Jan 3, 2023 · 59m · founders-journal
Co-founders Austin Rief and Alex Lieberman on Building Morning Brew
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this retrospective episode of The Crazy Ones, Morning Brew co-founders Alex Lieberman and Austin Rief join moderator Sahil Bloom for an unfiltered discussion on founding, scaling, and selling their media company. They detail grassroots audience acquisition, editorial voice development, executive leadership hand-offs, and the psychological impact of their multimillion-dollar exit.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 50.4% of the talking time here. How this is scored →
Alex as informed peer 7.5 Guest teaching 1.6 Guest disagreement 1.5 Alex pushing back 1.4
speaking balance: gold is Alex, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 39:34 Calling out founders for ignoring past DMs
Sahil jokingly confronts both co-founders on air for completely ignoring his early Twitter DMs back when he had very few followers.
Hardest push from Alex ▶ 4:16 Challenging hindsight fuel narrativeSahil pushes back on the claim that investor rejection emails served as motivational fuel rather than just a discouraging blow at the time.
Biggest teaching moment ▶ 44:30 Compounding executive hiring mismatchAustin educates listeners on how hiring senior executives who lack the capability to scale quickly creates cascading middle-management bloat across fast-growing companies.
Alex holds their own ▶ 34:00 Hub and spoke audience acquisition strategyAlex explains in precise detail the hub-and-spoke growth architecture they developed to turn active readers and students into high-leverage referral nodes.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Alex as informed peer | Guest teaching | Guest disagreement | Alex pushing back | Why |
|---|---|---|---|---|---|---|
| Early Rejections, Doubters, and Founding Motivations | 7 | 1 | 2 | 2 | Alex and Austin reflect openly on early rejections and founding doubts. Alex explains his internal mindset and vulnerability regarding his father's passing, while Sahil lightly probes on whether the 'fuel' narrative is hindsight revisionism. | |
| Upbringings and Wall Street Career Expectations | 6 | 1 | 1 | 1 | Alex and Austin share their contrasting backgrounds and expectations of corporate careers versus entrepreneurial instincts. The tone is highly collaborative and reflective. | |
| Market Corner Origins and Initial Partnership | 7 | 2 | 2 | 2 | Austin and Alex banter playfully about college habits, fraternity rush stories, and the crude early design of Market Corner. Austin candidly critiques the original newsletter quality. | |
| Side-Project Advantage and Newsletter Unit Economics | 8 | 2 | 1 | 1 | Alex and Austin break down the straightforward unit economics of newsletters and how starting without business pressure allowed long-term compounding decisions. | |
| Scrappy Growth Tactics and the Ambassador Program | 9 | 1 | 1 | 1 | Austin and Alex detail the gritty 0-to-1 subscriber acquisition tactics, from pitch lecture halls with printed Excel sheets to cross-promotions and college ambassador programs. | |
| Defining, Training, and Scaling Editorial Voice | 8 | 2 | 2 | 1 | Austin and Alex explain how they codified voice into rubric personas and interview prompts, sharing colorful anecdotes about hiring key managing editor Neil. | |
| Hiring Lessons, Scaling Pains, and the CEO Hand-off | 8 | 3 | 2 | 2 | Austin outlines how organizational hiring mistakes compound when companies scale too fast, while Alex details his vulnerability in stepping down from CEO to Chairman. | |
| Financial Exit to Business Insider and Wealth Impact | 7 | 1 | 1 | 1 | Both founders share candid reflections on financial liquidity from the Business Insider acquisition, discussing money anxiety, changed risk profiles, and freedom of time. |
Statements from this episode (14)
Lieberman: Mark Cuban passed on Morning Brew over differentiation questions
“I remember Mark Cuban, we also asked him to invest, and I give so much props to Mark, because he is someone that, irrespective of his success, he still,
Emails with founders at the earliest stages all the time, but basically he had a similar response to this t…”
Lieberman: The first Market Corner email went to 45-50 people
“The first email went out to like, 45 or 50 people. And it started with like, AEPI people, people in the business school, and my family.”
Rief: High-utility products succeed despite terrible visual design
“It was the classic thing where product sucks but people still use it. Like, oh, I mean, it's like Amazon. Amazon looks terrible. It's the worst design site that I use, yet people, people use it.”
Rief: Morning Brew would have failed if started intentionally as a business
“We didn't intend for it to be a business. And if we did, and we thought about it as a business in 2015, I think it would have failed. We would have made long, short term decisions to make a little money here or there, but because of the side project, we didn't…”
Rief: Media products grow best when promoted within the same medium
“There are people who are just newsletter people, just like when you want to promote a podcast, you do it on other podcasts. Like mediums promote like mediums.”
Lieberman: Hyper-involved campus leaders make poor brand ambassadors
“So the first time we did it, we had 10 ambassadors. We were super stringent. We went through resumes. We had an interview process, and we're like, we're gonna pick the most impressive people on college campuses who's, like, The student body president in like f…”
Lieberman: Morning Brew Did Not Hire Any Trained Journalists Early On
“In the early days I would say none of our hires were journalists, and we've hired a more, ah, let's call it like traditional, ah, journalist journalistically trained writers over time, as we've gotten a sense of, kind of, what we're looking for, but in the ear…”
Lieberman: Short News Summaries Are the Best Hiring Test for Writers
“And to this day, A very simple prompt, writing prompt, is like the best proxy for someone getting hired at the brew. You take a big business news story from the last few days, in a 150 to 250 words, you summarize this story in a way that connects with the audi…”
Lieberman: Morning Brew Scaled Its Voice Using a Detailed Persona One-Pager
“We had a one-pager that defined the Morning Brew voice as a person. So it would literally be like, Our voice is Sahil. He is thirty-something years old, living outside in New York City. He will drink once or twice a week. His preferred drink is whiskey. Other …”
Rief: Outgrown executives cause worse organizational bloat than outright bad hires
“There's two types of mishiring, and I think people usually think about the first that I'll give you, but it's the second that really kills you. The first is you just mess up. You hire a senior exec, you know within four to six months of the wrong person hopefu…”
Lieberman: Staying in the CEO role too long was his biggest mistake
“I think the biggest mistake was probably actually staying in the CEO role too long.”
Rief: The study claiming happiness caps at a $70k salary is wrong
“I think there's like that whole 70,000 dollar salary you know, study that people are happier at 70,000 dollars. I don't think that's true. I think I am happier”
Lieberman: Happiness plummeted after selling Morning Brew and stepping down as CEO
“Deal was October of twenty-twenty. Moved out of the role in April of twenty-twenty-one. My happiness actually went down a lot.”
Bloom: Highly successful and wealthy people share an intense paranoia of going broke
“There's this weird paranoia that a lot of really successful people have about losing it all. Like, they think they're gonna end up totally broke, which is almost impossible if you, unless you royally screw something up.”