This book project requires an extensive research process. I plan to conduct many interviews with writers, influencers, and entrepreneurs. The interviews will all be public and will live right here on my website. We’ll go on this journey together — you and me. Together, we’ll cross industries, speak with experts around the world, and explore the past, present, and future of Naked Brands.
Dan Runcie is a writer who covers the business side of hip-hop culture. While traditional media outlets often scratch the surface on hip-hop business, Dan’s Trapital newsletter digs deeper. Each story breaks downs and identifies the strategic moves that shape the culture. I would recommend signing up for his Trapital newsletter.
DAVID:
First and foremost, before we begin, I want to say that I love what you’re doing at Trapital. I think it’d be interesting to start off by just how you see the role of musicians evolving, like in my survey of the landscape, musicians are no longer just musicians. They’re top of the funnel marketing properties. They’re doing so many other things besides music. How do you think about that? I think you’re right because, in the beginning, they could just care about the art of making music and not worry about anything else, but today as individual branding and personal branding is becoming a thing, there’s just so many more opportunities to be able to make off of the work that they’re doing. Thinking beyond working directly with the record label, thinking beyond just touring it, trying to find the best ways that not only makes sense for the industry makes sense for them too. I think we’re seeing the music industry is becoming more fragmented where artists can have specific rates that they charge us to really do what they want to do.
DAN:
I think we see that most strongly now in hip-hop. If you want to focus on building a very focused group of fans like J. Cole or Kendrick, you want them to support you forever. I think we’re starting to see that business models are becoming more fragmented and I think it’s presented more opportunities, but it’s also presented a bit more challenges, like playing by the playbook and thinking of how they want to make money.
DAVID:
Yeah. Interesting to hear you talk about Kendrick and I know you’ve written a lot about Drake. How do you segment in your own head, the different kinds of business models? People like Drake, I remember a couple of months ago that his face was literally on every single Spotify playlist for a week and then you talk about people like J. Cole who has much stronger fan bases and fans for life. How do you think about the different segments of hip hop business models?
DAN:
So in one of my recent articles, I compared Drake to having a Walmart and Procter & Gamble type relationship with streaming companies. And ultimately how he’s trying to put out this music that can reach the masses. So by design, he wants to make sure that he is going to be as ubiquitous as possible. And that’s why to me, there was no surprise when he was literally on Spotify playlist. He’s the biggest entertainer that we have right now. And I think frankly it’s working for him pretty well. n the flip side though, I look at a Kendrick Lamar, or a J. Cole. They flip the script and say, okay, we want to still try to put out the best quality work that we can.
This is what we want to do and we want the fans and the culture to recognize this. They are not on the same like annual summer cycle that Drake is. They’re taking their time and their fans appreciate it. People are willing to sit down and wait for it. They really do see these guys that try to set themselves apart and not just being part of a larger machine but building and cultivating fans and truly making a name for themselves where others aren’t.
DAVID:
It seems like Drake is just the ultimate social media mastermind. Like when I think of Drake, I think of The Gift, just like this kind of business model, is an emergent social technology that was born out of social media. Then also he teamed up with Apple Music where I know his songs over-index in popularity. If you look at Drake and you look at the Internet and you look at culture and where that’s moving and how messaging and media is changing. What have you learned from Drake that you think he’s doing really well?
DAN:
I think Drake specifically, he does a very good job of being able to control the media narrative and make people think that they want to think about him. He knows that if he dropped a single or he has something like that Hotline Bling music video, those things are pretty calculated. I think he knows how to own and dominate the competition more than anyone. It all stays current, too.
DAVID:
It feels like the Internet basically elevated in hip-hop music in a way that it has elevated any other genre. What do you think it is about the Internet and the way that media is changing, which is given disproportionate influence to hip-hop? It feels like hip-hop is a genre of music of our time that is enabled by the Internet. Why do you think that is?
DAN:
Yeah, I think we definitely see a wave of hip-hop as you mentioned. There’s a comfort and there’s a reinforced acceptability that’s happened to make yourself a brand and to make yourself stand out that I just don’t see in other genres. They’ve done this in the NBA as well. A few NBA athletes have done a fantastic job with being able to brand themselves.
I listened to the Bill Simmons podcast and he always has this joke where he says, who’s the best baseball player right now? Let’s say it’s Mike Trout. How many people can walk down the street and recognize who Mike Trout is, right? But if the 10, 15 best NBA players walked past you, you’re recognizing them, and it’s not just because of their height. Like if Chris Paul or Steph Curry walked past you, you’re going to recognize that and I think it is the same type of thing with hip-hop culture compared to these other sports. I think there’s a comfort with being able to brand yourself.
DAVID:
That reminds me of an article I wrote recently called Naked Brands: The Future of Basketball. As you mentioned, basketball players don’t wear helmets and the court is super small, which makes the players recognizable.
So help me understand this because one thing that is a bit confusing to me is I very much see the music business as inverted. So music really used to be the bottom of the funnel where you would do a lot of advertising and people would buy your records and that was the way that artists make money. Pretty straightforward, but now I see music as much more of the top of the funnel and where music should be free and accessible as possible so that artists can maximize their reach. They can then monetize in other ways like events, like concerts. And one thing that I struggle with is when we talk about the business model for music, I think that so often the industry over-focuses on monetizing music itself, and not enough on complementary business models. And maybe it’s because we’re in a transition period.
DAN:
Yeah. I agree. And I think you hit the nail on the head. I wrote about this recently, once piracy and LimeWire and all that started putting pressure on the old model and then streaming took off and flipped everything. And you’re absolutely right. We are at the top of the funnel. I’ll still hear people complain about the pennies on the dollar that artists are getting from Spotify streams or YouTube and it’s like, I get it. You know, there’s a number of reasons for that. We don’t necessarily need to go into that with this particular question, but the more people that can hear your music that are in your group, the better off it will be for you because you could then make money from those people in a number of ways and I think the business model is showing that.
DAVID:
Absolutely, you know who’s doing really interesting stuff with this? Will Smith. He was an actor and he was also making albums. Like I remember having a song called Switch which was really cool and now he’s like a born again YouTube or an Instagrammer and when I’m looking at Will Smith, I feel like he has an intuitive sense of a lot of what you just said.
DAN:
Yeah, he really does. He’s definitely been successful in other areas and even with how he’s using his Instagram page right now is a wonderful marketing tool for him just to stay relevant. It’s so easy for a 50-year-old male actor to fall to the wayside, but he’s still putting out movies. But knowing how to market himself is always going to help people remember him. This guy used to get $100,000,000 every time he put out a box office movie, he could still do that. And this Instagram feed outlet, it’s a radar to keep that going.
DAVID:
Yeah, absolutely. I mean, I think there’s so much to learn from Will Smith and where things are going. I’m really curious to hear about like I think that there’s almost a medical question here in your analysis of the music industry and changing business models and he and yourself and your own business model using Substack newsletters to really target the business office and using in like Substack which are new and emerging and trying to curate an audience on your own. I think it’s really interesting to see these parallels were having a conversation.
DAN:
Yeah, definitely. Because I think with Substack and with what I’m planning as well, I knew that there was a niche and there was interest out there for people to want to better understand the business side of hip-hop. We’re just scratching the surface on hip-hop and business itself and as this conversation has shown, there’s as much strategic decisions and mindset that goes into hip-hop as there is in tech. As someone that’s worked in a number of different industries and has written about data for a number of publications, I really felt like it was a perfect way for me dive into it, tell the stories that need to be told. I think with putting my content out on places like Substack and meeting with the founders, getting a sense from what they’re trying to build as well. If someone can find a space that isn’t necessarily tapped into and be able to build a following and you know, getting the reach that they need.
DAVID:
The last question is, I remember thinking back on my childhood and in terms of my younger years back when Internet blogs were really popular like I remember a blog called This Song is Sick and a couple other blogs right? And a lot of artists when I was growing up and would come out with one song a week.
And I always remember thinking that that was clever. And you saw it much more with the up and coming artists. My question to you is twofold. 1 is, are there artists who were doing that sort of stuff now maybe coming out with 15 to 30 second freestyles on Instagram every Sunday, something like that. What sort of emerging strategies are up and coming artists using that the mainstream has been adopted yet?
DAN:
So these are great questions. There are two examples of those. So one is an artist named Russ, he had made his come-up completely independent on his own and he was putting out one track a week, the same time every week, every time. No different than you and I put it out our newsletters.
I think that serves him better than just doing a traditional album rollout, especially in the early days. And now he’s on the most recent top 20 Forbes Hip-Hop Cash Kings list that came out. The majority of people didn’t know who this guy was a few years ago. The second example is artists using Instagram. There’s an artist named Tierra Whack who put out one minute tracks that were all individual music videos, but she released them on Instagram.
But it’s interesting. I didn’t really see anyone do that and she’s a younger artist that I’d say is definitely making a name for herself. She caught a number of eyeballs and attention with that move. But it’s something I haven’t necessarily seen many other artists do. In a lot of ways, people will tend to follow Drake because he drives the culture. I think we’re probably still going to see quite a bit of people releasing, you know, 20 or 30 track albums to try to game the system. But I think the future of the path forward is like what artists like Russ and Tierra Whack are doing. How best can you be able to build a following in the same way that either other companies are trying to do it? Like how you would I do newsletters, trying to be consistent or leveraging Instagram the same way that brands are.
DAVID:
Right. This is really interesting. I have a comment and one last question with what came to mind as you were speaking. I think that the Internet content creators from musicians to writers, they’re really going to begin to follow a barbell strategy of staying top of mind with people and building relationships that feel as if they’re part of a routine. On the other side of the barbell is super in depth evergreen content that takes an angle or a perspective on a certain aspect of whatever they’re writing about. That is hands down the best thing on the Internet and that drives traffic over and over and over again and we’re talking about this and I very much think that artists in the future are going to maybe be posting something every day or every other day so that you’re opening Instagram and you’re expecting something new from that artist. But then, on the other hand, coming out with 20-30 song album that can stand the test of time. And you mentioned 20-30 song albums and you said that they were gaming the system. That’s really interesting. Can you talk about that?
DAN:
So I feel like I can definitely see artists trying to have that consistent model and focusing on the other side of the barbell. Back to Drake, the last thing he wants to do is put out an album and it doesn’t do as well as the last one did. The last one had 22 tracks and then this one has already 29. Spotify has grown its user base since the last time he put out an album, and because of that it’s almost a definite thing that he will continue breaking streaming records. So that’s what I mean by like gaming the system to your advantage. On the other side, Pusha T put out that seven track album earlier this year. Even though Pusha T isn’t on the same level as Drake, there was no chance for that album to break streaming records just by the sheer fact that it was 21 minutes worth of music on that seven tracks.
DAVID:
Yeah, absolutely. Well Dan, this was lots of fun. I always tell people to subscribe to your newsletter.
The future of holding companies will be built around audiences, not industries.
Today, many of the biggest direct to consumer (DTC) and digitally native vertical brands (DNVBs) battle for the same affluent urban Millennials. Silicon Valley marches to the beat of three words: Growth. Growth. Growth.
Billion dollar brands such as Jet.com, Bonobos, and Dollar Shave Club pioneered today’s venture-backed brand-building trifecta: hyper-growth, quality product, and customer data. Fueled by the scale of Facebook and Google, these brands have instant global reach.
Flushed with scale-hungry investors and oceans of venture money, DNVBs go to war for the same customers on the same platforms (such as Facebook and Google). Customer acquisition costs soar as they fight for limited advertising space. As companies grow, so do costs of acquiring each additional customer.
Customer acquisition costs are increasing exponentially.
Demand for advertising space outpaces the supply of it, which drives up prices. Facebook and Google are offering additional advertising inventory.¹ In 2016, we didn’t have ads between our Instagram stories, but today we do. Why? Because advertisers on Facebook and Instagram are happy when inventory expands and they can reach consumers. Since because Facebook commands the lion’s share of consumer attention and owns the real estate where they show ads, brands offer customers at higher and higher prices, as Mark Zuckerberg rakes in buckets of cash.
The DNVB space wreaks of high customer acquisition costs and smells like a bubble. As Chamath Palihapitiya, the former VP of Growth at Facebook, and now the CEO of Social Capital, observed about $0.40 of every VC dollar raised goes straight to user acquisition:
“User acquisition and growth has become such an entrenched part of the Silicon Valley zeitgeist. Unfortunately, today’s massive venture-backed advertising, sales, and user acquisition playbook has morphed into one that champions growth at any cost.
We have higher salaries, higher rents, higher customer acquisition costs, Kind bars, and kombucha on tap!”
Competitive bids for the same inventory, addressing the same audience, drive up demand for the same real estate within a feed or a story, causing ad prices to skyrocket.
Advertising on Facebook has become 70% more expensive between 2017 and 2018, while ad spend on Facebook grew 40% during Q2 2018.
In the words of Warren Buffett, this ruthless arms race is like a parade:
“One spectator, determined to get a better view, stands on their tiptoes. It works well initially until everyone else does the same. Then, the taxing effort of standing on your toes becomes table stakes to be able to see anything at all. Now, not only is any advantage squandered, but we’re all worse off than we were when we first started.”
There’s the current state of customer acquisition — a parade of brands looking to acquire every single customer individually.
On the internet, where attention is bought and sold like a commodity, the scarce resource has shifted from attention to trust. As Morgan Housel wrote:
“Marketing is increasingly cheap. Trust is increasingly expensive.
Attracting eyeballs no longer sets you apart. Building trust among those who have their eyes on you, does. Getting people’s attention is no longer a skill. Keeping people’s attention is.”
To decrease spending and increase profitability, the holding companies of tomorrow will shift their attention from controlling supply to controlling demand — from building around industries to building around audiences.
Re-marketing to an existing customer is significantly cheaper than trying to persuade a first time customer to buy your product — sometimes nearly 90% cheaper.² As Ben Thompson has observed, we’re shifting from a supply-driven world to a demand-driven world:
“The folks who win on the internet make the experience better. In the physical world, limited by scarcity, economic power comes from controlling supply; in the digital world, overwhelmed by abundance, economic power comes from controlling demand, and that control stems from a virtuous cycle that… accrues to the dominant player in a space.”
Companies who cater to the needs of passionate customers will benefit from lowered customer acquisition costs and higher lifetime value (LTV),reduced churn and increased loyalty. Once a paying customer is acquired, companies can cross-sell and up-sell them into different products, categories, and even brands. The fight to find thatcustomer will be much easier leading to an increase in transaction volume. As they reduce friction in the payment process and increase customer loyalty, they’ll accrue data behind customer cohorts leading to a customer-centric experience.
“Brands are irrelevant. The users are the brand. They are the CEO.” – Emily Weiss, Founder of Glossier
Roughly 80% of Glossier’s growth comes from peer-to-peer recommendations, and their main retail establishment generates more sales revenue per square foot than the average Apple store.
Sales and marketing are the lifeblood of any organization. Unlike many of today’s DNVB behemoths, their customer acquisition costs will decline as their balance sheets scale up and to the right. Instead of blowing cash on customer acquisition, DNVBs invest in brand experience to increase customer retention, loyalty, and peer-to-peer referral. Informed by data and dynamic feedback loops between customers and headquarters, brands like Hint and Glossier incorporate customer feedback and crowdsource brand extensions.
Companies who cater to their customers and develop direct relationships with them, will own the future.
¹ There are a finite amount of places an ad can be shown. Think about this in the sense of billboards: there has to be a limited amount of billboards; just like that, there’s only so many places the internet can host an advertisement.
² There are three kinds of marketing:
Prospecting — Going after a whole new consumer entirely. They’ve never heard of your brand.
Retargeting — Advertising to convert a customer who expressed interest, but didn’t complete their transaction.
Re-marketing — Advertising to your existing customer list to sell something else.
I once attended a comedy show with a group of friends. Since the venue was across town, we split an SUV. I sat in the back. You know… all the way in the rear, where the seats get so narrow that you have to do gymnastics just to get back there.
From the moment the driver hit the gas pedal, everybody was on their phones. From the back row, I watched my friends scroll their social media feeds with ferocious intensity. One thing stuck out: the people in front of me only consumed content created within the last 24 hours.
No exceptions.
I succumb to the same impulse. Chances are, so do you.
The structure of our social media feeds place us in a Never-Ending Now. Like hamsters running on a wheel, we live in an endless cycle of ephemeral content consumption — a merry-go-round that spins faster and faster but barely goes anywhere. Stuck in the fury of the present, we’re swept up in dizzying chaos like leaves in a gale-force wind. Even though on the Internet, we’re just a click away from the greatest authors of all time, from Plato to Tolstoy, we default to novelty instead of timelessness.
We’re trapped in a Never-Ending Now — blind to our place in history, engulfed in the present moment, overwhelmed by the slightest breeze of chaos.
Here’s the bottom line: How can you prioritize the accumulated wisdom of humanity over the impulses of the past 24 hours?
I have a confession to make: I used to eat a lot of fast food.
Wendy’s. McDonald’s. Chick-Fil-A. You name it. I ate it all.
There’s good news and bad news: The bad news is these decisions probably took years off my life. But the good news is they taught me a secret of marketing, which I’m going to share with you now.
I attended college in North Carolina. On school breaks, we escaped campus and explored the South by car. We visited all the major cities within a 500-mile radius of our messy dorm rooms, from the quaint streets of Charleston, to the peach trees of Atlanta, to the country music bars of Nashville. The drives always felt longer than they actually were. As the conversations slowed to a silence, we could hear our bellies growling. After a couple hours on the road, we had to stop for food. By the time our hunger set in, our headlights illuminated the asphalt in front of us, and stars dotted the rural Southern skies. Hungry — yet eager to reach our destination safely — we always ate at a chain restaurant. The speed of fast food was a bonus, but we cared more about the predictability of it; ambiance mattered, but we cared more about clean bathrooms; healthy options were nice, but we cared more about avoiding food poisoning.
I now realize that our restaurant decisions were driven by three ideas: (1) The Need for Common Agreement, (2) The Search for Safety, and (3) The “We Know it’s Going to Be There” Principle.
The Need for Common Agreement: We never pulled off the highway before agreeing on a place to eat. Crucially, we always agreed on the chain that nobody in the car disliked, not the chain that one person in the car loved. We usually stopped at popular chains, such as McDonald’s, where everybody already knew their order. Since we needed to reach a consensus, we optimized for “nobody is going to be mad about this decision,” not “this could be the best meal ever.”
The Search for Safety: Part of the appeal of the major fast-food chains is the bright lighting, clean bathrooms, and knowing that you won’t leave with food poisoning. They sell predictability. Even in the worst parts of town, McDonald’s is a safe place to be. McDonald’s doesn’t just sell food. It sells cleanliness, reliability and a predictable menu that’s consistent from store to store. Rural Southern towns can feel dicey after the sun goes down. Since we were out of our element, we always prioritized safety. Even if we had already agreed upon a restaurant, if the lighting was dim and the restaurant didn’t look clean, we’d call an audible and choose another restaurant.
The “We Know It’s Going to Be There” Principle: The fun of picking a restaurant always started with a conversation, not a Google search. Crucially, a restaurant suggestion would only be made if we assumed there was a location nearby. For example, we knew not to ask for Wawa south of the Mason Dixon Line or for Zaxby’s north of Georgia. Even if a location existed, it lacked density. In contrast, it felt like every highway exit led to a McDonalds. When we knew a chain was nearby, we were likely to suggest it. If not, it escaped our minds.
On the road, these principles mattered more than the food itself.¹
Chain restaurants don’t just sell food. They sell cleanliness, predictability, and downside risk protection. In short, chain restaurants are Satisficing Brands, not Maximizing Brands.
Maximizers seek the very best. When we act as Maximizers, we strive for outsized success.
We support Maximizing Brands when we’re outside of our regular routine. When it comes to wedding planning, or purchasing a high-end top coat, we pay hearty premiums to maximize the upside. Maximizing is why we pay exorbitant premiums for travel experiences, such as skydiving in Switzerland or climbing the Sydney Harbor Bridge in Australia. When people seek memorable, remarkable, or extravagant experiences, they become Maximizers.
Luxury brands are iconic Maximizing Brands. Luxury brands thrive in areas of high social and geographic mobility. In these areas, where we meet lots of new people, we use luxury brands to signal success, prestige, and identity. As Rory Sutherland, the first person to distinguish Maximizing Brands from Satisficing Brands, wrote:
“In China the luxury goods thing is very, very strong, firstly because large numbers of people are from out of town, secondly, often in China you don’t take people to your house — your status depends on the clothes you’re wearing, so luxury goods brands have a value in status terms to the Chinese that is far greater than it would be to most French people living in their ancestral home, for example. British Aristocrats don’t wear massive belts with “Moschino” on. No. If you’ve lived in the same house for 500 years, you don’t need to wear blingy clothes.”
Luxury brands are context-dependent. In small towns with low social mobility, where everybody already knows who you are, there’s no need for luxury brands. In fact, your propensity to support luxury brands is directly proportionate to the geographic and social mobility of the environment around you.
While luxury brands signal status and success, they represent a fraction of our purchasing decisions. Maximizing Brands dominate our attention, but not our wallets.
Most of the time, we care more about avoiding catastrophe than maximizing upside. Enter… Satisficing Brands.
Satisficing Brands: Fast Food Chains
When we talk about brands, we talk too much about Maximizing Brands and not enough about Satisficing Brands.
Most people over-estimate how much they maximize. Most of the time, we’re engaged in normal routine. We’re in normal places, doing normal things, and living a normal life. We have bills to pay, people to see, and commitments to honor. In mundane moments, which account for the majority of our lives, we don’t need something perfect. We just need something safe, simple, and reliable — a Satisficing Brand.
We pay premiums for “better,” and also, “less likely to be terrible.” Most of the time, we want the safe option, not the best option. We choose the safe option with low variance over the risky option with high variance. We crave certainty. We fear the unknown. All else being equal, we prefer to avoid losses than acquire gains. We care more about “unlikely to be embarrassing” than “potentially the best thing I’ve ever done.”
Satisficing Brands are more influential than we think. When we buy Satisficing Brands, we prioritize safety over perfection. Satisficing Brands aren’t sexy, so they escape our minds. Since they’re part of our daily routine, Satisficing Brands account for a disproportionate share of our purchasing decisions.
Since our safe, mundane choices are made on auto-pilot, we tend to underestimate how often we merely care about satisfaction, and thus, how often we support Satisficing Brands.
Pro-tip: Think more about Satisficing Brands, and you’ll instantly improve your understanding of branding and human behavior.
If you’re craving a Wendy’s Chocolate Frosty, my favorite college dessert, treat yourself and call it “market research.”
This book project requires an extensive research process. I plan to conduct many interviews with writers, influencers, and entrepreneurs. The interviews will all be public and will live right here on my website. We’ll go on this journey together — you and me. Together, we’ll cross industries, speak with experts around the world, and explore the past, present, and future of Naked Brands.
One of my favorite articles of yours is Decomplication: How to Find Simple Solutions to “Hard” Problems. Here’s the premise: the core solution to many problems are extremely simple. However, businesses create “artificial complexity,” and use it as a sales tactic. They take advantage of our desire for complex solutions to simple problems.
In similar fashion, professionals use jargon to simplify the mundane. Nevertheless, there is a simple solution to most problems, and we should strive to do what’s simple — not what’s easy. In an effort to leverage Google and earn attention, how can Naked Brands de-complicate the SEO process? Break it down for me.
NAT
SEO is really just about knowing what questions your customers or fans are asking, and providing good answers to those questions. As long as you can explain something in a useful, understandable, and actionable way, you can succeed with SEO. It’s really that simple.
Where most people go wrong is they don’t do a good job of answering people’s questions, or they provide content that answers questions no one is asking. There’s a place for non-SEO content, like your blog and most of my blog, but if you want your articles to drive business goals then you almost always want to focus on figuring out all the questions your potential customers are asking and provide the best answer to those questions that you can.
DAVID
Being a Naked Brand usually means working for yourself. It means being responsible for your growth, your learning and your reputation. You’ve used the internet to learn SEO from scratch and start a lifestyle business. What strategies have you developed to learn consistently and identify high-quality educational material?
NAT
My core principle for self-education (which I outline more here) is getting to application as fast as possible. You can’t really learn something by watching videos, reading books, listening to lectures, you have to do it, but we don’t grasp that as well in some areas (like entrepreneurship) the way we do in others (like riding a bicycle).
So whenever I’m trying to learn something, I try to actually start doing it as soon as possible, and then primarily use educational resources to troubleshoot problems I run into. It’s too easy to get stuck in the research phase forever without really knowing what you need to know, so I prefer to jump in and get my hands dirty and build the parachute on the way down, so to speak.
DAVID
Many of your clients are trust Growth Machine because they trust you. They follow you on Twitter and they’re fans of your writing. From a marketing perspective, how do you think about the distinction between your personal brand and the Growth Machine brand?
NAT
Growth Machine grew entirely out of my personal brand. I had a few marketing articles, in particular the one on the Wiki Strategy that people really liked, and so they started asking me to help them with their site’s content and SEO. That soon led to hiring other people to help me implement the processes, and now a year later it’s really its own thing, separate from my personal brand.
But at the same time, I think my content still helps people find the business. There’s no way we could have grown so quickly if I didn’t already have an audience of people interested in my marketing advice. And as more people find me through my content, more people make it to the Growth Machine site.
The other way, and I think it’s kind of silly but it probably helps, is that I brag about our results a lot on twitter. I’ll post screenshots of traffic results (with the client names removed) showing what we’re doing for our clients, and I think that builds trust since they would be extremely hard to fake. It takes no work for me to take a photo of a spreadsheet or Google Analytics dashboard, but it shows that we actually know what we’re doing.
DAVID
One of my favorite writers, Venkatesh Rao says that readers must discover his website Ribbonfarm at least twice in two different ways before turning into regular readers. SEO is great because when it’s executed properly, it drives a ton of web views. However, readers may not remember the website. How do you make sure that readers connect and remember you when they visit the website?
NAT
Honestly, for SEO, that’s not a huge concern. You’re usually using SEO to get someone to buy something, or convert to an email subscriber, not necessarily to turn them into “regular readers.” If you look at the Cup & Leaf blog, for example, no one would read it from one article to the next, because that’s not the goal. The goal is to rank for everything related to tea, have people find those articles, then buy our tea. It’s a very different strategy from building a naked brand.
That said, there are ways you can blend the two. I worked with the Jump Rope Dudes on their SEO and content strategy, but they’re primarily YouTubers. They create great videos on jumping rope and getting in shape, and some of them are targeted at ranking for specific keywords on YouTube like “are rest days necessary” and “beginner jump rope.” They’re a Naked Brand with a very personal channel, but they also take advantage of SEO as they can.
DAVID
Your website receives almost 400,000 views per month. You’re also a voracious blogger and publish a podcast once a week. What have been the keys to your success as a Naked Brand? What’s helped you build such a large audience?
NAT
I think it’s just been to focus on whatever I’m interested in, and not worry too much about doing what people want, or trying to be some sort of Internet personality. I use SEO to amplify my content, but I’ll only write something if I’m interested in it.
The podcast just came from me and Neil reading a lot and wanting an excuse to hang out and talk about books. And then my book notes rank for a ton of keywords related to the different books, and get around 45,000 visitors a month, which brings more people to the blog and podcast. Some people just want to read my marketing articles, or psychology articles, or sex articles, and that’s fine. I don’t need every reader to like every topic I want to cover.
The biggest element is probably that I don’t try to emulate what other people are doing in their brands. You see a ton of bloggers trying to be like Tim Ferriss, and it comes off lazy and repetitive. We don’t need more people living on a beach trying to be Tony Robbins talking about how you can “take control of your life.” Most of those people are trying to copy someone else’s formula, but that never really works. Or if it does, it’s not really your brand since you just copied someone else’s.
DAVID
Most Naked Brands use video to build an audience and generate trust. You’ve done mostly through writing, which tends to extract emotion from the content. In contrast, video is almost all emotion which is part of the reason why it leads to such strong bonds between creators and their audiences. What strategies do you use to build trust with words on a page?
NAT
I don’t think about it too much. I think the biggest thing is how I argue and cite my sources. I’ll try to always link to research articles and reliable sources, never to questionable blogs or dubious sources. And I’m fairly apolitical, in that I try to stay outside of any political party or tribal ideology, which I think helps me engender more trust from readers by trying to look at things more impartially.
DAVID
Consistent content is like oxygen for Naked Brands. By publishing consistently, they stay fresh in consumers’ minds and develop relationships with their audiences. What strategies do you use to maintain a regular publishing schedule?
NAT
None! I just write when I feel like it, and that turns into one post every two or three weeks. I think I’m only able to do that, though, because I’m genuinely interested in what I’m writing about. Nassim Taleb has this great line in one of his books that says something like “writers who struggle to write should stop writing,” I like that idea. If writing is a huge slog, it’s not fun, and it won’t read as good, so I don’t try to force it. I use my excitement about an idea drive what I write about, and that tends to lead to things my audience is interested in as well.
Now, granted, some guidelines help. My newsletter has to go out every Monday. And I want to get up at least one post a month. But beyond that… I’m fairly unstructured. I have dozens of half-finished drafts lying around. I almost never end up writing the post I “plan” to write next. I try not to fight it too much.
I’m a bit better about Made You Think. Neil and I have a fixed release schedule of 1 per week so we have to meet up most weeks to record, which is helpful for staying accountable. It also means I have to keep an aggressive reading schedule, because if I don’t, then I’ll end up spending all day Thursday trying to catch up before our recording on Friday.
“His achievements are on the level not of any Roman emperor but of Rome, and not so much of any generation but of entire civilizations.” — Ryan Holliday
Robert Moses built the greatest city in the world. Parks, highways, tunnels, bridges, and beaches — he built them all. When he began building New York City playgrounds, there were 119. When he stopped, there were 777. An ordinary man with an extraordinary mind, he built the Lincoln Center and the United Nations Headquarters, Jones Beach and the Central Park Zoo, the Triborough Bridge and the Long Island Expressway. He uprooted more than 500,000 people and destroyed the neighborhoods that once housed them. He led thousands and thousands of laborers, and together, they built 13 bridges and 416 miles of parkways, and by the end of his tenure, New York had 45% of all the state parks in America. The dude even invented the parkway.¹
One speaker said that “Robert Moses had outdone his biblical namesake because while the Moses of the Israelites had smote a rock in the desert and brought forth water, Moses of New York had “smote the city’s parks and brought forth not only water but trees, grass, and flowers.”
Robert Moses was never elected to office — not once. And yet, at the peak of his career, in a democracy where power is supposed to come from being elected, The Power Broker basically controlled everything: he controlled all transportation planning, all public housing, all energy policy, and all municipal parks.
The park and highway works of Robert Moses.
As Robert Moses shaped the land and sculpted the terrain of New York City, its residents were stuck in jam-packed, bumper-to-bumper traffic. But Moses never learned to drive. Thus, he never suffered from the nauseating, headache-inducing smell of exhaust in a traffic jam. In fact, it was just the opposite. When it came to his projects, he worked at delirious speeds. He operated with a pedal-to-the-metal attitude and had a fierce, unquenchable drive. He didn’t just defeat opponents. He destroyed them. As he inched up the power pyramid of New York City politics, it seemed like nothing stood in his way. Nobody could stop Moses — not the people, not the mayor. Not even the governor. Feared behind closed doors, but loved by the people, Robert Moses was America’s Master Builder.
How did Moses master the media and accumulate so much power?
By selling simplicity, dominating distribution, and praising the parks.
In his early years, Moses plotted his moonshot career east of Manhattan, in the backwaters of the Long Island State Park Commission, beyond the vortex of municipal decision making, beyond the whispered echo chamber of New York journalists, and beyond the setbacks of Art Deco skyscrapers that kissed the heavens and cut right angles out of the blue Manhattan sky.
Half genius, half dictator, Moses maintained a squeaky-clean image. Financially supported by a trust fund from his Connecticut-based parents, Moses worked many years without pay. Even at age forty-one, Moses earned no income. All the money in his bank account came from his mother. Subsidized by his family’s trust fund, Moses didn’t take a salary, and since he didn’t take a salary, the media didn’t question his intentions. Otherwise discerning journalists intoxicated themselves with Robert Moses Kool-Aid. Delusional, they thought a man who worked for free couldn’t possibly be corrupt.
“A Selfless Servant of the People”
In the eyes of New York’s media moguls, Moses wore a golden nimbus.
The Tribune called him a “selfless servant of the people.” William Odgen, at The New York Times — the newspaper of record — called him “one of the greatest public servants of our time.” Murray Davis of the World Telegram told readers that “for ten years he has worked long hours, without pay, to give New Yorkers inexpensive outdoor pleasures.” He practically walked on water.²
“The image was of the totally unselfish and altruistic public servant who wanted nothing for himself but the chance to serve. A key element in it was his disdain for money — a disdain which he made certain was well publicized and which was symbolized by his refusal to accept a salary for his services… he had made certain that the public knew he was serving as authority chairman ‘without compensation.’
The image was of the fearless independent above politics… The image was of the relentless foe of bureaucrats, the dynamic slasher of red tape… The image of the man who Got Things Done, who produced for the public tangible, visible, dramatic achievements…”
Moses was paid in power, not in money.
The metaphors wrote themselves. Like a king in a castle, his office was surrounded by a river-wide moat which separated Moses from the rest of his New York kingdom. Majestic and imposing, his office, accessible only by bridge, symbolized his independence from the city. On Randall’s Island, Moses reigned supreme. A world within a world. Nobody — not even the highest city officials — could drive to Randall’s Island without paying the Triborough Bridge Authority (directed by Robert Moses) a tribute in coin. Visitors were subject not to city laws, but to Triborough’s, and by extension, Moses’. From the seat of his throne, The Power Broker worked in the shadow of the lucrative, money flinging Triborough Bridge toll plaza. From the comfort of his mahogany desk, Moses glittered with greed and wide-eyed intensity. An emperor of cash and concrete, he sniffed the scent of dollar bills and danced to the syncopated echoes of coins transferring from taxpayers to toll operators. If the Randall’s Island office was the heart of Moses’ empire, the tolls from the bridge that ran across it were its blood. From his office, lined with exquisite, higher-than-the-ceiling maps of New York and Long Island, Moses dreamed up the future of New York with starry-eyed, child-like imagination.
As he painted the canvas of the greatest city in the Western world, Moses built intimate relationships with reporters. These relationships gave him direct control over the mainstream media. By crafting simple narratives, Moses controlled public opinion.³
The Power of Simplicity
The Machiavellian titan spoke with eloquence and vitality. He knew that concise and memorable statements were most effective; he knew that voters rarely did not read extensively, so the spread of his messages depended on his ability to simplify them; he knew that funding went to the pragmatist who had already made plans, not to the dreamer with a foggy vision for tomorrow; he knew the system — inside and out — and exploited its weaknesses.⁴
Time and time again, Moses grossly underestimated the cost of a project in order to get funding. With tactical media manipulation, Moses extended his mind, coordinated his employees, and tilted the balance of public opinion in his favor. With ruthless determination, he built a culture of action and speed. His stainless, sun-bright image concealed his callous and cavalier approach to building:
“The important thing is to get things done.. You can’t make an omelet without breaking eggs.. If the end doesn’t justify the means, what does?”
To the public, Moses was a hero. Buoyed by a crescendo of media support, “Mister Go” manipulated the media and stretched the law.
“When he was building Jones Beach earlier in his career, Moses had confiscated property on Long Island in a way that was almost certainly illegal. It was required by law that he have the funds to pay for any confiscated property immediately, and he did not have it. He was promptly sued by the property owner. He used his lawyers to delay the case from going to court for as long as possible, and started building a parkway going to Jones Beach, a new beachfront park, right away.
By the time the case got to the courts, he had already built the parkway and the beach. Hundreds of thousands of New York residents had driven to the beach with their families for sunny summer afternoons. There were lots of subtle issues at play about under what circumstances the State had the right to seize property and the ruling on the case would set a precedent. From a legal perspective, the case was ‘dark grey’ — probably illegal, but there was some justification if you really stretched the law. And stretch the law the judge did. The judge knew he would get crushed by the newspapers and voters if he ordered a section of the parkway to the beach be turned back over to the original owners. The beach would be inaccessible for years while the highway was being re-routed.
The headline “Judge Rules You Can’t Go to the Beach with Your Kids Anymore” is a career ender and both Moses and the judge knew it.
At the margins, public opinion wins. And he who controls distribution controls public opinion.”
Politics and communication are linked at the hip. They’re nearly synonymous. The essence of politics is applying communication in service of power and personal gain. Only by understanding the relative access to and control over information, can we understand the ebbs and flows of power, politics, and even, the human condition.
In the land of freedom and democracy, Moses’ authoritarian power didn’t just go unquestioned. It was praised. And that praise landed in newspapers and played on television screens with sunrise-sunset consistency. By controlling the leads, Moses controlled New York.
Dominating Distribution: How Moses Shaped Public Opinion
Moses worked in the heart of mass media at the peak of the mass media era. An era where wars were fought not for territories, but for words. An era where global culture spread from the sky-high headquarters of New York-based newspapers, magazines, radio and television stations.
In this broadcast era, communication was asymmetric. It flowed from one to author to audience, press to the people, one to many. Publishing access was restricted. Mass media real estate was reserved for a select few, and that select few had outsized influence. Once you had the press, you had the people. Knowing this, Moses turned connections into control and publicity into power. His infrastructure projects progressed in speedy, coordinated fashion. Delays were kept to a minimum. Sometimes, when he really needed to win a battle, Moses resorted to blackmail. In controversial 50–50 battles, Moses went to the press directly, and where he did, he shaped both the playing field and the rules of the debate:
“He went to the press with his usual blend of demagoguery and deception: breaking the story himself to get his side of it before the public first; oversimplifying the basic issue to one of public first private interest; identifying the “private interest” with a similar sinister forces of “influence” and “privilege”; concealing any facts that might damage his own image, framing the situation of public versus private, Moses versus his opponent, good versus evil.”
By reshaping public opinion — dominating distribution, controlling the narrative, and manipulating mass consciousness in undemocratic fashion — Moses reshaped reality.
Public opinion moved steel and concrete. It shaped hearts and minds, and Moses knew it. In 1927, the press focused on Charles Lindberg, the first person to fly across the transatlantic solo. As Lindberg defied the laws of physics and soared across the skies, Moses accumulated power behind the scenes. That year, in a prescient analysis of the capitol scene in Albany, one New York Tribune headline read: “Moses Second in Power to the Governor.”
If 1927 was Lindberg’s year, 1928 belonged to Moses. With grand dreams and the power to turn them into reality, Moses graced the front of New York City newspapers. The Master Builder even rose above Albert Einstein, who, in 1928, rocked the world of physics when he discovered his theory of relativity. And yet, New York’s thirteen daily newspapers preferred Moses’ physical creations to Einstein’s intellectual discoveries:
“New York’s reporters strove for new adjectives to describe the park builder, one writer concentrating on his physical attributes (“tall, dark, muscular and zealous”), another on the mental (“a powerful and nervous mind”), a third on the moral (“fearless,” “courageous” ) to describe [Robert Moses].”
Editorial writers chimed in. “His labors have been unwearied and successful,” said the Times, “his energy and persistence . . . great.” “He has been a faithful, earnest and efficient incumbent,” said the World. “He has done excellent work.” Even the Herald Tribune was beginning to look on his works and find them good.
And the praise, on front pages and editorial pages alike, continued day after day. If readers were reminded once during 1928 that Moses was serving the state without pay, they were reminded a hundred times.”
Reporters fought for interviews with Moses. In return for the favor, journalists portrayed Moses as a selfless public servant — a man who cared less about politics and more about getting results, less about his salary and more about cutting government costs. Words leaped out of Moses’ mouth and landed directly in print without revision. The media relished his big face, big smile, and big voice and gave readers an impression of grandeur, strength, and power.
His power didn’t just come from the people. It came from the system itself — the laws, the media, and the politicians who governed The Empire State. While citizens applauded Moses, elected officials depended on him. Merciless in his pursuit of power, Moses’ achievements were visible to anybody and everybody. Concrete in form and figure, his bridges, highways, and tunnels allowed elected officials to prove that they had indeed done something for their constituents. When Moses built parks, he won voters’ appreciation, and when he won voters’ appreciation, elected officials kept their power. In the words of one government representative: “Moses was a devil in May, but an angel in November.”
The Early Years
Before Moses rose the ranks of political power, he slithered through the backwaters of law and regulation, learned what nobody else wanted to learn, and drafted bills that nobody else wanted to draft. In a stroke of political genius, “the best bill drafter in Albany” got things done by burying costs behind a facade of inspiring messages. He tricked people. He knew the dirty secrets of politics and did everything in his power to pass bills, bury expenses, and plant costs on future generations.
Moses brought both sizzle and steak. Elected officials came for Moses’ media influence and stayed for the breadth and depth of his knowledge. Nobody knew that vast administrative machine better than Robert Moses. The most fundamental elements of any machine is its architecture, and when it came to laws and regulation for the state of New York, Moses was the chief architect. Years before he rose to power, back when he worked for Governor Al Smith, Moses drafted the state laws himself, from the executive budget system to the constitutional amendments. The law of the land was boundless and Moses seemed to know it all:
“To a considerable extent, the machinery was his machinery; He knew the precedents that made each point in them legal — and the precedents that might call their legality into question. He knew the reason behind every refinement, every clarification — and every obscuration — in the laws’ final versions. When discussing a point of law with some young state agency counsel, Moses liked to let the lawyer painstakingly explain the legal ramifications involved and then say dryly: “I know. I wrote the law.” This store of knowledge, coupled with an intelligence capable of drawing upon it with computer-like rapidity, constituted a political weapon which no Governor could afford to let rust in his arsenal.”
Moses had all the answers:
“It was easier to ask Moses than to try to find out the answer themselves. Because Moses always knew. “He thought fast and he answered quickly”… “He seemed to know the makeup of every department in the state and what its powers were and exactly which sections of law it got those powers from. And he almost seemed to know it all by heart.”
Moses made the machine, fed the machine, steered the machine and naturally, the machine responded to his wishes:
“Power and accomplishment meant Getting Things Done — and Getting Things Done in New York meant playing ball, paying the price, the money price. He played — and he paid. He gave the machine — the greedy, voracious, machine — everything it wanted…
The structure might appear flimsy but it was shored up with buttresses of the strongest material available in the world of politics: public opinion. A Governor — even a Governor who hated the man who dwelt within that structure — would pull it down at his own peril.
Moses understood this. Asked forty years later why Roosevelt did not oust him from his park posts, he would laugh and say, ‘He couldn’t afford to. The public wouldn’t have stood for it. And even if he tried to, it would have been very difficult. See, the law didn’t permit it, except on charges. It was set up that way, see.”
Propped up by the media, and shielded by a facade of selflessness, “The Master Builder,” in a land ruled by public opinion, wore a shield of protection so strong that he could battle and beat just about everybody. When Moses said jump, the others asked: “How high?” In the office, employees, subservient to the lofty demands of their chief, feared him like field mice. Others showered him with praise and elevated him onto a pulpit of transcendent worship. Sometimes, it seemed like even the wind and the waves obeyed him. Nobody, not the media, not the mayor, and not even state Governor Teddy Roosevelt — the New York’s elected leader, who deplored, despised and scorned the ruthless builder — could stop Moses.
Moses was all-knowing and all-powerful:
“For a twenty-year period that did not end until 1968, Moses was given by the State Department of Public Works a secret veto power over the awarding of all state contracts for public works in the New York metropolitan area. No engineer who had ever forcefully and openly disagreed with a Moses opinion ever received even one of the thousands of contracts involved…”
As Moses gained influence, he gained power:
“Not only does a Governor not interfere with an official like Robert Moses; he heaps on him more and more responsibilities. No matter what the job was, it seemed, if it was difficult Roosevelt turned to the same man. During 1930, 1931, 1932, Moses handled more than a dozen special assignments for Roosevelt and produced results on every one. And if increasing Moses’ responsibilities meant increasing his power — giving him more money to work with, more engineers, architects, draftsmen and police to work with — well, the Governor simply had no choice but to increase that power…
There were now seven separate governmental agencies concerned with parks and major roads in the New York metropolitan area. They were the Long Island State Park Commission, the New York State Council of Parks, the Jones Beach State Park Authority, the Bethpage State Park Authority, the New York City Park Department, the Triborough Bridge Authority and the Marine Parkway Authority. Robert Moses was in charge of all of them.”
Others played checkers. Moses played chess.
Moses was a strategy mastermind. Like a lengthened shadow, his authorities mirrored his personality, his vision, and his rock-hard toughness. He treated employees like pawns. When he spoke, they listened. When he gave order, they executed them. Moses was in charge and everybody — even the press — knew it. More, in the power move of the century, when the press relied on expert opinion, they turned to the Authority king himself.
Check.
Mate.
Praising the Parks
Moses had a secret: public parks. Propelled by omniscient power over the media narrative, Moses — the original “thought leader” — constructed park after park and shaped the urban landscape in his image.
Parks were a prominent civic issue, and Moses’ park projects were particularly popular with the public. Parks symbolized man’s quest for peace and serenity, and through a process of alchemy, Moses turned them into a source of political power. By building parks, Moses dug a well of influence and scaled the mountain of political power. Everybody loved parks. Knowing that, Moses used the protective glow of park projects to brighten his public image, attract colorful media support and taste the sweet, sweet flavors of authoritarian influence.⁵ The media lauded him. On all public works, journalists gave him the benefit of the doubt, and since they didn’t dig into stories about him, the public was blind to the legal, financial and political manipulations that occurred behind the closed doors of Moses’ Randall’s Island office.
In 1922, New York City’s parks were few and far between. There wasn’t a single state park in New York east of the Hudson River. Where there were parks, they were more brown than green — torn up, run down, and bent out of shape. According to a Park Association survey, there was not a single structure of any type, in any part in the city, that was not in need of immediate repair. Parks were havens for drunks and idlers. Others were weed-filled vacant lots. In all of New York, a city with approximately 1,700,000 children under the age of twelve in 1932, there were only 119 parks — one park for every 14,000 children. Only 7.28 percent of New York City had been set aside for the recreation of its citizens, the smallest percentage of any of the other largest ten cities in the world or in America.
A man of persistent action, he waved his wand in Long Island first. Moved by the Midas touch of Moses, 3,000,000 people visited Long Island State Parks in 1930. By comparison, the total number of visits to all National Parks in the United States that year was 3,400,000.
And it wasn’t just parks. It was bridges, beaches, and highways galore. By 1930, the attendance at Jones Beach was 1,500,000; by 1931, it was 2,700,000, and by 1932, it was 3,200,000. Accessible by car, Moses’ parks were packed to peak capacity. In 1919, less than seven million American families owned an automobile. By 1923, that figure had jumped to twenty-three million. By 1940, New York had more miles of highway than the next five largest American cities — Chicago, Philadelphia, Detroit, Los Angeles, and Cleveland — combined.
Parks and beaches were gateways towards power and influence. By the 1930s, Moses had revamped the recreational scene. And when he did, citizens bubbled with bliss and roared with praise:
“During 1934, Moses was in the New York papers even more than J. Edgar Hoover… The Times editorial on Moses, for example, was only one of 29 praising him in that single newspaper that year. And the Times also carried 346 separate articles on his activities, an average of almost one per day… There were days, in fact, on which there were five separate stories in the Times… the nation’s most respected newspaper read like a Park Department press release…
By July, the eight War Memorial Play-grounds had been finished, by Labor Day, there were fifty-two others, including the Chrystie-Forsyth Street complex, which was really a park but which was dubbed “the finest playground in the United States” — and a city which in its entire history had managed to build 119 playgrounds had seen its stock of that item increaser by 50 percent in a single year. The city cheered. Its thirteen daily newspapers, however divergent their philosophy, united in heaping wreaths of adjectives on his head. The new Park Commissioner was “dynamic” and “brilliant” in the ultra-conservative Sun, “able” and “enterprising” in the then ultra-liberal World-Telegram, “tire-less,” “fearless” and “incorruptible” in the sometimes conservative, some-times liberal Hearst Evening Journal. Headline writers, using topical catch phrases, talked of Moses’ NEW DEAL FOR PARKS and the AMAZING ACCOMPLISHMENTS OF MOSES’ FIRST 100 DAYS. Editorial writers were more poetic. “Robert Moses has made an urban desert bloom,” said an editorial in the World-Telegram. The Herald Tribune, formally recanting the heresies of which it admitted it had been guilty during his Long Island controversy, dubbed him the “Hercules of the Parks.”
The cheers of the press were echoed by the praises of the public:
“While the parks were blossoming with flowers, editorial pages were blossoming with letters from the public praising the man who had planted them. And it was not unusual at park and playground opening ceremonies for children, prodded by their parents, to break into the cheer “Two, four, six, eight who do we appreciate? Mr. Moses! MR. MOSES!! MR. MOSES!!!”
Where others saw a maze, Moses saw a straightaway railroad track: Moses’ execution was like the train; his authoritarian power, the engine; his media mastery, the fuel.
Mastering the Media
For decades, Moses executed public works on the scale of Ancient Rome with almost zero friction. As he molded minds and ascended the machine, The Media Master rose above the tangled web of government bureaucracy.
The media portrayed Moses in an apolitical, altruistic cloak, and thus, so did the public. Even when he engaged in shady, backscratching graft, that cloak protected him:
“ An idea was no good without power behind it, power to make people adopt it, power to reward them when they did, power to crush them when they didn’t…
No one could disprove Moses’ reputation without first opening Triborough’s books, and no one could open Triborough’s books without first disproving Moses’ reputation… The magnet which attracts corrupters… the natural locus of corruption is always where the discretionary power resides. In New York City, in the postwar era, the discretionary power resided principally in Robert Moses.”
Moses molded the machine with furious impatience. Warm with allies, cold with enemies, he operated with a stiff neck, a steel will, and an iron fist. With matchless guile, he turned grand dreams into grand creations. In terms of money, Moses was not corrupt. In terms of power, he was. To use the politicians’ phrase, Moses was “money honest.” And yet, his nostrils twitched to a single, irresistible aroma: the aroma of power.
Moses controlled something better than money — he controlled thought. Propelled by supreme control over the media, Moses was crowned king of Gotham. Part hero, part villain he constructed New York with Sim City speed and dexterity. In a world where power is supposed to come from the ballot box, Moses — who was never elected to office — accumulated more power than any mayor or governor combined, and he held that authoritarian power for 44 years. Broadcasting his views through memos, mass mailings, and press releases, Moses accumulated more money, more influence, and more power than just about anybody to ever step foot on Planet Earth. By dominating distribution, selling simplicity, and praising the parks, The Power Broker mastered the media and built the greatest city in the world.
¹ Inspired by the lessons of a previous post, I’ve also tried to mimic Robert Caro’s writing style. Unless otherwise noted, all the information in this post can be attributed to Robert Caro.
² Desperate to maintain his gleeful image as a public servant, Moses kept the money from his mother’s trust fund all to himself. Robert’s mother entrusted Robert to dole out trust fund money to his brother, Paul. Moses had other plans. Using the same smooth maneuvering that characterized his industrious dedicated, Robert made sure his brother Paul received nothing.
“For almost four years — from October 3, 1935 to August 3, 1939 — Paul Moses had received nothing from the trust fund his mother had left for him… He took away from a brother who was poor while he was well off, who was walking the streets with holes in his shoes and sleeping in a Salvation Army lodging house, who was almost literally starving for want of a few dollars.”
Robert hijacked Paul’s inheritance. A monstrous injustice — directed at his brother. Robert didn’t care. In charge of apartment developments for hundreds of thousands of New York residents — more than 500,000 in total — Robert could have easily called up a favor for his ailing brother. But instead of picking him up, he spit on him. Like a piece of trash on filthy Fifth Avenue, Robert ignored — no, stepped on — Paul.
So little did he care for his brother or sister that in one 339-page book on the life of Robert Moses doesn’t even mention that he had a brother and a sister.
Ego first. Family second. Moved by a big dreams and a lust for power, Robert had an image to protect:
“In the city in which his brother lived in luxury, Paul Moses lived out the last ten years of his life in a terrible poverty… In his late seventies, he would be stricken by a serious illness. Thereafter climbing [the steep, wooden stairs of his top floor loft] was very hard indeed. Any apartment in an elevator building would have been a blessing to him. His brother was creating tens of thousands of such apartments: low-income, middle-income. He gave out such apartments as favors to innumerable persons. Any politician with a relative who wanted one had only to ask; Robert Moses would provide.”
And yet, Moses turned a blind eye to his desperate — dying — brother. One day, Paul couldn’t struggle up the stairs anymore. At the age of eighty, he died.
³ The media took Moses down later in his career.
⁴ Moses also used hospitality as a political weapon.
⁵ Next time you fly into La Guardia and hop in a taxi on your way to Manhattan, your driver will probably drive you along Grand Central Parkway (Interstate 278), you’ll cross the East River at 125th street on the Robert Moses constructed Triborough Bridge. On your way, you’ll cross the Robert F. Kennedy Bridge east of 100th street, across the East River in Queens.
As Robert Caro wrote:
“The Manhattan terminus should have been placed at 100th street. The bulk of the bridge traffic — 85 percent by one estimate — would be coming from, and going to, destinations south of 100th street. Placing the Manhattan terminus at 125th street condemned most motorists traveling between the borough and Queens to drive twenty-five unnecessary blocks north and then, once on the bridge, twenty-five totally unnecessary blocks south — to thus add two and a half totally unnecessary miles to their every journey over the bridge.”
At first glance, this layout made no sense. Sending drivers across 100th street was more convenient and logical. In fact, New York officials had planned a 100th street connection between street connection between Queens and Manhattan.
Why doesn’t that bridge connect directly with 96th street in Manhattan? Why do you have to drive all the way up north to 125th street and then drive all the way back south to 96th street?
In 1934, New York officials wanted to build a bridge to connect Queens, the Bronx, Randall’s Island Park and mainland Manhattan. After taking over the project, Moses quickly got schooled in the arts of political power. learned It was a lesson in The Triborough Bridge project needed media support. At the time, William Randolph Hearst, who owned three of New York’s most powerful media outlets, owned a big bunch of Brownstone slum swellings on the corner of 125th street and 2nd avenue, next to the East River. The slums were profitable for years. But now, it was the Great Depression. Poor people couldn’t afford rent. Hearst was losing money. Eager to take the Brownstones off his hands, Hearst convinced the city to condemn his them, buy them, and use the space for the Triborough Bridge project.
Building the Triborough Bridge across 125th street was inefficient. On paper, it made little sense. But politics trumps paper and influence trumps efficiency. Moses — a man who loved efficiency — didn’t dare move the Manhattan terminus.
Then and now, if you want to get things done in New York City, you never, never, never pick a flight with the owner of a major newspaper. Due to Hearst’s influence, thousands of commuters make this detour every day. Eight miles, each way. An extra twenty-five blocks in bumper-to-bumper, honk-honk-honk Manhattan traffic.
Information is like food. You are what you consume. Tell me what you pay attention to, and I’ll tell you who you are.
In the information economy, knowledge is freedom. The most successful people are the best learners, and as a result, they have freedom to choose where they work, who they work with, and what they work on.
Historically, information has been scarce. Access to it has been expensive. But on the internet, the capacity for learning is widely accessible.
However, the best ways to learn online still haven’t been established.
What’s the best way to learn on the internet?
The Medium is the Message
Most people focus too much on the content of what they consume, and not enough about the context where they consume it. They view information mediums as fungible. But different mediums , such as articles, books, videos, and podcasts are better for different stages of the learning process. The content varies regularly, but the mediums of information flow change slowly. Thus, the medium is every bit as important as the content.
Blind to the social and psychic effects of information technology, they’re like fish in water — unaware of the water they swim in. In turn, they under-estimate the differences between ways to consume information. Different mediums emphasize different senses and stimulate certain ways of thinking and feeling.¹
Each medium has strengths and corresponding weaknesses.
Speech-Based Media vs. Text-Based Media
Before we move on, we need to define two terms:
Speech-Based Media: Podcasts and Videos
Text-Based Media: Books and Articles
The Learning Funnel
My process for online learning moves down a funnel from speech-based media to text-based media — from podcasts and videos to books and articles.
As I move down the “Learning Funnel,” I change how I learn. This funnel, with speech-based media at the top and text-based media at the bottom, isn’t a one-way street. Even as I move down the Learning Funnel, I’ll sometimes swim upwards and improve reading comprehension with videos and podcasts.
The Learning Funnel
Speech based media is high-energy. It’s loaded with emotion. The vocabulary is simple, and gives me a easy-to-understand, two-dimensional overview of a subject.
In contrast, text-based media — books and articles — is like going from casual, toes-in-the-water swimming to full-on scuba diving. Reading builds expertise. Text-based ideas are transmitted are low-energy and emotionless. Ideas are transmitted explicitly, which inspires complex thinking and precise communication.
In short, this transition from swimming to scuba diving creates a Learning Funnel. Speech-based media is the top and text-based media at the bottom.
Speech-based mediums stimulate your emotions. Speech-based media is more inspiring than static words on a page.
I use speech-based media — podcasts and videos — to test out the temperature of a new subject.² It’s like dipping your toes in the water at the local swimming pool. With my head above the water, I can maintain optionality. I can shift my attention between ideas and activities. Even though it’s shallow, it’s fun.
Speech is intuitive and low friction. When we speak, we use a much simpler vocabulary than when we write. Just compare bar talk and an academic essay.
The spoken word is lossy. It trades truth for compression and detail for amplification. Through pitch, enunciation, and body language, speakers communicate information in explicit ways.³ Great orators speak in memorable ways and repeat what’s important.⁴
Speech is a dynamic, two-way medium. Speakers and their audiences communicate bi-directionally, in real-time. As they speak, they gauge the facial expressions of their listeners and interact in other implicit ways. In times of clarity and understanding, they speed up. In times of confusion and mis-understanding, they slow down.
Speech-based social and visual learning platforms have only taken off in the past decade. Since podcasts and online videos are newly ubiquitous, we under-rate their potential as learning platforms and don’t know how to properly take advantage of them.
Scuba Diving: Text-Based Media
Once I’ve laid the foundation through speech-based content, I move down the Learning Funnel — towards text-based media.⁵
Books and articles excel where podcasts and videos don’t. Like scuba diving, text-based media offers a in-depth, three-dimensional perspective. If an idea catches my interest, I dive into the water and explore it deeply. Like scuba diving, intense learning experiences demand focus. They’re surprising and unpredictable.
Writing activates precise, rational thought patterns, which real-time, on-the-fly speaking and listening cannot produce. Similar to how scuba divers, explore the deep depths of the ocean, reading is the best way to understand the nooks and crannies of an idea. Like scuba divers, readers are immersed in their environment, fully focused, and blind to what’s happening elsewhere.
Reading forces logic. In relative terms, reading is an emotionless experience.⁶ It inspires critical, independent thinking. Attention wavers and wanders, and when it does, we pause and reflect.
Unlike videos and podcasts, books are articles don’t have an auto-play feature.⁷ You can’t just press play and do something else while the information flows.
Reading, though, makes total understanding possible. Readers can easily jump around. They can skip sections, re-read confusing parts, or pause to reflect on an idea.⁸
Like swimming and scuba diving, speech based media and text based media are similar activities, but impact your senses in different ways. Not all information is created equal. Each activity has tradeoffs.
By improving your process for information consumption — knowing when to swim and when to scuba dive — you can make online learning more efficient and enjoyable.⁹
Footnotes
¹ Switching between mediums has also improved my learning stamina. I like to switch what I’m working on every 2–3 hours. By switching between podcasts, videos, and books, I can keep learning and stay fresh. It’s a perfect balance. Since I’m guided by mood and energy, I’m consistent in my consumption, and I remain consistent because my learning feels loose, free and unstructured.
² I subscribed to YouTube Red, which makes it easy to watch and listen to videos and podcasts.
³ Heavy readers tend to under-estimate how much information is embedded in speech and body language.
⁴ These redundancies aren’t as inefficient as they seem. Knowledge that’s not repeated disappears. Repeating a message reinforces it. For more, see my Orality and Literacybook review.
⁵ There are exceptions. When I read The Power Broker, a 1,200 page — 700,000 word — study of New York politics, I knew nothing about urban governance. To improve my understanding and get psyched about the book, I watched interviews with author Robert Caro and a documentary about Robert Moses, the book’s protagonist.
⁶ Exclamation points, italics, and bolded words are minor exceptions. And due to their back-and-forth nature, in-person conversations with experts are an excellent way to stir up the emotion, clarify misunderstandings and arrive at new insights.
⁷ Audible is a noticeable exception, but this is generally true.
⁸ Reading usually takes first priority. An intelligent reader said it best in an email:
“I only really listen when I’m doing some other activity that prohibits reading. I never listen when I could be reading, but that’s just a personal preference. So I naturally look at audio as lower opportunity cost time b/c I’m already doing something else productive (working out, subway, walking, cooking, etc.).”
I also default towards reading. I’ve built this bias into my learning system. I’m a dilettante with speech-based media. I use speech-based to explore new realms of thought. I’ll consume anything and everything. Once I’m sedentary, I’m much more focused. I turn towards text-based media and look towards mastery. My text-based inputs converge towards topics I’m familiar with, and projects I’m working on. In reading, I crave detail.
⁹ One thing I’ll add: I rarely consume news. I look for non-expiring, long-term knowledge instead.
This book project requires an extensive research process. I plan to conduct many interviews with writers, influencers, and entrepreneurs. The interviews will all be public and will live right here on my website. We’ll go on this journey together — you and me. Together, we’ll cross industries, speak with experts around the world, and explore the past, present, and future of Naked Brands.
If you have ideas or feedback, please send them my way. You can find my contact information here. I look forward to hearing from you.
His dream was to be an entrepreneur since he was a kid, but his parents forced him to pursue his education. He wasn’t going to let his dream die so he started multiple businesses while in college.
He even bought his first real estate investment property when he was just 19! He is now the host of the Minority Mindset YouTube Channel, one of the largest channels on entrepreneurship and financial literacy with over 15,800,000 views and 370,000 subscribers.
David: What other YouTube entrepreneurs inspire you?
Jaspreet:Casey Neistat, a YouTuber who has created a whole world of influence around his channel and himself just living his life. It just shows the opportunity now that the internet has brought to people because you can do anything you want and be whatever you want and live your life the way you want. If you’re willing to put in the work. Nothing happens overnight, but anything is possible.
David: One of my favorite ideas that the best creators are short-term, catchy and long-term sticky. You find them and they catch your attention and get you really interested, but then over the long term, education is what gets you to stick around. How do you manage the tradeoff between entertainment and education? How do you get people excited when they first find your content but to also get them to stick around over time?
Jaspreet: It’s a balance, because in the beginning a lot of our videos were just straight education where it was like a lecture, like going to school and I’m a teacher and I’m just talking and I wasn’t being me. Like I was just there. Just giving you a lecture on information, but was getting bored of it. I’m sure the audience was like, okay, this is cool, but you don’t want to just stick to it and watch lectures all day. I’m a sarcastic person and I’m not too funny, but I’ve tried to throw in with jokes here and there. I’m not a very serious person and I’m looking at myself on Youtube, like why am I looking so serious?
This is not me. And so I think it’s partially just being you. Everybody has their own unique style. I know some people throw in a lot more education, heavy content, and some people are more entertainment heavy. It really just depends on what you want to do and there’s an audience for everybody. And eventually if you keep doing it, that audience will gravitate towards you and they’ll want to watch your type of content when it comes.
David: You said that there’s an audience for everybody, but there’s also an element of always improving, right? Trying to get more people trying to increase the relationships that you do have. How do you think about improving on Youtube? Where do you get your inspiration from and what sorts of things have you done to become a better Youtuber?
Jaspreet: The first thing that I did was I took an acting class. I was a part time law student just for fun and then I did night school for acting or like once or twice a week. And that was really interesting because I’d never done anything like that before. So just learning how to express yourself and talk in front of a camera, it just gives you the extra practice. And so for me that was one thing to help me out.
David: As you were going through acting school and think back, if you could go back to one or two things specifically, what were they?
Jaspreet: One thing that was really interesting was the first day I went there, I had no idea what I was doing. So you introduce yourself and then say I’m here for the job attribute. So I had my own ways of doing it. I was just like, oh yeah, I got the job interview or just something kind of plain. But you could see some people that would be really creative and do different things. I never thought of breathing like that. I never thought about screaming or just whatever they did, you’re just kind of see different people’s flavors in different situations of the same thing. So just understanding how to present the same information in different ways. It was really cool and I never thought about it like that until I thought.
David: If you watch movies to act or never really looked at the camera, you’ll get a show like The Office where they break the 4th Wall, and shoot with a shaky camera and the interviews really feel like the white is talking to if you were. But on Youtube, you’re getting these very close relationships with youtubers and it’s sort of crazy, right? Because if we spend all this time with youtube, we all spend more close, really intimate time with these youtubers than we do with our friends, with our family and I’m just wondering how you think about the relationships that you have with your audience and how you think about camera shots like that?
Jaspreet: Youtube and digital video is going to take over TV in because it’s so interactive. When I’m on Youtube I can actually interact with a person who’s watching. You can say, what do you think about this? Let me know your thoughts in the comments and all of a sudden you’re interacting with me as you’re watching, like I might even go and respond to your comment. It creates a whole new dimension that, like you were saying, that kind of the fourth dimension, because we’re breaking that wall between the screen and the viewer. I will try to find ways to interact with you to make you feel like you’re a part of us because that’s what really differentiates the Internet and kind of digital media in the sense of youtube and those type of things as opposed to tv because TV, you feel like you’re so far away from this celebrity that you’ve never heard of.
You might be interacting with them as so many other ways that you won’t with TV personalities.
Jaspreet SIngh with the 100,000 Subscriber YouTube Plaque
David: The relationships that we have with brands have also changed the way that we consume their content on social media. Our expectations of what is the brand are changing just as much as content itself is changing. And from your experience, now that you’ve thought about this from a youtube perspective, how is your interaction with brands changing?
Jaspreet: Brands have to give back in the day if a brand a business or selling a product, their job was just to sell you a product, right? But now I mean there’s so much more to selling a product and just having a product to sell. People want some other value. Why am I going to go to your brand’s page? What am I going to get from you besides just your product? Like for example, I feel like a shopify, they have a very cool tool, but they also have a very popular blog on ecommerce, how to sell products. And so they’re driving traffic in because of people who want to learn how to sell on the Internet at that right there, they have their backend product, which is, well, if you want us to do it, uses our platform.
So they’re giving people more than just a product. They’re giving people a reason to come to them. It opens up possibilities for people who are willing to think different and do things different. I kind of break out of the norms and the traditional way of doing things. It just opens up a whole new world of possibility.
David: Yes! I like to say that people are becoming brands and brands are becoming more like people. The strict bifurcation between people and brands has disappeared. People and brands operate on a spectrum now. And it’s interesting because it’s a byproduct of the way that media is changing, which I think that almost all of this goes back to. What do you see in terms of what is the best Youtubers have in common?
Jaspreet: They’re fun to watch. I mean, it really comes down to that, when you go onto youtube, you don’t want to sit there and be bored. You want to sit there and have fun and relate to the person. Even if I’m learning something, I wanted it to be an enjoyable experience because now I mean it goes back to supply and demand. Anybody can start a youtube channel. And so if somebody else can get the same information in a better, more entertaining, more interactive, more fun way, I’m going to watch them.
David: The internet has destroyed so many barriers and unlocked floodgates of opportunity. What inspired you to get into the YouTube sphere?
Jaspreet: I never planned on going on youtube or making videos or being a so called insolence or, or whatever. I’ll always been an entrepreneur and I was working, I want in my previous business ideas and we, when I was getting ready to launch it, I hired a marketing company to help you with the marketing of it during Gar crowdfunding phase. And it turns out this marketing company was a scam. Before I gave them the money, I was a little skeptical. So I was like, what’s my guarantee? What if I don’t make it work? They were like, oh, don’t worry, we’ll give you a 100 percent money back guarantee. If you have any issues, call us. We’ll get you your money back for the 24 hours.
Don’t get caught in the same scams and traps that I did because growing up I was never taught anything about entrepreneurship, business money, anything like that. My parents always told me that was bad (entrepreneurship and business), that’s evil, stay away from it. Like my family comes from a small state in India called Punjab. So they grew up with very traditional values. They always told me, be a doctor, be good in school, blah, blah, blah, all that stuff. And I did school that did all of that and I was always doing my entrepreneurship stuff on stuff on the side because data approve of what I did.
I never really had any guidance. I never had a mentor. I never really had anyone kind of telling me what’s right, what’s wrong or given me some sort of teachings or anything. So after I got scammed I was like, well let me do something about it. So I started putting out content on how to launch a business without getting screwed over. I had no idea what I was doing. And then from there I just started doing it, just started talking and somehow people caught on and they loved it and we grew from there. Now we’re at like 350,000 subscribers, tens of millions of views. It’s like, how did this happen? So it’s been a blessing, with a really unique beginning.
David: You bought your first property during the financial crisis when you were 19 years old, if you could just walk through that story. It’s just unbelievable.
Jaspreet: I never even knew what entrepreneurship was. When I came to college, I wasn’t much of a partier. I don’t drink. So I came to college and everybody was partying and I was like, well I need something to do outside Friday night. I do have some experience in this event planning business. So how about instead of going to the parties, start hosting them.
I started out there and that kind of developed the whole majority mindset versus minority mindset thinking with a majority people like going to parties. So then I started doing something different. The hosting them started doing really well. We’re hosting concerts and shows and we were doing a lot of different things and my parents, they wanted me to be a doctor, so after my second year in college I was studying for the MK, which is the medical college admission test to get you into medical school. And I was going crazy studying for it. I was just the worst. In the library all day. And then during my free time I was reading financial news.
Like finance.yahoo.com. See what’s going on and everything. They were talking about real estate, there was a lot of “rock bottom, get out now”. Real estate is horrible. The economy is crashing. And every business book that I read, they kept talking about how successful people, wealthy people invest in real estate. I had no idea what that meant, but I was like, let me figure it out what this is. So I talked to my dad, I’m thinking about investing in real estate because all these books are talking about it and the new says that real estate is really cheap and my dad’s like, no, you are not going to invest in real estate. That’s just like gambling. So then I was like, well I don’t know if I’m going to listen to my dad here.
So then I called up an agent, started looking at properties kind of long weekends and I found a cheap condo again. I had no idea what I was doing and I ended up putting an offer. We got accepted.
David: Talk more about the philosophy behind the Minority Mindset.
Jaspreet: It has nothing to do with the way you look, your ethnicity, your skin color. It’s a mindset. It’s the mindset of thinking different than the majority of people. If you follow what the majority of people do blindly, you are pretty much guaranteed to fail. The majority of people are broke. The majority of people hate their jobs. The majority people are miserable and the majority of people are physically out of shape. If you keep doing what everybody else does, you’re gonna end up like the majority of people and so it’s the mindset of thinking different and breaking away from this traditional path and doing something and creating something of your own instead of just being a follower and kind of just a victim of the system because right now school and just the traditional system is not working for the majority of people and so it’s a mindset of breaking away and thinking different and kind of creating your own plan.
If you are not growing in a way that you want to grow, whether it’s financially, whether it’s physically, whether it’s mentally, or whether it’s spiritually; get away from it. If people are not pushing you to be better, get away from them. Getting out of your comfort zone to do something that you’ve never done before, that’s the only way you’re gonna be able to grow and get to somewhere where you want to be.
There are so many people doing it. How am I supposed to get seen? Easy. Be Different. How well, that’s what you have to figure out, that’s the tough part. And so, that’s really what it is. If you go in and you start to become an influencer on instagram, we try to build an audience on instagram or youtube or whatever and he just do what everybody else does. You’re going to just blend in with everybody else if you’re going to scroll past you because people have been doing it for a lot longer than you and they’ve already built their niche and their space there. So if you want to get seen and you want to build traffic, you have to be different. Give people a reason to follow you or, or look at your content instead of somebody else’s.
It’s easy to say be different, right? But I think that that sort of begins with our thoughts, our actions, and with the people that we surround ourselves with.
“Everything I’ve been writing is bullshit.” — Robert Caro
Robert Caro’s is the world’s greatest biographer. Like a treasure chest, his works are a window into a whole new world.
The Power Broker, written by Robert Carois a first-rate examination of the political forces that shaped New York City. Heavier than the weights I use at the gym, Caro’s books take six months to read and a decade to write. His books are a marathon — a bigger time investment than most college courses.
And yet, David Halberstam called The Power Broker “the greatest book ever written about a city.” Barack Obama, who read The Power Broker when he was 22, hailed it as the most influential book he’s ever read.
Never, never, never in a million years did I think I would read a 1,200 page — 700,000-word — window into the politics of New York. But first-rate writing is seductive, no matter the topic.
In a world of falling attention spans, how does Caro keep the attention of his readers?
Scuba Diving with Caro
If Twitter is like dipping your toes in the water, reading Robert Caro is like full-on scuba diving. You can’t half-ass Caro. His books are too long. Too dense. You’re either all-in or all-out, and without a daily ritual, you won’t finish the book.
In The Power Broker, Caro exposes how raw, naked political power works in cities. It’s non-fiction that reads like fiction.
Caro’s famous for winding, snake-like tangents that veer from the main plot line. As you march through sentences and meander through paragraphs, you can see the characters, feel the tension, and hear the debates that shaped New York City. You feel like a fly on the wall. Caro includes detail after detail — down to the year and brand of Moses’ Egyptian gold tie clip — that any editor with their head on straight would have crossed out with a big bright red pen.
The Power Broker was a surprise success. Here’s Caro:
“For seven years, I heard people say — I heard my first publisher say — no one is going to read a book on Robert Moses. It will be a very small printing. And I believed that. But as I came to write the book, I thought, It matters that people read this. Here was a guy who was never elected to anything, and he had more power than any mayor, more than any governor, more than any mayor or governor combined, and he kept this power for forty-four years, and with it he shaped so much of our lives.”
As I poured and poured through The Power Broker, I discovered how Caro writes world-class biographies.
See the Scene
Next time you’re in New York, look up and around. You’ll see Robert Moses’ canvas. The bridges, tunnels, and highways are his paintings. Nuts, bolts, and concrete are his paintbrush. Psychedelic in their intensity, Caro’s descriptions will turn your hard eyes starry.
Caro is stiff under the public eye. In interviews, where he reveals the secrets of biography, Caro offers writing advice in a taut, careful manner:
“You have to ask yourself, Are you making the reader see the scene? And that means, Can you see the scene? You look at so many books, and it seems like all the writer cares about is getting the facts in. But the facts alone aren’t enough.”
Clad in suit and tie, Caro writes in solitude. His writing practice resists the pull of technology and the allure of efficiency. Caro writes with pen and paper. He cuts and pastes — not with savvy keyboard shortcuts — but with scissors and tape. Only recently did he purchase his first computer and he still doesn’t have an email address. As the kids say, he’s “old school.” Early drafts are handwritten on legal pads. For later drafts, Caro switches to a typewriter.
Caro begins each book with a written statement of its narrative arc. Then, he opens his matte black, loose-leaf notebook and writes a detailed outline. As Caro’s ballpoint pen meets his white narrow-lined legal pad, his scenes spring to life:
“If you let the reader see the place — if you do it well enough and have shown the character of your protagonist well enough, so that the reader can see the scene and be involved in the scene — then the reader can see things, sense things, understand things about your protagonist that the writer doesn’t have to tell him, that the reader can grasp for himself. When you’re in a place, it evokes emotions in you.”
Caro defies the limits of the written word. Marshall McLuhan once described the written word as abstract and emotionless. But in The Power Broker, the words are alive. Dancing across the page, words twinkle like stars on a cool winter evening.
As you read The Power Broker, you can see the geography of New York in Gingerbread detail:
“[Moses] changed the course of rivers, filling in the beds of the Harlem and the Bronx and cutting new channels for them, shoving to one side the mighty St. Lawrence, making new curves in the swift Niagara. He filled in the city’s frayed edges, transforming into solid earth Great Kills on Stated Island, the Flushing Meadows in Queens, a dozen other vast marshes. Nature gave the region one shoreline; he gave it another, closing inlets in the barrier beaches, creating new insets, reshaping miles of beach dunes. For mile after mile, the earth and rock that constitute the shoreline of Brooklyn and Queens, and of Manhattan’s Hudson shore, are his, the cement and steel that hold them in place are his, the grass and shrubs and trees that adorn them are his — as are the concrete and steel of the marinas, the shoreline overlooks, the parking fields, the bicycle paths, the runways and airport terminals, and, of course, the shoreline parkways. Not nature, but he put them there…. Robert Moses believed his works would make his name immortal and he may have well been right.”
The stage has been set. The King of Gotham has been crowned. Here’s New York — grand, sprawling, and magnificent — and here’s Robert Moses, ThePower Broker’s all powerful, bigger-than-life protagonist.
America’s greatest road-builder began his career at a time when not a single American city possessed a budget. Nobody — nobody — influenced American cities in the 20th century more than Robert Moses. Through a process of alchemy, Moses translated dreams into concrete, asphalt, and steel. He was directly in charge of $26 billion worth of public works, a figure which no other urban public official comes close. Moses shaped American expressways more than any single individual. Most public officials made recommendations; Mr. Moses made laws; most public officials outlined their dreams; Mr. Moses bragged about his accomplishments. Simply put: Mr. Moses “Got Things Done.”
Robert Moses
Caro describes the voluminous figure as such:
“Mr. Moses started pacing, almost like a caged tiger…. When he heard a report of some delay or obstacle, the big powerful face would turn pale, almost white, and a wave of purple, rising up the thick neck, would sweep across it.”
“His physical presence and vitality as he stood, head thrown back, teeth gleaming in his dark face, handsome, charming, physically overpowering his listeners… made him, as always, the focal point of the room… with an expression on his face that could only be described as enigmatic.”
Here, you can feel Moses’ iron-will. You can smell his sharp determination. You can see his eyes dilate in a gaze of fury. Rather than describing Moses as stubborn, aggressive and arrogant, Caro uses phrases like “caged tiger,” “thick neck,” and “wave of purple.” We see the scene with 20/20 vision.
Caro’s description of George Gleason, a newspaper writer, radiates with similar intensity:
“Big, brawny and boisterous, with a cooked Irish grin and a nose that must have been broken at least once in his thirty-two years, he looked the part — complete to the collar of his trench coat, which was invariably turned up. And he acted it. Hard drinking, he talked loudly in barrooms about the big stories he was working on, the big men he was going to unmask…”
Clear as day. In true Caro fashion, each description is vivid enough to paint an image in the reader’s mind, yet abstract enough for the reader to experience the scene in their own, individual way. Readers see Moses in vivid detail without having to slog through mundane facts or endless, rambling lectures.
Interviews
As he composed The Power Broker, Robert Caro conducted 522 interviews. The search for detail begins in the interview process:
“So you keep saying, What would I see? Sometimes these people get angry because I’m asking the same question over and over again. If you just keep doing it, it’s amazing what comes out of people.”
By asking the same question over and over again, each time from a slightly different angle, Caro cuts through the camouflage and adds texture to the scene. One layer at a time, he unlocks forgotten memories.
Sometimes, when the quotes are particularly jarring, Caro inserts them directly into the text. During one interview with Caro, a victim of eminent domain described his dilapidated home like this:
“My son Stephen — he’s six — is in the hospital. A rat bit him in the eyes. I tried to fix the rat holes here, but the rat cut right through. I complained but no one did anything to fix them… I have no water, hot or cold… the bathroom ceiling is falling down… rats all over the building… sewers backing up… dumbwaiter packed with garbage… cellar flooded.”
From the gross to the miraculous, Caro writes with visual intensity. Readers can see, hear, and feel how power effects the powerless. Readers transcend the ordinary constraints of language and letters on a page, and experience these emotions first-hand. When I read this paragraph, I feel my nose wrinkle, my nostrils compress, and a recurrent pang of disgust trickle down my tense forearms. These weren’t ordinary rats. No. These rats were big enough to wear saddles. And after writing about these four-legged monsters, I’ll close my eyes tonight with a little extra suspense.
Woof.
Most biographers give you fact after fact. Caro gives you image after image.¹ Most non-fiction is a stoic, firehose of information. But Caro eschews the conventions of non-fiction. Instead, he borrows the lessons of Tolstoy, Fitzgerald and Vonnegut.
Facts alone aren’t enough. They’re too black-and-white. Readers yearn for images and anecdotes that make the information pop. For facts to stick in the reader’s mind, they must be enriched by colorful stories.² Aided by subtle visuals and roller coaster narratives, Caro brings his biographies to life.
That’s Robert Caro’s secret: he unlocks the electricity of sight.
That’s why he shines. That’s why he’s a Pulitzer Prize Winner. That’s why Robert Caro is the most celebrated biographer of all-time.
¹ After finishing this blog post, I went straight to Robert Caro’s biography of Lyndon B. Johnson. As Caro describes Hill Country, Texas, he’s wearing the Magic Binoculars:
“Beneath the trees, the whole country was carpeted with wildflowers, in the Spring, bluebonnets, buttercups, the gold-and-burgundy Indian paintbrush in the white-flowered wild plum, in Fall, the goldeneye, in the goldenmane, and in the golden evening primrose. And in the fall the sugar maples and sumac blazed red in the valleys.
Spring gushed out of the hillsides, and streams ran through the hills – springs that form deep, cold holes, streams that raced cool and clear over gravel and sand and white rock, streams lined so thickly with willows and sycamores and tall cypresses that they seemed that they seemed to be running through a shadowy tunnel of dark leaves. The streams had cut the hills into thousand shapes: after crossing 250 miles of flat sameness, these men had suddenly found a landscape that was new at every turn.”
² David McCollough, another famous biographer made a similar observation.
We teach children how to write, but not how to speak. That’s why very few people know how to improve their own speech.
Luckily, I can help you improve your speech.
I learned how to improve mine by accident. As a podcast host, I spend a lot of time listening to my own voice. I listen to critique myself, edit the podcasts or re-listen to old episodes for fun. At first, listening to your own voice is annoying. I’ve experienced that. But after a while, you get used to it.
Improving speech falls into two buckets: (1) what to stop doing, and (2) what to start doing.
Bucket #1: What to Stop Doing
Nassim Taleb has a principle called Via Negativa. The idea is deceptively simple.
Taleb defines Via Negativa like this:
“In life we know what is wrong with more clarity than what is right, and that knowledge grows by subtraction. Also, it is easier to know that something is wrong than to find the fix. Actions that remove are more robust than those that add.”
To improve your speech, start by removing bad habits. Cut the “ums,” the “likes” and the “you knows.” If you need to think, pause. Record yourself having a conversation. Inevitably, you’ll find things you don’t like.
Write down your three biggest speech inhibitors. Then, as you have conversations, don’t say those things.
Move onto the second bucket once you’ve broken your worst speech habits.
Bucket #2: What to Start Doing
The first bucket is simple and straightforward: cut out your worst speech habits.
The second bucket falls into the choose-your-own-adventure category. There are many paths you can take. I’ve focused on (1) writing regularly, (2) studying rhetoric and (3) emulating my favorite speakers.
Here’s how I go about each one:
1. Writing Regularly
I write for at least an hour every day. No exceptions.
The inspiration for a daily writing practice came from Fred Wilson, the founder of Union Square Ventures. He’s published a blog post every day for 14 years.¹
In his words:
“Writing regularly makes it so much easier to speak publicly in unscripted situations… Writing forces you to work out your views and articulate them clearly and concisely… Then when you are asked a question related to those views, you have already worked out the answer.”
Writing takes you to a higher level of consciousness. It demands rigor and enhances perception. It transports you through layers of discovery and into unexplored territories of insight. As you do, you journey beyond the limits of ordinary thought.²
As they venture beyond the mundane, writers wash away the tired residue of conventional thought. They map the unexplored, unarticulated and undiscovered territories of consciousness. As they do, they narrow the gap between the infinite nature of reality and our limited ability to make sense of it.
Thus, through a process of osmosis, improvements in writing lead to improvements in speech
2. Study Rhetoric
Memorable sentences follow ancient rhetorical formulas. Once you start learning about rhetoric, you can use it to improve your writing, and once you bring these tricks into your writing, you’ll start speaking with them.³
For an example of rhetoric, re-read the previous sentence. It’s an example of an anadiplosis, my favorite rhetorical trick.
Anadiplosis is when you take the last word of the previous sentence and use it as the first word of the next. It creates the illusion of logic and inevitable progress. In turn, ideas gain strength, structure, and certainty.
Feel the differences between these two sentences:
Sentence #1: “Fear leads to anger, anger leads to hate, hate leads to suffering.”
Sentence #2: “Fear leads to anger, which leads to hate, which leads to suffering.”
Sentence 1 is stronger and more memorable.
As Malcolm X once said:
“Malcolm X observed that: Once you change your philosophy, you change your thought pattern. Once you change your thought pattern, you change your attitude. Once you change your attitude, it changes your behavior pattern and then you go on into some action.”
Or, consider this line:
“If the soup had been as warm as the wine, and the wine as old as the fish, and the fish as young as the maid, and the maid as willing as the hostess, it would have been a very good meal.”
Use the secrets of rhetoric to improve your writing. Over time, what you learn will translate to your speech.⁴
3. Mirror the Greats
This one is simple. Find the great storytellers, listen to the great orators, and read the great speeches.
Start by going back in time. Watch the Martin Luther King I Have a Dream speech or read Churchill’s We Shall Fight on Beaches. Listen to Armstrong as he stepped foot on the moon. Watch how Obama inspired America in 2008. Examples are everywhere. Kennedy. Robbins. Sinek. Peterson. Ziglar.
Watch the speeches and read the transcripts. As you do, take note of their delivery — the cadence, the rhythm, the undulation, the confidence, and the word choice.
Improving Your Speech
Improving speech is simple. Start with Bucket #1 — what to start doing. Then, move on to Bucket #2 — what to stop doing.
Take advantage of the incredible moment we live in. Through YouTube, you can re-watch history’s greatest speeches, and you can re-read them on the internet — for free. Watch them, read them, and emulate them.
Over time — through a cycle of subtraction and addition — your speech will improve immensely.
² A note from a reader: Writing can help in an additional way: by putting something down on paper, I often feel like I’m committing to it more than if I simply think that same thought. And so it forces me to more explicitly test that assumption. It’s easier to gloss over flawed logic in my head and accept it unknowingly. But putting something into physical form seems to force a level of rigor, probably because it opens up the opportunity for someone else to see what I’ve written and contest it. In other words, writing is inherently social / public, and if there is anything our mind hates, it’s being proven wrong. And so putting a thought into physical form naturally demands more rigor out of us, and therefore makes us much more able to confidently and eloquently speak about the relevant subject as well. Because we have actually thought through it more rigorously than we would have otherwise.
⁴ Each time you come across a new technique, write it down. Next time you’re writing, find a way to use the technique in a sentence. Implementation will accelerate your learning.
This book project requires an extensive research process. I plan to conduct many interviews with writers, influencers, and entrepreneurs. The interviews will all be public and will live right here on my website. We’ll go on this journey together — you and me. Together, we’ll cross industries, speak with experts around the world, and explore the past, present, and future of Naked Brands.
If you have ideas or feedback, please send them my way. You can find my contact information here. I look forward to hearing from you.
Brent founded adventur.es in 2007 with the goal of an organization that allowed him to do what he loved, in places he enjoys, with people he admires. Since then, adventur.es has made over 50 investments and ranked on the 2011 (#28) and 2017 (#428) Inc. 500. Brent reads a lot, writes occasionally, dabbles in wine-making, and was nominated for a VH1 Do Something Award for helping his hometown of Joplin, Mo. recover from the devastating tornado.
This is my second interview with Brent. My first interview with Brent was on the North Star Podcast. Ever since that first conversation, I’ve turned to Brent for wisdom on life, learning and business. One thing is for certain: The world needs more people like Brent Beshore.
Enjoy the interview!
David: Morgan Housel once wrote: “Marketing is increasingly cheap. Trust is increasingly expensive.”
And as you’ve said, “marketing and sales are the lifeblood of any organization.” You’ve also said, that content is an overrated way to get people to your website but an under-rated way to scale education and trust. What’s your philosophy on content as a way to push people down the sales funnel?
Brent: All marketing is content marketing. It’s redirecting attention, at scale, through a message. Once you have the attention, you can educate the person on your product’s features, advantages, and benefits. And/or, you can build trust. The purpose is to sell something, to change behavior, and people are almost always buying behavior.
The first challenge is getting people’s attention, which is different than interrupting them temporarily. Real attention requires you to help, which is why most marketing is ineffective. Buying a million cheap clicks isn’t nearly as valuable as getting a beautiful, entertaining, informative message into five hundred of the right peoples’ hands.
The problem with traditional “content marketing” is the chain of value that must be constructed to change behavior. For instance, let’s say I write an op-ed for the Wall Street Journal and the purpose of it is to generate leads for my consulting firm. Here’s what you have to believe to make it worthwhile: Out of the two million people who viewed the article, perhaps five percent of them actually read it. Now we’re down to 400,000 readers. Of those readers, perhaps 1/10th of 1% of them clicked my byline to read who I am. That’s 400 people. Of those 400 people, perhaps one or two of them is a qualified potential customer, which has a 10% chance of eventually buying my services. So for all the time and money I’d spend getting myself in a position to write for the Wall Street Journal, it’s an incredibly poor lead generation tool.
But when used differently, that same article can be brilliant. What if I took the article that was published and prominently displayed it on my website? Now people who are already interested in my firm and trying to learn more can find it. Buyers like proof points and having the WSJ hand stamp gives it more weight. Then provide a modified copy to the sales team to help start conversations with new customers, or reinforce our expertise with existing customers.
Marketing is like investing and, in some ways, is investing. You’re allocating resources to generate a return on invested capital. Like investing, you always want to understand what you have to believe for it to work out. If the type of investing doesn’t make sense, it’s highly unlikely to work. You want no-brainers.
Brent Beshore (second to the right) with Warren Buffett
David: Your point about “no brainers” sounds like something Warren Buffett would say.
Shifting the conversation here: From elementary school to high school, to college, we essentially run the same race and compete for limited spots. We’re trained to compete. You do the opposite. You look for inefficient markets, where there’s little competition. In our current landscape, how would you advise somebody looking to build trust and generate attention for their business?
Brent: Marketing will only get you where you’re going faster. If your product isn’t valuable, marketing will help put you out of business, fast.
The best way to build trust and generate attention is to be relatively excellent. I say “relatively” because some markets are more efficient/mature than others. The less developed a market, the less valuable you have to be in absolute terms. You just have to be better than everyone else. I don’t want to try to outcompete smart, well-read, and hard working people. I want to find the lowest bar to jump over and then get good at pole vaulting.
Picking your field is arguably more important to your success than your current skill and future capacity. In some segments of business, everyone makes lots of money and the very best do outrageously well. In other areas, even the very best often declare bankruptcy. It’s a base rate analysis. Assume you’re only going to be mediocre, then explore what business and life look like if that’s true.
So choose your field wisely and get good at what you’re doing before trying to make noise.
David: The idea of finding small hurdles and learning to pole vault is so, so good. Going to put that one in my back pocket! That reminds me of another Brent-ism: Concentration Risk.
As you once said: “The special sauce that allows most companies to prosper is a form of human equity. It’s specialized knowledge about how a system works, or some hard-to-gain expertise, or a handful of high-value relationships. People leave, die, or get addicted to something unfortunate and go off the rails. The more concentrated this human equity, the higher the risk.”
Naked Brands may be susceptible to concentration risk. Their success often depends entirely on the founder, which can make them a risky investment.
How would you think through this dilemma?
Brent: Almost always, the smaller the company, the greater the concentration risk, because the owner(s) can’t/won’t invest in systems that live beyond individuals. A sales system that can take ordinary people and produce extraordinary results creates similar outcomes as the superstar salesperson, but is 10X more durable. On a risk adjusted basis, it’s also 10X more valuable because the system can’t get hit by a bus.
A brand can work similarly. If one person’s charisma, intellect, and vision cause a meteoric rise, that same person can cause a catastrophic failure that has nothing to do with the underlying product. Take Elon Musk as an example. Compared to other car companies, Tesla’s share price looks absurd by any valuation technique short of the elusive erratic tweets per car manufactured ratio.
Why?
Because investors believe, at least for now, that Elon can transform the transportation industry and perhaps cure cancer accidentally along the way. So when he acts erratically, it sends a shockwave through expectations. Ironically, pre-Cheech and post-Chong Tesla is identical. The difference is Elon’s brand and how much it induces an investor to believe in the future.
Small, boring companies usually share the same risk. If Bob of Bob’s General Contracting can acquire a reputation for reliability and honesty, he can usually create one heck of a business by personally engaging with his customers, employees, and suppliers. But like Musk, if Bob suffers a heart attack, or becomes friends with Joe Rogan, the business can quickly suffer.
The solution is to build equity in the business brand and/or a collection of brands, while always diversifying away from one individual. The first solution is fairly straightforward: don’t name the business after an individual, or make one person the star. The second is the Wu Tang Clan approach. Create a collection of voices that carry similar weight. Ritholtz Wealth Management has done an excellent job of this in recent years. In fact, I’m pretty sure they’ve pioneered a new business model that combines loosely affiliated media brands in a franchise system. It’s fun to watch and I bet they end up becoming a far larger organization over the next 5-10 years.
Brent Beshore
David: When I think of “Naked Brands,” I think of sexy businesses. How can the Naked Brands concept of transparency, an active online presence, and consistent communication with current and potential customers apply to small, growing private-equity-owned businesses?
I suspect there may be counter-intuitive, under-explored applications of “Naked Brands” ideas for non-sexy, regional businesses like the ones you tend to purchase.
Brent: All businesses are “sexy” to those they serve. I’ve never been more excited to see anyone in my life than when the plumber showed up to fix my overflowing toilet. If something’s not sexy, it’s only because you’re not the target audience.
The mechanics of marketing work identically in every business, although the application varies wildly. Find customers. Educate them on your value proposition. Build trust. Deliver for them. Ask them to tell their friends. For small businesses, it’s just a smaller target audience.
David: You’ve worked in the marketing industry for more than a decade now. It’s a bit of a cliche, but I think it’s true: We’ve gone from a world where content is scarce to a world where it’s abundant. I have so many Chrome tabs open right now! How does the state of modern media inform your marketing strategy at Adventur.es?
Brent: It’s all about attention, which is the reason we don’t have an “outbound” deal sourcing strategy at adventur.es. We’re constantly pounded by marketing messages and distractions, so what good is more shouting? Instead, we try to make sure owners are surrounded by people who know who we are and can offer up something we wrote when they’re thinking about selling. The website is packed with information allowing the seller to educate themselves at their own pace on how we think, what we value, and qualify themselves as a potential partner.
This may seem pedestrian, but it’s not. Useful content attracts the right people, repels the wrong people, and saves everyone tons of time. Now instead of trying to grab someone’s attention and sell them on why they should let us buy their company, they’re coming to us and asking to start a conversation. And instead of starting at zero, we’re able to jump hours into the conversation with no fatigue.
David: Last question: in your study of history, where do “Naked Brands” style ideas pop-up?
Brent: “If we are uneducated we shall not know how very old are all new ideas.” – G. K. Chesterton
David: Closing it with a bang. What a quote! It reminds me of a quote from John Hegarty: “The Originality of an idea depends on the obscurity of sources.” Thank you, Brent.
It’s a law of the universe: Creativity always starts at the edge.
Humans are social creatures. We’re tempted to follow the crowd; we’re tempted to flock to the main stage; and we’re tempted to do what everybody else is doing.
“It happens around the edges: At any gathering of people, from a high school assembly to the General Assembly at the UN, from a conference to a rehearsal at the orchestra, the really interesting conversations and actions almost always happen around the edges.
If you could eavesdrop on the homecoming queen or the sitting prime minister, you’d hear very little of value. These folks think they have too much to lose to do something that feels risky, and everything that’s interesting is risky.
Change almost always starts at the edges and moves toward the center.”
The L-Line Theory of New York Culture
Seth knows Where the Wild Things Are.
His observation reminds me of my “L-Line Theory of New York Culture.”
In New York, culture runs along the L-Line. Culture begins in Bushwick, where rents are low, the parties are wild, and the streets are covered in graffiti. Bushwick is crazy and unpredictable. Last time, I was in Bushwick, I walked by people dressed like Tigers, watched a woman pull her boyfriend on a leash, and met a man dressed in a tie-dye purple Grateful Dead shirt who insisted he’d drank 50 beers the night before.
Bushwick is nuts.
Over time, creative ideas trickle towards Manhattan. Williamsburg takes the best of Bushwick and profit from it. Rents are high, hotels are fancy, and the fashion is eclectic. Williamsburg is corporate, yet artistic. It has one foot in the creative pool of Bushwick and another in the capitalist jungle of Manhattan. Streets are lined with corporate graffiti, Etsy-style vendors, and overpriced artisanal restaurants. Williamsburg is a case study in gentrification.
In Chelsea, the gentrification ended a long time ago. There, you’ll find multi-billion dollar corporations such as Google and MLB Productions. Next door, you’ll find the Whitney Museum, which provides “the most expansive view ever of its unsurpassed collection of modern and contemporary American art” according to its website. From media, to technology, to the visual arts, cultural icons have laid their roots in Chelsea.
From Chelsea, information flows directly to newspapers like the New York Times and TV networks like CNN, who shape thought and culture.
The L-Line lineage — from Bushwick to Williamsburg to Chelsea to the World-At-Large — begins in the dark backrooms of closed-down warehouses and ends in the bright lobbies of thriving, multinational institutions.
Bushwick Street Art
Why Hip-Hop Began in the Bronx
Hip-Hop culture moves along the 4-5-6 Line.¹
Traditionally, the Bronx was home to many different cultures. Latin rhythms and Konga drums roared through the borough. The constant sound of drumming in multi-cultural communities led to hip-hop breakbeats:
“Drums were key to the sonic universe of Latin music and then, the Bronx. Black culture meets Latin culture.
In the 70s, outdoor parties were allowed to happen because the NYC police had major budget cuts which meant the party wouldn’t get shut down. Cops focused on the violence instead of the music, as long as they remained peaceful. The Bronx was viewed as a war zone, so cops didn’t stop outside parties or graffiti art.”
The major music labels are in the heart of Manhattan, right on the 4-5-6. Sony Music Entertainment is right off the 23rd Street stop, and Atlantic and Universal are within walking distance of the 53rd street stop.
Whether it’s Bushwick or the Bronx, creative ideas trace the subway tracks and make their way to the heart of Manhattan.
What does New York culture reveal about the world-at-large?
The L (grey) line runs East and West. The 4-5-6 (green) line runs North and South on the East side of Manhattan, the island on the left.
The Internet: Zooming Out
Lessons from Bushwick and the Bronx reveal general truths about the modern world.
We live in the information age. We are knowledge hunters, gatherers, and consumers. We manage daily trade-offs between new and old, fresh and trusted, and exclusivity and dependability.
There are three broad categories of information consumers:
1. The Diggers
Diggers hold the key to Pandora’s Box. They live in Bushwick and the Bronx. They inhabit the unknown and thrive in the vortex of randomness. Like a gold rush at the edge of the frontier, the vast majority of Diggers don’t strike it rich. Diggers operate under their own intellectual gravity, where up is down and down is up. At their best, they’re innovative and creative. At their worst, they’re manipulative and destructive.
2. The Tourists
Tourists arbitrage thought and culture. They borrow fringe ideas, clean them up, and bring them to mainstream consciousness.² Tourists need structure. On one hand, they’re pulled by the pursuit of success and the weight of responsibility. On the other, they’re spurred by the quest to invent and the yearning to explore.
3. The Masses
The Masses operate within clearly-defined, well-mapped territories. They march to the beat of the establishment and operate within traditionally defined hierarchies. The Masses treasure safety and predictability. Guided by tradition, consensus, and social proof, the Masses chase reach and scale. Climb to the top of the Masses, and you’ll have more influence than Alexander the Great. You’ll schmooze with journalists, dine at Michelin Star restaurants, and invite your favorite celebrities over for high-stakes poker on Friday nights.
Digital New York: Information on the Internet
Informational advantages are found in obscure, hard-to-digest sources. As information moves from the boards of 4chan to the forums of Reddit to the front page of the New York Times, the signal to noise ratio increases and informational advantages disappear. As ideas trickle from the fringe to the mainstream, their tone, tenor, and shape transform.
Diggers thrive in exclusive group chats on Telegram, weird Reddit threads, and the nooks and crannies of Twitter-based subcultures. In their search for secrets and undiscovered truths, Diggers confront conspiracy theories, incomprehensible rants, and shirtless commenters who yell at the world in nothing but their underwear.
Even in my podcast interviews, conversations take a turn-for-the-interesting once the microphone turns off.
On the internet, information slowly travels from hidden forums and private conversations to Tourist-friendly channels. Tourists operate in well-mapped areas that aren’t mainstream, such as Medium and podcasts. They trade surprise for predictability. Tourists experience small tastes of the frontier. Nevertheless, like turtles under a shell, they treasure their safety.
One thing is clear: The higher you climb, the bigger the stage; the bigger the stage, the less you can mess around on the edges — Where the Wild Things Are.
Where The Wild Things Are
The color of ideas change as they move from filter-to-filter.
As information gets polished, it becomes easier to understand; as it becomes easier to understand, it reaches the masses; and as it reaches the masses, once-fringe ideas become common knowledge. Over time, ideas become tainted by corporate interests and political agendas. Shared narratives emerge and informational advantages disappear.
Opportunity is almost always inversely correlated with popularity. Likewise, greater risk is almost always correlated with greater potential returns.
Find the low rents. Surround yourself with people who dress like people you only see in movies. Get comfortable with weird parts of the internet.
If you want creativity, stay at the edge. Follow the Diggers — they know Where The Wild Things Are.
¹ This quote was in my notes but I have no idea where it’s from.
² Kevin Kwok has brilliant insights on contrarianism. When I interviewed Kevin on the North Star Podcast, he said:
“I think that a lot of people talk about contrarianism as being against the grain, and having views that other people disagree with. Of course, the challenge is the decision of, ‘I have this view that people disagree with.
Is that actually a good view or a view that people disagree with because it’s a bad view?’
Similarly… it’s hard to judge the people around you because it could be that you have a view that is mainstream in your community, but it’s actually a contrarian view in the larger view of people. My view of contrarianism is that the important part isn’t in having this view that everybody else disagrees with. The important part is bringing it to everyone else, taking that view and causing it to become non-contrarian.
“The people we should be most excited about that have contrarian views are the people who don’t just have them, they then go make sure that those views stop being contrarian and we all believe them. In fact, it’s the people who we look back and say, was that even that contrarian of a view? Actually, we all believe it. And I think that there is too much of a focus on the standing apart and being the one with the unique insight versus the part which is, ‘how do you educate everybody else and bring that back into the mainstream consciousness?’. That is a lot of work and proves that what you were thinking about was actually valuable and important. That’s the part of it that I wish was more focused on, not the part where you just feel hipster.”
Accelerate Your Career by Writing Online
Write of Passage teaches a step-by-step method for publishing quality content. Learn more.
A one-stop shop to find your voice and become a better writer.
