In this episode of the Founders Journal audio diary, Alex Lieberman—co‑founder and executive chairman of Morning Brew— revives the “Startup Hotline” segment to answer listener questions about building and scaling businesses. He first tackles Jack Raines’s query about what company he would start tomorrow, proposing a two‑question decision framework: (1) identify a personal “suck” that also affects many people and that he can stay passionate about, and (2) ensure the idea can sustain rapid, long‑term growth. He cites the creator economy and mental‑health space as two sectors that meet these criteria. Next, Mady Mao asks for his definition of success. Lieberman explains that his view has shifted from a focus on professional achievement and money (driven by a personal family financial need after his father’s death) to a present‑day emphasis on keeping his word, setting high personal expectations, and growing quickly in any endeavor. He then answers Alex Brogan’s question about the top three characteristics of junior team members that predict future startup leadership: an obsessive work ethic, being impeccable with one’s word, and strong critical‑thinking ability. Finally, Melissa Chowning asks about his favorite interview question. He says he usually asks “What motivates you?” (or a variant, “What do you love obsessing about?”) to surface obsessive drive and motivation, noting the trade‑offs of chip‑on‑the‑shoulder versus fear‑of‑loss mindsets. Throughout, Lieberman weaves personal anecdotes, practical frameworks, and actionable hiring advice, and invites listeners to submit more questions via email or Instagram.
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What's up, everyone? This is Alex Lieberman, co-founder and executive chairman of Morning Brew. Welcome back to Founders Journal, my personal audio diary, where I give you, the business builder, the tools you need to think better in order to build better, whether that's building a business, a team, or a new product. Today, I am bringing back an old segment called Startup Hotline. This is a segment of Founders Journal where I take any and all questions about building and scaling businesses and all of the questions that I am about to answer came from the Founders Journal community, either over email or Twitter. So without further ado, let's hop into it. This first question comes from Jack Raines on Twitter. Jack asked, if you were going to start a new company tomorrow, what would that company be? Here's how I'd answer the question, Jack. I think there is a more important question than what would the company be? I think the right question to ask is, if I was going to start a company tomorrow, why would I start a new company? And for me, I would start a company if it satisfied 2 of my needs. The first need is it would have to answer the 3 questions that my friend Micky Agarwal uses to launch all of her new businesses. The first question is, what sucks for me or what sucks in my world? The second is, does this suck for a lot of people? Meaning, is it a big opportunity? And finally, can I be passionate about solving this sucky problem for a long time? That is the first thing that I would need to get out of any new company I start. The second is, could this new company that I start give me the ability to grow really quickly for a long time? And so if I answer those 2 questions, if I'm able to answer those 2 questions, I would start a new company. Otherwise, I'm not just going to bias or default to starting a new company because that is what is expected of startup founders. And for me, what are 2 areas that I think satisfy these 2 criteria that I just spoke about? The first is building something in the creator space or within the creator economy, and the second is something within mental health. So great question from Jack. Moving on, we have a question from Mady Mao. Mady asked, what is your definition of success? So for me to answer that honestly, I have to start by saying my definition of success has definitely changed over time. If you were to ask me when I was starting Morning Brew, I would've said my definition of success is partly for professional achievement and to build something awesome in business, and partly for money. And I feel like it's taboo for startup founders to say, oh, I built something because I wanted to make money, but I would feel disingenuous if I didn't share that. And for me specifically, you know, after losing my dad a week before junior year of high school, all that I could visualize was basically only money out in the Lieberman household and no money in, because my mom, who had worked on Wall Street for 20 years, she was retired by this point. And I just couldn't help think about that. All that the Lieberman household was doing was spending money. And so a big motivation for me, honestly, in the early days of the Brew was I wanted to build something big enough that could sell for enough money such that I could cut a 7-figure check to everyone in my family, my mom, my sister, and my grandparents. Now, if you were to ask me today, what is it that motivates me, or what does success look like for me? I would say it's 2 things. It is doing the absolute best that I can with the work that I commit myself to. Over time, I've realized that keeping my word to myself and setting my goals or my expectations for myself super high is a really important thing to me. And every day that I do keep my word to myself, I feel really good and successful about the work I'm doing. Any day that I basically don't set a high enough expectation for myself and don't keep my word to myself, I don't feel successful in what I'm doing. And the second thing that I need to be successful today is growing quickly in whatever I do, whether it's recording this podcast, whether it's being the executive chairman of Morning Brew, whether it's starting anything new, it has to be something where I can grow quickly. I feel successful when I am growing and evolving myself quickly. When I feel like I'm stagnating or plateauing in my career, that is when I feel unsuccessful. Okay. That was a great question from a Founders Journal listener. Let's move on to the next question from Alex Brogan. Alex asked, What are the top 3 characteristics in a junior team member that are indicators of future success within a startup? And they basically said, i.e., this person will go on to be an extremely high-performing employee and they'll go on to be in leadership roles. Basically, for me, there's a few criteria that when I look at not just junior employees but any employee, it is indicative of future success. The first is someone who has an obsessive work ethic. I say that because an obsessive work ethic is hard to teach. I've never been able to teach someone how to work significantly harder than they are today. It also means that if they are working obsessively, it probably means that they're thinking obsessively about the business. And it's pretty impossible to be a critical thinker if you are not being an obsessive thinker. The second thing I look for in junior employees is someone who is impeccable with their word. And this goes from kind of like the most innocuous thing, like saying, hey, let's meet at 2:00, and they are there by 2:00 every time, all the way to saying, hey, there's this huge deliverable I need by next Tuesday at 1:00, and I never question if they will get it to me. The best junior employees who are impeccable with their words, they basically can make you a promise that they will get you something, say, a week or 2 weeks from now. You can go to sleep and basically be in a deep sleep for weeks and never have a concern that they will not deliver whatever they have promised on time. The 3rd characteristic of junior employees that show a ton of promise— I alluded to this with the first one, which is having an obsessive work ethic, and that is someone who is a strong critical thinker. I honestly believe critical thinking is the number one skill to be successful in business. And what does that effectively mean? It means you are a professional who changes your actions on a daily basis based on new information that you are getting from your customers, from the business, etc. So few people are critical thinkers, but you need to be a great critical thinker to build a business or to grow into a leadership role within a business. And so those are the 3 things that I look for in junior employees: critical thinking, obsessive work ethic, and someone who's impeccable with their word. Let's take one more question from Founders Journal listeners. This one comes from Melissa Chowning, and Melissa asked, what is your favorite interview question to ask a prospective employee? So I caveat all this by saying it really depends on the role, but in general, my favorite general interview question, no matter who I'm interviewing, is very simple. I ask the question, what motivates you? And I ask that question because it hits at the heart of, is this person an obsessive thinker? Are they an obsessive worker? And can they get obsessive about the business? And I've talked about this in a previous Founders Journal episode, but I think one of the strongest motivators in business is either someone who has a chip on their shoulder or someone who has a fear of losing. That is what causes a lot of people to be obsessive thinkers. Now, I will call out that there are big trade-offs of this. It can really impact the personal life of someone who is operating because of a chip on their shoulder, but it is highly effective in career. If I don't ask that question, which is what motivates you, another and kind of similar question I'll ask is what is something you love obsessing about? And it could be related to work or not related to work. And I basically say, what's something you love obsessing about? And tell me about it. This was actually the question that I asked to Morning Brew's second writer ever who became our managing editor. And he answered basically saying, I obsess about US history. And so for basically 30 minutes of our 40-minute interview, he gave me a masterclass on US history and specific battles that I had never heard of before. And I could just tell once he got engaged by something, he would be so engaged and he couldn't not think about it. And so I got a ton of other questions from Founders Journal listeners. We only have so much time on the pod, so I'm gonna stop there. But if you wanna see me answer other questions, I actually am gonna answer more of them on my Instagram, so you can follow me @alexlieb. But I would also love to hear from you, from those of you that haven't yet reached out to me with your question. So any question related to business building, how do you start a business? How do you scale a business? How do you grow as a leader? How do you think about hiring and firing? Any question you have. Send it to alex@morningbrew.com. I'm going to use those questions for future startup hotlines, and maybe I'll just feature one of these questions in an upcoming episode. But other than that, thank you so much for listening, and I'll catch you next episode.
