Apr 4, 2025 · 1h 11m · my-first-million
How to build a $100M+ newsletter business
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
The Hustle founder Sam Parr and Morning Brew co-founders Alex Lieberman and Austin Rief provide an in-depth, year-by-year post-mortem of how they built, scaled, and sold their newsletter media companies for hundreds of millions of dollars. They discuss audience acquisition tactics, hiring non-traditional talent, operational frameworks, and critical strategic advice for launching digital media ventures today.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 40.6% of the talking time here. How this is scored →
The hosts as informed peer 6.2 Guest teaching 3.1 Guest disagreement 2.1 The hosts pushing back 2.1
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 29:55 Austin revealing intelligence gathering on Sam
Austin bluntly tells Sam that he gathered intel from former employees to exploit Sam's conservative profit thresholds and accelerate Morning Brew's aggressive paid acquisition.
Hardest push from the hosts ▶ 4:09 Sam calling out Morning Brew's origin narrativeSam interrupts Alex's polished founding story to assert the real genesis was simply replicating The Skimm model for finance audiences.
Biggest teaching moment ▶ 23:37 Alex and Austin on non-negotiable content standardsAlex explains how setting the standard meant ruthless line-by-line critiquing of drafts, leading Sam to admit his own earlier management approach was flawed.
The host holds their own ▶ 58:50 Sam dissecting media companies straying outside core competencySam demonstrates strong domain expertise by diagnosing why media startups almost universally fail when trying to pivot into software or ecommerce instead of doubling down on content and direct audience trust.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| Reflecting on Rivalry and Structuring the Retrospective | 6 | 2 | 2 | 2 | Sam establishes the retrospective structure and compares notes with Austin and Alex about their past rivalry and mutual admiration. The atmosphere is nostalgic and collaborative rather than combative. | |
| 2015 Origins: College Newsletters and HustleCon Scrappiness | 6 | 3 | 2 | 3 | Sam challenges the romanticized founding story of Morning Brew, suggesting they simply copied The Skimm model, which Austin and Alex partially concede while detailing their early spreadsheets and arbitrage over legacy media. | |
| Sponsor Break: Leveraging ChatGPT for Life Coaching | 5 | 3 | 2 | 2 | After an opening sponsor pitch, the trio recounts 2016 war stories including near-firings on Wall Street and insulting acquisition/job interview meetings with legacy media figures like John Steinberg and Ben Lerer. | |
| 2017: Non-Traditional Hires, Strict Standards, and Underdog Culture | 6 | 5 | 2 | 1 | Alex and Austin explain their intense editorial standard-setting process in 2017-2018, dissecting newsletters line-by-line. Sam openly admits he lacked that discipline at the time and praises their operational maturity. | |
| 2018: Aggressive Paid Acquisition and Differing Capital Philosophies | 6 | 4 | 3 | 2 | The founders compare their 2018 acquisition spending strategies. Austin reveals how he tracked The Hustle through backchannels and took advantage of Sam's profit-taking posture by reinvesting aggressively into paid ads. | |
| 2019: Operational Transformation, EOS Traction, and B2B Diversification | 7 | 3 | 2 | 2 | Both sides discuss adopting the EOS Traction framework in 2019 to shift from chaotic founder hustle to systematic management, trading best practices on implementers and launching B2B/paid offerings. | |
| 2020: Surviving the Pandemic and Finalizing Landmark Acquisitions | 7 | 3 | 2 | 3 | Sam, Alex, and Austin recount navigating the COVID-19 advertising shock and executing high-stakes sales to HubSpot and Axel Springer, including pushback on why buyers valued audience integration. | |
| Navigating Today's Media Landscape: Pitfalls, Niche Verticals, and Big Swings | 8 | 4 | 3 | 3 | The conversation shifts to actionable advice for today's market. Sam and the guests drill into physical print, hyper-niche B2B verticals, and the danger of media companies trying to build non-media software products. | |
| Wrapping Up: Embracing Competitive Enemies and Lasting Friendship | 5 | 1 | 1 | 1 | The hosts wrap up the episode discussing the psychological utility of manufacturing competitive rivalries to fuel startup growth before closing on their genuine close friendship. |
Statements from this episode (27)
Morning Brew's publicly reported acquisition price was $75 million
“Seventy-five million, I think is the public number.”
HustleCon generated $400K in revenue and $200K in profit in 2015
“So in 2015, I think I was 25. It wasn't the hustle. It was just an event called HustleCon. And that year, I think it had made around 400,000 dollars in revenue and like 200,000 dollars in profit.”
BuzzFeed's media business model was never worth a $1B valuation
“And, you know, even in 2015, 20 17, we were like, yeah, PuzzFeed, it just doesn't make sense. It's not worth a billion dollars.”
The Hustle generated $400K in revenue in its 2016 launch year
“The hustle launched on four, 2016. And so that year we did 400 K in revenue. I think we had at the end of the year, we had like a 100,000 subscribers.”
Morning Brew's first ad deal was $3,000 for three exposures
“In 2016, we did our first ad deal. It was a watch brand called Emla Hart, I believe. It was about a 3000 dollar deal for three, we used to call them exposures.”
Newsletter and digital media founders today should avoid raising external funding
“So if you're listening to this, I, if I were starting today, I would not raise funding at all.”
Morning Brew's seed round comprised 28 angel checks from $2,500 to $100K
“The first is we had 28 individual investors. So we had 28 people who wrote checks from 2500 dollars to a 100,000 dollars.”
The Hustle ended 2017 with 250K subscribers and $2.2M in revenue
“We ended the year with 250,000 subscribers. We had 2.2 million in revenue. 400 K was events. 1.8 was advertising.”
Morning Brew reached 100K subscribers and $300K in revenue in 2017
“We ended at a 100,000 subs. We did 300,000 dollars of revenue. We finally started taking a salary. We were taking 60 K each, but that was the first real year.”
The operational standard of a business is simply what its leaders allow
“The standard of your business is what you allow. And so like, if you allow suboptimal content to be written, that is the new standard you set. Like basically you're implicit by saying, not saying anything to something you're implicitly saying that that is okay…”
The Hustle generated $5.1M in revenue and $160K profit in 2018
“So in 2018, I think we ended the year at 500,000 subscribers. We had 5.1 million in revenue. About a million was from advance. And I paid my we had a 160 grand in profit.”
Morning Brew was spending $500K per month on ads by late 2018
“If I remember, by the end of that year, we were spending like, 500 K a month on ads, right?”
The Hustle generated $8M in revenue and $1.6M cash flow in 2019
“We did about eight million in revenue, which would six 40 being from events. We did profit of 200,000, but we did cash flow of 1.6 million.”
Morning Brew reinvested $6M to $7M into paid acquisition in 2019
“And we were spending this year, we probably spent six to seven million dollars on paid acquisition. So we spent what you did in revenue almost just pumping growth back in.”
Morning Brew's biggest regret was failing to hire an EOS implementer
“And that's my biggest regret is not hiring a, an implementer because I didn't want to be the bad guy. I didn't want to be the bully.”
Morning Brew lost 30% of its booked revenue when COVID-19 hit
“And I can't remember the exact amount, but let's just call it like in a period of a few weeks. 30% of all revenue that we had booked vanished.”
The Hustle's 2020 educational course generated $300K in a single month
“We did an education like a course, and it made 300,000 dollars in one month, and it helped save us”
Vice Media attempted to acquire The Hustle in an all-stock deal
“So the first time I tried to sell, I hired a banker and we ended up getting an offer from vice and it was an all stock offer.”
Pitching acquisitions to CMOs fails because it threatens their marketing competence
“Yeah, I mean, at the end of the day, we were telling the marketing team of a company, we can market your product better than you can. You know, what CMO, what head of marketing is going to buy a company, unless they have a ton of humility, if they believe that…”
Morning Brew generated $70M in revenue and $10M profit in 2022
“So 21, you did forty-six million in revenue and ten million in profit. 22, Seventy million in revenue, ten million in profit. 23 was the same numbers”
Sam Parr passed on investing in beehiiv because he thought it silly
“I chose not to invest in Beehive.
I thought that was a silly idea.
I was wrong about both of those things.”
Newsletter subscribers are worth significantly less today due to market saturation
“The value of a subscriber is significantly less than it was when we started because there are so many newsletters out there.”
Media companies that attempt to sell software to their audiences will fail
“That strategy that they and many other people who are, or I don't even know if they did do it, but whoever wants to try and do that, it will almost always fail.
Because in order to make a business like this work,
Where you sell stuff to your audience.
You almo…”
Media brands dominating alternative asset investing will generate massive financial returns
“Alternative investments are becoming a bigger part of people's portfolios, but they're more opaque.
They're harder to understand, but they're also really interesting ways to monetize people who are investing in alternatives.
I think basically a company that be…”
James Altucher publicly claimed his premium newsletter generates $120M in annual revenue
“He said he made a hundred, he said it on stage.
He said a hundred and twenty million dollars a year in revenue.”
Startups need an enemy: Morning Brew used TheSkimm and The Hustle
“And I think having an enemy, whether it's real or fake, right for us, it was the skin and the hustle. I think it's really, really important. You know, beehive has convert kit. And I think it just motivates everyone just a little bit more.”