In this diary‑style episode of the Founders Journal podcast, Alex Lieberman reflects on a self‑imposed, decade‑long limiting story that he believed defined his worth as an entrepreneur. He recounts how a coaching prompt from Dave Kashin urged him to share this narrative with his co‑founder Austin, leading to a candid 2.5‑hour conversation where Austin highlighted Alex’s superpowers—relentless resourcefulness, relationship‑building, obsessive product focus, and the ability to turn rejections into opportunities—while also noting areas where Alex was less effective, particularly in scaling operations during Morning Brew’s transition to a larger organization. Alex discovers that his earlier story was largely false, recognizing his indispensable role in the company’s early growth and accepting that a different skill set was needed for later stages. He expresses gratitude for the conversation, the co‑founder’s friendship, and the newfound belief that he can create whatever he wants, illustrating the profound impact of internal narratives on confidence and leadership.
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What's up, everyone? Welcome back to another episode of Founders Journal, my personal diary made public for the world. Today I am showing you the power of stories through a story that crushed me for nearly a decade. If this episode resonates with you and you want to say hi, or if you want to share a similar story or limiting belief in your life, shoot me an email to alex@morningbrew.com. I'd love to hear from you. Without further ado, let's hop into it. For the past 8 years, I've had this story of myself, a story I've repeated so many times that I forgot it was even a story. It has just become my inevitable truth. And the story goes as follows. I am not a talented entrepreneur. I made one good decision bringing on my co-founder Austin, but other than that, my entire entrepreneurial journey has been luck. My lack of focus, lack of discipline, my excitability, and inability to think at the systems or process level made me useless while building Morning Brew. I gave power to this story, which left me feeling powerless. As the world celebrated me for my success as an entrepreneur and Morning Brew's meteoric rise, I criticized myself for being a liability to my business and my co-founder. And as I stepped out of the business in 2021, just 6 months after selling the company and having a life-changing outcome, a time in which most feel their most successful, most confident, most capable, I felt my most vulnerable. Post-acquisition, I would say to myself, Alex, protect your money at all costs because this will be your one and only big financial outcome ever. You can only be so lucky. Now you need to play defense. And as I write this, I can't help but feel sadness for younger Alex. What a lonely, limited, small way of being. A 28-year-old with their entire life ahead of them, the privilege of time and unlimited optionality, yet the only possible future they see is quasi-retirement, financial insecurity, and deep feelings of inadequacy. Thankfully, the story gets better. One day I was chatting with my coach, Dave Kashin, And I shared with him the story that I just shared with you. He listened, he nodded, he felt my pain, and he took a deep inhale and asked a simple question. Alex, have you ever shared this story with your co-founder Austin? I said, I have not. Well, I'm going to ask you to share this story with your co-founder. When can you do that by? I said, I'll talk to him before our next meeting. Dave said, great, let's see if he agrees with your story. What the fuck did I just agree to? That was my first thought. My second thought was, how didn't I think of doing this on my own? Immediately after my coaching session ended, I shot a text to Austin. I said, can we find 20 minutes next week? I'm doing an exercise with my coach, and one piece of it involves you. It involves limiting beliefs and your perception and thoughts of me from working together. He quickly said yes, and we agreed on a time. I wanted to make sure I gave him the opportunity to reflect on years of running the business together, so So I followed up with questions that I would be sharing on the call. It said, questions I'm going to ask you when we talk, if you want time to think them over. First, when did I seem most alive or excited while in the CEO role at Morning Brew, both in terms of stage of business and the type of work? Second, what do you think are my superpowers? Third, what are my Achilles heels? And fourth, what is your story of me as a co-founder slash CEO when I was in the day-to-day? How did I impact the trajectory of the business? Where did I hold the business back? When was I'm most valuable, least valuable to the business. And I finished the text by saying, and I want you to be purely objective and not at all edit your thoughts with regards for my feelings. 4 days later came the moment of truth. What would Austin say? Was my story true? Did he think of me as a valuable partner or dead weight? I was nervous, but also excited to learn from someone who knew me so well. We hopped on the phone, and 2.5 hours later, I had my answers. Here is the punchline. My story, the story I had convinced myself for 8 years straight was my reality and an inevitability for the rest of my life. That story was, in fact, not true. Now, I'll caveat by saying that there were truths to parts of my story, but the story was far from the truth in its entirety. I learned from Austin that I was invaluable in the early years of the business. That without my tenacity to will this company into existence by any means necessary, without my unapologetic belief in our vision for what Morning Brew could become, without my ability to build relationships with brands, investors, and employees, without my obsessiveness about our product and our content, we would have never had the opportunity to build Morning Brew into a 200-person, $75 million a year business. I learned that Austin learned many things from me. A fact I never even considered because I always thought about how much I was learning from him. He learned what it looked like to be endlessly resourceful and somehow transform an idea into a great product that solved a very real problem. Things like hiring a voice editor from Michigan's improv troupe to create the conversational, witty tone our content has become known for, or turning a rejection from Discover Card into an opportunity to talk one-on-one with their CMO and turning that into a relationship that led to our first 6-figure advertising deal. He learned what it meant to be relentless, stopping at nothing to get what we needed to push the business forward. This included reaching out to advertisers for the 20th time, getting a no, and still finding a way to turn that no into a yes. Or maniacally line editing the next day's newsletter until 2 a.m. to make sure the 5 minutes people spent reading our newsletter was pure joy. Or littering Michigan's common areas with thousands of 2x2 flyers only to have employees remove them and only to have me come back the next day and do the same exact thing. Thing, and he learned what genuine curiosity in people and their stories looks like and how that leads to authentic relationships. I'm not going to lie, it felt really good to hear that, to truly know what someone I care so much about and value so deeply thinks of me, and to know I did in fact drive this business forward. It gave weight to my worth, and it helped me realize how powerful and oftentimes destructive our stories can be. But I did mention there was some truth to my story, so I would be remiss to not share that. In 2019, Morning Brew needed to change. We had a dozen employees. The business was highly profitable and on an 8-figure run rate, and we had ambitions of being more than just a newsletter company. Yet cracks were starting to show. We didn't have concrete goals. We didn't have senior leaders, and we didn't have communications that could support a team that could no longer fit around a dinner table. To be able to operate and scale the business effectively, we needed to work on the business versus in the business. And to do that, we needed an organizational operating system and a CEO that could drive that system forward. I wasn't that guy, a fact that I am at peace with today, but for years was the only fact that I could focus on. And I now understand why I couldn't be that guy at the time. I lacked the urgency to acknowledge that we had entered a new era of the Brew, an era defined by process, planning, and operations, not by scrappiness, salesmanship, and in-the-weeds product obsession. And I lacked the skills and the interest to do what was necessary to build that system and lead us gracefully into that new era. But as I reflect on this experience, I can't help but feel immensely grateful. I feel grateful that I was led to a long overdue conversation with my co-founder that I may have never initiated on my own. I feel grateful that I have a co-founder and a great friend who could shepherd the next era of Morning Brew so that I didn't hamstring its growth at the time. And I feel grateful that I no longer believe that shitty story that I told myself for nearly a decade. I have a new story that I know now to be true, and that story is that I have the power, the abilities, and the skill to create whatever I want in this world. Thank you so much for listening, and I'll catch you next episode.
