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Deep Dive with Ali Abdaal

Lessons From Selling Morning Brew For $75 Million At 28 - Alex Lieberman

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Alex LiebermanguestAli Abdaalhost

Jul 14, 20221h 40mWatch on YouTube

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CHAPTERS

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Chapter summaries

Losing his dad and seeing life as a finite “countdown clock”
Alex opens with the sudden death of his father and explains how it reshaped his priorities. He describes the clarity it brought: many daily worries are unimportant, and time is unpredictable and finite.
- •His dad died suddenly from a stroke at age 49, shortly before Alex’s junior year of college
- •The experience reframed what matters day-to-day versus what feels urgent but isn’t
- •He started asking what he’d do differently if he knew his “countdown clock” hit zero tomorrow
- •This framing later influenced major career decisions
From a Wall Street family to Michigan: the path he assumed he’d take
Alex recounts growing up in a finance family where working on Wall Street felt like the only viable future. He contrasts his small private-school background with his choice to attend the University of Michigan and pursue business.
- •Everyone in his family worked in sales and trading, shaping his early career expectations
- •He chose Michigan to get a different social and college experience than his small high school
- •He followed the finance pipeline: internships leading toward a Wall Street role
- •By senior year, he already had a job offer and a light course load
Market Corner: starting an email newsletter as a personal “tinkering” project
Alex explains how helping students prep for interviews revealed a problem: business news felt dense and joyless to his peers. He started writing a daily business roundup—originally called Market Corner—primarily to keep himself sharp and to help others.
- •Mock interviews revealed students read business news out of obligation, not interest
- •He didn’t initially view it as a business; he viewed himself as a “tinkerer”
- •Writing forced him to distill information and stay on top of business news
- •He launched the first newsletter in October 2014, beginning the Morning Brew journey
How he used senior-year freedom: experiments, campus life, and a standout real estate class
With few academic obligations and no job recruiting, Alex had abundant time and used it for the newsletter, games, and exploring Michigan life. He also describes a hands-on, interdisciplinary real estate development class that felt closer to real work.
- •He had only three classes in senior year and no recruiting obligations
- •He spent several hours daily on the newsletter alongside leisure and campus activities
- •He TA’d and describes an interdisciplinary real estate class simulating real development work
- •The class combined business, architecture, law, and urban planning roles in one project
Why academia feels broken—and the two “useful” classes (Excel and typing as timeless skills)
Alex argues most academic learning didn’t translate to his career, criticizing universities for teaching what to think instead of how to think. He highlights Excel proficiency (and earlier typing skills) as unusually durable, practical advantages.
- •He says academia is broken: too much focus on what to think versus how to think
- •He wishes more entrepreneurs and practitioners taught at universities
- •Excel class helped with pivot tables, shortcuts, and Visual Basic; he still uses Excel
- •He calls typing the most valuable class he ever took due to daily compounding utility
Storytelling and selling as the core meta-skill (and how to improve it)
Alex frames selling as essential for founders and professionals, especially when raising money, hiring early employees, and landing advertisers. He connects “selling” to storytelling and outlines how people can improve through fundamentals, practice, and feedback loops.
- •He says selling is a top skill that powered Morning Brew’s early growth
- •He links selling to storytelling, arguing that “selling” is often just poor storytelling
- •He describes needing to sell investors, early employees, and advertisers with minimal traction
- •He explains improvement through understanding story formulas, repeated reps, reflection, and recorded feedback
Building the early Morning Brew product: student writers, an editor, and a “voice editor”
When Morning Brew became a more formal newsletter, Alex and Austin focused on making it excellent and growing quickly. He describes a volunteer “newsroom” of student writers, a dedicated editor, and a recruited humor-focused voice editor to create the signature tone.
- •They recruited student readers to write stories and build a rotating writer group
- •Writers were unpaid and participated for exposure and belief in the project
- •They added an editor with experience in markets and student journalism
- •They hired a “funny person” from an improv background as a voice editor to shape the conversational tone
Analog growth that worked: hub-and-spoke pitches, paper sign-ups, and ambassador program iterations
Alex details their early distribution strategy: target “hubs” like teachers and club presidents rather than individual students. They pitched in classes and club meetings, used paper sign-up sheets for higher conversion, and scaled via a college ambassador program—after learning from a first failed attempt.
- •They used a hub-and-spoke model: reach hubs to access many potential readers at once
- •They pitched in ~150 classes/club meetings and passed around paper sign-up sheets
- •Paper sign-ups converted better than asking students to visit a website in real time
- •Their first ambassador program failed due to selecting overly busy high-achievers; the second scaled by automating onboarding and requiring performance before direct interaction
Working at Morgan Stanley while building Morning Brew—and the decision framework to quit
After graduating with about 10,000 subscribers, Alex chose to take his finance job while working nights on the newsletter. He explains the inflection point when Austin faced a similar fork, and how Alex used regret-minimization and worst-case-scenario thinking to decide to go all-in.
- •He worked early-to-late at Morgan Stanley, then worked on Morning Brew at night
- •He did this for just over a year, quitting after Labor Day 2016
- •Austin’s upcoming investment banking path forced a fork: go full-time or let the project stall
- •Alex chose based on anticipated regret and layered worst-case planning about what would happen if it failed
Grief, emotional suppression, and learning to “fully feel” through therapy
Alex returns to his father’s death and describes how he learned he was skilled at suppressing feelings—useful during crises, but costly personally. He shares therapy practices centered on visualization, sitting with emotions, and how he evaluated and switched therapists based on evolving needs.
- •He describes calling his dad’s old number over the years as a way to reconnect with the loss
- •He realized he tended to bury emotions and cried only once after the death, which created guilt
- •He reframed the goal from “feel more” to “fully feel my feelings”
- •He explains therapy tools: guided visualization of formative moments, sitting with emotions for 30 seconds, and changing therapists when progress plateaued
Hustle, balance, and the two types of procrastination that erode self-belief
In discussing hustle culture, Alex says Morning Brew likely wouldn’t have been as successful with less effort—though he adds that efficiency and less procrastination could have created more balance. He breaks procrastination into avoiding work via non-work and avoiding the important work by doing “the wrong work,” describing the resulting “procrastination hangover.”
- •He says the business likely needed intense effort early on, with a caveat about efficiency
- •He defines two procrastination types: non-work avoidance (social media) and wrong-work avoidance
- •He describes addiction to validation and dopamine from platforms as it worsened over time
- •He explains how procrastination creates a “hangover” feeling and reduces trust and self-belief
Self-worth, metrics anxiety, and affirmations as a response to external validation loops
Ali shares how writing triggered self-doubt because he compared first drafts to others’ finished work, and how lowering standards helped him write consistently. They compare content metrics anxiety (views, likes) with identity and money fears, and Ali reads a set of affirmations he uses to counter spirals.
- •Ali describes writing momentum by allowing placeholders and returning later
- •Ali links procrastination to self-doubt and unrealistic standards; he learned to embrace bad first drafts
- •Alex asks about Ali’s relationship with checking views/subscribers; Ali describes the emotional volatility
- •Ali shares affirmations focused on having “enough,” self-trust, and rebuilding if everything were lost
- •Alex connects the “rebuild” affirmation to his own money-hoarding and fear of having already peaked
Selling Morning Brew: the partnership-to-acquisition path and the anticlimax of the wire
Alex explains how the acquisition began through a relationship with a Business Insider leader after earlier syndication outreach. He recounts naming a price that made the conversation worthwhile, using a banker to manage negotiations, the pandemic’s impact on deal timing, and feeling surprisingly numb when the money finally wired.
- •The deal closed in October 2020 with Business Insider’s parent company, Axel Springer
- •Initial connection came from Alex pushing for newsletter syndication and building a relationship
- •He proposed $50 million as a ‘stupid amount of money’ worth discussing; talks progressed
- •A banker handled negotiation intermediating and the data room; the pandemic temporarily crushed advertising and slowed the deal
- •On the final wiring call, he felt nothing, and says his lifestyle spending didn’t fundamentally change
After the exit: identity loss, motivation without money, and searching for a new North Star
Alex says he wasn’t happier after the acquisition and for a time felt less happy because money stopped functioning as a motivator. He describes stepping from CEO to executive chairman, grappling with identity, and exploring what might come next—while acknowledging he’s still in process.
- •He says money could no longer be a motivator or ‘crutch’ after the sale
- •He moved into the executive chairman role in April 2021 and felt identity drift as work hours decreased
- •Ali describes purpose as the ‘baby you have to feed’ and his own “ideal ordinary week” model
- •Alex lists possible directions: building businesses, helping entrepreneurs, becoming a therapist or executive coach
- •He’s experimenting via angel investing, coaching, and focusing more on health basics like food and sleep

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