Austin Rief

The through-line

Rief's consistent argument is that a newsletter is a very simple product that almost nobody executes well, and that the money is never really in the thing you think it's in. The newsletter is the hook; the value is the trusted relationship with an audience that can be sold against, verticalised, or turned into a B2B business. He says this about his own company, where he pitched early angels on the idea that "we're building a relationship with this really valuable audience we don't exactly know where it's going to go but if we can do this and we can get them to trust us then it doesn't really matter it'll be valuable in one way shape or form" [2], and he says the same thing about businesses he has nothing to do with, describing a bingo rave company as an alcohol business that uses bingo to get you to the bar and keep you there [1]. Content, hooks, and gimmicks are distribution mechanics; the business sits one layer down.

The second constant is a wary, empirical pessimism about repeatability. He accepts that he caught two windows nobody else was standing in and that both closed. Where his early years were about growth hacks and scale, his later thinking is about defensibility: which audiences will pay, which niches have a tailwind, and which categories have been made so cheap to enter that the average entrant is worthless. He describes himself, and is described by friends, as the paranoid one in a room of newsletter founders [3].

On what makes a newsletter actually work

He reduces the medium to one variable. "It's great content that is the the first and really only important thing," he says; everything else is the twenty percent, and "the thing that really matters is creating great content" [4]. But he refuses to define great content in the abstract: "it's content that your audience loves it's as simple as that" [4], and he points out that plenty of people find Lex Fridman boring while he pulls millions of views. Morning Brew's own editorial logic came from Tim Urban's observation that "you think you're unique but you're really not" [2]. There was no algorithm and no process behind curation, just reading the Times, the Economist and the Journal each morning and writing it better than they did, on the assumption that people like them would want the same thing [2]. In the early days that freedom, and the fact that he and Alex Lieberman weren't worried about money or mistakes, produced the authenticity he credits for the growth [7].

He's honest that the format tolerates partial attention. He doesn't know how much of the newsletter people read, only that plenty of them click links at the bottom, and that suits him: "there's something for everyone" and readers can skip days and still get value, because it isn't a single dense story [2]. He also warns that content is the hardest thing to fake at scale, since most of what exists is not very good, and depending on your ambitions merely good content still won't get you there [4]. And he notes a peculiarity of the medium for founders: unlike a tech product, a newsletter gives you almost no early signal, because "you're so data poor" [4].

On the three kinds of newsletter, and "Morning Brew for X"

He splits the category into three. Editorial newsletters, the Substack model of a single writer running two thousand or ten thousand words. Aggregation, which is what Morning Brew and The Hustle did, going general and going for scale. And the link roundup, the five bullets on a Friday [3]. The interesting slot, he argues, is a fourth position between them: aggregation with a narrower target, "morning brewer X," where the total addressable market is smaller but tone and coverage let you own a much larger share of it [3]. Milk Road fits his framework exactly, and he calls this the biggest opportunity available: find a growing industry, ride the tailwind, and build something distinct in the niche [3].

The qualifier matters. X works far better when it's B2B or maps to a job title than when it's fly fishing or basketball [3]. On the consumer side, the audience has to be high dollar, "the newsletter for Ferrari owners or the the newsletter for Rolex owners," people already spending hundreds of thousands a year in the category [3]. He is flatly pessimistic about relaunching the general-business, four-million-person email he already built [3]. And he is dismissive of the wave of copycats: their content isn't good, they grew on growth hacks that don't compound, and "I just don't think these newsletters have a ton of value" [1]. His analogy is that "beehive did for newsletters what Shopify did for e-commerce" [1], which was wonderful for the ecosystem and brutal for the median founder, because when starting is trivial "you have to be either the absolute best or you just can't raise a bunch of money" and must accept a merely fine business [1].

On growth tactics and their shelf life

The list-building started as literal door-to-door sales. He would stand in a five-hundred-person lecture hall with a printed spreadsheet and ask people, one at a time, for their email, and he was terrified of public speaking at the time: "well, I'm going to do this, I need those emails" [5]. From there he names three engines. The referral programme is the base load, nearly free apart from swag, driving double-digit growth, "the residual income it's the steady cash flow so to speak that's always there" [2]. Then 2018, when the list went from a hundred thousand to nearly a million on the back of two moves. The first was advertising inside other newsletters, on the insight that newsletter readers are a distinct, unusually engaged subset, so converted subscribers are high quality even when the host audience isn't strictly business professionals; commonplace now, nobody was doing it then [2]. The second was being among the first advertisers on Instagram story ads, which at the time were opt-in and required uploading correctly formatted creative. Subscribers came in at ten and twenty cents, at times three to five cents, and the constraint became Facebook's own systems: an 8pm email telling them they had hit a ten thousand dollar daily limit they didn't know existed [2][4]. He describes the period as adding ten to twenty thousand subscribers a day on a base of half a million, not sleeping for two weeks, "it feels like you're on a drug" [4], and a feeling he expects never to have again.

He is clear that none of it is proprietary for long. "It's a copycat world people have copied us we've copied other people," and Instagram still works, just not at ten-cent subscribers [2]. He deliberately declines to name what's working now, offering to talk about it in two years once it's been copied [2]. His general rule: things always work, they just may not scale the way you want [2].

On funding, leanness, and the accident of timing

He treats his own capital structure as luck rather than genius. In 2015 media was hot and BuzzFeed and Vice were raising, and the only reason they didn't follow is that "no one was going to fund a a sophomore in college" [3]. By the time they graduated in 2017 the sentiment had reversed completely, publishers were burning capital, and the value was accruing to Facebook and Google [2]. So they raised what they called a family and friends round that was mostly friends of friends and the Michigan network, pitching around 150 people and converting 27 into roughly thirty thousand dollar cheques for a total of $750,000, then ran to profitability: break-even in 2018 and quite profitable after [2]. Those two unpaid college years building the brand were, in his account, decisive, and the business would be in a much worse place if they'd started two years later [2].

The money went into two buckets, people or growth, and he weighted growth hard because "it cost the same amount of money to send a newsletter to one person and a million people" [2]. They guessed, without knowing precisely, that about a million subscribers would unlock serious marketing budgets, so they entered 2019 with nine or ten employees while doing hundreds of thousands a month in revenue [2]. That inverts at scale: with around a hundred employees, headcount costs far more than growth marketing [2], and the company he describes later runs 250 people on roughly $70 to $75 million of revenue at a double-digit margin [3].

On B2B, verticals, and why ad businesses are a grind

Morning Brew went horizontal, launching multiple newsletters, while The Hustle verticalised into subscription and events. He doesn't claim his route was better, only that it was the route available: a general business newsletter has a tone and a target customer too diffuse to support a subscription or an event, whereas an edgier, entrepreneur-facing product can launch a Trends or a Hustle Con [3]. What he did fall in love with was the B2B model, reaching retail, HR, marketing and emerging tech professionals with content that makes you better at your job [2][3]. The economics were the appeal: "we'd launch a newsletter and be break even before we even hired the writers because we pre-sell" an advertiser, typically a B2B SaaS company, into it [3]. His read is that this path made a hundred million of revenue easier for them, while the vertical, multi-revenue-stream path was the easier road to a billion-dollar company over eight to ten more years [3].

He defends the incumbent B2B publishers against the charge that their content is weak by separating simple from easy. Their playbook is well defined, "there's no crazy tech," no machine learning, just content that resonates with ads sold into it, but scaling across every vertical without a misstep is hard [3]. Ad businesses carry heavy fixed costs in writers and salespeople, and unlike SaaS you start each year with none of your revenue locked in by renewals, so the gap between a twenty percent margin and a twenty percent loss flips easily [3]. The way to beat them, he argues, is "to treat B2B like consumer," treating readers like people the way Milk Road does [3]. He has also talked publicly about which media companies he's obsessed with and how Morning Brew multiplied its revenue fivefold in a year [6], and about which elements he thinks determine whether a media business works at all [8].

On having an enemy

He believes competition should be personalised: "I think it's always good for a business to have an enemy" [3]. The first enemy was theSkim, quickly discarded once he concluded you can't raise twenty-five million for a newsletter and still exit well; then the enemy became The Hustle, and he admits he manufactured the animosity out of immaturity, seeing Sam Parr as abrasive at a point when "I wasn't principled. I didn't have real values at the time" [3]. What the rivalry produced was obsessive craft. Lieberman printed both newsletters every single morning and they went through them line by line arguing over which sentence was better, for six to nine months, to the point of near-revolt among staff when he conceded a Hustle line was stronger [3]. They wrote their open rate on the wall at 11am every day for about two years, "the great wall of opens" [3]. His verdict on the comparison is that neither was better, they were catered to different people, but the intensity was the point: "I've never been as hyperfocused as I was in 2018 on us writing the best newsletter, growing the best newsletter, and selling it" [3].

On passion audiences and businesses that are a pain in the ass

Asked where he'd go if media were off the table, he names two destinations: B2B, because businesses with fifteen dollar lifetime values are brutal and he'd rather sell significant enterprise products, and passion audiences, which is where he'd actually go [1]. The specific obsession is meat smoking. He agrees with the principle that anything people willingly put themselves through enormous inconvenience for is a money-making category, and smoking qualifies: ten to twelve hours at two hundred degrees, wood pellets, friends waking at four in the morning to start a brisket [1]. The model is razor and blade. Trager sells the fifteen-hundred-dollar smoker and then fifty dollars of pellets every cook, and he wants to build the competitor: "sell the $1,500 product sell the $50 a month $100 a month pellet and build the next Trager which I think is a multi billion dollar brand" [1]. The distribution is already there in smoking influencers in Nashville and Texas doing tens of millions of views on how to smoke a ribeye, sophisticated operators who nonetheless take no big swings and build no product [1]. He prefers working with them precisely because they aren't New York or TikTok influencers: people who love life, want to smoke meats, and would be happy to sell a grill [1].

The same eye explains his fascination with physical, experiential businesses despite running a digital one. He describes bingo raves, Bingo Loco and Bongo Bingo USA, taking over venues on their slow nights, using the existing infrastructure and adding hosts, performers, confetti and lip-sync battles, selling thirty to fifty-three dollar tickets and reportedly grossing around twenty million a year [1]. What interests him is the retention mechanic: like the shuffleboard bar in Brooklyn, the game is what keeps you in the room for hours buying drinks [1]. His post-Covid thesis is that people want to get out of the house and do something more interesting than standing in a bar, and he loves visiting these places to see how they hook people, because hooking people in a newsletter is easy by comparison, it's content every day, while in-person businesses have to earn the return visit [1].

On the creator economy and the power law

He is bullish on the pie and bearish on the median. Content has "zero marginal cost to create," which is wonderful and also means anyone can do it, so attention distributes on an extreme power law, made worse online because location and time have been removed as constraints [4]. His conclusion is that the top of every category becomes vastly more valuable: "the best English teacher in the world can be a billionaire," because you'd rather learn from the best in the world than the best within driving distance [4]. Saturation is not the objection people think it is; a hundred people already make investing podcasts, and the All-In group still broke through on format, point of view, intelligence and humour [4]. But he expects the rewards of the creator economy Renaissance to be captured almost entirely by the top few percent [4][11].

The force behind that concentration is the parasocial bond. He argues audiences build a genuine relationship with people whose voices they hear weekly for years, which is why meeting a podcaster feels stranger than meeting a film star, and why people approach him as though they know him [4]. That's the power of content, and the reason influencers convert. He also observes that the ceiling on a creator is set by temperament rather than craft. Talking with Jimmy, he found someone who is just a guy socially but has "this Steve Jobs this Elon Musk in him," maniacal and unstoppable about anything he decides to do, offering ten grand at one in the morning to get a gym opened so a game of horse could happen [4]. The combination of a creator's craft with an entrepreneur's resilience is, in his phrase, scary [4].

On career decisions, optionality, and guarding time

He describes his own route into finance as pure conformity, going to Michigan's business school where "I was a sheep following the herd" straight at investment banking [3][5]. What broke it wasn't Morning Brew's success but the internship itself, several all-nighters and a fortune cookie taking a dig at bankers, after which he concluded he didn't want that life [2][3]. The decision to go full time was made on downside rather than upside: he wasn't especially bullish on Morning Brew becoming a multimillion dollar business, but "I was bullish on the optionality it gave me" and confident he could get a banking job again if it failed, which made it a win-win [2]. He also credits investor scepticism, including a blunt rejection from a Michigan professor whose reasoning he says he doesn't blame, as fuel, while noting how easy that is to claim in hindsight [5].

On his own attention he is deliberately, admittedly selfish. His rule was "never get lunch on a Tuesday," born of watching a more successful friend propose two-hour midday lunches while he and Lieberman were grinding [4]. He says no readily to podcasts and advice requests, reasoning that time is precious, that family, friends and work come first, and that he wants to be the best version of himself before positioning himself as a mentor, with the hope that the balance shifts as he frees up time [4]. He's also candid that being good at something doesn't make you good at explaining it: newsletters feel so basic to him that he forgets how much he's learned, and "often times the most knowledgeable person is not the best teacher" [4]. On the operating side, he describes hitting a point where he could tell something was wrong without being able to name it, and the diagnosis was structural: no plan, no vision, no values, no alignment [4].

Takeaways

• Treat the visible product as the hook and the business as what sits underneath it: bingo is an alcohol business, and a newsletter is a trusted audience relationship you monetise later [1][2].
• The best remaining newsletter opportunity is "morning brewer X," aggregation aimed at a growing niche, and X should be a job title or industry rather than a hobby; consumer only works if the audience is high dollar [3].
• Advertise inside other newsletters, because newsletter readers are a distinct high-engagement population and convert into unusually good subscribers [2].
• Be early to new ad formats and prepared before they launch; Instagram story ads bought subscribers at ten to twenty cents, and none of it lasted [2][4].
• Ad-supported media has no renewal base, so heavy fixed costs make the flip from a twenty percent margin to a twenty percent loss easy, unlike SaaS [3].
• Cheap tooling has made newsletters what Shopify made e-commerce: easy to start, so you must be genuinely the best or accept a merely fine business [1].
• The razor-and-blade opportunity he'd chase is a Trager competitor in meat smoking: a $1,500 device plus recurring pellet revenue, aimed at an obsessive audience already served by influencers who take no big swings [1].
• Keep the team lean while buying growth, since a newsletter costs the same to send to one reader or a million, and headcount only overtakes marketing as the dominant cost later [2].