16 Apr 2025 · 17 min
Alex Lieberman, who built Morning Brew and launches one to two businesses yearly, shares his core business tools, particularly Gusto for HR. He looks for platforms that are intuitive, affordable for bootstrappers, and handle payroll, benefits, hiring, onboarding, and taxes in one place.
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What's up, everyone? This is Alex, the host of Founders Journal. As you may know, I built Morning Brew from my senior year of college until we sold the business in 2020. And now I'm building a variety of businesses in different spaces and different stages. I'm basically averaging 1 to 2 new businesses per year. And because of that, I have had the opportunity to test a ton of different products and services, ultimately landing on a core software stack that serves as my business operating system whenever I start a new company. I have my go-to banking service. I have my go-to formation service. I have my go-to domain hosting service. But probably the most important of them all is my HR service, Gusto. If you're a longtime Founders Journal listener, you know how much I think about people in the context of business. A business is nothing without its people, which means a platform that helps me manage and take care of my people is invaluable. And that means I've tried every HR platform under the sun, always with the same exact goals in mind. First, I want a product that's intuitive and delightful to use. As a non-HR person, I find the intricacies of payroll, benefits, taxes, compliance, and expenses to be painful. So I just want something that makes my life easier. Second, I want it to be affordable.
I'm a bootstrapper at heart.
I started Morning Brew with $0 and I started StoryArc with $0 as well, which means I don't have infinite dollars to drop on SaaS products. And third, I want a platform that acts as my one-stop shop for all things people. I want it to handle payroll, benefits, hiring, onboarding, and taxes, all while integrating with all of the other tools in my business stack, whether it be QuickBooks, Slack, or Google Workspace. Well, Gusto hit the trifecta, which is why I am a customer and use it for every single one of my businesses. Yes, this is a paid sponsorship by the amazing team at Gusto, but I would sing their praises even if I wasn't being paid to do so. So if you're looking for a platform that takes the pain out of payroll, benefits, and HR, I highly recommend you check out Gusto. And if you sign up at gusto.com/alex, you will get your first 3 Now onto the episode. What's up everyone?
This is Alex Lieberman and this is Founders Journal. For those who are longtime Founders Journal listeners, welcome back. For those who are new to the show, here's the deal. Founders Journal is my audio diary made public for the world. My goal is to increase your odds of success as an entrepreneur by sharing the stories, lessons, and tactics that I experience as I build my businesses. You can expect the podcast Monday and Wednesday with episodes that are under 20 minutes in length. And if you want to get notified when a new episode drops, Comes out, make sure to subscribe wherever you listen. Today on the podcast, I'm talking about limiting beliefs, the range of limiting beliefs I've experienced throughout my life and career, and my process for navigating them healthily. Lastly, if you haven't yet introduced yourself, please do so. I love getting to know Founders Journal listeners, so shoot me an email at alex@storyarb.com. That is alex@storyarb.com. Say hi, and I'll get the conversation going. Now let's get into it. We all have limiting beliefs, but are sometimes too chicken shit to admit it. But it is important for founders who have quote unquote made it to share them openly. Otherwise, the next generation will assume that their role models are perfect, which is harmful. Let me take you through some of mine. I have had limiting beliefs for as long as I can remember. In high school, I had one core intellectual limiting belief and one core social limiting belief. The intellectual one was, I'm not smart enough. I convinced myself that I was a mediocre student because everyone else in my grade was a genius, whereas I wasn't, and because I didn't have the ability to focus when it really mattered. I vividly remember believing that no matter how hard I tried in class, I was a B+ student at best. And even if I worked as hard as I possibly could on an essay for an English class, something in the A range would never grace my presence. The social limiting belief was that I'm not attractive. I'm not cool. I'm not good-looking. I'm not confident. I'm not funny. And because of that, I have no chance of attracting someone to like me, date me, or kiss me. I believed this at my core. To me, this wasn't a story that I repeated over and over. It was a fact. And because it was a fact, I subconsciously behaved in a way that validated the story. I was awkward. I dressed like a schlep. I engaged in social situations with a lack of confidence, not because I was actually unattractive, but because I had convinced myself that I was. Now, you may be saying to yourself, okay, that was high school Alex, but what about Morning Brew Alex? We all go through our awkward teenage phases. But what about when you were seemingly crushing life and succeeding as an entrepreneur? Short answer, I had just as many limiting beliefs during my time running Morning Brew. Those beliefs just evolved to protect myself from what I subconsciously considered to be my biggest risks in that phase of life. I'm not smart enough and I'm too unfocused were all-encompassing stories that I had from 2015 to 2021 while running the Brew. What's interesting to examine is why certain beliefs went away and others continued as I got older. I'm not attractive became less pronounced as I got older for 2 reasons. One, there started to be evidence that I was attractive and confident and all the things that you think you need to attract a partner. I attracted my wife, who I think is the most beautiful woman in the world. And so I had proof that I had to at least be attractive enough to convince her to be with me and marry me. And second, because I had found my life partner, which is the number one requirement of our reptilian brain, the limiting belief no longer carried weight since not being attractive only really mattered while I was single and still in search of my person. So then why did I'm not smart enough and I'm too unfocused stick around? Because they were directly tied to how I ascribed value to myself at that point in my life. And I find that limiting beliefs attach themselves to the things that are most identity-provoking to you. Said differently, a limiting belief is something that, if true, would risk your entire identity. And your identity is how you try to make sense of your value and importance in the world. 2015 to 2021, my identity was entirely tied up in my role as CEO of Morning Brew, which meant that being a great CEO was wildly important to me since I bet my whole identity on my professional path. Moreover, at the time, I had a certain definition of what a great CEO was. It was someone who was deeply focused, had strong opinions, made decisions unemotionally, and saw around corners. In hindsight, I realized that definition was really just a projection of all of the things that I told myself I did not have and that my co-founder Austin did have, because we as human beings are horrible at acknowledging our strengths. That doesn't serve us evolutionarily, and we're great at only focusing on our perceived deficiencies and then turning those deficiencies into requirements to be valuable. It's kind of messed up when you think about it. We literally create definitions of success that we build to fall short of, and yet it makes so much sense. Our brain wants to keep us safe, and its trained way of doing so is focusing on the stuff that poses a perceived risk to our safety. For me, safety meant being a great CEO, and the story of lacking focus was my brain's way of creating awareness around something that could jeopardize my feeling of safety. Up to this point in my life, I really had no awareness or control over my limiting beliefs. But that all came to a head in 2021. When I stepped out of the CEO role at Morning Brew and got punched in the face by my beliefs. For an entire year, I was stuck. I was unmotivated. I felt directionless. I felt unsuccessful internally despite being considered successful by others externally. Part of this was driven by the identity whiplash that occurred after giving up my professional title but not having an identity fallback personally. But the other big part of this was needing to navigate some very strong limiting beliefs. Let me talk about what those beliefs were and my process for working through them. I wasn't actually a good entrepreneur was the first. This will be the biggest and only financial windfall of my life was the second. I can't be a great entrepreneur and a great family man was the third. Working through these limiting beliefs and any limiting belief for that matter takes a lot of time. I have been working through them for 4 years now, and while I've made a lot of progress, I know they still hold me back in a variety of ways. So let me take you through my process. First is understanding what a limiting belief is. A limiting belief is a story that you have about yourself that you treat as fact, even if the belief hasn't been tested and substantiated. It can be as benign as, I'm not a football fan, even if you've never watched a minute of an NFL game in your life. Or it can be as powerful and dangerous as, no one loves me. I'm meant to be alone. Again, limiting beliefs can exist for a few reasons. They can act as a survival mechanism. Our brain tries to protect us from future harm by reinforcing the idea that avoiding certain actions or situations is safer. They can be formed based on early life experiences. So past negative feedback or trauma can program our brains to expect the worst, forming beliefs that limit us, often long after the original situation has taken place. And they also can mirror our evolutionary programming. We have a well-documented negativity bias as people. We naturally pay more attention to negative events than positive ones. So for example, one critique might sting more than 10 compliments feel good. From an evolutionary perspective, this bias, this negativity bias, kept our ancestors alert to threats, which is why we are likely the descendants of quote unquote worriers. The second thing after you understand what a limiting belief is, is bringing awareness to your belief system broadly. This is the most important step because you can't face things that sit outside of your awareness. A few ways that I have brought awareness to my limiting beliefs. First is by identifying patterns in how I describe myself to others or how others describe me when I ask them to provide feedback. I very quickly realized that the way I learned to describe myself followed a very repetitive script. I would always say, I'm a 0-to-1 founder. I'm highly distractible. What makes me creative also makes me super ADD. I don't enjoy the more operational part of building a business after the zero to one. So from this exercise, it became crystal clear that I identified as someone who lacks focus and treats that story as fact. The second way to bring awareness is by examining current behaviors and understanding what those current behaviors implicitly mean you have assumed about yourself. Again, it becomes very obvious that I have labeled myself as a highly distracted 0-to-1 founder in the fact that I am building a portfolio of companies versus just focusing on one. And I am only focusing on the early stages of these companies before I bring on a co-founder and a CEO. Basically, I've created this entire infrastructure around my life as a hedge for my distractibility. This leads to step 3 in the process, which is separating out your limiting beliefs. The two exercises I just shared with you are methods for listing out and understanding all of your beliefs, your entire belief system, and bringing them from unconscious to conscious. But to actually understand your limiting beliefs, you need to go through the list from the previous step and identify which ones either you've never actually tested, meaning you treat the belief as truth even if you haven't proven that it's true, or it's a belief that if you're wrong about it, even if you have tested it in the past, the consequences would be significant if you wrongly assume that. that this belief is actually the truth. The next step in the process is understanding your options. So what can you do once you know what your limiting beliefs are? So let's use one of my limiting beliefs as an example. I'm not a good entrepreneur. I only succeeded with Morning Brew because I got lucky and had a great co-founder. So what am I to do with this belief? I have a number of options, and there isn't necessarily a right or a wrong option, just a bunch of trade-offs. Option number one, focus on weakening the belief. One way to weaken the belief is to play out the worst-case scenario, because oftentimes worst-case scenarios aren't nearly as bad when verbalized. The worst-case scenario here is that if I'm not a good entrepreneur and I only succeeded because I got lucky, then I'll either have to get lucky again or I just won't be an entrepreneur again. And if I am not an entrepreneur again, I still have a life that I am so grateful for. I have my health. A loving family, financial freedom, and so much privilege. Even with the worst-case scenario, I am wildly grateful. The second way to weaken the belief is to test the belief. Testing the belief is the best way to understand if you're conflating feeling and fact, and if so, by how much. One of the ways I tested the I'm not a good entrepreneur belief is by having a 2-hour phone call with my co-founder Austin, sharing all of my stories about my lack of value to the business, and then asking him to be 100% forthright about about how he perceived my worth to the business. Through this exercise, it became incredibly clear that I became fixated solely on my deficiencies as an entrepreneur, and I was blind to all of the ways that I added value. The 3rd way to weaken a belief is by adding yet to the end of a self-deprecating story. So instead of I'm not a great entrepreneur, what if I made it I'm not a great entrepreneur yet? By adding yet, I create a possibility, and by creating a possibility, I give myself the choice to explore what it could look like to become a great Entrepreneur, if that's what I even want to do. Yet allows you to be in control of your own destiny, while limiting belief puts you in the passenger seat. The second option for facing a limiting belief is proving the belief wrong. Now, this is a risky one. When you aim to prove a story wrong, you open yourself to large trade-offs that don't consider the life consequences outside of the very story that you've told yourself. The 70-year-old serial entrepreneur who has generational wealth but is alone and unhappy very likely had. The limiting belief of I'm not good enough, I'm not worthy, or I'm not cool enough. And they opted for the path of challenging that belief at the expense of what could actually bring long-term happiness to them. Now, on the other hand, proving certain limiting beliefs wrong can be a huge unlock in your life. I personally want to prove my limiting belief that I'm distractible and unfocused wrong. I don't want it to define me. And I believe that this belief has become a self-fulfilling prophecy where I have become less focused because I call myself So as you think about whether it's worth proving a belief wrong, I would encourage you to ask yourself a very simple question. In an effort to beat this belief, what will be the net impact on the entirety of my life? Not just this one thing. And that leads into the final step, which is making a choice. The beauty of all of this is once you have awareness around your limiting beliefs, you get to choose the role you want to play in facing it. You can choose to weaken it, You can choose to let it flow through you without attaching your identity to it. You can choose to prove it wrong. And more than that, you can change your choice as you learn, as your life evolves, and as your perspective changes. Just remember, we all have limiting beliefs. They will likely never go away, but they also do not need to define who you are. That is it for today's Founder's Journal. As always, I love to get to know my listeners, so please shoot me an email to alex@foundersjournal.com. storyarb.com saying hi, hola, or what's up, and I'll get the conversation going. Thanks again for listening, and I'll catch you next episode.
