Unlock the Power of Words in a Digital Age: Writing, AI, & Startups | Thomas White | Glasp Talk #23
This is the twenty-third session of Glasp Talk!
Glasp Talk delves deep into intimate interviews with luminaries from various fields, unraveling their genuine emotions, experiences, and the stories behind them.
Today's guest is Thomas White, an accomplished writer, investor, and advisor who has made significant strides in the tech and startup ecosystems. Thomas is the founder and CEO of Battle Media, a communication consultancy, and has been a guiding force behind numerous startups through his advisory roles at several venture funds. With pivotal experience at Google, where he contributed to product strategy and innovation, and as a former mentor at Google for Startups Accelerator Programs, Thomas brings a wealth of knowledge and expertise.
In this interview, Thomas delves into his journey as a writer, his philosophy on writing and editing, and his unique approach to capturing and articulating ideas. He also shares his thoughts on the future of AI, the importance of authentic intelligence, and the challenges facing humanity in the digital age. Join us as we uncover Thomas White's inspiring path and his profound insights into the worlds of writing, technology, and startup culture.
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Transcripts
Glasp: Welcome back to Glasp Talk, we are excited to have Tom White today as an accomplished writer, investor, and advisor who has made significant strides in the tech and startup ecosystems. Tom is the founder and CEO of B Media, a communication consultancy, and has been a guiding force behind numerous startups through his advisory roles at several venture funds. His experience includes pivotal roles at Google, where he contributed to product strategy and innovation, and he was a former mentor at Google for Startups Accelerator Programs. Besides that, he has delivered an amazing TED Talk on his journey with Tourette syndrome. Tom's work has empowered countless founders and firms to articulate their visions and drive success. So today, we are excited to dive into his insights and experiences. Thank you for joining us today, Tom.
Thomas: Thank you, Glasp team. Thank you, Kazuki and Kei. I'm excited to be here. And I don’t know about “accomplished writer”—definitely a writer. I hate to even call myself a writer, but “accomplished writer,” I don't know; that remains to be seen.
Glasp: Yeah, yeah. We love your writing, and we've been following you. We're huge fans of yours. So yeah, first of all, you are a writer, but we're curious—what made you become a writer?
Thomas: I was always good at writing, and I always knew that I was good at writing, but I don’t like writing, ironically. I don’t like writing; I like having written. I like hitting “publish,” sending the post, or my thoughts. The best part of it for me is taking these unintelligible thoughts in here and translating them so other individuals can read them, understand them, perceive them, and make note of them, right? So the process of writing is not a fun one, but when you nail it, when you hit just the right word, the right note, the right sentence, it’s like golf, right? I can swing a club multiple times, and oftentimes I’m not going to hit anything close to the perfect shot, but when I hit that perfect shot one time out of a hundred, that’s the addictive feeling I keep coming back to.
So, I knew I was always good at writing when I was in elementary school, high school, and grammar school. I did not want to be a writer. I think writing more comes from compulsion than desire. Like, I write because I need to say these things because it helps me make sense of the world, and update who I am, what I am, what I believe, and why I believe it. The only reason I started sending my stuff out publicly was as a forcing function to keep me honest, right? Because if I just took it and put it into a file on my computer or on my desk or whatever, I’m lazy, and the last thing I want to do after a long day’s work is to write, to think, and to try to extract ideas. So publicly sharing forced me to move my adherence from my own expectations to other individuals’ expectations. By doing that, I’ve been able to produce pretty consistently over the last four-plus years. It’s been a slog, but knowing what I know now as it pertains to writing online and sharing who you are, what you believe, and why you believe it, I wish I had started ten years ago as opposed to nearly five years ago. It has changed my life for the better, and it has accelerated my personal and professional career in wild ways. It led me to where I am. I stumbled into this role—writing, ghostwriting, editing, and being a communications adviser for a wide variety of startups. So, I never planned on it. I still recoil when I call myself a writer; I don’t feel like I’ve earned that title, which is a weird thing to say, but I think that’s common to a lot of writers. But it was a happy accident, and I stumbled into it. This was never the plan, and I feel like that’s most people’s careers, right? You make plans, God laughs, and then you end up where you end up. So I can’t complain. It’s a lot of fun, and I get paid to discuss, distill, and disseminate my ideas, that’s a dream because I’m a nerd at heart, I’m super curious, and I love talking to interesting, intelligent individuals like you two.
Glasp: Thank you so much. We found many inspiring quotes and interesting ideas in your writing, and we are curious—how do you get the ideas or keep the ideas? Do you use any tools, a workflow, or something?
Thomas: Yeah, it’s not pretty. For me, a lot of individuals don’t have an idea problem; they don’t have an idea generation problem—they have an idea capture problem, right? I write everything down, whether it be pen and paper, my calendar, or my email. I don’t overcomplicate it. A post usually comes from an idea I have in the shower, on a walk, working out, or in conversation with someone. I will take that seed, let it germinate, and then I will have a lot of different sentences and quotes and excerpts and different things that I accumulate. It could be over a day; it could be over a couple of hours; it could be weeks; it could be years. There are drafts—I have over 160 drafts in my newsletter dashboard, some of which I’ve just been working on for a long period of time, and I’ll put a little bit here and a little bit there. It’s like how a bird assembles its nest—taking all these random things, and putting them together. Initially, it doesn’t really have a form; you don’t know what it’s going to be, but over time it becomes a sort of home, takes shape, and protects and nourishes. That’s my approach.
So, it’s less about sitting down and hammering things out in front of a white screen and a blinking cursor. It’s more about assembling all these things, having all the puzzle pieces in front of me, and taking the different snippets, sentences, and paragraphs that I’ve written and ordering them so that there’s a cohesive narrative and I go from point A to point B to point C to say what I’m trying to say. I don’t use any interesting software like Notion or Roam or anything. I use email. I email myself—it’s super basic and super easy. The title is the subject line, and then it’s just different things that I’ve written, copied, pasted, and sent to myself. So it’s not rocket science; it’s very messy, candidly, but it’s been working for me because what I found useful is that you want to decrease the friction between getting the idea out and putting it down on paper because inspiration is fleeting, and the way that you think something or say something for the first time or write it down diminishes over time. So you want to capture it while the iron is hot and strike while that iron is hot as well. I don’t recommend it—my system is very disorganized and all over the place. I mean, I have a pen and paper here where I’ll jot things down as well as I come to them or when I have conversations with folks. So I don’t recommend it to others, but it’s worked for me.
Glasp: Thankfully, it’s all email, so not like a physical notebook or memo?
Thomas: No, no, notebook as well—physical notebook right here too. They’re everywhere; it’s like a disaster.
Glasp: Okay, so do you remember what you’ve written before in the notebook? Because it’s so hard to search for it.
Thomas: Yeah, I mean, do I remember what I’ve written? No, I don’t remember what I’ve written. I don’t remember it. Once I’ve written it, I’ve read all my posts like, I don’t know, 15 or 20 times just to get the right word choice, punctuation, beats, and rhythm. Once I publish it, I really don’t want to read it because I’m sick of the post. It’s like, alright, let me get it out there. So I don’t remember it. If I don’t write it down, I don’t remember it. Writing these ideas down, writing these sentences down, writing these fleeting bits of inspiration down is the only way that I’m able to retain all of this and actually put a piece together, as opposed to trying to rely on memory or rely upon an idea or something that I thought of a couple of weeks ago while walking or in the shower that is all but gone just because of everything that has happened since then. So it’s not the most organized situation, but writing... I don’t know, I think writing is supposed to be hard. And that’s one of the sad things about AI. AI is making everything easy; it’s like an easy button for everything. But oftentimes, the struggle to articulate yourself in written phrases, in verbal phrases, clearly and concisely—that is critical thought. And that critical thought drives everything from business to relationships to politics and everything of that nature. So I’m kind of all over the place in my answers, but hopefully, that’s interesting.
Glasp: It’s really interesting, yeah. But any difference between the things you write in an email and...?
Thomas: Yes, I edit it insanely. Writing is easy for me; I’ll write things very quickly. Editing is where I spend so much time. There’s a post I wrote about the 3-2-1 rule: you should spend three hours thinking about something, two hours writing it, and one hour editing it. I’ve since inverted that—it should be the 3-1-2 rule: three hours thinking about something, one hour writing it, and two hours editing it so that you nail the right messaging. Good writing is just great editing. It’s taking the first draft—I mean, I don’t know, I think Hemingway said it: “The first draft of everything is shit,” and I firmly believe that. When Stephen King writes a sentence or when Annie Dillard or Barbara Kingsolver or any of these titans, exceptional writers—the first time they write anything, it’s probably just as bad as what you or I would write. But just like with business, just like with writing, just like with professional sports, those people are willing to sit with it for longer, be consistent with it, and suffer for a longer period of time than the average man or woman.
So, what is in my email and what is on my calendar is so different from the final polished phrase. It’s like taking a diamond, mining it, shining it, putting a lot of pressure on it, and then it actually gleams. Like the crappy rock that you see—it’s really funny. Sometimes it’s just misspelled words. Sometimes I don’t include a verb—I just put a string of words that I refer back to just to kind of jog my memory. It’s very disorganized. Very seldom do I take a line for line and word for word what I’ve written as notes and set it right into my writing.
Glasp: I see, and I think this is kind of a forever question to writers, but how do you decide, “Oh, this is ready to publish”? You know, you could edit all the time if you have time, right?
Thomas: I get sick of it. I think at least at that point in time, I’ve thought of every word, and everything can be better, right? Like, every book’s a failure, as Orwell said, because every single book could be better. Which is one, really difficult thing to internalize, and it’s kind of discouraging. But two, when I’ve read aloud and I think that every beat, rhythm, measure, word, punctuation mark, etc., are in the right place, I’ll just send it out. Done is better than perfect, and you’re never going to get to perfect. Typically, when I send my stuff, it’s when I’m sick of it. Because people are giving me their time to read my stuff, consider my ideas, share it, forward it along, or what have you. So for me, I’m not going to do a disservice by giving someone garbage to read. I’m going to put in the hours because I don’t want to waste their time because time is the one thing that we don’t have enough of, and two, we can’t buy more of. So typically, when I’m sick of it and I think it’s worthy of another person’s time and attention is when I know it’s ready to go. Otherwise, I’d be spinning my wheels forever, tweaking this thing and that thing and what have you. Done is very much better than perfect, and a lot of people don’t even start writing because they let the mountain of perfect daunt them, and scare them, and that stops them from even starting, let alone beginning the journey.
Glasp: I see. And also, for your writing, do you use any AI tools for brainstorming, research, or editing?
Thomas: I’ve tried because I’m lazy. Oftentimes, when I use AI, or I’ve tried to use AI, I spend more time editing and rewriting than if I had just done it myself. AI is mechanical. I think artificial intelligence is aptly named because it’s soulless and mechanical, and it is just pattern recognition writ large based on large language models and tremendous amounts of data. For me, I prefer authentic intelligence which is blood, sweat, and tears, and the suffering that comes from an idea that is deeply embedded in someone’s heart or soul or mind, and they’re trying to extract just so that someone can feel what they’re feeling or understand what they’re trying to say or be inspired by their words or what have you. So I’ve tried almost every AI tool in the book. Again, it’s funny—I work in tech, but I’m kind of a Luddite. I need less and less. I need my word, my phrase, and everything of that nature.
Glasp: I see. And at the same time, I’ve read your book, Nobody’s Success and you said 46%—50% of Americans don’t read in a year. Meaning, do you think people… I mean, you know, people watch videos on TikTok, and YouTube nowadays, and other media formats are spreading over the world because it’s easy to consume for some people. Do you think…?
Thomas: Look, I don’t have to read; I don’t have to look at the word; I can just sit back, and this blow of senses can hit me as opposed to reading, which is an active activity. You have to remember where you are on the page; you have to actually actively go from line to line as opposed to the video just kind of coming at you. That’s… again, it’s a tragedy that more people don’t read. But sorry to cut you off. Go ahead.
Glasp: So I wanted to ask, do you think people will keep reading text, or how do you think people will consume information in the future?
Thomas: Thank you, that’s a really good question. I think about the Lindy Effect—things that have lasted for a long period of time have a tendency to last even longer. A book is one of the most antifragile, resolute, and oldest forms of technology. A book is a technology. So I think the written word won’t change much, the spoken word won’t change much. I think it’s where we meet that information, so as to ingest it, that will. Soon, we might… it might be like The Matrix where Neo can just pop in the cartridge like, “Oh, I know Judo now,” or “I know Kung Fu,” or what have you. That might be the case. But that easy button of everything, and the amplification of everything, I think is a really… it kind of hollows the hard work and effort that individuals do in order to understand or become a master of a subject or what have you. Like OIC, it feels like cheating, right? Like, I’d love to be on OIC; it’d be super, but it feels like cheating. But so, in a culture like that, where everything is a click or a pill or a post or something away, I think that really deadens and hollows out what it means to be human. And I think we’re going to have to seriously consider what humanity is, why it matters, and how to retain that as we go into this brave new world where machines will think better, work more quickly, and be more efficient than we are in a lot of ways, shapes, and forms. But what does that mean for humanity? What does that mean for the soul? What does that mean for friendship faith and human connection? We’re already seeing individuals who are relying upon AI chatbots for romantic partners and therapists—that’s really, really dangerous to me.
So I think the means by which we ingest information won’t change, which is to say written text via our senses, right? That’s the only way, as far as I know, that we’re able to pick up and retain information. But the modalities and media that we use to transmit that information, I think that will change. Like Apple Vision Pro, for example, versus an iPhone, right? They’re fundamentally the same thing; it’s just that one is goggles strapped on your head and another is in your hand.
Glasp: I see. Also, in your blog, I found really interesting quotes like, “We are drowning in information while starving for wisdom.”
Thomas: Yeah, that’s from… I wish that I wrote that. It was from E.O. Wilson, who’s a… like, a sociologist, I think? Yes, biologist, yes.
Glasp: Yes, and do you think that will keep happening to us?
Thomas: Yes, 100%. We’re… I mean, there’s so much information to the point where the answer to any question you could ever want is literally a query away. It doesn’t necessarily mean it’s the right answer, but an answer is right there. Versus in medieval times, or even pre-internet, I could look up the market for local journalism or the revenue that X company or Y company made from a supercomputer in my pocket. At the point where those answers are instantaneous and they are everywhere, the questions matter more fundamentally, right? So I think the future is more a problem of curation as opposed to creation because there’s too much data out there. More for… I mean, another quote that comes to mind is, “We have Paleolithic emotions, medieval institutions, and god-like technology.” And those three things are not compatible. Our lizard brains are not fit to digest and make sense of and retain and distribute all the information that is created in a minute on the internet, which is like hundreds of thousands of emails and millions of text messages and videos uploaded to TikTok and YouTube and what have you. I mean, it’s a deluge. We are drowning in it across the board. And that fundamentally, I think, lends itself to getting more information, but information is not the same as wisdom. Just like data and insight are different, right? Data is, “Hey, revenue went from $200 million to $250 million.” The insight of that $50 million increase is very, very different from the face value of data. I think we’re obsessed with the superficiality of information, and we risk playing in the shallows and not getting to the depth of wisdom. That’s my kind of thought about how we bring things through.
Glasp: That’s really interesting, but it’s related to the previous question. But yeah, so I think you have philosophy and vision for human society, AI, and software, but at the same time, you are investing in software companies or AI companies, right? So do you have any criteria for investing in those companies?
Thomas: Those companies that are pushing the envelope as it pertains to AI and humanity and stuff like that? Or is that the question, or investing across the board?
Glasp: Okay, so yeah, like, of course, financial return, but besides that, do you want to support those founders you are resonant with, those missions, or something like that?
Thomas: Yeah, for me, the way I think about it is… and I’ll do startups. Startups are very different from public equities. Public equities, you have information, a lot of that is priced in, there’s not the information asymmetry, because theoretically all that information is available to every investor in every market across the board, so it’s “priced in.” There’s a lot more asymmetry in early-stage companies, and it’s more reliant upon paradigms and frameworks and things like that as opposed to data or revenue or anything of that nature. So for me, at the earliest stages, what I focus on is the team, the team, the team. You need the right jockey riding the right horse—jockey being the team, horse being the product or service—running the right race, which is a market that is big enough to justify the risk that you are taking by investing in a startup that is 90% likely to fail, just given the law of averages and what have you, right? So for me, it’s the team, the team, the team. You can replace the product, you can pivot the technology… YouTube used to be, I think it was like a location services company or like a dating app. I think Tinder was location services as well. All these companies started as something vastly different. If you are able to pivot, and if you are able to be an entrepreneur who is willing to suffer and willing to have a heavy dose of resiliency, you will succeed. That can’t be taught, that can’t be replaced, any more so than a viral product can be replicated in some way, shape, or form. The team for me is everything. Because startups are very, very hard. I have to tell you both, that my favorite quote about startups is from Sean Parker: “It’s like chewing glass, but eventually you like the taste of your own blood.” That is very, very, very true. And it’s like writing, right? You don’t necessarily want to do it; you feel like you have to, you’re compelled to do it, you have some vision or some force in the future and you want to take that vision and make it a reality, whether it be on people’s phones or in people’s hands or what have you. That’s a very, very real calling. So I want those individuals who are obsessed with that, who have some unique unfair advantage that makes them the best person to build or scale a product or service. And I want someone that is resilient and comfortable with suffering, because there’s a hell of a lot of suffering, not just in life but especially in startup life. Like, if you go get a cushy job at a big corporation, it’s like playing life on easy. And that’s unfair, but I’m just going to extend the metaphor—if you’re going to found a startup or work at an early-stage business, that’s playing life in expert mode. There are no rules, there are no processes, there are no systems, you’re wearing every hat in the business, and you are trying to literally put a dent in the universe by creating something that was not there. So, those are the types of founders I like to get behind. Ideally, financial outcome—like, you invest, so I give you $1, you give me $2—you want an outcome like that. However, the law of averages and the base rates are such that the vast majority of these companies are going to fail. But ideally, you’ve invested enough into the successful companies that they will pay for the failures in dividends and more.
Glasp: I see. And I read your blog—we read your blog, Making Use of Nonsense, and that’s one of my favorites. And I love your philosophy of helping people who help others.
Thomas: It’s simple, it’s super… I mean, life is very simple. I’ve said this so many times—life is super simple, but it’s not easy. And oftentimes it’s not easy because we tend to overcomplicate ourselves by chasing the wrong things, focusing on different areas and concerns, and this, that, and the other thing. Like, you don’t need much to not only survive but to truly live and live happily at that. Just…
Glasp: Yes, I see your point. And yes, but from me, you know, I saw your list of investments, and it seems like you invested in many product communities like Inter, Recollect, Circles, BookClub, and Intero. Do you have the kind of themes or topics you usually invest in or are personally interested in?
Thomas: For me, it’s mostly boring businesses. Those businesses that are not competitive, that are not very sexy. I’ve been burned when I’ve invested in sexy consumer apps and things like that. One, that’s super competitive; two, everyone wants to build a consumer app. Very few individuals want to build a CRM for plumbers or something like that, or, I don’t know, something for morticians or what have you. So I’m opportunistic in terms of what I like. I’ll invest in anything as long as I understand it. If I don’t understand it, I will not invest in it—that’s the first condition. Secondly, the more boring, the better. The more esoteric and niche and weird it is, the more excited I get, which is ironic given I’m an extrovert. I love to talk about what I’m doing and what I’m interested in and things like that. That’s the second part. The third thing is founder-problem fit. Like, why is this person, this founder, and the team that he or she has recruited and surrounded themselves with, the right person at the right time to do this, right? Like, why is that person, that kind of force of will, going to win as opposed to the countless other individuals that are super talented, super driven, and super motivated that can easily—not easily, but can attack this problem as well.
Glasp: I see, that makes sense. Switching back to the topic of writing, I love the phrase “The pen is mightier than the sword,” and I love the quote.
Thomas: Totally, yeah.
Glasp: But I’m curious when you help others, you also help others, right? Or how do you crystallize ideas? When you help others, how do you… where do you begin with? Do you understand the story behind it and then synthesize ideas? Or have you found any common thing people struggle with when writing?
Thomas: I think the first rule is to tell the truth. If you tell the truth, you never have to remember anything. And I think a lot of individuals don’t say things or don’t express things because they are scared of what they might say, even if it’s something banal or annoying like a startup or business or what have you. If you tell the truth and if you’re vulnerable and you’re honest about what you discuss, why you discuss it, why it moves you, why it motivates you, one, that’s going to make you connect with other people more easily, and two, you’re not holding anything back, so you don’t have to be protective and you can get into deep conversation and vulnerable interaction, and that’s what it means to be human. My favorite quote from C.S. Lewis is, “Friendship goes from acquaintance to friendship when one person says to the other, ‘Oh, you too? I thought I was the only one.’” And that’s where they go live and they move more closely in this kind of immense solitude, he says, that we call life.
So I think the way I approach it—it’s very different. I’m kind of like a personal trainer. I’m not needed by any of these individuals per se, particularly when I’m working as kind of an intellectual consigliere, a communications adviser. They’re the knife; I’m the sharpener. The way that they use me, they are going to dictate and determine. But my goal is to make their thinking more robust, their communications more clear, and their messaging more consistent across the board—oral and written—and also in all correspondence and what have you. For some individuals, that’s high-level advisory. For some individuals, I get in a call just like with you guys, we’ll discuss an idea, I’ll record the conversation with their permission, and afterward, I’ll listen to it, I’ll take different tidbits, and then I’ll get all the puzzle pieces I need to be able to write a piece about, “Hey, this is why X is important in a time of Y, and this is the ideal reader for it, which is XYZ person somewhere and somehow.” So look, there are many roads to Rome, and there are a lot of different ways to bake the cake or make the sausage, so to speak. For me, it’s a matter of knowing what the person wants. Like, do they want to improve their communication? Do they want their communication done for them, like do they want ghostwriting? Or do they want communications coaching and consulting? Or do they want kind of a thought partner off of which they can riff, send ideas, and better refine their product strategy or their go-to-market or even just their messaging to potential customers? Because, I mean, first-time founders obsess over the product, and second-time founders obsess over distribution. And another quote, because I’m full of quotes and that’s all I do is just steal quotes, is “The universe isn’t made of atoms; it’s made of stories.” People do things because of stories, seldom because of reason. They will justify it to themselves using reason, but they will be motivated emotionally and psychologically via the wiring in our minds by stories. Because that’s what it is to be human, is to be a listener to and teller of stories. And everyone has a story to tell, and everyone has an important story to tell at that. Because my life is different from yours, different from the next person, it’s different from my brother’s, etc. Like, everyone should tell their stories because even if it’s to one person, you could change a life in that way, in a way that inspires or helps or says, “Hey, I’m not alone. This person gets it,” or “That guy gets it,” or “That girl gets it.” And that’s incredibly powerful, particularly in a world where—we’re so hyperconnected, but we’re not actually communal, and friendship is waning in a world of hyperconnection and superficial interaction, as opposed to, “Hey, let’s get into a real conversation, or the heart of the matter, or what have you.”
Glasp: I see. By the way, we found very interesting quotes in your writing, like “29 Reasons for 20 Years” or “old the blog.” How do you… how do you get the quotes? I mean, do you… from the books?
Thomas: I read all the time. I read any quote I like, I’ll take it and put it in a big repository file that I have. And sometimes I know, like, “This quote is going to go in this piece when I’m talking about that.” Other times, it’s like, “Hey, the way that was said was really beautiful and wonderful and it moved me in some way.” I’m just going to put that in my back pocket, and when the time is right, I’ll pull it out and be good to go. So, I read all the time. Another great idea is to be a good writer, you have to be a great reader. You have to read, and you have to expose yourself to a lot of different styles and sentences and paragraphs and facts so as to build a latticework of mental models to make sure the world makes sense around you. Because a lot of people, like, they like to think that they’re thinking, but they’re actually just rearranging prior opinions and prejudices and things like that in their head. Critical thought is not only admitting you’re wrong but being happy to be wrong because you’ve gotten closer to capital-T Truth, which is very different. And I fall victim to it; everyone falls victim to it. Right? Like, theoretically, if you are a lover of truth and someone puts you back on the path towards truth, you should be happy. But individuals like being right, being heard, and being themselves more than they like truth. And I think that’s a very dangerous proposition when, you know, individuals can no longer agree that the sky is blue. It’s like, “Hey, the sky is blue.” And you could say to me, “That’s your opinion, my lived experience—the sky is green.” It’s like, objectively, that’s not the case, but we have to meet somewhere on solid ground. So, the long rant and diatribe, just how being honest with yourself and being honest with others is a great way for you to live life without trying to put on masks or be someone that you’re not. And a lot of individuals have a lot of masks on. And again, just because I’m saying these things doesn’t mean I don’t fall victim to them. I’m the most imperfect person around.
Glasp: Yes, thank you for that. And also, you know, we need to be good at grammar, right? I read your “How to Write Good,” and, you know…
Thomas: Yep, totally.
Glasp: You…
Thomas: I mean, if bricks are words, grammar is what holds all the words together. Otherwise, I could take a brick wall and push it down, but grammar makes it stand. And again, I’m a nerd for this stuff because it’s kind of like the seasoning on the meat that is the words. It’s what gives it flavor and structure and things like that. But yeah, I mean, it’s grout, right? Grout is grammar, and then the bricks are the words. You can make a brick wall without the grout, but it’s not sturdy at all.
Glasp: I see, yes. Yeah, so…
Thomas: Go ahead.
Glasp: So this is just a random question, but for a week, how do you spend your week? Like, from Sunday to Saturday, how much are you spending with your family? How much are you reading? How much are you working?
Thomas: So, I’m lucky and blessed enough to work remotely. I split my time between New York and Notre Dame, Indiana. So I’m in Notre Dame in the fall, the spring, and the winter, and then I’m in New York in the summer at a nice beach community in New York called Breezy Point. I live with my family during the summer. Typically, on weekends they’ll come down to the beach and we’ll all hang out together. My family is very, very important to me. My weeks… during the week, my workweeks are all over the place. It really varies. I’ll try to stack meetings—like today, I’ve had five meetings, but sometimes I’ll have ten or eight. It really, really varies depending on the time of the year—client work, thinking work, and things like that. So, all that to say there’s no one particular day in the life, like, I don’t have a routine. I think, one, I need a routine, but two, creativity doesn’t really work within the confines of a routine, which makes life a bit more difficult in that regard. The best ideas happen at the least convenient times—like when I’m swimming in the ocean or when I’m in the shower and stuff. It’s like, God, why couldn’t it just come when I’m thinking by myself? But fortunately, the brain doesn’t work that way. So typically, I work in the morning. I like to putter around; I like to think. I like to start meetings and stuff at 10:00 a.m. Eastern, and then typically I’ll work until, I don’t know, 8 or 9, with a break for lunch, with a break for walks and stuff like that. It really, really varies. The lucky thing about my work is that I’m my own boss, so I can be very, very flexible, and I can work on things when I want to work on them because I don’t know if you guys resonate with this, but to write, you have to kind of be in a mood, and it’s hard. Sometimes you don’t have it, right? Other times you’re in the flow state, and it’s great, and it’s pouring out of you. Other times it’s like hitting my head against the keyboard and hoping something good comes out. So as long as I’m diligent with my time and with everything, it’s about the outputs, not the inputs, so to speak. I travel all the time, love… I’m very blessed to have an incredible amount of family, friends, and colleagues, personally and professionally, that I really respect. But I’m a big wedding person. I have four more weddings for friends this year—there’ll be ten in the year in total. My biggest year of weddings, because I’m 32 now, was 15, which was absolutely insane and super expensive. And I love to ski in the winter. I try to ski as much as possible. I love, love, love to ski. That’s happiness for me—just being on a ski slope outside with family or friends and just kind of spending time there.
So I guess from that answer, you can take that there’s no typical week, there’s no typical routine or day. It’s very much varied. And that, I don’t know, it suits me, I feel like, because, one, I’m quirky, and two, I’m very, very curious. So if I get an idea, I can spend a couple of hours going deep on that idea and writing about it for myself or a client or what have you, as opposed to having to wait until a block of sales meetings or marketing meetings or internal meetings are done and having to repress that idea. Because again, you want to strike when inspiration is hot, and inspiration is very, very fleeting across the board in that regard.
Glasp: I see. Yeah, are you working on some ideas now, or do you have a kind of working topic?
Thomas: So much. I have so much stuff that I’m thinking about. Okay, I’m thinking about this—you can’t spell renaissance, you can’t spell renaissance without AI. Artificial intelligence, can mean authentic intelligence, it can mean addictive intelligence, it can mean actionable intelligence. So I’m thinking through… what do each of those outcomes look like, and what is the most likely outcome? Because AI, I think we can all agree, is going to change humanity in ways that we can’t even comprehend. How that happens, though, we have a very short period of time to dictate before, you know, superintelligence and the alignment and singularity is achieved. And we’re like playing basketball against Michael Jordan, right? Losing every single time. So that’s one. A second is… and this is still… I’m still thinking about it, but content creators, like the influencers and all that garbage, they hurt the internet. AI is actually going to kill the internet. And the whole thing is, the kind of garbage content that first started as a formula from the influencers and the creators—the five things you need to know about X, like, these are the twenty things… all the listicles and garbage that individuals break their brains on. AI is trained on those models. And at the point where you no longer need a production team or a writing team or anything to create those, the internet is going to be so full of garbage that is trained on bad data—garbage in, garbage out. It’s kind of like a death spiral in that regard. So that’s another idea I’m thinking about—how thinking like, we’ll run out of data eventually to train these models on unless there’s some technological leap forward. And even before we run out of data, we’re trained on garbage data from influencers that simply because their messages reach the largest amount of individuals doesn’t mean that those messages are interesting or right or moral or even intelligent in any way. So those are the two things that I’m kind of thinking about. They’re hard planes to land in terms of the pieces, but I’m trying to put them down.
Glasp: Interesting. Do you have any discussion partners when you come up with some ideas, or can you think of them by yourself?
Thomas: Oh yeah, a lot of group texts, group text messages, phone… I have friends that I’ll call, like, “Hey, do you mind if I record this conversation?” because I’m trying to think through things. I’m lucky in that, one, I’m Irish-American, so I’m very extroverted and very social. And two, I have a lot of individuals who are more intelligent than I am, who are just as curious, that I can use to riff with or bounce ideas off of or just ask questions to see if I’m thinking about… or if I’m missing something in my analysis, thesis, or if I’m thinking about things in a relatively, you know, correct, at least directionally, way.
Glasp: Makes sense. And yeah, so, by the way, I think the time is running up, and this is the last question. Since Glasp is a platform where people share what they’re reading, and learning, and the highlights, and sometimes quotes, inspiring quotes—meaning we see that as a digital legacy—people sharing the details, we want to know, what kind of legacy or impact do you want to leave behind for future generations or others?
Thomas: It’s a heavy question.
Glasp: No, I mean…
Thomas: I think it’s a heavy question, but it’s a simple answer. I want to be known as someone who is kind, and who treats individuals with respect. Loving… loving, you know, God willing—loving father, loving son, loving friend. Someone who radiated kindness and showed up for individuals when they needed him there. Because that’s what life is, right? I just want to be known as kind and as a good person. I don’t need any trophies; I don’t want any laurels or anything like that. Just be kind. That’s what it comes down to. It’s a simple answer to a heavy question, but I think, again, a lot of life’s answers are pretty simple. We get in our own way, and we trip over ourselves trying to chase the Rolex or the Lamborghini when all you really need is a kitchen table and a nice home-cooked meal with your family.
Glasp: Totally, yes. Again, thank you so much for taking the time. We really learned from your insights and experiences and enjoyed the conversation.
Thomas: Thank you so much. Totally, I loved it, and I’m excited to see this live.
