Alex Lieberman is the co-founder of Morning Brew, the wildly successful newsletter-turned-media-empire that made business news actually fun to read. After selling it for an eye-popping $75 million, he went on to cofound Tenex, a company helping businesses innovate with AI, and storyarb, which helps on the content creation side of marketing. Recently, Alex joined me on How Success Happens to share the raw, honest story behind his journey — from being a bullied kid to becoming a relentless builder of big things. “I didn’t feel smart. I didn’t feel attractive, I just felt less-than,” he explains. “And I felt this deep desire to prove that I wasn’t mediocre.”
We dug into why being naive can be your biggest advantage, how to delegate like your business depends on it (because it does) and why AI isn’t the devil. Alex’s insights are packed with real talk and actionable wisdom that’ll help your personal success take off in three, two, one!
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Three Key Insights
1. The Power of Being Naive
Alex and his co-founder, Austin Rief, had zero media experience when they started Morning Brew. And that turned out to be their superpower. “I think being naive to an industry is actually an amazing way to just think about an industry differently because we didn’t know what the status quo was. We didn’t know how things should be done,” Alex explained. They didn’t start with dollar signs in their eyes either — Morning Brew was a passion project for over a year before they even considered monetizing it. That allowed them to focus purely on solving a problem: making business news engaging for college students who hated reading The Wall Street Journal.
Takeaway: Don’t wait until you’re an “expert” to start your business — your fresh perspective might be exactly what the industry needs.
2. Delegate Everything You’re Not “World-Class” At Doing
One of Alex’s most game-changing realizations? You don’t need to be good at everything. In fact, trying to be is a recipe for burnout. “Ask yourself, ‘What are the two or three things that I think I’m best-in-class at?’ Only spend my time on those things and then delegate everything else out,” he said. For Alex, that meant focusing on relationship building and networking while his co-founder handled operations. And for tasks he truly hated—like taxes—he found specialists who actually loved doing them. (Yes, those people exist.)
Takeaway: Identify your two or three superpowers, double down on those, and find people or services to handle the rest — your business will thank you.
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3. AI Is a Fun House Mirror (Not Magic)
Alex’s latest venture, Tenex, is all about helping companies unlock AI’s potential. But he’s quick to dispel the hype: AI isn’t a magic wand. “It’s like a fun house mirror: It makes exceptional employees who are great at what they do ten times better. It makes mediocre employees worse because it just creates slop based on their lack of clear thinking,” he said. The key? Treat AI like an editor working with a writer — it needs clear direction and collaboration. When his co-founder rebuilt an entire engineering product with just one person (instead of nine), they became five times more productive by using AI strategically.
Takeaway: AI won’t solve your problems automatically — but if you’re already great at what you do and willing to work with it intentionally, it can multiply your output exponentially.
Two Great Ways to Learn More
- Follow Alex on LinkedIn and X to get his daily insights into how tech is driving entrepreneurship.
- Read this deeper dive into the story of how Alex and his co-founder built and grew Morning Brew.
One Question to Ponder
Alex shared something powerful in our conversation: His dad passed away suddenly while Alex was at college. It was devastating, and it also gave him a perspective that shaped every decision he made afterward. It made me wonder: What’s one painful experience from your past that, in hindsight, gave you an unexpected advantage or clarity about what really matters?
Send your answer to howsuccesshappens@entrepreneur.com—I’ll be reading responses on a future episode!
This episode was brought to you by Intuit TurboTax. With the business tax filing deadlines approaching quickly, understanding what has changed and acting on it with the right guidance may be one of the most practical decisions a solopreneur makes this year. Learn more about filing your taxes with Intuit TurboTax, visit turbotax.intuit.com
About How Success Happens
Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.
Alex Lieberman is the co-founder of Morning Brew, the wildly successful newsletter-turned-media-empire that made business news actually fun to read. After selling it for an eye-popping $75 million, he went on to cofound Tenex, a company helping businesses innovate with AI, and storyarb, which helps on the content creation side of marketing. Recently, Alex joined me on How Success Happens to share the raw, honest story behind his journey — from being a bullied kid to becoming a relentless builder of big things. “I didn’t feel smart. I didn’t feel attractive, I just felt less-than,” he explains. “And I felt this deep desire to prove that I wasn’t mediocre.”
We dug into why being naive can be your biggest advantage, how to delegate like your business depends on it (because it does) and why AI isn’t the devil. Alex’s insights are packed with real talk and actionable wisdom that’ll help your personal success take off in three, two, one!
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