Making It, Episode 03: Breaking the Rules with Technology | Presented by Squarespace

I am on a retreat for myself. It's evening. The sun has set behind the mountains. I've had a little sip of something, something. I'm wearing my bathrobe, in my boxers and my slippers. And I'm in a room with walls covered in notes, notes I've taken and shared that reflect Who I think I am. I'm looking at these verbal reflections of me, and it just starts to flow. I start making a show. I don't even realize that I'm doing it until I'm well into it. I am riffing. I am popping and locking. I am talking to people and cameras that are not there, but they are. Are, because I can imagine them, and I'm realizing the power of that imagination. And it just starts to unfold. And before I know it, this show, it's done. And the crowd goes wild. And the credits roll. And I look down and see my feet. In these slippers, I see my legs jutting out these boxers, and I am ready to spend the time and whatever resource it takes to make the thing I just made.

That was Baratunde Thurston, a writer, comedian, and the host of the incredible podcast How to Citizen with Baratunde. And this is Making It, an audio series from Squarespace about starting and sustaining a business today. I'm your host, Alex Wolff, and I believe that starting a business changes you. So I'm sitting down with creators and entrepreneurs to explore how they got their ideas off the ground and kept them going. These are our stories.

I'm Sue Warnke.

This is the sound of Baratunde Thurston setting the scene for his creative process to unfold. He usually lights Palo Santo, puts on some lo-fi beats, and gets started. It may sound like an analog process, but as you're about to hear, Baratunde has had a lifelong fascination with technology. Across his career as a writer, performer, activist, and now podcast host, he has deeply the many ways that tech impacts both our work and our relationships to one another. It's something that I think a lot about too, because if you're gonna run a business, you have to be keeping up with all the tools of today, from the platform where you publish your website to the social apps where you build your following. From DMs to NFTs, there's new technologies developing all around us, and the pace is not slowing down. So how do creative people balance all these tools alongside their work? In this episode, I'm talking to 2 people who are versed in emerging technologies. First, Baratunde Thurston, who sees technology as a catalyst for creativity. Then we're bringing on Hannah Thomas-Uwase, a consultant who has built her career helping people develop more strategic and more caring ways to relate to tech in their professional lives. But let's start with Baratunde on how he uses technology to break his own rules. Welcome, Baratunde, to the show.

Thank you, Alex, for having me. Good to be here.

Now, you run a business and the business has your name in it. Are you and your business one and the same?

Ooh, I'm more than my business. The business is an extension and an expression of a lot of me, but not all of me can be represented by an entity. that has a balance sheet and an income statement and a bank account and customers and things like that. So there's great alignment between me and my business, but the business is not all of me.

So you use a lot of titles to talk about yourself and your work: writer, comedian, podcaster, futurist, activist. I'm guessing you didn't major in becoming a futurist comedian podcaster in college. How did you arrive at these words?

I'm a communicator. I wield words, you know, in service of values that I find important, like liberty and justice for all. And I try to do it with a humorous twist, and I use tech to help get that out there and be in touch with people. So I feel like I'm not just screaming into a void. So that means I write books, and I do public speaking, and I do podcasts, and I host TV shows. I'm in media.

Now, with all those titles, do you consider yourself an entrepreneur?

Oh yeah, yeah. I have started and failed at business several times, and I've always had kind of a hustle bone, you know, in me. I've always tried to find ways to create things that didn't quite exist and to solve problems that I saw out there. My mother impressed upon me this notion of build your own, and I haven't always done that. I've certainly had jobs as well, but it stuck with me. time and time again to try to create the thing that you feel like is missing in the world.

Do you get overwhelmed? Like, do you feel like as a person with this type of business, you know, and which is deeply rooted in keeping people educated but also entertained, like, do you ever feel like every other month there's just another either app or trend? And what do you do about that type of overwhelm?

When you're in this position and you have so many creative tools and audience engagement tools at your disposal, it's maddening sometimes. And then I'm just getting old. I'm 44 years old now. And so I was cutting edge. I'm not anymore. And I don't have time to be anymore because it's a full-time job just to keep up with the ways, the methods of producing, of distributing, And of engaging with the people and ideas that are part of the work that I do. Yeah, it's overwhelming. The speed is wild. The thing that's hot right now won't be— you can almost guarantee it won't be in 6 months, but you can't guarantee it enough not to try it because you might be wrong.

Right.

And there's always something else coming. And we ain't even talking about Web3. Folks are still catching up on Web2, and here come Web3. Is it VR metaverse? Is it decentralized blockchain technology? Is it just crypto flipping? Is it NFT? It's everything, you know? And so I don't know how society's supposed to keep up. I'm wired to keep up and I can't. So it's hard.

Yeah, it's a full-time job to keep up. Okay, so how do you think we can develop or even just use technology in more socially conscious ways?

Yes. Yes. We are so unimaginative. I remember first coming across— I don't know how true it is, but it's kind of hit the popular zeitgeist, like we only use 10% of our brains, or we only use 5% of our brains. And a lot of ancient spirituality is about unlocking different parts of ourselves too. We operate below our capacity in how we use our imagination to construct our social and our political worlds and our economic worlds. And we've taken this colonial era mining, extraction, maximization, scale thing to a dangerously logical extreme where we are coming close to destroying our ability to inhabit this planet. That's a sign that we've gone too far in a certain direction. And there are many other schools of thought about how we organize ourselves, socially, politically, and economically, to still have our needs met, still feel a sense of freedom and liberty and agency, and also couch those in some collective terms and some health terms that go beyond revenue, net income, GDP. There's a lot more ways to feel well and to thrive.

Absolutely. Yeah, I think a lot of people fear, you know, you get the Luddite judgment when you talk about tech in any light that it's not embarrassingly flattering and optimistic. But it's really, we're asking the same questions but wanting a longer answer, right? When we talk about the GDP, when we talk about the economy, we're not saying we don't want to make money. We're saying we want to make money forever and not in a way that's going to ultimately put us in a position where there would be no reason to make money at all because we wouldn't be here. So I think those types of critiques Yeah, critiques are very important. So I want to switch gears a little bit and talk about part of your past. I saw that you actually worked in telecom consulting for several years. Did that feel like a day job?

Oh yeah, that was definitely a day job. If you saw what I wore when I did that job, Alex, you would say that's definitely a day job. And we'd be talking khakis, polo shirts, the polo shirt tucked in.

Oh, nice.

I'm not proud. That's why there's not very many images of me during that time. For me, what defines it as a day job is it was somebody else's business, and I was solving other people's problems that I wasn't necessarily impassioned about or in love with.

Yeah.

But I got more than money out of it at the same time. You know, I got paid, it helped me pay off my student loan debt, and I got educated about certain aspects of business. about tech infrastructure and telecom infrastructure in terms of routers and switches. And so I got to nerd out and get paid, which is somewhat of a luxury as well. There's other ways of getting paid that do not satisfy the mind in any way.

Do you think that phase is necessary, like, for those who are listening and might be in that phase? Because I feel like a lot of people try to skip it, and maybe it isn't necessary. What do you think these days? Like, that kind of like, I'm working for someone else, I'm 60% doing this for a paycheck.

Right, right. That's a good— that's a really good estimate on like, you know, how much of this is for want versus for need.

Yeah.

And passion versus necessity. So whether it's necessary, I don't think I'm in a position to say for just any random person. But for me, it was really valuable. And I do know there's a lot of rhetoric. There are a lot of people selling Dreams to us right now.

Absolutely.

Find your passion, do what you want. Don't spend any minute of your life doing things that don't serve you. Yeah, that's great. That's— not all of us are in a position to do that. Some of us start, you know, from a deficit, literally financially, like student debt or family debt. And we're just trying to like get our first home in our family, you know, something like that. So The idea that you would just start with the dream I have and I will never work for anybody else and I'm going to— that can work, but it's not a requirement. And I think working for someone else, working in someone else's business can be not just a source of money, but of education. You can find out what you don't like, what doesn't feel good. You can meet your future co-founders. I started a whole business with people I worked with at The Onion. So I worked there for 5 years and then spun off and did something else with multiple people that I used to work with. So The Onion helped seed the idea of a business and paid other people to work with me to vet whether I'd wanna start a business with them. They were like my Y Combinator. Now, I should just say The Onion holds no shares in my company, and that company's dissolved anyway. It doesn't have to be zero-sum or either/or. And I don't want people to feel bad about having a job, because I think there's a lot of rhetoric out there that says the only job worth having is the one you create for yourself. And that's a great aspiration, but getting there, there are many paths to it, and not all of us are in a position to start at the end of the path.

Yeah, I feel like it also runs super contradictory to what I think is another mainstream message, which is sustainability. Which is collaboration, which is, let's all sit down and figure this out together. And it's like, well, one of the ways we do that is by teaming up, working together, working for one another, in some cases. And that not being seen as such a bad thing.

Yeah.

Because Lord knows, if we're all just trying to go through our own individual paths, we might not, like, reap the same benefits, or lessons, or wisdom as we could if we collaborated.

True, true, true. Very well put.

One last question I want to ask you is, in your work, where do you find contentment?

I'm an interactive, creative entrepreneur. My work, whether it's in writing, stand-up, live streaming, I do best with an audience/community around me. And so where I feel most satisfied and most content is when I can feel that what I am projecting is being received and that I am also affected by the people around me. There are times when I've gotten so emotional and so raw and so real with people, and they feel that. They're like, this is different. This isn't just a lecture or a performance or a webinar. And then they open up because I opened up. And they share something back in the comments or a facial expression or something in between. And then I use that and share back with them. So it becomes this, in a positive way, this infinite hall of mirrors of mutual reflection and being affected by each other's reflection because the barrier between us has totally disappeared. And we are just a part of each other. That's dope. Yeah, that is by far the best feeling that I have had, can have, and can aspire to have again.

Baratunde Thurston, thank you for joining us.

Thank you for having me, Alex.

You can learn more about Baratunde's work and subscribe to his podcast, How to Citizen, at baratunde.com. We'll leave that link in the show notes. Talking to Baratunde felt refreshing. Like me, he's curious about how the shifting tech landscape is changing the ways we work and connect to one another. After we spoke, I wanted to hear from someone who could help me understand some of the bigger trends we're seeing in this space. As a culture, are we actually becoming more thoughtful about how we relate to technology? We sat down with Hannah Thomas-Uwase to hear her point of view. Hannah's a consultant who's worked with teams both large and small to help them find more strategic, more efficient, and more caring ways to incorporate technology into their businesses.

I think there is a through line between small businesses and, and big businesses when it comes to technology, and it's just thinking about relationships instead of technology. It's a two-way channel. And so I think that at scale, if you can replicate the quality and the nature of the intimacy of a one-to-one relationship, then that is what is going to stand you in good stead. If you can strike an authentic tone, then I think that's what reaches people. It might be useful to think of more holistic sets of metrics. So it might be better to have 100 people read your article all the way to the end instead of trying to get 1,000 people to click on it. My one piece of advice for people wanting to have a saner relationship with technology is just to be really clear about your purpose and why you're on it, and not to be distracted by what the platforms want from you. I think that's a really good point. When you're scrolling or just doomscrolling, you're working for that company. You know, you're not working for your own company, you're working for that company. When it becomes extractive, then stop, you know. In order to have a more holistic sense of well-being when we're interacting with technology, it might be useful to think about What experience do you want from your working day? You know, is a measure of success that you can find an hour in your day to write, for example? Or is a measure of success that you can get up and have a bath and then start at 10 instead of 9? You know, and to really, like, formalise those metrics for yourself and your team, and use those as part of your intention setting.

That was Hannah Thomas Uwase. Moments that jumped out to me when talking to Baratunde and Hannah were that there's a lot of conflict in building a business on social media because there's a lot of pressure to be everywhere at once. But as we all know, that's almost impossible to do. So it's important to consider this as we build more tech for the future, especially if we plan to build more sustainable models. I hope this episode has I hope this has inspired creative entrepreneurs to think about what that can actually look like in daily life. This has been Making It, an audio series from Squarespace. If you're commuting right now and not able to take notes, we've got you covered. You can find links, extra resources, And a way to communicate with us in our show notes. If tuning in has taught you something today, spread the knowledge. It'd mean so much to us if you take a moment to share your favorite episode with your friends. This show is produced by Work by Work and Squarespace. Scott Newman, Gemma Rose Brown, Jenny Mills, Emily Shaw, Kevin Abapor, Benjamin Shapiro, Kate Newman, and by me, Alex Wolff. Thanks for listening. The show is mixed by Sam Bair. If you're interested in hearing more conversation about the intersection of tech and culture, check out my handle on social media @AlexWolf. Thanks for listening.