of fuel you to get to the next step. I also want to talk about this term. You keep mentioning the future of work, you and I spoke last week, and I kept calling it remote work.

And you're like, "No, no, it's bigger than that. It's the future of work." And I think it's important to talk about this because people were always complaining that they don't have startup ideas. They don't know what to work on, but every now and then there's a big societal change. And if people start living a different way to start working a different way, and it's just a good excuse and a good time period to really come up with a brand-new idea and serve some new market that didn't exist before.

So right now, that might be the future of work. We'll see. And then finally, I want to talk about transparency. Because a lot of people are skeptical about being transparent. They're skeptical about sharing the revenue numbers, about sharing the strategies, they're afraid competitors are going to steal their ideas. And your tweet, I think, capitalize on transparency.

You talked about how much money you were making and people ate it up. You got like 1,600 likes. You got hundreds of retweets and responses. Why do you think people were so supportive despite the fact that you're only kind of half transparent, you don't really share what you're working on?

Dan Pierson 4m 5s

Yeah. Marketing 101, you leave a little bit to mystery. It, really, it's the Genesis of years of being open and transparent on Twitter and through Medium and the first, yeah, maybe 2,000 people that tweet in total, but the first 30 that got it there and that retweeted it and put it in front of Courtland who now is having me on his podcast and I get a chance to share the first 30 people that were there, that were my kind of small army of folks that have followed me over the years.

They've all seen all of the downs that then put me in a place to have some of these, call them ups on the rollercoaster of entrepreneurship, where now I'm starting to find more success after years of struggle.

But those are people who have seen tweets about mental health and about me leaving Lyft two months before my cliff. I don't know, the hundreds of thousands of dollars in stock that I left behind and how I've thought about that over the years. They've seen the two financings that were term sheets signed basically, for the second one very much so.

We work in Santa Monica whiteboarding with the two guys who were in the investment firm. And then two weeks later, seeing coronavirus start to ramp up and getting an email that told me that $500,000 had basically vanished. There are people who have been along for the ride, and I think that's so important because if people only see the success and you're transparent about your success and you're kind of just bragging and you're kind of just an asshole.

I think there's two sides of the coin and people embrace the vulnerability and people embrace the transparency when you're sharing things that it's not just the good times.

Courtland Allen 5m 49s

Yeah, I was going back through your old tweets and you've got one from July of 2019, last year, that I liked and retweeted. And you start off by saying, "I've been walking through the entrepreneurial desert since August 2014 when I got my last paycheck from Lyft. Five years of broke struggle. Damn, dude."

Dan Pierson 6m 6s

I mean, I've been so broke, I can't pay attention. It's been so long of just trying these different businesses that, you know, have their moments of kind of, most of the people listening to this podcast can probably relate to where, you know, it seems like you're finally about to hit that precipice of success and then suddenly it's further out in the distance.

The entrepreneurial process is never overnight. You always hear that. It's one of those kind of truisms that you know, you see people say like, "There's no such thing as an overnight success." That is so damn true.

Courtland Allen 6m 37s

Yeah. I think that's very true. There are very few overnight successes. But I also want to know what you've been doing to be so broke. Because you don't have to be broke to be an Indie Hacker. I know a lot of people who are never broke, they're never super stressed about finances. They were never wondering when their next meal was going to come from already working on last year when you tweeted that. And also walk us through this five years you spent in the entrepreneurial desert, as you called it.

Dan Pierson 6m 57s

Yeah. The last business I was working on, it was called Bolt Travel. So it was, this idea of community travel, millions of people spend billions of dollars a year flying all around the world for these group travel experiences with complete strangers, which I thought was just kinda crazy.

We, our innovation there alongside awesome trips like rooftop tent camping, Safaris in Africa, and sailing in places like Greece, Norway, and the Caribbean, and overlanding in Baja and hiking in Patagonia, all those trips. The innovation we were bringing there was this idea that you could build community around those experiences and extend those experiences.

And I mean, it was going great, man. When I say we, very much I mean me. I was a hundred percent by myself Indie Hacker style. I always use the kind of colloquial week. Cause I feel like you're talking about a company and it maybe makes people think that you're a little bit bigger than you really are, but very much it was me.

That was what I was doing up until March 10, 2020 when I had to, get people back from Panama and get people back from Patagonia and then face over the course of a month or two increasing understanding that my life in that business had changed forever due to the pandemic.

Courtland Allen 8m 10s

Yeah. That's an interesting point about saying I versus we, because I think a lot of people in the Indie Hacker space are benefited by being very personal and down to earth. Especially if you are in the education business, if you are spending a lot of time directly engaging with an audience. People like to buy from a human, to kind of know who you are and what your story is more than kind of this nameless faceless organization.

But in your case, it might've been different because you were actually organizing these big trips for people in groups. And maybe they want it to think that they were in good hands and that if you're a professional team of people who had done this before. What was it like being an Indie Hacker working by yourself in the travel business?

Dan Pierson 8m 43s

Yeah, totally. And it was very much, I was flying by the seat of my pants. I had very little direct experience in creating that kind of travel product at scale. I'd always been the person that put together those kinds of trips for friends and family. I'd worked for Lyft, managing your travel partnerships, but those were figuring out how we could partner with hotels and airlines to get more people to drive in cars with pink mustaches.

It wasn't facilitating travel experiences all around the world. I started at square one. I threw up a really terrible Squarespace page for that company, for Bolt. I emailed, you know, probably 20 people, told them what I was doing. And the very first trip that Bolt's ran was in Oaxaca and there were, including myself, five people on it.

The other four people, one of them was my brother, one of them was an ex-girlfriend from San Francisco, one of them was a buddy from San Francisco, and then we had one random who's a Bitcoin millionaire. And I was looking for people to hang out that were engineers, get really good guys, I should say.

But that was that first trip. And that was the start of that business. And from there I think about marketing any business, but particularly I think for Indie Hackers, I think if you picture concentric circles, like the smaller circles within larger circles, the first circle are the people that you know the best and who support you and want to see you succeed and like are going to be your biggest advocates and that's who you start with, right?

And then the circle outside of that is then the people who, you know, maybe you've worked with in the past, haven't talked to him in a while, but could be interested. And then you move further and further out until you reach the group of people who you've never talked to in your life and like then your product better solve a problem pretty good for them.

But until you got there, you have these people who want to support you. And that's a great place to start.

Courtland Allen 10m 29s

And what about this five years wandering through the entrepreneurial desert?

Dan Pierson 10m 23s

I'll start this story about pretty much 12 years ago, right out of college. I started a very successful internet marketing agency by myself, down in Argentina.

I'd moved down there to teach English, couldn't find those opportunities. I started writing freelance articles. And it was very much the heyday of SEO spam article writing. I started higher. I found some success with that and started hiring other Americans who had moved down to Argentina in a similar fashion to teach English and couldn't find those opportunities and built a really successful agency out of it that I ran by myself as all like, you know, kind of freelancers, but I was running it.

And I mean, it was very much like Tim Ferriss' 4 Hour Workweek style, maybe even before he coined that term was 2009, 2010 or right alongside anyway. I made more money working less back then than I ever have even come close to sentences making. I was netting like 10K a week. And which was wild because I was 23 years old flying all around the world, you know, in first-class, having these amazing adventures.

That was the start of my career. That was my first taste of entrepreneurship and literally that started with me writing an article for like $6 about going on a vacation in Cape Cod for like God knows who. That was the start of that business that turned into this pretty substantial venture, until it got smashed by Google updating Panda and the whole SEO industry changing overnight just demolished that business.

Courtland Allen 11m 59s

Just give me a sense of the economics of a business like that. You're hiring a ton of writers. You are writing a ton of content. You thought it's smart back then. So, you get to the top of the rankings. And then what you're making a ton of money on ads?

Dan Pierson 12m 9s

It wasn't even that sophisticated. I had primarily one client, which is like the most beastly broadly internet marketing company that no one's ever heard of called Red Ventures. They're now, I think, maybe even public. But they have all these different verticals where they're selling, reselling ADT home security, and they've got every, like they're completely vertically integrated. They have websites where they're capturing traffic. Then they have a call center.

Courtland Allen 12m 35s

Yeah. I'm looking them up right now and they're huge. They own CNET, they own ZDNet, they own TV Guide, they own Metacritic, they own GameSpot. This is a huge media company.

Dan Pierson 12m 44s

Exactly. Back then they owned all of these, this web of web properties, hundreds and hundreds of domains where they would capture traffic for ADT home security, satellite TV, a bunch of other kind of consumer products. They needed a ton of articles to rank for them. I found them on Upwork or rather they found me on Upwork. Upwork didn't even exist. It was Elance, this was 2010. They found me on Elance. I did maybe a $1,300 project for them where I wrote like 20 of these complete bullshit articles myself.

And then they were pretty dramatically quickly escalated to we need 500 articles a week at 15 bucks a pop. So, I was like, okay, cool. I can hire Americans living down here who have degrees from Yale in English, but can't find work teaching, you know, people how to speak and write. That turned into a big opportunity, but it got smashed overnight. I mean, literally overnight it got it got demolished.

Courtland Allen 13m 41s

Yeah. I can't imagine what it felt like to go from making 10 grand a week at 23-year-old to later in your career try to be an entrepreneur take two. You know, you're trying to get Bolts Travel off the ground and it's a slog, right? You're taking your sister and your family members on vacations, you know, trying to get your first clients. How did it feel to taste the real hardship of entrepreneurship after having such kind of an easy success early on in your life?

Dan Pierson 14m 3s

I think about being a monetary success, like I was making all this money and that was admittedly awesome. But I felt like I was contributing zero value to humanity, perhaps even being extractive, just putting this complete arsenal of complete bullshit out into the universe, right? And so, coinciding with that business getting affected by, being so badly affected by that Panda update, I'd become really interested in collaborative consumption, the sharing economy.

This was like 2011, 2012, right, when it was starting to take off. I sent a cold email to a VC that turned into a three-month internship in San Francisco at a sharing economy company that then turned into a role at that VC that then turned into a Lyft in 2013, 2014, right, kind of as Lyft was taking off.

And, yeah, it was definitely, I felt much more fulfilled in terms of the projects I was working on, having deep, important impact on humanity. But I still really didn't have the kind of freedom and the balance between living to work and working to live that to me is fundamentally important.

I just started taking 30-minute-long walks during the day, hour-long walks, 2-hour long walks, and then I quit my job at Lyft about two months before my cliff. I left, I don't know how many hundreds of thousands of dollars on the table, got on a bicycle and rode across the United States by myself.

And that was really, you know, my return to entrepreneurship after that first company that I started doing SEO content marketing. I spent four years net grind in the Silicon Valley, and then decided it wasn't really for me.

Courtland Allen 15m 44s

It's hard to go from a life of freedom as an Indie Hacker to a life of basically a desk job. Or you have a boss telling you what to do and you've gotta be dressed a certain way and gotta have your butt on a certain chair, a certain time every day. It's the freedom has got on the number one thing for most people who've tasted it before. It's kind of like the baseline, because even though you found purpose at these tech startups, you said you were talking, you were working for the sharing economy companies, you ended up at Lyft. And the sharing economy is this very purposeful thing.

It's kind of a marketplace-based apps where you're connecting people to people. So, Lyft and Uber and Airbnb, I think is an even better example where it's a little bit more humanizing and people can sort of help each other. And even though you have a purpose there, if you don't have freedom, it's almost like the operating system of happiness.

Like you could, once you get that base layer down, you can start to build all sorts of apps and programs on top of your freedom. But if we don't have freedom, even if you're making a lot of money at a big company, it could feel like you got to get out. You got to do something else.

Dan Pierson 16m 37s

Exactly. I mean, for me, I think I take it over money. You know, there've been times over the last five years, as you alluded to, when you read that tweet where I've just been, you know, sober up. But to me, the fundamental freedom to be talking to you on this podcast from, you know, the coast of Oaxaca, Mexico is the most important thing. And then one that I just absolutely need to optimize for.

Courtland Allen 16m 58s

Okay. So, you're done with Silicon Valley. You're done not being free. You decide you're going to be an Indie Hacker again. What do you do?

Dan Pierson 17m 3s

Sure. It's about a year and a half of travel after Lyft completely disassociating from Silicon Valley. And that led me to 2016. It was like, there's no way that I want to go work at these businesses again, these large Silicon Valley startups.

I recognize that wasn't the life for me. I started a new business that was probably on paper sexiest business at 500 people have started and they've all failed because it's a terrible idea. I can get into that one if you're interested, but…

Courtland Allen 17m 41s

Yeah, for sure. Let's hear it.

Dan Pierson 17m 42s

It was helping people, people understand how they could best use their frequent flyer points and miles. This is how that business started, it's called Slingshot. I posted a photo of myself in first class on Cathay Pacific airlines on a flight from Hong Kong to New York city. It's the longest flight in the world, or at least it was at the time.

Posted a photo and said, you know, "Do you want help learning how to do this? Would this be valuable if I helped you do this?" And it got, 250 likes on Facebook and all these people hitting me up and I was like, "I've got something here. I've got something here." And I spent two years trying to make that work and burning through a ton of savings and yeah, and it was just, it's a brutal business because the banks and the credit cards and the airlines don't want to share any data because they have no reason to.

And that whole system is opaque for a reason. I took learnings away from it, for sure. But I mean, it was to call it to, a full two years of working on a business that I should have after three months realized it wasn't going to be any kind of success.

Courtland Allen 18m 41s

Okay. So, let's fast forward to where you are today. Your travel businesses don't work out. Bolt doesn't work out. Obviously, it's pretty hard to have a travel business during a pandemic when traveling is basically illegal. But now you’re working on a company called Unsettled. And you're doing these crazy deals. You made 60 grand in a week. Tell us about how you got here.

Dan Pierson 18m 57s

Rewind to March 2020, that deal fell through, which was going to give me the security that I had lacked forever. I mean, part of that deal was a $50,000, they were buying $50,000 of my equity in the company. And that was just going straight to me to pay off credit card debt that I had accrued building these businesses.

I've written Medium post about that and they could link in the podcast or something, but that was going to really give me a lot of security that I'd lacked for so long, you know, like that tweet that I referenced about being broke for five years. In the process, reframed a lot of what I was thinking, realized that okay, travel’s not coming back anytime soon.

Two friends of mine had started a company about five years ago called Unsettled. And we just started having frank, honest conversations about maybe we'll be able to get through this and get to the other side. The likelihood of that we'll be stronger if we team up, and we go through this together.

That conversation turned into them acqui-hiring cause again, it was just me full-time. Bolt is to be a part of Unsettled's primary product before the pandemic was 30-day retreats around the world. It's like Tuscany, Buenos Aires, Bali, Cape Town, they'd set you up with an awesome place to live, co-working space, and then a really intentional, thoughtful set of experiences over the course of 30 days with the premise that you need to be a little bit unsettled to realize true personal and professional growth. Because if you're not then you're kind of just coming at it from a place of stagnation and a comfort zone and it's not really the moment when you're going to find that kind of growth for yourself.

Unsettled, obviously, their travel product got smashed equally hard in March and we have that frank conversation. They gave me a bunch of their company for joining, enough to really feel like I'm an owner of it, which was an interesting transition, I think from being an Indie Hacker to being now part of a team.

Courtland Allen 20m 54s

Okay. Both of your businesses got crushed by the pandemic and you decided to join forces, but you're pretty much still at square one. I mean, this is where almost every Indie Hacker is, trying to figure out what's it going to work on to try to make money. And that's where you were because none of your old stuff was going to work in the pandemic. How do you come up with a new idea from scratch?

Dan Pierson 21m 10s

Unsettled had put out virtual experiences, but it was all business to consumer. And when I came on, what I really wanted to work on was business to business opportunities. So, figuring out again, totally online, what value Unsettled's approach could bring to different businesses and different organizations.

And we went through 10 different iterations, talking to so many different businesses. Big, small, had been remote forever, never been remote a day in their life, you know, different industries, all different kinds of businesses, and try to figure out what their pain points were, how we could solve them.

And over the last, call it, three or four months, very much service-based, we put out a bunch of different kind of feelers to friends, alumni of people who'd been on Unsettled trips just to start conversations and really learn what the problems were around this very sudden dramatic shift from the office to remote and hybrid environments.

Courtland Allen 22m 9s

Yeah. I think this is a process that a lot of Indie Hackers kind of skip, which is determining what you actually want to build, right? You don't want to just randomly start building something because you're excited about it. I mean, that can work, maybe you'll see even a hundred or 200 examples on Indie Hackers of people doing that, but you don't see like the tens of thousands of people who tried that and build something that nobody wanted.

But if you actually start with your customers and you start with their problems and you're asking them what their challenges are, you're looking at where they're spending money, or maybe even just doing research. Any Indie Hacker could go type in news.google.com and just do some research. Type in future of work or remote work and you'll get a ton of articles and you'll see a ton of people talking about their problems and what they're struggling with. So, I liked the fact that you guys actually sat down and did that work.

What did you discover? What are the kind of the top problems that people had that were worth solving and building a business around?

Dan Pierson 22m 56s

That's probably mistake number one that every entrepreneur, including myself makes, is trying to solve problems that either don't exist or don't align with people's actual kind of use cases and what they're doing and what they're trying to figure out. Such an easy mistake to make.

I find myself literally still making it every day, having now started successful businesses and failed businesses. So, yeah. The feedback that we heard from all these different businesses that we spoke to was they had made that transition overnight from collaborating, communicating in the office to now having to figure out how to do it in a remote environment and like both as individual contributors and then as organizations, just like chickens running around with their heads cut off. And I think March, April, May, it was so reactionary that companies fell into bad habits and negative routines around remote work. That was really the challenge side of it.

Now I think that we've been working remote for seven or eight months now, like now I think there's an opportunity to transition to the opportunity side of things and like, "Okay. Let's solve these problems and see how it can manifest as positive implications for businesses. I myself have stopped referring to it as remote work, because I think it extends so far beyond that. All of the companies, almost all of the companies, I should say that, that we talk to they want to get back to the office in some form or in some shape, or maybe it's not even the office, but it's in real life experiences, you know, in 2021 and beyond as the health situation improves.

Maybe, you know, a hundred-person org is ditching their office. And suddenly that budget is freed up to fly everybody to Bali for 10 days for the Austin team retreat kind of thing. All that's to say most companies I don't think are going to say, "We're completely ditching in real life to go a hundred percent remote.”

I think what's really exciting about the future of work, if you keep an open mind to it is that it's expansive and it's unlimited and it's exponentially open for new ideas to the point where we're going to find these hybrid environments and hybrid companies and hybrid everything that like takes the best parts of being in person and having that IRL connection and matches it with the flexibility and the opportunity to work at your best, whenever you want, however you want, wherever you want.

That's the kind of company that I want to work at. And I'd imagine, for at least a lot of people, like the kind of company that they would want to work out, too. Who doesn't want to have their cake and eat it, too?

Courtland Allen 25m 34s

Exactly. Who doesn't want to eat cake? So why don't we talk about some ideas? Let's talk about some of the cool companies we see out there in the future of workspace. And maybe this will help people get their creative juices flowing for companies that they can start themselves. What do you see, who's inspiring, and what are some of the cooler businesses that are catering to this future of work?

Dan Pierson 25m 52s

There are so many different apps out there that are trying to tackle like what it means for all of us to be working in this completely new environment. One of my favorites there is called Icebreaker. I think of it as what would technology look like for connecting us in a really intimate, fun engaging environment.

If we'd started out with this idea, rather than being in a business context, we're doing this for social connection. They're flying in literally Icebreakers into the conversation and sending people into breakout rooms accordingly and giving people the prompts they need to be human, right? It's definitely not what we use for an important sales call, but internally to build culture at your team. It's like a much better tool than something super utilitarian like Zoom.

Courtland Allen 26m 43s

There's no personality with Zoom. It's a hundred percent utilitarian, like I must call you and you will pick up and then you call somebody and they pick up and you have a conversation. And that works. I mean, that's fine, but I'm on Icebreakers website right now, www.icebreaker.video.

And they got all these little cool events. So, you can do a happy hour or you can do some sort of virtual meet and greet. And if you click into the events they tell you, "Okay, here's the template, here are the little cards, here's what the prompt is going to be, here's what we're going to match people together." And it looks like they're free for basically teams of up to 40 people at once. But once you get past that, you've got to pay a hundred dollars per group, which is actually not that much.

I can see people adopting this and really getting used to it and creating company traditions and making it part of their culture. And then eventually, you got hooked on it and you're paying a hundred bucks a month to make your team better, really, which seems like a good deal. I've seen some of this stuff early on during COVID, somebody had I think a goat cam, where they would put a goat on camera from their farm to just sort of join your Zoom calls, just to kind of spice up your meetings and make it interesting. But this one seems a lot more, I don't know, purposeful.

Dan Pierson 27m 46s

Yeah. I think it's a great example of human centric design and that's something that I think a ton about that is the small team that I'm working with that we think a ton about.

Courtland Allen 27m 55s

There's a couple of other ones that I've seen that are pretty cool that are part of this idea for having kind of a virtual HQ for your team. One is called branch.gg. I signed up for that one, but they haven't let me in yet. Another is called www.gather.town. And it's kind of the same idea. Rather than kind of sitting at your desk all day and looking at Slack, they have these virtual almost game-like areas where you have a little character and this top-down view like you're playing Zelda or something, and you move around the little virtual office that they've created and you can see all your coworkers.

And I think the whole idea behind it is that you don't really have to ping somebody for a call. You don't have to schedule a call and figure out when you're gonna talk to them. You just walk your character up to their character and you just start talking. And based on the proximity of your little guy on the screen, people can hear you if they're close enough to you.

I've been using this for the last week with my brother, just trying to test it out. I haven't got the rest of my team to sort of buy into it. But it's cool because it brings back a little bit more of the serendipity factor of working in an office. So, the little map that we're on is like an actual office.

They've got little chairs at desks that your character can sit on if you don't really want to be disturbed, or you can go literally stand by the water cooler and the cafeteria and people can walk up to you and to start talking.

Dan Pierson 29m 5s

I totally get that need and it's something we hear from our prospective clients and the folks that we're working with now. All day it's like that kind of Jane Jacobs style, you know, creative chaos, people bumping into each other and starting new ideas and starting new projects, and eventually even starting new companies. What does that look like in a world where we're all spending 97% of our time at home? It's funny, I'm kind of at the opposite end of the spectrum.

I'm like, how can I look at the screen less? How can I be no video; on calls without offending people and just audio only? I'm really excited but I don't have an invite yet. Maybe I should, maybe somebody that's listening can hook me up. Clubhouse I know is blowing up as audio only because I think people, you know, we've been on Zoom for so long that now people are looking for, I think a lot about cognitive loads, and we have to think so much.

And I think actually Zoom and other platforms even when it's really, really well done, there's still that kind of instinct in your brain that tells you, "Oh, this actually isn't natural. There is a millisecond of a millisecond delay and it just doesn't feel natural." I'm big on the audio only, but I definitely see the value of the platforms that you're talking about like Branch.

Courtland Allen 30m 19s

Yeah. The audio only thing is really good. Even Branch and Gather I think they have video built in, but it's not really, like you don't need it. I was talking to my brother in Gather this morning without, I was on my phone and I don't think they have support for video on your phone.

But it felt very much like Clubhouse where it's kind of like you can just walk around your house talking to people. And the problem with the Zoom chat is even before this podcast, I had to clean up my living room to make sure it doesn't look like shit and make sure I'm wearing a shirt, wearing pants and stuff. And it's just like a little bit too much friction versus these audio only platforms kind of solve that serendipity problem where people can just kind of walk up and talk to you and there's no preparation necessary. You can just kinda talk to your coworkers and just jump right in and out of conversation without any of that extra friction that is honestly just annoying.

Whenever you have to schedule a call, you need to go through this this process of figuring out what time are you free? What time am I free? What's the best time? Then it turns into this whole big thing. And then maybe you just wanted to ask a really simple question that could take like five seconds, but because you scheduled time for the meeting it ends up dragging on like longer than it really needs to just to make it feel like it's worth it. It was worth setting this whole thing up, but it's just stupid. It just makes no sense. It's just obvious, like this is eventually going to be better.

Dan Pierson 31m 28s

Exactly. And I think particularly when you're talking about the act of building consensus around how people communicate and collaborate within an organization, within a company, that's the product that we're building. That's where I spend 95% of my working hours thinking about.

Courtland Allen 31m 44s

Right. So, you had these two services that you created that you sold for 30 grand each, but you're trying to turn these services into actual products here. Give me an example of one of the products that you're working on.

Dan Pierson 31m 54s

Sure. Yeah. Fundamentally it all starts with self-awareness. We're building what we think of as very simply as the Myers-Briggs or the Enneagram for the future of work. Right?

There's this universe of different assessment tools. I mean, it's massive and companies pay tens of thousands and hundreds of thousands of dollars for companies to come in. And as consultants run these kinds of assessments, but nobody's ever built one specific to the needs of this rapidly changing future of work, where we're communicating asynchronously and we're figuring out in real time how people like to work.

We’re taking personality assessment, how people communicate, how people collaborate, and using it to really create a completely new framework for how companies and individuals think about the way that they come up together.

Courtland Allen 32m 48s

Yeah. I like that because there's kind of a proven market there. There's a ton of companies that already pay a lot of money for these sort of employee teammate assessments, kind of figure out your personality type, figure out how you like to work, all sorts of stuff like that. But given that the world is changing and people are now working more remotely and they're working from home and working hybrid. Some people are remote, some people are in the office, et cetera.

It's kind of a gap in the market or kind of a new opportunity to produce an even better assessment that’s sort of tailored for this new way that people are working. And companies probably won't balk at paying for something like that because they already pay for stuff like that, but they want to have the latest, the greatest. They want to have something that's actually accurate with how people are working today.

Dan Pierson 33m 25s

Exactly. I think the next question from there becomes okay, you have an individual assessment for each of the contributors at your organization. And they understand that Myers-Briggs, for example, I was introversion versus extroversion in Enneagram of folks, or maybe some folks are familiar with that. It has different types that explain how you like to collaborate.

It's very easy, I think for those to kind of get siloed and to not be useful in terms of how they relate to how you operate as part of a team or as part of an organization. So, that's the second element of what we're doing, is taking all of those assessments and surfacing the trends that come that come from them.

That's using data from the assessment, aggregating it from all those individuals to create a report for managers to say these are, for example, the working hours of the people in your organization and the tools that they use, but more importantly, how your people like to communicate, how they like to solve problems, and starting to figure out across the company, what that looks like.

Ray Dalio's a great example for folks who maybe have seen his TED Talk. Bridgewater, which is literally the most successful hedge fund in the history of hedge funds. This is his way of making sure that the best ideas surface and like in real time. During meetings, people are evaluating ideas to make sure that the best ideas win.

Assessments are just a fundamental, when done right, they're a fundamental piece of making sure that businesses have the opportunity to be at their best.

Courtland Allen 35m 0s

Yeah. I've seen that TED Talk. It's pretty cool. It's called, I think he calls the software The Dot Collector. And so, there's people literally sitting in this meeting and he's giving an idea and people in the meeting are reading, "Is this a good idea? What's my feedback for Ray?" But then instead of just seeing their own individual feedback and what they thought about Ray, they kind of see an anonymized chart of what everybody else thought of that person.

So, they can see, "Oh, I gave him a 3 out of 10, but like everybody else gave him a 9 out of 10. Maybe there's something wrong with me. Why did I interpret that so differently, et cetera?" And it's just looked extremely distracting. But how could you even pay attention to anybody when you're sort of constantly reading what they're saying? But I think the idea behind it was kind of cool, which is that we can come up with quantitative ways to figure out how we've worked together and what everybody's preferences are. You know, who should we pair up?

Somebody might be extroverted, somebody might be introverted and maybe they should work as a team. Somebody might like remote work or a video call. Somebody might like audio calls. And if there's some way to kind of find that information about somebody before you work with them, then ideally, it'll sort of improve your working environment.

Dan Pierson 35m 58s

Exactly. So, you know, across an organization, there are going to be points where you want best practices and you want norms. And that's what we do next, is we create a remote communications charter. I think about Stripe, where at which you sort of work for, as one of the most progressive, healthy cultures.

Imagine if every single company out there was as progressive as Stripe and had the kind of tools, structures, resources, common understanding for people to work at their best and to really feel like they were in the best positions to solve any problem that came out there.

There's a thousand companies that are just like, "We want to see you from nine to five, behind your computer, and these are the tools that we use,” and there's no opportunity to from the grassroots create working environments that leverage all of the challenges of remote work to turn them into opportunities.

That's a super important component of what we're building is that they have like grassroots bottoms up. You have a say in the way this company is going to run. And I think the companies that me and you and a lot of people who hopefully have the agency to find the best opportunities like those are the places that they want to work. So, yeah, I think it's a big opportunity.

Courtland Allen 37m 21s

Yeah. And it's interesting to me how the variance between how good or bad some companies are at handling remote work. My mom works for a company and they hire recruiters and there's just super micromanagy. They have software installed on everybody’s computer to watch what you're doing at all times that also measures how long you're there. So, if you're away from your keyboard for 10 or 15 minutes or something, I guess, like sends an alert to your boss or something that you're not working.

Then the employees buy these, I think they're called mouse jigglers, which in some cases for actual physical devices that will just jiggle your mouse to make it look like you're actually at your computer. But it's ridiculous. That's like such a micromanagy, a very low trust way to manage a remote team.

It's indicative of a company that just didn't really know how to handle this transition. And then there are other companies like Stripe, for example, where many people are working remote well before the pandemic. We've got a wide array of internal tools that just make it easier to get to know people and to learn about people.

We use lots of different Slack bots. There's a Slack bot that's pretty popular called Donut that we'll just sort of regularly schedule meetings for you and kind of random other people at your company. It's a great way to kind of keep in touch and sort of mimic the in-person nature of, you know, just bumping into people in the hallway in a real office, where you're not necessarily gonna go out of your way to say, "Hey, random person. Let's meet."

But with Donut, you know, you've got this third party telling you to do it. I liked the idea that there's just all these different opportunities for people to get better at working remotely. And this is a ton of tools that Indie Hackers can basically build to do this that don't exist yet. And it kind of requires an imagination.

You have to kind of imagine a future that's different. Or people work differently than they do today. But if you can't imagine that, and you can just sort of break it down to first principles and say, you know, what should people be doing? Not what are they doing right now? But, what should work look like when people aren't necessarily in the same office together? I think there's just a ton of ideas for things you can build that people actually pay money for.

Dan Pierson 39m 5s

Totally. And I think the most fascinating part to me is that it's never been easier to build those ideas to very quickly get a grasp of what the market needs, and then turn around with a solution that like might not be perfect, but pretty adequately fits the needs and meets the needs of consumers or a businesses.

The last part of this team journeys product that we're building for companies that have gone remote is like a Slack bot, for example. So, you've taken this assessment. It shows you the type of remote worker that you are, how you like to communicate, the best way to reach you, the best way that you solve problems.

And we're building a Slack bot that will surface those findings for any individual at your company at the touch of a button. You can pull up, maybe it's, you know, Courtland works in engineering, I'm in marketing. I need to figure out something about how our email delivery works and I can find out exactly how Courtland is at his best in a remote environment, so that I can reach him in the most effective way possible, literally just by pulling up his remote style. The Slack bot that we're building and it's like that wouldn't have been possible…

Courtland Allen 40m 14s

Very cool.

Dan Pierson 40m 14s

...you know, you're a computer scientist, right? By training at least. I'm like the opposite of computer science has, but with these no-code tools I learned from, Makerpad, like Ben Tossell, Tom Osman, these guys at Makerpad that are just creating incredible resources to teach people like me who aren't very technologically product minded to create tools using no-code.

That Slack bot, right? It's like Flow XO, the tool that we're building that in. And then the database is Airtable. And Zapier's porting the individual profile to Webflow so that each contributor has their remote style...

Courtland Allen 40m 49s

Right.

Dan Pierson 40m 50s

...on what seemingly is a very robust custom website for each of these clients. And this stuff is very, very buildable within the core, over the course of two weeks. And it's a prototype, right? And when we hit it big, God willing, you know, we'll have to write custom JavaScript. But right now, this gets us there and it's doing it quickly, efficiently, and we don't have to hire developers to do it.

Courtland Allen 41m 15s

What do you think about the sizes of different companies that can take advantage of these tools? Because when I use some of the kind of video game type ones, I was talking about earlier, where you're kind of walking around this virtual world and talking to people, I noticed that it's pretty helpful, even for a small team. A little virtual office I have and Gather is huge. It could easily support hundreds of people, but just with me and my brother, I found it interesting to be able to serendipitously just strike up, walk over to where he is and strike up a conversation.

Do you think small Indie Hacker type companies, you know, 5 to 10 people are going to be buying tools like this? Do you think it's mostly for bigger companies? Where do you see the opportunity when you're trying to develop these tools that you're coming up with and sell them to customers?

Dan Pierson 41m 51s

Sure. I hope Gather doesn't charge you by the square foot, right? Or maybe you're just like bawling out and you're going to get like a corner office, you know, penthouse with panoramic views of the San Francisco Bay. I think when you work with three or four people, you know them so intimately well. At companies that are run by people who think about how to make their employees happy and how to take their feelings and how they work into account, three to four or five people, probably don't need robust tools like what we're talking about, but imagine you're at 14 people and 3 of those people were hired during COVID and you've never met them face to face.

You haven't had the opportunity to understand how they work, you know, at their best, how they collaborate, their personality traits, and how that plays into work for a 15-person company, right? I think our sweet spot and we're validating this in true Indie Hackers fashion, we're figuring we're doing our best to talk to customers and figure out who the customer persona is that we want to start with.

We had all of this success early selling into these massive fortune 50 companies, and now we're figuring out actually they have a lot. It's easy to sell maybe 30 or even like 50K deals in these companies.

If you want to sell two or three hundred thousand dollar deals in these companies, you have to go through incredibly rigorous approval processes. And there's so many different stakeholders and I'll be totally honest, I'm very new to sales, enterprise sales, and I'm realizing I like parts of it, but the idea of wrangling 17 different people from Microsoft into a virtual room and making sure that all of them feel good about the solution that you're selling, that it's enterprises.

All that to say that's a very, very complicated process. Hopefully we'll get there. But, I think in the meantime, when I think about our perfect team size, it's 25 to 200 people. You know, they haven't done a million of these assessments. They still have the core issues around collaboration and communication that I mentioned, but they don't have these incredibly arduous processes that you need to jump through to try new things and they want to be progressive and they want to figure this stuff out, but they're not exactly wedded to what they've done before.

Yeah. I think small to medium teams and then hopefully that'll extend itself to larger teams once we're a bit further along with these products that we're building.

Courtland Allen 44m 15s

And what's cool is people are willing to try new stuff right now. As an Indie Hacker, when you have some brand-new experimental thing that you code with one person or it's a no-code tool, you can't really go sell that to an established company most of the time.

You've got to sell them, sell that kind of stuff to people who are visionary early adopters. But right now, the entire way that everybody's working is completely changed. We’re in this weird phase of humanity where everybody is an early adopter. Everybody's willing to try new stuff.

Dan Pierson 44m 41s

Absolutely. I think the advantage that we have there is companies are running around like chickens with their heads cut off, trying to catch up the basic fact that they're no longer working in their office. Whether that's for us at Unsettled or whether that's for anybody listening to this podcast that's thinking about a new kind of interest area starting to explore where there might be business opportunities.

It's been decades of acceleration over the course of the last nine months and that presents so many interesting opportunities to start businesses. Whereas like before, these companies probably, they would have been very, very close to these kinds of new ideas. Suddenly they have to find solutions and, you know, that means that there's opportunities to try new things and create new things even more than trying new things.

Courtland Allen 45m 29s

Yeah. Even when I was selling podcast ads for Indie Hackers, I realized that a lot of companies were just very experimental. They knew podcasting was this big thing that was happening, but they didn't really have any proof that it would work for them. But they were just like, "screw it. We've got a marketing budget. We'll spend some of it just to try advertising on your podcast. Like here's 5 or 10K."

And it was shocking to me how easy some of those sales were, where marketing departments were just willing to spend. And then I think for smaller companies, a lot of smaller companies, they don't have that kind of budget to experiment, but what they do want is they want to be big. They want to kind of emulate what the more successful companies are doing. So, if I was sitting around trying to brainstorm, what I would do is go look at, talk to some people at Airbnb, talk to people at Stripe, talk to people at these bigger companies that others kind of want to be like and figure out what tools are they doing?

What kind of internal tools are they making? You know, how do they handle all these different problems with remote work? And then maybe put together a package of apps or maybe just one app and be like you want to be like, Stripe, here you go. This is how they manage their remote employees. You can do the same thing. And what small company doesn't want to be like these big companies they admire?

Dan Pierson 46m 30s

100%. I think companies where they need to solve problems, they want to spend money. This is a time to figure out where that is in the context of this acceleration of the future of work and one thing, maybe just an idea that somebody will take this and run with it and hopefully it makes you a million dollars.

There’s this idea that every company I think, or 97% of companies, aren't going to be fully remote. They're not going to be fully working from the office. They're going to be some kind of hybrid beyond that. That's something that we hear from every partner that we're talking to now, there's going to be some kind of middle ground.

What does scheduling look like? You know, in that middle ground? What are the tools that tell you, what is the tool that tells you when somebody is going to be in the office and when somebody is going to be out of the office?

Even if that's just a plugin for, I don't know, Google Calendar or something, or a Slack bot or whatever it is that one little tool there is going to be so valuable to so many people that, or could be so valuable to so many people or some variation of that idea, that costs $1 per user per month, then you could sell a million of those. There are so many fundamental things changing that. It means there's opportunities to just try anything.

Courtland Allen 47m 47s

So, what is your craziest prediction for the future of work 5, 10 years from now? Maybe it's not a hundred percent guaranteed to happen, but what could happen to change how people are working and that it would be almost unrecognizable to us today?

Dan Pierson 48m 0s

Fundamental biggest shift that I am hopeful for as someone who is both, spends a lot of my time working, probably too much of my time working right now, is the complete disassociation of time from output.

A friend of mine, his name is Paul Millard, super progressive forward thinker. And he focuses pretty much exclusively on this idea of the future of work. And he asked what are the massively radical questions that aren't being asked? And I think one of the interesting things there is, what is the value of the output that you're creating? Maybe three days a week is actually better than five days a week. Like people talk about four days a week, right?

But, what if it's putting in a concerted 15 hours per week on the most important tasks you have ahead of you and being in a position to leverage those to really, really drive hard on the things that need to get done.

Another person that I look to for kind of interesting forward-thinking ideas is Rahaf Harfoush, she's a digital anthropologist. And she studies how burnout affects creativity, particularly with this idea that how we've measured productivity since the industrial revolution has no bearing whatsoever on how work should be done today if you're working in anything that brings creativity to the forefront.

Because, essentially the most important things that you're doing have now been disinterred from time. You could have a breakthrough in 10 minutes, that's much, much, much more valuable than the hundred hours you put into things that don't matter at all. So, I think that idea that time is now our most valuable resource.

How can we make the most of it? And how can we create the most value in that amount of time? And also tools catch up to that. I use Grain for, Grain is a perfect example or Vowel is another, one of these tools where it takes your Zoom recordings, uses, I guess AI, somehow machine learning to create transcriptions that are pretty good.

They're not as good as if you hired somebody for a hundred bucks an hour, but they're pretty damn good. And then you can make a clip from those videos to share with colleagues or whatever you need to do. I used to take copious notes during meetings and after meetings and have to refine them and all these things.

Now, that saves four or five hours easily for my work. So, I can focus on the things that are most important to me. And that's just one tiny example, but as we introduce more and more of those tools and also just more human centric design and thought to how we work then, you know, it'll just completely free up so much time.

Chris Herd from Firstbase, you see him on Twitter. Firstbase is they call it the operating system for remote work. They set your company up with all of the different technological tools that an employee would need, right. You get a laptop and you get a desk and whatever else your company wants to set up. And then, when you're done working for that company, Firstbase takes it back and facilitates that whole process of procurement and everything...

Courtland Allen 51m 4s

Yeah. It's smart. Shipping desks and computer chairs and monitors to your employees so they can set up pretty good home office, which is amazing because now everybody's working remote. They need this stuff.

Dan Pierson 51m 13s

Yeah. I mean, talk about an incredible business for the time. And he's been working on that, I think for two or three years now. [He has] I'd imagine hit absolute jackpot right now. But the one thing, you know, I mentioned him because, one, cause I think he's great, it's a great business. But two, he just hammers home this idea that we're spending an hour and a half each way on a commute.

When people have that time back, I think that's going to be incredibly valuable, they'll be able to spend on other things that they love doing. So, top line, the work you do should not be associated with time. I don't think it should be a 5-day work week. I don't think it even should be a 4-day work week. I want to work to live rather than the other way around. I hope I'm working two and a half days per week in 5 years or 10 years.

Courtland Allen 51m 57s

Yeah. I mean, ideally you do the work that you need to do and who cares how long that takes. There's nobody standing over your shoulder trying to make sure you work 40- or 50-hour work weeks. There's no sort of untrusting relationship between you and your employer, where they’re making you have to install a mouse jiggler just to sort of fake like you're at your computer. No, it's just you who controls everything.

And I think my vision for the future is that there are a lot more Indie Hackers because I think being an Indie Hacker is all about having that freedom. It's all about understanding that as long as you can get directly to the end customer and do something for them, then you control everything about your life.

And if you want to work longer hours and make more money, you can do that. And you're going to work fewer hours and, you know, make a little bit less money and do what you want, you can do that as well. There is no weird contractual agreement between you and your customers about how long you're going to work for them.

Dan Pierson 52m 42s

Totally. And I'm informed here by literally the wealthiest man in the world telling me that time is the most important resource. I very haphazardly and kind of serendipitously got to ask Bill Gates via Twitter. This was back in 2013 like, "All of the massive resources at your disposal, where do you feel least able to affect change?"

His answer, right? This is literally the man at the time with the most money before Jeff Bezos probably surpassed him. He said, "No matter how much money you have, you can't buy time. Only 24 hours in each every person's day. So, I set clear priorities, like my family and my work. Pretty hardcore about sticking to them."

I literally have that lesson. Every six months or so, I remember that literally the person with the most money in the world told me that. And I'm like, how can I adjust my life to be more in true with this idea that time is the one thing that we can't make more of?

That, to me is the headline of this future of work. If it involves artificial intelligence, hopefully it also involves universal basic income and where people have the opportunity to work on the things that they really, really care about. Cause as, you know, the human race, those are the things that people should be working on. The things that are most important to them and where they feel like they can add the most value.

Courtland Allen 53m 57s

Love it. I think one of the coolest things here is that we're probably the first time in history, just as an individual or as a very small team of people, using no-code tools to build a lot of the stuff that you're talking about and you're doing it in a matter of days or weeks.

You can attach yourself to one of these giant movements in human history. The future of work, the fact that people are feeling more empowered from their jobs that they're working fewer hours or working more on their own terms, they're working in more enjoyable environments and you can actually start a mission-driven company, a company you're actually changing the world in ways that you want to see it changed.

And you can feel proud about what you're doing. You're not just doing something that's opportunistic to make money. And it can also simultaneously make you a lot of money, give you your own financial independence, and allow you to live the life you want to live. I think it's just a cool opportunity and I hope more Indie Hackers build in the space and do things that are real meaningful for other people, so they can be proud of it and they can help themselves others.

Dan Pierson 54m 46s

I'm totally on board. I just think, as someone who's listened to Indie Hackers for a long time and does not have that technical background, this is an opportunity for anybody to come to with an idea and just literally start from square one and be able to get somewhere so fast that you'll have the validation you need to whatever you want to do. Get more customers, raise outside capital, just kind of keep pushing on, on the things that you know, that you found out.

Courtland Allen 55m 14s

Dan Pierson, thanks a ton for coming on the show. Can you let listeners know where they can go to learn more about what you're up to at Unsettled and anything else you've got going on?

Dan Pierson 55m 21s

Absolutely. Www.BeUnsettled.co is where you can find us. If you're working at a company and you find that you're having these issues around communication and collaboration, you feel like you don't know how to approach people to solve problems in a virtual setting, we'd love to chat with you about that.

Personally, @DanPierson on Twitter, Instagram, all that fun stuff trying to always write more on Medium as well. That's @DanPierson too. Look forward to hearing from some of the folks who enjoy the podcast.

Courtland Allen 55m 49s

All right, thanks again, Dan.

Dan Pierson 55m 50s

Thank you.

Courtland Allen 55m 51s

Listeners, if you enjoyed this episode and you want an easy way to support the podcast, you should leave a review for us on iTunes or Apple podcasts. Probably the fastest way to get there, if you're on a Mac, is to visit IndieHackers.com/reviews. I really appreciate your support and I read pretty much all the reviews you leave over there.

Thank you so much for listening and as always, I will see you next time.