Sam's pet business idea: a quarterly physical magazine or zine for a specific industry (financial advisors, ad world) built to name as many people and companies as possible — a printed status object companies pay an annual fee to appear in, like a 30-under-30. Print signals legitimacy the way Casper subway ads feel more legit than Facebook ones; he points to Arena magazine as a beautiful example.

A quarterly print magazine or zine for a tight industry.
The engine: name as many people and companies as possible.
Firms pay annually just to have their name on paper.
Print signals legitimacy that digital ads don't; see Arena magazine.

“The whole name of the game would be name as many names as possible... just to have their name on paper.”
Sam Parr · 1:04:30

#opportunity#print-media#status

Story· 3

Story11:30

When 'We Want to Buy You' Became a Job Interview

Both founders were approached by media heavyweights — John Steinberg (ex-BuzzFeed) for Morning Brew, Ben Lerer (Thrillist) for The Hustle — expecting an investment or acquisition, only to have the meeting flipped into a recruiting interview. Steinberg's line: 'the legal fees to do this deal would be more than what I'd pay for you guys.' Their irrational confidence in declining preserved all the upside.

Steinberg and Lerer both turned buy/invest talks into job interviews.
Lerer told Sam a newsletter would 'never make more than $2 million a year.'
Declining took conviction — joining would have capped their upside.
The rejections became lasting chips on their shoulders.

“The cost of the legal fees to do this deal would be more than what I would pay for you guys.”
Alex Lieberman · 13:30

#fundraising#conviction#media

Story44:30

From COVID Near-Death to a Boom Year

When COVID hit, ~30% of booked revenue vanished in weeks and a $75k sponsorship was cancelled overnight. They cut paid marketing to zero and brainstormed everything from Patreon donations to an education product — Morning Brew's paid course with Scott Galloway's Section4; The Hustle's course made $300k in a month. The first half of 2020 felt terminal; the second half boomed.

~30% of booked revenue vanished in weeks as COVID hit.
First lever pulled: paid marketing to zero.
Education products were launched for emergency short-term cash.
The Hustle's course made $300k in one month; H2 2020 boomed.

“In a period of a few weeks, 30% of all revenue that we had booked vanished.”
Alex Lieberman · 44:30

#covid#resilience#pivot#cash

Story52:00

The SoFi Pitch and the Incentive Trap

Pitching Morning Brew to SoFi over Zoom, a executive deadpanned 'I don't get it,' and the head of business development flashed SoFi Stadium: '300 million eyeballs a year — what are we going to do with 3 million emails?' The deeper lesson: pitching 'we can market your product better than you' to a marketing team triggers their fear, so they won't buy.

SoFi rejected the pitch, citing stadium reach over email reach.
Selling 'we market better than you' to a CMO triggers self-preservation.
Acquirers buy for their own incentives, not your logic.
HubSpot bought The Hustle for users, not its extra profit.

“You think we want 3 million emails? He shows their big stadium: 300 million eyeballs a year.”
Austin Rief · 52:30

#m&a#incentives#pitching

Tool· 2

Tool21:00

Hire Undiscovered Talent, Not Media Veterans

Traditional media pros laughed off both companies ('that's cute, thank you'). So they hired non-traditional writers — a procurement-startup blogger, unknowns like Neil Freyman and Lindsey Quinn — and sold them on the dream of doing their hobby full-time. Seeing a ceiling in people others overlooked became a hiring superpower.

Established media talent rejected them; they couldn't afford it anyway.
They hired writers who could write but weren't 'writers' by title.
The pitch was 'do this hobby all the time and make money from it.'
Spotting overlooked ceilings was a shared edge of Brew and Hustle.

“Morning Brew and Hustle were really good at finding undiscovered talent and seeing a ceiling in them that other people didn't realize.”
Alex Lieberman · 21:30

#hiring#talent#team

Tool35:30

Adopting EOS / Traction at the $5-10M Mark

An investor (the Snuggie's creator) pushed Austin toward the book Traction and its Entrepreneurs Operating System. It became a game-changer and the inflection point where Austin effectively became CEO. All three hosts hit it around the $5-10M revenue mark; Sam's regret was not hiring a ~$60k/year implementer because he didn't want to be 'the bully.'

Traction/EOS is a framework for running a scaling company.
It became Morning Brew's operational inflection point.
Sweet spot to adopt is roughly $5-10M revenue.
An EOS implementer (~$60k/yr) is an executive-coach-slash-organizer.

“Once you get to like the five to ten million mark, that's where it's like... how do I do more of it without killing myself.…”
Sam Parr · 37:30

#operations#eos#scaling#systems

Takeaway· 3

Takeaway18:30

The One-Year Plan That Took Nine Years

Alex recalls a slide in their investor deck showing a one-year plan. Looking back, it took nine years to try everything on it — and most of those things didn't work. The lesson: in startups you always overestimate how much you can accomplish in a short window.

Their investor-deck 'one-year plan' actually took nine years.
Most of the planned initiatives ultimately failed.
Founders chronically overestimate short-term progress.
Time behaves strangely in startups.

“That slide, looking back on it now, took us nine years. We tried everything in that slide, and it took us nine years.”
Alex Lieberman · 19:00

#planning#startups#expectations

Takeaway33:30

Go Niche for Higher CPMs and Direct Monetization

Hitting the economic plateau of a single mass newsletter, Morning Brew moved into industry verticals (retail, marketing, finance/CFO). Niche audiences command higher CPMs, don't require a race-to-the-bottom growth war, and make direct monetization clearer. B2B has also held up better through the ad-spend pullback.

A single mass newsletter hits an economics ceiling (~$18/subscriber for Brew).
Vertical, niche audiences earn higher CPMs and need less growth.
Niche makes direct audience monetization more obvious.
B2B has been less impacted by the advertising pullback.

“The more niche you go, especially if you pick the right niches, not only can you get higher CPMs... the more clear it becomes how…”
Alex Lieberman · 57:00

#niche#monetization#b2b#cpm

Takeaway42:30

You Can Be Right Without Being an Asshole

During the brutal sale process, Austin took difficult-investor calls as 'a bull in a china shop.' His now-wife told him he was being an asshole; he protested 'but I'm right,' and she replied 'you're totally right, but you can be right and not be an asshole.' It was a genuine maturation moment about how correctness and delivery are separate.

Selling triggered difficult behavior from investors and employees.
Being right and being kind are independent variables.
The sale process was the founders' hardest maturation crucible.
When money is on the table, everyone reframes their contribution.

“You're totally right, but you can be right and not be an asshole.”
Austin Rief · 43:00

#maturity#communication#exit

Frameworks in this episode

IQ Arbitrage

Manufacture an Enemy

Monetize Within Your Content Core Competency

Organic First, Then Pay for Growth

Spend Into a Positive LTV:CAC

The Standard Is What You Allow

Insights & moments

◆Hot Take· 1

The Physical Magazine 'Name as Many Names' Play

❝Story· 3