What comes after you build and sell the company that has defined your entire adult life?

Alex Lieberman co-founded Morning Brew as a college student after noticing that traditional business news felt dense, dry, and disconnected from the way young professionals wanted to consume information. What began as a Microsoft Word document emailed to a small group of students grew into one of the world’s most recognizable business media brands and ultimately led to a reported $75 million deal.

But the exit was not the end of Alex’s entrepreneurial journey. It became the beginning of a deeper conversation about identity, leadership, purpose, and what success is actually supposed to feel like.

Alex is now on his new entrepreneurial journey building Tenex, an AI transformation consulting firm.

In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Alex to unpack the decisions behind Morning Brew’s growth. Alex shares why he walked away from his dream job at Morgan Stanley, how he found a co-founder whose strengths complemented his own, and what he learned when the business needed him to evolve from a builder into an operational CEO.

This is an honest, thoughtful conversation about building something remarkable while remembering that your company is something you do, not the entirety of who you are.

You’ll learn:

How Alex Lieberman transformed a college newsletter into Morning Brew
Why early reader behavior revealed that the idea had real potential
Why regret minimization helped him make a life-changing decision
What happened behind the scenes during Morning Brew’s acquisition
Why the $75 million exit felt different from what Alex expected
How OCD and panic attacks affected Alex’s experience as a founder
Why founders can struggle with identity after an exit or leadership transition
How to build a “purpose portfolio” beyond your professional title
How to choose an executive coach for your current challenges
Why reflection is an essential part of growing from founder to leader

We talk about:

00:00 Meet Morning Brew co-founder Alex Lieberman

01:08 How a college newsletter became Morning Brew

04:16 Finding a co-founder with complementary strengths

08:19 Leaving Morgan Stanley to build Morning Brew full time

10:31 Using worst-case scenarios and regret to make difficult decisions

19:18 Navigating Morning Brew’s acquisition during the pandemic

23:25 Why the $75 million exit felt surprisingly underwhelming

28:32 Realizing he was a builder CEO, not an operational CEO

31:34 Leading a growing company while managing OCD and panic attacks

36:01 Losing his identity after transitioning out of the CEO role

40:00 Rebuilding through reflection, experimentation, and connection

50:19 Why every founder needs a diversified “purpose portfolio”

57:27 Making mistakes as a strategy for entrepreneurial growth

01:00:45 What Alex wishes he had understood earlier

Follow Alex on

Instagram: https://www.instagram.com/alexlieb
LinkedIn: https://www.linkedin.com/in/alex-lieberman/
Website: https://alexlieberman.com/

Connect with Alisa!

Follow Alisa Cohn on

Instagram: @alisacohn
Twitter: @alisacohn
Facebook: facebook.com/alisa.cohn
LinkedIn: https://www.linkedin.com/in/alisacohn/
Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better)

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

124: Alex Lieberman Built Morning Brew to $75M. But That Was Just the Start [ENCORE]

From Start-Up to Grown-Up

124: Alex Lieberman Built Morning Brew to $75M. But That Was Just the Start [ENCORE]