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Brett also shares personal and abstract philosophy that influences his effective, consistent, and infectious presence on Twitter. Kyle’s voice and actions are rooted in the principle of prolific creation: repetition that outlasts the noise. Of course, the conversation ultimately converges on the future of the film industry and the rise and inevitability of streaming as the primary method of box office growth.

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Joining us from Morocco, this episode is full of actionable insights. We discuss Substack, building independent media brands, and a conversation about Amazon and air travel that combined our two worlds of niche study: travel and eCommerce.

Skift is the B2B equivalent of the B2C media brands like Barstool, Hodinkee, and Goop that receive a lot of credit for their innovate revenue and community practices. It’s about time that the average consumer sees the travel intelligence company for what it is – a generational media brand in the works. This 43 minutes is a masterclass in the “zero to one” of building a media brand.

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She’s a former operative at Derris PR where she built the profitable content practice from the ground up. Not only did she thrive on the agency side, she was formerly a marketer at Madewell and a journalist – first in print and then on the digital side for Conde Nast. Her experience is broad. In practice – she is the essence of the study of linear commerce. This is why many in the digital spaces are beginning to view her as a go-to thinker. And I am convinced that one day soon, she will become one of the preeminent consulting partners for progressive Fortune 500 companies on best practices in new media and digital commerce.

Hailing from the Midwest but a city girl at heart, I am proud to call her a friend and a colleague. And you will be, as well. Get to know Grace.

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After fighting homelessness, Taylor attended Virginia Tech. By the age of 19, he started his first company – one that would sell by 21. After dropping out, he would become the VP of marketing at Qualaroo (acquired: Xenon Venture). He’d go on to found MilliSense in 2014 and then become the CMO of Sticker Mule and a growth strategist for Microsoft. Taylor then led marketing for Skurt (acquired: Fair). And then in 2016, his newest venture PopSocial netted $2 million in year one, only to be wound down.

He founded a company with actress and businesswoman Zoe Saldana and shortly after became the CMO of Artsy. He has been awarded Social Media Influencer of the year in 2016 by Black Enterprise and he was awarded Forbes 30 Under 30 in 2018.

This is a truly fascinating conversation with the admitted “street entrepreneur” and college dropout turned go-to marketing executive. He proves that no path is a necessary path for a great destination. He’s certainly made it.

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At the crossroads of media and commerce, Anthony proposes an alternative structuring of the agreement between Barstool Sports and Penn Gaming, the company that recently acquired them. Web and Anthony also discuss the educational system, higher education, the concept of credentialism, and what it all means in the present and future moments.

This is a truly fascinating conversation.

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The idea behind Gumroad was simple: Creators and others should be able to sell their products directly to their audiences with quick, simple links. No need for a storefront.

I built Gumroad the weekend I thought up the idea, and launched it early Monday morning on Hacker News. The reaction exceeded my grandest aspirations. Over 52,000 people checked it out on the first day.

Later that year, I left my job as the second employee at Pinterest — before I vested any of my stock — to turn Gumroad into what I thought would become my life’s work. [1]

Lavingia languished in the spotlight until growth stalled.

We grew the team. We stayed focused on our product. The monthly numbers started to climb. And then, at some point, they didn’t.

Gumroad has become a stalwart in the creator economy because of Lavingia's next steps. From nearly shuttering to a profitable, lifestyle business: Gumroad has fueled millions in monthly commerce for content creators. It's spawned competition from platforms like Patreon, Memberful, and now Substack. But I wouldn't count the founder out. Lavingia is playing a long game, he's growing on cash flow, and he has a specific vision for the creative future. In fact, he's planning an active role in it.

Known for his insightful tweets and quick wit, Lavingia is now raising a fund to continue acting on his intuitions. From funding underrepresented minorities to new proponents of internet-born creativity, the Creator Economy is just beginning. He's taken it upon himself to make it more accessible. For Sahil Lavingia and Gumroad, they're well positioned to profit from it.

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Thompson hosts The Atlantic’s latest podcast Crazy/Genius, which was nominated for an iHeartMedia Best Podcast in its first year, and is a weekly contributor to “Here and Now,” the national afternoon news show on NPR. He is a regular guest on CBS, the BBC, and MSNBC, has appeared on Inc and Forbes’ “30 Under 30” round-up, as well as Time magazine’s 140 Best Twitter Feeds. [1]

In his latest deep dive at The Atlantic, Thompson covers a prescient topic. How will the pandemic effect retail? Here’s an amazing excerpt from his latest:

By obliterating the face-to-face economy, the coronavirus will return Americans to a blend of virtual commerce and home prep that is reminiscent of the late 19th century. In the 1890s, Sears, Roebuck delivered a bible of goods to the doorsteps of families who cooked at home. In the spring of 2020, Amazon and its ilk deliver an infinitude of stuff to the front steps and mailrooms of families who couldn’t dine out even if they wanted to. [2]

Our discussion was a spirited one. Thompson believes that the suburbs will grow as retail shutters and eCommerce adoption grows. I believe the opposite. I see a clear path to a stumbling suburban ecosystem where commercial real estate’s degradation drags down residential real estate prices. We also discussed over-retail and its influences.

From The Ballad of Victor Gruen:

Today, multiple malls and shopping centers exist for every small suburb in America, designed and constructed with no expectation to achieve sustainable demand. Meanwhile, America is accelerating into urbanization with our growing GDP as the wind at its back. Direct-to-consumer brands are developing, eCommerce has grown to nearly 18% of all retail sales, and urban town centers are popping up – each taking cues from Gruen’s original vision.

This is one of the most interesting conversations that you’ll hear on the juxtaposition of retail, eCommerce, and real estate.

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Sarah Frier is a notable reporter on social media companies for Bloomberg News where she's an expert on Facebook, Instagram, and Snapchat, and Twitter. Her work is featured in Businessweek and a Bloomberg Television. Prior to Bloomberg, she attended the University of North Carolina, where she studied journalism and edited for the university's school paper. This is her first book. The New York Times cites the relevance of the book with:

A sequel to The Social Network. 

Here's a summary of the book via Simon and Schuster: 

In 2010, Kevin Systrom and Mike Krieger released a photo-sharing app called Instagram, with one simple but irresistible feature: it would make anything you captured through your phone look more beautiful. The cofounders started to cultivate a community of photographers and artisans around the app, but it quickly went mainstream. In less than two years, it caught Facebook’s attention: Mark Zuckerberg bought the company for a historic $1 billion when Instagram was just 13 employees.

That might have been the end of a classic success story. But the cofounders stayed on, trying to maintain Instagram’s beauty, brand, and cachet, considering their app a separate company within the social networking giant. They urged their employees to make changes only when necessary, resisting Facebook’s grow-at-all-costs philosophy in favor of a strategy that highlighted creativity and celebrity. Just as Instagram was about to reach 1 billion users, Facebook’s CEO Mark Zuckerberg—once supportive of the founders’ autonomy—began to feel threatened by Instagram’s success.

At its heart, No Filter is a human story, as Sarah Frier uncovers how the company’s decisions have fundamentally changed how we interact with the world around us. Frier draws on unprecedented exclusive access—from the founders of Instagram, as well as employees, executives, and competitors; Anna Wintour of Vogue; Kris Jenner of the Kardashian-Jenner empire; and a plethora of influencers, from fashionistas with millions of followers to owners of famous dogs worldwide—to show how Instagram has fundamentally changed the way we shop, eat, travel, and communicate, all while fighting to preserve the values which contributed to the company’s success. No Filter examines how Instagram’s dominance acts as lens into our society today, highlighting our fraught relationship with technology, our desire for perfection, and the battle within tech for its most valuable commodity: our attention.

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When I finished it in December 2019, it was just three days after I opened to page one. There was one paragraph that really caught my eyes. And from then on, I zoomed through. From page 34:

Brailsford had been hired to put British Cycling on a new trajectory. What made him different from previous coaches was his relentless commitment to a strategy that he referred to as “the aggregation of marginal gains,” which was the philosophy of searching for a tiny margin of improvement in everything you do. Brailsford said, “The whole principle came from the idea that if you broke down everything you could think of that goes into riding a bike, and then improve it by 1 percent, you will get a significant increase when you put them all together.

This particular lesson was on the effects of compounding improvement, especially the infantismile ones. Clear's life is made of these moments and so are ours. Like many of you, Clear values the pursuit of deep generalism and optimizing the abilities, influence, and opportunities that you possess.

But James doesn't merely report the research of others. He tries out the concepts for himself as he experiments with building better habits as an entrepreneur, writer, and weightlifter. In the end, his talks end up being one-part storytelling, one-part academic research, and one-part personal experiment, forming a colorful blend of inspirational stories, academic science, and hard-earned wisdom. [1]

I am proud to have hosted him. Clear is a friend and I'd even call him a mentor. You will be better for listening to this one hour episode.

New: the RSS feed can be found here.

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From her site:

Emily Schromm is a Nutritional Therapy Practitioner, personal trainer and serial entrepreneur who helps others empower themselves by way of food and movement. Her journey with nutrition began after realizing she could use food to heal from the inside out, and her passion for teaching others how to do the same, specializing in gut heath, adrenal repair and herbal remedies, has led to a career spanning five companies and three verticals of business including online programming, physical products and a brick and mortar gym, Platform Strength in RINO, Denver. She most recently self-published her first book, The Process, and launched an online monthly digital publication, EMPRESS.

Since her time as a fitness entrepreneur, Emily has evolved into a media and commerce professional. But before that, she accomplished something that few of us have: professional and social balance. The project that she runs today is representative of this balance. A philosophy that she describes in her book, “The Process.”

Emily has accomplished a great deal as a bootstrapped direct-to-consumer founder. She’s a consummate learner and a deep generalist. But by the end of this episode, you’ll learn that she’s just beginning. One thing you’ll hear is that it’s free-flowing and friendly. It’s as if we’ve known one another for a long time – even if we’ve forgotten how we met. Enjoy our conversation.

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By the age of 13, he published a book on British heraldry that is still sold in museums. A nomad of sorts, he landed in a small preparatory school in urban Boston where he quickly picked up rowing as a sport. A unnatural fit for the 5’10” athlete, he’d go on to become a member of Georgetown’s lightweight men’s team and eventually become the 110 lb coxswain of the U.S. National Team (a weight loss feat that even he cannot comprehend). While at Georgetown, he studied in a select program that prepared leaders for government service, foreign and domestic.

A bronze medalist, he came home to teach classics and philosophy at an elite preparatory school before leaving academia, altogether, to build a direct-to-consumer brand from scratch. In the midst of all of this, he’d go on to earn his PhD in archaeology from Oxford University while rowing for the institution’s fabled boat house. In a build up that sounds like a prequel to Indiana Jones, the guest’s latest venture is one that combines his experiences like a collection of oils on a canvas.

Jack Carlson is the enigmatic founder of Rowing Blazers, a brand that bends fashion genres – attracting new audiences to classical wares. To Carlson, he’s building the next great American brand. From streetwear aficionados to champions of the Head of The Charles regatta, they’re finding themselves on the canvas that Carlson and COO David Rosenzwieg have painted over the last four years with the help of Jack’s girlfriend (and national collegiate rowing champion) Keziah Bell.

In a article for Esquire, Ben Boskovitch writes:

Of late, no one has been doing collabs more excitingly than the coolest name in prep right now, Rowing Blazers. In the past year, the brand has put together some seriously envy-inspiring team-ups, including, but not limited to, a capsule collection with streetwear cult brand Noah, a sweater I still dream about in collaboration with Prep Mount Rushmore brand J.Press, perhaps the coolest damn bar merch I’ve ever seen, and a mind-changing execution of the sometimes polarizing Nantucket Red.

The products are designed to appeal to a psychographic of consumers rather than a demographic of them. You won’t find the racial or socioeconomic exclusivity seen in brands like Kiel James Patrick, for instance. Instead, Carlson collects his experiences (many of which are covered in this episode) and finds common bonds where other retailers tend to find differences. As a result, you have a preppy brand that appears to welcome streetwear fans, skaters, and even lame dads (like yours truly).

What’s most surprising about Rowing Blazers‘ growing appeal is that the founder had no fashion experience. Yet, Carlson and his small team source a number of fabrics to piece together new styles that are generally manufactured in the United States. The complexity of this operation is tremendous. The passion and devotion to each product reflects the time and effort spent on perfecting each “drop” or brand collaboration. In GQ magazine, Samuel Hine addresses the elephant in the room:

Carlson is an unlikely entrant in the N.Y.C. men’s fashion scene, precisely because he does have an uber-prep résumé. When we meet for breakfast at The Odeon, he is wearing a Tintin sweatshirt, Noah x Rowing Blazers sweatpants, and Sperry sneakers from a forthcoming collab. Thirty-one years old, he has the slight build of a former coxswain and a boyish laugh—a quick ha-ha—like he’s just told a dirty joke in the steam room at the Racquet Club. Carlson attended Georgetown and then Oxford, where he got a PhD in archaeology while racing for the university’s storied boat club. He did three stints on the U.S. national rowing team, coxing a boat to a bronze-medal finish at the 2015 world championships.

Jack’s education was that of a deep generalist and it shows. He is an extraordinary talent that seems to be building a brand that will last. His perspectives on how and why he chose the retail industry to innovate is worth your time.

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I know how to win arbitrages.

When I started the Polymathic Audio Project, I set out to find modern examples of polymathic thinkers. By the time that you’re done with episode, you’ll view Vaynerchuk through a different lens. He’s accomplished more than most; the architecture of his business holdings suggests that the upstart has yet to be realized.

VaynerX holdings features the following operations:

VaynerMedia: a full service digital agency that services Fortune 500 clients. Reportedly profitable, Vaynerchuk mentioned that the agency earned over $200 million in 2019.

Tracer: a data platform for marketing efficiency. The early platform has managed over $750 million in marketing across 50 global brands.

Gallery Media Group: a portfolio of media brands to include PureWow, Blink, 137pm, Mom Brain, The CMO Podcast, and Fashionista.

Sasha Group: a marketing and consulting firm for small businesses generating $1M and $100M in revenue.

VaynerProductions: a production and animation lab that focuses on storytelling and impacting culture.

VaynerSpeakers: a speakers bureau built to facilitate modern event planning. The bureau consults organizations and provide speakers of range and impact. Speakers include Dominique Dawes, Sarah Kunst, Ryan Holiday, Andrew Brandt, and Amy Landino.

A brand machine: PureWow provides validity to his DTC brand.

In addition to these VaynerX properties, Vaynerchuk runs the following operations:

Green Street: a full service creative agency agency dedicated to cannabis brands.

WineText: an eCommerce cart that optimizes for frictionless payments through SMS.

Empathy Wines: a DTC brand that features affordable wines of top quality.

VaynerSports: a full service athlete representation agency that commits to guiding players though issues on the field and off.

Related Companies: is a partner to VaynerX. Miami Dolphins and real estate tycoon Stephen Ross maintains a personal interest in Vayner properties.

Minnesota RØKKR: co-owner of the eSports team alongside the Minnesota Vikings owners, the Wilf family.

Wine Library: where it all started. Vaynerchuk’s first big moment came when he was handed the keys to his father’s liquor store. He took it from offline to online in an effort that grew the company from $3 million to $65 million in annual sales.

And though that may be more than enough for one professional, that’s not all. Gary’s work and personal brand have placed him at an interesting spot. He’s one of the most influential business people in hip hop. He’s trusted by many up and coming rappers thanks to his longtime partnership with manager and promoter Mike Boyd. The New York Times recently featured this side of Vaynerchuk.

This is only the beginning, according to Vaynerchuk, who hosted a Budweiser-sponsored Super Bowl party this year featuring entertainment from Grizzley, Keed and YG. (Lil Keed, Vaynerchuk said, almost made an appearance in a Mr. Peanut Super Bowl commercial that featured Alex Rodriguez, but it wasn’t to be.) [1]

What struck me most about this conversation with Vaynerchuk is just how badly his mind is needed in consumer goods and direct to consumer retail. He’s a legitimate veteran in eCommerce. He understands the principles of linear commerce [2]. His patience is long and his understanding of business leverage is unparalleled. I’m convinced that at some point, 2PM Inc. and VaynerX will partner to help facilitate the growth of direct brands. I’m not sure that even Vaynerchuk realizes that he’s built a corporate promotional machine that could survive without his personal branding efforts.

Vaynerchuk is a polymathic thinker by definition. Unconventional, curious, and skilled, he’s built an empire that’s valued well into the hundreds of millions. But rather than start with his beginning, we start with his end game: buying the NFL’s New York Jets. It’s a goal that he’s publicly championed for over a decade. For the longest time, onlookers scoffed at the idea. It’s clear that he has a path to achieving that end game. No. 3 of Polymathic Audio is 54 minutes that will impact the way that you think. And it may influence what you do next.

Notice: this podcast contains explicit language. Parental guidance is strongly suggested. 

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Over the next two years, he’d become one of the most prolific producers of quality content on the internet. It’s 2019 and he’s on a tear. His content has achieved a compounding level of success. He’s interviewed dozens of the most notable names across business, medicine, and academia. And Write of Passage, the company began by Perell, now boasts over 220 students in 28 countries. The community builder has nearly 33,000 Twitter followers and his blogs are commonly read by over 50,000 people per post. His theories are simple and the foundation of them all begins with an observation that he’s noted:

You’ll transform from a passive consumer to an active creator, and escape the “Mediocre Majority” of people who endlessly consume without ever producing. The content you produce will become an asset that you own. It will work for you 24/7, and become a magnet for like-minded people, interesting ideas, and career opportunities.

Perell has identified an arbitrage opportunity for brands, retailers, and individuals in content production. According to the writer, speaker, and teacher: “the internet is overwhelmed by content consumers and short on producers.” To change the calculus for you or your company, Perell suggests shifting the strategy: produce content. And produce it prolifically.

One of the capstone moments of the episode is our Kylie Jenner acquisition discussion. This tweet generated quite a bit of disdain, I must admit. But the spirit of the message was: build an audience and you have a distinct advantage. Perell and I share the belief that while none of us are Kardashian’s (yet), anyone can build a powerfully engaged audience. In addition to Jenner, we discuss Joe Rogan’s operation and revenues. But then we do something very important – we take a step back. We talk about practitioners without mega-famous families. We hone in on those who’ve built sizable audiences and communities without the force multiplier of fame. One thing that we’ve found in common, generalists to tend to thrive in that respect. From Gary Vaynerchuk to Casey Neistat – both future guests – they champion their broad experiences and insights.

THE TREND TOWARD SPECIALIZATION

The trend toward specialization has opened the door to generalists. Perell falls into that category. His broad education influences his understanding of life’s many verticals. As such, the conversation between us was natural and free-flowing. When I first met Perell, I didn’t know much about him. I did recognize his ambition and desire for mastery. Today, the 25 year old is beginning to realize the fruits of that ambition.

He’s a bonafide world-shaker. He’s not an influencer in the traditional sense. Rather, he influences those who influence the influencers. From Naval Ravikant to Tren Griffin to Keith Rabois to James Clear to Scott Belsky to Erika Nardini to Seth Godin – he’s a trusted source of thought and practicality. I believe that Episode No. 2 can change things for those who take the time to listen.

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While at Kegler, he helped to incorporate Jeni’s Ice Creams on behalf of founder Jeni Britton Bauer and her husband Charly. He’d later serve as labor and employment counsel to General Electric’s aviation, transportation, and water businesses. This is where things get a bit shifty. Lowe was then tapped to be General Counsel for a small company within GE, somehow leapfrogging hundreds of more experienced and longer-serving GE lawyers. Then during the tumult of the financial crisis, Lowe’s career really took off.

After six years, Lowe left General Electric to join Jeni’s when it was still in its infancy. Then just four scoop shops with no third-party distribution, Jeni’s now lords over close to forty scoop shops and a distribution in over 3,000 grocery stores. Their DTC processes are unlike any other. Each shipment stays chilled with the help of carefully packed dry ice and an unboxing experience that’s second to none. He’s been the CEO for ten years, now. He also serves as a board member with Watershed Distillery, White Castle and the Columbus chapter of Conscious Capitalism International. An avid writer, lover of basketball, father of three, and husband to a titan in her own right.

Lowe has a special partnership with the founder and face of the company. One of the special moments of the podcast is when he explains how they work together and which public figures are most analogous to their proverbial one-two punch. But all in all, it’s his candor that comes across.

There is an honesty, a truth, and a vulnerability that comes across in this 56 minute discussion. In it, I feel like a student asking the teacher for the way forward. And in a digital-first industry filled with strategists and talkers, Lowe is an operator in the truest sense of the term. How and what he’s had to navigate to take the company from a lifestyle business to a private equity-backed growth company is worth your time.

Jeni’s is a household name. Jeni is a larger than life creative mind and force of nature. John is as much an ingredient in the success as the brand’s salty caramel. I’m proud to call him a friend and mentor, inside and outside of the workspace. You’ll be able to hear the admiration in my voice.

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