Alex Lieberman on stoicism, money, and curating wisdom

Executive overview

Selling a company for $75 million didn't fix Alex Lieberman's anxiety. Stepping back from the Morning Brew CEO role left him directionless, stuck in circular thinking about whether success was luck and whether money would ever feel like enough. Stoicism gave him a framework to separate what actually happens from the story he tells himself about it.

The core insight: your perception of events — not the events themselves — is where unhappiness lives, and that perception is within your control.

Discovering stoicism — and overcoming the misconception

• Alex assumed "stoicism" meant emotional suppression — the opposite of what he wanted
• A gifted copy of The Beginner's Guide to Stoicism broke that story: "Tools for Emotional Resilience and Positivity" didn't fit his narrative
• Ryan's The Obstacle Is the Way deliberately omits "stoicism" from the cover for the same reason — every reader has a limiting story to overcome
• Morning Brew's subject-line testing is the same principle: you're not just representing your product, you're anticipating objections before they form

Money, meaning, and the circular reference

• After the sale, Alex expected money anxiety to disappear; it didn't — his anxiety level stayed constant
• The $70k happiness research rang true only after he lived through having far more
• His actual definition of a good life: family, two homes, vacations, no money anxiety — none of which required tens of millions
• The Stoics (Marcus, Seneca, Cato) were wealthy and still concluded wealth is "preferred indifferent" — better to have than not, but not where wellbeing lives

Losing the CEO role and finding direction

• Moving from CEO to executive chairman meant freedom of time with no clear identity
• The fear: "I don't want to be the 28-year-old who peaked at 28"
• Stoicism bridged Western therapy (labeling, prescribing) and mindfulness (high-level, abstract) with specificity and practicality
• Goal of inner work: unlearn the expectations, anxieties, and regrets the world installed — "living like a child again"

Controlling what you can control in management

• Anticipatory anxiety is the dominant failure mode for managers: worrying about how someone will react, not how to deliver feedback clearly
• Alex's default as a first-time manager: avoid the hard conversation to dodge a reaction he couldn't control
• The reframe: your job is to deliver feedback with clarity and empathy — how someone responds is not yours to own
• Stoicism fits entrepreneurship because things never go as planned; the leader's role is to improvise and adapt without dumping emotion on the team

Emotions and leadership

• Seneca's essay on anger: the higher your position, the less you can afford to act on raw emotion — too much depends on you
• The first flash of feeling is involuntary and acceptable; what you do next is the choice
• Alex's coping pattern — going numb to crises — had a cost: processing emotions as a robot, not as a person
• Mindfulness framing: thoughts are clouds, you acknowledge them without grabbing hold; ACT therapy uses the same mechanism

Uncertainty and the power of having no opinion

• Recording during early Omicron: a two-week period of genuine unknowing is one of the hardest things to ask of people
• Common responses — doom scrolling, blame, denial — change nothing about the underlying uncertainty
• Marcus Aurelius: you always have the power of having no opinion; it's a power we relinquish constantly
• On the pandemic more broadly: some percentage of people will always be selfish, misinformed, or misled — expecting otherwise was naive

Twitter, social comparison, and mental health

• Alex's problem with Twitter isn't doom scrolling — it's procrastination and broken self-promises
• The pull to check likes and retweets is the exact validation loop he doesn't want to reinforce
• Concentration of VCs and unicorn founders on Twitter triggers social comparison and a feeling of inadequacy
• Ryan treats Twitter as a one-way publishing medium; the cost is losing organic DM connections, which is how they met
• Instagram has most of the upside with less of the "radicalization" aftertaste

Media diet and curation over creation

• Alex's media diet: bookmarked Twitter threads (organized by folder), referrals from close contacts, long-form essays
• 95% evergreen — things written to last, not to trend
• Sites: readsomethinggreat.com (manually curated essays, five at a time across five categories) and alias.co (every podcast, essay, and video by a curated set of thinkers)
• Rarely uses Google for discovery — the best content hides in the internet's nooks and crannies, surfaced by curation or referral
• Newsletters he reads: Morning Brew, James Clear's 3-2-1, Not Boring (Packy McCormick), Ben Thompson (Stratechery)

Making inner work go viral — vitamin vs painkiller

• Stoicism and mindfulness are vitamins: long-term benefit that compounds invisibly
• People gravitate toward painkillers — things that alleviate pain today
• Ryan's solution with The Obstacle Is the Way: position a piece of stoic philosophy as a solution to a specific problem people already have
• The reframe that works: "this vitamin is actually a painkiller" — meet people at the moment of crisis, then expand the framework
• Curation and translation are undervalued relative to original creation; Morning Brew and Daily Stoic both succeed by making existing ideas accessible, not by inventing new ones