Framework
The fewer people loud in your industry, the bigger the content opportunity
Shaan's heuristic: opportunity to win attention is inversely proportional to how many people in your field already blog, tweet, or podcast. Backwards, private, closed-door industries offer a far bigger opening than crowded ones like tech.
“Yeah, basically the fewer the people, the less common it is for people in your industry to be blogging or tweeting or podcasting, the more of an opportunity there is for you to go do it. There is an insatiable appetite for this stuff. And if your industry is sort of backwards, slow, it's private behind closed doors, bigger opportunity for you than it is for guys like us.”
Steal thisBecome the loudest content creator in a quiet, unsexy industry before anyone else claims the spot.
Story
How Capital Daily started: a MailChimp account and a stay-at-home mom
Frustrated that his local Victoria paper had laid off its journalists, Wilkinson started a local news newsletter, Capital Daily, with a stay-at-home-mom writer and a MailChimp account, then discovered ads for local-news subscribers were dirt cheap because no one was competing.
“I went to a friend who is a stay-at-home mom who had some experience doing a bunch of writing. And I said, hey, why don't we just start a MailChimp account and we'll come up with a brand. We called it Capital Daily. And we'll send out a daily newsletter and we'll just summarize like, hey, here's like 3 or 4 stories of things that are happening in town. So we start doing this and, uh, I have a friend who runs a PPC agency and I get him to just go buy ads. And I realized I can buy ads for like nothing. No one's advertising for local news.”
Fact
Local news is winner-take-all — so buy your way to scale fast
Wilkinson's local-news thesis: historically there's one dominant paper per city, so he spent $100–200K on ads to race to ~25,000 subscribers fast, then hired a CEO (Farhan) who had scaled Vancouver's biggest local news site to monetize it.
“I realized that in local news, usually there's one winner, right? So historically there's usually been one big newspaper. And so I was like, how do I get this as big as possible, as fast as possible? And I was also just impatient. I was like, I have money. I can afford to do it. I'm just going to spend like $200 grand on ads. And so we spent, I don't know, $100,000, $200,000. And very quickly we got to like 25,000 subscribers.”
Steal thisIn winner-take-all local markets, spend aggressively on ads to grab the dominant audience position before competitors wake up.
Idea
Hyper-local news newsletters to replace the dying local paper
Shaan loves Andrew's idea of running a one-or-two-writer newsletter covering a single city, effectively replacing the local newspaper. Andrew confirms it's cheap and going well, but caps out around a $1–2M/year labor-of-love business per city.
“So creating a newsletter, you know, I live in Lafayette, a city in California, and creating a newsletter for Lafayette, people living in Lafayette about Lafayette that just has kind of like one or two writers and you're basically replacing the local newspaper through newsletters. I love this idea.”
Steal thisLaunch a one-or-two-writer newsletter covering a single city and become the de facto local newspaper.
Idea
Own the daily newsletter for every town — a mini Murdoch empire
Shaan builds on Andrew Wilkinson's idea: a local news newsletter for a town, run by 2-3 writers, monetized via local classifieds and B2B advertising, with subscribers acquired cheaply through geo-targeted Facebook and search ads. Owning the daily newsletter for many towns could be a very big business.
“And like, can you build like, you know, a little version of Rupert Murdoch's empire? By owning the daily newsletter for every single town. That to me sounded like that wasn't just one of Andrew's kind of pet ideas. That to me sounded like potentially a very big idea.”
Steal thisLaunch a local-news newsletter for one town with 2-3 writers, monetize via local classifieds and B2B ads, then replicate the playbook town by town.
Number
Ferrari Market Letter: $2M revenue from 5,000 subscribers
The Ferrari Market Letter does $2 million in revenue from only 5,000 email subscribers with a team of just two people, illustrating the economics of a passionate niche audience.
$2M
Annual revenue · USD/year
“the Ferrari Market Letter has 5,000 email subscribers and does $2 million in revenue with a team of 2.”
Number
Ferrari Market Letter: $2M revenue from 5,000 subscribers
The Ferrari Market Letter does $2 million in revenue from only 5,000 email subscribers with a team of just two people, illustrating the economics of a passionate niche audience.
$2M
Annual revenue · USD/year
“the Ferrari Market Letter has 5,000 email subscribers and does $2 million in revenue with a team of 2.”
Fact
Three revenue streams of a niche enthusiast newsletter
Shaan breaks down the Ferrari Market Letter's economics: $600K-$900K from subscribers paying $100-$200 for content access, ~$1M from member-to-member classified ads, and the rest from advertising. The classifieds function as a built-in marketplace.
“They make $600,000 to $900,000 from 5,000 to 6,000 people who will pay about $100 to $200 for online or print access. And then they make another million dollars a year in annual member-to-member classified revenue, and then the remainder is from advertising.”
Steal thisStack three revenue layers on a niche audience: paid content access, member-to-member classifieds, and advertising.
Framework
Content, tools, advice: the audience-first ladder LearnVest climbed
LearnVest's plan never changed: start with free content to build an authentic brand and audience (a free newsletter in 2008), then add tools (a budgeting app), then advice. Each stage was an extension, not a pivot, with the company following its customers into what they wanted next.
“So we started, it was, the business plan was always the same. It was content, tools, and advice. And I started it out of my own savings. So we started with content because back in 2008 in New York City, I actually founded the company in 2007, you could do a free newsletter and just kind of get going. And so we started creating a brand, we started trying to talk to our users and just have a really authentic voice”
Steal thisBuild audience with free content first, then layer tools, then high-value advice as you learn what customers want.
Framework
Sell the story behind the product, take a cut
Shaan describes Huckberry and Goldbelly as businesses built on storytelling: find cool products, tell the origin story to a big email list (Huckberry has 1-2M men), and take a cut of revenue. The narrative, not the product spec, drives the sale.
“So what the, the business of Huckberry, it's basically a huge email list of 1 to 2 million guys. And what they do is they find really cool clothes and they, um, tell the story behind it. So for example, they had a duffel bag that was made from a, uh, the founder was an army guy who used to skydive., and the duffel bags were made out of old parachutes because apparently that's like an interesting material. And they told a story about this and they just blasted out in the email and they just take a cut of the revenue.”
Steal thisBuild an email list around the best-of-X products and sell the origin story, not the spec sheet.
Number
Userbase hit $826M market cap on just $5M raised
Sam explains that Japanese news aggregator Userbase reached an $826 million market cap before COVID despite raising only $5 million over roughly 10 years, an unusually capital-efficient outcome.
“Userbase is before the corona thing happened, they were publicly traded at $826 million market cap and they only raised $5 million to start and they're about 10 years old. So they raised a significantly, a very small amount of money for how big they got.”
Number
NewsPicks: 150K subscribers, ~$50M revenue
Sam points to Japan's NewsPicks as proof that paid news aggregation can monetize far better than free Western apps: it does roughly $50 million in revenue off only 150,000 subscribers.
$50M
Annual revenue · USD/year
“they only have 150,000 subscribers, but they do something like $50 million in revenue.”
Idea
Re-monetize Pocket/Flipboard: ~$100/user vs 50 cents
Sam pitches building a paid news aggregator for the US market, contrasting Japanese apps making ~$100 per user against free apps like Pocket and Flipboard that have 50 million users but make near-nothing per user.
“They have something like $50 million, or 50 million users. They don't make shit. They lose money, they don't make shit. And so what I wanna ask you is, why, how do you think you would monetize Flipboard and Pocket and these things better? Because we— like, now's the golden opportunity for new stuff.”
Steal thisTake a free content aggregator, repackage it as a paid subscription, and charge upfront.
Framework
Charging for free content makes people value it more (Trends NPS ~90)
Sam's playbook for paid information: repackage normally-free content as paid, charge upfront with no freemium, and pack pages densely with info. He cites Trends' NPS of ~90 (versus the free Hustle) as evidence people enjoy content more when they pay for it.
“And so what I've seen with our NPS for Trends versus The Hustle, which is free, the Trends NPS is significantly higher. It's like fucking 90, which is crazy high. And I believe that the content is great, but also people enjoy it more because they pay for it. So I think people, builders out there need to think to themselves, man, there's this weird mindfuck that I can just literally charge for something that normally is free and people will like it more. The second thing is I think people need to charge upfront, no freemium.”
Steal thisCharge upfront with no freemium tier; the price itself raises perceived value.
Number
Drudge Report: ~5-person staff could make $50M/year
Sam marvels that the Drudge Report, a 1996-era aggregator with a tiny staff, pulls roughly a billion views a month and could be run by about 5 people while making $50 million a year.
$50M
Potential annual revenue · USD/year
“This website is like the Craigslist of, of, of news. Like it's a tiny ass staff. It literally could be 5 people and it could make $50 million a year.”
Idea
A 'Netflix for mid-tier comedians' subscription
Shaan pitches a $5-7/month all-you-can-eat subscription aggregating comedians one tier below those who get Netflix specials. Each has a few thousand fans who'd pay for exclusive 10-20 minute sets, and aggregation lets viewers discover new comics.
“I think you could make a sort of $5 a month, $7 a month subscription to, uh, the, the comedians that are not going to get Netflix specials, right? So not Chris Rock and not Seinfeld and Chappelle and, and all those guys, but like the next tier down”
Steal thisAggregate mid-tier creators below the top platform deals into one cheap all-you-can-eat subscription that doubles as a discovery engine.
Number
Quello: 70,000 paying subscribers for a library of live concerts
Sam points to Quello, a 2010 app streaming live concerts at ~$10/month, as a viable niche-subscription model. It reached 70,000 paying subscribers and was acquired by publicly traded Stingray Communications.
“And they have 70,000 paying subscribers. They were recently acquired by Stingray Communications, which is a publicly traded company in Canada.”
Idea
Newsletters are New Zealand businesses you can build an empire on
Wilkinson tells Sam that newsletters are an incredible 'New Zealand business' and that owning The Hustle is like owning the modern newspaper. He frames the podcast's affiliation with The Hustle as proof you can stack many businesses on top of a self-sufficient audience asset.
“One of the things I was gonna say is I think newsletters are an incredible business. They're New Zealand businesses, right? Like I think Sam, you own the modern newspaper essentially, and I think that you're gonna be able to unlock so many businesses.”
Steal thisTreat your newsletter as the self-sufficient core asset and stack new businesses (job boards, products, media) on top of its audience.
Story
17-year-old turns $800 of car-mod parts into $1M e-commerce store
Furqan Rydhan, bored after a dot-com flameout, noticed PC enthusiasts wanted to 'trick out' their computers but had nowhere to buy parts in the US. He bootstrapped an accidental e-commerce store from $800 of inventory in his garage corner and hit $1M revenue in year one, at age 17.
“So I started an e-commerce store kind of accidentally. I was like, oh, like, these things are really expensive. If I buy them in bulk, I just get them cheaper. I'll sell off some, I'll have some more cash on the side. And I think we started, uh, $800 of stuff in the corner of my garage, and then within the first year we did $1 million of revenue.”
Steal thisFind a passionate niche community that has no good place to buy the gear it loves, then become that store.
Number
The Hustle: 8-figure revenue, fat margins, targeting $100M by 2025
Sam reveals The Hustle is highly profitable with 8-figure revenue and fat margins, no venture capital taken. He sets a goal of $100M revenue by 2025 and estimates a company like his could sell for $20M-$60M.
$100M
Revenue goal by 2025 · USD/year
“So our business is very profitable. It makes 8 figures in revenue, really fat margins. My goal is to get it to $100 million in revenue by 2025, and I think we'll get there. So it potentially may not be Uber, but it'll be a nice-sized business. It'll be a $100 million business. Companies like ours could probably sell for any— in the huge number, the huge range of $20 to $60 million. And we haven't taken any venture capital.”
Number
BizNow sold for $60M cash on $20M revenue, $7M profit
At the time of sale, BizNow was doing roughly $20M in revenue and $7M in profit, and sold for $60M in cash — all bootstrapped.
$60M
Acquisition price · USD
“And he grew it and eventually sold it for $60 million in cash. And at the time of the sale, it was doing like $20 million in revenue, $7 million in profit.”
Number
BizNow sold for $60M cash on $20M revenue, $7M profit
At the time of sale, BizNow was doing roughly $20M in revenue and $7M in profit, and sold for $60M in cash — all bootstrapped.
$60M
Acquisition price · USD
“And he grew it and eventually sold it for $60 million in cash. And at the time of the sale, it was doing like $20 million in revenue, $7 million in profit.”
Number
Comcast bought DailyCandy newsletter for $400M
Ali cites DailyCandy, a newsletter for women, as inspiration for chasing the newsletter business — Comcast acquired it for $400 million.
$400M
Acquisition price · USD
“There's a company called Daily Candy, which was a newsletter for women that Comcast bought for $400 million.”
Story
Daily Candy, Thrillist, Groupon: billion-dollar companies that started as email lists
Sam relaunched The Hustle as an all-email business in 2016 after studying Groupon, Daily Candy, and Thrillist. The insight: build a huge email list as a distribution channel, then layer products on top.
“if you study the history of Groupon, of, um, Daily Candy, of Thrillist, people may not even know what the last two are, but anyway, I was like, man, some of these like billion-dollar companies all started with an email list. Like, let's do that. Let's build up this huge email list and then start creating more products and use that as a distribution channel. And I think we could build a billion-dollar company that way.”
Steal thisBuild an email list as your owned distribution channel first, then launch products into it.